Life was so carefree until that day, when, on the morning of my eighteenth birthday, my father had thrown the apron of a serving wench at me and told me to get to work.
So I was to be a drudge then, in one moment all of my dreams and aspirations were shattered. I probably should have expected it, after all he wasn’t my real father and I’m sure he just saw me as an extra pair of hands.
I had been taken in as a baby, left on a barren couple’s doorstep one stormy night, or so the story went. My new mother had cared for me, I had no doubt of that but since she had gone my father’s attitude towards me had become positively hostile.
I tried not to think about who my real parents were, there was no solace in that. The only person who had ever cared about me was gone from my life forever and how I missed her.
My adoptive family had owned an inn on the highway for generations and many a traveller had passed through its doors, slept in its beds and drunk its ale. The Countess, as it was known, was also very popular with the local workers, farmhands and such, and was always a raucous place in the evenings.
Late that afternoon I was sent out to the stables to make sure that the traveller’s horses had been fed and watered properly. My father had never trusted Uncle Ham, our slovenly stable hand, and on more than one occasion he had found his mistrust to be well founded when Ham had been discovered passed out drunk in the middle of the day or indeed missing altogether for several days on end.
This morning though he was in good spirits. I immediately suspected him of drunkenness but was surprised when I could see no evidence of it.
“Afternoon Sarah,” Uncle Ham leered at me, his eyes as usual were fixed on the plump flesh of my breasts which bulged and threatened to spill over the top of my low cut bodice.
“Good morning Uncle,” I blushed as I spoke. His attentions were unseemly and wrong but still I felt a strange warmth spreading through my body and a fluttering in my belly when he looked at me like that.
“Give your old Uncle a kiss Sarah,” he reached out for me. His voice, oily and deep, sent a delightful tingle down my spine as my blush deepened.
As he moved towards me I hesitantly gave him a peck on his rough cheek, the stale smell of old ale making my nose wrinkle.
“Come now, we can do better than that,” he laughed as he grabbed my arm and pulled me towards him.
His harsh lips found mine and, as I gasped at his rough handling of me, I felt his tongue worm its way into my mouth. I sought to push him away but he was too strong for me, and then I felt his hands on me and my body betrayed me. He was my Uncle and so old, it was all so wrong! But I melted into his arms as I felt his hands roughly kneading my breasts and bottom.
“Started without me Ham?” I jumped as I heard my father’s voice behind me and fought to extricate myself from my Uncle’s arms.
I managed to turn my head away from him as he continued to slobber over my face and neck, his rough hand now working its way underneath my bodice and deep within my warm cleavage, his other still clutching my bottom and supporting my weight as I tipped backwards.
My eyes widened when I saw my father removing his breaches and then I gasped as he pulled his long shirt over his head and I saw, for the very first time in my life, a man’s cock. I had heard about them of course, the older village girls delighted in describing their soft warm hardness and delicious smells and tastes. But this was the first I had actually seen, it was far bigger than I had imagined and it was my fathers!
“Get her down and hold her, I’ll go first,” my father growled as he moved towards me, his stiff, angry looking cock bobbing and weaving above his heavy hairy balls.
I was hypnotised by it and put up only a slight resistance, whimpering quietly, as my Uncle Ham pushed me down into the hay on the stable floor.
I soon found myself on my back with Uncle Ham kneeling and holding my arms above my head, his bulging crotch only inches from my face. He moved his knees over my arms to pin them in order to free his hands and started to unpick the knot in the frayed rope that tied his breaches around his large gut.
I gasped as I felt my skirts being lifted and looked down between my legs. My father was kneeling naked before me, feasting his eyes on my under things and licking his lips as he caressed my naked thighs.
“F…father why?” I gasped as he leant forward and tugged my drawers down.
“Cos I promised your mother I’d wait ’til your eighteenth birthday,” he sniggered as he crawled forward between my legs a look of unbridled lust twisting his features.
I felt something warm and fleshy against my face and looked up to see Uncle Ham’s large hairy balls and rapidly swelling cock hanging over me. His fetid breath hissed between his teeth now and his eyes were wide and bright as he watched my father climb on top of me his hand guiding his stiff cock towards my virgin cunt.
“Oh no, no!” I moaned as I felt my father’s cock pushing and probing and then suddenly sinking hard and deep inside me.
There was a sharp pain which lingered for a short while, but nothing like the agony I had been led to believe I would feel.
“Yesssss, fuck her!” Uncle Ham hissed, grinning like a madman.
I looked up at him and saw that his cock was now fully hard, his heavy, sweaty balls now resting on my forehead. He stroked himself slowly and carefully as he excitedly watched his brother-in-law plough me.
My body twitched and convulsed, seemingly out of control, thrusting my crotch towards my father as he thrust harder into me. It was so wrong…but it felt delicious. It was deliciously wrong and I gave in to the pleasure that was spreading like wildfire through my young body.
“Fucking whore she loves it,” my father panted as he pounded away between my splayed thighs.
“Just like her mother,” Uncle Ham cackled.
I felt the pressure of Ham’s knees relax and lift from my wrists as he moved around me. Reaching forward he tore open the bodice of my dress, my large fleshy breasts bouncing and quivering as he released them. Grunting in delight, he lowered his slavering mouth to my chest and began roughly sucking and chewing at my nipples. Crying out at the wonderful new sensations now coursing through my body, I clasped his head in my hands tangling my fingers in his matted grey hair.
“Fuck…fuck…fu…” my father panted as his thrusts quickened. Then he cried out, his taught muscles standing out from his hairy body as he ground his cock hard into me. I felt it twitch and leap and a delightful warmth spread within me. Instinctively I wrapped my legs tight around his back pulling him in deeper, moaning and revelling in the hardness I could feel deep inside me.
All too soon he pulled out leaving me feeling empty and forlorn. “Go on Ham, your turn,” he laughed as he stood, collecting his clothes.
I still held Uncle Ham’s old grey head in my hands and he made no effort to remove it from between my heaving breasts as he moved his body around until it lay between my open thighs. He grunted and snorted like a pig as he slobbered over my chest, poking around ineffectually with his stiff cock. I reached a hand down between our bodies and helped him in and all at once he began to fuck me hard and fast like a wild animal.
The feelings coursing through my body were incredible. I felt full once more and never wanted to feel empty again. Wrapping my legs tightly around the old man’s back I held onto him for dear life as his pounding increased in its intensity. Then my body tensed and I felt an explosion in my belly as I came like I never had before. I panted and moaned like a cheap whore, my soaking cunt making lewd squelching noises as the old man took me on the stable floor and I begged him to go faster and deeper and harder.
This sent Ham over the edge. He lifted his head from my chest and cried out, spittle dripping from his open mouth as he slammed into me a few final times, his body twitching as he filled me with his hot seed. There seemed no end to it and my hips bucked and thrust into him as he continued to empty his hairy old balls into my cunt, until finally he subsided collapsing down on top of me.
I stroked his grey hair as I felt his softening cock slip out of my cunt and smiled to myself, perhaps my eighteenth birthday wasn’t going to be so bad after all?
My reverie was interrupted by my father’s harsh laugh, “Get yourself cleaned up and get back inside girl, there’s thirsty men need serving.”
Uncle Ham groaned and rolled off me and into the hay, so I sat up and reached for my drawers.
“Oh and don’t bother with your knickers, they’ll just get in the way,” my father laughed again and walked out of the stable tucking his shirt into his breaches.
I considered my crumpled knickers for a moment then instead of pulling them back on I wiped between my legs with them, cleaning up the mixed juices that were dripping out of my hole and dropped them next to Ham.
It took a good five minutes to remove the hay from my dress and hair, wincing as I worked my fingers through the tangles in my long blonde tresses. While my torn bodice was almost beyond repair, I managed to mend some of the damage but still my breasts were barely concealed. I looked a mess, it was obvious for anyone to see what I’d been doing and now I was going into the parlour of the inn to serve drink to lecherous louts. I smiled to myself feeling incredibly naughty and virtually ran to get inside.
The parlour was dark and smoky and after being outside in the bright fresh sunshine, I coughed and my eyes struggled to adjust to the gloom.
All of a sudden I was grabbed by unseen hands and pulled into the lap of someone who smelled like a brewery. A loud cheer went up as my bodice was torn open once more and my tits spilled out for everyone to see. I felt a hand thrust up my skirts and gasped as my pubic hair was grasped and yanked and then a finger roughly inserted into me.
“Come on there’s men need serving,” I heard my father shout.
My eyes were growing accustomed to the gloom now and I could see him standing behind the bar laughing at my discomfort. There were several flagons of ale on a tray in front of him waiting for me to serve them, so I struggled to stand, pushing away the hands that groped at me and felt momentarily sad as the finger slipped out of my wet cunt.
I made my way to the bar, hands pinching and slapping my bottom and groping at my bare breasts. The parlour was packed full of sweating, leering men of all ages. I couldn’t count them all but guessed that there must be at least thirty in the room all shouting obscenities at me and lusting after my body.
When finally I reached my father he just sneered at me, “Don’t fucking spill any,” then turned his back and began filling more flagons of ale from the giant barrels stacked behind the bar. I gripped the sides of the tray and lifted it, being as careful as I could while being groped and pawed at from all angles.
I made my way around the room handing out the full flagons and collecting the empty ones from the tables. There were hands beneath my skirt wherever I went, fighting to insert their fingers inside me.
As I set down the last flagon a thick finger was thrust hard inside me and I gasped as it was twisted and turned roughly between my soaking lips. Another hand, feeling the first one blocking its path instead moved around behind and my stomach flipped as I felt a probing finger between my plump buttocks.
I dropped the tray of empties and another loud cheer went up.
The owner of the hand came up behind me laughing, wrapping his arms around me and pushing his tongue into my ear. He roughly groped my tits with one hand whilst the other he brought back out from beneath my skirts just long enough to wet it in his mouth before shoving it back up and under and I gasped as I felt his thick, wet, meaty finger pushing firmly at my tight anus.
There was a moment of sharp pain before I felt a slight pop and his finger was inside me, it felt strange and dirty, and although it did hurt I loved it from that very moment. I worked my bottom back onto his finger, rotating my hips and forcing it deeper inside me, inch by delicious inch. The man continued to lick and suck at my ear and down the side of my neck as he worked his digit in my tight hole, then suddenly tiring of his little game he pulled it out and pushed me face down over the beer stained table in front of me.
I cried out as my head struck the rough wooden surface, then began to pant as I felt my skirts lifted and thrown over my back. There was another loud cheer as the men in the room gathered round me and I smiled as once more I felt a hard cock probing between my legs.
This time however it only briefly probed my cunt before, coated in my juices, it was pushed hard against the tight sheath of my anus. I pushed back onto it wantonly, desperate to feel it fleshy thickness ploughing my insides, grinding my hips in small circles as the tip pushed inside.
This time it hurt a lot more and I squealed, pulling away slightly as I felt the pain, but I was roughly pushed against the table top once more and I felt the man enter me with one long hard thrust.
I was in agony and beat the table with my fists as I felt his thick cock sawing at my backside, but slowly the pain subsided and was replaced with a stinging throb. All the while I felt the heat building inside me and the beating of my fists soon slowed to a halt. Instead I gripped onto the edge of the table, panting more heavily and bracing myself as the strokes lengthened and quickened.
Soon my unknown lover was buggering me hard while the crowd cheered him on, the table creaked and squeaked as we fucked, its legs threatening to give way. But I didn’t care, I was in heaven. I was the inn whore, ready to be taken by man after man, ready to give pleasure to hard cocks whenever they wanted it.
Suddenly he pulled my head back hard by my hair as I felt his cock twitch inside me and thrust hard one last time as he spunked deep in my bowels. For a few more moments he was deliciously deep inside my arse and then all too soon he was gone, leaving me empty once more.
I laughed loudly as I felt another man behind me, another hard cock pushing at my gaping anus and pushed back onto him in abandon, crying out in joy as he slammed into me up to the hilt and proceeded to bugger me roughly.
More cheers erupted as I was taken again, the table now on the verge of collapse as it wobbled and creaked beneath my lover’s thrusts, but suddenly they stopped as did he. I moaned in frustration as the beautiful thick cock was withdrawn quickly from my anus and looked round to see what was going on.
The crowd had turned and were staring at a burly, caped figure all in black standing just inside the inn door.
“Venom,” I heard several men mutter.
“God help us!” another one moaned.
The figure scanned the room quickly, his face obscured by the shadow of a large tricorn hat which sat tilted forward on a white powdered wig. I felt his eyes pierce me then he moved quickly to my side. As he did so the other men in the room shrank back, sidling towards the door and out. Soon I was alone in the inn parlour with the dark and mysterious stranger, even my father had disappeared.
“Come with me,” the man spoke quietly and in a commanding tone as he grabbed my arm and pulled me towards the door.
My skirts fell back down, but my naked breasts bounced and wobbled lewdly as I was half dragged outside. The sudden sunlight blinded me for a moment and I only briefly saw a great black carriage and four before being thrust roughly into its black interior. Its door slammed shut behind me.
I fell back onto a wooden seat, once more blinded and waiting for my eyes to adjust. Suddenly the carriage lurched drunkenly and I fell forward as I heard the horses whipped up and we began to move.
I picked myself up and seated myself once more, my eyes now growing accustomed the gloom of the carriage and my heart hammering in my chest. Had my dream come true after all? I squinted as the large shadowy figure sat opposite me became more visible; he didn’t look much like a dashing prince.
“Hello my dear,” it was a woman’s voice, a woman’s deep melodious voice, both sweet and dark.
I shivered and crossed myself, I felt as if the dead were dancing on my grave.
Then I saw her eyes, those beautiful hypnotic eyes.
I sat entranced as she slowly opened her cape. She was naked beneath it, fat, huge. Her fleshy belly and sagging breasts were enormous. Her flabby body bounced and wobbled with the carriage’s movement and I gasped as I saw what looked like a giant black penis hanging down between her fat milky thighs.
She hissed, her serene face suddenly becoming twisted and furious and then she was on me. Clawing at my clothes, tearing them off like a wild animal she pressed me back across the wooden seat. Hearing another, lighter hiss I looked down in amazement and saw that her huge black penis had come alive. What looked now like a huge black serpent was hissing and slithering, its tongue flicking in and out of its mouth between rows of tiny sharp teeth.
I gasped as it dived suddenly between my thighs nipping at my soft flesh. I cried out, terrified but powerless to resist as I looked once more into the woman’s eyes. She was grinning evilly at me, running her long tongue around her thick, deep red lips and pinching her engorged nipples with her free hand.
I wailed as I felt the serpent enter me, its thickness stretching my cunt walls to the limit.
“Submit!” the woman hissed. “Submit!”
I felt small sharp teeth nibbling inside me as the serpent moved deeper still, then the pain reached a sudden crescendo and I surrendered completely to her.
“Take me!” I gasped feeling an incredible ecstasy at the pain I was enduring.
With that she fell on top of me, crushing me with her fat, fleshy body, her mouth opening wide to reveal long, viciously sharp, white teeth. I turned my head to one side and openly offered my neck to her and she laughed sinking her teeth into my flesh as I abandoned myself to her, wrapping my arms and legs around her tightly.
I felt a burning fire in my veins as an incredible orgasm wracked my body and I cried out in joy as I felt her thrusting between my legs, the huge black serpent pistoning in and out of my overstretched cunt.
“Yes…yes!” I moaned more and more weakly as she took me. The carriage had stopped now, but it rocked furiously as she pounded me harder and harder, whilst sucking the life blood from my body.
When I was close to spent, she lifted her head from my neck and gloated over me, my blood dripping from her fangs and onto my breasts. Then I felt a gush of hot liquid and a sharp pain inside me, the demon cock had cum.
“There my child,” she whispered as she stroked my hair, “the Venom is inside you now.”
I felt as if I was outside of myself looking down at the hugely obese woman lying on top of my body and licking at the open wound on the side of my neck. Then the scene began to fade, as if I was floating backwards down a dark tunnel, faster and faster I moved until all was blackness and I knew no more.
To be continued…
The door slams downstairs but I’m too turned on to stop fingering myself. Too hot to worry about anybody coming in. Besides, nobody will bother me. If my door is shut, they leave me alone.
I look at the screen again and watch the pretty blonde get gang banged. ‘I wish that would happen to me.’ I think to myself. A skinny dick slides in and out of the blondes mouth, a hand pulls at her hair while someone else’s hand kneads her breasts. The camera zooms in on the dick in her shaved pussy. I watch the dick slide in and out of her, spreading her lips with each withdrawal. She shifts slightly to accommodate the cock in her ass and she groans around the dick in her mouth.
At just 19 years old, I doubt this kind of thing will happen soon.
I rub my clit harder and bite my lip hard. I’m so turned on. I spread my legs wider and push my fingers deeper inside of me. I pinch my nipple and groan as I hit the right spot with my fingers.
“Ohhh.” I moan out loud.
“Well well well …”
“What have we got going on here?”"
“Uncle Tom! What are you doing in here?” I screech, jumping off the bed and grabbing some clothes.
“Don’t stop on my account princess…” He smiles at me.
I frown at him and turn around, rushing to get my trousers on, stumbling over the leg holes. I feel his presence behind me before he speaks.
“I said, don’t … stop.” He places a hand on my shoulder.
I look up at him, confused and a little scared.
“Uncle Tom … please.” I murmur.
“Please what?” He smirks at me.
“Please …” I beg.
He pushes me back onto the bed and spreads my legs wide. He places his head between my thighs and inhales deeply.
I protest and struggle, trying to loosen his hold on my legs.
He groans quietly.
“You’ve been naughty Lucy. Very naughty. You shouldn’t be watching that, or doing … that.” He mutters at me. “Now, I think we should call someone? Don’t you?” He inhales deeply again, his head still between my thighs. I feel something wet and hot run up the inside of my leg and it makes me gasp.
“You like that don’t you Lucy? We should call Steve. Uncle Steve. What do you say?” He raises his head to look at me.
“Uncle Tom, please. Let me …”
He cuts me off. “Let you what baby? Let you cum? Let you touch yourself? No. You can’t touch yourself, but you might cum.” He flashes me a wicked grin.
My eyes fill with tears at the thought of what my own uncle is going to do to me. I turn my head away from him and gasp loudly as he pushes two fingers into my love hole. He shoves his fingers in back and forth as I stare at him, my mouth open and my eyes wide.
“Don’t cry sweetheart. This will be good. I promise.” He tells me.
He removes his fingers and takes out his mobile, hitting in Uncle Steve’s number he waits while it rings.
“Steve. Get your backside round to Lucy’s … Yeah. It’s time.”
He chuckles to himself as he puts the phone away and advances on me.
“No… No…” I stutter.
He grabs me by the arms and drags me off the bed pushing me to my knees.
“Don’t be a party pooper Lucy. You need to be taught a lesson. Uncle Steve and I are going to do that.” He pulls his jeans down and his erection springs out, right in front of my face.
He grabs my chin roughly and uses his other hand to rub his mushroom head up and down my cheek, along my nose and over my lips. My eyes start to tingle and I squeeze them shut. I don’t want to cry in front of Uncle Tom. I won’t let him see me cry.
He rubs his velvety head along my lips again, pushing the tip against them, trying to open them. I shake my head as he squeezes my chin harder, the tip of his cock still resting on my lips.
“You know you want to. Open up.” He growls at me.
I open my eyes to look at him, to plead with him, but all I see is a man that knows what he wants. His eyes full of lust and a fierce spark. I deflate inside, knowing that this is going to happen whether I want it to or not so I give in and open my lips.
He pushes the end through my lips and beyond my teeth, grabbing the back of my head he pulls me towards him, burying his cock further into my mouth and making me gag. I push back against his hand but this only spurs him on more and he starts to thrust himself into my mouth.
I wrap my lips around his hard shaft and begin to suck, hearing him chuckle to himself as he continues to thrust into my mouth. I gag a little more as he thrusts his cock all the way in, resting his balls against my chin.
“Oh yes. Keep sucking on Uncle Tom you little whore.” He pushes himself further into me, his balls moving up and down my chin.
I hear the bedroom door open and close and someone kneel behind me.
“She’s enjoying that isn’t she Tom?” Uncle Steve laughs from behind me. I look up at Uncle Tom and see him smile at his brother. It scares me.
Uncle Steve runs his hands up my back then rests them on my ass. He reaches round and slips a finger between my cunt lips. I moan around Uncle Tom’s cock as Uncle Steve continues to slide his finger up and down.
With his other hand, he pulls down my vest straps and swiftly un-hooks my bra. Reaching around the front, he yanks down the cups and I feel the cold air hit my already puckered nipples. He kneels behind me and I feel his hard dick pressing against my back. He slips a finger inside my sopping cunt and whispers in my ear. “We are going to fuck you. Fuck you so hard you’re going to cum.”
He nips at my neck and rams another finger into my cunt. I moan again and suck Uncle Tom’s cock harder. He grunts, his hands pulling at my hair and he slams himself harder into my mouth, his cum seeping out and overflowing out of my mouth. He sighs before pulling himself out of me and wiping any residue between my breasts.
He kneels in front of me and watches Steve pushing his fingers in and out of my pussy. I close my eyes, knowing that my lips will be glistening and my clit will be engorged. Just as much as I don’t want this, I do want it. Uncle Tom places his mouth around my pert breasts and nips at my nipples with his teeth. I jump slightly, which only makes him laugh. He pushes his body against me and I feel his cock hardening again already. Uncle Steve moves from behind me which allows Uncle Tom to push me backwards. He practically pounces on me; his whole weight on my body, his cock nestled against my mound.
I feel his member twitching against me, making me throb. I moan loudly and push my hips up.
“I told you she was a whore Tom. Like mother like daughter eh?” Steve says.
Uncle Tom lifts my legs up into the air, bending me over double so that he can ram his cock into my cunt, making me yelp in pain and squirm in pleasure. He thrusts himself into me forcefully, sliding up and down, his whole length inside me. He shifts his body so that he is resting on his legs, from above me, his cock still buried deep inside my sopping cunt.
I gasp as I feel cool air hit my puckered little asshole and then a wetness. Uncle Steve is licking up and down between my ass, his tongue hitting my virgin asshole. I groan as he licks the rim and places more pressure on my hole.
Uncle Tom grabs my face with his hand and looks me in the eyes, an evil grin spread across his face. His eyes gleam as he pushes himself into me. I feel a wet blob land on my ass and then Uncle Steve’s finger rub it up and down between my cheeks. His finger pushes against my hole and the tip pops through.
“No… No! Please!” I beg, squirming to try and get away. “Shut up! Shut up and take it you whore!” Uncle Tom growls at me, slapping my face.
As his hand hits my cheek a second time, Uncle Steve slams his full length into me. I scream with pain as his huge cock splits me and I feel his balls resting against my ass cheeks.
They both laugh while I scream and neither stop nor slow to reduce the pain. They both pound me harder with each thrust, working together to find a rhythm that suits them both. I focus on the ceiling and listen to sounds that the three of us are making.
Eventually the pain starts to go and I feel pleasure. I’ve watched videos of double penetration and boy does it make me wet, but I never thought that it would happen to me. I grab Uncle Tom’s legs with my hands and bite down on my lower lip. I whimper as one moves out and the other moves in. My pussy throbs and I feel the beginning of an orgasm beginning to build. I moan louder and open my mouth, letting out a scream as my body shakes and I start to gasp for air.
Uncle Steve pumps harder into my ass, grunting with each thrust. I groan louder as he thrusts hard into me before exploding his hot seed into me. I grunt as I felt it seep into me and I push my hips up, wanting Uncle Tom to screw my pussy harder. I watch Uncle Tom’s face as he realises that I’m asking for it. He rams himself further into my pussy and pounds into me with each thrust. He groans out loudly as he reaches climax and he thrusts himself hard into me to spread his load once more.
We all lay there for a few moments, panting, until Uncle Steve pulls himself out of my ass and Uncle Tom removes his cock from my pussy. They look down at me, my legs now wide open and spread on the floor.
“What have you learnt today young lady?” Uncle Tom ask me, smiling.
I pause, hesitating before answering.
“That you two know how to fuck.” I reply with a slight smile.
I looked-down at my phone, at a text message which had just arrived from my 19 year-old niece Lisa. “There’s something wrong with her truck”. I told my wife flatly before I had even read the message. After all that seemed to be the only time I ever heard from Lisa was when there was something wrong with the old Ford Bronco I had bought her a year or so previously. I knew she’s busy and that she truly appreciated the truck so I don’t really mind, Lisa is (for the most part) a good kid who goes to school full-time and works every weekend it seems so I don’t mind helping her out.
Sure enough the text was about her truck. She said it was making a loud squealing noise when she started it up. I guessed the fan belt needed to be replaced and I knew the truck was close to needing service anyway so I told her to bring it out when she had a chance and I’d take a look at it. Lisa replied that she was working an early shift Saturday and had the rest of the weekend free. My wife then reminded me that she and her Sister (Lisa’s mother) would be gone this weekend to visit a friend who lived several hours away. So this would be a good weekend for me to work on the truck.
I texted Lisa and told her Saturday would be fine. I told her she could drop the truck off and I’d let her take mine hers was fixed later in the day. She replied that she wanted to stay and work on it with me since it was an older truck and she wanted to know how to fix it when it breaks-down. She had helped me do oil changes and a brake job once or twice before so I told her that would be fine, although I knew that working alone I’d have the truck done in a couple of hours however it’s hard to say no to a 19 year old with perky tits, a skinny waist, blonde hair and deep blue eyes you could get lost in. Suddenly working on an old Bronco sounded like more fun than I had imagined.
A couple of days later, right at noon I watched Lisa park her Ford Bronco in front of my garage. We exchanged pleasantries as I checked a few things then Lisa asked where the coverall’s she’s worn before when she’s helped me work on her truck were.
“You don’t have to help me. Just take my truck and come back in a couple of hours.” I told her.
“No, I want to…I mean it’s all stuff I should know how to do anyways right? Besides, I never get to see you.” She added
I couldn’t argue with that. As I said it seemed the only time I saw her was when there was something wrong with her truck or she was broken-up with whatever boy she was dating at the time. What was wrong with the truck didn’t appear to be very serious so I surmised this visit must have something to do with some pimply-faced adolescent.
“How’s everything with you and Ken?” I asked her. As soon as I said it I could see tears starting to form in her eyes. A moment later she burst into tears and gave me a tight hug.
“He left me for some girl he met on-line on the east coast. I guess she got him a job and everything so he just up and left. Just like that.” She said through deep sobs.
Great. Now I get to play car mechanic and psychiatrist all at the same time I thought to myself.
I’m not a real deep guy so I told Lisa that working would get her mind off her lost love. I retrieved an old pair of coverall’s, the kind with a long zipper on the front, long pants and short sleeves. A lot of mechanics wear them to keep their clothes clean. I retrieved a smaller set which fit Lisa’s slender frame perfectly from a cabinet in my garage and Lisa went inside the house to change
I was right about the truck, all it needed was a new belt and an oil change and a couple of other small things. I could have had it all done in an hour or so but since Lisa was helping (and genuinely seemed interested in what I was doing) it took a little longer. I had to laugh though when while rolling around under the truck on my creeper Lisa’s tits got hung-up on the frame of the truck. Lisa and I both shared a hearty laugh after she’d wiggled-out from under the truck.
I noticed that the longer we worked on the truck it seemed the lower the zipper on the front of Lisa’s coverall’s worked it’s self. At first I thought it was on accident but when I casually noticed that it appeared Lisa was only wearing a bra underneath. Very slutty. It made me wonder what else she had in mind.
The brakes on the front of the truck were close to needing replacement so I changed those as well which of course meant I’d need to test drive the truck to make sure everything was working well.
I thought it would be a good idea for Lisa to drive since she drives the truck everyday and she knows how it normally drives. I climbed into the passenger seat and we pulled-out of the driveway.
The truck seemed to drive fine which was no surprise to me. What was a surprise is when we were stopped at a signal Lisa casually reached inside her coverall’s and began massaging one of her tit’s. I couldn’t help but stare to which Lisa replied,
“Oh, sorry. I had an itch.” She said with a sheepish grin on her face.
The light changed and we drove on, though I was having a hard time hiding the massive bulge which was growing in my pants. I had guiltily allowed my mind to wander to thoughts of what Lisa’s youthful pussy would feel like wrapped around my experienced cock. Sex with my wife had become a largely boring and routine event when it even happened. I allowed my mind to wander to the things I could do with and to this girl. The fact that she was my niece made it even more taboo and hot in my mind.
I knew that I wasn’t the only one who had taboo thoughts on their mind when a minute later Lisa made an abrupt turn into an empty shopping center and drove around to the back where no one was. Lisa parked the truck in a far corner of the parking lot, shut the engine off then without saying a word got out of the truck.
I watched as walked around to where I was sitting in the passenger seat of the truck. She opened my door, and then stood there and slowly lowered the long zipper on the front of her coverall’s, revealing what I had suspected all along. She casually stepped-out of the dirty overall’s and stood there wearing only a sheer black bra and matching black thong. We didn’t need to say anything, the next thing I knew I was watching the top of her pretty blonde head as she buried her head in my lap and began sucking my cock. With one hand I played with her hair while I allowed the other one to trace its way around her perfect, youthful ass. It wasn’t long before I pushed the thin material of her thong to one side and slipped a finger into her dripping snatch.
I could tell I wouldn’t be long before I came, which would be fine except for I wanted to see how far she was willing to go. I pulled her head up and kissed her deeply while one of my hands played with her nipples. After a moment she pulled her face back, gave me a grin and then pulled her bra off tossing it over me onto the seat. I took the opportunity to pull-down my pants.
That was all the invitation Lisa needed as she climbed onto my lap and teased my hard cock with her slit until I felt her lower herself onto me. She felt so good! Warm, tight, wetter then I think I’d ever felt before. Her back was to me and she leaned into me. My hands wasted no time in cradling those firm titties of hers. I then began fucking her, nice and slow. Soon she was bracing herself against the dashboard of the truck as my thrusts increased. I could see a couple of beads of sweat working their way down her face. I worked one of her nipples with one hand and her clit with the other through the material of her soaked panties. It wasn’t long before I heard her moan and felt her pussy contracting against my cock.
I knew I was only moments away from my own climax. I could feel the heat from her youthful pussy on my cock, her perky tits which seemed made for fucking, even her nipples which looked like they were sharp enough to cut glass worked to push me over the edge as now my own climax began washing over me. I came harder and longer then I had since I was probably her age. It felt incredible!
After we both recovered Lisa lifted herself off of my lap then bent-over and licked me clean. Sure I could tell she had obviously done this sort of thing before but I didn’t care. A few minutes later I climbed in the driver’s side of the truck and began to drive back my house. Lisa pushed her now soaked thong into my jeans pocket and sat there in the passenger seat wearing the same coverall’s she had been before, but with the zipper all the way open, teasing me with a quick glimpse of her tits or pussy whenever we weren’t stopped in traffic.
Needless to say by the time we returned to my house we we’re both more than ready for round two! The front door had barely clicked closed behind us and a moment later I had the coverall’s off her youthful body and her slender frame bent-over the arm of my sofa.
“Fuck my Pussy Uncle, I want to be your little slut!” She cried as I slammed my cock in and out of her tight snatch.
I was so wrapped-up in the moment that I decided to just let go as I allowed myself to once again pump my seed into her eager, waiting pussy. I almost fell-over the release felt so good. I didn’t pull-out until I saw a trickle of cum running down her leg.
We had about a day until my wife and Lisa’s mother were due back and we wasted none of that time; we sucked and fucked each other until barely an hour until the two were due back; we ended our sexual weekend with a dirty shower then made our way to the living room, fully-clothed. Lisa took a place on the sofa and I the recliner as we popped a movie into the DVD player. When my wife and Lisa’s Mother returned barely an hour later we re-counted a tale of how the truck had required a lot more work than we had first expected and had kept us busy for much of the weekend. The two women didn’t care and a few minutes later Lisa and her Mother left with Lisa giving me a knowing wink as they walked out the door.
Did it ever happen again? Oh, yeah. After all Lisa drives an old truck which requires a lot of repair. Maybe next time I’ll tell you about how much fun it is fucking my pregnant Niece!
Melissa was crushing, extra hard on John. She’d been so hot for him, he’d been the fantasy she thought of everytime she masturbated. Rubbed her clit raw, came over and over thinking of him. She was thirty eight and hadn’t had a boyfriend in years. This crush had been going on for years, nothing could stop it and she was ready to do something about it.
John was fifty two. He had dark hair and deep brown eyes. His look was one of mystery and rugged good looks. He was a sweet, kind man. He’d even provided her with a computer to use for her schooling while hers was in the shop. There was only one problem with John, he was married. Even worse, he had been married to her aunt since she was a child. John was her uncle.
She was determined to see if he was even the least bit interested in her either. She disconnected a few wires from the back of the computer and made a call to him.
When he answered, he knew it was her, “Hi Liss, How’s school going?”
“Not too good, Uncle John. I woke up today and tried to turn on the computer. It’s not working and I have a paper due by the weekend,” she moaned.
He checked his calendar for the daily plans before telling her he’d be over by noon to look at it. She happily thanked him for rushing over, hung up and went to her room to change.
Slipping into the short skirt and skimpy tank top made her feel extra sexy. She was dressing for him now and she hoped he liked it. She slipped into a tiny thong and fixed her skirt. Her shirt was tight, revealing. She didn’t wear a bra, her tits were too tight in the tank already. Her nipples pressed at the thin fabric.
She cleaned up her apartment while she waited. Pacing and replaying the scene in her mind. She planned to lean over next to him, letting him see down her shirt. Flirting and finally teasing him.
A knock on the door startled her from her fantasy. She painted her lips with sheer gloss before answering.
As she swung the door back, her uncle smiled. His eyes seemed to be searching her face, then dropped to her tits. She turned to allow him inside and closed the door behind him. As he walked away toward the room she used as an office, she clicked the lock and followed him.
She entered the room and he was kneeling on the floor. His muscles showed through the t-shirt he wore. She sauntered over after him, dropping to her knees beside him. He checked the cords and the outlet. She leaned in closer. His eyes drifted to her chest once more.
She looked up at him and smiled, “See something you like?”
His face flushed, lowering his eyes to his lap. He nodded, “I’m sorry about that, I just like a nice rack.”
She leaned over closer, “It’s okay Uncle John, I like when my tits get noticed.”
He turned his back to her, continuing with the computer. She left the room, returning moments later with two glasses of wine. Handing one to her uncle, she took the other and sat on the chair near him. His eyes found her face while he took a long drink of his wine. She smiled at him, sipping hers.
Suddenly, she tipped her glass too far and the red wine poured over the edge and down her shirt. The red spot grew, she rushed to peel the shirt off. She stood before her uncle with her nipples poking from her bare breasts. He gasped.
Knowing he was enjoying the show, she used the shirt to pat herself dry. This caused her nipples to poke out at him. He saw where this was going and sipped more of his wine.
She moved closer to him, “So, do you really like them? I think they like you.” She giggled like a school girl, showing him her bouncy chest, complete with rock hard nipples.
His face was crimson now, he could barely speak. “Nice, Liss, real nice. Now, go put a shirt on,” he said.
She moved even closer, “Are you sure you want me to do that? You could touch them first, see how they feel.”
He backed up a little, “I’m your uncle and I’m married, now go get dressed.”
She smiled, “You want me to undress you say? I’d be happy to Uncle John.” She unzipped the skirt, slipping it over her hips before letting it drop to her feet. She stepped out of it and closer to him.
His face was such a deep red, but the buldge in his pants was not from embarrassment. She leaned against him now, running her fingers across his chest, down his stomach and to the hard outline in his pants.
Rubbing her fingers across the length, she launghed, “It’s so big. I want to see it.”
He tried to move past her, but she wasn’t giving up. She had him cornered with no way out and he was going to hear what she had to say and he was going to fuck her. Here and now, he was definitely going to fuck her. She wasn’t letting him leave any other way.
He moved past her toward the living room, she followed close behind him. He sat in the overstuffed chair and before he could stop her, she plopped into his lap. She was now only wear the tiny thong. His cock was hard and throbbing, she could feel it against her ass.
Running her fingers through his hair, she smiled at him, “Just one time, just fuck me one time. You’ll never want to stop.”
He laid his head back against the chair, his eyes were closed and he was breathing heavily. His face was still bright red. She kissed at his neck, his shoulder. Moving down to his chest, she teased at his nipples. Pinching them between her fingers and then running her tongue over them. His breathing was hard now, faster.
She slipped off his lap onto her knees on the floor. She undid the button of his pants, allowing his cock to spring free. He groaned out loud, but he didn’t stop her. Glancing up at him, she saw that his eyes were still closed. She leaned over so her mouth was close to his cock.
It was close to eight inches, very thick and so very hard. She touched it with her tits, rubbing it between them. He relaxed a little, enjoying it. She gripped his hardness with both hands, stroking gently. Her mouth was almost touching the head of his cock. She was so close, she just needed him to say okay. “If you want your cock in my mouth, just put it there,” she whispered up to him.
That was all it took, his hand found her head. He grasped her hair and shoved her mouth down over his cock. As she bobbed her head up and down over his shaft, rubbing the outline of the veins with her tongue. He moaned and wiggled, pressing himself deeper down her throat. She never gagged, just took more and more.
Coming up for air, she teased the head. Flicking her tongue back and forth, she had him about to burst. She stroked him gently while her mouth massaged his balls. When she had him close to the brink, she lowered her warm mouth back onto his dick. Sucking and bobbing until his back began to arch and his legs lifted. Pressing his head deep in her throat, he unload a huge load of cum. She didn’t spill a drop, swallowing it all until his cock went limp in her mouth.
She got up and planted herself in his lap again. She nuzzled against his neck, resting her head against his shoulder. “Uncle John, I hope you liked it. It was just like I imagined.”
He opened his eyes, leaned his head over and pressed his lips to her forehead, “I loved it Liss, I owe you now.”
Without another word, he stood up while holding her. Carrying her over to the couch, he pushed her back on to it. Her hair fanned over the leather, he leaned over so his mouth met hers. Sliding his tongue between her lips, pressing his chest against her tits. The hardness of her nipples against him brought the spring back to his cock.
He kissed down her cheek, down her neck to her chest. Making his way down to each rock hard nipple. Squeezing them, nibbling them. His hand found it’s way to her wetness. Spreading her open, he shoved the thong aside and found her clit. His fingers rubbed against her sweet spot. Making her moan loudly, while his mouth suckled her nipples.
Kneeling between her legs, his face close to her snatch. He breathed in her scent, so fresh and sweet. Lowering his mouth to her hardened nub, he suckled her clit into his mouth. Teasing her with his tongue, flicking at her sweet spot. He was enjoying her pleasure, liked making her cum. He did it first with his mouth, then used his tongue for round two. She was so wet, the couch held a puddle below her.
His dick was hard again, he wouldn’t be able to resist sinking deep into her. He knelt on the couch between her thighs, lifting her legs to his shoulder. He watched her face, he couldn’t resist that face, the head of his cock pressed against her gaping love hole.
When she felt him enter her, she gasped. She had enjoyed the oral sex, she didn’t expect more. He was giving it to her though. Pounding deep into her before slipping out and pounding back in further and further. She reached her hand down to her clit, her legs were open and he could see all of her. Finding her sweet spot, she rubbed it faster and faster.
Her third orgasm was very powerful, her pussy gripped his cock tightly. She moaned and shook. He was almost ready too. Before he could explode, he stood and pulled her up. He tugged the thong off of her and let it fall to the floor.
Standing before him completely naked, he rested on the arm of the couch. Pulling her to him, he bent her over his lap. Slapping her tight ass, over and over. “You were a very bad girl Liss. Uncle John’s going to have to spank you now. You must be a good girl.”
Her ass was bright red, she was as horny as ever. Maybe even more so, his cock pressed against her belly, making her wetter. He stood and pushed her over the side of the chair. Her red ass was in the air and her cheeks were spread. He could see her clit, dripping wet.
Behind her, he pressed into her. Fucking her even harder, she moaned again, “Oh Uncle John, make me cum again. Please!”
Her begging did him in, his cock pressed deeper into her and her warmth made him explode. Filling her with his cum, making her scream out. Still inside her, he layed back on the couch. She was on top of him, her pussy dripping of his cum.
“Thank you for fixing my computer Uncle John,” she smiled.
“Any time sweetheart, call me any time.”
When my father died, I blamed my mother. Not for his death – the car accident that killed him was due to bad weather and a teenage driver – but for all of the unhappiness that settled on our home and stayed there after he was gone. My mother locked herself away in darkness, and tried to keep me there, too.
So I rebelled. I snuck out at night, didn’t come home for days at a time, skipped school, stole clothes and makeup from the mall, smoked pot, and drank anything I could get my hands on. Playing up my bad girl image, I modeled myself after Bettie Page, dying my brown hair a deep blue-black, wearing thick bangs, keeping my skin pale and my lipstick deep red. Skintight clothes paired with black or red patent leather shoes completed the look.
But it was just a sexy look. For all of the attention I received from boys, the kissing and pawing and fumbling in the dark, I never let things get out of control. Once, I let an older boy put his hand down my pants, but his probing fingers hurt, so I stopped him after a few moments and made him take me home. I avoided spending much time alone with boys after that.
So imagine my surprise when I arrived home one day to find my uncle, my father’s step-brother, waiting with my mom to stage some sort of slut intervention for me. He and I had once been close, but I hadn’t seen him since the funeral. As I stepped into the living room, he and I sized each other up warily.
Paul spoke first. “Maggie, we are concerned about your behavior. Your friends seem to be a bad influence on you and you are in danger of being permanently expelled from school because of your truancy. You are smarter than this, and I have a plan to help you make better choices for yourself.”
Angrily, I told him, “You don’t know what you’re talking about. You abandoned us after Dad died, and Mom has been more concerned with feeling sorry for herself than anything else. You can both fuck off as far as I’m concerned.”
“I thought that would be your response,” my uncle said. He turned to my mother. “I will take her in, then, and you probably won’t hear from either of us for a week or so, until we get her settled in and used to the routine.”
“Where do you think you’re taking me?” I demanded. “I’m not going anywhere with you. I have a life here!”
Uncle Paul ignored me. He and my mother discussed their plans for me, offering scant details that I could use to figure out what they had in store for me. I ran to my bedroom and found it stripped bare of my possessions. My mom entered the room behind me. I yelled at her, screaming at her for stealing my stuff. She said, “This is what is best for you. You will just have to trust us. I’m sorry things haven’t been good for us, but I do love you, Maggie.”
I pushed past her, heading for the front door. Uncle Paul grabbed me by the arm, then held both of my wrists in his one large hand and led me to his Jaguar like I was a naughty child. I would have fought like one, too, but I was beginning to realize just how worried my mom had been about me. He pushed me into the passenger seat and slowly fastened the seatbelt to secure me in place. As he pulled his hand back, his palm slid across one of my breasts and I gasped. Our eyes locked for a moment, then he stood up and closed and locked the door as if nothing had happened.
I watched him walk around the front of the gold car, his expensive suit not the least bit rumpled after manhandling me into his vehicle. He and my dad were only stepbrothers, and did not look at all alike. Dad had had curly, light-brown hair and cornflower blue eyes that matched my own. Uncle Paul had straight, almost black hair and dark brown eyes. He was also considerably larger than my father, easily 6’4, with broad shoulders and narrow hips, built like a swimmer.
After removing his suit jacket and carefully arranging it behind the driver’s seat, Paul climbed in and started the car. With a throaty growl, the sports car leapt forward as my uncle expertly navigated the residential streets and we made our way to the interstate. Once on the open road, Paul relaxed. He tugged his silk tie loose then tossed it behind him. He unfastened the top two buttons of his dress shirt and with a sigh, turned up the air conditioner.
I was cold, but I didn’t want to be the first to speak, so I didn’t ask him to turn it down. Instead, I looked out the side window, studiously ignoring him. After several silent minutes passed, he said, “I understand why you went with the Bettie Page look, Maggie. Your figure is very similar to hers – long legs, tiny waist, and all the rest. You even have good-sized nipples, like she did.”
Outraged, I turned to face him. I realized that my blouse did little to conceal my breasts with the seatbelt wedged firmly between them, and the cold air left my hard nipples clearly defined against the silky fabric. I said, “You really are a creep, you know that?”
Paul laughed. “Actually, I’m a nice guy. My niece has turned into an out-of-control slut, and when her mother called me, distraught and in tears, I dropped everything to try to help them both. But I do find it funny that you dress like a pin-up girl and then pretend to be offended when someone notices your figure.”
I looked away again and was surprised when he suddenly took an exit leading to a tiny town that I had never even heard of. After a couple of turns, he stopped in front of a doctor’s office. He said, “Don’t embarrass me here. I had to call in some favors to get you scheduled for a complete physical to assess your overall health and know if you can handle what I have in store for you. I know you aren’t going to like this, but please, just think of your mother. If you don’t comply, I don’t know what she will do.”
Feeling guilty over what I had put my mother through, I agreed to behave. The nurse quickly ushered us into a large exam room and handed me a paper gown to change into. My uncle turned his back as I stripped, quickly wrapping myself in the short, crinkly garment. It was a bland green that went from my neck to the very tops of my thighs, barely hiding my pussy from sight. It was open in the back, but the fabric was wide enough that I managed to arrange it to cover my ass. I perched on the edge of the exam table, nervously awaiting the doctor’s arrival.
An average-looking middle-aged man bustled into the room, wearing a white jacket and carrying a clipboard. He looked at the clipboard, then at me. With a smile, he said, “Okay, Maggie. It’s nice to meet you. I’m Dr. Matthews. Please lean back and let me get you settled in so that I can perform your examination. I’ll make it as quick as possible, I promise.”
He seemed warm and professional, so I slid backwards on the exam table, the gown riding up a bit to reveal the tuft of light brown curls at the top of my mound. I felt the back open up and cool air waft down my spine. I looked over at my uncle, who was seated in a chair slightly behind the exam table and to my right. He was reading a magazine and didn’t even look up, so I quickly laid back to cover my nakedness.
The doctor put my legs into the table’s stirrups, opening and exposing my pussy even further. I tensed up, but tried to remind myself that this was a normal part of a physical for girls my age. After all, I was eighteen. I should have had my first annual earlier this year, right? And my uncle wouldn’t be able to see anything from his vantage point. So this was all fine.
The doctor walked up to my left, securing my arm into a cuff. He explained, “This will help monitor your blood pressure during the exam – it may be a little tight, but don’t worry, it’s good for us to know what’s going on there. He walked to my right and secured my other wrist above my head, then attached a few electrodes along my forearm. He said, “These take other necessary measurements that will help us assess your overall health.”
The doctor settled down between my thighs. He pulled on gloves before stroking the soft hair on my mound. He said, “I need to remove this. It will just take a moment, but you need to hold absolutely still.”
I heard the ssssssh noise of a shaving cream dispenser and felt him spread the thick foam thoroughly across my hair. I watched him expertly maneuver a razor across the delicate flesh between my thighs, removing every strand of hair. He snapped off his gloves, which were covered in shaving cream, and used a damp washcloth to swirl away every bit of foam from my center. His bare fingers gripped my pussy lips as he opened them up, cupping the washcloth against my pussy and slowly grinding his palm against me. Without realizing it, I moaned at the sensation. He looked up at me and said, “You’re ready for the first part of the exam now.”
The doctor pulled out a small, silver capsule attached to a cord. He placed it against the top of my pussy, near my clit, then used a couple of clips to hold it in place. They painfully clamped on my lips, and I was about to protest when the doctor flipped a switch and all of it started to vibrate. The vibrations were low, but caused a liquid heat to immediately flood my body.
I choked out, “What are you doing?”
The doctor said, “Part of health is a normal sexual response. I need to see if you are properly sensitized, and will know in a few moments. So hang in there, okay?”
Nodding, I closed my eyes against the sensation. It was incredible. I wished it were more intense – as it was, the buzzing ignited my whole body but wasn’t enough to promise any satisfaction. Still, I writhed and wriggled and tried to find some sort of release, with no luck.
After several moments, the doctor made a harrumphing noise. Standing over me, he said, “This is highly unusual. You may need a little additional stimulation, so I’m going to try that now before we decide whether you are properly sexually healthy. There are two other erogenous zones that I think we’ll explore before I make a diagnosis, so bear with me.”
I nodded. He showed me a device that looked like a small black belt with a shiny, mushroom-shaped ball sticking out of the middle of it. Before I realized what he was doing, he had it fastened behind my head and the soft, pliable ball was nestled into my mouth. I must have looked alarmed, so he smiled reassuringly and said, “The tongue is highly sensitive. Stroke the little head and see if it helps you achieve release.”
As I focused on his instruction, I felt him suddenly cut open the top of my examination gown. He tore out a wide section, framing my milky white breasts with the green material. He plucked at my thick, pink nipples, and when they were fully extended, fastened first one then the other with a tight clamp. It stung, at least until he made a couple of adjustments and they started to vibrate. Although I was restrained, I felt my back arch and I undulated against the currents running through my most sensitive parts.
I heard a quiet moan behind me and suddenly remembered that my uncle was in the room, but I was too wrapped up in the examination to be properly embarrassed by his presence. The device in my pussy suddenly ratcheted up the intensity, and I came, crying out against the gag and thrashing against my various restraints. The buzzing that had brought me pleasure now caused pain as it continued its work, unabated, on my overly sensitized clit.
The vibrations in my pussy stopped and I relaxed. The doctor removed the clamps from my tits, my long nipples now red and engorged, standing straight up from my full breasts. Dr. Matthews bent between my thighs, pulled on another pair of gloves, and slid his fingers into my drenched opening. After a few seconds, he looked up with surprise. “Paul, come here and check this out.”
My uncle quickly walked around to the foot of the exam table, my nearly nude body spread out in front of him. I flushed with shame as the doctor guided Paul’s hand into my opening and I felt him push up against the barrier inside me. Paul looked at me and said, “Are you really a virgin?”
I nodded, still gagged and unable to speak. Tears leaked out of the corners of my eyes. He and the doctor spoke in low voices as they both continued to stroke their fingers in and out of my tight opening. Much to my embarrassment, I felt my juices start to flow again as my clit recovered from my previous orgasm. Paul finally looked at me and said, “Maggie, I wouldn’t have taken you from your home if I knew you were still a virgin. But I can’t bring you back to your mom – she would be devastated. We’ve decided that Dr. Matthews is going to provide me with a way to help you with this… situation.”
I tried to tell him no, not to do whatever it was that he was thinking of. But nothing came out but a few muffled whines, and Paul didn’t seem to notice. He and the doctor removed what was left of my gown, and Paul said, “I need a few moments to prepare for this, so I’m going to have to touch you a bit first.”
Paul came around to my side, ignoring my whimpers and my attempts to plead with him. He cupped my tits firmly with both hands, massaging them painfully, then twisted both nipples lightly with his fingertips, stretching them out further than I would have thought possible. He bent his head, holding my nipple in his teeth as he swirled his tongue all over my sensitive flesh before sucking and toying with it. I groaned around the intrusion in my mouth. He leaned across me and repeated the process on my other nipple, teasing me until I was all but sobbing with pleasure into the ball gag. When his mouth left my body, I was bereft, wanting more of his caresses.
Suddenly the doctor reappeared, making adjustments to the table. I felt the hydraulic lift jerk once, twice, before the exam table was slowly lowered, me with it. The table tipped, angling my head downward as my hips were lifted. With a final jolt, the table stopped moving. I felt my tits bobble against each other, settling high and firm on my chest. I could see the naked folds of my pussy, puffy and open, as eager as the rest of me. My whole body was on view for these two men, and I had no thought other than what wonderful feeling I would experience next.
Through lowered lids, I watched as Paul unzipped his pants, letting them fall to the floor. His cock looked impossibly huge, but he rubbed it firmly against my dripping slit, bumping the swollen tip against my clit slowly, once, twice, three times. I gurgled eagerly from behind the gag, thrilled by the sensation.
The head of his cock jabbed into my tight passage. I grunted in surprise, the pain dulling my pleasure as with a sharp cry of triumph, my uncle pushed past the delicate membrane deep within me. My body tightened and jerked against his invasion. He paused and said, “Relax, Maggie. You will love this in a moment. Take a deep breath.”
I did as he told me, and he pulled back slightly. My relief was short-lived, however; he slammed into my tender cunt, stopping only when his balls slapped against my ass. I cried out in pain, but he and the doctor shushed me. The doctor began massaging my breasts, and soon Paul’s finger reached between us and he rubbed my clit in a matching rhythm, his cock still buried deep within me.
The pain disappeared, and ecstasy replaced it. I slurped around my gag, a wet chant of yes, yes, yes as both men sped up their ministrations. Lightning struck and I shook and keened as my second orgasm reverberated through me. Paul took the opportunity to begin thrusting into me with vigor, but rather than hurt, all I felt was a wonderful and complete fullness. I felt a slow burn begin deep in the center of me, and knew a third orgasm was not far away. But Paul was at his limit, and with a final thrust and a bellow, he scalded my insides with his cum.
As he pulled out, I whimpered, wanting that one last chance at bliss. The doctor finally let go of my tits and took Paul’s place between my outspread thighs. Without hesitation, he unzipped his trousers and thrust into me. Furiously, he pistoned his hips, pumping into me like some kind of robot. While he did not have nearly the girth that Paul did, his frantic pace set my body afire. As I screamed out my delight, my pussy convulsing around his cock, he filled me with his juice, then collapsed on top of me. The room went black.
When I woke up, I was still naked, but my body had been thoroughly cleaned. I was damp from the sponge bath the doctor had apparently given me, and he was rinsing out the tub in the sink in the corner of the exam room. Paul was sitting across from me, once again fully dressed, and he smiled warmly. “Maggie, you are almost too beautiful to allow you to get dressed. But don’t worry, we won’t put too much clothing on you.”
He walked over and pulled me to my feet. Paul slowly unbuttoned a white blouse that had been hanging from the back of the exam room door. He brought it to me and I held out first one arm, then the other, as he pulled it over my back. Before buttoning it, he reached up and caressed my tits, rubbing his palms against my hardening nipples. Then, with a sigh, he fastened the three middle buttons on the shirt, leaving two buttons above and below undone. You could see from my belly button all the way down to my bare pussy, and a generous amount of cleavage pushed against the open top. My nipples were clearly visible through the fabric, especially now that my uncle had teased them erect.
He pulled a pleated plaid skirt from the hanger on the back of the door. I stepped into it as he slowly tugged the short skirt into place. Paul then nudged my legs apart with his own, stepping close and reaching behind me. His large hands cupped my bare ass under the skirt, pulling me tight against the growing bulge in the front of his pants. His hands slid more firmly under me, a couple of fingers tracing my dampening slit. I reached up and wrapped my arms around his neck, making as much contact with his body as I possibly could. He lowered his mouth to mine for a passionate kiss, his tongue probing into my mouth as his fingers probed into my pussy. It was heavenly.
Paul whispered against my lips, “Let’s get back on the road, Maggie.”
I nodded and reluctantly let go. He gestured to a pair of simple shoes, dainty kitten heels with a leather strap across the top of the foot. I slipped them on as Paul and Dr. Matthews shook hands. Dr. Matthews grinned at me as I followed Paul out the door.
Once back on the highway, Paul said appreciatively, “You are incredibly sexy. We just fucked, and I’m hard again.”
I looked down at his lap. The bulge looked like it was ready to burst through the fly of his trousers. I felt a now-familiar wetness spread through me. Paul reached down and unzipped his pants, his 9-inch cock rising like a phoenix from the ash-grey fabric. He said, “Unfasten your seat belt, get on your knees in the seat, and take me in your mouth.”
I didn’t even think to tell him no. I just did what he said, bracing my arms against the seat back and the dashboard as I lowered my head and tentatively licked the deep red tip of his cock. Impatiently, Paul pushed my head down, so I struggled to take more of him into my mouth, pulsing my tongue against his shaft as I slid further along his cock, my ass stuck up in the air.
As I worked on his cock, trying my best to make Paul happy, I felt him reach behind me. He flipped my skirt up over my back, so my most secret parts were fully exposed. When I heard the tick, tick, tick noise of his turn signal, I realized that he was going to pass someone on the left, so if they looked at the car as we went by, whoever was driving would get an eyeful of my bald, freshly fucked pussy and tight little ass.
I tried to protest, pulling up so I could tell him no. Paul pushed firmly on the back of my head, forcing even more of his dick into my mouth. The thick head of his cock bumped my tonsils and I gagged, giving him even more access to my throat. He shoved harder, until my nose was nestled in the crisp hair at the base of his shaft. Desperate for air, I sucked furiously and tried to breathe out of my nose as my splayed lips drooled against him.
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!
1 – Monday
It really has been one hell of a week and more to come maybe, though I really am not sure how this is all going to work out. An awful lot has happened since last Monday, I am just beginning to make sense of it. Or at least, some sense.
On Monday I decided to ‘shake myself out of it’. Out of the depression of the past six weeks at least. I have been living here, in my Uncle Jack’s house, since that awful day six weeks ago. Since the car crash.
Both my parents were killed. OK, at my age, I should have been able to cope with that, but on top of all my other problems it was a massive shock. Just before that my Dad’s business folded, the shop we were running together had to close. Blasted hypermarkets, no good at all for the small retailer, the business I had helped start and get going fifteen years ago, it just couldn’t compete. Then just after Christmas it really went wrong, unsold stock, bills, Dad just had to give it all up to pay the creditors.
Which left me jobless. Then to top it all two days later that big motorway pile-up, my parents’ car was right in the middle of it. At least that put paid to any stories about suicide, the television pictures proved that. But the insurance money, what little there was, all got taken to help sort out the debts. The house too, the extra borrowing to try to keep going had eaten up that too.
Which left me on my own, Not entirely penniless, I know now why Dad insisted I keep an account in my own name, he wouldn’t let me put everything of my own back into the store. Thankfully Uncle Jack, who had married Mum’s younger sister, he took pity on me at the funeral, offered me a place to stay, he is on his own right now. He has had his own share of tragedy. His wife, my Aunt Jean, herself died about four years ago, a terrible wasting illness which left her fading and in some pain for about three months at the end. But at least he still had Emma, lovely Emma, she was away at college. He was on his own in this big house and welcomed some male company.
Well, yes. And we did get on together, he was very understanding, didn’t push me, said I could take all the time I needed to think about a job, a place of my own. For five weeks we got on very well indeed, went to a couple of football matches, in the pub a few times, a couple of rounds of golf, helped each other with cooking and housework and so on. Not that he was at home much in the day, his own business has really taken off, he spends loads of time at the office, with clients and so on. So in the day I have been left to my own devices.
So to last Monday. It had really been coming for a while, I just KNEW it had to happen.
Twice in the previous week I had, for the first time in several years, indulged in my own rather peculiar hobby. Dressing up, that is. I just love it, wearing sexy underwear, a tight dress or skirt, high heels and so on. I know it’s a bit odd but apparently quite a lot of guys get a kick out of it, dressing in women’s clothes. I had investigated my cousin’s wardrobe and found several items which would fit me. And more surprising, a lot of Aunt Jean’s stuff in a wardrobe in my Uncle’s room. I knew, I had heard several times from my own family, that Jack had taken her death very badly indeed, they had been extremely happily married for nearly twenty years. But I hadn’t realised he was still so affected, even after this time he had still not sorted or got rid of many of her clothes.
She had been a very attractive woman, as had her sister, my mother. Whether subconsciously I wanted to bring her back, or my Aunt Jean, I don’t know. But having not ‘dressed’ for maybe ten years myself, the urge returned when I saw her outfits, her shoes, even a wig. With those and some of Emma’s stuff I thought I could do a good job on myself.
I had twice the previous week tried on some things, found some sling-back shoes I could adjust to nearly fit. That Monday was to be my first full try-out. Uncle Jack was going in late because he was having dinner later with a client, that gave me over nine hours on my own. And some of it in semi-darkness, I could maybe even go for a short walk in the garden and enjoy the breeze on my nylon-clad legs.
When Uncle Jack set off that day I moved into action, catching a bus into town and doing a little ‘femme’ shopping, I bought a pair of tights for myself, some panties, a few makeup items and pieces of jewellery. I got back to the house late afternoon and took a long, hot, sweet-smelling bath. After a light snack I spread my choice of clothing out over the bed in Emma’s room. I felt the need for a slightly feminine environment to take on this task. It really didn’t take me long, memories of my dressing up years earlier came flooding back, the thrill of sliding my legs into tights was still there. I had bought a pair of American tights, pantyhose they were called, not too sheer but nice enough to feel really good.
The make-up skills too, came back to me. I had always prided myself on my accomplishments there, on taking care to overdo it just a little to give a really feminine appearance to my masculine face.
And within an hour I was there! Done! Finished! I stood looking into the long mirror in Emma’s room, delighted with what I saw. A woman. Definitely, none of my old skills had gone. A smart and, I like to think, rather attractive woman, tight white sweater – Emma’s – over black bra – Aunt Jean’s – with a short-ish deep blue skirt, black tights and high-ish heels. I managed the shoes quite well even though they were a little small for me.
The wig had puzzled me at first but then I realised. Aunt Jean, by all accounts, had not been a vain woman (unlike me, I thought!) but she did like to look nice. And when she began to get ill her hair was badly affected. She must have bought the wig then, to delay the onset of the effect of the illness on her appearance. That partly explained it. The wig was basically her own colour and style, a deep red shade, basically the family colour. My own hair was the same, my Mother’s had been similar, and Emma’s too, though hers had become rather lighter after two months holiday in Australia last year.
What it did not explain was the other wig, longer, fuller, and a deep blonde shade. Both wigs were a far better quality than the one I had used some years earlier. I stuck to the red one, thinking it would go better with my basic skin tones.
I spent an hour wandering round downstairs, posing, sitting and crossing my legs, enjoying again the feel of nice hosiery on my legs and thighs, then went for a short walk down the garden in the evening sun. I realised the time was beginning to get on and headed back to the house, watching my reflection in the big picture window at the back.
I looked towards the back door.
Uncle Jack was standing there, silhouetted against the light! My heart missed several beats. Then before he had time to say anything else, I pushed past him, across the lounge and up the stairs. My mind was in a turmoil. Blast! I had NOT got the time wrong, he was not due back for several hours yet. But too late for recriminations, the damage was done.
“Timothy! Wait!” Uncle called after me.
I heard his footsteps, heavy on the stairs behind me. I dashed into the closest room and, since there was no lock on the door, quickly grabbed a chair and jammed it in place under the knob. Immediately I saw the knob turn and the door move, but it would not open. I sat on the bed and quickly tore off my wig and began to unfasten my shoes.
I realised I couldn’t change, not fully anyway, most of my clothes were in my own room, I had dashed into Emma’s bedroom in my hurry. I paused and breathed deeply. I heard Uncle Jack’s voice outside the door.
“Timothy, please, wait. I’m not mad at you but we need to talk. Just stop and think for a minute.”
That I had done.
“Are you listening, Timothy? I have something important to say. Please. I am going down to the kitchen, I need a drink and I think you maybe do too. Please, don’t rush into changing or anything. Come down as you are. OK?”
“OK” I called out.
I heard Uncle shuffle and go down the stairs. I moved the chair, opened the door and, in stocking feet and without my wig, I followed.
In the kitchen, Uncle Jack was just getting two cans from the fridge. He opened both and pushed one across the table towards me, taking a long drink from the other. He sat on opposite sides of the small table there, silent for half a minute, drinking, thinking.
“Timothy, I am glad you came down. And I am glad this ” – he looked me over, acknowledging my incongruous appearance – “is out in the open.”
I shuffled slightly in my seat, nervously. I was a guest in this house and I had abused the hospitality offered to me. I wondered how Uncle Jack was taking this so calmly.
“Right, let me say what I need to say”.
Here it comes, I thought, shuffling even more, and for once not really enjoying the thrill as my skirt rode up to expose my thighs.
“I can’t pretend not to be concerned about this. But you may be wondering just why I am taking this so calmly.”
Was Uncle Jack a mind-reader?
“But when you dashed past me to go upstairs, and I properly realised what was going on, I was annoyed – for about 15 seconds. And then I remembered something your Aunt Jean and I discussed during her last few weeks. Basically it gave me a whole new outlook on life, in one short sentence, it dictated how we spent our remaining weeks together.”
I waited, wondering what Uncle Jack was going to say.
“In simple terms, life is too short, if there is something you really want to do, go for it!”
We spent nearly half an hour talking about the situation, why I did what I did, what I felt like, was I gay, did I ever go out dressed and so on. At the end of it I was much more relaxed, it had been really weird at first discussing such things with another person, specially Uncle Jack. But I did feel much more relaxed. I had assured him that in no way would I embarrass him by going out dressed, in fact I never had, until that day absolutely no-one had ever seen me ‘dressed’.
“OK then, Timothy. It’s beginning to get late and I have to be up in the morning. But first – like I said, if you want to do something you should really go for it. So. Before we turn in, how about letting me have a proper look at my ‘niece’? Go on back up while I clear things down here, put on your wig and re-fix your makeup, let me see just what – or rather who – we have been talking about.”
I padded back upstairs and sat to re-do my makeup – I looked AWFUL. Whatever must Uncle Jack have thought of me? My mascara was smeared and without the wig I simply just looked like a man dressed rather stupidly. Which was not the impression I wanted to give. I took my time, removing and re-doing makeup took longer than I thought. I’d never had to do that before.
Finally I was ready. I stood and slid on the red wig, it really was a much better quality than I was used to, and slid my feet into the shoes.
“Timothy, are you OK? Ready?” I heard Uncle call from the foot of the stairs.
“Coming Uncle” I replied, my ears jarring a little at the un-feminine tone as I shouted. I must try, I thought, to keep my voice gentle, I imagined I could imitate a more feminine tone.
I headed down the stairs and into the lounge where my Uncle, sat with his newspaper, looked up. And, I was absolutely DELIGHTED to see, raised his eyebrows and grinned as he saw me, fully dressed, really for the first time.
“Well, Timothy. I am amazed. No, really, amazed. I only got a glimpse before but you really have done an exceptionally good job. If I didn’t know the truth I think I really would take you for a woman. Please, just walk around a little, let me see.”
And I did just that, strolled round and posed just like I had done before, but this time for an audience.
“OK, young lady, I promise you, you really do look the part. I’m glad you did this, Timothy, it does at least show me you are in some way serious about this, that means I have to be serious about it too.”
We sat together and talked about the whole thing for several minutes more, the Uncle Jack rose and held his hand out towards me. I took it, and gave him a little squeeze.
“Uncle, thank you. Thank you so much for being so supportive, so understanding. You don’t know what this means to me.”
“Timothy. Just one thing. Please. That wig, you will realise, it is – or rather was – Jean’s. She got it when she became ill. Well, you look very much like her when you are wearing it. There is another wig upstairs somewhere, I think I might prefer it if you tried that one. You do have in some way the ‘Wilson’ face, you have the look of Jean, your cousin Emma does too. When I saw you, just for a split second ‘ – I thought – “
“Uncle Timothy, I am sorry, I never would have – you know – if I had really thought -”
“That’s OK, Timothy, you weren’t expecting to be interrupted, were you?” he continued.
That night, after six weeks of unsettled nights, I slept well.
2 – Tuesday
The next morning over our usual light breakfast, Uncle Jack didn’t refer to the previous evening’s activities until the end, as we were clearing away the dishes.
“Timothy, I have to go now. Back at the usual time, I hope, just so you know.”
He smiled, an acknowledgement that many things still stayed the same despite my revelations. I thought of dressing again later that day, but didn’t. As a ‘thank you’ I spent the day gardening, mowing the lawn, something Uncle Jack didn’t like doing. He had put it off the previous weekend, so I did it for him. And did a good job too, though I say it myself. Uncle Jack did come home at the usual time, I had a decent meal prepared for the two of us. We watched a little TV – television!! – and then Jack wanted to show me something upstairs. In his bedroom he opened the wardrobe where I had found Jane’s skirt the previous day.
“That top you were wearing last night, Timothy, I think it was Emma’s. I know you couldn’t really have asked me but – I think it would be best not to wear her things. But all this was your Aunt Jane’s, and I KNOW I should have sorted it before. It has been four years now.”
I had a proper look at the contents of the rack in there, I could see more than I recalled.
“But now I can put it to good use. How about you sort through it all tomorrow? Take any things you want for yourself and bag the rest, we’ll take it to the charity shop in town. OK?”
I was rather amazed. Uncle Jack was actually giving me clothes to dress in, as well as permission to do so. Mt reply was a bit flustered.
“Uncle Jack, I couldn’t, these were Aunt Jean’s clothes, I -”
“Nonsense Timothy, you’ll be doing me a favour, I’ve just put off sorting these clothes too long. Please?”
I just had to say yes.
“But I’d like to do something for the clothes, how about I give an extra donation to the charity shop, to sort-of pay for them. In a good cause?”
“Great idea, Timothy.”
3 – Wednesday
So I did just that, I spent the next morning going through the wardrobe in the big bedroom, sorting through the clothes in there. Many were – and were always going to be – too small for me. I ended up putting these and, I very much regretted, most of the shoes, in three large bags to go to the charity shop. It was a surprisingly exciting time, but sad too, remembering that all these had been worn by my late aunt. By mid-afternoon I was nearly done, the final item I discovered was a suit. In one sense an ordinary suit, jacket and skirt, but I was enthralled by it. It is a deep grey with a thin maroon stripe, very classy, an ‘executive’ suit. Expensive, obviously, and either hardly worn or very well looked after. I looked at the clock – two hours, that’s how much time I would have if ……
I headed for the bathroom, stripped and showered, then began my makeover once more but this time I was not out to impress just myself. Within ninety minutes I was down in the kitchen, assembling dinner, well, not a full meal today, more of a major snack, for the two of us. The suit fits me, I am delighted to say, like a glove, mid-length jacket over a classic white ruffled blouse, tight-ish skirt, straight, hemline about eight inches above my knees. I had done my nails too, in a deep-ish pink gloss which matched my lipstick, and I was very surprised the wig colour, the shiny ash-blonde, suited my own colouring so well. The wig was also a more glamorous style than the straight-cut red one. This one is longer and fuller, more curly, definitely more ‘glam’.
I was sitting at the dining table when Uncle Jack came in, my legs crossed and showing quite a bit of thigh. As he entered I sipped at the glass of white wine I had just poured, then I smiled and offered a glass to him.
“I thought this would go rather well with the meal” I suggested gently, holding out the glass to him, trying to keep my voice quiet and, I hoped, convincing.
“Well, what do you think?” I asked, somewhat nervously.
It was obvious I wasn’t asking him about the wine. He sipped the glass himself, looking me over, then smiled.
“Timothy, I am VERY impressed, I thought you looked good on Monday night, right now I am absolutely delighted. I see an attractive woman. Very smart, well groomed, one who takes care of herself, who likes to look good and works at it. Very good indeed.”
I glowed with satisfaction. ‘Herself’ He’d said ‘herself’.
“Thank you, Uncle Jack, you don’t know how much that means to me.”
And I spent the whole of that evening, dressed, in company, happy. We had our meal, I served it, cleared away and then did coffee. We sat together afterwards discussing things, changes, then Uncle Jack surprised me.
“Timothy you really do make an attractive woman. Look, my car is still out, let’s go out.”
Out? Out?!! I was aghast at the thought, Jack could see I was beginning to panic.
“Hang on, Timothy, nothing major. There’s a little woodland about half a mile from here, Emma and I often go there to relax in the evening, a short stroll along the path there, that’s all I am suggesting. Nobody else around usually. How about it?”
So we did. Uncle Jack drove us there and we strolled side by side along the path, about 200 yards, then back towards the car. He could see I was thrilled by this until, just as we approached the car, another pulled up beside his and another couple got out. An older man, maybe nearly sixty, and someone I took to be his wife were headed towards us, hand-in-hand. Jack grabbed my hand, I was shaking.
“Timothy, calm down, just keep on walking, they won’t give you a second glance I promise.”
And they walked right past us, Jack acknowledged the man’s greeting with a ‘Good Evening’ in reply, and we strolled on. I was relieved to sit in the car again.
“Sorry, Timothy, he DID give you a second glance.”
Obviously I must have looked worried.
“He was checking out your legs!”
4 – Thursday
The next morning we were both up early to breakfast together. I was ‘Timothy’ again. Uncle said he was due back a little late that day, he had a business lunch and wouldn’t need a full meal. Again he was helping me, letting me know I could greet him dressed if I wanted to. I really did want to but that day it would not be possible. I had a ‘date’ myself, or rather an appointment, at the employment bureau in the afternoon.
I was after a job, I couldn’t just hang round living off Uncle Jack full-time. But just after lunch, as I was about to set off to catch the bus into town, the phone rang. They had staffing problems at the bureau, could I re-arrange for next week. Sure I could.
But I had missed the chance to ‘dress’, I was disappointed. I got the impression that Uncle Jack was too
“Timothy. that sorting out you did yesterday, we’ll take Jean’s stuff to the charity shop tomorrow morning. But you forgot something, well, I didn’t tell you, in the bottom drawer of the dresser by the window there is more. That needs looking at too. I think you might get a bit of a surprise there”
I didn’t look that evening, it was getting late and a plan had begun to form in my mind.
5 – Friday
In the morning Uncle reminded me about sorting out the extra drawer of clothes, then grabbed his coat, his keys and his briefcase and was off. I cleared the breakfast things and then went up to the big bedroom, wondering what the ‘surprise’ was. And he was right. The drawer did contain yet more feminine things, and what things. Mainly underwear, but rather more exotic than Aunt Jean’s everyday stuff. Several coloured bra and panties sets, a basque, black and obviously intended to do a lot of figure-shaping, stockings, several pairs, in fact to a transvestite, wonderful stuff. But, to my great regret, no suitable shoes.
Then something Uncle had said the previous evening came into my mind. He had said he had found out about a specialist shop in town, one which dealt with transvestites and their special needs. He warned me it was more of a sex shop really, but he did think some of the things they had might be appropriate for me. So I caught the bus into town just after breakfast.
The shop was where he had thought, tucked away just off the main shopping street, and I must admit I did blush a little as soon as I walked in. There were indeed many weird items on sale there. But the clothing, and especially the shoes, thrilled me! After looking round for a few minutes, as a rather over-made-up assistant came over to ask if I wanted help, I declined her offer and left the shop – but only to go out and round the corner to the bank. I did have some money of my own, and this seemed a suitable moment to ‘invest it’ in finding out exactly what sort of life I wanted to have.
Over an hour later I left the shop having spent several hundred in one go, on about eight items. Well, in fact a lot more if you count them individually. After all a pair of breast-forms counts as two, three pairs of shoes is six, two packs of false fingernails is twenty really, fake eyelashes counts as two, three pairs of clip earrings is another six. And one skirt, though it is so short, so tight, so shiny, so black, so – leather – it should only really count as a half.
On the way back to the bus I called in at another store, emerging with yet more feminine luxuries, three pairs of black stockings, nail varnish of my own, lipstick, a few other items. I had decided to REALLY make a go of it, that afternoon indeed. A quick trip to a small supermarket followed, I was fairly laden down by now but I knew it was going to be worth it. I spent nearly half an hour sorting out things after I got home, arranging my purchases in my room, then setting out places for two in the dining room and preparing the good quality ‘ready meals’ I had bought so that ‘dinner a deux’ would be a simple but classy affair.
And so it was that, at precisely 1.30 pm, I set to it. I thought about trying to shave my arms and legs but decided against it. I took the quick way out, smearing myself all over with a depilatory cream and then showering it – and my albeit fine body hair – away. Then a very hot, very scented bubble bath, luxuriating in it for as long as I dare, just dreaming of feminine things and inhaling the gorgeous sweet-scented odour from the very expensive bath oils I had just purchased. As I towelled myself dry I appreciated for the first time in a long time the feeling of smooth skin almost all over my body. It was heavenly. Then I shaved my face again, very carefully indeed.
Undies. A pair of black silk thong panties, full at the front to cover what I wanted to be covered, pulled up very tight. I started to get excited but tried to calm down, breathe deeply, control myself, just get on with it. The breast-forms came next, I carefully followed the instructions for applying the adhesive and was delighted the colour was so close to my own skin tone. After lying down for more than the recommended five minutes I was delighted to feel their weight pulling down as I sat up. Me, for the first time, with breasts. The ‘cover-all make-up’ I had bought with it worked better than I had hoped, I could hardly see the edge when I merged it over the top of the forms and onto my own skin.
The basque came next, my skin was soft and smooth after my bath and, I hoped, ready for moulding. Indeed it was. After pulling the draw-strings as tight as I could I looped them over a door handle and put all my weight into pulling them even tighter. I could hardly breathe at first but, when I caught a quick glimpse of my shape in the big mirror, I knew it was worth it. Then I had to think about the sequence of what was to come next. The nails last, probably, they were rather long and I would have trouble dressing with them on. But my toenails, I could do them. I did, another first, spreading the creamy deep red liquid over all ten of them and enjoying every moment of the experience.
I was so excited – surely most women didn’t feel like this, dressing was almost an orgasm in itself. I calmed myself again and turned towards the rest of my makeup while my toes dried. I took my time, took care, this was to be as good a job as I could possibly carry out. A thin covering of a smooth foundation cream, it has a glorious silk sheen, I love it still. Just a little heavier down the sides of my nose and under my chin. Just a little blusher, not at all heavy, under my cheekbones.
I was very careful indeed with my make-up, being sure to produce crisp lines to my eye-liner end smooth silky lips. I resisted the temptation to inspect my face too closely at this stage, instead reaching for a hairbrush and smoothing my own hair straight back, then picked up the blonde wig. It fitted well, I reached round and clipped it into place, then revelled in gently brushing my very own golden locks. I had chosen big gold hoop earrings which I also clipped into place, then stood up. Time was getting on!
The basque had ‘settled’ onto me, and the uplift bra was now having its full effect, I looked down onto a very impressive bulging cleavage. But I had to get on, I unwrapped my new stockings, black, very sheer and seamed with a ‘Cuban heel’ effect. Sliding them onto my freshly smoothed legs, and clipping the six garters into place was an experience I will never forget. Then I did sit down again to attach my long red fingernails, not with sticky pads as I had done before but with the proper adhesive, I wanted no mishaps to spoil the evening. Three gold rings and one small gold bracelet completed the effect, my hands really did look much more delicate, more graceful, more feminine.
And finally, nearly, my top and skirt. The blouse was one of Aunt Jean’s, black, sheer, see-through over my arms and with six gold buttons down the front. I undid the top three and clipped into place, difficult with those nails on, a black velvet choker with a single matching stud at the front. And then the skirt, I had hardly dared buy it but I couldn’t resist the temptation. I slid it up my legs, over my thighs and into place, straining a little to pull up the zip and fix the little clasp at the top. And then a wide gold belt round my waist.
My shoes! The skirt had excited me, those shoes totally thrilled every bone in my body. I had fallen in love with them in the TV shop. I had bought two other pairs, one with much lower and more sensible heels. This pair were in no way ‘sensible’. Shiny black patent, with gold-coloured 6″ stiletto heels and ankle straps, each with a tiny gold clasp. I slipped them on, the feel of the nylon sliding in was exquisite, and they really did take some fastening, I was determined not to damage my long red nails. I stood up, my first time on such ultra-high heels, and walked around the room a little, marvelling at the way such heels made the muscles of my feet tense slightly and produce a pair of very effective, female-looking ankles. I felt as if I had been wearing them all my life, I loved it. And when I turned to look in the mirror, I gasped, the reflection I saw was absolutely everything I had hoped it would be – ‘sex on legs’!.
I grabbed my clutch bag, again black with a bright gold chain, and stuffed into it a few things from my coat pocket – a credit card for some reason, my own driving licence, a little money, then added my mascara and lipstick. I was ready.
In the kitchen I finished to last stages of sorting our evening meal, again revelling in those female sensations – walking about in very high heels, the tightness of my skirt as I stretched across the table. And some new ones to me, the feeling of the weight of my breasts as I leaned over, the slight awkwardness but nevertheless enjoyment as I tried to arrange the cutlery with my long red nails flashing in front of me.
It was getting a bit too much, I opened the French windows and stood on the patio for a while, it was just beginning to get dark. The cool air on my nylon-clad legs, another gorgeous feminine feeling. Breathe in, I thought, calm down.
I went back into the dining room and turned the light on over the table, then dimmed it slightly. I opened the wine and poured myself a glass. I heard a car drive up and then footsteps coming over the gravel up to the front door.
“Hi Timothy, where are you?”
I walked through the double doors from the dining room into the hall. In a voice I hoped would sound gentle, feminine, a little bit sultry and sexy, I spoke.
The voice had exactly the right effect, alerted Uncle Jack to the fact that something was a bit different. And the greeting too, I had always said ‘Uncle Jack’, almost always, before. Now I was being more familiar, there must be a reason for it. Uncle Jack had just put his briefcase on the hall table, had his back to me. He turned and looked, seeing me silhouetted against the light from the dining room. I strode forward, feeling my breasts bounce, I smiled.
“Streuth! Timothy. You look sensational!”
Uncle Jack always did know exactly the right thing to say. I strolled forward to take the newspaper from under his arm and lie it on top of the briefcase.
“Thank you, Jack” And I kissed him lightly on the cheek! “Dinner is almost ready, I wanted to try for something special this evening.”
Uncle Jack was still staring. I watched his eyes as they moved their focus from my face and hair, down over my nervously heaving breasts, past my tight waist and over my skirt to my nylon-covered thighs, then down my long legs to my stilettos. Then he looked up again.
“I can hardly believe it, you look gorgeous. And definitely not a ‘Timothy’. You need another name, in no way can I call you ‘Timothy’”.
I had to think. In my own mind, over the years I had adopted several female names.
“How about ‘Tina’?” asked Uncle Jack.
Perfect. I smiled.
“Yes, thanks, that will do very nicely indeed” . I took Jack’s arm and led him through into the dining room. “Hungry?” I asked as we approached the table.
“I could eat you, Tina” joked my Uncle.
As is often the case Uncle’s joke cleared the air, my nervousness faded, I was immediately more relaxed. Uncle held the chair for me, then sat opposite me. He was still staring.
“Really – er – Tina. You look gorgeous, no, I mean it. If I didn’t know I would definitely be attracted to such an attractive woman. And a good cook too!”
I was thrilled, and we began on our starter dish. The whole meal went so well, Uncle being very charming, paying me compliments, calling me ‘Tina’ all the way through, topping up my wine for me and so on. As we finished our coffee he stood up and held out his hand. I reached up to take it, and we strolled hand-in-hand into the lounge.
We just sat and talked for a while, me in an armchair, Uncle Jack on the sofa. After about half an hour he got up and disappeared into the kitchen, coming back with a bottle of what was obviously champagne in a small ice bucket, with two glasses. He must have prepared that when he went to the bathroom just after the meal.
“I thought we should celebrate your coming out, Tina”
He poured us two glasses and held mine out, I stood to take it.
“Right, let’s do this properly” he said, smiling, taking my arms and linking it to his so we were joined as we sipped the champagne.
We had already finished off the bottle of wine, I was just a little uncertain on my ultra-high heels. I felt his other hand grab my bum to steady me, and I giggled, sipping just a little more. His hand stayed in place and just began to slide up and down a little. His breathing was becoming heavier.
“Jack, you remember you said ‘Go for it’ if there is something you want to do. Well, what if someone else is involved, if you think they will approve but if you are not totally sure?”
“Well, Tina, if you think they will approve, then the same applies. You have to be ready to say sorry if you are wrong, but…”
I didn’t let him finish.
I reached across to him and with my arms round his neck I gently pulled him towards me. It was obvious I was going to kiss him. I looked for any signs of repulsion in his eyes and saw none. Our lips touched very briefly. I backed off.
“Do I need to say sorry?” I asked, looking intently into his eyes again.
He didn’t answer, just stood there for a few moments. Then he grasped me firmly in his arms and kissed me again. His lips were soft and warm and extremely inviting, I began to move my mouth against his, to tease his lips, to push my tongue across them, as I did so I felt him respond. His hands moved across my back, he was grabbing my arse cheek again with his left hand, his right slid up to cup my breast.
We separated, both breathing heavily, but I think disturbed by events. I was still holding Uncle Jack’s hand.
“Uncle Jack, are you really sure about this? I think we may be getting into something…”
My voice trailed off as I noticed the rather glazed look in his eyes, then he ‘came to’.
“Timothy, I mean Tina, I’m not sure…”
Neither of us could express it. I picked up my champagne and sipped again, Uncle Jack followed suit. He sat down on the sofa and shuffled along, leaving room for me. I sat next to him and as I did so the hem of my skirt slid up to reveal my stocking tops, my garter strap, just a glimpse of bare thigh.
“Tina” gasped Jack as his hand slipped across my thigh and up inside my skirt “Christ, you are so hot, I have been horny all evening”.
This time I wasn’t hesitant, I grabbed the back of his head, my own lips rushed to meet his, we kissed long and hard and with passion this time, our lips playing with each other’s, our tongues exploring, our hands groping, Uncle Jack was leaning on top of me, his hand reaching inside my blouse and surrounding the bra cup of my basque.
And I was loving it! The warmth of his passion excited me, to think that I had done this to a man, that he found me, ‘Tina’, exciting and desirable. My own left hand slid inside his shirt, sliding across his back, feeling the tension, teasing at the hairiness there, digging my nails in. The kiss lasted and lasted – and then finished.
We separated. Maybe Jack was thinking, getting worried, wondering what all this really meant. But I wasn’t wondering, I knew. I had felt the swelling between his legs as we had groped each other’s body, and smiled at him, looking straight in his eyes, smiling. I leaned over and kissed him again. He ‘woke up’ again from his dreaming and stared hard into my eyes. Did he see Timothy there, or Tina?
Whichever, my course of action was clear to me, I had come this far, so much farther than I had intended or dreamed of, I had to see it through. I reached down between his legs, and at my red-tipped fingers and began to slowly slide them up and down.
“Er – Tina”. Jack had a slow smile spreading across his face. “That is fantastic. But – when we talked about this last week, you said you weren’t gay. Well ….”
I enjoyed his joke, last week I had been very uncertain about my own sexuality but now I knew. But then I realised something else.
“Well, Jack, my darling”. After that I just couldn’t call this man ‘Uncle Jack’. “What about you?”
“Me? I’m not gay.”
“You could have fooled me.”
“No, Tina. I’m a totally heterosexual male. Who is being fondled by a gorgeous sexy woman. At least that’s what I still see before me.” He grinned again.
I grinned too. I could see his point. I smiled and stood up.
“Do you really think I look sexy, Uncle?” I asked.
“Tina, you look absolutely gorgeous and if you carry on flaunting yourself to me like this I will not be responsible for the consequences”
Which is exactly what I wanted to hear. I snuggled up to him again and we kissed and cuddled , well, more than that, we groped and fondled each other for over half an hour. As we parted after one particularly steamy necking session we looked into each other’s eyes. And knew. This was indeed getting dangerous. I decided that would do for tonight and stood up, pulling my skirt down over my stocking tops and tucking my tits back into the cups of the basque once more.
“Well, darling, I’m going to bed.”
Which I then did. Back in my own room I reflected on the evening as I stripped and cleansed my face. I just didn’t undo the fake boobs, that was going to be too much bother, I would have to sort that out in the morning. I closed my eyes as soon as my head hit the pillow. I don’t think I dreamed, but I am sure I slept with a smile on my face.
6 – Saturday
Next morning I woke up early. With an enormous feeling of satisfaction. I cleaned up and showered and shaved well, then found the solvent for the adhesive for my breasts. Wouldn’t do to turn up at breakfast bulging like that.
But then I thought to myself – why not? OK, not in jeans and T-shirt, my usual Saturday morning attire. But I could dress again. And why not? On Saturdays I usually got up early and went out to the gym club for an hour’s workout. Uncle Jack had enrolled me in the second week of my visit, to give me the chance to keep myself fit and to give him the chance of a lie-in, without feeling guilty he was not providing for his ‘guest’. But I could give that a miss, of course I could.
Within two minutes I had scoured the wardrobe and my ‘female undies’ drawer and had my outfit spread out on the bed, ready. Why not indeed? I had restricted myself to evening times so far, maybe I could get away with it in the daytime too.
I sat at the dresser and, as carefully as the previous day, did my make-up, not quite so glamorously but still attractively, I thought. I used the other set of nails I had bought, scarlet but not so long this time. One of the other pairs of shoes too, I had decided, these were red, still with high-ish heels but not so high. I slid and clipped my wig on, adding a smaller pair of clip earrings, then put on my bra and panties, scarlet this time. This was to be a ‘red’ day, not a ‘black’ one. I decided to stick to stockings instead of tights, and clipped them onto my suspender belt. A white blouse, gold necklet, red miniskirt, my red stilettos, I was ready.
I crept down to the kitchen, Uncle was still sleeping, and made coffee, then carried two mugs upstairs and went into his bedroom. I put the mugs on the bedside table and sat on the bed. Uncle was disturbed a little, he stirred. I leaned over and kissed him on the lips.
“Good morning, darling, I’ve brought you some coffee.”
Jack sat up and looked at me. He sipped slowly.
“I stirred a few minutes ago – I wondered if last night was all a dream, but now I see it wasn’t. Does this indicate some sort of decision on your part – Tina – dressing first thing in the morning? You said you were only confident in evenings, not in full daylight.”
“Well, Jack my darling. I wanted to see the full effect. Please, be honest, tell me.”
I stood up and crossed the room to open the curtains, then turned to face him so that he got a good look.
“Tina, I can only confirm what I saw last night. The view from here is stunning. Really, I mean it, I see a woman, no more, no less. Definitely Tina, and no sign of Timothy whatsoever.”
He certainly knew how to flatter a ‘girl’. I crossed towards him, perhaps flaunting myself a little, sat on the bed beside him, and leaned over and kissed him briefly on the lips again.
“Thank you, Jack, that’s what I really needed to know.”
And as I moved my hand a little I encountered his leg through the bedclothes – and something else. I smiled. Before I had time to comment he spoke.
“Tina, don’t so that. Please. Not now. This may be the place but it is not the time. I need to get up and dressed, we have things to do today.”
I was puzzled, and perhaps it showed.
“Please, take your gorgeous legs downstairs, I need to shower and dress, I’ll be down in 15 minutes.”
Which he was. I had prepared, showing my feminine skills to the utmost, breakfast on the patio – juice, coffee and toast, and we sat in the morning sunshine, neither of us too sure about the consequences of the previous night’s activities. In fact Uncle Jack kept staring at by boobs and my legs, and occasionally muttering ‘fantastic’ or ‘gorgeous’ or something like that. It was at the same time flattering and very off-putting, and made serious conversation impossible. Eventually we cleared up and I got round to thinking, now that I was dressed, just how I was going to spend the day. The gym visit was obviously out of the question. Uncle, though, had decided for me.
“Right, Tina, let’s go, we have some serious shopping to do”
That floored me. Shopping? Well, of course it had to be done, I had often done the weekly shop on my way back from the gym. Whizzing round with a trolley, and then Uncle picked me up with the load afterwards. But today?
“Yes. Look, Tina, I keep telling you that you look good. You look the part. Apart from staring at your legs nobody will notice that you are not what you seem. Believe me, I wouldn’t suggest it otherwise. I can’t afford to be seen out with a man who is dressed like a woman, can I? Not with my position in this town. So come on, find a jacket, I’ll get the car out.”
I dashed upstairs and found a cream-coloured blazer style jacket, hoping it was not ‘special’ to Jack as far as Aunt Jean was concerned. Then, before going, I had to visit the bathroom, not as easy as it sounds when wearing a tight basque. I resolved to find, if I was in any way going to continue with this, a different style of under-garment to help control my figure while still allowing access when necessary.
Jack was sitting in the car when I got outside, I loved the thrill of sliding my bum onto his leather car seats and showing him my legs. He got the point, came up with an appreciative grunt as I struggled to fit the seat belt strap over my boobs.
“You never had that problem before, did you?” he joked.
I was worried at first about going round the supermarket with him. Though I wasn’t well known in the area I had been to the local store several times. Someone there just might recognise me, or at least recognise Uncle Jack and put two and two together. But at the end of the street he turned left instead of right.
“I thought we should perhaps go somewhere different, how about that shopping complex just up the motorway?” he asked, obviously the same thought had occurred to him. “We’ll get the ordinary shopping first and dump it in the car, then maybe have lunch and have a look in some of the other stores.”
“OK, Jack, if all goes well that is”
And it did.
I felt strange at first and very nervous indeed, I kept thinking someone in the store would ‘spot’ something was wrong and make a scene. But no-one did! And after only a few minutes I felt wonderful, strolling round the supermarket with my ‘boyfriend’, just doing shopping like any other couple. At the checkout I was a little hesitant, Jack did all the loading while I waited with my purse in hand. We really didn’t have anything special, just ordinary things, except I had insisted to Jack that he let me buy myself some new stockings. I wanted several pairs but he insisted on only one pair, saying that I would ‘get another chance later’.
After loading the stuff into the car Jack drove us back home again and I did my ‘wifely’ job of putting things where they belonged in the kitchen. Then he arrived at the door again carrying my jacket, insisting that we were going out again. That first ‘proper’ outing, when I associated with several other people, one of the shelf-stackers in the supermarket, the boy on the checkout, the guy collecting the trolleys in the car park, had done me the world of good in confidence terms. Nobody had given any indication at all that they didn’t see me as I wanted to be seen, as a woman.
As Jack held the car door open for me to get out a few minutes later, I couldn’t help it – I just smiled at him and kissed him yet again, there, in broad daylight, in public, in the café car park, I really was having a wonderful day. I took his hand as we walked into the café. We only had a slight snack but it was still fun, being treated as a woman, and on one occasion being addressed as ‘Miss’.
And after all that, just when I was thinking we had done it all, Jack surprised me again. Instead of turning left out of the car park to head back home he turned right. I looked across at him, puzzled.
“More surprises in store, my darling” he said – the first time he had addressed me in that way.
And to back up the greeting, after changing gear, he put his hand on my knee and slid it up my thigh, under my skirt. I slapped his hand playfully and scowled at him.
“Not now my lovely.”
A few minutes later we were pulling into yet another car park, in the shopping arcade at the other side of town, not one I had visited often. Again he took my hand as we strolled towards the shops. And he dragged me, well, escorted me really, straight into ‘M’elle’ – a rather swish ladies clothes shop! Before I could say anything he had summoned one of the assistants.
“Good afternoon sir, miss, can I help you?”
I realised straight away that she had checked straight away – noticed that I had no ring. I looked at Jack, hoping he wasn’t going to expect me to reply but it became clear he had everything in hand.
“Yes, I rang on Thursday afternoon, to discuss a dress for my friend here. I got a message yesterday that you had some success…..”
Thursday afternoon? That was before our session last night, what had Jack been thinking of? But now was not the time to ask him.
“If you will come with me miss, I can show you, we have two possibilities, size 12 isn’t it?”
“Er – yes” I muttered, then hung back to whisper to Jack.
“What is going on here? What is this about two dresses?”
Jack spoke more loudly, so that the saleswoman could hear.
“It’s a surprise my darling, we’re having dinner tonight to celebrate. I thought a new dress would be in order.”
He had me flummoxed. And trapped, I had no alternative but to go along. When we reached the changing area Jack sat down on a chair and picked up a magazine. I obviously did have to go ahead, on my own. The woman held open a curtain for me, I went in front of her into the changing area. To be greeted by another woman coming out of a small curtained area and posing in front of a full-length mirror, wearing only a bra on her top half! As I followed the assistant the posing woman turned towards me.
“Tell me dear, the assistant says this isn’t too tight for me, but I think she’s just trying to make a sale. Is it? What do you think?”
What could I do? This woman was standing there in front of me, insisting I look at her boobs and her cleavage. I swallowed, tried to speak calmly.
“It looks fine to me”.
Which it did, she had a very impressive pair of tits and they were only inches from my face. I swallowed again, then gasped as she quickly and expertly reached behind her back to unhook the bra. It fell forward and her big boobs ballooned out – I was left facing two gorgeous breasts, big nipples standing out, I just had to look away and brush past her as she breathed in.
“OK, thanks” she called back to me as I walked into the cubicle next to hers. I heard her say “I’ll take it, then”, then managed to get my attention back to my own concerns.
When the assistant showed me the two dresses on hangers, my mind was made up instantly. The black one, it was gorgeous, a shiny black material, with small imitation gems stuck or sewn all over it, giving it a ‘night-with-stars’ appearance. I had to try it on but fortunately the assistant had to leave me to do so myself, she was called away. I stripped to my undies, managed to get it on with a little difficulty, it really was very tight, and satisfied myself with a look in the mirror that it was OK. Within only a few minutes I was back in the store holding it and smiling at Uncle Jack.
He paid for it, and of course I had to have a new co-ordinating handbag, and a pair of large pendant diamante earrings, and a black velvet choker with a single large central ‘stone’, and a pair of sheer black seamed stockings, I could have gone on but I didn’t want to make too much of a hole in Uncle’s card account. As we drove back home I kept thinking to myself… ‘I’ve got the shoes, now, what sort of make-up shall I wear, and what about my nails, and shall I try to style my hair… ‘
All girly thoughts, I realised, I was really getting into this big-time……
We spent the rest of the afternoon just hanging round at home, Uncle Jack making appreciative comments about my figure and so on, then in the early evening he announced that he wanted me to ‘dress’ for dinner. I took that to mean in the new dress so I kissed him lightly on the cheek and went upstairs.
In my bedroom I stripped, showered carefully so I didn’t disturb my breast-forms and their ‘make-up’, shaved twice and towelled myself dry. I looked across at the dress, hanging there invitingly. I was surprised – it took me much less time this time to completely redo my ‘look’. I did my basque as tightly as I could and slid my new sheer seamed stockings up my legs, enjoying the sensation as I stood up and felt the tension spread round my legs. I just about managed to squeeze into the dress. Then I sat down to redo my nails, this time choosing the extremely long pair I had bought earlier, and enjoying stoking the vibrant red nail varnish carefully onto them.
And then the eyes, I do so love doing my eye make-up. I used a mid-blue over the lids, shading to a mid-purple at the top, then to pink below my eyebrows. Then a thin, not too dark eyebrow pencil to give just a little accentuation to them. The eyelashes were new to me but I relished the thought. A thin smear of the adhesive along the edge, they were more awkward to fit than I had thought but I did it, got them firmly in just the right place. After waiting a few seconds for the adhesive to dry I stroked over them, and over my own upper lashes, thick mascara, good quality stuff, it produced long black lashes, gorgeously separated and curled. Careful application to my lower lashes too, the effect thrilled me. A deep blue eyeliner followed to complete the effect.
And finally after edging my mouth with a very thin line of deep purple lip-liner, my lipstick, the same bright red as my finger and toenails, thickly applied, this was supposedly ‘kissproof’! I smeared a thin coat of gloss over my lower lip and just a little to my upper, then looked across at the clock. It had seemed like about 3 hours but had taken less than one to complete my dressing. I put on the glamorous diamante earrings and clipped the choker behind my neck, again luxuriating in the feel of my long blonde hair tumbling to my shoulders as I shook my wig to ‘settle’ it.
Finally a diamante bracelet which had been Aunt Jean’s and a silver-coloured watch, and in all seven large and rather gaudy rings. I stood up and stepped into those shoes, my 6″ heel black patent stilettos, and grabbed my bag. I turned and looked in the long mirror. The skirt of the dress was so tight and so short I could almost see the tops of my stockings. And the neckline was so plunging I was revealing a very convincing pair of bulging boobs.
The effect was well worth the effort, or so I thought, I hoped Uncle Jack would like my ‘look’ too. I stepped carefully down the stairs in my ultra-high heels, and then strode confidently into the lounge. Where Uncle Jack was not alone, he was talking to another man!
Jack turned to face me and, while the other guy was staring at me, stepped across the room, took my hand and kissed me on the cheek. I was taken aback by both events.
“Doesn’t she look gorgeous, Sam” he said to the other man.
“Fantastic” he said – it was the only word I heard him say.
He picked up a box from the table beside him and left. I looked past him – the dining table was laid with silver cutlery, as I looked Jack lit one candle over the table, then turned the light down. It was just beginning to get dark, and with the gentle music I had just noticed coming from the stereo, it was a very romantic scene indeed. Jack reached out a hand, I took it gently.
“Tina, I just knew you would look sensational in that dress, and Sam thought so too, I could tell. You did such a good job with dinner the other night that I thought I would reciprocate.”
Then I realised, as I heard a van start up outside. Sam was the caterer, Uncle had bought in a gorgeous meal for the two of us. He looked across at me again.
“Don’t you dare kiss me again, Tina, I would not be at all responsible for anything which then happened. Let’s eat’.
I realised then – I was famished. I hadn’t eaten for hours. Over the meal, not enormous but very good quality, Uncle again kept paying me compliments, then at the end as he filled my wine glass again, came the big question.
“Well, Tina. You have certainly proved you can be totally a woman. So what happens to Timothy now?”
I didn’t know, I seriously didn’t know. I had SO MUCH fun dressing and being seen out as a woman, it seemed a very backward step to change back, to go back to trousers and shirt, flat shoes, just being an ordinary guy. While he was waiting for me to say something Uncle came round behind me and helped me from the chair, in an extremely gentlemanly fashion. We strolled hand-in-hand back into the lounge where he opened the champagne. Again we linked arms as we sipped from the delicate glasses.
I looked him straight in the eyes, trying to keep my expression neutral. I had been thinking about his question earlier, I knew it would come up sometime during the evening.
“Uncle…” I started to say, but couldn’t put my thoughts into words.
I took his hand and sat down on the sofa, pulled him down next to me. I took his left hand and placed it on my knee and looked t him again. He slid the hand up inside my dress. I felt it move over my stocking tops, slide across my bare leg and touch my silk panties. Without speaking his other hand cupped my bulging right breast. I leaned over and kissed him, hard and passionately. We separated.
“Uncle, you remember you said ‘go for it’?”
“Yes, Tina, and I meant every word of it”
“Uncle. Will you seduce me?”
“Tina, my darling, if you hadn’t asked, well, I am as hot as hell right now, I reckon I might have raped you before the night is over!”
As he smiled I leaned towards him to offer my most passionate kiss yet. Then he led me up to his own bedroom. As we entered I turned my back to him, inviting him to unzip my dress. This he did, snaking an arm round my waist and burying his lips in my neck as he fondled my boobs from behind. I allowed the dress to slip down, standing there, in front of my Uncle Jack, feeling like a wanton tart, my boobs thrusting upwards and outwards from my tight black basque, sheer black seamed nylons and massive heeled stilettos, my jewellery flashing in the light.
I felt fantastic, I felt promiscuous, I felt lustful.
“Now stand still, Jack my darling, I want to undress you”
And I did, undoing his tie, opening his shirt and sliding my nails through his slightly hairy chest, then unbuckling his trousers and helping him remove them, and his pants and shoes and socks. He stood up, naked. I saw for the first time in that situation a nude man, and wondered if I was in any way seeing him as a woman would. He struck me as rather ‘tall, dark and handsome’ – I thought for a moment. ‘I want to have sex with this man’.
His erect cock was standing proud and stiff, I teased it with my fingers, Jack started moaning a little, I had to kiss him again to quieten him as we tumbled onto the bed. Then he slowly begin to rub my left thigh, stroke my garter, feel the roundness of my arse. He began to kiss my legs, playfully running his finger and then his tongue along my panty line. I reached down and felt his throbbing cock.
I kissed it, then moved lower to his balls, as he arched his back to give my mouth access. I spent long minutes licking, sucking and kissing them, enjoying their swelling and the hairy feeling in my mouth. My tongue darted down and briefly sucked at his hole before returning to lick his long shaft. I sucked round the base of the shaft, making it glisten in the light. I moved on to the bulging head of his cock, flicking the tip with my tongue, playing with it. Quickly, I covered his whole shaft with my eager mouth.
Forcing the whole cock into my throat, I can still feel the firm head as it nearly gagged me as it slid down my open mouth. Slowly then with increasing speed I began to thrust my mouth up and down the shaft, sucking hard as I moved rhythmically. Jack was moaning loudly now, trying to hold back, I could feel his muscles tighten as the first pre- cum trickled out of the tip of his cock. He held my head in his hands, thrusting when I did, working with me, until with a final devastating eruption he climaxed, filling my mouth and throat with his hot cum.
He pulled out just before I began to choke, his thick cum was warm, and sticky and gorgeous. He eagerly kissed me, and our mouths and tongues mingled with his semen. I gulped and swallowed, feeling the heat as the fluid pulsed down my awaiting throat, sensing the warmth as it moved into my stomach. This was sensational!
Together, we rolled back and forth across the bed, the memory of Jack’s climax heightening the excitement of the moment. I relaxed briefly, then I could feel his hardness pushing at me again. He slowly moved on top of me, pushing down with his hips against my groin. My own cock was rock hard, straining against the lace of my panties.
Jack moved his hand down along my stomach and began to gently stroke my panties, pushing back on my shaft, teasing the head though the fabric as it rubbed across the very sensitive tip. I felt every delightful movement across the skin. He pulled my panties down a little further, his fingers probing into the hot chasm of my arse, digging at the hole of my anus. Then he pushed a finger into my arse.
I gasped as he rolled me over, his stiff wet rod square in my face. It was really erect again, I stroked his cock gently.
“Jack, you really are a very good lover you know.”
“And so are you, Tina, I’ve never known a woman like you.”
I felt great!! I took his glistening cock in my mouth again, and as I did so, it began to regain strength even more, growing larger with each squeeze of my lips, I just had to let it go. We shifted across the bed, our lips meeting passionately again.
As we parted Jack spoke.
“Timothy, this has gone way too far, this is serious, I am in absolute ecstasy right now, I am desperate to shoot my sperm up you. You never did really answer my question, where is all this leading?”