The response to the beginning of my “Sheila” series was encouraging. However, most who left comments thought chapter 1 was too brief (which, to my mind, is a more favorable opinion than finding it was too long). In any case, the point is well taken. So for this segment, at one reader’s suggestion, I have combined material from what was to appear in two chapters of my original plan into what I hope is a more acceptable length. (See there? Writers do occasionally listen to their commentators.)
To those readers who took exception to the reaction of my protagonist in seeing his wife degraded before his eyes, I can only say his arousal is in keeping with the ambiguous feelings I have given him at this point in the story. My hope is that I’ll be able to make Tobe Lanscott more interesting and complex than just another angry avenger or another mere wimp.
“Sheila” is my attempt at a “hard-boiled” crime story, the kind that used to appear in pulp magazines (with an erotic slant, of course). In keeping with that style of writing, I’ve tried to move the story along largely through dialogue and action, and have accordingly minimized interjections, explanations and background.
In addition to the main plot idea — a man tracking down his runaway wife — I’m introducing several subplots in this installment and the next, all of which will be resolved in the last chapter. I’m a slow writer, so I hope “Searching for Sheila” will be of sufficient interest to earn your patience. Unlike my “Mrs. Sutton” series under the “mature” category, in which I intended each installment to be self-contained, in “Sheila” my intention is to present one continuous narrative.
I’ve been carrying this story around in my head for weeks, so I know where I’m going (I think). Anyway, I’ve found all comments, of whatever persuasion, to be helpful. Thanks for listening.
Three days later Lanscott was headed north to Piedmont, hardly hearing the rattles of his eight year old panel truck. To keep his mind from thoughts of Sheila, he went over the two jobs he had just completed – kitchen cabinets for the Suttons, and new paneling downstairs for the Cochrans. Both were routine jobs, but finishing them up occupied him the last couple of days, keeping his mind off where he was going and what he thought he had to do. And, yes, off those images of Sheila being ravished by Pharaoh and his men — and seeming to enjoy it. He couldn’t bring himself as yet to dwell on what he had felt while watching those images – that incongruous combination of anger, humiliation and undeniable arousal.
Approaching Piedmont, Tobe noticed changes in the landscape. Passing through flat farmland he entered an area of evident economic depression. He glanced at a drive-in that hadn’t shown a movie in years. The front gates to a cavernous empty factory were padlocked. A strip mall was largely boarded up with grass growing in the parking lot. The large windows of a car dealership were smashed and its expansive lot empty. The road to Piedmont was bordered with busted dreams. And maybe that’s what I’m bringing here, Tobe reflected — a busted dream.
A mile or so from Piedmont’s corporate limits, Tobe pulled into a motel which looked as though it might have been built about the time Nixon was resigning. It looked like another dream about to go bust. The man behind the counter seemed surprised he had a customer. He was pale and thin with cheeks sunken from missing teeth. His breath came at Tobe in equal amounts of alcohol, tobacco and a stale life.
” Where you from, buddy, if you don’t mind me asking? “
” Ravensfield. “
” No kiddin’. And you’re stopping here? You got friends around here? “
” Don’t know a soul. But I heard if a man wanted to get laid he could do worse than come to Piedmont. “
The man grinned, revealing about as much space as teeth.
” Buddy, you got that right. Maybe I could help you out along those lines. What’s your pleasure, if you don’t mind me askin’? “
” Anything, as long as it involves a woman. ” Tobe gave the man a broad wink. “My wife left me about a year ago, and I’m so dumb, I’ve been faithful to her ever since. “
” That’s not only dumb, buddy, but downright unhealthy, if you don’t mind me saying. A man’s gotta get his horns trimmed regular, if you know what I mean. “
Tobe signed the coffee-stained ledger and put some money on the counter, saying, ” You said you could be helpful. “
” Sure, buddy. But it’ll cost you more than that. I get a hunerd up front myself. For my services, you understand. “
” No problem, ” Tobe said and laid out more bills. The man looked down and then up at Tobe as if he hadn’t seen that much money in one pile before.
” Hell, buddy. For that I can get you a real high class whore. “
Tobe wondered what passed for “high class” in Piedmont, and said, ” That’s what I’m looking for. “
” I’ll give you the room at the far end. What time would you like company to drop by? “
” Say, about nine. “
” Nine it is, buddy. “
Tobe gathered up the bills, leaving enough for the room and the service fee.
” Hey, buddy. Where you goin’ with that? I’ll pay her. You can trust me. “
” I’m sure I can. But tonight I’ll have the pleasure of paying the lady myself. “
The room wasn’t exactly flea-bag material, but it was working on it. The air smelled as stale as the manager’s breath. The single window wouldn’t open and the air conditioner was about to end its feeble life. The bathroom looked as if it had been cleaned a week ago and the sheets replaced about the same time. Tobe pulled a bottle of whiskey from his back pack, poured a couple of fingers into a plastic cup and sat on the edge of the bed. He took a sip and once again considered what he was doing.
If this Pharaoh was into prostitution, as Redding had told him, the way to get information was possibly through one of his women, Tobe figured. It was likely that the woman being procured by the motel manager would have direct ties to Pharaoh’s mob. But even if she didn’t, Piedmont wasn’t all that big,and the women who practiced the “oldest profession” here probably knew each other and would have some knowledge of Pharaoh’s operations. That’s the game plan anyway, Tobe thought.
Then a disturbing thought hit him. Suppose the woman coming here tonight turned out to be Sheila herself? Was he ready to face her now? Would he be able to control the anger and pain he had been feeling the last few days? Remembering Sheila on the screen being degraded by those men and now the thought of her possibly being involved in nightly prostitution compounded Tobe’s despair. What kind of woman had she become? Did he truly want to find her and urge her to come back to him? Tobe took a swallow which emptied the cup. The liquor soothed something way down inside and suppressed both the hope and the hopelessness of his mission. He poured another drink.
Tobe found a mom-and-pop home- cooking restaurant down the road. He hardly tasted the food, but the noise of the place helped him relax. I’ll have another drink when I get back to the room, he thought. He was back in plenty of time and took the drink he had promised himself. He stretched out on the bed and was surprised he was brought out of a hazy doze by a light tapping.
Tobe got up and opened the door to early evening dimness. He couldn’t make out the woman’s features in the motel’s weak outdoor lighting, but he knew, with some relief, that she was not Sheila. He heard her say, ” Well, you don’t look like an ax murderer, honey. “
Tobe smiled and said, ” I haven’t used an ax on anybody in years.”
” A girl can’t be too careful, you know. ” She was serious, Tobe realized.
” You’ll be safe with me, ” he said. ” All I have tonight with me is a strong urge to fuck you, to put it bluntly. “.
” Say, I like the direct approach, ” she said lightly. ” I think we’ll get along. “
She turned and signaled to a car across the lot. It went slowly away, driven by a dark shadow. Was the driver one of Pharaoh’s mob, or even Pharaoh himself?
” Well, aren’t you even going to ask me in? “
” Was that your bodyguard out there? “
” Forget about him. It’s just you and me now, baby. “
She was about thirty-five, Tobe judged, a couple years younger than himself. She wore a fur coat even though it was warm outside. Clear glass earrings, not quite glittering in the dull light of the room, almost reached her shoulders. She had an abundance of dark hair which had recently had professional attention. Her eyes had too much make-up in an effort to make them look larger. Her nose was a trifle too prominent for her high cheek bones and her mouth was not generous. But her figure was good and her legs exquisite. Tobe thought she would turn heads whenever she walked into a room. She undoubtedly was what passed for “class” in Piedmont, Tobe decided.
” Aren’t you going to help a girl with her coat? You’re forgetting your manners, ” she said playfully.
” Excuse me, ” Tobe stammered. ” But I wasn’t expecting someone so attractive. ” And he meant it.
” Baby, you know just what to say. I have the feeling this is going to be a lovely evening. “
He took the fur from her shoulders and draped it over the back of the chair. Her dress was simple and black and low cut, showing off her large, well-proportioned breasts , which prompted Tobe to recall Sheila’s. Was this the handiwork of the same surgeon? The hem of her dress barely met the tops of her stockings held up by a garter belt. Again Tobe was reminded of Sheila’s black corset and garter belt in the film. He felt his excitement rise. She struck a pose and said, “Leonard said you wanted class. Is this classy enough for you, baby? “
Tobe felt that old warm churning inside that he hadn’t felt in well over a year. For an answer he went to her and roughly embraced her, putting his open mouth hard on hers. He tasted her open mouth and felt her body melt into his. He held her for a long time.
” I can see you’re not interested in preliminaries, and, my, you are pleased to see me, ” she said placing her hand over his growing hardness. ” How long has it been for you, baby? “
” Forever. “
” Well, we’ll have to make this a very special evening then, won’t we? You can call me Angel What shall I call you? “
“My real name’s Elwood, but my parents nicknamed me Toby, thank God. It sorta got shortened to Tobe.”
“Well, let’s get comfortable, Tobe.”
She helped him undress, letting her hands roam over his body and caress his cock with long, slow strokes. Tobe brought her to his nakedness and lost himself in her neck and hair. Angel pressed her thigh against Tobe’s hardness, her hands sliding down his back and then grabbing his ass. Tobe almost forgot what he wanted from this woman — information which would lead him to Sheila. He quickly put that thought away, far away, and pulled Angel’s dress over her head. “Let’s get you out of this,” he said.
He pulled down the lacy cups of her bra and fondled her large, firm tits. Angel drew her arms behind her and unfastened her bra, letting it drift to the floor. With her tits fully exposed, Tobe locked his mouth on one nipple, swirling his tongue around the sensitive tip.
“Oh, Tobe. You’re so gentle with me. I like that,” Angel said. But after a few moments she said, “You can use your teeth, Tobe, just a little.”
Tobe obeyed, taking her tender nipple between his teeth, teasing it with a slight pressure. He did the same with the other. With her free hand Angel kept up a slow, but incessant stroke on Tobe’s solid cock, brushing its head against the entrance to her pussy.
Tobe soon went to his knees and pulled her cunt to his mouth. Angel wore no panties and her cunt was shaved. With two fingers she spread her pussy lips apart. Tobe brushed her hand away and brought his tongue to her pink flesh.
“Yes, Tobe. You know what I want. Make me wet.”
Her voice urged him on. He grabbed her ass cheeks, forcing her cunt into his face, working his tongue and lips in and over its warm, smooth surface, making it slick with her pussy juices. Tobe’s fingers worked into the crevice of her ass and sought her ass hole, at first rubbing it gently, then entering its tender darkness. Angel cried “Oh!” and set her hips in motion as if she were being fucked standing up. Tobe felt her unsteadiness in her high heels, but he held her in place, tonguing and sucking her cunt. Then he got to his feet.
“No,” Angel pleaded. “Do me more like that. I was almost there.”
Tobe felt himself going a little crazy. It had been so long since he had had a woman, and this woman, this Angel, had a warmth about her which made his brief time with her more than just a casual fuck. Tobe eased Angel onto the bed, and she lay there before him, her hair now wild about her shoulders, her hips contorting to a rhythm only she heard, her large tits now reddish from his sucking, wearing garter belt and dark stockings and black stiletto high heels. An image of Sheila in her similar outfit flashed before him. He got on his knees and pushed Angel’s legs apart, then fell forward on his hands. He felt Angel bring her cunt up underneath him to capture his cock. He felt her hand bring his cock to her wet pussy and draw it into its warm recesses. Then he was completely gone.
He met every lift of Angel’s pussy with hard downward thrusts, forcing his cock deep inside her. She took his ear lobe between her teeth and then took deep bites into his shoulder which he hardly felt. He closed his eyes, rocking harder and faster. Their fucking seemed to go on and on. He was pleasantly surprised he was lasting so long since it had been well over a year since he had fucked Sheila.
Angel breathed “Oh, God!” and shuddered under him , bringing her hips up from the mattress and tightening her legs around his. Tobe felt himself responding; he could hold his climax no longer. He stiffened his arms and threw his head back. He seemed to thrust his cock even deeper into Angel. Then his whole body shook with three long, hot, wet explosions. In a voice which seemed to come from another dimension, he called Angel’s name, and not Sheila’s.
A little later Angel said,”I knew you would be just right for me, Tobe.”
“Is that what you say to all your customers?”
A cloud passed over her face. “I ought to slap your face for that remark. Your bedroom manners need work.”
“You’re right, Angel. Go ahead and slap me. That was completely out of line.”
“I forgive you. I’d rather kiss you,” Angel said as she positioned herself on him and darted her tongue into his mouth. Tobe kissed her for a long time, letting the warmth of her body blend with his inner euphoria.
“How long are you going to be here, Tobe? I’d like to see you again, and not in my -shall we say? – professional capacity.”
Tobe took a deep breath and said, “You may not want to see me again when you hear what I have to say. I’ve got to be up front with you, Angel. I’m not just a guy passing through. I came here to -”
“You’re looking for your wife, aren’t you?”
“How did you know?”
“A good guess. You mentioned to Leonard that your wife had left you. I think she’s probably a fool. But I envy her. I wish someone loved me so much he’d come here looking for me and take me out of this town.”
Tobe let that pass, and said, “I was hoping you could help me, Angel.”
“Help you how?”
“With some information you might have.”
“I see. Besides using me for sex, you want to use me for information. I’m not sure I like that.”
Tobe felt Angel’s body tense. “Maybe I’ve gone about this the wrong way. If I’ve offended you, Angel, I apologize. Will you at least listen to me?”
“I’m not sure I want to. Let me think.”
Angel gathered her clothing, dressed with her back to him and then reached for her fur. She came back to the bed and held out her coat. “Here. Be a gentleman.”
After Tobe had performed his duty, Angel said, “I’ve never had a naked man help me on with my coat. I think I like it. I think I like you. So I’ll listen to what you have to say.”
“Thank you, Angel. You mind if I put my pants on? I’m starting to feel a little embarrassed.”
“Not on my account, I hope,” she smiled.
Tobe stepped back into his jeans and sat on the edge of the bed.
“Three days ago a cop down in Ravensfield showed me a video of my wife Sheila, being — that is – getting it on with several men. He told me that one of them operates up here in Piedmont. His name is Teal Maggard, but he goes under the name of ‘Pharaoh’.”
Angel sucked in her breath and let herself down on the only chair.
“So that’s it. Your wife has become one of his women, one of his princesses. Tobe, Pharaoh is bad news. You’ll only get hurt going up against him.”
Tobe shook his head. “But that’s not why I’m here.”
“Doesn’t matter. You’re here to take away one of his women, even if she is your wife. He won’t stand for that. You’ll be lucky if you only take a beating. He’ll think nothing of doing away with you and dumping your body out of town. And he’ll get away with it. He’s connected in this town. Believe me, Tobe. I know what I’m talking about. I used to be one of those princesses — the blond hair, the big boobs, all of it. I never made a video, thank God. Pharaoh thought my butt wasn’t big enough.”
“But you got out.”
“Not all the way, as you can see. Besides, I’ve got protection now, the kind of protection Pharaoh respects.”
“The guy in the car.”
“He’s none of your business. And keep it that way. He’s a good man. If you cross him, you’ll have trouble coming at you from both sides.”
Tobe went to the back pack and came back with a photo of Sheila and him down at Barrow Lake the last summer they were together.
“Do you know her?”
Angel took a hard look. She shook her head.
“Take a good look,” Tobe urged. “Of course she’s blond now, wearing a lot of makeup.”
“You both look very happy. But I’m sorry, Tobe. I’ve never seen your wife. My friend got me free of Pharaoh’s paws more than a year ago.”
“Your friend sounds like he’s got his own connections.”
“I’d like to meet him.”
“That would be up to him.”
“What if you encouraged him to see me?”
“I wouldn’t. I don’t want him involved with you at all. You’re dangerous, to yourself and maybe to your wife. Get out of town, Tobe. I’ve changed my mind. I don’t want to see you again. And now there’s a little matter of money for my services.”
Tobe took out the wad of cash from his jeans. He had pulled out a good part of his savings. He had thought he would need it. When Angel counted the bills, she stood up and said, “This is a hell of a lot of money. Are you feeling sorry for me, Tobe? I don’t need anyone feeling sorry for me.”
“I’m still after information. For chrissakes, Angel, give me something to go on.”
She looked away and was silent for a time. “All right. Pharaoh used to do some filming and hold his parties for his political friends in an old closed factory that he bought and had renovated on the inside. It’s out on the old highway. I heard he hasn’t used it much lately. If you could get in there, you might find a clue as to where he’s keeping his women. I’m not doing you any favors by telling you this. You’ll probably just get yourself killed. And if I hear about it, I won’t feel one twinge of guilt I won’t be one little bit sorry. You understand?”
“Thank you, Angel.”
As Tobe opened the door, she turned and placed her hand on his cheek and brought his face to hers. He wanted the kiss to go on, but before he could get his arms about her, Angel broke free and said, “I lied when I said I wouldn’t be sorry. I wish you were here for me, Tobe.”
She turned and started for the black car which was parked where it had been earlier.
“One more thing, Angel,” Tobe called softly.
She stopped and turned.
Part 2: A Taste of Mango
I woke up feeling contented but a little disoriented. There was a warm body snuggling against my back and an arm draped over my waist, but I gave a start when I realized it wasn’t Matt’s. Something about the feel and scent fast-forwarded my mind through the events of last night when, too tired to face the drive home, I fell asleep in Nan’s arms.
It was hard to believe it had all really happened and I struggled to make sense of it. I should have felt ashamed and guilty about making love with another woman – and about walking out in the hall naked – but surprisingly all I could do was sigh and lace my fingers through hers. Nan was like no one I’d ever known, and waking up in her embrace felt so right! My romantic musings were cut short by the sound of a soft snore! A very genteel and ladylike snore, to be sure, but I had to suppress a giggle as reality rudely pushed idealism off the edge of the bed to fall clumsily on the floor. Smiling, I lifted our entwined hands to my breast and drifted back to sleep.
The next time I awoke, it was to the smell of coffee and frying bacon. The bed beside me was empty, but when I rolled over I caught a lingering whiff of Nan’s perfume. I was tempted to just go back to sleep, but the smell of breakfast and the need to pee got me going. My clothes were still in the living room, so I just pushed my hair out of my eyes and wended my way into the bathroom as I was. I didn’t even think to close the door – it was as if I were alone in my own apartment – so I was able to see Nan walk past and look into the bedroom, wearing an apron and nothing else. Apparently clothes were optional this morning and she looked so cute with her bare bottom framed by a ruffled pink apron. Well, guess I wouldn’t have chanced cooking bacon in the nude, either!
“Oh, sorry. Could I interest you in some breakfast? It’s almost done.”
“Sounds great. Be right out, Nan.”
Washing up, I caught sight of myself in the mirror and smoothed my hair back into a semblance of order before heading toward the kitchen.
“Hope you like your eggs scrambled ’cause I seem to have to have lost the knack for anything else here lately,” Nan said with a smile as she handed me a cup of steaming coffee and gave me a soft kiss.
“Mmmm, Sounds great to me!” We giggled and played footsie under the table as we ate. Afterward I helped her wash the dishes, feeling another twinge of guilt as I remembered the stack of dirty dishes cluttering my own sink. I gave a contented sigh when we had gotten the kitchen neat again and settled onto the living room couch with another cup of coffee.
“Got any plans for the day, Alyssa?”
“Oh, I really should go clean up my apartment, I guess. Seeing yours makes me acutely embarrassed about how bad I’ve let mine get.”
“Oh, come on. It can’t be all that bad!” She pushed on my shoulder playfully, then leaned over to look at me closely. “Alyssa? What is it?”
Before I could decide how much to tell her, she was on her feet pulling me up so quickly I almost spilled my coffee. “What . . .?”
“Much as I hate to say it, you gotta get some clothes on if we’re going go clean your apartment.”
“Nan, no! I wasn’t trying to get you to help me – I can’t let you do that!”
“I’m bigger than you, and around here might makes right,” she said as she dragged me over to my neatly folded clothes. She must have done that while I was asleep – I certainly didn’t remember doing it last night.
I didn’t feel like wearing the same pair of panties again so, since we were only going to my place, I just stuck them in my purse. I started to put on my bra, then smiled and put it in my purse, too. The feeling of my nipples moving under the thin top was as exciting as it had been last night – this could get to be addictive! I heard her moving around the living room as I brushed my hair and applied some lipstick.
She was zipping up a nylon carrying bag when I went in, noticing that she was wearing a short skirt, though not as short as last night’s, mid-heels and hose. “That’s not exactly a house-cleaning outfit, Nan.”
“Well, my French Maid costume is at the cleaners right now. Besides, what’s wrong with it? I’m dressed the same way as you!”
“Since this is all I have with me, I don’t have much choice! I’ll change when we get there.”
“Me, too,” she said with a smile and a wink.
I shook my head and went down to my car, undecided whether to be relieved or disappointed that we didn’t pass anyone along the way to see me ‘going bouncey-bounce’ as Nan called it. The sky was starting to cloud over.
“At least you picked the right day for it,” she remarked. “Doesn’t look like lying around the pool would be a viable option. Hey, whereabouts do you live?”
“Not far,” I replied, giving her the location of my apartment.
“Do you know that Indian food store in the little mall across from the park? Would you mind swinging by there on the way? There’s something I want to pick up – won’t take but a minute.”
“No problem.” I was enjoying the feel of the cool breeze coming in the window and lifting my skirt. It swirled around my legs and reminded me that I was pantyless in addition to being braless. “Listen, Nan, I have to apologize for my apartment. It’s really an unholy mess, and . . .” Her hand on my knee stopped me and I glanced over.
“And you’re ashamed and embarrassed for anyone to see it, because you’re usually a better housekeeper. Doctor Nancy diagnoses an acute case of depression, which will be a little less bad when we get finished . . . ‘Lyssa! Red light!”
I had been staring at her and not paying attention to my driving. The tires squealed a little as I braked at the last minute. “Sorry. How on earth did you know that?” I asked in a shaky voice.
“I recognized the symptoms – let’s just say I’ve been there myself. That look on your face earlier made it as easy as seeing red spots on your face and diagnosing measles. That’ll be ten dollars – you can pay the receptionist on your way out.”
The light changed and I headed for the store. “I’ve seen this place before, but never been in,” I commented as I parked.
“All kinds of neat spices, Basmati rice, frozen Samosas – come on in and take a look.”
I glanced down at my nipples, fairly visible under the tank top. Nan smiled and winked. “I think you’ll like it,” she said ambiguously.
An Indian woman in a sari was leaving the store as we walked down the sidewalk, and smiled as she held the door open for us. I felt my cheeks getting warm as I thanked her and stepped inside.
“Bouncey-bounce,” Nan whispered in my ear as we entered the store. It smelled like an Indian restaurant but even more intense and the shelves were loaded with colorful boxes, bags and cans, most of the labels in whatever language they speak in India – Hindi? Nan disappeared while I checked out the produce aisle and came back carrying a small bag. “Ready?”
As we were leaving, a clerk came over to ask if we were finding everything we were looking for, then began chatting about some things we might like to try. It was funny, because his eyes kept dropping to my bust, then snapping back up to my face. I was beginning to enjoy the attention and turned slightly to point to something on a shelf and gave him a profile view. Another customer asked him something, so we said goodbye.
“Well, it certainly looks like the girls enjoyed the trip!” she laughed after we got in the car, poking one of my hard nipples with a fingertip.
“Absolutely,” I confirmed, giving my breasts a quick squeeze. “Now I’m really gonna have trouble concentrating on my driving.”
My light-hearted mood evaporated as soon as I opened my apartment door.
“Well,” Nan said as she surveyed the living room and headed for the kitchen, “nothing here we can’t handle. Mainly clutter – grab a couple of garbage bags, then I’ll introduce you to my sure-fire method of beating depression while cleaning. The first step is mental attitude: take off your clothes.”
“Take off your clothes,” she repeated. “Everything’s more fun when you’re naked, even cleaning!”
Laughing, she grabbed my hand and dragged me into the bedroom. After stripping and hanging our clothes neatly in the closet, she stepped back into her pumps. “I prefer to wear heels when I’m cleaning ’cause it makes me feel naughty, but that’s optional. Next, always try to have something processing in the background while you work.” She lifted the overflowing laundry basket off the floor of the closet and started sorting clothes on the bed. “Why don’t you measure out the detergent and start the washer filling? We’ll do the permanent press stuff first.”
After a brief pause to watch Nan’s breasts sway gently as she bent over the bed, I stepped into a pair of my own low-heeled pumps and started the washer. She handed me the clothes basket, patted my fanny and disappeared into the living room. Just as I closed the lid, the sound of music in some language I didn’t recognize filled the air.
“It’s called ‘Ein Bisschen Frieden‘, German for ‘A Little Freedom’ – no, wait – that’s Freiheit. Maybe it’s ‘Peace’, I forget. We need some motivation, not to mention energy, and German music’s great for that!”
“You speak German?”
“A little, but mainly I just enjoy their music and don’t worry too much about trying to translate it. If you don’t care for it, just say so and we’ll switch to something else.”
“It’s fine – kinda upbeat but . . . unusual. I like it so far. What next?”
“The rules. You look at this and tell yourself ‘This is such a huge mess! I’ll never get this all cleaned up!’, right?”
“Uh, yeah, that’s pretty much it. Then I get more depressed and end up doing nothing.”
“I know. Think you could spend ten minutes cleaning? That’s all, just ten minutes.”
“Sure, but we can’t accomplish much in ten minutes. At least not without a bulldozer!”
“Set your oven timer or whatever for ten minutes, please, Alyssa. Now let’s see how much we can accomplish in ten minutes. Grab a garbage bag and and start tossing anything that doesn’t directly affect your life, health or finances! Feel the music and go!”
Getting into the spirit, I began swaying in time to the music and going through the stacks of catalogs, junk mail, empty Cheetos bags and so on. Since I always wore clothes, even when I was alone in the apartment, it felt strange to be completely bare – especially with someone else around. I was very aware of my unconfined breasts moving as I worked. When the buzzer sounded, the bag was almost a quarter full and there was a small area of counter top visible for the first time in weeks.
Nan reset the timer for twenty minutes, grabbed my hand and led me to the living room. When I started to talk about how much was still left to do, she shushed me. “We need to take your mind off the damned cleaning or you’ll talk yourself out of ever going back to it,” she muttered and used the ‘next track’ button on my CD player to skip a few songs. “Ganz In Weiss – All in White” she translated before I could ask. Taking my right hand with her left, she slipped her arm around my waist and began dancing to the gentle, lilting sound of a man’s deep voice. I rested my head on her shoulder and lost myself in the music and the familiar scent of Navy, the mess in the kitchen forgotten for the moment. The next song was by a woman, the beat a little faster. We moved into a sort of Fox Trot rhythm – Nan was an excellent dancer – and finished out the album. Lowering both arms around my waist, she leaned in and kissed me. The taste of her lipstick, the feel of her hands sliding over my hips, the pressure of her breasts just above mine all assaulted my senses as thunder rolled in the background and the drumming of rain on the windows filled the room.
When the timer sounded, it took a second to shift back to the external world.
“Time for round two,” she whispered in my ear as she gave my bottom a last squeeze and pulled away.
“Nan, I . . . “
“Come on. This is therapy, remember? Time to get back to to work . . . for ten minutes, anyway.”
The ten minutes passed in a blur, as did the next and the next, until the growling in both our tummies couldn’t be ignored any longer. “What do you have to feed your labor force, slave driver?” came her gentle husky voice.
“Not much,” I admitted sheepishly.
“Then I hereby declare a Pizza Emergency,” Nan said with a grin. “It’s the Universal Specific, you know. I assume you have the nearest pizza parlor on the speed dial of your phone, so what kind do you want?”
“Pepperoni, I guess.”
“My favorite, too. Why don’t you order us one, thin crust if that’s okay with you – my treat.”
“Half hour to forty minutes,” I reported after hanging up the phone.
“Good,” said Nan as she set the timer again. “Time enough for another round.”
“Now who’s the slave driver,” I complained good naturedly. Actually, I was quite pleased with what we’d accomplished – the permanent press was hung in the closet and my towels, jeans and such were nearing the end of their wash cycle. The dishes were in the washer instead of the sink and the junk from the counter, table and computer area was in garbage bags ready to be hauled off to the dumpster.
“Getting close to pizza time,” Nan announced as she looked up from scrubbing the stove top and glanced at the clock. “Do we want to get dressed or do what everyone on the Internet seems to post videos of doing, and answer the door like this?”
“Do people really do that?” I asked, kind of intrigued.
“Supposedly. I’ve seen several videos of it, though some of the viewer’s comments claim they were just staged, so I can’t say for sure.”
“What about you – have you ever done it?”
“No, but I have fantasized about it a time or three!” she admitted with a grin.
The idea was kind of interesting, the more I thought about it. I was getting comfortable with my – and her – nudity, and the thought of answering the door like this sent little ripples through my grey matter. Walking topless in the hallway last night had awakened something buried deep inside me I had never recognized before. Had it been there all along or was it just Nan’s bad influence? I looked at the smiling face of my Bad Influence and had to smile back. “Let’s do it!”
After wiping off the now empty table and setting out the Parmesan cheese and napkins, we touched up our lipstick and hair. “I can’t believe we’re actually doing this!”
“Me, either,” Nan confessed. “I’ve watched the videos and, well, gotten off imagining what it would be like, but now that it’s really about to happen . . . listen, Alyssa – remember that we don’t have to go through with it. All we need to do is have some robes or coverups handy in case we get cold feet at the last moment! This is more my fantasy than yours, and I don’t want to talk you into something you don’t want to do!”
I hugged her tightly and whispered, “It’s become mine, too, so don’t worry. But you’re right; it never hurts to have have a safety net, just in case.”
After some discussion, we decided we should at least put on our panties – ‘answering the door topless’ didn’t sound quite as illegal as ‘answering the door naked’, should someone complain. I had put two robes by the door and both of us were watching the clock, fidgeting like horses waiting for the race to start. I was scared and excited all at the same time; from terminal depression the day before, I was zinging through a whole gamut of emotions. I glanced over at Nan, whose parted lips and quick breathing echoed my own. She feels it, too, just like me!
The sound of the doorbell made us both jump. I glanced at Nan, crossed my fingers then looked through the door’s peephole, revealing a guy in his early twenties holding a pizza. I bit my lip. Last chance to back out. A second ring sounded. I went into the scenario we had discussed, opening the door a bit and peering out. “Oh – it’s the pizza already,” I said loudly, though it came out more like a squeak. “Sorry, didn’t expect you this soon! A friend was helping me clean house, and we’re not really dressed for visitors yet. Do you mind? If you want to wait just a minute, we can go get more presentable.”
“Not a problem, I’ve got other deliveries to make so don’t worry about how you look,” he said cheerfully.
With this unwitting endorsement, I took a shaky breath, thought about it one more time, then pulled the door open wide. Nan had moved to stand beside me, and the look in his eyes as they flicked back and forth between us raised my internal thermostat almost to meltdown level! I didn’t know what it was about standing half-naked in front a complete stranger that affected me this way, but my senses were working overtime as I reveled in the sensations that coursed through my mind and body like liquid fire!
“Whoa! You guys always do housework like this?”
“Not really,” Nan chimed in. “She’s always done hers in jeans and a baggy sweatshirt and I’ve always done mine completely naked. I’m trying to convince her it’s more fun that way, but this as far as I’ve gotten.”
“Definitely looks like fun, all right!”
“Well, I’m glad I didn’t offend you by answering the door like this. It feels kind of funny to be standing here talking to you while I’m practically naked, but to tell the truth, I’m really enjoying it!” I said with a smile.
“So am I!” he answered quickly. “Wish more of my customers answered the door that way, at least the good-looking women. You, uh, you have great looking breasts – both of you,” he smiled to include Nan.
“Thank you,” she dimpled. “I’m kind of proud of them.” Her hands trembled slightly as she lifted them and squeezed gently, causing her nipples to thrust out even further.
“Hey, I really do have some other deliveries to make, so I gotta run, but let me know when you convince your friend to do her housework in the nude, too, okay? I’d sure like to see that!”
“When I do,” Nan smiled as she took the pizza box out of his unresisting hands and reached for her purse, “we’ll order another pizza to celebrate and ask for you to deliver it. What’s your name?”
“Andy,” came the swift reply. “And, hey, this pizza’s on the house!”
Impulsively, I stepped over and gave him a hug. “Why, thank you, Andy.”
Moving away, I expected Nan to do the same, but she hesitated and he turned and opened the door. “Enjoy your pizza!” he said over his shoulder, taking one last, long look at the two of us before closing it.
We stood there grinning at each other like happy idiots, then Nan said in a shaky voice “Oh, Alyssa – that was so damned incredible! Don’t you just LOVE being a woman and being able to do things like this?”
For an answer I threw my arms around her neck, went up on tiptoes and kissed her with all the heat that had been building up inside me. Nan bent her knees, wrapped her arms just below my fanny and straightened. With my feet completely off the floor, I clung to her more tightly and devoured the inside of her mouth with my tongue. Thinking of what we had just done and the ‘forbidden fruit’ sensation of kissing another woman was sending little electric tingles throughout my body. I was more aroused than I’ve ever been been in my life!
Lowering me back to the floor, Nan’s hands moved over my back. Her fingernails traced down each each side of my spine before cupping my cheeks and pulling me tightly against her. “You’re hot as a firecracker down there, girl!”
“You feel pretty fiery in that area, yourself,” I replied as my hands clenched her firm butt and I leaned back, rubbing myself against her. The nylon of our panties made little swishing sounds that were barely audible above our breathing.
“Oh, ‘Lyssa, that was everything I ever fantasized it would be! I feel like I’m about to explode in a cloud of sparks! Um, would it bother you if I went into the bathroom and did something about it?”
*Special thanks to my wonderful friend Kristin for being my advisor and editor!*
“Really, Katherine, this wine is superb!”
Katherine Peterson poured more of the excellent wine into her friend Elizabeth’s glass. Elizabeth smiled appreciatively. She then poured Christina another glass too.
These were new friends of Katherine’s, they’d met through the same strange, marvellous boutique that Katherine had received her red high heels, purposefully made to arouse her Son, Alex, who she now fucked regularly. Tonight he’d chosen to go and meet friends and so, Katherine decided she would ask Elizabeth and Christina over. All three had been introduced by Ginette, the owner of the Boutique and they had become firm friends through chatting online.
*Swishhh* Elizabeth recrossed her long legs, sheathed in black Wolford stockings and dangled her black court shoe as she sipped the wine. She was in her fifties and head of an investment company. Divorced a long time ago she’d decided that younger men were to provide her sustenance in life. She was currently fucking a man named Owen in his thirties, a marketing manager with a wife to boot. However, they both craved Mother and Son roleplay and she provided him with that release. In return he was the best pussy-licker she’d ever met. Elizabeth brushed a speck of dust off her charcoal grey business suit and turned to Christina.
“So, how is Jeff getting on at University?”
By contrast Christina was a blonde, married housewife. She’d married young, but smartly and meant she could live a life of domestic luxury. She leaned forward, her legs encased in Oroblu shiny tan stockings and black heels, reflecting her smart black suit and skirt. Christina had harboured taboo desires about her Son for several years and last year ended up acting on them. Inspired by Ginette’s wonderful footwear naturally. Through a long process of teasing him, she’d snared her Son right under her husband’s nose. Now, when he was home from university, they fucked as often as they could while her oblivious hubby worked.
“Well, you know I went to see him, the other weekend? I booked us a nice little country hotel just a few miles from campus. It was very romantic, we pretended to be a couple!”
Katherine nodded appreciatively as Elizabeth took another sip of wine. Christina reached for her glass.
“He was so excited to see me, it was soooo cute! He got dressed up in a smart shirt and slacks, quite the good looking young man. All for his own Mother! Mind you, I was no slouch. Hair done, nails done, new lingerie from La Perla, golden heels – real boy-hardeners and, some new stockings from Ginette!”
“Oh, what pair?” asked Katherine.
“Golden Jocastas. Golden lace trim, with the word ‘incest’ sewed into the tops. His eyes nearly popped out of his head when I picked him up from the car park.”
“You gave him the flash?” asked Elizabeth, she had given plenty of boys the ‘flash’ too, that glimpse of stockingtop, that aroused their cocks and promised hidden treasures beneath.
“Oh yes! As soon as he got in the car I hiked my skirt up. I made him wait until we were driving out in the country before he could get his cock out. I almost blew him there and then!”
“You didn’t?” prompted Katherine.
“No… I made him wait, I wanted him to blow a big load with Mummy, seeing as how good I looked, so I let him wank while I drove but he wasn’t allowed to cum. He practically raped me when we got to the hotel room!”
“Mmm, yes,” nodded Elizabeth. “They’re so eager at that age.”
“He bent me over the dresser and fucked me like it would be his last. He screamed when he came in me.”
Katherine hummed understandingly “All those weeks away from Mummy though.”
“I know, I know. And I did send him all those phone pictures of my legs.”
“Oh that reminds me!” Elizabeth reached down to her handbag and fished out her BlackBerry. “Let’s see if Owen’s been a good boy… Ah yes!”
Elizabeth leaned forward with her BlackBerry and showed Katherine and Christina the screen. There was a picture of an erect penis, wrapped in a nylon stocking.
“He’s wanking into a stocking for Mummy while his wife sleeps upstairs. What a good boy!”
Katherine and Christina laughed as Elizabeth asked “Shall I call him now?”
Both of the women giggled and urged Elizabeth to call her ‘son’ and lover. She nodded and dialled the number. Christina and Katherine looked on expectantly.
“Hello, Owen… no, don’t say anything. Just listen to Mummy, got that? Now Mummy is very happy that you sent her the pic of your little winkie. It made Mummy want to touch her pussy too… But guess what? I am sat here with two of my lady friends… two naughty Mummys and they are watching, yes, watching. I’m fingering my pussy, skirt up around my waist, dreaming about having you inside me. You’d like that wouldn’t you, Son? Yes, being inside my velvet pussy, where you came from, pumping away inside Mummy…”
Katherine and Christina stifled giggles as Elizabeth spoke. The older woman winked at them.
“I bet you need to cum very badly now, don’t you? Well Mummy’s going to let you, cum in Mummy’s stocking, cum like you’re deep inside me… yes, that’s it, cum now, Son, cum for Mummy!”
And then, abruptly, Elizabeth pressed the Off button.
“He does like it when Mummy phones out of the blue, and gets oh so beautifully frustrated when Mummy hangs up suddenly. Good to keep them on the edge, dont you agree? ” she laughed as she put the phone back. “Now Katherine, what did you need to ask us?”
This time, Katherine recrossed her legs with a pleasing nylon *swish* as she collected her thoughts and smoothed her own cream skirt, that framed her black stockings. She took another sip of wine and began.
“I want to do something special for Alex. He’s been so sweet to me, he’ll be twenty soon and I think he would enjoy something different. The thing is I’m not sure what.”
Both women nodded and leaned back in their chairs. Christina then turned to Elizabeth.
“Are you thinking what I’m thinking?”
“I might be… I take it we’re thinking about our mutual friend?”
“Yes, I am.” Christina smiled at Katherine. “Katherine, what do you know about Janet?”
Katherine blinked. “Janet? Who’s she?”
Elizabeth grinned and put her glass down. “She’s someone who only comes out on special occasions. She’s what you’d call an alter-ego…”
Frowning Katherine reached again for the wine bottle and told the pair they’d lost her.
“Janet is someone you become, for your Son, on special occasions,” Christine explained. “She’s a sex goddess or a domme or a slut – it’s your choice – but she’s so totally different to the normal everyday you that your Son is surprised, aroused and devoted to you more than ever before.”
Elizabeth picked up the thread. “Janet allows you the opportunity to say or do things you might not have considered. Owen, for example, sets me little ‘Janet missions’. I wear an outrageously short skirt with stupidly tall heels and go and tease young men in bars. I then have to write an email to him explaining how humiliating and arousing it was. Of course, after I do it, I’m rewarded with the most gorgeous climaxes as he laps my pussy, over and over… But yes, that’s what it means to ‘become Janet’ something out of the ordinary.”
“When I’m Janet, for Jeff, I tend to dominate him. We wait until hubby is at work and then I text my Son and tell him Lady Janet requests his presence. He knows to crawl to my bedroom. Last time I greeted him like this-” This time, Christina held out her phone to Katherine. The Mother was dressed in thigh-high black leather boots with a spike heel, black stockings, a black corset. Her hair was a deep red. In her hands was a riding crop. “See? A completely different woman for him and as Janet I can do things with Jeff, that Mummy wouldn’t usually do.”
Katherine’s eyes were wide with surprise as she looked at the picture. “You- you look amazing!”
“And you all do this?”
“Ginette encourages Mothers and Sons to roleplay and experiment. She was the ultimate Janet. Three Sons, and she’s a different Janet for all of them. It’s amazing dedication.”
“And of course,” interjected Christina. “She has the shoes to match. You need to ask her for a pair of Janet’s Specials.”
“Oh yes,” said Elizabeth. “Very powerful sensations from those shoes, you’ll think things you never would have dreamed of. You’ll cum… well… let’s say like never before!”
Katherine’s pulse was now racing. Could she become Janet for Alex? What would drive him wilder with desire than he has ever been? What persona would be the best “Janet” for her son? Would it be to dominate him? He had loved it when she had gagged him during their emergency at that wedding. But be someone totally different?
She deliberated for a few days after her threesome drinks with Elisabeth and Christine. It was quite a big step to take, but one that sounded like a lot of fun too! However there was an unshakeable feeling at the back of Katherine’s head that told her she was going to go through with it. The lifestyle, making her Son so happy, not to mention making her own pussy as sated as it ever was. It was addictive. It was a powerful aphrodisiac and she wanted more. She wanted to continue.
Therefore, a week after Christine and Elizabeth had spoken to her, Katherine found herself back in Ginette’s exclusive boutique.
Katherine looked down at the box in her hand, her fingers ran over the nylon of the stockings that lay in the tissue paper. The touch shook something inside her, she shivered.
“Golden Jocastas,” said Ginette, perched on the edge of her desk in a black and white skirt suit, the skirt had a split in it that ended just below her hip. Her blouse was clearly a size too small. “You’ll forgive the classical conceit of the name, I couldn’t resist. The good news is your Son won’t be able to resist either. Here are the shoes.”
Ginette sauntered over to Katherine with a shoe box. She opened it for Katherine and showed her the contents. She gasped. “Wow, those are… very nice!”
The shoes were shiny, black leather peep toe heels. The heels themselves were tapered into a sharp point, four inches in length. The insides of the shoes were deep red and stitched on to the backs of the insides were the words ‘MOTHER’S HEELS’.
Katherine quivered at the site of them. So pretty and exquisitely made.
“Thank you, Ginette. These are something else!”
“You, my dear are going on a very special journey. Your Son is going to have such a special day! If only more Mothers were as considerate as you.”
Both Mothers smiled at each other and then Ginette leaned in and kissed her on the cheek. “Good luck,” she whispered.
That afternoon Katherine arranged to have her hair and nails done. When the receptionist had asked her a name she had paused for a moment and then replied “Janet Peterson”. The plan was set. She had booked a hotel room and sent a text to her Son. She had tried to be as brief as possible and simply told Alex he was to go to the Regal Hotel at 4pm, In ‘The Maitresse Suite’.
Katherine’s heart was pounding as she wheeled her suitcase down the corridor and towards her room. She hoped it would work, she hoped her Son would be happy. Taking a deep breath, she entered her key card into the lock and walked inside.
Two hours later and Katherine’s Son Alex was standing inside a lift at the Regal Hotel. He felt nervous and excited. His Mother had rented a hotel room for them both! There was something very naughty about the thought, like they were a couple having an affair, a dirty weekend away. His cock was beginning to harden at the thought of his sexy Mum in her lingerie when the lift pinged.
Alex stood in front of ‘The Maitresse Suite’ and coughed, he straightened his hair and knocked.
“It’s open,” came a voice from the other side. It sounded like his Mother, maybe a little deeper. Alex opened the door.
Inside the hotel room was a large bed, covered with soft satin sheets. To the right of the bed was dresser next to which was a fireplace with two chairs. The fireplace glowed and crackled. In one of the chairs sat Katherine, but Alex could barely recognise her.
Her hair was blonde, platinum blonde. It was curved into a perfectly straight bob just above her shoulders. Her lips coated in red lipstick. Her body was wrapped in a short, silk black gown, it’s long sleeves covered her arms. Her legs were crossed in front of her, encased in the sheer black of her stockings. On her feet were a pair of black, peep toe heels. Between her fingers, her nails long, sharp and red, she held a cigarette holder inside which was a black Sobranie cigarette. She looked Alex up and down.
“Oh my God, Mum…” Alex began. “You look… I mean, you’re smoking?!”
“Shut the door, Alex.”
Without even thinking about Alex did as he was told. He returned back to face his Mother. She looked amazing!
“I’m afraid Katherine couldn’t make it tonight, Alex. My name is Janet. I’m going to be your Mummy tonight.”
Alex looked confused and then nodded. Katherine- no, Janet, smiled, a wicked smile that caught Alex off-guard. His breathing became shallow.
“Strip for me,” she commanded.
He quickly unbuttoned his shirt and threw it on the floor. Janet continued to smoke the cigarette, elegantly pinching the holder, as she watched her Son strip down. He got down to his trousers and she crossed her legs. The sound of the nylon *swisshhing* made the blood rush to Alex’s cock. Janet put out the cigarette and flicked it into the fireplace. Alex pulled down his boxer shorts and his cock sprang out in front of him. Janet grinned at the sight.
“Come here,” she told him. Alex walked towards his Mother and stopped in front of the chair. “Hands behind your back,” she reached out and grabbed his cock. Alex let out a small yelp as Janet squeezed the cock between her fingers. “Just think, I made this. I created this. Naturally it should belong to me.”
Her hands moved down to his balls. Once more she squeezed. “These seem to be filling up nicely. Have you been thinking wicked thoughts, Son?”
“I- well I…” Alex didn’t quite know how to answer. He felt her fingers tighten.
“I see.” Janet stood up, in her heels she stood a few inches over her Son. Her hand moved back to his erect dick. “Come over to the bed.” She tugged at his penis and lead him slowly towards the bed, her gown billowing behind her. Janet’s heels click-clacked on the bare parquette of the hotel room. Alex shuffled behind as best he could. Janet sat down on the bed, crossing her legs once more. Alex quivered at the sight. She told him to fetch her cigarettes.
Alex did as he was told, still amazed to see his Mum smoking, but aroused by the action too. He passed them to her with an ashtray.
“Mum, are you really smoking, I can’t believe-”
WHACK! Janet quickly raised her heeled foot and smacked into Alex’s balls and dick. He immediately doubled-over and let out a groan of pain.
“Did I dare say you could question me?”
“No… no, Mum.”
“Get on your knees, Son.”
Alex quickly did as he was told, he didn’t want another high heel to his balls again. Janet leaned over and blew smoke into his face through her perfect red lips. Alex blinked as it stung his eyes. This made Janet giggle and taking another drag, she stood back up. Placing the cigarette between her lips she undid the cord of her robe. Alex looked up at his Mother as the robe came off. She wore a very tight, black corset that pushed her body into a classic hourglass figure. Her breasts looked magnificent and the corset ended in silver metal clasps that held the black stockings in place. The stockings had a bright gold band around them and Alex thought he could make out writing.
Janet moved her hips slowly from side-to-side. “You like my stockings, Son? Read what’s written on them…”
“It’s… ‘incest’, Mum. It says ‘incest’.”
“Are you the sort of wicked boy that thinks about incest, Alex?”
Janet pressed down one of her high heels into his thigh. “Do you think about incest with Mother, Alex? Do you?”
Her heel came away. “I see. Get over my lap please.”
Janet sat back down on the edge of the bed, stubbing out the cigarette. Alex moved towards her gingerly, but Janet was fast. She grabbed him, with strength she didn’t know she had and pulled his naked body down over her lap. She quickly clamped her nyloned thighs around his penis and squeezed. Alex gasped as the stockings touched his cock, the feeling was incredible, intense. All he could think about was humping his Mother’s thighs, but he tried to resist.
“I cannot believe I raised such a dirty little pervert!” WHAP! Janet’s hand cracked on to Alex’s backside. He yelped. “A dirty little boy whose cock gets hard at the sight of his own Mother!” WHAP! “I should have started spanking you the minute you started touching that dirty little prick of yours.” WHAP!
Alex tried to apologise, but all he could do was squeal, he needed to fuck, needed to cum! His hips began to gently buck up and down and the grazing of his cock on her thighs felt like ecstasy. Janet noticed his bum bouncing up and down and the thought of her Son getting himself off in her lap made her very wet and needy. She’d let him continue a little longer…
WHAP! “I bet you jerked off into Mummy’s panties, didn’t you? Or was it her stockings? Did you wrap Mummy’s soft, silky nylon stockings around your cock and make your mess in them?” WHAP! “Well? Did you?!”
Alex was now banging his hips against his Mother’s lap, his balls smacking against her thigh. His balls felt so tight, he was so close, he needed relief! “Yes, Mummy, I did! I did!”
Janet felt his body tighten and simultaneously opened her thighs and pushed her Son off of her. Alex collapsed by the side of the bed looking hurt. She wagged her finger at him. “No, no, you bad boy, you don’t get to cum yet.” She moved her legs apart even wider. “You know what Mummy needs. Crawl here and give it to her.” Her hands moved down her thighs and her red fingernails drifted over her steamy pussy.
Recovering from his fall, Alex crawled on all fours towards his Mother. His lips found the tops of her stockings, his head pushed against her thighs.
“That’s it, baby. Eat Mummy’s pussy, like a good boy should…” His lips found her sex. Alex began to lap for all he was worth, his tongue ran up and around her labia, finally flicking over her clit. Janet groaned with deep pleasure, her whole body was on fire, it felt incredible. “That’s it baby, show your Mother the respect she deserves. Show her how a Son should behave, pleasuring the Woman that loves him most in the world, giving his adoration and devotion to her. Ohhhh yes, my darling, lick Mummy harder, be a good boy and lap at her, make her cum!”
Alex’s hands gripped his Mother’s thighs and pushed his mouth firmly against her cunt. She leaned backwards, waves of enhanced pleasure pushing her body in different directions. The cum was growing inside, yearning to be set free, to engulf her body. Her fingers clawed at the bedsheets. Alex renewed his eating of her pussy, pushing and lapping and flicking with his tongue.
“Oh fuck yes, make Mummy cum, be a good little pussy eater and make her fucking cum oh–OHHHH, SHIIIIT!” Janet cried out, screamed even, as the climax ripped through her. She grabbed at Alex’s hair, holding him to her pussy for as long as she could. Expletives, pain, pleasure, she coloured the air blue as she came, it was overwhelming. She pushed Alex’s head away and collapsed backwards on to the bed.
For a few minutes, Mother and Son lay in the hotel room, wrapped in ecstasy and astonishment. Alex had never heard his Mother climax like that before. Janet lay on the bed stunned, stars in front of her eyes. Alex’s hands drifted back to his cock. He began to masturbate, hoping to relieve some of the intense pressure in his balls. It was then he felt something cold and hard on his cock. Opening his eyes he saw his Mother’s high heel pressing down on him. She was sitting on the edge of the bed once more. Her other heel joined the first, trapping his cock between the two shoes. Alex moaned as Janet began to lift the shoes up and down his rigid prick.
Doctor Carmen Monroe looked down at the eighteen year old boy who was contentedly licking her stockinged calves and grinned. It had been all too simple to get Josh, a teenager who had been living with depression during his teenage years, to submit to her will. She sat back on her therapist’s couch and watched the naked young man worship her legs with his tongue. Moments earlier she had watched his young cock spurt all over her and now she wanted more.
“Feels good, doesn’t it, Josh?”
Josh Maven looked up at his therapist, resplendent in her lingerie, stockings and high heels. He felt truly alive, kneeling at this MILF’s feet was the most exhilarating thing he’d ever done in his young life. He nodded at her quickly.
“Up higher, please, kiss my thighs.”
The teenager responded instantly, kneeling up higher, his hands slid down her silky thighs, he began to plant little kisses along her stockinged legs. Carmen let her fingers snake around Josh’s hair and pulled the boy towards her. She wanted his lips on her pussy, hers would be the first he would ever taste.
Spreading her thighs wider, Carmen leaned back and closed her eyes. She felt incredible, the burning in her loins was so intense, that she wasn’t going to need much to send her over the edge, even an untrained tongue could be of good use. When it came to pussy-licking, young men were like dogs. Very little clue what they were doing but bags of enthusiasm. Her own son had been the same…
“You’re going to eat my pussy now, Josh. Just push your mouth against my panties and start licking.” Josh moved ahead a lot slower now. He was nervous, Carmen could tell. She widened her thighs a lot more and pulled his head in. She felt his tongue furtively begin to probe her pussy. “Lick it!” Carmen hissed. Josh increased his laps, grazing his tongue against the wafer-thin material of the Agent Provocateur panties.
Carmen began to moan, the previously cool blonde therapist leaned back and revelled in the pleasure of having the young man between her legs. His tongue touches, uncultured, but effective, sent shivers up her spine. It was the eagerness that Carmen craved, full of stamina and need. He was lapping at her pussy with such ferocity she could feel each tongue lash throughout her body.
She told him to keep going. Encouragement was important, he would need to grow to love this, learning to worship was key to the development of any young man, especially if his Mother was going to enjoy him too. The thought of incest shook Carmen to the edge of orgasm, she squeezed her thighs together, ready to ride out the wave of pleasure that was crashing towards her.
When Josh’s tongue grazed over Carmen’s clit for a final time, she squeezed her thighs together hard and trapping his head between her legs as she groaned in ecstasy. She rocked back and forth, her fingers in his hair “Good boy, good boy…” she whispered.
Rolling her head, relaxing in the dizziness her orgasm had caused, Carmen slowly relaxed her legs and let Josh come up for air. “Stand up, Josh.”
The young, naked man did as he was told. Carmen pulled on his cock, pleasingly noting it was hard once again. Taking hold of it his throbbing member, Carmen stood up in front of the lad. In her heels she was a few inches taller than he was. She smiled at the power she currently had over him. “This cock belongs to me, understand? The only other person who’s allowed to touch it is your Mother.”
“But-but I,” the boy stammered.
Carmen put her finger on his lips. “Shh, little one. Your cock belongs to me and your Mummy and trust me, she will touch it. Now your turn to lie on the couch.”
She let go of the hard cock and Josh slid down and onto the couch, lying on his back. Carmen stood over him and reached behind her to unclasp her bra. “You see, Josh, I like young cock and enjoy making it my own. My husband is an unimaginative bore and I like to set my fantasies free…”
The therapist threw the unclasped bra on to Josh’s chest. He gasped at the wonderful breasts that bounced in front of him. “Mmm, I can see your happy out that…” Carmen knelt down, putting her beautiful breasts in line with Josh’s erect cock. “Don’t think I’m a bad person, Josh, I’m really not, I simply know what I want… and when my own son got to be eighteen, I knew I wanted him too.”
Josh’s eyes widened with surprise at her admission, as Carmen leaned forward and pressed her breasts against his cock. As he moaned, Carmen began to slowly tit-fuck the young man, kneading her tits up and down his prick. “Yes, Josh, I seduced my own son. He came to worship me, he still does, in the same way you will too. I’ve been waiting for the right cock to come along and when I met you and your mother I knew…”
The boy continued to groan with delight at the tit-fuck he was receiving. Carmen grinned. “The thing is Josh, your Mother, who has put up with so much raising you, deserves your respect, she deserves to be worshipped. She just doesn’t it yet. And I know you, you want to serve, you want to worship her. It’s all perfectly natural, Josh. Most mothers ignore this desire in their sons, which I believe is foolish… Everyone like to be pampered, why not exploit. The way to a boy’s heart is through his cock, eh, Josh?”
He moaned as pre-cum began to leak and splatter over Carmen’s globes. “So here’s the deal young man, you will obey me, completely unquestioningly and in return I will turn your Mother into the woman you want her to be: sexy, commanding, loving but authoritative, a woman who you respect, please and fuck.”
As Carmen had predicted, the thought of Josh fucking his hot, dominant Mother was too much for the young lad who proceeded to spunk uncontrollably. Carmen pressed her tits together tighter as his young cock splattered across her gorgeous globes. His cock throbbed as the last splatters of cum jerked from the red cock.
“There, that’s better isn it, Josh?” Carmen pulled her cum-covered tits away and smiled at the boy. She began to rub the cum into her tits. “The best thing will be hugging my husband when I get home tonight, knowing my body has been covered in boy-cum. Now up you get, Josh and then kneel down.”
Josh, still dizzy from his cum, did as he was told. Carmen stood up in front of the kneeling boy. “You will go home tonight, but you may masturbate but you may not cum. Understand me? No cumming, unless I say so.” He nodded. “Now you may show your appreciation for our little session today, kiss my shoes.”
The boy bent forward and began to plant kisses on her black stilettos. Carmen felt her pussy tingle once more, this had been a delicious evening and better yet, she had broken another boy.
It had gone nine o’clock when Josh had returned home and Diane had left several messages with Carmen to explain just why he had been so late. The concerned mother was beginning to wonder who was more in need of therapy, her or her son. This is idea of Doctor Monroe’s about using her own body to control and make her son happy just seemed so absurd! Yet Diane’s other feeling, the guilty twinges she’d been having were caused by another reason – she was enjoying the notion that someone, albeit her own son, found her sexually attractive.
When he came home she was sat on the sofa, dressed in comfortable jogging bottoms and sweatshirt, eyes flicking between the TV and the clock. Josh had been very quiet when he eventually got home. She had tried to engage him in conversation, but it was clear he wasn’t interested. He mumbled something about ‘having talked’ and then scurried off to his bedroom.
Diane wasn’t impressed, how dare he stay out this late, visit his therapist and then not pay her any attention?! She went to bed annoyed with her son and Dr Monroe. She shouldn’t be left out of this!
Then Diane had another thought, this time about her appearance. She had been showing off her legs to her son when he had done something positive and that was giving good results. Maybe he just needed a little more encouragement?
That morning Diane decided to have another chat with Josh. She picked out an outfit that she had no intention of wearing to work, but simply to see her son. The black skirt ended mid-thigh and nicely showed-off her legs, she’d decided on a pair of black stockings to enhance the effect. Her blouse was tight on her, showing a little cleavage. On her feet she wore a pair of patent black stilettos with three inch heels. Looking at herself in the mirror she nodded, let’s see the little bastard ignore me now!
She click-clacked in her heels down the landing loudly. She wanted him to hear her approach. Diane flung open her son’s bedroom door.
Josh scrambled for his duvet to cover his nakedness. He was clearly startled, but not fully awake yet.
“M-Mum? What’s wrong?”
Diane strode into the room. His eyes were glued to her. She stopped in front of his bed and put her hands on her hips.
“I want you to tell me what happened between you and Dr Monroe last night.”
Josh tried to keep his breathing under control. He nodded slowly. “We just talked…”
“Just about me, my likes, dislikes, that sort of thing.”
The mother changed weight on her legs, pushing her hips out. She folded her arms.”And what did you tell her, Josh?” She looked down at Josh, was that a bulge underneath the duvet?
“That I like women… come on, Mum, this is embarrassing…”
“Well I pay for these sessions, Josh, I think I’m entitled to know what goes on.”
“Of- of course, Mum.”
“OK, good… well as long as we’re clear.”
Mother and son looked at each other, the atmosphere in the bedroom was imbued with electricity. They could both feel it.
“I’ll be going to work in a bit. The kettle’s on if you’re interested…”
Diane turned on her heel and strode back out of the room, this time quietly shutting the door behind her. She felt dizzy, her heart beating fast. She leaned back against the door, her palm pressed against her chest. Then she heard the slapping noise, the one she heard at night. He was masturbating! Shaking her head, Diane quickly began to walk down the stairs. Her pussy was becoming moist, moist for her own son…
Hi everybody! This is one of the many stories I’ve written over the years. I’ve decided to clean them up (read: edit the heck out of them) and start sharing them. This one has some light-femdom, a pretty willing husband, and a few fun surprises. Enjoy!
Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor did he realize how eagerly his wife Stephanie would embrace the idea of feminizing her husband. How far would they go?
Chapter 1: “Loren’s New Genre”
Loren Candéze sat on his couch reading the book he’d purchased from the internet. He laughed. His wife Stephanie, who sat on the other end of the couch reading a magazine looked up. She brushed her platinum tresses back over her shoulder with a wave of her hand and ran her red fingernails through the layers of her hair.
“What’s so funny, Loren?”
Loren held up his electronic reader. “This!”
“I guessed that much, dear,” she said and smiled.
He chuckled. “Sorry. It’s this story I’m reading. Cindy called me the other day—”
“The same. She said her firm had done a study of what types of books people were buying these days. It sounds like political thrillers are dying out, so she wants me to try another genre.”
Stephanie raised an eyebrow. “And what genre is that?”
“That’s the funny thing. You’ll never guess what’s selling right now?”
She closed her magazine, slid her feet out of her wedge-heeled slippers and pulled her legs up beneath her on the couch. “Romance?”
Loren smiled. “Sort of.”
“Give me a hint.”
“Ok, it has to do with what you’re wearing.”
Stephanie furrowed her brow. “You’ve lost me, I have no idea.”
Stephanie looked stunned. “As in guys in dresses?!”
“Let me see if I’m hearing you right. Your agent Cindy, a very nice respectable woman who owns a minivan, wants you to write stories about men who dress like women?”
“That doesn’t begin to describe it.” Stephanie folded her arms. “Are you considering this?”
“Sure, why not? I don’t care what I write, I just want to make money.”
Stephanie frowned. “I’m not sure this is a good idea.”
“For one thing, what are we going to tell people at parties? ‘Here’s my husband Loren, he writes stories about men who dress like women.’ I would die of embarrassment!”
“We don’t have to tell people.”
“This could ruin your reputation if it gets out.”
“It won’t get out. I’ll use a fake name.”
They sat silently for some time as Loren watched his wife process this information. She seemed opposed.
“Is the money really that good?” she asked.
“Cindy’s memo says it is. She also says she’s got a publisher lined up who is waiting for all the stories I can write, so I’m guaranteed to get this published. Something I’ve never been with my thrillers.”
Stephanie smiled slyly and scrunched her nose. “There’s not something you’re not telling me here, is there?”
“Like you’re going through my closet when I’m at work?”
Loren laughed. “No. I’ve never worn women’s clothes, even at Halloween.”
“And you’re not going to suddenly start wearing my clothes, are you?” she asked cautiously.
“No, of course not.”
“This is just about money?”
She seemed assured. “I guess it’s up to you, but it still doesn’t sound like a great idea if anyone finds out. Your reputation as a macho thriller writer will be finished.”
He shrugged his shoulders. “Like I said, I’ll write under a nom de plume. I’ll be Jessica Chambers.”
“No, you’re not using my last name.”
“Fine, I’ll think of something.”
She quietly shook her head and returned to her magazine. Then she set her magazine down again. “Wait a minute. You always tell me, ‘only write about what you know.’ If you’ve never worn women’s clothes before, as you claim, then how can you write about it?”
“I’ve never skydived before or smuggled a gun into Albania either, but that’s what I wrote about in my last Louis Rock novel.”
“Was he wearing panties when he did it?” she asked with a wink.
“Ha ha. Seriously though, I don’t need to be a crossdresser to write this stuff, I just have to do research. I’ll read some of the books to see what others are writing and I’ll fake it. And if I need to know something about women’s clothes, I’ll ask you, my expert.”
“What makes you think I’ll help?”
“Because you’re my wife and you want me to succeed. Because when I get rich and famous. . . or at least rich, then we can spend all our time on luxury vacations.”
She cooed. “I do like the sound of that.”
“I knew you would.”
A mischievous glint appeared in her eye. “I’ll tell you what, I will help you out.”
“I knew you would.”
“Tell me about this story, the one that made you laugh.”
He picked up his electronic reader. “This?” He laughed and shook his head. “It’s total garbage.”
“Well, for starters, the characters are ridiculous. Listen to this:
“I was the world’s most macho man until my wife got through with me. Now I’m a simpering sissy. This is the story of the horror that happened to me. Five years ago, I was the world’s most macho man. My name was Mr. Brandy Highheals.”
“Can you believe that? The writing is awful. There’s no subtlety. It’s repetitive. It’s contradictory. On the one hand, the writer’s trying to tell you the guy is some macho archetype, but his name is actually ‘Brandy Highheals,’ spelled with an ‘ea’ instead of an ‘ee’? What kind of garbage is that?”
Stephanie smirked. “Can I say something?”
“I’m not pointing this out to criticize or anything, but your first name ‘Loren’ is the same as the girl’s name ‘Lauren,’ it’s just spelled differently. And your last name, ‘Candéze’ often gets transcribed on shipping labels when I order something over the phone as ‘Candies,’ which are a sexy little form of women’s shoe. So while you laugh at poor Mr. Brandy Highheals, you are similarly afflicted: your name is pretty darn close to Lauren Candies.”
Loren scowled at his wife. “What’s your point?”
“My point is this isn’t as unrealistic as you make it out to be.”
“Really?! Ok, listen to this. The author goes on to describe our super-macho hero Brandy. He describes him as 5′ 2″ tall and weighing all of 109 pounds. He also has size six feet and shoulder length hair.”
Stephanie smirked again. “No, I agree. That’s not a normal male and certainly not a macho one.”
“I’m glad you recognize that.”
“But let me point out that not all males are hulking, muscular giants. In fact, you and I are about the same size.”
“I am not that small,” he said defensively.
“Yes you are, dear. If you lost 20 pounds, we could easily share a wardrobe.
And I can prove it.”
“Easy. Let’s go see if my clothes fit you?”
“Don’t be such a little girl about it, Loren! If you want to write about men who wear women’s clothes, the least you can do is try some on. . . who knows, you might even like it?” She fought to contain a smirk.
Loren folded his arms and shook his head.
Stephanie laughed. “Chicken?” Loren looked uncomfortable. Stephanie knew how to push Loren’s buttons and calling him a coward was the biggest button in the whole set of button. “Come on, dear. No one will know.”
“I’m your wife, I’m allowed to know these things. Think of it as research.”
They sat in silence for several seconds as Loren struggled with knowing that he should take her up on this offer and yet fearing being seeing in women’s clothes. Then it hit him, he was already learning part of what he needed to know to write these stories. His fear of being seen was something he could use as a basis for writing his first story.
“Ok,” he finally agreed. “I think this could be valuable research.”
Stephanie set the magazine on the coffee table and slid her feet back into her slippers. “That’a girl, Laura!”
To his surprise, Loren felt a tingle rush down his spine and his penis swell when his wife called him by a feminine name. This was going to be an interesting experience.
Chapter 2: “Laura Is Born”
A couple minutes later, they were in their bedroom. Stephanie sat at her vanity table looking through her makeup as Loren sat on the bed. He was naked except for a white cotton robe he’d covered himself with after Stephanie told him to strip.
“Since this is only for one night. . . I presume,” she said, winking at Loren.
“Yes, one night only,” he confirmed.
“. . . then I won’t make you shave off your body hair. But normally, no self-respecting woman would ever slide on hose if her legs were hairy and she certainly wouldn’t allow a hairy chest. Of course, your chest isn’t that hairy, but still.” She flipped through a jewelry box. “If this were longer term, I’d also make you get your ears pierced, but there’s no reason to do that just for tonight.”
“Thank God for small favors.”
“Don’t get smart with me, young lady!” she laughed as she pulled a pair of clip-on earrings from her jewelry box. She turned to Loren. “Ok, I’m ready.”
“Can’t wait,” he said sarcastically.
“Now you’re sure you’ve never dressed up before?”
“Not even a pair of panties?”
Loren rolled his eyes. “Not even.”
“Ok, then let’s start with the basics.” She handed him a pair of pink cotton panties. They weren’t particularly ornate as they had no lace, no bows, and no ribbons. Indeed, they weren’t designed to be anything but functional. But they were panties, and they were pink, and Loren felt extremely funny holding them. For a moment, he didn’t know if he could slide them on or not. Part of him wanted to, but part of him felt sheer terror.
Loren took a deep breath, shifted uncomfortably, and then slowly raised his right leg to slide his foot into the panties.
“‘atta girl!” Stephanie said and patted her husband on the head. She pushed his arm away to get a clear view of his penis. “Yep, still there. . . and excited too!”
“I didn’t think it was going to fall off,” he said.
“You sure acted like you did,” she countered. “Care to explain the excitement?”
Loren shot her an annoyed look but didn’t speak. Instead, he stepped his left leg into the panties and pulled them us his legs. As he did, Stephanie went to her underwear drawer, where she retrieved a pair of tan pantyhose. Next, she grabbed a floral housedress from the closet. The dress was off-white in color with a red, black and green flower pattern, a square collar which exposed several inches of shoulder blade and a loose hem which stopped just below the knees. Stephanie laid the housedress on the bed next to Loren.
“You want me to wear that?” he asked apprehensively.
“Unless you want to walk around with your thingy sticking out,” she said condescendingly and she returned to her vanity table. She picked up a pink lipstick. “Pucker up, dear.” Loren did as she asked and she painted his lips. Next, she clipped the earrings onto his ears. They were one inch long silver drops. They felt very heavy to Loren as they tugged on his earlobes.
“None of this is permanent, right?”
“Sure it is, dear. It’ll never come off. That’s why women have to reapply it each day,” she said sarcastically as she applied eye shadow to his eyes and blush to his cheeks. “Don’t be such a baby.” Next she grabbed a pink bra from the vanity. It matched the panties. “This is a big moment dear, your first bra!” She giggled as she attached it behind his back and showed him how to bring the straps up over his arms. She stood back and looked at her work. “Hmm. Something’s missing.” She snapped her fingers. “I know!” She walked over to her underwear drawer and grabbed a handful of panties. She folded these and padded the bra with them until Loren had small, budding breasts.
“Aren’t these a little. . . uh, large?”
“No, not for a girl. They’re barely an A-cup, if that.”
“They look way bigger.”
“Mine are C’s, and you think those are too small.”
“No I don’t, honey! Your breasts are great!” He moved to kiss her, but she stopped him.
“Don’t smear the lipstick, dear.”
“Spoilsport,” he said.
She grinned at him and handed him the pantyhose. “To put these on, roll them up until you can put your toe straight into the end. Then pull them up your leg to your knee. Slide in the other foot. Then pull the whole thing up to your waist.”
As he pulled the pantyhose up his legs, Stephanie couldn’t help but notice his erection, which had escaped the panties, bouncing up and down in his lap. He was excited, even if he refused to admit it. She was getting a real kick out of this herself, much more than she expected when she maneuvered Loren into agreeing to let her dress him up.
“So what happened next to Brandy? Tell me about the wife?”
Loren struggled to pull the pantyhose up over his erection. “Oh, she’s a frustrated Amazon. She’s five-nine—”
“Seven inches taller than her macho husband, huh?” Stephanie scoffed. She and Loren were the same height, but in her heels she was often a good deal taller than him, something she liked to rub in now and then because she knew it bothered him.
“Yeah. But she’s got insane measurements. She’s 105 pounds and has double ‘D’ breasts, which Brandy keeps wishing were bigger.”
“Clearly, he knows nothing about breasts. What do we know about her?” She picked up the reader. “Oh, this is good.” She read:
“Before she became my wife, Candi was my high school sweetheart. When I single-handedly won the state championship as quarterback and captain of our football team, she was the head cheerleader cheering me on. So were the other cheerleaders too, if you get my drift. She cheered me on too when I single-handedly scored 45 unanswered points to win the state basketball tournament. I was the captain of that team too.”
Stephanie laughed. “That’s pathetic.” She kept skimming the story. “Looks like she’s big on miniskirts and tight tops. Wow, she wears five-inch heels to lounge around the house!”
Loren smiled at his wife. “If I have to play Mr. Brandy tonight, then you should play Ms. Candi.”
“No can do, girly, I don’t have any heels higher than four inches and I only wear those on special occasions.”
“This is a special occasion, go strap ‘em on!”
Stephanie rolled her eyes, but went to her closet. She was enjoying this too much to stop just yet. She removed her robe and slid a tight white mini-dress over her shoulders, smoothing it down her hips and thighs. Then she slipped her feet into her kidskin, four-inch high-heeled, open-toed, slingback pumps. The red polish on her toenails showed through the tan stocking she still wore from work. “I hope you appreciate this,” she said as she returned to her vanity. She looked at Loren’s intense erection beneath his pantyhose and giggled. “Yeah, you’re appreciating this all right!”
Loren covered his erection with the housedress, which he now unzipped so he could slide it over his head.
“So how does poor Brandy end up getting all gussied up?” she asked.
“I have no idea, I hadn’t gotten that far.” He was having problems working the tiny zipper.
Stephanie picked up the reader and skimmed the story. “Hmm. He actually does it to himself.”
“He was a crossdresser the whole time?”
“No, he claims this was the first time. He gets all upset at his wife, goes into a diatribe about how men are men and women are gross and that he’s not a sissy. Then he storms off to the bedroom where he sees her panties. For reasons he can’t explain, he slides those on. They feel so good he tries on a blouse and then a pair of her six-inch heels.” She shook her head. “Six-inch heels? This is ridiculous!”
“I told you. Is that when she catches him?”
She kept reading. “Nope. . . oh goodie!” She looked at her husband and smiled. “Since we’re re-enacting this book, I get to catch you jerking off with my panties!”
He furrowed his brow. “Uh, no.”
“Come on dear, you’re hard enough. In fact, you’re so hard I’d be afraid your little guy might explode if you don’t relieve the pressure. Why don’t you give it a couple tugs? I won’t tell anyone.” She smiled mischievously and he didn’t know if she was serious or not.
“Your loss. Why don’t you finish getting dressed.”
Loren slid the floral housedress over his head and stood up so Stephanie could zip him up. His penis stood at attention, even though it was beneath the pantyhose. This caused the dress to tent out.
In her heels, Stephanie stood four inches taller than her husband, so she looked down over his shoulder at his erection. She chuckled. Then she looked at their height difference and chuckled again. “We need to get you some shoes, shorty.”
Loren felt his erection pulse. It always humiliated him whenever she reminded him how short he was because he felt it was unmanly to be smaller than his wife. Tonight, however, the humiliation came with a new sensation: excitement. In fact, the excitement was so strong that for a brief moment he wanted her to say it again. This shocked him. Why did he want his wife to humiliate him? Where had this come from? He wasn’t sure.
Meanwhile, Stephanie walked over to her closet. In her four-inch slingbacks, her hips rolled sexily from side to side as she walked, which excited Loren tremendously. As she bent down and picked up a pair of shoes he wanted so badly to go over and rub her body. But he stayed put.
Stephanie rose and held the shoes up for Loren to see. They were tan, patent leather pumps with a small open toe. They had two-inch heels. “I think these are good starter heels for you. They’re pumps, not sandals, so they give a lot of support. Also they have a real heel, so you can experience walking in heels, but they’re low enough you should be able to master them pretty quickly.”
“Yep. A girl’s best friend. And best of all, you’ll still be shorter than I am,” she said happily. “I like my sissies short!”
There was the excitement again. As she said this, his penis pulsed in the panties. It felt like it could explode at any second. This confused him. Part of him wanted to tell his wife to stop making fun of him and to stop treating him like her own personal toy, but another part craved the electric shock her words gave him. It surprised him to realize he actually seemed to wanted her to humiliate him. He didn’t know how to handle this.
Loren took the heels and sat down to slip them onto his feet as his wife stood next to him. “How hard can this be?” he asked rhetorically. He found out when he stood up. It took him a moment to gain his balance, though everything seemed ok. But then he took his first step and nearly fell down.
“Seeeexy!” said his wife and she whistled.
He looked away from her. “Do you mind, this is hard enough as it is.”
She reached out and patted his penis through the floral dress. “So it is,” she purred.
“Stop that!” He pushed her hand away and she giggled.
She folded her arms. “Look dear, it’s simple.” She put one hand on Loren’s stomach. “Stomach in.” Then she put the other hand on his back. “Chest out.” She lifted his chin with her thumb. “Head up. Don’t look down.”
“How can I see where I’m going?”
“You can’t, you have to plan ahead. Now, when you start off, you need to keep your feet together. Pretend you’re walking on a tightrope. Take little sissy steps. And when you step, point your toe, but bring your heel down first. Let the sole of your shoe follow quickly and smoothly. Then make sure your foot is firmly planted before you lift your other foot. Balancing on a thin heel takes some practice.” She demonstrated with her own heels.
Loren took a deep breath. “I can do this.” His first step was graceful. His next two weren’t.
“Whoa!” she said. “Do what you did with the first step, just do it slower. Now swing your arms as you walk, like this.” She demonstrated how he should move his arms.
A series of stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me!
It really is difficult to believe. Out of such chaos and misery could come such bliss. The misery was quite a while ago now, that fateful day when I arrived home devastated. That afternoon old Gilligan had called us all in, the whole sales team. The company had decided to restructure and we were out. All five of us. Out on our ears, with immediate effect.
“The weekend starts now,” he had said. “And don’t bother coming in Monday.”
Sacked, at my age. OK, the other four guys, none of them was over 25 but me, well, I was ‘over the hill’ at 35, certainly in this trade, what chance would an ‘old man’ like me have of finding another job? Certainly not in Hackfield. Most cities may have two or three other possible businesses where I could use my skills but not Hackfield. It was Gilligan’s firm or nothing.
I had to hand in the keys to the company car, and take the bus home. What indignity. Walking down the road towards the house I wondered what I was going to tell Leslie. But it didn’t matter. I called out as I opened the door – no reply, maybe she was visiting someone, even shopping perhaps. I opened the door to the lounge. And yet more disaster, the ultimate disaster I had always dreaded, faced me.
There strewn across the floor, were my clothes. Not my suits, my sweaters, pants. My ‘other’ clothes. My dresses, bras, panties, and my makeup bottles and tubes and my shoes and my padding. Leslie had found them. Obviously. Hell, and my photo album. They were ruined, all ruined. The dresses were torn or cut, the tights were ripped, the make-up was all in a big bag, tubes opened, everything smeared and mixed up. My shoes had been broken, all the heels had been hit with a hammer or something. And my breast-forms, my prize dressing item, they were cut and pulled apart. Un-usable, the lot.
And in the middle of all this mess, in the middle of the lounge, was a letter. Addressed to ‘Mike – or – whoever – you think – you – are’. I opened the envelope. Loads of cash fell out, all in fifties and hundreds. I counted them, several thousand. What the heck?
I looked again, there was a letter.
‘Mike. You disgusting pervert. So this is where all our money has gone. Here is exactly your half of what we have left. Get out of my house before nine o’clock or I’ll use my half to pay someone to beat you so senseless. How could you, you bastard? L.”
No ‘love from Leslie’, obviously.
I looked again, she had torn several sheets out of the photo album. All showing me in varying states of undress, usually with really tarty make-up, shoving one of my dildos or something else similarly shaped up my ass.
This was it. The end. I had three hours to get out. I could do it of course, grab a couple of suits and so on and go. But go where. And then do what? No job, no wife, no house – it was hers, inherited from an aunt. I just sat there and felt very sorry for myself. Finally I knew the only way out. I walked back into the hall and opened the small drawer by the phone and took out my gun. I went back into the lounge, sat on the floor surrounded by the remains of all my finery. I put the barrel into my mouth and pulled the trigger.
It clicked. That’s all, it just clicked. Then I noticed the ammunition clip was empty. I checked in the drawer again, she had not left me even that way out, she had taken it. I sat down again in the middle of the lounge floor and looked round. It was not all there. All the stuff I had hidden in the loft was there, all in tatters or ruined.
But – a small ray of optimism. My new tart’s outfit stuff wasn’t. I’d left it in the garage, well out of the way behind some old tools so that I could get at it that weekend. When Leslie had been due to be at her mother’s, when I had been going to dress up really sexy and do disgusting things with my new maxi-dildo. I’d got all the stuff out of the loft – maybe Leslie hadn’t found that.
I rushed into the garage and pulled the tools out of the way. The two bags were still there, untouched. I dragged them out and into the house and up to the bedroom. It was at that point that I think I became rather mentally unhinged. I remember everything I did but I can’t for the life of me explain why.
It was because a single realisation came to me. No job, no house, no wife. Nothing. In a way I was free – suddenly – from convention. Heck, I’d just tried to commit suicide, that was certainly unconventional. My thought processes seemed logical to me though I do realise now I was definitely unhinged. I seemed to be moving automatically. In the bedroom I stripped. In the shower I smeared Leslie’s depilatory cream all over my body and watched my light brown body hair sink down the plughole. I’d always thought of removing all my body hair but I had always chickened out, afraid of what Leslie might say.
I dashed back into the bedroom with the bag and pulled out the new breast-forms I had bought from one of the bags. Totally unrealistically I had wanted, in the privacy of my own house and alone, to show the biggest pair of boobs I could possibly get away with. By that I mean which I thought I would look good in, me with my slightly warped and twisted mind. Which is why the breast-forms were a little on the large side. I had measured them earlier, I thought I’d end up with 48-DD boobs. Not just big, but very big.
I unwrapped them and smeared the adhesive over the back, then lay back for a few minutes to allow them to adhere to my chest. I thought I had better put a bra on while I was still slightly lying down so that standing up wouldn’t put too much strain on the adhesive. I had my silver 48-DD bra ready.
The next hour seemed to fly by, again I remember absolutely everything I did but have little real idea of the thought processes which went through my head. But I have an over-riding image in my head, at the end of that time, of sitting on the stool in the hall, looking into the long mirror there, and trying to dial the phone with my long nails. Long vermilion nails that is, a deep bright red color and long, nearly an inch longer than my own. Totally impractical but I still have the memory of extreme satisfaction in wearing nails which went with the rest of my ‘look’. Over the top, that was the idea.
I looked so very over the top. I had never been of the opinion that I could make a convincing woman when I was dressed. Too tall for one thing, just six foot. OK I know there are quite a few women that tall but they are mainly sensible, very few have a penchant for stiletto pumps with six-and-a-half inch spike heels. I did. As I looked in the mirror I liked what I saw, even more than I had done in the past. The shiny black patent pumps showed off my long legs well, as did my sheer black seamed stockings. As I sat there listening to the dial tone for a few seconds my eyes moved upwards in the mirror, over my long sexy legs, past my knees, across the smooth acres of thigh exposed by my too-short skirt. I smoothed my stockings, revelling in the experience as I watched my red-tipped fingers oh-so smoothly sliding across my nylon-covered flesh.
“Er – hi there. Can I have a taxi please? Yes, as soon as possible. Yes, that’s right”.
I gave the girl on the line my address, placed the receiver down and waited. I knew the taxi firm quite well, Leslie and I had used them a few times. They were quick, the girl on the line had said less than ten minutes, I knew she would be right. I stood up and looked again into the mirror, my gaze continuing to scan upwards. Past the high hemline of my tight black leather micro-skirt, past the tight silver top which hugged my figure closely and showed it to best effect.
And what an effect. The tight top over my bulging tits, the low cleavage revealed, I was delighted with the results of the ‘make-over’ on my chest with the new bulging boobs, the smoothness of the surface covering the edges where the breast-forms met my own skin. I looked carefully, I just couldn’t see the join. I had ‘real’, massive, tits! Wow!
I remembered a comment from the assistant in a trannie shop where I had once gone for a make-over – Harriet, I think her name was. I had tried to get her to tell me just how good I did look. She had been reluctant, then I realised she hadn’t wanted to lie but didn’t want to put off a potential customer. Finally she had come clean, basically saying that I was too tall and had the wrong sort of face to be really mistaken for a woman.
Maybe sitting down she had said, and certainly not in daylight. I had thanked her for being honest, she had finished by telling me to keep away from high heels. I almost told her ‘I’m a transvestite – I can’t', but I didn’t say it.
As I heard the taxi pull up outside I glimpsed my legs again in the mirror. So much for Harriet’s advice! I checked my make-up once more. The long smooth blond-ish hair, the very carefully over-made-up face, I liked what I saw. Obviously. I had gone too far with the make-up but that had been deliberate. Quite heavy over my face, black eyeliner, thick false eyelashes with deep coal-black mascara. I had even shaved off my own eyebrows and replaced them with careful application of eyebrow pencil. The full effect, offset by thick gold hoop earrings, a wide gold choker, three bracelets, five big heavy ‘gold’ rings on my fingers. I looked good. But then I would think that wouldn’t I?
Just for once I didn’t care if any of the neighbours saw me. This was to be my final exit. Outside my front door for the last time, I checked in my purse, id cards – well, maybe I should keep them. Make-up, Leslie’s letter and the cash, keys. Keys? Wouldn’t need them. I took them out and posted them back in through the letter box of the locked door. Finished. Michael was finished. I turned and strode proudly out to the taxi, head held high, chest thrust out, boobs bouncing, boy did that feel good!
I looked at the taxi-driver, his mouth was open at the sight heading towards him but he didn’t drive away. I opened the door and got in.
“OK” I said, thrusting a fifty note at him. “Drive.”
He did. As soon as we got out of the street and round the corner I leaned over towards the driver’s compartment and in as sexy an impression of a female voice as I could manage, which was probably not very female at all, I told him to drive me to the truck-stop just outside Hackfield, on the northern side of the freeway.
I couldn’t see his face but I did hear a grunt from him, a rather disdainful sound. He knew what was going on. I know now why I had chosen that particular place though at the time I really was still on autopilot, just reliving out a fantasy without really considering any sort of consequences. I’d seen a report in the local paper about that place, it had been raided by the cops a month or so earlier and several trannie hookers had been arrested there. Trannie hookers? Well, now that could well be me.
It was getting dark when the taxi pulled in outside the truck stop there. I handed the driver a fifty and beamed at him saying ‘Thank you darling’ in a rather silly high-pitched voice. Totally unconvincing. He sneered at me and drove off. I turned. I pushed open the door – and I went in. I stood there on the threshold and looked. There were about five or six men in there. They all turned to look at me. I froze.
I heard the door close behind me, heard the grating squeak of a badly-oiled hinge, and shivered at the noise. I ‘woke up’. Came out of my reverie or whatever it was. Suddenly I was awake, totally, more awake perhaps than I had ever been in my life. I looked round. Hell!
The guys in there were all looking at me. Not surprising really considering what I looked like. I could just about see my reflection in the plate glass at the side of the truck stop. It was really getting dark outside, the reflection was quite clear. And what did I look like? A trannie, that’s for sure. Far too tall and too well-built for a woman, I was sure absolutely every man in that diner was looking at this totally tarted-up transvestite in disgust. So how the hell was I going to get out of this? How was I going to get out of that diner alive?
I shivered again. There was no way I could run away. The taxi had gone, I was on my own. I just had to, in some way, brave it out. I had never really thought of myself as having courage but it must have taken some nerve to do what I did next.
I walked forwards towards the bar, remarkably steadily considering my skyscraper heels. Looking back I am amazed I did it. My very first outing dressed up. And here I was, strolling down between the tables. It did feel good.
All sorts of emotions washed over me. The main one was simply pride. I was proud of myself. Proud of the way I looked. Proud of being, in some way, a woman. What the hell, I knew I looked like a man in a skirt. A pansy, a poofter, a fag, a guy tarted up, a caricature of a woman. But I loved it. Even the leers from the truckers in there, they began to cat-call as I approached the bar. As a guy I had been average, middle of the road, a nothing really. But as a woman, like this, I was something even if the closest words to describe me were probably ‘trannie slut’
“Well hello there, gorgeous.”
I stopped. I shook. The guy sat at the bar had just spoken to me. He was looking straight at me, at ME! At the slut right in front of him! I smiled rather weakly and took a deep breath, in some way feeling my massive fake tits swell out as I did so. He noticed that! I moved forward again, more confident in my ultra-high heels now, and slid my tightly wrapped bum onto the stool next to him. I sat up tall and proud and enjoyed yet again that wonderful feeling I had experienced so often in the privacy of my own kitchen as I slid one nylon-encased leg over the other.
“Well hello there honey” I purred in as provocatively sexy a voice as I could manage.
I heard myself and thought there and then ‘That sounds pretty good – Michelle’. Michelle? Well, or course. Like many TVs I had chosen a name a little similar to my original name. Michael? Well, right now I was obviously Michelle.
“And what do you call yourself, little lady?”
I heard the mocking mutterings from the other five or six guys in the diner, not very loud but loud enough for me to hear.
“Lady – huh!!”
“Little lady, what a laugh!!”
“Little, that he isn’t, not with those tits eh?”
I tried to ignore them and turned back to the guy who had asked me.
“Michelle” I said, not muttering now, much more clearly, much more confident.
And very daringly I reached out and laid my right hand on his. What the fuck was I thinking about? Well, to this day I really don’t know. That ‘madness’ which had taken me over was still there to some extent. I was still not in total control of my actions, going through the motions of being a trannie slut without really realising it. I was oblivious to the consequences, just acting out a fantasy without thinking about it. Fantasy, yes, I got a real thrill as I looked down and saw my own somewhat feminine-looking hands, extra-long scarlet fingernails and all, caressing that guy’s own big gnarled hands.
“And what do they call you, lover?”
Had I really said that? The tittering and cat-calling carried on behind me but this time I didn’t look. Autopilot or not, I was still enjoying myself.
“I’m called Big Mack” he said.
The noise behind me increased, it sounded much more than the few men I knew were really there.
“Hush up you all!” called out Mack, looking past me at the ‘crowd’.
Suddenly it quietened.
“Well, Michelle. I reckon after what happened in here last week you’ve got some guts and I’d like to buy you a drink. How about it? I’ve been on the road for two weeks now and I ain’t getting any and my old woman’s prob’ly shacked up with the bastard from the store she works at. All I’ve done is jack myself off ev’ry night for two whole weeks so I reckon I deserve some. And since there ain’t no others queuing up for me, honey, I reckon you may well do me just fine.”
At which, to my total amazement, Big Mack moved his hand away from mine and slid it up my leg, from just above my knee until it was so nearly sliding up under my micro-mini. I shivered. Hell, I shook visibly, this was SO amazing, I just couldn’t believe it. Had it happened at last? Had I – got myself a man?
“Hold on Mack.” A voice came from behind me. I was about to turn when, out of the edge of my view another man, almost as wide as Mack, moved between us. “Let’s find out what this ‘girl’ is out for. I heard about last week too, the trannie guy was asking twenty dollars a suck and got greedy when somebody wanted to fuck him. So how much is this big tart charging?”
I looked at him, then across at the other four men behind him, still sat, hardly eating, intent on the events unfolding in front of them. They were all, well, nearly all, well built guys. Apart from Mack and this guy, one of the others seemed tall, two of the others were shorter but all of them were big and wide except for the tall skinny guy at the back. Any one of them, except maybe him, was quite capable of beating me to a pulp if he wanted, indeed probably any one of them could kill me with his bare hands. I smiled at the big guy.
“So honey, what’s your name then?”
“He’s Fat Jack” butted in Mack. “Hold your horses, Jack, I’m first. I can see your snake is getting excited already bit you can wait your turn, I’m first.”
He turned and spoke to me, again putting his hand on my leg and this time sliding it just a little up under my skirt to reveal my stocking tops and a hint on my bare thigh. I looked down between Jack’s legs, then at the same area below Mack’s belt and realised. These guys were all excited. Both their cocks were getting larger. And I had done that! Whatever else happened, had done this, got these two men aroused and in all likelihood the other guys too.
“Well Mack, I’m not greedy. Not for money anyway. How about buying a girl a drink? A gin and tonic and then I’m yours.”
Mack didn’t need to be asked twice, he looked towards the guy behind the counter who moved quickly and then put the glass down in front of me. He raised an eyebrow at Mack, then went back and came back with a large bourbon which he handed over to Mack.
“Cheers” I said, smiling, raising my glass towards Mack and drinking deeply.
I was ready for that. I usually drank beer, never was too hot on harder liquor, but this time the G and T seemed more suitable. Mack took over half of his double down in one go and then reached over to touch my neck ever so gently, though he wasn’t so careful when he slid his hand down and over my ‘breasts’, and then had a feel down in my cleavage.
“Now, darling, take your time” I cooed, trying to look and sound sexy.
But Mack was not so keen to wait, he was aroused and in something of a hurry. He squeezed my right breast and got up off his stool, reaching to grab my right hand and drag me after him towards the corner of the bar. Not private, not secluded, but not quite so on display as we had been sat up at the bar.
I was new to this but I had fantasised about it so often that I knew the drill, or at least I knew one version of it, the one I had read about in so many stories and dreamt about so often. It started with a kiss. I was ready for that as I sat down next to Mack and his big meaty hand settled yet again on my thigh, this time sliding up even further than before. He looked down sat my exposed stocking tops, at the garters holding up my sheer seamed stockings, and groaned.
“Christ. Michelle or whoever you are, you do sure as hell turn me on. I haven’t felt so horny in years. Come here!”
I was kinda ready for anything at that stage, but not for the ferocity of Mack’s advances. Within seconds he had pulled me on top of him and grabbed my ass close to him so that my tiny thong and my bulging ass-cheeks were exposed to the world. Or at least to all the other guys who had moved up closer to our corner so they could watch. Mack buried his face in my neck, nuzzling me hard with his lips and his unshaven chin, then pulled my top away from my shoulder to reveal my very ample and well-filled bra cups.
“Jeez you do make one helluva woman” he moaned as he tried to slide a hand inside to pull out my bulging tits. “You sure smell like a tart should, I’ve seen some trannies in my time but honey you do sure take the prize. Heck, I need to get my monster out.”
Mack had to heave me to one side, he was none too gentle with me, to try to unzip his pants. Not that I was ever in control of the situation but at that moment he definitely was, I decided that I needed to in some way assert my ‘womanhood’. I leaned and nibbled gently in his ear, noticing the traces of bright red lipstick I was leaving there.
“And you, my darling,” I murmured “You are one helluva man. So, lover, let me help you there.”
And I did! I really did! In the corner of the bar, with half a dozen other guys watching me, I reached out and pulled down the zip of his pants, surprising myself at how well I did it despite the scarlet 2″ nails which I was wearing.
I slid my fingers in and grabbed his bulging cock, pulling it free. Mack sighed with relief that it was freed from its prison. I could see it now for what it was, the very first man’s cock I had held other than my own. It was only about 6″ long and not really very thick. But it was my first. I felt so proud, I just had to lean down and tease the very tip of the bulging cock-head with my tongue. The taste was really something, I had expected it to taste salty in some way, I was rather surprised at the creaminess and the texture of his pre-cum.
But I wanted more. I pulled at his pants and then at his shorts so that the whole lot, his cock and his swelling scrotum, were exposed. And more than that, available. I was really not too sure exactly what Mack had in mind so I set to it quickly, fondling his balls and sliding my red-tipped fingers gently along the whole length of his exposed cock. I looked up.
Mack himself was lying back against the bench, eyes closed, with a look of extreme contentment on his face as I traced my fingers back and forth. I looked round. All the other guys in there were staring. And Fat Jack was at the bar, looking over, and had his own cock out, he was wanking as he watched us going at it.
“Mack, my darling. What would you like me to do now? I only want to please you, my lover. Do you want to fuck my mouth? Do you want me to suck your cock, squirting your gorgeous cum down my throat? Is that what you’d like, honey?”
Had I really said that? Wow!
“Oh please–” Mack groaned, and pushed my head downwards.
I had no choice – I slipped my rich red lips over his swollen dick. I encircled the bulging head with my tongue and began to tease it, and to move it round with my tongue. Soon I couldn’t move it round, it almost filled my mouth. With my left hand I stroked his shaft harder, and with my right hand I squeezed his balls ever so gently, all the while sucking him hard and looking right into his eyes. I kept on sucking and he kept on swelling in my mouth for several minutes, then he grabbed my left ‘tit’ and began to groan loudly. I couldn’t say anything, my mouth was full!
And then it happened, the inevitable. All this time I had been terrified someone would come into the truck stop, a cop maybe, checking up on the place again. But no-one came, no-one interrupted us. And I could tell, I’d been there, done that, that Mack was ready. But the speed with which he reached his climax surprised me. One moment I was happily sucking on his bulging cock as it moved around just a little in my mouth. And the next – well! It was alive! Of course it was. But it really did seem to take on a life if its own, bucking and thrusting and pulsing deep in my throat.
The pulsing was totally amazing. It just shot and shot, what seemed like gallons of hot thick sticky cum, the cock-head was so deep in my throat I couldn’t really taste a lot at first, it just shot straight down my gullet. I was determined not to let ‘my sex’ down, to prove I could give head as well as any other woman, I really did need to show what I was capable of. I clamped my lips tight on Mack’s cock all the while as he was cumming, shooting his load into me, fucking my mouth, swallowing hard as it poured down my throat and into my stomach.
“Michelle, fucking hell, that was fucking brilliant”.
That was all Mack said as I slid my mouth off his shrinking erection. I looked at him, he was spent. He was just lying back on the bench. Moaning. Sweating. Pleased with himself. And, from the smile he was giving me, pleased with my performance too. I was thrilled. I had satisfied ‘my man’, performed up to scratch. I wasn’t really sure why, it just felt good. It was not until quite some time after that very first experience that I finally understood why.
But I didn’t have time to ponder on the philosophy of being a woman at that time. Fat Jack was walking in my direction. And walking rather unsteadily too, his cock was already out, he had probably been playing with it for quite some time and the results were obvious. And it was BIG! So much so that with his pants and shorts open and that thing sticking out he couldn’t really walk properly. He limped in my direction.
“OK you cock-sucking faggot. My turn now!”
I looked across at Mack, he almost seemed as if he was going to say something in my support, to say something against the insult which had just been thrown in my direction. Insult, yes, but I would have had to admit that it was true. Mack had recovered enough to speak up a little
“OK Jack, go on, if you think you are man enough” he said with a wide grin across his face.
“Man enough!” called out Fat Jack. “Just you wait, I’ll show this big trannie slut what a real man can do!”
“Don’t say I didn’t warn you, Jack, she’s a hell of a performer. Hold onto your balls when she gets going, I’m telling you, she could suck paint off a wall.”
Well, in a way Mack was ‘defending’ me. He had said ‘she’ – every time he referred to me. But I didn’t have time to think about that, Jack was already there, his cock facing me as I sat there, it was only inches from my mouth. His huge cock. I just looked up at him and smiled. I breathed in to swell out my ‘tits’, slid out a very long nylon-clad leg towards him so that he had to touch it, to grab it, to hold it. And his hand just had to slide along the smooth nylon. As it did so I was watching his huge cock, it jumped, it trembled.
Jack was excited, despite all his talk about ‘faggot’ and so on. He wanted me! And I wanted him. Already I was an expert on men’s cocks. This was my second. I reached a hand up to his bare hairy arm and slid my fingers gently along it, then deliberately dug my long red nails in just a little. The cock in front of me jumped again and a glob of pre-cum began to ooze out. My head darted forward, my lips enveloping the whole of the huge head, my tongue sweeping the juice down my throat. And I began to suck.
There wasn’t time for any foreplay this time, Jack had been starting to wank for several minutes already and was nearly there.
“Christ, you faggot, that feels good. Oh yes, go on, grab my balls. YES! Oh my…. YES!! Oh Michelle, I’m … I’m …. Cumming now, oh Jeez.”
Within thirty seconds he was. I swallowed the huge erection deeply, or as much of it as I could fit in my mouth, as he pumped hot sperm straight down my throat. It felt just as full as Mack’s had, and lasted about as long, thrusting and pumping while I tried to swallow. And then, even more quickly than in Mack’s case, it subsided as it emptied. And again, there, lying back on the bench beside me with a self-satisfied grin on his face, was a happy man.
I got up and walked over to the bar.
“I think I deserve another drink, don’t you?” I asked the guy behind the counter.
“Sure you do” he said, quickly getting another large G and T and setting it down in front of me. I took a small sip. “And – do you want a job?”
“Yeah. Tending bar here, in the evenings. I can pay you well. And you can charge a fortune for what you just did, you could clean up. I bet loads of guys will come in here to get a load of that. You could make a fortune in tips, I guarantee it.”
A job? As a barmaid? Hell, why not? I had to do something. OK I had a pile of cash in my bag but that wouldn’t last forever. The logistics would take some thinking about – where could I live? And I’d need a lot more clothes, ordinary things like skirts and bras and pantyhose – and flatter shoes of course.
But how would I live? As a guy most of the time, just changing for work, or as a trannie, or – dare I think it – as a woman? Heck no, I couldn’t be convincing enough, I did know that.
“I’ll think about it” was my reply. Then something else came to mind. “Where’s the john?”
“I think you’d better use the Ladies” suggested the bartender with a smile. “Just through that door over there. Don’t get so many ladies in here.”
His smile widened. I was tempted to grin back but I decided not to, I was going to play it straight, carry on the pretence of really being a woman. I slipped down off my stool, wriggled to straighten my skirt, and teetered across and into the Ladies’ john.
I was surprised when I went in. I knew that the men’s equivalent in that place wouldn’t be very clean, load of guys in and out all day, some of them not so clean or careful. But this one was different. It was painted a pale lemon color for a start, very sweet smelling, and spotlessly clean. I managed to pull up my skirt and sit on the can and do what I needed, despite my very long nails. Then, sat at the small vanity in there, I re-did my make-up a little, ending with a wide bright slash of fresh lipstick. I was ready again for the fray. Then another thought came to my mind. I slid up my top and managed to remove my bra. I stuffed it into my purse, rearranged my top and undid three more of the buttons down the front.
I looked at my reflection. Yes. Even more than before, I was dripping sex. NOW I was ready for more as I as I wiggled back into the diner and across to the bar. One of the other two guys was sitting there, next to my drink, looking eager.
“Hi there honey” I whispered in his ear as I lifted myself onto my seat next to him. “Ready for some action?”
I was surprised at my bravado but I had taken a break and really did want more. He had obviously decided not to take too long over this, his hand went straight away to my tits. Within seconds I had his pants open at the front, I reached in and pulled out his swelling cock. And within minutes I was revelling again in the thrill of a pumping cock shooting his cum deep down my throat. Another guy satisfied. I looked round for number four, he didn’t look so keen. He had been watching everything, and playing with himself, but didn’t move at all in my direction.
Maybe I would have to work on this one? Maybe I would have to seduce him, convince him to let me into his pants? I stood up and thrust out my boobs, it must have been obvious I wasn’t wearing a bra anymore. My massive mock tits still stood out proudly. The bartender had yet another gin ready for me, rather foolishly I took it down in one.
“Hi there lover, how about a quick blow job?”
“Harlot!” exclaimed number four.
I must have looked startled.
“Don’t worry about Preacher Joe, Missy. You’ll get nowhere with him”
I looked round, it was Big Mack who had recovered from his experience. He grabbed me and slid both his big hands round my boobs and buried his mouth in my neck from behind.
“Come on Missy, I’m up and ready again, that suck was so good for me, how would you like a good fucking? My snake is hot and hard, how about me coming up your ass?”
Fucking? Heck, could I? Surely not, the three blow jobs had been totally sensational but could I cope with Mack’s organ up my ass? Of course I could. I was tempted to turn round there and then, to pull up my skirt and down my panties. But no. What about Preacher Joe? I couldn’t let him defeat me, it hurt my ‘womanly pride’ to be spurned like that. I grabbed Mack’s hands and pulled them away.
“OK handsome but wait your turn. Right Joe, what about it?”
With those words I walked up to Joe again, opened my legs and sat across his thighs with my black nylons exposed, with my tits right in front of his face. He stared. He was sweating. He gave in. Within three minutes, still spouting obscenities and insults, he was shooting his load into my waiting mouth. And there was just one guy left.
I stood up yet again and looked across at Mack who was still there, waiting, playing with his cock.
“Hang on lover, one more yet” I said with a smile, looking across at the tall thin man still sitting with his coffee.
“Come on Little Big Man” called out Mack. “Come and get seen to quick. I’m getting hot and hard and I’m ready fer this lovely lady. I need it up her ass!”
The thin guy stood up hesitatingly. He looked worried but I didn’t care, I was going to have him. As I passed the bar I took another drink of the gin I’d left there and swaggered across to him, swinging my hips and bouncing my boobs.
“Little? Big? Which are you honey, let me come and see.”
This guy seemed different. He was the only one you could really call handsome. He wasn’t as stocky as all the other four or the bartender. Well muscled, yes, he was wearing a tight short-sleeved shirt which revealed a very nice figure. I wondered what I would find ‘down below’. I got closer. Heck, he really was handsome. I could play this one differently. Be his girl before sucking him off. Be just a bit romantic, if I could.
I reached ‘Little’ and reached up to put my arms round his neck, noticing that he reacted automatically, he slid his hands round my waist. Suddenly – I wanted to kiss him. I looked him in the eyes.
“Come here my darling, come to Michelle” I cooed.
I could see his face looking at me clearly. I felt a hand squeeze my waist, I did so want to…. I stretched my head towards the guy, my lips just touched his…
I heard big Jack’s voice.
“Whoa there, Charlie, seems to me you’re not taking this seriously. This ain’t some woman to kiss and cuddle and take your time with, if you’re not going to do this fucking trannie slut right you’d better move over mate, let some real men back into her!”
I felt someone grab my arm and pull me away from ‘Charlie’, then a shout from behind me. As I turned I saw something glisten and looked round at Charlie, his arm was still round my waist, I saw his face – he looked angry. This time it was him who spoke.
“Hold on Jack. And the rest of you fuckers. You’ve had your turn and I reckon this little lady’s done right by all of you. Now it’s my turn. Just ’cause I ain’t into a quick suck and blow like the rest of you wankers don’t mean I should miss out. So back off – ‘less you want to make something of it!”
Then I noticed, the bright flash of reflected light I had glimpsed, Charlie was holding out a switchblade, pointing it towards the other men who were backing off. I was amazed, they were fighting – over me! And Jack wasn’t backing off.
“Wait up Charlie, this ain’t some gorgeous blonde you might want to marry, friend. This is a fuckin’ guy tarted up you’re talking about. Is he worth spilling blood for?”
“She, you bastard, it may be a trannie but she’s done you a favour tonight, you’ve got your horn off, Jack, now let us out of here. Or else. I mean it, I ain’t messin’ and you know it. Your wife might be banging the guy from the store or somethin’ while you’re away. But mine left me nearly two months ago now and I ain’t done nothin’ ‘cept work since then, tryin’ to take my mind off things. So right now I’m gonna get me somethin’, somehow. But I’m gonna do it my way. OK?”
I’d never met this guy before but I could tell, his voice said it all, he really was serious. He held out his billfold towards the guy behind the bar.
“OK Carl, take a twenty out of there, we’re off out of here. Come on Missy, you’re with me.”
He grabbed my arm and pulled me away from the other guy. I reached for my purse and tottered after him, not wanting to disgrace myself by falling in my high heels. What was I thinking? Disgrace myself? After what I had done? But I managed to stagger out after him, half being dragged, glimpsing the other guys from the bar standing in the doorway looking after us. And seeing the big guy realise his cock was still out and hurriedly pulling on his zipper to get himself looking decent again.
Charlie pulled me towards a truck, a big truck. Probably no bigger than any other but from real close up it looked big. He reached up to open the door, then grabbed my round ass and boosted me up and into the cab. He pulled himself right up behind me and slammed the door, then shoved me again, over the back of the driving seat. I tensed myself ready to hit the floor of the cab and was surprised to land on something soft. The internal light came on, I was spread-eagled across a mattress on the floor at the back of the cab. I realised I had known about this, that some cabs had some sort of ‘built-in bed’. So guys could get some sleep pulled into a lay-by for the night. I tried to sit up but was surprised again when I heard the engine start.
“Hold on Missy” called out Charlie.
My driver, my ‘escort’, my kidnapper, whatever, some or all of these. He gunned the engine and I was thrown sideways as he threw the rig into gear and pulled out. I just sat there. Silent. Not, to my immense surprise, worried. Maybe I’d gone past ‘worry’. But curious, yes, I wanted to know what this guy meant by ‘gonna do it my way’. Then I passed out.
I have now a vague recollection of the journey, but only vague. Maybe about half an hour, some of it along main routes, eventually along a track of some kind. I must have been partially conscious when Charlie leant over the back of the seat and offered his arm to help me climb over. I did so, probably rather indecorously. I really had no choice but to reveal an awful lot of leg and bare thigh to him. I distinctly remember having some trouble with my massive high heels on some gravel somewhere. And giggling about it, the combination of semen and alcohol in my stomach was having a weird effect.
I remember going into the john. I remember vomiting. Then I slept.
And then. I remember waking up, slowly, looking at a rather dirty ‘white’ ceiling with a single bulb illuminating the room. A bedroom. I was lying on a bed. Again, a slightly dirty bed, it smelt a little. I managed to stand up and then realised – I was not fully clothed! I was not naked, sure, but as I stood there in bra and panties and stockings – I wondered just what had happened. I remembered being at the truck-stop the night before and what had happened there. I knew I had been ‘rescued’ in some way or other, driven to – to where?
I moved towards the window, a bit painfully in my stocking-clad feet over the rough floor. I kicked something. My shoes. I knelt over and put them on, instantly growing six inches but happier, feeling feminine to an extent once again. I glimpsed myself in a medium-length mirror stuck to the wardrobe door. My wig was still in place, all my jewellery, and the make-up didn’t look too bad either. I pulled the small drapes back from the window and was hit – twice.
The first was the thought – where the hell was I? I could see out clearly, over rolling hills and farmland. Not Hackfield, certainly. And then the second impact – my head! The bright light triggered the instant hangover, and forty or fifty small men inside my skull began beating on my brain with not-very-small hammers. I grimaced at the pain of the mother of all headaches, turning away from the window.
“Mornin’ missy, you do look rough. Thought so, you must have had a dozen gins or so last night, not surprisin’ is it? Here, get this down you”
I looked up and unscrewed my eyes. This was the guy, the one who had dragged me out of the diner, the one who drove me here. Charlie. That was his name, Charlie. The Little Big Man, that’s what someone had called him. But why? I looked towards him, to his hand holding out a tumbler full of a brown liquid with something grotesque and green floating in it.
Helen began to lead Miriam away, then turned back to me and looked towards Neil, stood beside me. Then she whispered “You’ve got ten minutes” .
Ten minutes? For what? Hell!!!
I was standing there. With Neil. Helen had set me up again but this time she was serious. I turned to Neil, he was staring at my cleavage. I could do this. Helen had set me up. And I could do it, I could really do this. I felt rather sorry for Neil, I was using him but – what the hell. We were both going to have fun, I knew it. I smiled coquettishly at him.
“Like what you see?”
He blushed a deep red colour, he was clearly embarrassed as hell. I thought quickly, turned and grabbed my purse from just behind me together with two champagne glasses and a half-full bottle which was beside them on the table. I couldn’t drag him this time, my hands were full.
“Follow me” I ordered quite sternly.
He really had to obey. I headed down the hall and round the corner, then turned to push the bottle and glasses into his hand. I opened my purse and took out a key and opened the door. I went through and pulled him after me. Got him, exactly where I wanted him. There was enough light coming into the room from outside to allow me to totter along the corridor and reach the bedside lamp – in my bedroom. I’d led Neil through the connecting door into my own flat. I locked the door behind me and then, in a flash of inspiration, turned and dropped the key down my cleavage.
“If you want out you’ll have to get that yourself” I said boldly, smiling rather wickedly at him.
He looked terrified. Not surprisingly, I was suddenly feeling extremely dominant, a role I had not really imagined myself in. I wasn’t the femme fatale, I was the Mistress. With a capital ‘M’. I was almost leering as I began to move towards him. I breathed in gently, allowing my ‘bosoms’ to swell – his eyes moved down. I seductively slid my tongue across my glossy scarlet lips. And I spoke in as sexy and husky a voice as I could manage.
“OK, Neil, my darling, pour us a drink will you? Then – maybe we can catch up where we left off? Don’t worry about Miriam, I wish you’d told me earlier but now … well.”
With which I moved closer and touched my lips gently to his. He was shaking visibly. He was still nervous but really did warm to me as I caressed his body with mine, rubbing my leg up and down his thigh. In the quiet semi-darkness I noticed something I had not really reacted to before. The smell. The smell of sex. I could smell the sweat coming from his body and, I think, from between his legs where something was beginning to happen. When I had reacted automatically to Helen’s ‘invitation’ to seduce Neil I hadn’t really thought what that meant. What I was going to do, that is. But now I knew.
“Relax, darling, it’s OK. Just you leave everything up to me” I murmured in his ear as I massaged it with my tongue and my red lips once more, beginning to move my fingers tantalisingly over his body.
Then we sat down on the bed and I moved to lie across him, to unfasten the belt on his trousers. Before he had time to react I had the zip down and reached in – to expose his now very erect cock.
This wasn’t the same as with the other guy, Dave, that is. This was different. This was consensual sex and I was enjoying the experience, with my first man. For the first time really I was looking at the object of my desire. Neil’s erect penis. It seemed long to me, it was certainly very erect, a tremor went through my body when I realised I had actually done this. This was down to me, this gorgeous erect pole would be small and feeble if it were not for the sexual attraction between the two of us.
“Neil darling, could you help me with my dress? Just pull the zip down – that’s it, thank you, honey.”
And as I slid my dress off I stood before him, for the first time really as a man’s object of desire. I looked at him, he looked at me. We were both in our very different ways, for totally different reasons, as horny as we possibly could be. Which is in a sense exactly as it should be between a man and a woman.
“Jeez, Bethany, you look sensational!” was all he said.
It was enough. I leaned over him again and invited him to unhook the front of my bra. He did so with trembling fingers. And my very-realistic ‘boobs’ fell out. I realised he was very horny, obviously, and that I had to manage this carefully. So I just took hold of his thick rod and caressed it quite hard, watching it swell up even more. The colour of the cock-head surprised and fascinated me, it was a deep purple from the blood coursing through it. I kissed it gently, then opened my mouth and slid my lips down, half way down my first erect prick.
I slid my smooth lips up and down Neil’s hard rod a few times. I didn’t have to wait long – he climaxed within half a minute. There and then I experienced the first orgasm of another man as his cum shot out and down my throat. I swallowed as it poured out and was really disappointed as his cock subsided to a fraction of its former self. I sat up and looked at Neil. He was happy, deliriously so.
I knew exactly what he was feeling. BTDTGTTS. I found the key I had dropped into its hiding place and put it back into the lock, then re-fastened my bra and went into the bathroom to do what was necessary. When I came back Neil was gone. I lay down for a moment to recover.
And I woke up – eleven hours later!
Gin has never affected me as much as beer used to. At least I coped better with five or six gins than I ever did with ten or eleven pints of beer, a typical heavy ‘male’ drinking session. And the very best cure for a hangover for me has always been simply sleep. With the result that when I did wake that day, the first day of another New Year I had remaining only the last vestiges of a hangover. I’d slept through the rest.
Over the next hour I undressed, cleaned myself up, removed my stuck-on prostheses and re-dressed and so on. I emerged to bright sunshine after a large mug of coffee feeling on top of the world. Something had changed, obviously. In a situation I had only fantasised in recent months I had ‘been’ a woman, socialising, laughing and joking, being the barmaid, the hostess and, OK, the flirt and finally the seducer. I felt complete, or at least much more so than before. Now to get on with the rest of my life.
I had my second degree to complete, to get my Masters, but things were looking up there too. I had handed in the initial stage of my project and I thought it was looking good, hopefully Prof. Kingsley would agree. He was a bit antique himself but a good guy, he kept his finger on the pulse and would recognise the positive aspects of what I was trying to do.
Or at least I hoped he would, I’d find out in the next few days. Meanwhile, what to do? I could always start to make progress but if it was approved I ought to start out on the big opinion review. Which would be wasted if I had to change tack. Better to wait that few days so that I wouldn’t waste any effort. I decided just that, I was ready for it but it was better not to actually start yet. Have a day or two off. Just relax, things had been pretty hectic round here after all. I was just sitting on the small bench outside the flat, in the bright sunshine even though the air was quite cold, having my second coffee of the morning. Nice day, nice world. I liked this.
But what to do? I decided to go for a jog, hadn’t done that for weeks, so many other things had happened. I dashed in and changed, put on my track suit and trainers, locked my door and set off. I hadn’t done this for too long, I really needed to get into shape. Not that my shape last night had anything wrong with it.
Boy had I looked good. Or rather Girl, hadn’t I looked great. I jogged the few hundred yards up the Dudley Road to the small park I had visited before and then, slightly faster than I really expected, did three laps of the park. OK, the whole run was only about four miles but I still felt I was doing myself some good. And when I got back I had a long, very hot shower and dressed casually and comfortably, wondering if I should maybe go round to see Helen or Charlie, thinking really how to start out the New Year before the new term.
I remembered one obligation I had forgotten. I rang my mother and wished her a happy New Year. Luckily I didn’t have to talk to my step-father, he was apparently still sleeping off the night before even at that time of the day. Then at her suggestion I rang a few more family members, uncles and so on, for a bit of a chat. And a couple of my friends from college who had gone back home for the holidays. After which I was feeling pleased with myself.
I got through the day, did a few more calls, and slept well. I rose not-too-late the next day, wondering again how to fill my time constructively. Try on more of my new lingerie maybe? Experiment a little more with my make-up? Practice more in my high heels?
And then Helen came round. With somewhat surprising news.
“Er – Andrew rang me a while ago. He wanted Bethany’s phone number. He’s asked me several times since Christmas but I’ve kept saying no. But after the party, well, I saw Neil go so I guess you rather enjoyed yourself.”
“This is weird, Ben. I mean Bethany had a good time at the party, didn’t she? This is so weird. Anyway, did Andrew ring you yesterday?”
I told her I’d been ringing various people myself for much of the time so maybe he hadn’t been able to. Then I realised the implications of what she’d said.
“Hang on, Helen. Did you give him my number?”
The phone rang. I sat there in silence.
“Go on then” said Helen.
I picked up the phone. It was Andrew. I listened for a moment and then spoke. And now this was so very weird to me, the voice I was using was my ‘Bethany’ voice. I listened while he told me he’d been to his sister’s the for New Year and had stayed over and how he wished he could have been at Helen’s party. He’d looked forward to maybe meeting me again.
“Look. Bethany. Can I come round this evening? About eight? Maybe we could go for a drink? Do you know Senorita’s?”
Just at that moment Helen had been leaning over with her head next to mine, listening. She heard it all. I hadn’t replied, I was so surprised. She just looked at me and nodded, mouthing ‘Yes, go on, say yes.’ Which I did. I put the phone down.
“OK, so Bethany has a date” said Helen.
A date. Yes. Wow!
Helen looked at me again. Yet again she had dictated to me, decided what ‘I’, Bethany that is, was going to do. And yet again I had my doubts, OK, Helen had got it right so far at almost every stage. But this time, this was serious. Just what had she got me into?
“OK Ben. I can tell you are not so sure about this. But trust me. I am a pretty good judge of people and I do know what I’m doing. When Andrew gets here tonight he’s not going to know what to expect so it’s up to you to lead the way. He will find out what you want him to find out, but only if and when you decide. This is your date, and it’s your day. Now. I have a couple of phone calls to make, I’ll be back in about half an hour.”
I was somewhat reassured by Helen’s comments but not totally so.
“And then we’re going to get you ready. Please, indulge me, I’d love to help. I really would like to watch the transition Ben. The whole idea has fascinated me ever since a couple of weeks ago. And maybe I could help?”
OK, That was it.
I had been thinking while Helen had been talking. This Andrew seemed like a nice guy. Certainly I could see why any woman would consider him handsome, he was tall and well-built. In a sense a trannie’s dream really. And maybe he was gay. That meant I didn’t have to be quite so scared of him finding out my secret. And anyway he suspected it already, that was probably why he’d suggested the date. I just had to go ahead.
After Helen left to make her calls I decided not to rush things.
‘Take your time, Ben, do it right,’ my late father had always said.
I’m sure he’d have been surprised to find me applying his words of wisdom to me dressing up in women’s clothing, much less wearing makeup. And going on a date!
OK, but the advice did apply to Bethany too. I did make a start. I had a hot shower and used the depilatory cream lavishly all over my body, then dried myself and applied my favourite talc in all the places I thought it should be applied.
Then I sat down to watch TV! For over half an hour, I watched the end of the News broadcast and then one of those ‘classic’ sitcoms which are all the rage. I’d never really understood its attraction the first time round but by the end I was chortling away merrily, feeling very relaxed. Just as it finished I heard my doorbell again, it was Helen.
“Well Ben, you still are Ben aren’t you? You do smell sweet. Have you started yet?”
“Nearly, I was just relaxing first but I’d better get on with it.”
I hesitated for a moment, then slipped off my robe to reveal my naked body and looked up at Helen. I just couldn’t help it. My excitement very rapidly revealed itself.
“Wow Ben, you are about to have problems. I mean, I could help with that but I don’t think Charlie would like it!”
I grinned and turned away, reaching for a pair of black panties. I pulled them up and tucked myself in, then turned back to face Helen. Her eyebrows rose.
“Where is it?” she asked, smiling.
“Don’t worry, it’s just a trick. It’s folded into these panties. Now, I think I’ve decided what to wear but I would like your advice.”
I showed Helen the blouse and skirt and shoes I had chosen. She looked at me in disbelief.
“Ben, or rather Bethany. What are you trying to do, put your date off from the word go? I know you’ve got quite a lot of clothes by now and I know you can do better than that. So you sort the breast-forms, I’ll have a look through the wardrobe.”
So I did do the tits, I lay down to allow the glue to set while Helen busied herself sorting out my outfit. When I got up I did the make-up over the seams and then turned to put on my wig. Helen looked at me.
“Well. Bethany, definitely. Ben has gone. OK, lingerie first.”
I argued that what Helen had chosen seemed a little unsuitable but I had been over-ruled. Within minutes I had on the black waist-cincher and the bra which matched the panties, the black set I had bought at ‘CCs’ before Christmas. They were a better quality than I had thought, but then I realised I had got the full discount when I had bought them so they really would have been quite expensive. The sheer black seamed stockings came next, then I started on the make-up.
Here Helen was a great help. I ended up with exactly the look I had wanted but this time using only half as much to cover up as I had done before. It was a case of quality rather than quality. I sprayed a little perfume between my ‘tits’, then finished by sticking my longest set of red nails in place. And this time I super-glued them, no risk of my embarrassment in whatever situation I ended up.
With earrings and a choker and several rings and bracelets I was beginning to really feel the part. Then Helen revealed the top she had chosen for me, one of the close-fitting sweaters I had bought from ‘CCs’ again. And to my amazement she stood there holding my favourite item of clothing. My black leather micro-skirt.
“I can’t wear that to go out in, Helen” I exclaimed. “That’s just for fantasies in front of a mirror!”
“Humour me” said Helen.
She insisted I put it on, together with my highest black patent stilettos. I stood there wondering what Andrew would think.
“Bethany, he will love it. Really, dear, you are just oozing sex. The boys at Senorita’s are going to get a real treat. Call it what you like, eye candy or whatever, really you are a guy’s wet dream. They’ll all be jacking off in the Gents and thinking of you.”
If I blushed, it probably wasn’t evident under my make-up.
“And Andrew, if he is the man I think he is, will absolutely love being seen with you. I’d love to see his reaction but I mustn’t stay. Good luck, Bethany. And if you feel like doing anything I wouldn’t do – just do it. Have fun.”
With which Helen squeezed my hand, and left. I was on my own, contemplating what she meant. Again I decided to relax for a few minutes and sat down to sort out the contents of my handbag. And then, a few minutes early, I heard a car pull in outside. I pulled the curtain to one side and peered out. It was Andrew.
But he didn’t come to the flat, it occurred to me then that maybe he didn’t know exactly where I was living, exactly what the situation with ‘Bethany’ and Helen and Charlie was. I opened the window slightly and listened. I could hear two male voices. Then I heard the door close and footsteps outside. And my doorbell.
‘OK Bethany, here goes,’ I thought, and opened the door.
My ‘date’ was standing there. Looking indeed slightly embarrassed. For a moment I wondered why. After all he was obviously a man of the world, a man with lots of experience, varied experiences, in many matters – including sexual ones. Then I realised this was probably a new one to him. Calling on his date, probably a transvestite, and really not knowing what to expect. But if he knew anything at all about TVs, and in this respect I was typical, what any tranny really wants is to be treated like something we really are not. Like a woman. How would a gay, or maybe bisexual, guy cope with that?
Well, Andrew was trying to cope. He was standing on my doorstep, looking rather nervous, holding out a medium-sized, but absolutely gorgeous, bunch of red roses! Where on Earth had he got them at that time of year? They must have indeed cost the Earth. I gasped a little in surprise, then recovered. Even before I could speak to thank him he jumped straight in, straight to the point.
“Er – Bethany….”
It was there again, that brief pause. But this time I didn’t really mind.
“I’ve asked Helen about five times and she won’t tell me. And I’ve just asked Charlie and he’s obviously under some sort of instructions from her. Please, I have to know. Are you… seeing someone? Or ….?”
I didn’t let him finish. I just moved the roses to one side and leaned over to kiss him on the cheek, right next to his lips.
“Later, Andrew. Now, thanks for the flowers, they really are lovely, it is so sweet of you. But what kind of a hostess am I? Please, come in for a minute, I’ll just put these in some water.”
I noticed a small reaction as I said ‘hostess’ – that surprised him. I was internally beaming. Of course he was almost certain but – there was still just a little doubt. He actually did still think I might be a woman. But if he’d seen me in the kitchen he would have known otherwise. Flowers? How the fuck was I supposed to deal with them? OK, they were lovely but I had nothing suitable to put them in, no vase, no display jug or anything. I quickly grabbed a coffee pot from a shelf, ran a little water into it and pushed the roses in. That would have to do for now.
I rapidly turned and went back into my little lounge. Andrew was looking through my CDs. Well, he’d get no real hints there. Basic 80s and 90s pop-rock, fairly gender-neutral, I thought though maybe I was deceiving myself. Anyway he wouldn’t have time to investigate fully.
“OK Andrew. Helen said something about ‘Senorita’s’. Do you really want to go there?”
I had tried not to say anything with the tone of my voice, just keep it neutral though I hoped the timbre was as feminine as I could muster. I could see Andrew thinking. He was looking straight at me. Had Helen and I overdone it? Was he looking at a woman or a trannie? And if he did see me as a woman, what sort of woman?
I could just see my reflection, not too clearly, in the reflective glass behind him. All legs and heels, tits and hair, a bit of a dressy girl maybe? A sex object? Anyway, whatever he was thinking, he didn’t really show it to me.
A series of stories with TG themes, dedicated to women, and to men who like to be women (which includes me!)
It really all began in late-ish teenage for me. OK so I realise now there had been signs before that, but I’d not paid them much notice. Little things, significant now that I could put them into context, but seemingly unimportant at first.
The acne started it, typical teenage problem really, with all the raging hormones and so on, it wasn’t too bad but it did cause me some concern. Mum and Dad both kept trying to reassure me, tell me that I’d grow out of it and so on, but like all teenagers I thought it was the end of the world. It did hammer my chances with the girls at school, at a time when everyone else in class was pairing off I was at something of a disadvantage.
Eventually my parents decided to do something about it, before at the start of my last year. With exams due at the end of the year and the possibility of college I really did want to do well. I went to the doctors and was prescribed some tablets, nothing really special about that. And they did begin to have an effect, my skin began to clear. OK it may not have been the pills, I was on a health-food kick at the time, salads and low-fat and low-cholesterol foods, anything which might make a difference. My friend Peter said he’d tried some sort of herbal derivative and it had helped him, so I gave that a go.
It was about a month after that I noticed the beginnings of my ‘problem’. It had started with a bit of a rash, just itchy, nothing nasty, under my arms of all places. Again I’d gone to the doc and he’d prescribed a mild steroid cream, just to smear gently over the affected area for a week or two.
The itching stopped. And the swelling started. And I began to get hungry, specially for cheese and milk and cream and stuff. I began to put weight on, but not on my waist. On my breasts! The swelling got out of hand quite quickly, after only ten days or so my flattish manly-ish chest was sporting two definite mounds. It was embarrassing! I didn’t tell my parents at first, just carried on going to school, wearing a loose sweater whenever I could but things soon couldn’t be hidden any more. I just had to tell them.
One evening I did. Naturally they were both very worried, as soon as they saw the evidence, Mum went with me to the doctor’s again the very next morning. He was worried too, I think he’d not come across a case like mine before. He referred me as a matter of urgency to the local hospital for some tests, he even rang them up there and then to be sure I could be fitted in immediately. And Mum drove us straight there. They did blood tests, urine tests, various others, rather mechanical really. And then we went home.
It didn’t ease my mind when our own doctor rang Mum at home that evening. He’d had the tests rushed through and the results faxed to him, and could we come in again the next morning at the end of the surgery to see him?
“Well, Harry, the good news is that we’ve got something positive from the results. I admit yesterday I was puzzled but I did some research last night. I found seven cases like yours in the UK, all in the past five years. And every one has been cleared up totally satisfactorily”
“Well doctor” said my mother. “That’s a relief. A big relief. So you can suggest some treatment.”
“Yes I can, Mrs. Davies. But not yet. That’s the bad news. It has happened rather more quickly than in any of the other cases but the blood tests do show that it is totally reversible. The difficulty is that it’s going to take a little time, maybe as much as several months, even a year.”
“A year! Oh no!”
That was my comment.
“Oh no!” was my Mum’s comment.
“Well, maybe not so long. But there have been major changes in Harry’s hormonal system, we can’t just rush in and try to undo them. It might do more harm than good.”
The doctor went on to explain. As some sort of side-effect to the treatments I’d been having, as well as a minor initial condition, I was developing MPMs – ‘masculine pseudo-mammaries’. They weren’t real breasts, obviously, but they did look like female breasts. It would take some time to settle down my hormones before I could be given the best treatment.
“Look, Mrs. Davies. Like I said, I was worried yesterday but the prognosis really is very positive. By this time next year Harry should be totally back to normal, and permanently so.”
We left the surgery, both of us with confused emotions. Dad’s reaction was the same when he got home that evening and we told him.
“But what about Harry’s exams? OK, he’ll be able to do them next June bet this is going to disrupt his education. He won’t be ready for the exams.”
I was sitting in a large armchair, feeling sorry for myself, and feeling the weight of the two bulges in front of me.
“Mum, Dad, there is NO WAY I’m going into class looking like this. I could take a bit of general ribbing, but like this I’d be a total laughing stock. You HAVE to do something about that.”
And they did. Give Dad his due, when he decides someone has to do something he will write and call and chase to get it done. Within a week, just before the very end of the holidays, we had a visitor. I didn’t really want to see any visitors at that time but Dad had persuaded me, even taken the day off work for it. He showed the man into our living room.
“Harry, this is David Carlisle. He’s a home-study tutor. I’ve got the school governors to fund his coming here, or you going to his house, to give you individual tuition until you’re able to go back into class. Mr. Carlisle, this is my son, Harry.”
I got up carefully, so as not to cause any frontal ‘wobbling’ on my part, and shook his hand. Then I sat down again, equally carefully, while Mr. Carlisle asked exactly what stage I was at in my various studies, taking copious notes.
“Well, Mr. Davies. And Harry. I think I can help you. The Maths and Geography and Biology aren’t a problem, I’ve tutored students in all those at this level. And the English Language I know of a decent self-study programme Harry can follow. Maybe one or two afternoons a week. I have one other student at the moment, she sees me each afternoon. So if mornings are all right for you we can go ahead, Mondays to Thursdays if that’s OK. Starting Monday?”
Dad and Mum were both pleased, this Mr Carlisle seemed a nice man. And, while I’d been telling him about my various courses and so on, he clearly knew his stuff.
“Harry, you never know” said Mum. “With this private tuition you may be able to do even better in your exams next year.” Good point.
The first awkward moment came the following Monday, when we broke for a bit of air in the middle of our Maths session. We were sitting in Mr Carlisle’s garden in the late summer sunshine when he asked me if I wanted to tell him just why I was getting the home tuition.
“You don’t have to tell me, Harry, if you don’t want to. But some of the students I’ve had in the past like to get it off their chest.”
I almost choked on my orange squash!
“I know yours is some sort of medical problem, the school governors told me that when they approached me. You know, I’ve had pupils with all sorts of problems. Broken homes, drug problems, youngsters with criminal backgrounds. And disabled pupils too.”
“Oh I wouldn’t count myself as disabled” I said. “Just a very embarrassing medical problem. That’s why I wear loose sweaters.”
I decided to tell him.
“I’ve got a hormonal problem. I’ve developed female-looking breasts. They won’t stay, though, it’ll take quite a few months but they will go away. I should be back to normal in a year.”
He didn’t say anything for a while, he looked rather worried. Anyway, we got on with the Maths. It was on the Wednesday, in Maths again, that he commented again. I was a little unsettled, physically that is, though the worst of my symptoms had lessened since I’d stopped all the medications the acne was coming back again a little and I itched in other places on my body. Not in a major way but the weather was still quite warm and the big sweater and baggy trousers were uncomfortable.
“You OK, Harry? You don’t seem it. If you’re going to study properly, you know, you really do have to be comfortable.”
“It’s OK, Mr Carlisle. Just a bit uncomfortable, that’s all.”
“Yes, just a bit tender in some places.”
“Can I see?”
There was nothing at all untoward in his request. Just a concerned adult, a tutor indeed, wanting to find out what a pupil’s problem was. I decided, I had thought about it, to be honest with him, to show him what my problem was. It was indeed the entire reason I was there.
“I need to warn you, Mr Carlisle, I am wearing a bra. It’s one my Mum got for me, a sports bra, to try to hold things in so I don’t get too embarrassed when I come here.”
We’d decided, since Mr Carlisle had all his books and stuff at his house it was easier for me to be tutored there, he was only five minutes’ walk from where we lived and I could manage that. Suitably clothed of course. And in that respect the bra helped, though it really did itch.
I lifted up my sweater to show him. I suppose he could see my ‘swellings’, the two of them, though I didn’t take the bra off.
“And in case you’re wondering, they’re a 38-C at the moment. The doctor says they’ll probably peak at about a D-cup and then subside.”
“Oh my! And when will that be?”
“A few weeks, maybe months. He can’t really tell. But he did say once that starts happening they should go down quite quickly.”
Mr Carlisle thought for a moment. He seemed to be day-dreaming. Then he coughed a little.
“OK, Harry, try to concentrate. Meanwhile I’ll have a think, see how you could maybe manage things better.”
And for a few days that was that, we just got on with the studying. Then one day a week or so later he came up with a suggestion.
“Harry, look, I’ve got something to show you. It might make things a little better for a while. I spent a rather embarrassing afternoon in the Ladies’ Dept in Roddhams yesterday. Please, if these aren’t alright please say so.”
He took a bag from a drawer in the old-fashioned dresser we were sitting next to in his dining room. I saw the big green-and-white Roddhams logo. I opened the bag and pulled out the package
‘Lingerie set, 38-D, Deep Purple’.
I looked at the label. I looked at the contents through the clear packaging.
“I thought they might be OK. The size is the nearest they had to what you said. And the colour might not be perfect but it was either that or red in that size, I thought that might be best.”
I was amazed. Puzzled and amazed. I split open the seal at the top of the packet carefully, I always did that in case the size might be wrong and they might have to go back. I slid the contents out onto the table in front of me. They looked incongruous on top of my Biology folder.
“Well, I think ….”
“That’s OK Harry. Leave it if you don’t think it’s a good idea.”
“Er – no. It’s not that. I just wasn’t expecting this.”
“I thought it might suit better than what your mother has got you, that’s all.”
“Well, it might I suppose.”
“OK. If you want to try them on you can go into my daughter’s room. I thought it might be more comfortable to wear while you study.”
“Yes, my daughter Marion. She doesn’t actually live here of course, but she keeps some of her stuff here for when she visits. It’s mainly clothes she used to wear when she was younger, she’s just never got round to clearing them out. No need to really, they don’t get in my way, she lives in London now. She’s in Australia at the moment though, back-packing, says she’s trying to forget her birthday. It’s a special one, you know, one with a ’0′ at the end.”
I thought for a moment. I hadn’t asked about Mr Carlisle’s family, well, you don’t do you? I knew his wife had died quite some time ago. His daughter must be – forty? No, surely not, that would have made him over 60 probably. And twenty was too young, she must be thirty. That must be it.
“OK then. I’ll give it a go. Like you said, if it works, ….”
Mr Carlisle showed me upstairs into Marion’s room. There wasn’t much in there, probably most of her stuff was in London. I didn’t look in the drawers or the wardrobe, maybe she’d left some clothes and so on in there. There was just one pair of shoes near the bed, that’s all. Anyway I inspected my package again. I looked at the bra, then at the label. ’38-D under-wired padded, brassiere.’
I pulled the curtains closed, then took off my sweater and the white sports bra I was wearing. I slipped my arms between the straps of the bra, clipped it at the front and then slid the shoulder straps up into place. And then I adjusted the ‘cups’ so that my own swollen breasts settled into the right places. It seemed that they didn’t really hold things up, then I realised the shoulder straps were adjustable. Again I nestled my breasts in the cups. Now, it made a difference. The straps definitely did support the weight of my ‘MPMs’ and felt so much better than the white one mother had given me.
I looked in the mirror. Obviously, apart from the silkier smoother texture and the colour, this was an item with a different purpose from the tight-ish sports bra I had been having to wear. This didn’t just grab things and squash them in to prevent any unnecessary movement. It was supposed to support the breasts of course, but as well as that it was designed to be attractive, to allow a woman to show off her breasts and her cleavage to an extent. It did push my own MPMs up and together rather, giving me what I could only describe as quite an impressive cleavage.
I smiled. I was thinking about Holly Tomkinson in my class, she of the large boobs and prominent nipples. I’d noticed hers from quite close up a few times but she’d have been jealous if she’d seen mine there and then! And I was also thinking I’d like to see her in a plunge bra like mine.
I shook myself out of it, got my thoughts back on track. Basically it worked. The texture of the bra was much nicer next to my rather sensitive skin, and it did indeed support me very comfortably. I pulled my sweater on. Luckily I’d chosen a dark blue one, the bra didn’t show through at all.
Then I looked at the panties in the bag, the same purple colour and the same material, but very skimpy indeed. It occurred to me that these might help too. The troubles with my skin had started up again a week or two earlier, again not as seriously as when I’d been on the medications but this time more widespread. Maybe these would feel better than my ordinary boxers?
I slid off my trousers and shorts and stepped into them. I pulled them up rather tightly and again fiddled to adjust them round my own , this time male, bodily parts! Indeed they did feel rather nice. Quickly putting on my trousers and shoving my own bra and boxers back into the Roddhams bag, I headed back down the stairs.
“Well, Harry? Any comments?”
“Yes, Mr Carlisle. Thanks for the idea. They do actually feel much better, less liable to rub and cause my skin problems to worsen. Thanks.”
“But you really shouldn’t have, you know. I’m sure that’s not part of your job. You shouldn’t have to buy things like that for your students.”
“Oh, I’m not paying. I’ll put it down as expenses, probably as ‘special clothing’. The Authority will pay it. I don’t claim big expenses, they know that, they’ll probably pay it without even looking.”
I just had to smile.
“You mean they are paying, basically, for me to have women’s sexy lingerie while I’m not attending school. That’s weird.”
Mr Carlisle smiled widely too though with a bit of a strange look on his face when I’d said ‘women’s sexy lingerie’. “I suppose it is, I hadn’t thought of it that way.
“Anyway, come on, back to your studies.”
“OK. Oh, I tried to leave things tidy in your daughter’s bedroom. You may want to check before she comes back, she might get the wrong idea.”
Mr Carlisle grinned.
“Don’t worry, she’s not due back for some months, sometime before Christmas I hope.”
And we got on with the Biology. The different under-clothes really did improve things, quite a lot, I was surprised. And I was also taken aback at the comment I made at the end of the session.
“Thanks for thinking about the comfort thing, Mr Carlisle. The bra is fine, I’m not too sure about the panties. They are rather brief. Maybe having something smooth over the whole of my leg surface might help.”
I really couldn’t read Mr Carlisle’s reaction to my comments, he looked rather uncomfortable himself.
“Sorry, Mr Carlisle. Maybe I shouldn’t anyway. But I’d better change before I go home, Mum will probably be back when I get in. Bye sir.”
Funny that. I had got into the habit of calling him ‘Sir’ at the end of our sessions, though it was always ‘Mr Carlisle’ during them, and when talking to Mum and Dad.
The next day was a Friday, and I went for my medical check-up which I did every other week. This time at the hospital I had two doctors to myself, one an attractive younger woman, the other the same older man I saw most weeks. They tested and measured my MPMs and went into a huddle to whisper something.
“Don’t worry, Harry, it’s just that yours is a rather rare case” said Dr Hill, the usual doctor. “I wanted Dr Weston to see, maybe give me her opinion.”
“Yes Harry” she continued. “I’ve read up on the literature. As Dr Hill has told you, we’re looking at a full recovery in a few months time. I think the swelling has maybe finished, certainly it shouldn’t carry on for more than a few more weeks. I reckon your breasts would be a 38-DD at this stage, did your mother choose the sports bra? It seems a good idea. Anyway, how are you doing in other respects?”
I told her about the skin problems, and the irritation I was feeling.
“Well, Harry, I’m sorry but unless that gets really bad you’re just having to endure it. I know it’s difficult. But your original problem has been caused by the complications in the different medications you were prescribed. I’d like to keep you drug-free, in all respects, for a while yet. OK?”
I nodded my agreement, I could see the sense in that. I put on my big sweater again and went back, head down, out to the car park where Mum was waiting. I could probably have coped on a bus then but I didn’t want to risk the ridicule or embarrassment.
At the start of the next week I turned up again at Mr Carlisle’s house and started off by presenting him with my Biology homework.
“OK Harry, I’ll have a look through it now. Do you want to go up and change? You don’t have to, you know.”
“No, I’d like to.”
“OK then. And there’s something else up there you mentioned” he said, burying his head in my notes.
I went up. The bra and panties were on the bed. And another packet. A pair of tights. I again looked at the label again before opening them. ‘Sheer, black, 10D’.
I put on the bra and thong and then opened the packet. I was surprised at how flimsy the tights seemed, so I handled them extremely carefully. They really did seem silky-smooth, I think because the ’10D’ label meant they were of a good quality. I rolled up each of the legs in turn and slid it smoothly into place, then stood and pulled them tight.
I was at that moment wearing only that set of lingerie, I hadn’t put my sweater on after sorting out my bra again. OK so I’d inspected myself previously in Marion’s large mirror when I’d first put the fancy bra on, I was intrigued to know just what I did look like now. AND – I realised – I had to make sure my tights were on correctly. I looked in the mirror.
Wow, what a figure. There was a reaction inside my panties! I just had to stop looking as soon as I’d checked my legs, I had to settle down. I was here to study after all. I put on my sweater and trousers and pushed my feet into my trainers, standing to accustom myself to the rather strange feeling of the tights covering my legs. The feet felt – wrong. They just didn’t seem right in my trainers, probably because I wasn’t wearing my thick-ish trainers. I would have to put the socks on over my tights.
Then I caught sight of the pair of shoes, probably Marion Carlisle’s, which I’d noticed a few days earlier. Though I knew women’s feet were in general smaller than men’s, these shoes didn’t look too small. In fact with thin tights on instead of thick socks they could even fit. I thought of Mr Carlisle’s reaction. These weren’t something he’d bought for me in order that I could feel more comfortable, these were his daughter’s shoes.
Yet I really did feel they would do the job, enable me to wear the tights. And that was the point after all, wasn’t it? So I’d feel more relaxed despite my medical condition, and be able to study more effectively. Since Dr Weston had said she couldn’t help my skin condition with medication, surely I was justified in trying other methods? I had convinced myself.
I put on the shoes. They were, to be honest, just a little tight. But then so were my trainers, I’d almost grown out of them. Mum had mentioned something about getting me some new ones only a few days earlier. I stood up. I walked round a little. I looked down. I was amazed.
My feet actually looked – attractive. I’d never ever thought that of my feet before but the combination of the sheer tights and the shiny black high-heeled shoes, I really did think they looked nice. Not just any old pair of feet in trainers. I realised that what I was looking at was basically a pair of female feet. I mean, you never saw male ones like that, did you? And it was that aspect of the whole tights-and-high-heels thing I found attractive.
“You OK, Harry?” called a voice up the stairs. “Come on, time’s a’ going, I need to sort out one or two things with this Biology of yours.”
I entered the room nervously. Basically it was the shoes. I’d been presumptive in trying them on, maybe I’d gone too far. Mr Carlisle and I had a good working relationship, I didn’t want to spoil it.
“So how are things? You’ve got the tights on, I see. Oh my! You’ve got Marion’s shoes on too.”
“I’m sorry, it seemed a good idea. The tights are fine but they felt wrong with my trainers. I hoped you wouldn’t mind.”
“I don’t mind at all, Harry. They were to throw out anyway, I’d forgotten about them. Marion told me about them before she left, she says they’re the wrong size, not labelled correctly. They’re too big for her. If they help you, that’s fine. OK now, this Biology, come on. The first section is good but you’ve got your head round something totally wrong in the second part. Look here.”
I looked. We discussed. I studied. And I like to think I was doing well. Maybe Mum had been right, I was learning stuff better with a home tutor than I would have done at school. OK so it was only eight hours a week but I did my home-works and so on. And we carried on like that for four or five more weeks, me changing as I got to Mr Carlisle’s house, doing my studying, changing before I went home. And my breasts? They seem to have stabilised. And the skin condition? Well, to be honest it did clear up from my body, but I’d got used to the routine, and really in a way I liked the underwear.
But it didn’t clear entirely. It was mid-November, just after the half-term break (which was really boring for me, stuck at home on my own, no lessons, no mates to visit except Jake, my one really good friend). During the week, for some reason, the skin problems returned to my face. Very embarrassing, I couldn’t effectively hide it at all. Just walked to Mr Carlisle’s house with my head down yet again, I was getting used to that. No calling in at shops or anything, just straight there and straight back afterwards.
“Doctor Hill has promised me she’ll give me some medication which should help in a couple of weeks. She’s reluctant,” I told Mr Carlisle one morning “because my – other problem – seems to be slow in subsiding, in fact – they haven’t started yet.”
“So you’re stuck in – entirely?”
Mr Carlisle carried on the lesson, then stopped about half an hour early.
“Harry, I just wonder. Maybe there is something more we can do to help. To hide the problem, just for a couple of weeks maybe?”
“That would do, certainly.”
“Well, it’s a rather strange idea but I do think it might work. Can I ask you to try something for me? Come upstairs, I want to show you something in Marion’s room. “
We went up, it did seem a little odd, this was the first time we’d both been in there together. Since I did my own changing in there I regarded it to an extent as ‘my’ room even though obviously it wasn’t. Mr Carlisle asked me to sit on the chair, the only chair in the room, and then opened one of the drawers in the dresser.
“My daughter, Marion, she has rather a sensitive skin too. Not as bad as yours of course.”
“Oh dear, Harry, that sounded awful.”
“No, that’s all right.” I wondered where this was going.
“So she uses a very light form of make-up, something which just does the job, enhances her appearance, that sort of thing. In the sort of job she’s in, in PR that is, she has to look good. Well, I just wondered if you’d like to try something like that yourself. Just to see the effect, it’s really a good quality product, dermatologically tested and all that. It might help.”
I thought for a moment. Makeup?
“So what would that involve, Mr Carlisle? I’m not sure it would help. And I’m certainly not sure I could do it properly.”
“OK Harry, let’s leave it for now. How about we try it just a little at the start of tomorrow’s session? You change now, it’s almost time. I’ll look through these drawers and see what I can find. OK?”
“OK then.” I said. “I’ll try anything once.”
The next morning I went straight up to change. Then Mr Carlisle came in, he brought another chair and sat beside me.
“I don’t want to spend a lot of time on this, just a quick go. OK?”
He had arranged quite a few bottles and tubes along the dresser. He started with one flesh-coloured tube, squirting the thin paste onto a sponge and spreading it over my face.
“Here, Harry, you continue. It seems to be covering, and it doesn’t look too bad, does it?”
Indeed it didn’t. On the one hand it did cover the irregularities in my skin very well, and on the other it gave my face a pleasant sheen. I took a minute to smoothe it into place, then Mr Carlisle took a brush and spread some powder over some areas of my face, basically to give the rather flat surface some sort of relief. Then he got a bigger brush and some deeper pink powder.
“And just a little blusher, I think. OK?”
After that he got a pot of deeper pink paste, basically a lip colour, and applied it very carefully with a brush over my lips, finishing by coating them with a gloss liquid.
“Now, I have to admit, Harry, I think that looks very good.”
I looked. I rather liked what I saw. My skin had become rather badly marked over the previous week, Dr Weston had said it was a sign that things were finally coming to a close.
But the effect of the make-up was to cover all the flaws, very effectively. I knew I couldn’t go out in the street like that, Mr Carlisle agreed, but he was quite happy for me to continue with our studying with me made up. I didn’t do it on the next few days, but at the end of the following week I suggested I try the make-up again.
“You want to do it yourself?”
So I did. I managed very well with the foundation, the highlighter, the blusher, then the lip-colouring and the blusher. The result looked – quite good, I thought. Finally I looked in the wardrobe. OK, so Marion’s shoes were a little smaller than mine, what about her clothes. I took off my sweater and trousers, and slipped on a pair of her jeans. They were tight, yes, but wearable. I got a sweater too, with a V-neck, again tight-ish. I liked the way it felt. I looked in the mirror. I wasn’t hiding my breasts, my cleavage any more. I was revelling in it. But – what would Mr Carlisle say?
I walked out of the bedroom, down the stairs, and into the dining room.
“Well, Mr Carlisle. What do you think?”
He looked at me. A strange sort-of glint came into his eyes.
“Well, Harry. I see you’ve decided not to hide things any more.”
“Well, just here, Mr Carlisle. I mean, just for today. I couldn’t go out looking like this, obviously. But just for in here, I borrowed some of Marion’s clothes. I hope, that is, if you don’t like …”
“Harry, it’s fine. Really. You look nice. Will you excuse me for a moment?”
He rushed out. He looked weird, like that first time I’d tried on the purple bra. Somehow it wasn’t the reaction I’d expected. I sat and looked at my books for a couple of minutes before he came back.
“Harry, you look great. Feel like some studying?”
We actually got through a lot of stuff that session, and in the next couple of mornings though I didn’t go quite so far with the dressing and the make-up. But I just felt good. The whole combination, the lingerie, the jeans and more than anything the revealing sweater, they all contributed to a feeling of well-being. We both worked, hard, tutor and student, we made a lot of progress.
Then, a couple of days later as I was going to leave, Mr Carlisle surprised me.
“Harry, I know you’ve been working really hard recently but we do need to sort out something. Your Geography is coming along really well but there’s a problem looming. You have a Project Study to do.”
“I know that. I had thought of using the High Street in town as an example, looking at the building styles and so on, that sort of thing. I thought I’d mentioned that?”
“You did, Harry. But I’ve been in touch with your school. The teacher there wants to get all the projects started before Christmas. And that should really include yours.”
“So what does that involve? Internet searches, I thought. I could do it all on PC.”
“You could, Harry, but I have to tell you the examiners are not so fond of Net-projects. They like you to actually get into the real world.”
“Sorry Mr Carlisle. Maybe I could do it in the evenings?”
“Yes you could, but you really need photographs, you should do it in the daytime. There is a way, Harry. Please don’t be surprised, but from what I’ve seen recently I think you might be able to get away with it.”
“Harry, in many ways, your figure specially, you look as much like a girl as a boy. I don’t think it would take much for you to be able to carry it off. I could drive you into town, then you could spend an hour or so on the High Street. With your notebook, and the camera on your phone. You can see what you need to see, get all the data that is and the photos. Then do all the analysis the next day. If you’re prepared to do it, that is.”
I’d listened carefully to the last part of what Mr Carlisle had said, then I realised just how he’d started the sentence.
“You mean – dress as a girl, a woman. And go out?”
“Yes, dressed like you are now. Not in that big sweater, those jeans would be OK though. It would just have to be for an hour, Harry. I can’t do the actual research for you, it’s your project. You have to collect the data yourself. How about next Monday? My other student won’t be with me then, she’s – er – had to go away for a while. We could spend a bit more time on it then, maybe do some of the analysis later, even.”
“Do you really think I could do it? I mean, it sounds a bit extreme really.”
“I’m sure you could.”
I thought. It was a silly idea really, but ….!!
At the end of the week I had my regular medical assessment, more tests and measuring. It was Dr Weston again, she sat down with me after all the tests.
“OK Harry. I really do think we’re coming to the end of this. The swellings have just about peaked and your skin is beginning to clear. Now it won’t happen instantaneously but things will change quite quickly. After the next week or so I imagine you’ll notice a decrease in the swelling. You might consider a bigger bra in the meantime, in women’s terms you are pretty massive right now. Look, let’s actually measure the cup size. OK, lift up your arms.”
She fed a tape round under my swellings, then repeated over the widest part. She looked at the tape, her eyebrows lifted.
“I think, Harry, even just for a few weeks, you definitely need a bigger bra!”
I didn’t tell Mum and Dad what Mr Carlisle and I had planned. Obviously. I mean I did tell them I was going to be out studying all day, just said I had to do a special project, probably I’d go to the library in the afternoon. Which was partly true. As I was leaving the house, Dad thrust a package into my hands.
“Just a small present, Harry, for your tutor. It’s only a bottle of wine, not a lot really, but we are all grateful for his efforts. You really have made progress, I’m sure, and an awful lot of it is down to him. Oh, and Mum and I may not be in when you get home, Harry. We’re celebrating our anniversary. We’re having a long lunch at the ‘Regency’. Will you be OK?”
I arrived at Mr Carlisle’s house a little early. The thought of actually going out in public was beginning to disturb me. I hadn’t done that for so long apart from my brief excursions, head down, four or five times a week. And in Marion’s clothes too, that caused me concern as well. But at least it was in school-time, none of my friends would see me. I hated to think of the teasing I could get if I got recognised.
It really hadn’t occurred to me to ask Mr Carlisle quite how he knew about make-up, and indeed how he was so good at it. That first time he’d shown me how to do it had surprised me. And I was no less amazed that morning. After I’d changed into my usual lingerie, and put back on my old trousers and sweater, he began to augment the basic make-up I’d done.
“This is probably the best mascara colour for you, Harry. You can get it in all sorts of dark colours, this one is a very deep blue. I think it will suit with the sort of eye-shadow You’ll be wearing. …… OK now, hold still, let me do your eyeliner —- and just a little eyebrow pencil … there, that looks OK. Now I’d thought of a rather darker lipstick, what do you think?”
What did I think? How the hell was I supposed to know?
“OK Mr Carlisle, you choose, I think that one does look all right.”
He very gently and meticulously, with a brush this time and a small pot of colour, spread the deep-ish red paste over my lips, adding another slightly darker colour at the edges.
“There. That’s a lip-liner, it marks out the edges quite clearly, but I think you need quite a thick lip-gloss over the edges. That will look really good.”
I looked in the mirror. Yet again I was surprised, not just at the fact that I was clearly wearing make-up, but also that I was doing so very overtly this time. It wasn’t just a case of trying to cover over my skin blemishes, which had indeed receded in the previous few days. But I was wearing quite heavy makeup, obviously so, but of course if people saw me and thought of me as a girl or a woman maybe that would be OK.
I inspected my reflection. I was just going to make a comment about my hair. It was just a little long by then since I hadn’t dared go to have it cut for several months. But Mr Carlisle was ahead of me. I noticed him getting something from a bag beside the chair.
“Right Harry. The crowning touch, literally. This should do the trick.”
He had a wig in his hands. Oddly enough I’d not really thought about that.
For some reason my own thoughts over the preceding few days had been concerning my own problems, the breast-like swelling, the skin blemishes and so on, and the steps I’d taken, with Mr Carlisle’s encouragement, to overcome them or hide them. I hadn’t really considered my hair. In some way I’d just assumed having slightly long hair would be OK, as far as me resembling a woman was concerned, that is.
“I have to admit, Harry, that I bought this some time ago. Somehow I knew you were heading in this direction, that in some way you’d need to resemble a woman more closely to be able to go out in public. Your natural hair has a reddish tinge. I know it’s mainly mid-brown but there is some red there, so I thought a wig with longer hair, red hair really, would look OK. Are you ready for this, then?”
Mr Carlisle slid the wig on from the front, trapping my own rather unkempt locks invisibly under the ‘cap’.
“It’s quite a cheap wig, really. Even so I thought it would look realistic enough, that it could make quite a difference.”
He took a brush from the dresser and smoothed the long strands down at the sides and the back of my head, returning to briefly tease the fringe into place. He stood back.
I was impressed. Very impressed. I actually looked female, from the neck up at least. The make-up and wig combination worked well together, looking back at me from the mirror was – a woman. OK, a woman, not a girl, I reckon the overall effect of the wig and the make-up had put about five years on me, maybe as much as eight. Definitely a woman.
And as I looked downwards, to see the baggy shape of my sweater and thought about its contents, when the image of my ‘breasts’ came into my mind, yes, definitely a woman.
“I’ve put the top and the jeans in the wardrobe, Harry. If you want to change now? I’m just going downstairs to sort a few things.”
And, sounding very ‘squeaky’ I thought, somewhat excited by all this and yet again seeming not quite right in some way, Mr Carlisle left me in ‘my’ room. To finish my dressing. My transformation, from swollen slightly spotty young man – into a woman. I took the hanger with the jeans and the sweater from the wardrobe, then looked in there again. Why wear the same things again? Why not something else?
By now I was sure Mr Carlisle wouldn’t mind, and Marion wasn’t there to object, she was half a world away. I inspected the hangers. Quite a few of the things in there were not really suitable, pants which I knew would be too tight, sweaters too, but at the end my eyes lit up. I put the jeans back.
There was a suit. A sort-of business suit, jacket and trousers, which looked as if they might fit. I took the hanger out and inspected it. The jacket was a deep blue, maybe it could work, after all I was wearing blue eye-shadow. It had a somewhat mottled appearance, not just plain blue, a bit of a silvery glint to the fabric. Indeed, though I was in no way an expert, it looked quite expensive to me. I looked at the label. It was a designer I’d actually heard of. Not one of the top-notch names but someone reasonably famous. Certainly it would have been expensive. I could wear the jacket over – I reached into the wardrobe again – that blouse. It was a creamy white colour, very shiny, maybe even silk, long-sleeved and hopefully not too tight. Which was good since it would have to cover up my bulging boobs.
I took off my big sweater, and slipped the blouse on. Now THAT felt good. I was sure it was real silk, I really didn’t know why Marion had left it behind after she’d moved. And it fitted too, quite snugly over my shoulders. It had slightly flouncy sleeves and amazingly it wasn’t too tight over my ‘breasts’. I was a little worried when I realised my bra was clearly visible through the fine light-coloured material but if I was going to be wearing the jacket over it, that should be OK.
I picked up the matching pants and then noticed – there was a button missing from the waist-band. I couldn’t wear them, I was SO disappointed. I mean, the jacket was fine, I checked that, nothing wrong with it. Maybe this was why Marion hadn’t taken the suit with her, at least. I still wondered about the blouse, that seemed fine. But – no trousers. Slacks. Pants, whatever. OK so the jeans I’d had on the other day would have to do.
‘Pity’ I thought, I really had hoped to wear something smarter.
Mr Carlisle had hung the jeans up at the end of the rail. I was just reaching out to get them when I realised there was a skirt hanging next to them. A skirt? Well, why not? If I was going to be pretending to be a female so that I could get my project data, I could wear a skirt. Of course I could.
Doubts appeared in my mind as soon as I looked closely at the skirt. Maybe there was another one? But I had a good look at the one in my hand first. The colour was OK, it was a sort of dark blue, slightly denim-like. And the fabric was basically neutral too, probably just polyester or polyester-cotton. But it looked as if it might be too small for me. I took off my own trousers and stepped into the skirt. It was not that easy to pull up over my bum, it really was rather tight. But I did get it on, and fastened at the waist. I looked at the blouse-skirt combination in the mirror. It was rather short but OK, at least it didn’t fit into the ‘extremely short’ category, I couldn’t see the tops of my tights below the hem which was about seven or eight inches above my knee.
And with the jacket? I slipped that on and grabbed one of the two shoulder-bags hanging on the rail inside the door. I looked again.
Perfect. Female. Definitely. I shuddered. This had begun as a practical exercise, it was turning into something more, very much more. I was going out as a woman, OK, but no longer did I just want to ‘pass’ as female. I imagined myself on the High Street. I didn’t just want to look female, I wanted to look good. So there were a couple of other things to consider.
I was hurrying now but still managed to varnish my finger-nails quite quickly and effectively, having seen some of the small bottles in Marion’s drawer. And jewellery. I knew I’d feel better, maybe even look better, wearing jewellery. I was prepared to be disappointed when I started hunting through the largish collection of earrings, they were all for pierced ears. Then I found one gold hoop with a clip on, I desperately searched for the other one, hoping I wouldn’t find it damaged as I had the suit trousers. I found it.
The necklet and rings were easier, not so much problem there, I just slid three gold rings onto whichever fingers they fitted, and slipped one thick-ish gold-effect chain round my neck. It hung there, its small pendant dipping into my blouse. I undid the top two buttons to show it off, enjoying the fact that it revealed – cleavage! I stood up. Ready!
When I walked into the dining room Mr Carlisle wasn’t there. I heard a car engine noise from outside, realised he was backing out. I was glad. Though very confident by now, almost proud of my appearance, I didn’t fancy public transport. I picked up my project folder and put a couple of pens into my bag. Then I had to go back upstairs to get a few personal items from my jacket pocket.
Mr Carlisle came back in and saw me.
“Well Mr Carlisle. Will I do?”
I had expected him to come very close to me, to inspect for flaws, to see if he thought I could pass OK as female. But he just stood there.
“Harry, you look – wonderful.”
I glowed. I was so pleased. I had wondered if he’d make a fuss about what I’d chosen to wear. I thought he might go on about my wanting to wear a skirt, maybe compromising my position and him as well if it didn’t suit, if he thought I wouldn’t pass. But he didn’t. He just stood there. He didn’t say anything, he was just staring. I walked over towards him, probably for the first time really aware of the effect of my ‘boobs’ on my general posture and appearance. The bra was doing a great job of showing them off, even through my blouse. And it was doing a pretty good job of controlling them too, as I walked towards him in the short-ish skirt they seemed to begin to wobble up and down. I got the impression that, walking like that, in short jerky steps, they would have oscillated madly without the bra doing its job.
I was going to say something else when Mr Carlisle interrupted my train of thought.
“Harry. Really. You look incredible. I just thought you’d do the jeans and top, and maybe a little make-up. But this – well, you look gorgeous.”
“Mr Carlisle, really?”
“Really Harry. There is absolutely no way anyone would know. You look totally female. Maybe this is going to be easier than I thought. I was trying to come up with ways of doing the photos and the inspection from the car. Perhaps driving slowly up the High Street.”
“Er – you can’t. I mean, it’s pedestrians only, isn’t it?”
“That’s why I was having difficulty coming up with some sort of plan. But now, really, there is no need. Nobody will ‘read’ you.”
” What do you mean ‘read’ me?” I asked.
“Oh sorry. I didn’t really mean to say that. What I mean is, nobody will spot you as male. nobody at all.”
He thought for a moment.
“Unless of course I call you ‘Harry’.”
“If I call you Harry and somebody overhears, they’re going to be very confused. That could be an issue. So, Harry, just in case, you need a female mane. We’ve not had to think about it before, just the two of us at home if you like, but if you are going out you’re going to need a girl’s name, aren’t you? Any ideas – what would you like to be called?”
So then I had to think. I’d been happy, for many years, with ‘Harry’. There weren’t so many Harry’s around. I was pleased Mum and Dad had chosen that name, not something ordinary like John or Peter. Or even Clyde, apparently that had been in the offing just before I was born. But – a girl’s name? I thought about ‘Harry’. Something a bit similar, maybe, but not too similar?
“All right. There was a girl, when I was in junior school. I used to like a lot, she was called ‘Helen’. Her family moved away, pity really. But the name’s stuck in my mind.”
“OK then. Right, Helen. I quite like that. Ready for off?”
I picked up my folder and ‘my’ handbag.
“Ready as I’ll ever be.”
I was a little nervous even going out of the front door of Mr Carlisle’s house and towards his car. As I approached it, he walked past me – and opened the passenger door for me.
“Let’s do this right from the word go, Helen. Careful getting in, you’re female now. Sit first, then swing your legs in…. That’s right, well done.”
Just sitting in the car as we drove wasn’t too bad, I was somewhat hidden from everyone we passed. But when Mr Carlisle parked at the back of the Council Offices and we had to walk down the narrow street and onto the High Street, my nerves got the better of me.
“Mr Carlisle. I can’t do this. Really. I mean, I want to but I can’t.”
“Helen. Look at me” he said, standing just in front of me. “There is no problem, believe me. Nobody will stare. Or at least, if they do, the men are eye-ing you up, and the woman are just jealous. You look gorgeous. And you’ve come too far now. Not in distance terms, we’ve only come a few miles. But in dressing and making yourself up, you’ve made yourself into a woman. So enjoy the feeling. But remember, we’re here to work. You’ve got things to do. So – OK?”
He took my hand and squeezed it. I realised that people were watching. They had seen what they would see as a symbol of affection.
But nobody came over and started going on at me. for going out in public dressed like that. And – one person, a man, probably in his mid-twenties, walked past the two of us. I saw his eyes move from my legs to my cleavage, then to my eyes. And he smiled! I shivered, but I did realise, I could do this.
Though we’d had some doubts about actually how to do this, my project stuff that is, we had discussed in some detail just what needed to be done. So I did it. I actually walked up and down the High Street, slowly at first. Stopping every few yards to make a note about the buildings on the other side of the street, the style of architecture, the approximate age, the current use.
My project was to be about the ‘Built Environment’ – an aspect of Human Geography, what buildings are used for, how big they are, not just shops of course, offices and flats and houses and so on. Sure I could get some of the data from the Internet, I would have to, but these observations together with the photographs I took as I walked back down the street, they would form the bulk of my study. And as I walked along Mr Carlisle stayed a few yards behind me, basically just window-shopping. We’d reckoned it ought to take just over an hour, in fact I’d got what I needed in about fifty minutes.
“OK Mr Carlisle. I think I’ve done.”
I’d approached him looking in a dress shop, of all places, there happened to be one close by as I completed my task.
“Right, well done Helen. So – what do you think of that? The black one, there.”
I looked in the Roddhams’ window. The theme for the window-dressing seemed to be something like ‘Party-wear’ or ‘Formal evenings’ or something like that. And in the middle of the display was a mannequin – surely that should be womannequin – wearing a tight glitzy silver-coloured top – and an indecently tight, short, black leather skirt.
“How would you like to wear that?” he asked.
I looked again. Basically it was a very attractive ensemble. It seemed a strange word for me to use but that’s what I thought. And I said so.
“And, though I hesitate to say so, Helen, you would look stunning in it!”
I didn’t know how to react to that comment. I just looked at it. It really was a very strange thought, to try to imagine me wearing something like that. So I imagined Holly Tomkinson wearing it. Wow!
“Do you think we’d better be heading home now, Helen?” asked Mr Carlisle.
I agreed, we turned and began to walk back in the direction of the car park.
“Shit!” I muttered.
Though quietly, but Mr Carlisle heard it.
“Helen?!” he hissed, not wishing to draw attention.
“Mr Carlisle. Twenty yards ahead, at twelve o’clock. My Mum and Dad!!”
He was flustered. Probably thinking the worst, straight away. Himself, trusted tutor, found in town with student dressed in women’s clothes. One helluva scandal. But I reacted more quickly, probably a case of needs must. I just had to get by them in some way. They’d just stopped to do some window-shopping of their own so I grabbed Mr Carlisle by the arm and steered him across the road. I let go as soon as I could, and veered into WHS and out of sight of my parents. I hoped.
We spent a minute or two looking at the magazine rack in there. Mr Carlisle was inspecting one about cars, I surprised myself by skimming through ‘Marie Claire’, actually enjoying looking at an article by a celebrity about very high heels and how she didn’t like to wear them but felt she had to. I asked Mr Carlisle to have a look outside, he came back to report that he couldn’t see my parents any more. I breathed an almost-audible sigh of relief when we got back to the car.
As we went into his house, Mr Carlisle did exactly the same.
“OK” I said. “That’s over. I need a drink.”
With a combination of relief and, in a way, regret. It was almost the end of term, after a couple more sessions I wouldn’t be seeing Mr Carlisle for a couple of weeks. No chance to dress myself up – had I really just thought that? And why did I feel disappointed about it?
“I’m sorry, sir, I forgot. My Dad wanted to thank you for all the help you’ve given me. He gave me something for you.” I tripped up the stairs and came back down with the bottle of wine. “You know, we really are all very grateful. Mum and Dad and me, we all are. Even though they don’t know about this stuff today. I’d have had all sorts of problems if you hadn’t been there to help. Thank you.”
I handed over the bottle. And, while Mr Carlisle had both of his hands full, I leaned over – and kissed him on the cheek.
“I hope that’s OK, sir.”
Yet again Mr Carlisle looked concerned. He did smile a little and turned towards the kitchen.
“Thanks very much – er – Helen. Now excuse me, please, now I really need a drink after that.”
He emerged with a corkscrew, and two glasses.
“Join me? After the shock of seeing your parents, you could probably do with one too.”
We sat in the lounge this time, not in the study-cum-dining-room where we’d always done our schoolwork. I sipped the drink quietly, wondering if Mr Carlisle was going to suggest we got on with the project there and then. Or should I change out of my feminine clothes first? And what about the project? If I had another drink or two I probably wouldn’t be able to concentrate. After a few minutes Mr Carlisle offered me another glass of wine. I took it and sipped it, a little more slowly this time.
“Mr Carlisle. What did you mean when you showed me that outfit in that window? Did you really mean you think it would suit me?”
“I meant it, Helen. You’d look knockout.”
“Thank you, Mr Carlisle. That’s a very flattering thing to say. “
“That’s OK. Helen.”
He was staring at me. I was staring intently at him. I had something to say.
“Mr Carlisle. I’ve been coming here for over three months now. OK so you know about my problems. The reason I have to have special tuition, I mean. But I’m a bit puzzled. You obviously are concerned, I suppose that’s why you’ve been so supportive, with me needing to be comfortable and so on. And with dressing up so we could do the project data stuff today. But you’ve never actually asked to see – my ‘problem’. I’d have thought you would have, at some time in all this time, that is.”
Now what I did next wasn’t really a follow-on from that. Honest, it wasn’t. It’s just that I was getting a bit warm, what with all the excitement and the glasses of wine. I just stood up and took my jacket off. Just stretched a little, then I realised that in doing so I was giving Mr Carlisle a clear view of the front of my blouse, and the purple bra showing through it. And of the effect caused by my ‘breasts’. However, I continued.
“I saw my doctor again on Friday. Apparently they are going to start going down. The hormone tests showed that, the skin condition has cleared up, but that was always going to decrease first. Now these – they’ve stabilised, the doctor said.”
Mr Carlisle stared even harder. I felt he wanted to say something but for some reason didn’t dare. I walked over towards him, actually enjoying the sensations I was experiencing as the tops of my tights rubbed lightly against the inside of the hem of my mini-skirt. I deliberately, carefully, took his hand.
“Would you like to see them?”
He gulped. My tutor gulped, visibly. I’d hoped I might relax him by holding his hand but it only seemed to make him more agitated.
“Would you like to?”
“Oh yes. Yes please. Helen.” He was breathing heavily.
“You can call me Harry now, you know.”
“I think I’d prefer ‘Helen’. After all, you are – you do look like – an attractive woman.”
“OK Mr Carlisle. Enough of the flattery. Come here.”
I led him across towards the door, it seemed a good idea to go through and sit on the sofa. There we could be side-by-side comfortably. I began to undo the buttons on the front of my blouse. Mr Carlisle was still staring.
“Oh Helen. They look gorgeous” he said as I pulled the front of my blouse apart to reveal my bra-covered ‘bosom’ in all its glory. “May I – er – feel them?”
“If you’d like to, yes, of course.”
I watched as his hand moved closer and cupped the underside of my right breast. I felt good as his hand began to stroke under the swelling mound.
“Do they, I mean, do they – hurt, or ache? What does it really feel like?”
“Oh, no. They don’t hurt at all. It was odd at first, with the weight and so on, but specially with this kind of bra, well, they’re well supported. They don’t ache at all. In fact they feel rather nice. In a strange way I’ll be sorry to lose them. They’re a DD cup now.”
“Oh my!” muttered Mr Carlisle as his hand began to move further round the breast, and to begin to stroke and feel my left boob.
It felt good. I said so.
“Here, let me show you.”
I un-fastened the small clip between the cups of the bra, releasing my boobs. They sprung outwards a little, free from the tension of the bra. Then, suddenly, they sprung outwards a lot.
“Oh my GOD!” exclaimed Mr Carlisle. “They are just so beautiful, Helen.”
I didn’t reply. I couldn’t. I was tingling. It wasn’t just the breasts which were excited, a shiver was going through my entire body. This was something new. Someone was actually – fondling – that’s the only word for it – my breasts. And rubbing his fingers over my nipples. And my nipples were going wild. I’d felt something like this the previous week while the doctor was measuring things, but this was better. Bigger and better. I was shaking with excitement.
“Oh wow. Sir. That really does feel good.”
I looked down, I didn’t really need to but I could feel something extraordinary was going on. Blood was coursing through to my nipples. They were swollen and seemed to be turning a much deeper red colour, they were suddenly so sensitive. I could feel so much pleasure as Mr Carlisle stroked them gently.
“I don’t understand. Why is this happening?”
I think I was almost crying, the waves of pleasure were so exquisite. I looked up. Mr Carlisle was sitting there, stroking gently. A tear began to roll down his face. I couldn’t help myself. I’d kissed him on the cheek earlier, this time – I just had to – I kissed him. Once, very lightly – on the lips.
He jolted backwards. As we parted, his hand stopped moving. We sat very still for a minute. I fastened my bra and buttoned up my blouse.
“Helen. Harry, that is. I know it’s nearly the end of term. Look, this shouldn’t be happening like this. It isn’t right. I’m sorry. I’m going to ring your school tomorrow and suggest they arrange for a different tutor next term. I think it would be for the best. “
Which is exactly what I didn’t want to hear.
“Because this isn’t right, Harry. Though it’s OK to get involved with a student’s problems, a tutor should be interested of course in order to provide support. And I am. But I’m rather worried – what this could lead to. I think you’d better go and change now. I just hope we can continue until Thursday, we really should get this project sorted before the end of term.”
I was really disappointed. I mean, the day had all gone brilliantly, certainly as far as I was concerned. I got up to go up and change.
“Mr Carlisle. I do understand some of what you’ve said, but, hell, things seem to be going so well. And if it is the dressing-up which is worrying you, maybe I can see why. But I don’t have to. If my condition is going to improve soon there won’t be a need to, will there?”
“Harry. Please. Sit down for a moment. There’s something you should know.”
I sat. Mr Carlisle cleared his throat. He was obviously going to say something very important to him but had some difficulty in starting out. I was unsettled too, obviously.
“OK then. But please, before you start, do you think I could have another glass of wine?”
He got up and poured me another glass. I sat and crossed my legs again, and sipped it slowly. I knew I had to listen.
“The trouble is – Helen – you look so fucking sexy, if you’ll excuse my language. I’m sorry but I don’t know another way to put it, to express what I think. I just don’t know if I can trust myself. Hell, I’m not saying this right. Helen, do you know what a transvestite is?”
“Yes I do. And I do realise, though I hadn’t thought about it, right now I’m really a transvestite. Dressed like this, I mean.”
“Well, for several years now, since not long after my wife died, I’ve had a ‘thing’, some sort of obsession, with transvestites. Not in a big way, you understand, I’m just fascinated. I like to look on the Internet, look at their web-sites, pictures of men dressed up and so on. Some of them look very convincing, very sexy indeed. “
I sipped my wine. OK, young and somewhat naïve I may have been but I was beginning to understand Mr Carlisle’s situation. And why he had helped me initially, with the ladies’ lingerie and so on.
“I have admit, I’ve been ‘playing with you’ to an extent over the past few months. Helping with make-up and clothes and so on. And when I saw you this morning, in a skirt for the first time, well, you probably wouldn’t understand.”
“But Mr Carlisle ….” I tried to interrupt.
“Harry. Seeing you dressed and made up like that, in your short skirt, I was sexually aroused. And that’s not a good thing for a tutor to be with a student. I knew I had to go ahead with our outing but – since then – I think things have begun to get out of hand. I’m afraid – this has to stop.”
I got up and walked around a little. I had to think. This did explain a lot. How Mr Carlisle had been able to help me with the make-up and so on, how he had been able to do it so well. And the frequent looks he’d given me, maybe not quite the looks from tutor to student. Basically, he liked ‘Helen’.
It was then I realised how my own slant on recent events had changed. I liked being Helen.
“Mr Carlisle. You said you don’t really trust yourself.”
“Yes. That’s right.”
“Do you trust me? I mean, you’re older. Older and wiser, as they say. And maybe with all the transvestite stuff I didn’t really realise what was happening. But – I like being like this. Today has been a wonderful day, maybe except for seeing Mum and Dad in town, that was scary. But just being out, and being looked at, I’ve enjoyed it. So much. And I may be younger than you but I do know what I’m doing. Maybe it would be best if I stopped dressing up, especially if my symptoms are going to subside. But I’d still like to continue the sessions next term, at least until I can go back to school.”
Mr Carlisle sat thinking for maybe half a minute.
“OK Harry. I won’t ring the school yet, we’ll see how the next few days go.”
I turned and went up to Marion’s room to change. That evening Mum and Dad were late-ish home. I did myself a snack. I was just sitting, thinking about how things had developed, waiting for them when Jake turned up at my door. Jake was just about the only real friend I could trust in school. He was the only one I’d told about my own problems in any sort of detail. But even with him I still wore the baggy sweater. And I’d never shown him my MPMs.
As soon as he arrived I realised. The image of my own earrings, worn that morning, for the first time, shot into my head. Or rather Marion’s earrings.
“Jake! You’ve had your ear pierced!”
“OK, Harry. Cool, isn’t it? Rib me if you like, but it worked.”
“Yeah. Real cool, it worked on Holly. I’m taking her to the Christmas party. Friday. At the ‘Dragon’. Do you think you’ll be able to come?”
I’d known he would ask me that. Jake kept going on about how my mates would understand but I knew that wasn’t entirely true. Like in any class, there are some all too willing to poke fun at anyone different, whether he has thick glasses, or he’s black, or – whether he has big swollen tits. It just wasn’t on. I still had to stay out of sight.
I changed the topic again.
“So – where did you get your ear done? Was it painful?”
“Only a bit. My mother did it. Cheaper that way of course.”
At which moment Mum and Dad appeared.
“Hello Jake, how’s things?” asked Dad.
“Fine, Mr Davies” replied Jake.
“OK at school? Did you get your Geography project started, Harry’s been doing his today?” added my mother.
And, as she did so, for a reason I just couldn’t see, my Dad smiled as she asked.
“Sure, I got it in last Thursday. No problem.”
“Harry, you were doing yours this morning with Mr Carlisle weren’t you?” queried my Dad.
His smile grew.
“Er – yes.”
What was this about? Surely he hadn’t …… No, of course not, his reaction would have been much more explosive. But something was going on I didn’t know about.
“We reckon Mr Carlisle has had a busy day, Harry. We saw him in town this afternoon, after we left the restaurant.”
“Oh. Did you?”
Maybe they’d just seen him, not noticed me.
“You remember he said he has another student, Harry. A girl, I think he said. Well we saw her. She was obviously doing some project or other, like you. She had a clipboard, you know, a bit like yours. They were just off the High Street.”
“Was she?” I replied, rather weakly, not at all sure where this was going.
“Pity you’ve not met her, Harry” continued my Dad, smiling even wider now. “Drop-dead gorgeous, she is.”
“Jim!” exclaimed Mum, not too sure about her husband saying things like that, clearly about a young woman or so he thought.
“Well, she is dear. Very attractive, at least. Long red hair, tight top, short skirt, you’d like her, Harry. And gorgeous tits”
My mother was almost shouting. But she wasn’t really embarrassed, she was smiling too.
“Jim, I think we’d better change the topic. Jake, I’ve just noticed, you’ve had your ear pierced.”
Jake told her about it, about his Mum doing it, said it hurt a bit but not a lot. He didn’t mention Holly Tomkinson. I was still recovering a bit from my Dad’s comments, I was really glad I’d spotted him and Mum in town. Clearly he had noticed me and Mr Carlisle. And if he’d got up close to us…… I hated to think. I moved onto the new topic of conversation, suddenly keen to take advantage.
“Maybe your Mum would do mine, Jake. Do you think?”
I waited for my own parents’ reaction. They surprised me, I might have expected some hassle. I struck while the iron was hot. Within forty-five minutes I’d gone back with Jake to his house, up the road and round the corner, chatted with his Mum, had BOTH my ears pierced and small ‘sleepers’ put in, and walked home again. It was dark by then, I was OK with that, specially with my big padded coat on. No problem.
Mr Carlisle noticed, of course, the next morning almost as soon as I’d walked in. But he didn’t make any adverse comment, just muttered something like ‘very nice’. For the first time in several weeks I didn’t go up to Marion’s room to change or anything. And we didn’t say much about the events of the previous day at first, not about the subterfuge I’d used in order to collect the data for my project. We did deal with the data of course, even though I was supposed to be doing Biology that morning. But he did say something about ten minutes before we were due to finish, we had in fact reached a suitable stopping point.
“Harry, I think you were wise, not to dress up or anything today. We have to get things back on a professional footing, there really could be problems otherwise. Please, what I said, about my liking transvestites and so on, you won’t mention that to anyone, will you?”
“No way, Mr Carlisle. Nobody at all, not mates, not family, nobody.”
I wondered whether to say anything about my Dad’s remarks. I decided I should. He looked rather horrified when I told him, then grinned at the ‘gorgeous tits’ comment.
“Harry. I think we got away with it. And, though I shouldn’t say this but it was worth it. From what I’ve seen that’s going to be a damn good project, maybe an ‘A’.”
Dad was pleased when I told him that.
“Well done, Harry. This tuition thing seems to be working very well. Finish on Thursday, isn’t it? Oh yes, while I remember. On Friday Mum and I are off out again. For the night this time. Remember that hotel we had lunch at? They’ve sent us a special offer, so we’re re-celebrating our anniversary on Friday, which is the actual day. And staying there overnight. Will you be OK on your own for the night?”
Friday. So I’d be on my own. Mum and Dad having a sort-of dirty night of it reliving their wedding night, Jake and everyone at the ‘Dragon’, and me at home with the TV. Oh well.
“Sure Dad.” I could have said more, but I didn’t.
A couple of days later, at the end of our session, Mr Carlisle and I had sorted out the stuff I was going to do over the Christmas holidays.
“Maybe you’ll be – partly at least – back to normal by then. Physically, that is. Anyway, Harry, have a good holiday. See you in January.”
Mr Carlisle came to the door with me. I was just about to go. But there was something else I’d been thinking about, wondering whether I should say anything. I decided I had to. There may never be another chance. I turned to face Mr Carlisle.
“Sir. Just one thing.”
“I enjoyed Monday.”
Mr Carlisle paused.
“So did I.”
I hesitated again.
“Look, sir. You said you like transvestites, you’ve looked at web-sites and magazines and so on. Well. How would you like – to take me out? “
I stuttered. No. Not that, not go out with Harry.
“I mean – take Helen out. On a date, just out to a pub maybe. Would you like to?”
“Well, I’m not sure about that….”
“Oh go on, Mr Carlisle. Look, on Friday Mum and Dad are away for the night.”
I went on to tell him why, it wasn’t really any sort of secret. And I told him about the party. The one I couldn’t go to. The one where Jake and Darren and George would be getting very tipsy, and Jake would end up feeling up Holly’s mammoth jugs, at least he hoped he would. And there was me, with the television.
“So. Friday. How about it?”
He looked at me. He thought. I mean, I KNEW he wanted to but he was hesitant. A big step, and with a student too.
“Well, since Marion’s due back on Monday, this would be the last chance. The only chance really.”
“Marion? Your daughter?”
Quite why I asked that, I just don’t know. He was obviously talking about his daughter. After all, she is the only Marion we had in common. In a sense.
“Yes. She’s flying in on Thursday night. I think she’s staying with a friend near Heathrow for a few days. “
He stood still. He was thinking.
“OK Harry. You’re on.”
I was pleased. Obviously. Like I said, this may be the last chance. And going out on Monday had been SUCH a thrill.
“OK, Mum and Dad are off about half-seven. How about I come here at half-eight, you can help me to do my make-up again, and I can wear that top and skirt again if you like. We could get to a pub about half-nine or ten just for half an hour, maybe an hour. How does that sound?”
“You’ve thought this through, Harry, haven’t you? I bet that’s why you had both ears pierced, so you can wear one of Marion’s other pairs of earrings.”
“No, sir. Not at all. Sure I’ve been thinking about this, but only since Dad told me I’d be on my own tomorrow night. The ear-piercing, well, it was Jake prompted that.”
For the rest of the day I was on tenterhooks. I was worrying that Mr Carlisle might ring up and cancel. It was just after eight when the phone rang and Mum answered it.
“Oh hello Mr Carlisle.” I heard her say.
Bother! He’s thought twice about it.
“No, don’t mention it …. Yes, we really are very grateful …. Yes … Yes, he’s here, one moment.”
Mum called me from the hall.
“Harry, it’s Mr Carlisle. He’s just rung to say thanks in person for the wine. He’d like a quick word, Harry.”
I took the phone as Mum went back towards the kitchen.
“Harry. Can you speak?”
An odd question really, then I realised. What he meant was ‘Can anyone else hear you?’ I pulled shut the door from the living room and spoke quietly.
“OK, go on.”
“Harry. I’ve been thinking.”
And he didn’t sound as if he was going to pull out. There was a bit of an excited tremor in his voice.
“You said your friends are going to their party at the Dragon? I assume that’s the Green Dragon, just off the by-pass. Well, they’ve got a separate lounge there. It’s a bit upmarket, it’s well away from the Function Room. I just wondered if – if you’d like me to take you there – as Helen that is. If that’s OK. So maybe you could get here a little earlier, so that you have some time to prepare and so on, I’ve got something a little special for you.”
I had to think quickly, obviously Mr Carlisle had been doing just that. I spoke quietly.
“But what if someone recognises me? I mean, they might, Jake or somebody, I don’t know, Mr Carlisle.”
“Harry. I promise you. Nobody will. I mean, your parents didn’t the other day, did they? And really dressed up for the evening, there is no way will anybody recognise ‘Harry’. Trust me.”
I did trust him.
“OK. So, about eight then?”
“Great. And, just so there’s an excuse for us talking, don’t forget your Biology homework this holiday. OK?”
Mum and Dad accepted the excuse when I told them, and went on a bit about what a nice man Mr Carlisle was, calling to thank them like that. I was still nervous about him ringing to cancel, all through the next day. But I have to admit my excitement level rose, even though it was high to start with.
‘Something a bit special’?
What did Mr Carlisle mean by that? It had to be something to wear, jewellery maybe, or a different top to wear with the skirt I’d worn before? It was just a few minutes after eight when I arrived at Mr Carlisle’s front door. He greeted me, obviously still rather excited himself.
“OK Harry, let’s get straight on with it. I’ve got all the clothes ready, in Marion’s room of course. Come on, let me show you.”
I followed him up, and I really did gasp in amazement when I saw the garment hanging there on the outside of Marion’s wardrobe.
“Mr Carlisle! Is that – THAT skirt – and the top as well?”
I could see it was. The black one, from Roddhams’ window. The one we’d seen a few days earlier. And the shiny silver top too.
“I said I thought it would suit you. Just the thing for an attractive young lady to wear on a special night out. Which this is, of course. I really did think it would be a good idea not to borrow any of Marion’s things. I don’t think she’d realise, but just to be sure.”
I was speechless. Literally. I just touched the skirt, I slid my fingers over it, and over the sheer material on the sleeves of the blouse. I revelled in the texture and the shape of the bodice. I goggled at the incredible plunge neckline.
“You want me to wear – THAT!”
Of course I wanted to. It was beautiful. Shiny and silver, a clingy material which would obviously show off my ‘assets’.
“Well, Harry. Let’s see what it looks like shall we? But I really did think you might want to, after all this may well be your only chance.”
“Mr Carlisle. Don’t try to tell me you’re going to claim that on expenses.”
I smiled, he laughed too.
We settled down to prepare for the evening. Mr Carlisle had assembled the cosmetics on the dresser. From what I could see he had been spending, I recognised the brand names of several of the items. This wasn’t cheap stuff, he’d gone for up-market cosmetics too. I shivered yet again at the thought.
And the surprises didn’t end there. Mr Carlisle had a rather self-satisfied smile on his face when he opened the wardrobe and removed a large bag . The first item he pulled out to show me was a new lingerie set, not purple this time but black, and very exotic. It seemed so sheer to me, so smooth, black and ever-so-slightly lacy round the top edges, of the bra and the thong, each with a small jewelled insert, on the bra just above-left of the left cup, on the thong it was on the left too, near the top. They looked lovely. And it had a garter belt too. And stockings.
“Harry. Believe me. Every transvestite in the world, every single one of them, totally loves wearing stockings. And you’re going to look great in them. Now, let’s begin to sort things. I think it would be a good idea to get the make-up done first, but you may like to shower before we start. We have to get you smelling sweet.”
He handed me a robe. Not a pink one, at least. My change-over was about to start but hadn’t started yet. I was still male, still Harry.
“OK, Harry, you have a shower. I’ve left some things in there, gel, foam, whatever. It’s called ‘White Linen’, it’s a famous fragrance. Something I used to like to buy for my wife though she wasn’t awfully keen on it herself I must admit. And a razor and things. You go and sort that. I’ll shower in our room – I mean my room – and get changed myself. OK?”
“Sure, Mr Carlisle ” I replied.
He left to do his own thing and I set to my own preparations. I had shaved already that day, twice, but after showering I did so again. I felt clean. Refreshed. And indeed sweet-smelling. Back in ‘my’ room I stepped into the black thong with its diamante motif, somewhat surprised but delighted that it did its job rather well, its extended job that is. Not just of covering what it might have been expected to cover if worn by a real female, but also that it just about managed to compress and hide my – extra bit!
I slipped my bra into place and noticed it didn’t have any shoulder straps. I clipped it in the centre, then adjusted the cups. Of all the items I had tried, and in fact the ones which came after, this was so definitely the best. The very best. Simply, because it worked. It did its job, or rather its jobs. One, even though it was strapless it supported me in a way none of my other bras, not Mum’s sports bras, not the purple one Mr Carlisle had got me, had managed to do. My MPMs nestled snugly in the bulging cups, the stiffening and the under-wiring working together to support my bulging boobs. I resolved, there and then, whatever happened that night, to get Mum to get me one just like it or at least get one myself. Maybe in white. Mum would probably not be happy with me wearing a sexy black bra but this one was SO comfortable.
And two, it looked good. Now that aspect, I wasn’t at all sure I could convince my mother of. I checked its label.
‘Black poly/cotton Bra, 40-DD, Padded, Strapless and Under-wired, Plunge, Diamanté motif’.
And plunge it most certainly did, the edges of the cups just manages to cover my enlarged nipples, and in the middle – wow. A cleavage, and what a cleavage. I stood admiring my figure in the mirror for a few minutes.
The suspender belt, by comparison with the rest of my lingerie, was easy to put on. But the stockings, well! They were labelled as ‘Nearly Black, 10D, seamed’. They were incredibly sheer, or so it seemed to me. And they felt just plain gorgeous. As I heard Mr Carlisle coming back, I quickly put the robe back on, gathering it at the neck. I wanted to surprise him with the effect of my lingerie, but not yet.
“All right, Mr Carlisle. Barbie doll time again?”
We’d joked earlier about why Mr Carlisle had liked to dress me up. I’d made a comment, something about him having a full-size Barbie doll to play with, to make up, to in some way ‘make’ a woman. It seemed a rather insulting thing to say, both about him and about me in a sense, but we both knew we were playing at something. That hadn’t been serious. And now, this was. I was going to be his real-life Barbie, his escort for the evening.
“I thought the better-quality make-up might be a good idea, your skin seems so much better now. No need for the medicinal stuff, is there?”
Of course, he was right. No need at all. And good though Mr Carlisle’s previous efforts had been, he did an even better job on me this time. He actually showed me a full-page print-out, one which showed a woman – or rather a transvestite – he’d found on the web. The image showed very clearly the sort of make-up he had used and the effect it produced. He was using that picture as some sort of model for me, changing things a bit of course but basically going for that ‘look’.
Well, it worked. After less than a quarter of an hour he’d finished doing my face. When I looked in the mirror I wasn’t that impressed, the hair and the robe didn’t look at all feminine. Basically I looked like a young man with make-up on. And a rather silly one at that.
“OK, let’s try the wig, Harry.”
That made a big difference. I looked again, at the same face, big dark eyes, smooth skin, thick lashes, cheeks lightly highlighted with blusher and all augmented by the same red wig I’d had the previous time. Well, there was a definite feminine feel to the whole ‘look’. We were getting close.
“I thought a darker lip colouring this time, Harry. This dark red will match your nails. ”
Mr Carlisle showed me the pack of longish, stick-on false nails.
“OK, shall I do the mouth now? Then you can show me the full effect, lingerie and all.”
But I really didn’t have time to comment – the phone rang. He seemed annoyed. He was obviously enjoying himself, wanting to see my reaction when he showed me things. But he was interrupted, mid-enthuse, by the phone ringing downstairs in the living room.
“OK. Back in a minute, Harry.”
I didn’t want to look at the other stuff Mr Carlisle had bought for me, I didn’t want to spoil his fun in surprising me. But, when he came back up about three or four minutes later, the smile had gone.
“Harry. Sorry, problems. That was my Aunt Harriet on the phone. She wants me to go over and fix her electricity. Her power has gone off again. This has happened before, it’s only her circuit-breakers but she can’t reach them.”
“Where is she?”
“Just the other side of Halesowen. It takes me about fifteen minutes to get there.”
“And how long to fix it?”
“About a minute. Longer if I let her give me tea. I am SO sorry, this has ruined the evening.”
“Why? I can still change, can’t I? Now that you’ve done the make-up. It should take you about forty minutes, if you drive carefully. There’ll still be lots of time when you come back. If it’s all right, I mean, me stopping here – on my own.”
Mr Carlisle thought for just a moment. He didn’t take long.
“OK” was all he said, disappearing from sight rapidly.
I heard his car start up a minute or so later. I looked round. Mr Carlisle had gone to a lot of trouble. But, if he was an admirer of transvestites, if he liked the dressing-up and make-up stuff, then he’d probably had a lot of fun, planning things and shopping and so on. OK, so now to add to the fun, to really have a good go at this myself and – I shivered once more at the thought – to be his transvestite date for the evening.
I emptied the bag out onto the bed and began to look through its contents. One item was obvious – a shoebox. As always I looked at the label first – ‘Black Patent Classic Pumps, style Stephanie, heel 6 Silver Gloss.’ Then I opened it and took the shoes out.
They were beautiful! Which is a word I’d never ever used about a pair of shoes before. But this pair were, such high heels, oh-so shiny and with black ankle straps with silver-coloured buckles. I wondered how on Earth I was going to get them on. And even if I did, would I be able to walk in them? The sense of anticipation grew as I looked at the other items from the bag.
I’d had a quick look at the rest of the items Mr Carlisle had got for me, I knew the fingernails, stick-on false ones of course, would take some time. However, I was ready for the main feature, or rather features, the silver top and the tight leather micro-skirt. The first wasn’t as easy as I’d thought it would be – until I worked out just how to do it. Or rather how to wear it. The fabric was silver-coloured and stretchy, a little like old-fashioned ‘chain mail’ but much finer. I slid my arms in and pulled the two halves of the front together, then had difficulties, my long red nails again, coping with the tiny zip up the front.
Eventually I got it zipped up, and spent some time arranging the sleeves and the bodice to properly cover my bra. When finally I was satisfied that I was wearing it correctly I turned to the skirt. The black leather was rather more flexible than I’d imagined it would be, this time it didn’t take me long to pull and zip it up, just about managing to encase my bum and cover the tops of my stockings.
Then I tackled the jewellery, there were two small boxes, the sort of padded packaging used for that sort of thing. The first was – well – cheap. It even still had its price ticket with it, it was a ‘Dress Ring Multi-pack’. But I wasn’t disappointed, not at all. £2.99 for what was basically a pack of ten cheap, rather flash dress rings, assorted, not gold or silver of course. The silver-coloured metal ones were probably steel, the gold ones would be maybe brass. And all the ‘stones’ were glass, of course. But they actually looked quite good. OK, four of them looked awful, and one was badly made, the ‘stone’ was stuck on way off-centre.
But I chose five of them as ‘acceptable’, all with silver-coloured settings, and fitted them onto whichever fingers they fitted. The result was – more than acceptable. Now I didn’t know exactly what sort of criteria a woman might use in choosing rings, what type, what should go where, what combinations worked and what didn’t and so on. All I knew was that the result looked fine. The five rings enhanced the appearance of my hands, added to the effect of femininity created by my elongated deep-red fingernails.
But the second box – that wasn’t cheap. Definitely not. You could tell – the black padded package was of a substantially superior quality. And so were the contents. None of this ‘Multi-pack’ stuff. The box contained a necklace, and a pair of earrings. Proper earrings, that is, not clips. And these weren’t brass or steel, whether they were real silver or just silver-plated I didn’t know but they looked good.
I wanted to wear them. Big, pendant, diamond-like earrings, with the little hooks pressed through my piercings they dangled about four inches below my ears, glittering and sparking as my head moved slightly from side to side. I could feel the weight, I could ‘feel’ the attractiveness when I saw them in the mirror. Even with my newly-acquired long fingernails I managed to fit them quite easily, but the small clip on the matching necklace, that took me several minutes to negotiate. Eventually though it just clipped into place.
The overall result, as the heavy gem-studded centre of the necklace nestled against my chest, at its lowest point just dipping into the very top of my cleavage, was very satisfying. Real diamonds even? Maybe. Logic told me Mr Carlisle hadn’t just bought this for me to wear for the evening. This had to be his wife’s. I felt strangely ‘honoured’.
I realised that the fiddling with the jewellery had taken time. Mr Carlisle would be back soon. All I had left to do, basically, was to put my shoes on. It’s strange how packets and boxes and labels intruded into my life that evening. Basically, I suppose, providing information about their contents which was not at all obvious to a member of the male half of the species. I looked at the shoe-box again.
‘Heel 6 inch Silver Gloss’.
High heels. Very high heels. OK, if I was to play the part fully, the part of a sexy woman, I had to try this.
I stood the two shoes beside my feet by the bed and slid my feet into them. The fit was as near perfect as I could have hoped for. I’d mentioned to Mr Carlisle that Marion’s shoes, the other pair I’d worn, were basically OK but just a little bit tight. He’d obviously taken that into account in choosing these. But where the hell had he got them? I just couldn’t imagine myself, Harry that is, going into a shoe shop and buying a pair of Ladies’ shoes. Not a pair like this.
Again the long finger-nails gave me a little trouble as I fiddled with the small buckles on the ankle straps. Eventually the first slipped into place, then the second was easier. Then I stood up. Strange. Very strange. Then I moved, the simple task of moving one foot in front of the other. ‘Walking’ it’s called, but this was a different version of the ‘walking’ I’d been doing for the whole of my previous existence.
This was on my toes, nearly, I wobbled a little. Then I got into a ‘run’, in a sense, took about ten steps across the whole width of the room. This was fun! This was different. And to my surprise, it was nothing like as difficult as I’d imagined. Very quickly indeed, as I tottered back and forth across the room, basic balancing techniques came into play. This was indeed fun.
‘OK, Helen’ I thought. ‘Time to move’.
With my bag in hand, the last of the ‘special’ items Mr Carlisle had bought for me – or should that be for him – I carefully negotiated the stairs and went into the kitchen. A quick glance at the clock told me he was maybe due back in about five minutes. I wanted to make an impression.
Earlier, as he was doing my make-up, he’d shown me some pictures he’d down-loaded of ‘Lucy’, the transvestite he’d used to model my make-up. In different outfits, of course, and in a variety of poses. But one I’d specially liked showed her sitting on a high stool in a bar, legs crossed, chatting to a man who was clearly very interested in her. In fact he’d had a hand on her exposed thigh. Maybe a little later in the evening …. – hell, what was I thinking?
But for now, I could do that in the kitchen. I filled a glass – a wine glass, that is – with orange squash and sat in one of the two high stools at the breakfast bar. And I heard a car outside, braking rather hard. I crossed my legs. I sipped my drink. I waited. The door opened. I looked up and smiled.
“So, Mr Carlisle, how does your Barbie look tonight?”
Mr Carlisle didn’t freeze, he didn’t stare, he wasn’t rendered speechless. He just grinned, extremely widely. Then he recovered.
“Barbie never looked like that! Christ, Helen. You look – stunning!!”
Which was, of course, exactly what I wanted him to say. I sipped my drink.
“So, Mr Carlisle , are you ready? For your big transvestite adventure?”
“I fucking am!”
Mr Carlisle dashed upstairs himself. to finish dressing. It only took him a few minutes, then my ‘date’ reappeared fully regaled in dress suit and bow-tie.
“Mmmm. Handsome” I said, and I meant it.
Insofar as I was any sort of judge of masculine desirability, he fitted the bill. Nice suit, neat shirt, well-groomed. Yes, attractive. Handsome even.
As Mr Carlisle drove us through the town centre and out towards the by-pass, I asked him about his Aunt Harriet, what he’d done, what she’d said. I really wanted to keep the topic of conversation neutral. I had to try to stay calm. This really was about to be a big adventure. Going into town a few days earlier in a skirt had been one thing, but this – going into a pub so provocatively dressed, this was in another league. And the same pub as all my mates at their end-of-term party, well, the word ‘insane’ came to mind. But the danger, the risk, the however-remote possibility of being found out, these all seemed to add to the experience.
Mr Carlisle pulled up in the car park and got out, coming round to offer a hand to assist me in getting out of the car. We walked together towards the front door of the pub. I was glad to get inside the lobby, it was actually quite cold and I was revealing quite a large amount of bare flesh. Just inside the door Mr Carlisle pulled me to one side. He spoke quietly.
“Harry. Listen, this seemed like a good idea the other day. But – really – we can turn round and go home right now if you like.”
I was tempted. This was beyond what we’d done on Monday. So far beyond. Maybe it was going too far? Perhaps we should just drive back and sit in Mr Carlisle’s living room, maybe have a drink or two, flash my thighs at him, that sort of thing? The sensible course of action would be to do just that.
I might have suggesting doing just that if, the very next moment, the main door hadn’t opened behind us. And if Darren Harris, class dork, hadn’t walked into the pub. Obviously nobody had told him the pub’s function room was at the other side of the building, and that you had to use the other door. Or, more likely, someone had told him and the full meaning of the words ‘other door’ hadn’t sunk in.
But it wasn’t just the fact that he’d come into that door that decided me, it was what he said a few seconds later. He actually looked me straight in the face as he came in. And then his eyes moved downwards. Somebody, one of the others in his little party pulled him back, realising their mistake, knowing they’d have to seek out the other entrance.
And as the door swung shut I heard his voice say “Christ Jake. Did you see those tits? Christ they’re gigantic! Wish I could …” and I didn’t hear the rest.
But that was enough. I wanted to do this and I knew Mr Carlisle did too. I moved closer to him.
“Mr Carlisle. We’re going to do this. But remember, none of this ‘Harry’ crap. I’m Helen. And, while we are at it, I suppose I should call you David for tonight. Now, come on, just what you’ve always wanted, going on a date with a sexy transvestite. Like you said, your only chance really – so come on, let’s do this!”
I took his hand and, with our fingers interlocked and with me holding on very tightly indeed, we went through into the bar. Now it would not be true to say that as we entered absolutely everyone turned to look at us and to stare at my boobs and my figure and so on. But, there was a bit of a hush as we strolled across towards the bar, and several men moved out of the way to allow me through. And Mr Carlisle too of course since I was still gripping his hand tightly.
“Half of bitter” he called out as the barman came straight over towards us.
He looked at me. All right, we should have sorted this out in advance.
“And I think I’ll have a vodka-and-tonic this time, darling” I added in response to his questioning look.
Trying to give the impression we did know each other and that, in some way, I didn’t always have the same drink and he’d had to ask me for that reason. And also trying to keep my voice quiet and in some way ‘gentle’.
He paid for the drinks of course, and I settled down on one of the tall stools at the end of the bar, replaying the scene from the kitchen and from the pictures he’d shown me. He leaned over, the noise level in the bar was beginning to rise again.
“Helen, you do realise most of the men in here are staring at you.”
“Actually Mr Carlisle – er – David, I’m rather surprised at how nice a thought that is. And does it make you feel good?”
“Incredible” was his reply.
He just grinned. Stupidly, really, and I told him so.
“David, my darling, stop it. People are going to wonder just what’s wrong with you.”
“I don’t care, Helen. I dare say other guys have had as much fun before walking into a bar with a transvestite, but I guarantee nobody has ever had more fun. And nobody has ever had the pleasure of being with such a fuckable babe!”
And we just chatted, quietly between ourselves, for maybe half-an-an hour or more, commenting on what we thought about what we’d done and what we were doing, both of us being really rather smug about our ‘adventure’. Eventually I decided it would be rather nice to move on just a little, so after David had got us a second round of drinks I took hold of his hand, and began to stroke it gently.
“Helen, please, you really should stop that. Not that I don’t like it, or course, but – oh hell, what’s the use…”
He took hold of my hand and kissed it!
“David. You really do have to do better than that!”
And I leaned over towards him and kissed him! Not passionately, just a sort of affectionate kiss, just for a second or so – but on the lips!
“Is that OK, David?”
He looked round, clearly somewhat embarrassed.
“Helen – wow – you do know what you’re doing, don’t you?”
“I hope I’m exciting you, my darling.”
“You certainly are!”
And before he could say or do anything else I grabbed his hand again and kissed it myself, and then laid it on my exposed thigh.
“Excited now?” I asked.
Mr Carlisle swallowed a little, not totally sure what was going on and to be honest neither was I. There was a definite excitement here, being dressed so sexily in the bar and flirting with Mr Carlisle. But he realised and I did too that time was getting on.
“David, I think we’d better make a move. It’s getting late, I think some of the gang from school may well be coming through to the bar soon, I really don’t want to be seen like this – with you, you know.”
“Helen, believe me, absolutely nobody will realise.”
“Maybe so but ….”
We left it at that and started to get up to leave. I held on to Mr Carlisle’s hand tightly again as we moved towards the exit. As we left the actual bar and were just going to go through the main door, a couple of girls came through from the other direction and turned right. I knew exactly where they were going, and a rather naughty thought came into my own mind.
“David, hang on, back in a minute.”
I released his hand and turned that way myself, following Anna whatever-her-name-was and the gorgeous Holly Tomkinson into the Ladies’ Loo! Of course I didn’t really NEED to go into there, I’d only had a couple of drinks and anyway we were due to be heading back ‘home’ very soon after. But it was just the thought – me, Harry, in the Ladies’. Wow!
I went in and was immediately slightly flustered. There was nobody there. Then I realised, of course, this was different. There were four cubicles in front of me, three had closed doors. I went in the other. Now I could have experimented, tried to pull down my panties and pee and so on but I thought it was better not to try. So I just sat there for a minute or so, I heard shufflings next door. I was inches away from Holly Tomkinson with her knickers down! The thought send a shiver through me but I resisted any temptation to look over or under the panelling in there, I just stayed seated.
Then I heard doors opening and water flushing so I pushed the press-button in my own cubicle and opened the door. I could see two girls with their backs to me, leaning towards the large mirrors in there. And the nearest bum to me was Holly Tomkinson’s. I walked over to stand next to her, opening my handbag as I went and taking out my lip-gloss. I leaned towards the mirror myself and touched up my own make-up, totally un-necessarily but what the hell. I could see Holly clearly, she hadn’t recognised me at all. Well, in that situation, she wouldn’t have expected to see me – Harry, that is – at all.
And I enjoyed the sight, staring in front of me, the sheer delight of being able to look straight down the cavern between Holly’s tits. I made eye-contact with her briefly and smiled a little. Then I realised. She was staring at my cleavage too. I glimpsed across from one to the other, there was no comparison. Holly has the reputation in class of being a very well-developed girl in that department but, looking at the two pairs of tits I could see, she was nowhere. The combination of my swollen MPMs and the tight under-wired bra gave me a substantial advantage in the breast area.
And I could see, and I’m sure Holly could too, that as I leaned over the weight of my ‘tits’ was pulling my bra forward and pulling my tits out! I could just see the deep pink circles of my aureoles jutting out above the top of my dress. It wasn’t just the thrill of seeing them, it was the fact that Holly was seeing them too! I couldn’t resist a slight wriggle, seeing my boobs wobble and seeing Holly gasp in amazement.
I walked out in front of her and the other girl who I didn’t really know, hoping Holly was similarly staring at my too-short skirt and extra-revealing thighs. As I left the Ladies I saw David. He was waiting – and he was talking to Jake!
Shit! Now what? Then I realised that Jake wasn’t alone. He was with Darren, the lad who’d glimpsed me before when he’d come in the wrong door. Actually it was Darren that Mr Carlisle was talking to, though Jake was stood right next to him. I hoped Mr Carlisle was right about my being so well-disguised. I had no choice, I walked up to him and slid my fingers into his.
“Hadn’t we better be going, darling?” I asked, trying to keep calm and to keep the tone of my voice ‘light’.
Both Jake and Darren had turned towards me. And, I’m glad to say, neither of them was really looking at my face. Obviously. That gave me a chance to turn a little and give them a full frontal view, or as near as they were going to get. Mr Carlisle had taken my hint, he began to lead me towards the outside door. I could feel the eyes of the two boys staring at us as we left, and in the reflection from the tall glass panels by the entrance I could see that, even as we walked away, one of them had pushed the door open with his foot. They were both still staring, Mr Carlisle had noticed too.
“I told you, Helen, they have no idea. And they’re still staring.”
I stopped. I turned towards my ‘escort’.
“OK then, let’s give them something to REALLY stare at.”
I still don’t really know why I did it. Just seemed a good idea at the time. I slid my arms up around Mr Carlisle’s neck and kissed him. Properly this time. I angled my head towards his and planted my lips firmly on his, at the same time running my fingers through his hair.
“Harry” he gasped quietly, breaking the clinch and pushing me away. “We shouldn’t be doing this.”
“I’m Helen, darling. Don’t you want to kiss me?”
“Of course I want to.”
I didn’t let him argue any more. I just kissed him yet again, opening my eyes to look back as I thrust my tongue into his mouth and felt his hand move up my thigh in response to my ardour. Jake and Darren were in the doorway, staring, while Holly had joined them and was trying to get them to go back inside. But they were too interested, wanting to see as much as they could as Mr Carlisle’s hand slid up my thigh and began to edge my skirt higher and higher. When I became sure they’d had a good glimpse of my arse and my panties I stopped.
I broke away this time. I just smiled.
“OK, David, darling. Now we can go home.”
Mr Carlisle really didn’t have an answer, he was in shock in a way.
“OK, come on” I muttered, grabbing his hand and pulling him towards his car.
We were both quiet after that. Mr Carlisle drove back in silence, we didn’t even hold hands as we went back into his house. That final event of the outing had surprised us both. First because it had been so unexpected, I really hadn’t intended that at all. And second – it was obvious that we’d both enjoyed it so much. As soon as we went in Mr Carlisle took off his jacket and poured himself a stiff drink. I did too, we sat facing each other, me in an armchair, him on the sofa, recovering. Finally I couldn’t stand the silence any longer. I knew what I had to do, what I wanted to do at least. I moved over to the sofa and sat beside him.
I reached across and pulled on his tie, easing the knot. I took his tie off.
“Helen” was all I said.
I began to undo the buttons on his shirt.
“OK then, Helen. Look – no – wait!”
I paused in attending to his shirt. I sipped my drink again.
“Please, Helen. Don’t get the idea I don’t want you to go on. I mean, that kiss, outside the pub, and sliding my hand up your thigh, feeling your breasts pressed against me. Really that is every TV-lover’s dream. It was lovely, but I’m just worried what it seems to be leading up to.”
“I’m not worried!” I replied, sliding a hand inside Mr Carlisle’s shirt, and pressing my lips once more to his, pushing my tongue into his mouth.
Inevitably he reacted, not this time by pushing me away, quite the reverse. He pushed me down on the sofa, leaning over on top of me and beginning to undo my top, to caress the swelling breasts hidden in there.
“Oh yes, David!”
That really started it. It started both of us off. Or rather it encouraged us, both of us, just to get on with it. Right or wrong, the time for discussions and debate was over. The next kiss was – passionate, there’s really no other word for it. Mr Carlisle was realising an ambition, he was groping a transvestite, and not just groping. ‘Heavy petting’ is I think the right term.
OK then. ‘Very heavy petting.’ His hands were all over my bra, mine were just getting inside his shirt, enjoying and appreciating the masculine musculature. OK, he was no Arnie but his body really did feel good to me.
Then I stopped. We both stopped. We were not alone. We both heard something. Outside the door of the lounge, but clearly inside the house. I looked up over my shoulder, the door was opening. And I heard a voice.
“It’s OK, Dad, it’s only me. I just thought …oh Christ!”
And a woman came in the door. It was obvious. This was Marion. Early.
“Er, hello Marion” said Mr Carlisle, quietly, calmly, surprisingly so given the circumstances.
I couldn’t see Mr Carlisle’s daughter clearly. I was somewhat twisted round on the sofa and Mr Carlisle was still on top of me, my own right leg wrapped round his arse, I’d just been considering just HOW far to go – basically if I wanted his pants off. I think I’d just decided ‘Yes’. But things had changed.
“OK Dad, I’ll be in the kitchen” was Marion’s reply.
The door swung to behind her, I just about heard the other door from the hall open. The kettle probably went on. Very quickly, Mr Carlisle disentangled his body from mine and got up, eager to finish dressing himself and muttering.
“Jesus, Harry” he hissed. “What the fuck are we going to do now?”
I thought. Quickly. I had glimpsed Marion’s face just before she had disappeared from view. And it was not a face showing an expression of disgust or disapproval or anything like that. What she had NOT thought was that she’d just seen her Dad fondling a transvestite. Exactly what she had thought, I didn’t really know. But it wasn’t that.
OK then, if I could be a woman in the Ladies’ loo in the pub and withstand the scrutiny of Holly staring at my face and down my tits, maybe I could do this. Mr Carlisle and I, both of us, we had nothing to lose.
“DON’T CALL ME HARRY!” I hissed, not loudly but very definitely. “I’m Helen. Right, and you’re David. Now get upstairs quick, pretend to go to the loo or something. And go into Marion’s room before she does, re-arrange the make-up and get my guy clothes out and so on. Then get rid of the lipstick on your mouth and come down when her room is decent enough. We’ll sort my clothes later.”
“What do you mean?”
“I mean what I say. Come on, David, work with me here. We can get out of this.”
I turned towards the mirror and began dealing with my own face, wiping the slight mess as well as I could with a tissue and re-doing my own lipstick and lip gloss.
“Come on, I’ve work to do, being your girlfriend. Now scoot!”
I squeezed his bum and shoved him out into the hall, then took a deep breath to cam myself – and went through into the kitchen myself.
“Hello, I’m Helen. You must be Marion. I really am so very sorry about this.”
Marion looked at me. OK, she’d had a bit of a glimpse when she’d interrupted me and her father a few minutes earlier but this time I was given a more complete once over.
“Helen, please, don’t worry. It’s me who should be apologising for interrupting you two.”
She poured and offered me a glass of wine.
“Here, you probably need this. And don’t worry, Helen, I’m delighted. Dad’s been on his own for too long now, I’m thrilled he’s found someone. Have you been – on a date?”
“Just out for a couple of drinks.”
“And, do tell, how long have you two been together?”
We sat there at the kitchen table for a few minutes, enjoying the wine together, while I explained that I’d known David for a few months and that this had been our first proper date.
“So you’re not really an item quite yet?”
“Er – not yet, no.”
“Helen, excuse me but – it’s pretty obvious. I mean you look stunning, really, and no woman would wear a skirt like that or such high heels, or show off her boobs to a man like that – unless – “
She left the sentence unfinished. And there really was no need to complete it. We both knew. Mr Carlisle chose that moment to come into the kitchen and we all sat around for a few minutes more. Marion explained why she’d come back early – apparently the friend she had been going to stay with in London had dashed up to Newcastle on business. Though she’d left the key with a neighbour for Marion and wanted her to stay there and relax, Marion said she didn’t want to stay there on her own. So she’d caught the train to Birmingham and then a taxi and, well, there she was.
“OK, you two. Excuse me being a bit rude but I really am bushed. I’m gonna have to get to bed.”
She kissed David on the cheek.
“I’ll tell you all about Oz in the morning Dad, but I really do need to catch up on my sleep. Good night, you two. Oh, and don’t make too much noise when you come up, will you?”
David looked at me as soon as she’d left. He realised the significance of that last remark.
“Surely she can’t mean – oh cripes, I guess she does.”
I stood up and moved towards Mr Carlisle. David. I kissed him too, just as briefly though on the lips. Then I spoke quietly. And with no little determination.
“David. Look. You wanted to meet a transvestite, didn’t you?”
“Yes, or course.”
I kissed him again, our lips staying in contact for just a little longer.
“And you liked helping me to dress up and make up and so on.”
“Sure I did.”
So I kissed him yet again, this time just teasing his lips open a little with my tongue.
“And you’ve enjoyed taking a transvestite out to the pub tonight, I mean, it was a good date wasn’t it?”
He was beginning to tremble just a little, he knew I was teasing, I think he also knew just what I was leading up to.
“Jeez, of course, it was real fun.”
I kissed him once more, really opening up this time, real French-kissing, he must have realised I was getting aroused too.
“And you enjoyed kissing a transvestite outside the pub, and snogging her on your sofa?. Despite the interruption?”
He was definitely aroused by now.
“Oh my God, Helen, it’s been a dream come true. Really.”
I held his hand and moved it up to cup my breast. And for the first time I allowed my own left hand to move down, to slide between his legs. I felt his erection. I caressed it.
“So, David my darling. You ready? And we have to be quiet. Marion may well be asleep already.”
“Helen, we can’t!”
“We fucking can. And we’re going to. Look, David, in so many ways I’ve had a really confusing evening. I was male when I came here, I’ve been female all evening. And my best mates were rendered speechless at the sight of my tits. And my boyfriend has an enormous erection. And his daughter thinks I want to sleep with her father.”
“Yes – er Helen. But she doesn’t know!”
“Too right honey- can I call you that? But Marion doesn’t need to know. As far as she’s concerned, you’ve got a girlfriend with big tits , long legs and high heels. Tonight, David, I’m her. I’m Helen. You can’t know at all just how good it feels to me to know that it’s me – Helen – who has aroused you. OK, you’ve satisfied a dream tonight. Well, in a way so have I, though maybe I didn’t properly realise it.”
We were still just standing there, holding hands. I picked up my wine glass, sipped the last of it. No, I wasn’t drunk. I knew exactly what I was doing.
“Your daughter is so glad you’ve got a girlfriend. OK so we have absolutely no idea how long this is going to last. You may never see these again.”
I looked down at my bulging tits, straining to escape my lingerie. My swollen red nipples were just peeping out of the top of my bra.
“But I think we have to seize the day. Or rather the night. I want to do this so much, and I think you do too. Am I right?”
David didn’t say anything but his eyes said it all.
“Five minutes, honey?” I said.
I turned and went up the stairs, not to ‘my’ room where Marion was recovering from her long journey but to David’s bedroom. He stayed downstairs doing what was needed, locking doors and seeing to lights and so on. I was standing looking in his long mirror when he came into the room. He moved in behind me and slid his arms round my waist, caressing my breasts once more, teasing the swollen nipples through my top and bra.
I turned and unfastened my top, taking it off and then removing my skirt. While I did so David began to undress himself.
I spoke very quietly.
“Lie down, my darling.”
I eased his pants down and saw for the first time in my life another person’s throbbing swollen erect penis.
“Kiss me, honey” I said.
And he did. David kissed me. As his tongue slid into my mouth, he kissed me deep and wet and slowly while his fingers slid up my thighs, above my stocking tops, and caressed my bare arse. I pushed against his roving fingers and ended up with my face buried in his neck. I lifted my head to look at him, feeling more exhilarated than I think I’d ever felt in my life.
He continued to kiss me sweetly and tenderly on the nose, the lips, in my neck, as his hand moved up to cup my right breast ever so gently. A shudder moved through me, and I accepted his kisses, knowing that once I got my breath back I would enjoy the next step of my seduction. And his.
Hardly thinking, I let my own scarlet-taloned hand drift downwards until it reached the curly bush of David’s pubic hairs. I slid my fingers into the tight curls and felt them touch the tip of his penis. It was firm and hard, but certainly not totally aroused yet. I ran my fingers along its length, then slid them back and forth, feeling it hardening and thickening as I touched and moved and caressed it.
“Oh hell, Helen, that’s – amazing!” David sighed as his hands stroked my exposed bum.
I lifted my head and looked him in the eyes.
“Ready for more, lover?” I whispered.
“What do you think?” he replied, somehow grinning and moaning at the same time as my fingers continued.
I stroked and rubbed his genitals with my fingertips, feeling his scrotum tightening in my hands. And that, together with the lovely low moans, sighs and grunts he was making made me feel fabulous. Made me feel – girly. Somehow, I felt even more girly than I had done all evening. I wasn’t just playing at ‘girly’ now, I was actually being – a girl. A woman. And a girly thought crossed my mind.
‘I’m going to suck David’s cock.’
My face was so close to his now-full erection. I was so close I could see the veins, the way the foreskin was stretched by the size of the purplish coloured glans and the wet pre-cum beginning to ooze out. I moved a little so that I could get my glossy red lips to it and then ran my tongue along its entire length. I carried on licking his shaft from the base right up to the swollen tip sticking out from what looked to be an impossibly-stretched foreskin. Each time I licked it David’s body seemed to jerk a little, his erection throbbed and wonderful tremors of excitement went through my entire body.
“Is that ok honey?”
“Oh God, Helen, yes, it’s great,” he moaned as he groped my exposed bum. “Just keep going – just like that!”
I did, but now I went all the way. I wiggled my body a bit so I was laying on one side with his erection just inches from my mouth. I was holding his shaft in my right hand, revelling in the pulsating warmth that was filling my palm, and I was cradling his balls in my left.
I was surprised. Amazed. Delighted. I can’t say that, in the whole lead-up to this even, I hadn’t had my doubts. I’d been straight. A straight guy, that is. What was I now? How would I describe my sexuality, and indeed my sex. A gay guy? Maybe. Or a straight girl. The whole thing just seemed to be coming so naturally and easily to me. Despite my thumping heart I tried to relax.
I moved even closer to David’s cock. I opened my mouth and I tucked my tongue down a bit, then edged forward to slide the bulbous head between my lips. I could hardly believe that I was – in a sense – being a woman sucking a cock. I wrapped my lips round it and then with a slithering movement I took my boyfriend’s cock as far into my mouth as I could. I held it in my throat for a moment or two and then slid my mouth up again so that it almost came out.
My ‘girly’ instincts seemed to be guiding me, almost intuitively I seemed to know what to do. I moved my mouth up and down, licking sucking and slurping as I revelled in the sensations in my mouth. I adored the near convulsions in David’s body, his moans, sighs and grunts as his hand roamed over my lingerie-clad body.
I knew he was near, very near. I took it right out, then licked all round the knob and the slit.
“Oh Helen, Helen, yes, yes I’m cumming. I’m so near,” he croaked.
I sucked and licked it, loving the very evident tremors as his cock began to show signs of the forthcoming ejaculation. Then, as I slid my mouth once more up his hard length his body bucked and he started to cum. A jet of sperm shot out and hit the back of my throat, followed by several more.
‘Yes’ I thought.
“YES!!” David shouted.
For a moment I was worried. Surely Marion had heard. I didn’t care. I sucked, slurped and swallowed every cubic centimetre of David’s hot sticky semen.
“Oh Helen, I’m sorry, I’m so sorry,” David groaned as he tried to pull away.
I felt the huge cock in my mouth wilting, and moved my lips back.
“David! Don’t you dare apologise! That was – sensational.”
We lay there, sated lovers, caressing, for several minutes. We kissed. I realised that he wasn’t sure what might happen next but – I was sure. I reached down and began to fondle David’s cock, to my surprise it began to swell and to grow very quickly indeed. I stared at the growing organ, then looked into David’s eyes.
“Fuck me, David!”
“Oh hell, Helen, are you ….?”
He realised. I was sure. David began to roll towards me, a moment later I felt his penis against me, gently testing my bum-hole.
At first I thought he would just penetrate me quickly, but he spent several minutes slowly pushing ever so gently into me, never penetrating more than a few millimetres. Opening my eyes, I looked into his, and he was smiling a gentle smile, enjoying the moment. I smiled back, knowing that this was going to be another intense moment for both of us.
David paused, grinning now, and then with a sudden movement he thrust his cock into me deeply. I gritted my teeth, and winced as the muscles of my bum accommodated his length and girth. There was pain – yes – but for just a moment my arse-muscles failed to restrain the reflex to push his cock out. Somehow their sensitivity seemed – directional – and ‘they’ instructed my brain that this was wrong. David urged his weight down as he rolled on top of me, throwing my nylon-encased legs over his shoulders, and pinning me down. He held his cock inside me for several seconds.
“Is this what you want, Helen?” he asked.
My eyes were closed as tears began to come forth. I was worried – was this spoiling mascara? I realised that, if that was the only thing concerning me, well – I was in a good place. Literally. Under my boyfriend.
“Oh God, yes” I stuttered.
I still had my eyes closed when I felt David’s weight shift forward, and I felt his lips against mine once more. Trying to relax as much as I could, I opened my lips to let him in. The pain in my bum was still there, but I felt it subside slightly around him, and instead of holding me down, I felt his hands at my sides, clasping my hips as he pulled out slightly and starting making love to me.
I had known the pain would be there, but now I relished it, and the fear as I lost control, giving my body completely over to – my lover. He moved forward, propping me up slightly with his knees facilitating a deep entry, and began a steady rhythm, his breaths getting shorter and sharper. I groaned with each thrust, knowing it would arouse him, then I gasped at the deepest point of his penetration, feeling him move faster and faster. I hadn’t expected him to last long after the oral sex, and I wasn’t disappointed when only moments later he drove himself deep into me. He moved his weight onto me again, and with a twitching of his cock, ejaculated into me. I stared into his eyes as he froze with me, his eyes searching mine.
“Yes, honey. YES!!” I muttered as I felt his hot cum flooding into me.
Sobbing with each breath he thrust a few more times, emptying his load into my willing body, and spent, without withdrawing he lay down on top of me. He took a moment to get his breath, and rolled off me. We lay side by side. We cuddled. We slept.
“Are you sure about this idea, Doctor Hoffman?” I asked.
I must have sounded pretty sceptical. I wasn’t even that keen to see the Dr Hoffman, even if he was an eminent marriage councillor.
“I know it seems somewhat unorthodox, but my methods have helped to save many couples from boredom and eventual divorce,” he replied.
I looked over at Vicki. Her face did not give anything away. She turned to me and said “I don’t know, honey, it seems harmless enough to me. It might help us to, put some mystery back into our marriage.”
“You have it exactly right,” added the doctor in his vaguely European accent. “It’s all about reinvigorating your relationship.”
“Well, yes, but by pretending to be singles and pick each other up in some sleazy bar?,” I insisted.
“Remember when you first met? The thrill of the chase, the uncertainly, the final fulfilment? That is what you will be trying to recreate with this little game.”
It was true. After 10 years of marriage, everything seemed a bit routine, even sex. We just didn’t seem that interested anymore, and this led to other problems.
“Well, OK, I suppose we could give it a try.” I was thinking more of the money we had paid to this quack, rather than any real faith I had in this plan.
“When should we try, George?” asked Vicki. She certainly seemed more keen on this than I did.
“Umm, we could try on Friday. I don’t have any meetings at the end of this week.”
“Agreed, then. Come back and see me in 2 weeks,” concluded Dr Hoffman.
Friday seemed to come around all too quickly, and as fate would have it, I did have extra work to complete. When I finally arrived at the bar, it was past 7:30 and I was more than an hour late.
The bar was quite crowded and I couldn’t see Vicki. We had chosen a bar in a big, expensive hotel so that it would not be a sleazy pick-up joint. The bar was filled mainly with businessmen unwinding after a hard week’s work.
I finally spotted Vicki sitting at the bar and it stopped me dead in my tracks. She looked simply stunning.
Vicki was wearing a small black dress that rode up at least half way up her firm thighs. The front of the dress dipped daringly to show her ample cleavage. She was sitting crossed legged on the stool in such a way as to best show off her long legs and black stiletto high heels. There was more makeup than usual and bright red lipstick.
I started to feel a bit guilty because I was just in my usual work suit. She had obviously spent a lot of time an effort in preparing for this and it worked. She looked absolutely beautiful and I didn’t know why we were having problems with boredom. Why wouldn’t anyone want to have her?
Just as I was thinking that, I was proved right. Before I could get to the bar, to greet Vicki, another man approached her. I should have just cut in right there and then, but curiosity got the better of me, and I wondered how Vicki would handle this. I sat down at the bar a couple of seats behind Vicki and listened in.
“Such a pretty woman shouldn’t be alone in a bar,” he said as he sat on the stool beside her.
I almost laughed out loud at such a clichéd pick-up line, and Vicki made it clear that she also didn’t think much of his tactics by more or less ignoring him. But to his credit, he persisted.
“Yeah, I suppose such an old routine wouldn’t work for someone like you. But I was so amazed by your beauty that I just didn’t know what else to day.”
I could barely contain my amusement, but it seemed that Vicki was becoming flattered by the attention.
“Let me at least buy you a drink,” he offered. “Were you waiting for someone?”
“Well, I was sort of waiting for…” Vicki’s voice trailed off. “Ah, what the heck. Looks like he isn’t showing up. I’ll have a Seabreeze, thanks.”
I must admit that I was a bit surprised that she accepted his offer, but didn’t blame her given my lateness. Just give her a few more minutes, I thought. He ordered her drink and introduced himself as Greg. He was a bit taller than me and, being in his early 30′s, was about the same age as Vicki and myself. He had dark, neatly cropped hair and strong chiselled features. He wore a dark blue conservative suit that said ‘pure corporate style’.
In between constantly remarking about how attractive Greg thought she was, he mentioned that he as a merchant banker here to stitch up a big deal. He was staying in this plush hotel because, as he said, that was what the company account was for.
Just then, another group of people approached Greg and Vicki. Greg stood up to greet them.
“He guys, how did it go. Details all finished?” Greg asked?
“Yep, all done. Signed, sealed and delivered,” said one of the others.
“Good work people,” Greg said and they high-fived each other. Then he turned suddenly to Vicki. “Oh, how rude of me. Vicki, this is Roy and Penny, my colleagues from head office. And this is John from our local branch. Team, this is Vicki.”
They all shook hands politely with many pleased-to-meet-you’s and so on.
“You could always pick the good lookers, Greg,” Roy said to Greg slyly. “But you’ve really outdone yourself this time.”
Vicki blushed deeply, her face almost matching her lipstick.
“Don’t give Vicki the wrong impression of me,” protested Greg.
“No , I’m sure she’ll find out for herself soon enough. You see Vicki, Greg has somewhat of a reputation around the office,” John added.
“All rumor and hearsay,” replied Greg unconvincingly. “Anyway, why don’t we all grab a table so you don’t all have to stand up.”
The three latecomers led them off and Vicki followed them. I noticed that Greg stayed behind Vicki and was looking at her from behind as she made her was to the table. I could see why as her ass swayed provocatively as she walked on her high heels, her short dress revealing most of her long legs. After a short while, I discreetly moved to the table next to them.
The group spent the next 20 minutes or so congratulating themselves on closing the deal and they were obviously in the mood to have a much deserved break. Greg, though, continued to lavish attention on Vicki. Roy also seemed to be quite interested in Vicki, but I did notice that John and Penny seemed to have some sort of tension between them. I imagined that this was some inter-branch affair starting up.
They continued to order drinks and Vicki was keeping up with them. Eventually, she had to excused herself to go the ladies’ room. As she got up, she saw me. I thought quickly and I gave her a wink. After a slight pause (probably from the shock of realizing that I had seen what she was doing), she continued to the wash room.
Upon her return, she discreetly passed me a note written on a paper napkin as she walked by my table. It read “Remember, this is dating game where we are both single. If you want me, you need to win me!”
What a little tease! She had signalled her intention to play this game for all it was worth, and now she was really getting in the role. Whether it was playing a role or whether it was the alcohol, she started to respond more to the attention that Greg and Roy were giving her. She even let Greg put his arm around her.
I knew I could act at any time, but I didn’t. A little part of me wanted to know how far Vicki would go. But I knew that for some reason, I felt turned on by the thought of another man being very attracted to Vicki. As I pondered this, I realized that I was getting excited by the thought of Vicki being seduced by man. But surely this would not be a good thing? How could it help our love life?
My head was swimming with these conflicting thoughts when Greg made a suggestion. “Why don’t we all go up to my room.” They all agreed and got up to leave. Vicki turned to me and gave me a wicked little smile. I let them go on a little bit, then got up to follow them some distance behind. Greg walked with Vicki, and I noticed that this time it was Roy and John who were mesmerized by the Vicki’s body slinking across the hotel lobby. Penny looked a bit annoyed at John.
They got into an elevator. I tried to catch up to them, but I just missed it. Damn, I thought, what do I do now? I looked at the elevator indicators, and saw that the elevator had stopped at the sixth floor. I quickly grabbed the next elevator and punched the ’6′ button.
When I got out, I heard voices coming from the right. I hurried down the corridor to follow the voices, and caught sight of a door closing. Room 608. I pressed my ear to the door. It was the right room, as I could recognize Greg’s voice. I heard the sound of a champagne cork pop and some cheers. Obviously still celebrating the deal.
Fairly quickly, John and Penny started to make their excuses to leave (their intention pretty clear, even to me). As they said their goodbyes, I had to think fast. There was nowhere to hide. The doorknob started to turn.
Quickly I stepped to room 607. As John and Penny emerged from the room, I pretended to fumble for my keys trying to enter room 607. Then I had a horrible thought: what if either John or Penny were staying in room 607?
Fortunately, they walked right past me towards the elevator. They were too obsessed with each other to even notice me. I hurried back to the door of room 608.
I could now hear the sounds of Vicki, Greg and Roy murmuring and giggling. Roy said something about leaving the two of them alone.
“Don’t go, Roy, it’s fun having you here as well,” said Vicki.
“What do you mean by fun?” asked Roy.
“I don’t know. It’s just nice to be the center of attention of two handsome men like you,” replied Vicki.
Greg then started murmuring something, but I could not make it out. There was a short pause.
“Ohh, that sounds very naughty,” cooed Vicki. “I’ve never had two men at the same time before!”
I was dumbfounded. I should have knocked on the door there and then. But my mind was a mess at this point. Not only was my wife of 10 years contemplating cheating on me (with my knowledge!), but she was going to do it with two men at once! To my surprise, I found this made me even more horny than before and I had a raging hard-on. I was so excited, I feared that they could even hear my heart pounding in my head. However, I pressed my ear closer to the door to hear more clearly.
“Well Roy, how about you? Are you in?”
“Heck, I’ll try anything once!” replied Roy.
I could hear the sounds of shoes hitting the floor and zippers been undone. Then Roy said “I’ve been wanting to look at those wonderful tits all night.”
“Well, here they are” pronounced Vicki proudly. I could almost hear them flop out of the tight dress she was wearing. “Oh, yeah. Suck them like that, Roy. Mmmm”
I heard the sound of Vicki moaning softly. I couldn’t believe it. Two total strangers were about to gangbang my wife, and I was standing outside the door listening in. More than that, I was so turned on by it. I only wished I could see what was going on.
“Here, Vicki, let me help you out of that dress which Roy is occupied,” said Greg. I heard the sound on more clothes rustling. “What a beautiful ass you’ve got there Vicki. I don’t think you will be needing these panties anymore. I see that you are a natural blonde.”
“Hey, that’s not fair. I’m wearing nothing, and you two are still dressed.”
“That’s not entirely true,” said Greg. “You’ve still wearing your shoes.”
“You know what I mean, you bad boy! C’mon, take them off.”
After more sounds of clothes being taken off, Vicki said “Oh wow! It’s so big. Your cock is much bigger than my husb…um, last boyfriend.”
“You can see why Greg has such a big reputation around the office,” said Roy.
“Well, you’ve quite well endowed yourself, Roy,” said Vicki.
“Would you like to know what it fells like inside you?” asked Greg.
“Yes. Please, Greg, please,” pleaded Vicki. I couldn’t believe it! She sounded like she was really desperate to be treated like a slut.
“Then bend over this table so I can look at your pretty ass while I fuck you.”
It was a matter of seconds and I heard a loud “Ow! Ugh!”. Vicki groaned as she was apparently being entered from behind.
She sounded like she was in a bit of pain, but she was enjoying it. With each thrust, she said things like “Oh, you’re so big Greg! I’ve never had such a huge cock!” It was so unlike Vicki. She had never been much of a talker during sex, and this dirty talk was really out of character.
She surprised me even further when I heard her say “Roy, I want you in my mouth while Greg fucks me.”
Vicki stopped talking, obviously because she was sucking Roy’s cock while Greg was fucking her from behind. All I could now hear was a muffled “Hmmph!” accompanying each slap of Greg’s thighs on Vicki’s ass as he pounded her pussy hard. I tried to envisage the scene as my lovely wife was moaning on a stranger’s cock while being fucked by another strange man.
“I think she’s enjoying the ride, Greg.”
Greg didn’t answer, but Vicki managed to say “Mmmm hmmm!” in agreement with her mouth full of cock.
Steadily, the pace of the slapping increased, and Vicki suddenly cried out “Yes! Oh, yes! I’m coming Greg! Faster!”
Greg complied and Vicki let out an almighty yell. “Yeeeesss! Oohhhhh, yeeesss!” I thought everyone on this floor would hear her screaming. Vicki had never cum while I fucked her, so this was a very pleasurable new experience for her.
Greg continued to thrust quickly and Vicki was evidently having multiple orgasms as she was reduced to incoherent yelps of delight with each thrust. Slowly, above her voice I could her Greg grunting. His grunting became quite animalistic until, inevitably, it rose to a crescendo of his grunts, her squeals and squelching noises followed by a sudden silence. After a very short pause, Greg let out a groan like a huge release.
“Oh yeah!” yelled Vicki. “Pump your cum deep inside me! Ohh, it feels so hot!” Greg just continues to groan for what seemed like an eternity while Vicki moaned softly.
It was silent for a little while, until Roy broke it with, “Well I’m glad you had such a good time Greg, but you interrupted my nice little blow-job there. I’m just busting to fuck this hot babe.”
“Yes, Roy, please fuck me as well. I want you to fuck me too.”
“My, my, the little lady certainly is eager!” commented Greg. I heard a wet ‘plop!’ as his penis presumably exited Vicki.
“So am I,” Roy said impatiently. “Move over, Greg. Do you want me to fuck you now, Vicki?”
“Yes” said Vicki softly, like she was pleading. “Please fuck me.”
I heard some shuffling of feet, then “Ugh!” which indicated that she was entered again. But unlike before, this was followed by silence. I wondered what was happening.
“Hey, Roy, don’t tease me like that,” said an obviously annoyed Vicki.
“But you sound so cute just then. Can you beg me to fuck you some more.”
“Ooh, you like dirty talk huh? Well, fuck me!,” Vicki cried out. Roy must have obeyed, because this was quickly followed by another groan. “Yes, fuck me deeper!”
She repeated this many times until it was almost like a mantra. Then it changed. “Yes, use me! Do it to me! Fuck me hard!” With each utterance, she sounded more and more wanton.
“I’m all the way in now. Does it feel good?” asked Roy.
“Oh, yes!” Vicki said ecstatically. Roy started to fuck Vicki in earnest and she responded vocally.
“Well, seeing as you don’t need to talk anymore, I’ll put that lovely mouth of yours to better use,” said Greg, who had been quite for a while, no doubt recovering from his last orgasm.
Vicki’s yelps of open-mouthed pleasure quickly turned to muffled moans as Greg stuffed her mouth while Roy got busy from behind. Soon the familiar combination of moist squelching, flesh ramming into flesh and Vicki’s muted groans of delight filled the air. I was disturbed to find that it was so familiar so quickly, but more disturbed to note how turned on I was by it.
“Man, that’s a great blowjob you’re doing,” said Greg, haltingly. Vicki, it seemed, was too busy to respond. I just heard her slurping and moaning away.
“Yeah, I know.,” said Roy. “She pretty talented to be such a good cocksucker while she getting fucked.” With that, Roy seemed to fuck her harder, and her groaning became louder. This time though, she didn’t abandon the task in front of her, and she seemed determined to keep Greg’s cock in her mouth no matter how hard Roy rammed her.
After about 5 minutes of this, one of the guys said loudly “I’m going to come!” and with that he let out a prolonged groan. Vicki seemed to gag, but then composed herself and said, “Mmmm, Greg, that was delicious. I wish I tasted some of Roy’s cum too.”
“How did you do that? I’ve never cum twice so quickly,” marvelled Greg.
Vicki didn’t answer him because Roy had picked up his pace again and all I could hear from her were squeals with each slap of flesh on flesh. There were incoherent mutterings from Vicki as she neared another orgasm, which came more suddenly than her last. Another loud scream filled the air that I was sure would have the other hotel guests wondering what was happening.
Roy climaxed soon after Vicki did but without as much drama as Greg. All I could hear was a slowing, then stopping of the squelching thrusts and Vicki moaning softly, “Yes, fill me Roy. Fill me up with your cum.”
Then all was quiet. I could hear them speaking softly, but could not make out the words. I heard Greg offer some more drinks and someone use the bathroom. I heard people starting to get dressed.
The first thing I could make out was “That was wonderful boys. I had a really great time,” Vicki saying in a soft, languid voice.
“You are one hot woman, Vicki. Are you sure you’ve never done it with 2 guys before?” asked Roy, almost in awe.
“Well, we don’t leave for head office until Sunday. You can always drop by again tomorrow,” suggested Greg.
“Sounds tempting, but I’ve got other plans.,” she replied. I was disappointed that I would not witness an encore performance, even if it was from the other side of a door. “Would you like to keep this as a souvenir?”
“Hell, yes,” they both replied.
As they were kissing goodbye, I quickly made my way to the elevators. I heard their door open and then shut. I eventually spotted Vicki as she walked slowly around the corner, almost in a dazed state.
She was quite a sight. Even though she had made some attempt to clean herself up, her make-up was a mess with her lipstick smeared around her mouth and her mascara running. Her long, blond hair was tousled and here and there were some bright, wet patches, possible semen in her hair. She teetered on her stilettos as she walked along, undoubtedly due to the thorough workout she had just endured. To say she had the ‘just-fucked’ look would not be doing her justice; more like ‘just-fucked-by-a-large-group-of-hormonal-frat-boys-look’ was more like it. In her dreamy state, it took a while before noticed I was there. It took even longer before she realized who I was. She stopped dead in her tracks as if she had seen a ghost.
“What did you see?” she managed quietly.
“I didn’t see anything, honey. But I think I heard everything while standing outside the door.” She became even more pale, and then blushed deeply.
“Oh, George!,” she blurted out. “I’m so ashamed! This was meant to be some innocent game, but I ended up fucking two total strangers. I don’t know what came over me. I felt so naked standing there in just my high heels and those two staring at me. I just lost all control of myself!” She started crying.
I went over to hug her. “There, there. It’s alright. I still love you,” which was an understatement as I was so turned on at this moment.
I patted her on her back. As I did so, one of my hands unconsciously slid down her body and up her skirt. She flinched back as my hand glided up her still moist thighs. When I got to her crotch, I touched her bare, moist skin and I realized she was not wearing her panties. This was obviously the souvenir that she had given to Greg and Roy.
Their relationship so far had been passionate, fun, and sexy, but Maria knew that much of that had been driven by Alan’s fantasies, with which she gladly participated. Recently, Maria had decided that she wanted to take a more active role in shaping their love life, and had found her inspiration in a most… unusual place. A few weeks back, in a humorous but surprisingly sexy attempt to get her comfortable with switching from her previous, female, doctor to a male one that was covered by her HMO, Alan had dressed himself up for a fantasy where he “examined” her with a latex glove in all her intimate places. Something about the feel of that latex glove sliding around and in her body had sparked something hot inside her, something different. After a quick consult with one of her kinkier friends, she had dreamed up a scenario sure to spice things up and assert her own sexual flavor to their lovemaking.
While shopping online for the perfect outfit, she came across a set of pink latex opera gloves and thigh high stockings; a pink almost alive in it’s electric vibrancy, one which brought all sorts of naughty thoughts to mind regarding things sweet and virginal with a dirty twist. Given that her petite 5’3″ frame, heart shaped face, big eyes, full, pouted lips, and high, cute voice had made her seem years younger even late into her twenties, she felt that it matched nicely and was sure to show Alan that despite her looks, she was an experienced lover with dark passions. To compliment the gloves and stockings she chose an outfit she was sure he’d never expect: a pink latex corset top with optional, inflatable breasts and an indecently high matching mini-skirt complete with petticoat ruffles. Topped (or bottomed, she giggled) with a barely-there pink thong she was *sure* she’d shock her beaux and gain some respect for her own fantasy ingenuity.
She’d chosen a night to wear it when she knew he’d be home late, and when he called one Friday to cancel their dinner date because his boss had requested that his whole team stay late to finish out a deal, she knew her time had come. Telling him not to worry, that she’d cook up something nice at her place and that he should come over whenever he was done, she left work early and headed to pick up some special lubricant that her kinky friend had suggested she use to ease her donning. At the drug store, she grabbed the big bottle of water-based lube and ran to the checkout line to have as much time as possible to get ready. Waiting in line she saw all the Christmas decorations out and right there, on the counter next to the register was a display of those old-fashioned, huge peppermint sticks. Like a miniature barber pole, almost a foot long and easily an inch wide, she smiled evilly as she realized how to complete her image tonight. The clerk eyed her oddly as she paid for her lube and the trio of large confections, but she was beyond caring, already thinking ahead to her perfect fantasy.
At home, with everything ready for a late (very late, if she had anything to say about it) dinner, she took a shower, and took an hour to put her long, silky black hair up into ringlets. She applied a thick cover of blush, bright red smudge-proof lipstick, and enough mascara to make her eyes seem overlarge in her now almost cherubic face. Maria laid out all her garments on the bed with the lube and recalled her friend’s instructions. Suddenly a little nervous, and slightly aroused by the thought of what she was about to put on, she pushed through the butterflies bouncing around in her tummy and poured a generous amount of lube into one hand. Liberally, she applied it all up and down her other arm until it was slick to the touch. Drying her hand on a nearby towel she’d laid out to clean up the excess lube she grabbed the first glove and slowly slid it up her arm.
The sensation of the wet latex slipping up and across her arm was delicious, and her eyes half-lidded in appreciation, but it was when her fingers finally slipped in the hand of the glove that she felt this incredible, warm, wet, grasping sensation all the way up her arm starting with the tips of her fingers working it’s way through her palm and across the back of her hand. She marveled at this sweet, wet, tightness and the way the dusky pink looked on her lightly tanned skin. There seemed to be little pulses of electricity flowing out her arm and down her body straight between her legs and she felt her body clench sensually. All this from one glove, she thought?
As Maria began pouring lube into her now gloved hand in order to similarly moisten her other arm she noticed a curious glistening in her hand which she made a mental note of as the lube slid across the fabric. Rubbing down her ungloved hand and arm with lube was an experience as well as she felt as sense of intimacy mixed with detachment from touching herself, as though she were inside someone else’s body while still feeling it touching her own. With a little shaking and considerable anticipation she eased the other glove up her now-slicked arm. Once again that wonderful slippery sensation caressed her arm followed by that same soft/tight wet heat grasping her arm as though it were her most intimate of intimates.
Somewhat overwhelmed by the feelings this latex was sending through her, Maria decided to sit to apply her stockings rather than stand, as she’d originally intended. Grabbing the bottle of lube with a gloved hand reminded her of how shiny her hand had become once covered in wetness. Teasingly, she poured the lube directly on her latex-clad arm and shivered as she felt the stream fall on, yet not on, her skin. Rubbing in the lube produced a deep shine on the latex that she found herself marveling at, reminding her of other pink, wet places, and causing her to realize just how aroused this whole process was making her.
She then rubbed more of the contents of the bottle all over her legs, wanting both to feel those sensations here, but also knowing that if she allowed herself time to pause after one leg was finished, she might never make it to the other. She intended to don her stockings in quick succession, but she was unprepared for just how much the feel of wrapping her first leg in latex would get to her. Immediately, she noticed the wetness between her thighs grow as the liquid heat seemed to push up from her foot all the way up to edge of her nether lips and underside of her ass. With ragged breaths she tried to forge ahead and slide on the other stocking, but halfway through she couldn’t control her arms as her eyes slid shut and she simply sat there and *felt* how wrapped and warm and slick she was and with an effort of will tugged the final stocking into place. Grabbing the bottle of lube, she headed to the bathroom to check herself out in the wall to wall mirror above the double sink.
She was totally unprepared for the image that confronted her, however, the slim, waifish woman replaced by a shiny, wet, sexual being, clad brazenly in nothing but long gloves and stockings, declaring her femininity to the world by leaving her most sensitive parts free. Maria quickly applied the lube to her stockings to complete the shine, and was struck by how *different* she looked. The latex slimmed but also defined her arms and legs, eliminating details, but accenting curves in the most erotic way possible. As she spun in front of the mirror, she also noticed that the high stockings were pushing her already perky ass up in a delightfully slutty way.
As she watched this woman who could not possibly be her, place those slick/shiny wet hands on various parts of her body to assess her look, she became incredibly aroused. She no longer felt like Maria, but *possessed* somehow, enchanted by this material, this feeling, this *woman* in the mirror staring back at her. The evil grin she sported in the drug store crept back upon her face and she watched this woman pour lube directly onto her body in thick, watery streams that cascaded down her body only to be caught by a glove and rubbed all over her aching skin. Caressing her breasts was giving her fits, but when she moved on to rub the lube into her ass her hands clenched her cheeks reflexively as a fresh wave of sexual heat enveloped her body. She felt like she was breathing fire, she was so hot and the need burning inside her threatened to consume her if she touched herself any more.
Through clenched teeth she uttered a desperate moan and moved her hands away from her body to pick up the corset top and start sliding it over her frame. The awkwardness of this action seemed to quell her inner fires for a moment until the bulk of the garment slid past the wideness of her shoulders and cleavage and slipped into place like it had been made specifically for her. The feel of her breasts sliding into the inflatable cups and the thick, warm latex grasping her belly like a lover was enough to send her to her knees on the thick faux-fur rug in front of the sink. It was some moments before she had mastered her breathing and the sensations running amok through her body enough to stand and walk back over to the bed. The petticoat mini skirt was a gorgeous touch, but donning it did little to stoke her flames. The tiny latex thong that covered almost nothing, however, she knew was going to be a problem. Deciding to leave it until later, she simply lubed up the fabric and set it aside.
The final step, as it were, was to don a pair of matching, pink PVC fuck-me pumps she’d bought to complete the outfit. 3.5″ heels thrust her ass out like an advertisement, and added a welcome tightness to her calves and feet. Prepping herself in front of the mirror she realized she’d yet to lube her top and skirt, and see what inflating her breasts looked like. With no little trepidation she began rubbing her top with lube and felt the flames explode beneath her skin, not at all cooled by the watery slickness she shined into her tummy, breasts, and skirt. Instinct and desperation taking over, the woman in the mirrors hands became a frenzied blur, rubbing themselves faster and faster over her body, grasping, grabbing, gasping, and moaning in nigh-orgasmic frustration. Dammit, she’d wanted to wait for Alan, but this woman, this other her wasn’t going to wait.
Giving herself over to her darker side in a long moan of release, one hand continued its frenetic stroking and groping of her chest and tummy while the other dove for her cleft, cupping her heat and driving it back inside of her. Her eyes lidded and her breath panted as she felt her gloved fingers penetrate her nether lips and find that glorious nub of pleasure. It only took a moment for her body to come in quick, crashing waves, but as her shaking frame rested against the countertop, she realized that she’d only just stoked the flames as she felt her darkness beg for something to fill her burning void. Inside, she was nearly screaming with frustration as small mewlings came from between the red, shiny lips of the woman in the mirror, as she cast about desperately for anything to plunge inside her depths and abate the ache in her loins.
Unfortunately, Alan kept all of their sex toys at his place, and Maria had only ever used a hand vibrator, never having wanted a penis without a man attached before. But this other woman *needed* something, and her eyes lighted on a prop she hadn’t planned to use until much later. Oh, NO, she thought embarrassedly, but this other woman had her legs already in motion, clicking heels striding desperately across the floor towards one of the peppermint sticks she recently purchased. Unwrapping it clumsily, her gloved, wet hands peeling back the wrapper with difficulty, she released her impromptu dildo from its wrappings and with no time for second thoughts, slid it authoritatively into her molten cleft.
Almost instantly, she locked her muscles around it, unable to stifle a load moan of relief as she felt some small measure of sanity return as the need abated. Still, this other woman worked the stick in and out of her with a vengeance, darkly elating in the debauched usage of the treat, which Maria could no longer deny was exactly what she wanted at the moment. As her body neared a second stronger orgasm, she felt her sense of propriety being overwhelmed by the joy and pleasure emanating throughout her body. As one, she and the woman in the mirror came again in a triumphant shout, and a languid warmth slid over her perceptions, coloring her world pink at the edges and driving her burning hunger deeper into her body, her lust slaked only momentarily.
With a lustful grin, she slid the red and white pole out of her moistness with a sticky pop and examining it for a moment gave it a thoughtful lick. Lips wrapped around it, tasting the sweet mixture of sugar and her juices, she realized that this freedom, this perspective was more than just Maria, that it needed a name, to suit its darker, sensual personality. Mind churning, and keeping the confection with her, she quickly slid into her thong, reveling in the slick warmth it reflected back into her and the way it slipped enticingly between her ass cheeks and nether lips when she walked.
Deciding to treat Alan to the full show, she grabbed the pump for her inflatable breasts and slipped the needle into the valve on each side, increasing her bust size from a modest B to something closer to a D. Grabbing the lube, she perched on the edge of the bed, still working the pole through her lips in wanton anticipation, waiting for Alan’s arrival. She didn’t have to wait long, hearing his keys in her lock only minutes later. She heard him call out and set down his work things and coat before coming to investigate the bedroom. Legs crossed, foot kicking, she sucked slowly up and down the treat as he walked in the bedroom door and froze. As his eyes tracked lustfully across her form, her gaze locked onto his and she popped the stick out of her mouth, her lips forming a perfect ‘O’ for a moment before she smiled that evil grin and purred, “Hi, I’m Candi! Wanna fuck?”
Alan stared at her, shaking, for a moment, torn between disbelief and arousal. His eyes took in every detail of her outfit, and she preened under his scrutiny. As he moved in to kiss her hungrily, she stopped him with a latex-clad finger to his lips. “Not there,” she said throatily, pushing her hips forward to open her legs wide for him. Her finger moved to her bottom lip, where she licked it briefly, then traced a slow line down her body to the spread lips of her pussy, touching lightly on her button, which made her head roll back in pleasure. Her eyes closed from the sensation, and she half moaned, “*here*. I want you to taste your Candy.”
He dropped to his knees and breathed in her scent, moving forward lightly to run his tongue over her outer lips, causing her to quiver and gasp with pleasure. As he drank in her taste, he noticed… something else besides her normal salty sweet taste down there. Taking a deeper lick he tried to figure out what it could be; it was sugary with a hint of something cool, almost like… His eyes snapped up to hers as he stopped for a moment, and saw her finishing a moan with a pout as he pulled away, her voice muffled by the thick peppermint stick she was fellating. She noticed his look and gave that wicked grin, popping the stick out again to murmur, “Don’t I taste *good*, honey?”
At this evidence of her debauchery and deep eroticism, Alan found himself over taken by lust and shuddered, almost tearing his shirt and pants in an effort to disrobe as quickly as possible. “Candy” watched him with naked interest, eyeing his form appreciatively with a wicked look in her eyes and, as his pants finally came off, a lascivious grin around the cane in her mouth and a small noise of appreciation and anticipation as his member came free from confines of his underwear. Her free hand had been stroking herself lightly throughout his impromptu show and now reached out to grasp him around his full, erect length sensuously. Alan couldn’t help but sigh as she slowly wrapped her oiled glove around his cock and pumped him slowly off, seemingly reveling in the feel of his rock-hard flesh underneath her hand.
When his eyes opened again, he noticed that she was staring at him hungrily, and he could see that she was torn between continuing her slow handjob and taking him into her mouth. He could see her lips glistening from running her tongue over them as though the simple thought of having his cock between her lips was making her mouth water. His loins clenched tightly at the thought and her hand tightened around his member in response as her body echoed his sentiments. In seeming compromise, she came to a decision then, and, eyeing the contents of each hand, she locked eyes with him and slowly brought the sugared cane to her lips. Her other hand paused in its ministrations with her fingers encircled around the head of his penis, and as the candy touched her lips, she achingly sucked it inside her mouth. As the tips passed her lips, she fisted him in time with the stick in her mouth, as though her warm, wet, gloved hand were some surrogate orifice she could manipulate using her lips.
The duality of her pumping hands drove him near the edge quickly, and his soft, breathless pants came faster as he watched his goddess in pink fellate the confection while handling his cock. Her eyes were closed in rapture and her hips bucked forward with each thrust in anticipation. Finally, she seemed to pick up on the proximity of his orgasm and she slowed down to an achingly slow pace and removed the stick from her mouth. As he watched, on the edge of release, she slowly eased the confection into herself, as he’d tasted before, and renewed pumping them both off, slowly in time with each other. This time her eyes stayed open, flicking between his half-lidded gaze and his almost painfully erect member. She would speed up and slow down at random, sometimes pumping deep, other times just slipping the tip in and out of her hand and pussy. On particularly hard thrusts she would gaze at his cock hungrily, as though imagining how good it would feel inside her, in place of her impromptu dildo. His orgasm had never faded, but he found the pressure mounting under the firm grasp of her wet fist with no release. He had never been so hard in his life.
It was quickly building to the point of blurring the line between pleasure and pain, and it seemed that Candy sensed this, as after a sequence of particularly deep thrusts had left them both panting and groaning, she started fondling his glans, bringing him almost to the edge. Lips trembling, she fisted him one last time, down to his balls and took the head of his cock in his mouth while slamming the stick home deep into her pussy as her muscles locked around it. He came harder than he’d ever done, like a molten rush streaming out of him through their joined flesh. Only the fact that his knees half-locked kept him standing through the whole thing. He saw that her eyes had gone wild, and that her whole body was shaking, and as his come spurted into her gorgeous mouth, he could see her throat working to take it all down, as an almost soundless scream of ecstasy was coming from her lips, muffled by his cock. Wetness was dripping down the fist not wrapped around him as she oragasmed almost continuously for the better part of a minute. By the end of it she was red from exertion, panting for breath, and the come that she couldn’t swallow before needing to breathe was pooled in the bottom of her open mouth and ran in trickles down the sides of her face from the corners of her shining lips.
He found the sight so intensely erotic that his aching penis never had the chance to become fully flaccid before a new surge of desire brought him back to readiness as he watched. As she gathered herself, she saw his hardening cock and laughed, a sexy, lustful sound half on the edge of exhaustion, as she pried her sticky fingers from around the candy still gripped between her nether lips and said in a sultry tone, “Go ahead and taste, love. I got it ready for you”. He slowly reached down and gripped the stick lightly where her glove had been, feeling the sticky warmth she’d left behind. Shivering slightly in desire, he eased it out of her while she hissed in either pain or appreciation, he couldn’t tell. At her expectant gaze, he raised it to his lips and gave it an experimental suck. The taste of her was all over it, and there was a sharper tang to it, like some unexpected part of her essence from where his tongue would never be able to reach unaided. He found it thrilled him to taste her and made him hungry for more.