Posts Tagged ‘cross-dresser’

I have to admit, even as a married woman I absolutely LOVE going to our local gay/drag bar. Yes, being surrounded by women that are gay and bisexual is thrilling, but I will also admit that I find the “girls” in drag extremely exciting.

When I first went to the bar to watch the drag show I was amazed that lots of the “girls” looked better than I did.

In particular, there was a “girl” in an evening gown, long blonde wig, and surprisingly feminine features. I tipped her and while “she” sang she leaned forward, showing me that the cleavage I was looking at was just a trick of make-up and boning on the dress. However, I was surprised to look down the dress at one single pierced nipple sporting a small silver ring.

I do not know why, but that moment has always stuck in my head as extremely erotic!

That moment has evolved within my mind to a fantasy, as most erotic moments often do. I fantasize about buying her a drink and having the bar tender take it to her, him motioning in my direction and her lifting the glass to me with a sultry smile.

I wish to myself that I would have had the nerve to really talk to her that night, discover who she was, her sexual orientation, if dressing in drag was just fun or actually pleasurable. I know in actuality it would be different, but in my fantasies it plays out something like this!

Her show set is done and as we sit and talk, kicking back a couple drinks, relaxing a bit more than we should with the help of alcohol. I am pleasantly surprised to find that she is bisexual and her name, Ashley, is just as gender neutral as she is. She is single and doing the shows is fun for her, but she primarily lives her life as a man doing retail sales at a local cell phone store. I share that I am also bisexual, but married, a mother and about my life in general.

Our conversation is easy going and comfortable and there is a mutual attraction as friends and also a slight bit of sexual tension between us. The hour grows late and we exchange cell numbers and head our separate ways for the evening.

The next day Ashley texts my cell asking how I am, while I reply my husband inquires about who it is and I reply,

“Ashley. We met at the club last night?”

He tips me a look and says, “Gay or Bi?”


I reply back, purposely not mentioning that Ashley is actually a male in drag and letting my husband create his own fantasies.

Over the next few weeks Ashley and I text and talk often and get even closer. Together we plot getting together and share fantasies, confess secrets, and become good friends.

Knowing that my husband is assuming Ashley is a girl, I am not at all hesitant in asking if our kids can go spend the night with grandma and if Ashley can come over to hang out with us. As I expected, he is eager to oblige.

The night that Ashley is supposed to come over I am eager and tense. I have absolutely no clue how to dress, what to say, or whether she will be coming casual as a man, or dressed as a woman.

I don’t want to seem desperate and don’t want to go to the extreme of wearing a dress when we are just sitting at home, but I also don’t want to look scrubby! Finally in a fit of exasperation I throw on a pair of black jean shorts and a simple pink fitted tee-shirt, although I am sure to pair it with some cute silky thong panties and bra…just in case!

The doorbell rings and I have to restrain myself from leaping to the door. Upon pulling the door open I find that Ashley has indeed, come dressed as woman as I had hoped. She is wearing a shoulder length wavy strawberry blonde wig, her blue eyes are very bright in comparison, and her make-up is done light and natural.

It appears she has struggled with some of the same issues as me and has arrived in hip-hugging jeans and a red fitted tee-shirt. She has on a small padded bra, giving her the impression of a tall, yet thin and small breasted woman.

I tell her hello and give her a hug, introducing her to my husband. My husband smiles and tells her hello, but I am not stupid. I caught the look in his eyes and him checking out her ass as she puts her purse next to the love seat adjacent from us before she sits down. I am always aroused when I notice my husband checking out another girl, but I am even more aroused at the fact that he is technically checking out a GUY.

We are having fun, a nice laid back time, watching stand-up comedians on TV, sharing funny stories, and popping back a few drinks. I am keeping mine limited, because I do not want to get drunk. Although I did decide to make some jello shots for the occasion!

I announce that I am going to get some jello shots and ask who wants one, and we all agree we do. On my way passed Ashley to get them, she reaches out and smacks my ass, giving me a grin and making eye contact letting me know that she is planning on more.

Coming back from the kitchen, jello shots in hand, I decide to start getting things rolling on my own and have a seat next to Ashley on the love seat instead of back on the couch with my husband. We down our jello shots, daring each other and seeing who can swallow theirs the fastest and easiest.

She shots are taking effect; my head is starting to cloud, when I feel a hand on my knee. I look over at Ashley and she is slyly watching TV and rubbing her hand from my knee up my thigh and back down again, a slight smile on her face.

I look to my husband, who has obviously noticed, and he smiles at me and nods.

I move my hand to Ashley’s arm and start running my fingers up and down while she continues to rub my leg. My husband is watching and my lady parts are really starting to heat up.

Ashley moves toward me, sweeps my hair back and begins kissing my neck. I feel my breath suck in, and grab for her waist to pull her closer to me.

She drops to the floor and kneels between my parted legs, again running her hands up my thighs before sliding them up my shirt and cupping my breasts. She gives them a quick squeeze and then, much to my amazement, pulls her hands out of my shirt and stands up.

For a moment I am flabbergasted. I watch her stand up and think to myself that my mommy body must have turned her off. But she tips a wink at me, turns, and drops back to her knees in front of my husband. She begins to run her hands up his thighs up just like she did to me, paying special attention to a certain swelling that has recently started in my husband’s pants!

I curl my legs up under me and start to watch Ashley play with my husband. The voyeur that I am, I am relishing this immensely. My husband’s eyes are closed, his head leaned back, and he is enjoying Ashley fondling him.

She presses a hand on either side of my husband’s pants fly, bites the fabric between her teeth and pulls. There is a loud pop as they come unbuttoned, and she skillfully clenches the metal between her teeth and pulls the zipper down.

I notice her reach between her legs and back toward her ass and know that she must be uncomfortable trapped in those tiny jeans.

I unleash one leg from under me, open it wide and let it trail to the floor. I drop my hand between my parted legs and enjoy the heat. I will admit that there are times that I have major penis envy; however, I love the fact that I am the only one that really has a pussy in this situation!

Ashley releases my husband’s cock from his pants and slowly moves her hands up it. She turns and looks at me, making eye contact and giving me a quick wink before sinking her mouth over it. My husband sighs and reaches up to grab her hair, but she quickly grabs his wrists and presses them down.

It’s not often that hubs and I have group situations where he is being paid a lot of attention, so I am really glad to see how much is being given to him. I move to the floor so I can get a closer view, stealing a quick grab between Ashley’s thighs and feeling something not very feminine growing down there!

I grab a seat next to my husband so I can watch Ashley give him head from a better point of view. My god, she looks beautiful down there, just sucking away. She grabs onto the sides of my husband’s pants, he leans up and she drags them down, leaving my husband naked from the waist down.

He isn’t near orgasm yet, but his balls are tightening, showing me orgasm is approaching. However, Ashley can tell what is going on and she turns her focus to me.

“Are you going to take those off?”

she asks in her husky voice, motioning toward my own shorts.

A moment of tension and panic sets in for a second, as it always does when I have to expose my cootchi with my giant thick labia. I have yet to have sex with a girl built like me in the lower region, and I think that MOST people have not been with a girl like me, therefore I get nervous about it and how people will handle my appearance or if they would be able even figure out how to START pleasuring me.

I stand up, slowly unbuttoning my shorts and sliding them down my thighs. I let them fall to my feet, kick them off and start to sit down again.

“Huh-uh.” Ashley says, “panties too.”

I stand motionless for a moment. Not sure what to do. But I note that while she looks at me she has slowed down playing with my husband’s cock and that simply will not do. So I slid my little lacey panties down too and stand for moment, naked from the waist down, not sure what comes next.

Ashley grabs my hand and pulls me over, stands me in front of my husband so he is looking at my ass and presses her hands between my legs and forces them open.

She must have seen the look of panic on my face, because she gives my puffed up pussy a kiss, looks at me and says,

“Don’t worry, baby. I promise I will be nice.”

At which point she pushes me back, landing my ass on my husband’s stomach. She drops back to sucking on my husband again, and from this point of view it’s almost like I have a penis of my own she is sucking on. I can see her staring at my pussy folds as she slurps on him and I’m really just not sure what to do!

I sit for a few minutes watching her slurp away, and then reach down and slide my fingers across my bulging labia. She lets me open my lips up for her, but as soon as I run my fingers up to my clit she smacks my hands away.

She moves up from my husband’s dick and kisses my cunt. Licking her way up and down my lips while stroking at my husband’s spit covered pole. Finally she settles herself at my clit and licks lightly. Just enough for me to breathe deep and open my legs a little more.

She surprises both my husband and I by gripping his member, and pressing it to my opening. Hub’s has been played with for quite a while now, and he is eager to press himself into my pussy.

He goes to work, lifting his hips up and down, I am on my tip-toes with my legs apart, and Ashley eagerly leans down and moves back and forth between sucking on my clit and licking at my husband’s sack.

I relax and try to enjoy her tongue. My head buzzing from the jello shots, my husband panting behind me. But he gets my pussy all the time. I know he wants something more, and Ashley knows it too.

I rise from my husband and Ashley and I begin to kiss. She peels her own shirt off over her head and I see that she has used her clever use of make-up to create cleavage again as well and using the padded bra. She peels my shirt off over my head and quickly undoes my bra. I’m now the only one nude. I look around, feeling embarrassed and excited at the same time.

My husband is watching us and slowly stroking at himself, knowing that he has neared orgasm a couple times, but he isn’t ready to blow his load yet. I can tell by the way that he is looking at Ashley that he is hoping she will be the one to produce it for him.

She lays me back on the floor, her ass in the air facing my husband, and goes back to sucking at my clit. Holy lord she is good at it! I have only ever had my husband and my old female room-mate bring me to orgasm orally, but Ashley is well on her way!

I watch my husband carefully through slitted eyes, admiring Ashley’s ass, tugging at his cock. He eagerly leans toward Ashley, reaching around and unzipping her fly and pulling her jeans down her thighs.

I see that Ashley is wearing a thong, which drives my husband crazy, and she quickly reaches down and grabs her penis, pulling it forward and squeezing her thighs together, leaving my husband to look at a smooth and very feminine ass.

Ashley leans up from my pussy, looking me deep in the eyes. I look down and see her cock peeking out from the top of the thong. I can’t believe that I am laying here doing this. One of my biggest fantasies come true!

But an unspoken question passes between our gaze.

“How is your husband going to react?” her eyes say to me.

“I don’t know.” My eyes say back.

My husband spreads apart Ashley’s ass cheeks and begins flicking his tongue at her asshole. She sighs and I see her penis twitch. I am dying to reach down and stroke it in my hands, but I don’t want to give it away to my husband just yet what is really going on.

I wriggle out from under Ashley and move to sit next to my husband so I can roll his penis around in my hands while he eats Ashley’s ass. Ashley presses herself down on her forearms, letting her hairless ass cheeks open farther, but being sure that she keeps her thighs pressed tightly together.

I can tell the moment of truth is quickly approaching. We won’t be able to keep this a secret much longer.

“Do you want me?” Ashley breaths to my husband.

“Uh-huh.” He says back while still licking at her ass.

“Even if I’m built a little different?” She asks between gasps as my husband licks away.

“I don’t care.”

He pulls his mouth away from her ass and begins massaging her cheeks.

“My wife worries all the time about how she is built different, and it has never bothered me any.”

With that, Ashley rolls over. My husband is so eager that he grips her panties and pulls them down, not noticing the bulge in them until after they are off. He stops pulling them off halfway down her thighs, staring at the small erect penis in front of him.

Ashley’s penis isn’t even close in size to my husband’s. She is about 5 inches and thinner than him. However, a cock is a cock, even if it is attached to a very hot “woman”.

Ashley looks at me with a little bit of fear. My husband is a very large man at 6’2 and 250. If he gets angry, he could really hurt her. I look to my husband and he looks back to me in shock.

“What?” he asks in disbelief.

“Please?” I say softly, meaning so many things with that little word.

He looks back at the penis in front of him, pulls the panties off the rest of the way and stops for a second. I can see that Ashley’s penis is starting to wilt and she begins to stand up, seeing that the night is likely done and my hubs is just not having this, no matter how feminine she looks.

She rises to her feet and begins to turn away, her penis only half erect and hanging.

“Wait,” my husband says, grabbing her hips.

He turns her back toward him, him sitting on the floor, her standing with her penis only a foot away from his face.

He looks back to me, looks up at her, looks over her body, and then surprises us all by taking her shrunken penis into his mouth.

My jaw drops. My pussy tightens. Ashley’s ass clenches and her head leans back. I watch in utter amazement as my husband gulps her penis deep into his mouth and begins to suck. I can see that Ashley’s erection is quickly returning and my already wet pussy is becoming even wetter.

My husband sucks, gulps, and pulls his mouth across Ashley’s shaft and I can see Ashley’s small balls tightening with pleasure.

“Slow down there big boy,” She says calmly, “Do you want to fuck me?”

I can see a million questions racing through my husband’s mind. He looks back to me again while I’m spread out, gently fingering at my twat, and then grips Ashley’s ass and growls,


Ashley quickly drops to the floor, gets on her hands and knees and sticks her ass out for my husband. I want a close up view of this! I leap down to the floor with them, land some wet sloppy kisses across Ashley’s ass, and then make sure I give my husband a few deep, wet sucks to get his cock fully hard and nicely lubed up.

He leans forward and presses himself against Ashley’s hole, rubbing his cock head against it a little bit before starting to press. I watch my husband slowly sink his shaft in and feel my pussy positively throb.

I watch my husband pick up the pace, grunting and clinging to Ashley’s ass. I can see Ashley’s hard penis wavering underneath her and lick my lips, falling to the ground and I shimmy myself under her and take it into my mouth.

I’m lying on my back, cock in mouth, looking up at my husband sliding himself in and out of Ashley’s ass when I feel a warm wet tongue caress my clit. I look down and see Ashley, licking at me when she can between strokes, her face pinched with pleasure.

I reach down and begin to play with myself while I suck and watch my husband pump away. I don’t want Ashley thinking about me. I want her to focus on her own pleasure right now.

I pump a couple fingers in to get them good and wet before rubbing furiously at my hardened pearl. It is hard, swollen and very eager to be played with. It’s almost like I am sporting a small penis of my own!

I take my hood and peel it forward and back over my clit, feeling the familiar burn in my thighs and tightening in my pussy of my orgasm nearing. I can see my husband’s tight balls and can feel Ashley twitching in my mouth. The only question is going to be who will cum first.

I feel Ashley harden even more in my mouth and know that it is going to be her and take a certain pride and pleasure in how much she is enjoying herself. I can feel her hot breath against my pussy lips, panting as she nears orgasm, suddenly she nearly falls, letting out a very feminine scream and she releases a hot load across my awaiting tongue.

The pulsing in her ass must have been intense; because I see my husband’s balls practically disappear into him and he loudly grunts as he shoots his own hot load into her ass.

I’m the only one left. I press my fingers into my snatch once again, giving a few quick, hard, pulls at my g-spot, getting my fingers really good and wet before going to work massaging my clit again.

The orgasm washes over me, very suddenly, and extremely intense. It seems that every pulse is an orgasm all of its own. I let myself scream and let my body contract and wriggle across the living room floor.

I finish, panting and looking up at my husband and Ashley, both of them sitting with their now soft penises lying against their thighs and grin sheepishly up at them.

“You two are too yummy.” Ashley says, gathering up her clothes and getting dressed.

“I hope you will let me come over again sometime?”

“Absolutely!” I call out, not even giving my husband a chance to answer.

He looks at me, showing that a million thoughts are racing through his head. But only one is going through mine. Will he let Ashley fuck HIM next time?

After seven long years of sitting around, questioning my sexuality and fantasizing over the one thing I thought I could never have, I finally decided it was time to make a move. I was going to experiment with my sexuality, I was going to look for a real live hot tranny to meet up with and have sex with and hopefully I would enjoy it as much as I had always fantasized I would.

I had been interested in transsexuals since I was in high school, when a freak encounter with one of the computers led me to catch sight of something I did not expect to see. The computers were shared with every class that came into the room throughout the course of the day, and apparently, whoever had used my computer in the class before me had decided it would be funny to leave a picture of a very hot and very well endowed transsexual as the back-round on the computer. I scrambled to find a way to remove it, but could not figure out how to do it at all. I called on the teacher to help but he surprisingly had no idea how to do it either, go figure the teacher does not even know how to work the computers in his own classroom. I was forced to try and ignore this picture and just carry on with my work, I did the best I could but by the time I got home the image had been engraved into my mind and I spent the entire weekend thinking about it.

It eventually began driving me insane trying to figure out what it meant that a picture like that turned me on and I found myself searching up more images and films on the internet that involved these beautiful creatures known to the porn industry as she-males.

The first question that came to my head; was I gay,

I did not know because honestly I still liked girls, in fact at the time I had a beautiful girlfriend who I had been dating for quite some time and hooking up with her was still just as fun as it had been before all of this had begun. After quite some time of struggling with it I decided, it was best to keep this a complete secret and do my best to treat it as if it did not even exist…I tried but it was, easier said than done.

By the time, I was 18 I was convinced that this had to mean something; the thoughts had not gone away at all, and I was really becoming more and more anxious to experiment. I wanted to see what it felt like to be one of those guys’ in the pics or movies being dominated by a hot woman with a big fat cock between her legs; I wanted to know what it felt like to be on the receiving end, to see it in real life and also to experience it for myself.

So here I was, 22-years old ready to finally go ahead and see what was out there in the she-male scene. My two best bets were either a gay club that was transsexual friendly or the City paper, although being unemployed and broke both of those options seemed a little pricey. There was a third option of course that I had not considered until it dawned on me at the last minute; craigslist. I typed in the website name in my browser and went straight to the casual encounters section and after twenty minutes of scanning through different adds with pictures included in some, I stumbled upon’ the perfect match for me. Her name was Karlie and she was absolutely, beautiful, with long silky red hair, beautiful blue eyes an incredible body and a pretty, large cock too judging by the picture she had added with the post. She was 25-years old a couple years older than I was, and according to the add, she was simply looking for a night of good sexual fun no strings attached and no need for either of them to pay the other.

I immediately responded to the add sending a picture of myself, I was a bit too nervous to take one of myself in the nude so I just took one of myself without a shirt showing off my upper portion of my body and asked her to reply if she was interested at all.

To my surprise’ she did indeed reply; she said that she thought I was hot from what she could tell and that she was very interested in me. I did not expect her to ask for a few more photos though until she asked that I send one of myself completely naked as well as a shot of my asshole as she apparently preferred to top during sex. That was fine with me, all the porn I watched usually involved the man bending over and getting, plowed in the ass by the she-male and this was what I was looking for mostly. I did as she requested and sent the photos to her and about half an hour later, she replied again telling me that she was more than interested and that she wanted to meet up as soon as possible.

We exchanged phone numbers, and I called her and we began discussing our plans to meet up and have fun together. She did not live very far from me and I still lived at home with my parents so I did not exactly want her to come to my house; we agreed that I would meet her at her apartment, which was probably only about a 20, minute ride by bus or car. I got on the bus and found that it was less time than I thought to get to her apartment and found her waiting outside on the front step. She was even more beautiful in person than she appeared in the picture she had posted on craigslist.

“You must be Tom?” she asked with a smile on her face.

“That’s me; and your Karlie?” I asked shaking her hand. She leaned in and gave me a hug before leading me through the front door and up the stairs to her apartment, which seemed to be a pretty, nice place really. “Can I get you a beer?” Karlie asked me. “Uh, sure…do you have Coors light?”

She went to the kitchen and returned a moment later with a bottle of Coors Light and I twisted the cap off and took a long swig of it. I was a little too obvious about how nervous I was but Karlie did not seem to mind as she took a seat right beside me on the couch and smiled at me the whole time. “So I’m glad to meet you; you’re really cute you know that?” she asked seductively as she began running her hand up and down my leg and I smiled trying to relax a little bit. “I can tell how nervous you are, so I’m assuming this is your first time. There’s nothing to be nervous about, I love first timers and I’m always extra careful when I know I’m with someone whose’ never done it before.”

I smiled feeling a little relieved to know that, “Thanks; I’m glad to hear that.” I said feeling a little more calm than I had before.

“So shall we get started?” she asked me and I simply smiled nervously and nodded my head, “Okay then.” She said before leaning’ in towards me, It all happened so fast and before I knew it her beautiful red lipstick lips were pressing against my firmly and her tongue slid into my mouth.

She tasted like strawberries and immediately I felt my cock begin to react to her touch as she ran a hand up and down my left arm. Our kissing became more passionate and soon enough we had made our way into her bedroom, she pulled my shirt off over my head and tossed it to the floor and seconds later she fumbled with my belt, undoing it and pulling my pants off.

Once she had gotten me completely undressed she began undressing herself and as she removed her clothing piece by piece, I felt my cock growing harder and harder. It was becoming increasingly difficult to resist the urge to jump her and fuck the hell out of her right here right now, but she wasted no time after she removed her jeans dropping to her legs and wrapping her warm wet lips around my hard cock. I moaned as she began sucking my cock like an expert, stroking it and playing with my balls at the same time; then she reached up running her hands up my stomach and chest to tweak my nipples and squeeze them lightly. I moaned again as I felt myself growing closer and closer to my orgasm when she stopped and stood up to kiss me again, teasing me by not finishing what she had started.

She broke the kiss and smiling at me seductively, she gave me a light shove and I fell backwards landing on her bed. She climbed on top of me and after a few moments of making out and her licking, sucking and biting at my neck and my nipples, she turned around so that now her ass was in my face and her huge cock was dangling just in front of my mouth. I inhaled the musky aroma of her ass and balls as she once again wrapped her lips firmly around my own cock and I had nothing better to do than lean up and wrap my lips around her cock; for the first time ever I was tasting cock and I had to admit it actually did not taste half bad. Here I was, in bed with a hot she-male in 69 with her sucking my cock while her ass and balls were, shoved in my face it was a dream come true for me.

After just a minute and a half, I felt my cock begin to throb in her mouth and I tensed up a little as she slipped a finger into my tight virgin asshole and started teasing my prostate while continuing to suck my cock.

Finally, with a grunt I exploded, shooting a massive load of cum into her mouth and Karlie swallowed every drop without any difficulties at all. I groaned, still sucking her cock as my orgasm began to subside and she released my cock still fingering my asshole as I sucked her off. By now, she had inserted a second finger into my ass and was spreading me wide open, I grunted in a mixture of discomfort and pleasure as my cock slowly turned hard again.

“You like that baby?” she asked seductively and I could do nothing but moan my approval and she giggled. “How about this?” she asked as she slowly and carefully slipped a third finger into my ass. I groaned, and grunted and writhed in pleasure and pain as she stretched my asshole wide open before sliding off, of me, her cock slipping out from between my lips as she got between my legs. She reached over to her nightstand and pulled out a bottle of lube and a single latex condom, tearing open the wrapper and pulling the condom out handing it off to me. “Hold this for a moment,” she said as she started lubing up my asshole nice and good, making sure that it was just wet enough for her to slide into me without causing too much discomfort. Once she felt I was ready, she took the condom from me and smiled as she began unrolling it over her huge fat cock, then applied a bit of extra lube to her cock.

“Ready?” she asked me, “Yeah, whenever you are; just go easy on me.” I said smiling as she pressed the head of her shaft against my asshole. She leaned in and kissed me on the lips probing my ass gently with her cock, I groaned at the feeling as she applied just a little bit of pressure and she popped right into me. I grunted in pain as a burning hot sensation ripped through my asshole and she began carefully easing herself all the way into me until she was, buried all the way up to the balls in my hot tight ass. It was anything but pleasurable at first but after a few minutes of her slowly thrusting in and out of me, warming me up, the pain began to subside and slowly it started to feel pretty, good.

Once she was sure I had adjusted to the feeling of her huge cock in my ass, she started to move a little faster fucking my ass with a little more force behind her thrusts. I was in missionary position with my legs wrapped around her and the sound of her balls smacking my ass echoed through her bedroom along with the sounds of our soft moans and grunts, and soon enough she was plowing my ass, slamming in and out of me, both of us moaning quite loudly.

I dug at her back groaning in pleasure as she pushed deeper into me now pulling me closer to her and really pounding away at my ass now. She pulled out all the way at one point and I was left with a feeling of emptiness, but it only lasted a moment before she plunged all the way back into me and my entire body gave a jolt; she repeated the same move, pulling all the way out first and then slamming straight back into me again. She continued this same action for about a minute until my asshole began clenching and spasming around her hard cock, and she knew I was getting close to my orgasm. My entire body was shaking now and we were both sweating as she started fucking the living hell out of me, the bed shaking underneath of us and finally I gripped the bed sheets and screamed, my asshole clenching around her cock and my entire body went into a spasm. It was the most incredible feeling I had ever experienced in my life and I never wanted it to end, but unfortunately it did not last more than a few seconds before my cock spewed cum all over the place and the orgasm slowly began to subside.

Once my orgasm had come to a stop, Karlie started fucking me long and hard again before grunting, she leaned in close biting her lip as her own cock started to throb inside of my asshole. She exploded and bit her lip hard as she started to cum deep inside my asshole, her condom holding her semen back as she moaned and kissed me passionately on the lips.

After a few moments, she caught her breath and shakily pulled out of my ass, my legs fell to the bed and she collapsed beside me, both of us exhausted.

That was it; my first time with a she-male, and it had been just about everything I had ever thought it would be, and so much more too.

She lay’ her head on my chest and traced circles with her fingers over my chest for a few moments before glancing at the clock.

“It’s getting kind of late,” she said softly kissing me on the neck, “You can stay the night if you want too,” she suggested. I thought it over for a moment or two then smiled and kissed her on the lips, “If it’s okay with you then yeah sure.” I replied.

She smiled and moved closer to me, pulling the blankets a little to cover us completely and warm us both up. It did not take very long before we had both fallen asleep, and I dreamed about more unbelievably fun sex with my beautiful new transsexual friend. We would have many more fun encounters ahead of us.

James heard the doorbell go, and opened it to find his neighbour standing there with a smile.

“Hi James, I’m wondering if I could ask a favour? My broadband’s down and I have some urgent emails to send. Would I be able to use your computer for half an hour?”

“Sure Dave, come on in and I can help you out!”

Dave grinned at him as he squeezed past. James had had a crush on his hunky older neighbour forever. Everything about him was delicious, and he thought he’d even caught Dave watching James getting dressing up in his bedroom; when she peered out the window, she’d noticed movement from his room, but the lights had been out so he could never be sure. Dave had never mentioned it anyway. At the time, James had wondered if Dave was getting off, watching him pose in lingerie. The thought had turned James on so much that he nearly cum in his panties, and since then, he’d always made sure his curtains were open, just in case!

As Dave headed towards the lounge, James stopped to get a good look at his sexy arse; he was just about to follow his neighbour into the lounge when his brother Paul appeared.

“I’ll help Dave out James. I’ve a few things to chat to him about anyway; I need to sort out some things before I start my internship at the bank.”

James didn’t even bother arguing; Paul always got his way. He was only a year older, but had been the dominant one for as long as James could remember. They’d never gotten along very well, and Paul seemed to enjoy being a prick to him. James watched them both go into the living room before he headed back upstairs; for a second he considered having a wank thinking about his sexy older neighbour, but instead decided to plan his outfit for the weekend. He dug through his drawer, looking for his favourite lacy panties, before realising he had left them in the drier downstairs.


He’d have to be quiet. His family knew he was gay, but the cross-dressing was still his secret. And he’d prefer if the way they found out wasn’t with his brother finding him with a handful of lingerie!

He creeped downstairs and tiptoed past the lounge, trying to get into the kitchen as quietly as possible. As he was stealthily opening the kitchen door, the lounge door eased open a crack and he heard some very strange noises emanating from within. Feeling brave, James poked his head around the door and saw something that took his breath away!

Dave was sitting across from the door, completely naked and completely focussed on her brother. Paul, on the other hand, still had a T-shirt on, but was naked from the waist down, and his rock hard dick was evident as he slowly eased his lips down Dave’s cock. James was shocked; he hadn’t known either of them liked cock, and hadn’t even guessed both of them would be so well hung. Paul was slowly stroking his dick as he sucked, and it looked to James like it was about eight inches long. He’d never had one that big! Dave was even longer but not as fat, and a pang of jealousy swept through James as she watched her brother swirl his tongue around Daves purple bellend. It looked delicious! James realised he was as hard as both of them as he watched them play, and quietly rubbed himself through his jeans as he watched.

“Fuck Paul that’s it…..go nice and slow…..I want this to last,” Dave moaned from his chair, “Its been weeks since I’ve had you to myself…..I’ve been dreaming about your mouth.”

Paul slowly eased the long hard cock from his mouth, and smiled as he began kissing up Dave’s muscular body; soon he was leaning over Dave, still grinning as he moved in to kiss him softly. James got even harder as he saw their cocks rubbing together. He’d never looked properly at his brother before, but he was almost as tasty as Dave. They were both nicely muscular, and the sight of the two big dicks sliding against each other made him weak at the knees!

“I want this to last forever Dave” Paul whispered between kisses “I want to make you cum again and again… just need to stay quiet… my brother doesn’t interrupt us.” James watched as Paul reached for Daves gorgeous dick, his fingers wrapped around his length and squeezing softly as he kissed back down Daves hairy chest, stopping to suck on each nipple as Dave groaned softly.

“Mmmmm that’s a dirty idea, two brothers at once! You never know, he might be up for it?”

“I bet he would. I’ve heard him get fucked. But its not something you can ask your own brother is it?” Paul grinned before trailing his tongue down Daves toned stomach.

James nearly exploded listening to them; he was harder than he’d ever been, and it sounded like they wouldn’t have any problem with him joining in. He didn’t even need to think about it; he just hoped Paul was going to take his time like he promised; James needed time to get ready!.

He sneaked back upstairs and got dressed as quickly as he could. Being a closet crossdresser, he’d already had a lot of practice with changing in a rush, and James put it to good use. He was all dressed up in minutes, and put some finishing touched to his make-up before giving himself a final once-over in the mirror. James crept softly back downstairs, trusting the carpet to muffle his heels, and got back to the door to check he wasn’t too late. He was in luck, Dave was still moaning softly with his fingers running through Pauls hair. He was leaning back on the sofa, with Paul still kneeling between his legs. Her brother was completely naked now, eyes closed in pleasure as he bobbed on Dave’s fat cock. Perfect!

James slipped around the door and caught Dave’s attention, watching as his eyes widened in surprise. She grinned at the sight, and raised a finger at his painted lips to make sure Dave kept quiet. James moved carefully across the room, thankful for the carpet still muting the click of her heels. He relished Daves look of lust, and put an extra swing in her hips as she moved towards him, making sure her brother still hadn’t noticed her before she leaned over to nuzzle Daves ear.

“Hi Dave, I’m Jen. And tonight I’m your plaything.” She whispered throatily before she kissed him again. As she pulled back from him, he took in the sexy little crossdresser that stood before him, smiling coyly. Jens tight blue dress barely covered her tiny pert bum, and gave him a fantastic view of her thighs above her lacy black stocking-tops. The stockings and her six inch black heels made her legs look sleek, slim and amazing. A mane of jet-black hair cascaded over her shoulders, and her eyes sparkled as she ran her tongue over her ruby lips.

Jen kept her eyes locked on Daves as she dropped to her knees beside her brother. She watched him work on Daves fat cock, his head bobbing softly with his lips wrapped tightly around his shaft. She was a little shocked that she’d gotten this far without her brother noticing, but at the same time, she knew that if she were in his place, Dave’s massive dick would have her full attention. Feeling bold, and as horny as she ever felt before, she leaned in slowly, trying not to disturb her brother until she got her lips on Daves wet shaft. Jen slowly kissed her way up his big dick as her brother sucked on the bellend, until finally their cheeks brushed together. Paul instantly jerked away, startled and staring open-mouthed as his cross-dressing brother kept her attention on Dave; her mouth worked upwards, planting soft kisses all over him until she reached the tip. With a grin, she ran her tongue slowly around his enormous purple bellend and listened to Dave moan in pleasure above them. As she wrapped her lips around the tip of his cock, Paul smiled and brushed her long hair back, getting a good view of her ruby lips slipping down to suck.

Jen shivered in delight as she felt her brothers fingers brush against her cheek. She was wrong earlier, she was more turned on than she’d ever been! Her brothers touch was like a spark of electricity, and Daves cock filling her mouth felt perfect. She eased her lips back and pulled the cock from her mouth, giving her big brother a sexy grin. He was staring at her with a look of pure lust in his eyes; making her feel like such a whore! She pursed her red lips and blew him a kiss before slowly licking Dave’s wet cock, tasting the mix of precum and spit her brother had left behind. Then, never breaking eye contact with her brother, she slipped her lips back over the fat dick in front of her, taking as much as she could inside her warm mouth. It felt amazing, and as she began to suck in earnest she felt Dave’s fingers wrap through her long hair, urging her on. Another shiver ran through her body as she felt Paul move beside her; he’d begun to work on Dave’s cock as well! Jen eased the long fat prick from her mouth and watched her brother cup Daves balls as his tongue worked around the base of his shaft.

“Jesus this is hot” Dave murmured in appreciation as Jens tongue went back to work. She swirled it around Daves bell-end again before she slowly worked downwards; she traced down his throbbing shaft, moving to meet her brother at the base. She wasn’t sure how he’d react, but Jen needed to find out. Within seconds, she was opposite him, with both their tongues working around Dave’s cock; the first touch was tentative, but it was like another electric shock for Jen; it felt so taboo and so hot! She waited for him to recoil, but instead her cock jumped under her dress as she felt Paul push back against her tongue before continuing to lick. After that, it felt natural; it felt perfect!! Each touch lasted a little longer than the one before, and soon they were kissing around his shaft. Jen moaned in ecstasy at his touch, and both of them slowly moved their mouths up his shaft, their lips still locked together. As they reached his bell-end, Jen felt her sexy brothers tongue run over her lips and push inside her mouth. For a second, Dave was forgotten, and Paul and Jen pulled away from him, lips locked together as she sucked on her brothers tongue.

“Fucking hell, this is the hottest thing I’ve ever seen!” Dave moaned from above them. “I knew I had one dirty cocksucker for a neighbour, I never realised I had two! Now all I need to know is which one of you wants me inside you?”

Jen pulled back from Paul with a smile, loving the taste of him on her lips. “I need it bro. I need a shag so bad. You want to watch me get fucked? Your little slutty sister got so turned on watching you suck; now she wants you to watch her get used. Is that OK?”

Paul moaned in approval and she grinned, kissing him again as Dave sat back on the couch. Jen stood up slowly and turned her gaze on Dave. His dick looked even bigger now, standing straight up for her and slick with their spit. She couldn’t wait any longer, and straddled him on the sofa! As she lowered herself onto his lap, she felt Dave’s hands on her, tugging her dress up over her hips as she wrapped her legs around his waist. She could feel his fat dick pressed between her ass-cheeks, and hoped her brother was enjoying the view of the big cock pressed up against her tiny black thong. Her long red nails ran down Dave’s chest before he pulled her against him, planting soft kisses on her ear and moving down to her red lips.

As she opened her mouth to suck on Dave’s tongue, she gasped in surprise. Pulling away from the kiss, she looked over her shoulder to see Paul on his knees, alternating his tongue between her arse and Daves cock. Both of them moaned in approval before Dave spread her cheeks wide. “Tongue fuck her Paul,” he groaned, “Get her nice and wet…..get us both ready…..I need to be inside her.”

“Oooooohhh fuck yes” Jen whimpered, burying her face in Daves neck. She’d never been rimmed before, and now it was her brother who was sliding his tongue around her arsehole. “I love that so much Paul…..don’t stop…..lick me…..lick me bro.” Her brother lapped harder as she urged him on, and Jen groaned in delight at the sensation. It felt unbelievable, she never wanted it to end! “Tongue my hole baby…..tongue your dirty sisters hole” she squealed as she squirmed against Dave, finding his mouth again and pushing her tongue inside. Her dream had always been a threesome, and this was the hottest one she could imagine!

Just as her brothers tongue was becoming too much to bear, he pulled away, and Jen finally felt Paul press Dave’s bellend against her hole. Both Daves cock and Jens hole were wet and sticky with Paul’s spit, but his dick still felt massive, bigger than anyone she’d ever had before. Dave smiled at her softly and pulled her close, his hands still spreading her cheeks as she felt his hot breath in her ear. “Don’t worry babe,” he whispered softly “we’ll go nice and slow…’ll be so good.”

As Paul pressed Dave’s big cock against her, he kept working with his tongue, lapping hard. His warm tongue flicked over Jens arse before he swirled it around Daves shaft, keeping him wet as he began easing Daves throbbing cock inside his slutty sister. He heard Jen groan in a mixture of pleasure and pain as Dave’s fat bellend squeezed inside her. Her hair was thrown back as she cried out in ecstasy.

“Oh Jesus Dave…’re the biggest I’ve ever had…..I’ve wanted you for so long…..put it all inside me…..Make me yours.”

Dave grinned at her and slowly pushed deeper, holding her hips as she took him all. “Fuck baby you’re so hot… fucking tight… feel so good…..such a perfect little hole.”

Jen moaned softly as she began to grind on her neighbour, slowly at first as she buried her head in his neck. It already felt amazing, and it only got better when Dave began fucking her, pushing deeper inside her tight hole. She squealed loudly as she threw her head back, and finally noticed her brother beside her, stroking his huge hard-on as he watched. Without a thought, she reached out for it and wrapped her fingers around him, feeling him throb as she wanked him off. Her brothers big dick was irresistible to her, and as she bounced softly on Dave’s dick, she smiled sweetly, looking up at her brother as she pulled him close, taking his cock between her red lips. Her tongue swirled around it, and she grabbed his arse to pull him deeper inside her willing mouth. The sound of her brother moaning turned her on so much, and she began bouncing harder on Dave’s cock. She was impaled at both ends, and as Dave’s heavy balls slapped against her arse, she took all of Pauls length, deep throating him as he stroked her hair. Jens whole body felt like it was on fire, and she pulled her brothers long dick from her mouth, staring up at Paul with a look of pure lust in her eyes.

“Fuck my mouth bro…..use me,” she sighed “fuck me hard…..give me your cum.” she ran her tongue along his prick before shoving her tongue into Daves mouth again, kissing him furiously “You too Dave…..fuck me like a whore…..I want your cum so bad…..fuck me…..I need your spunk…..fuck me hard.”

Jen went back to work on Paul, and groaned as he pushed his dick inside her hot mouth. Both holes were filled again, and both Paul and Dave were pushing deep inside her, grunting in pleasure as they used her. She felt like such a filthy whore, and nearly screamed when Dave pulled completely out before slamming back inside her.

“Oh fuck Jen…..Oh fuck…..I’m so close,” he groaned, pistoning inside her hot arsehole, “I’m going to fill your arse…..fuck I can’t hold back…..fuuuuuccccckkkkk!” He gave one final thrust, and Jen collapsed against him as she felt his cock explode. Her lips were still wrapped around her brothers massive cock, and she felt him grab her head as he moaned her name. His cock swelled between her lips, and rope after rope of creamy cum filled her mouth. Jen swallowed eagerly, still softly grinding on Daves softening dick as she took all the spunk that her brother had to give. She finally pulled away, and opened her mouth to show her brother the last of his load before she gulped it down. It tasted fantastic, and Jen knew instantly that this wouldn’t be the last time she got some.

Both Dave and Paul were spent, and collapsed on the couch as Jen finally pulled herself up. She knew her make-up was smeared and her dress was in disarray, but the way the two still looked at her made her feel so desirable. She leaned over and gave each hunk a long, passion-fuelled kiss, before muttering about how she had to go change before their parents got home. Knowing two sets of eyes were on her arse as she left, she made sure to keep her dress hiked up, and put an extra sway into her walk, even as she felt Daves cum begin to trickle from her used hole. It was the first time she’d been fucked like that, but it certainly wouldn’t be the last!

This short story is about how I was tricked into having sex through a hole between two restroom stalls. This actually happened to me about six months ago, and I decided to make it into a story for others to read. You can discover what kind of sex it was as you read…

I was in a shopping mall and was going to the restroom in a major department store. The restroom is in the women’s section on the second floor. So I got on the escalator and rode up, exiting at the top, and followed the sign to the restroom. It turned out to be right across from the lingerie section where I noticed a cute girl shopping for panties.

She was wearing a short pleated skirt, white fishnet stockings, and red fuck me high heels. She was hot! As I walked into the restroom she noticed me checking her out and smiled. I smiled back. I told myself that if she was still there when I came out, I would invite her for a drink…

I went into a stall on the end of the row of stalls and closed the door. As I dropped my pants and boxers, I heard someone else come in and enter the stall next to mine. That’s when I noticed the hole in the wall between the two stalls. It was about three feet from the floor, and about an inch and a half in diameter. But it was located forward of the toilet seat, so I wasn’t worried about a perv peeking through and easily seeing me.

Just then, a finger came through the hole and made a come here motion, then went away. I thought to myself, ok… What does that mean? Then it happened again. So I leaned forward and cautiously peeked through the hole. I couldn’t believe what I saw!

There in the stall next to me was the cute girl I had seen in the lingerie section! I could clearly see the bottom of her pleated skirt, the white fine fishnet stockings and now the lace tops, and the red high heels! What was she doing in the stall next to me?

Then her finger came through the hole again making the come here motion… So I stood up and slowly pushed my soft cock through the hole.

I immediately felt her hand grab me and start stroking. It felt good and so erotic as she jerked me off through the hole. I began to harden right away. I have a large cock, so as I did the hole tightened around me and soon I noticed I couldn’t pull it back out if I wanted to! Further, it was tight enough that it was acting as a cock ring, letting blood flow into my hard on but preventing it from flowing out.

So I was stuck there with a raging hard on and this cute girl slowly stoking me. No big deal I thought, since I will soften when I cum which she was clearly intent on making me do.

Suddenly she removed her hand and I felt a soft, warm mouth take my cock head in. She started sucking and it felt wonderful! Then she started moving her mouth up and down my shaft sucking hard as she did it. She sucked so hard that more blood flowed into my already engorged cock. It was so hard it was throbbing at this point, and I could feel the early signs of an orgasm coming on…

Then she pulled her mouth off of me and I felt something warm and hard, with a soft covering start rubbing up and down the length of my shaft. I felt something popping over the head of my cock as the rubbing continued. It felt like another cock head! That wasn’t a girl, it was a guy dressed like a girl!

I tried to pull out, but was so hard and engorged that I couldn’t move. My cock started to soften at the thought of another guy doing those things to me, but she just grabbed it and started stroking me as she sucked on my cock head. I immediately got hard again, as she took me in her mouth and sucked hard again engorging my throbbing cock.

Then she started stroking me hard up and down my entire length. As she did, I could hear her stroking her cock also. I could feel my orgasm starting to develop and could hear her stroking and breathing heavily.

Then I felt her cock on mine again, and she started rubbing it up and down my length. I felt one hand squeeze our cocks together, and the second underneath my shaft pushing up. Suddenly I could feel her jerking as she came, and I felt warm cum landing all up and down my length. She caught what didn’t land on my clock in her second hand. Next, she rubbed her cum all up and down my cock stroking it as she did.

I have just had another guy, albeit looking like a cute girl, cum on my cock! And she is now jerking me off using her cum as lube! Then it happened… She stopped stroking me and I felt something soft and warm pushing onto my cock head. The pushing got harder, and I felt my head slip into something tight and warm. She was pushing her man cunt onto my cock! She was going to fuck me!

Slowly the pushing got harder, and I felt my cock entering deeper and deeper. Suddenly, my cock head popped past something and slid in more easily. It was her sphincter! I was now almost all the way in… And it was warm and tight, it actually was starting to feel good!

Now she started pushing back and forth on my cock, causing me to fuck her ass… Soon, I felt an orgasm starting in earnest and once again tried to pull away with out any luck. I didn’t want to cum in a guys ass! But it was looking like I had no choice.

She was now riding me hard and was making me go all the way in and out with each thrust. There was no way I could stop it… My orgasm hit me like a ton of bricks! She felt me coming and must have squeezed her ass tight around my cock as she continued fucking me.

I came very hard, shooting spurt after spurt of cum into her ass! I must admit it felt really good… When I finally stopped cumming, I felt her slowly slide off of me. I felt my cock being wiped off on the head, felt a kiss on the end, then heard her exit the stall and restroom. I slowly softened and was able to remove my cock from the hole. I pulled up my pants and rushed out the door, but she was no where to be found. I had just had gay sex with a cute boi/gurl, and was now wondering if I would do it again without the bathroom stalls.

Happy fucking Halloween.

That was his thought as the alarm bell clanged this cold autumn morning. A costume, where the hell was he going to find a costume on Halloween day. The memo from the office booster club arrived in his inbox at exactly 5:55 pm last night. It was a lucky thing he even saw it. What the hell were they thinking springing a costume day at work on such short notice. Mandatory, imagine that, a prestigious law firm and they wanted the office dressed as clowns.

There had better be a big fat treat at the end of the day, and it better come in the form of cash. He showered and considered going in naked, costumed in his birthday suit. That would be enough to send the prudish secretaries running for cover, and would certainly cause more than one sexual harassment suit. Would serve them right, a costume on such short notice was enough for a mental harassment suit on his part.

Grumbling over his usual breakfast of a protein shake and a banana, he was dressed in his birthday suit, naked as a jay bird and he should just stay this way. Hang a sign around his neck…NUDIST! Deal with it!

Rinsing his glass and tossing the banana peel, he headed to his bedroom. Rifling his closet, did he actually own anything other then suits, shirts and ties? Inspiration struck, there at the very back of his closet hung a foreign item. The dress he had bought for that no good ex-girlfriend. But could he squeeze into it? Worth a shot I suppose.

He felt his smooth face, freshly shaved and started to smile. He grabbed the dress and slipped it over his head. Hmmmmmmm, not bad, but I need titties. He checked the drawer, the one he had reserved for her things and to his surprise found a bra, panties and stockings, luckily dark stockings, if no one inspected too closely they might not notice his hairy legs.

He pulled the dress on and wrapped the bra around his chest. Why did women wear these things, comfort was definitely not a design demand. Now to find boobs! His girlfriend was rather modest chested, so no need for watermelons. But, a couple of balloons, filled with water and wrapped in socks might just work. He constructed himself some titties and for added effect glued a pair of sawed off golf tees for nipples. He turned to look at his profile in the mirror. Boobies complete with erect nipples. The effect was rather good.

He slipped on the panties, tight enough to hide his cock, as long as he didn’t get aroused at work…fat chance of that happening! He had been looking at the same old co-workers for years now and no one had even piqued his interest enough to ask their name let alone stir any sexual desire.

Stockings slid surprisingly easily over his muscled hairy legs. The dress came to mid thigh and the look was complete, except for shoes. Where in the hell would he find a pair of size 10 women’s shoes at this time of the morning? And how the hell would he manage to walk in them?

He got down on his hands and knees…scooting to the back of the closet, cell phone held aloft to see if maybe something other than his standard black leather dress shoes might be hiding back there. And sure enough, that rotten ex of his had left a shoe box with sandals in them…tags still attached. She had no sense for money, at least not his money when she went shopping.

But at least they were sandals with no heels. He squeezed his size ten man feet into the size 9 woman’s shoe and fastened the strap. Maybe not a fashion statement with the slinky red dress, but better than his shoes. He winced as he stood up, the sandals tight and uncomfortable. It will remind me of how much this pisses me off at least.

But his hair, short and closely cropped, thick eyebrows…what to do about that?

Finding tweezers, surprised that he had some he stood in front of the mirror and quickly plucked his eyebrows into a semblance of womanly appearance. Smiling he found he liked the shaped trim eyebrows. He put the tweezers where he could find them easily next time. Now for hair. What to do for hair?

He started grinning as he remembered his neighbor two floors down had wigs. Lots and lots of wigs. She was a wig designer of all things. And she had borrowed coffee that one morning.

He grabbed his briefcase and headed for the elevator. Punching the 11th floor button he found himself smiling and humming “The Monster Mash,” the only Halloweenish song he could think of.

As he knocked on her door, he realized he didn’t even know her name, just thought of her as the wig lady, usually adding the adjective crazy to the moniker.

She answered his knock and stood staring at him with such a look of abject horror that he started to laugh. Once the laugh started he couldn’t stop. Her look never changed, but she backed away from the door…preparing to shut it, and probably lock every one of the dead bolts he suspected lined the door casing.

Finally catching his breath, he said, “Hi, I’m Thomas, I live upstairs, I am dressed for Halloween, but as you can see, a few key ingredients are missing. I thought maybe you could loan me a wig.”

At that point, her horror turned to mirth and she let out a girlish giggle. “Come on in. You need some help if you are going to pull this off.”

“I have made as many wigs for men as for women, and I think I have the perfect one for you…also a pair of shoes that just might fit better than those things you have on.” She led him into her work room. A mass of wigs, and a rack of clothes, a rack of shoes and a make-up table. “I don’t just make wigs, I do complete make-overs as well as the occasional low production movie costuming.”

He smiled, he had certainly wished he had known that before he had dressed in this outfit. “Maybe you can find me a costume, instead of this disaster I am wearing. I saw the look of fear on your face when you answered the door.”

“No, the look of fear was from thinking I was supposed to have a custom wig ready for a customer that I didn’t remember booking an appointment for. Apart from the shoes and the hair…you look pretty good. I am not even going to ask why you own a dress though.”

Frowning at the implication he said, “I bought it for an ex-girlfriend, she never came back to wear it. Found a better offer I guess.”

“Well that doesn’t matter, fixing you up is what we need to do now. So relax and let the expert have her way with you.” she winked at him as she went to work.

“Here’s a pair of heels, size 10 mens, and before you ask…lots of men dress like you do everyday.”

While she rummaged her collection of wigs, he sat down, discarded the too tight sandals and strapped on the black leather shoes. He stood up, wobbling and grabbed a chair to steady himself.

She laughed watching him, “You practice while I prepare the magic.”

After just a few minutes he found he could maneuver around the room, without too much wobble. He would sit at his desk and not move for the entire day…just another pretty face.

She sat him at her make-up table and transformed his manly face into a pretty, not quite beautiful, but definitely a pretty girly face. She added the wig and he gasped at the transformation. She added a “Ta-Da!” and announced him ready for Halloween, or a date with a handsome man. This was followed by a fit of giggles as she leaned in and kissed his cheek. “You owe me big time for this, and I want details of how many men hit on you today!”

As he was getting ready to leave, she looked at his briefcase and said, “That just won’t do.” She disappeared and came back with an over sized purse. “Put all the things you need in here for the day. I’ll have supper ready when you get back, I really am interested in how your day goes.”

He told her, “Thank you.” in the open doorway and her parting suggestion was, “Try not to say anything, just smile and look pretty.”

He laughed, then tried a girlish giggle. Raising his voice an octave, “Thanks for the advice.”

He arrived at his office on time, barely, and whisked in past his co-workers, everything from batman to Dracula to a fairy princess and a slew of other recognizable outfits. “They must have had advance warning of the costume mandate.” he thought.

As he was passing his secretary’s desk, he saw a note. It read “Junie called in sick, sorry, we called for a temp but they didn’t think they could find one for you today.” Inspiration struck. He sat at the desk, and quickly called himself in sick. He would be the temp for the day.

After a few minutes one of the secretaries, dressed in some sort of version of a bunny rabbit, stopped by his desk. “Hi, my name is Wilma, you must be Mr. Rexton’s temp for the day. I have good news and bad though. The good news is, he called in sick so you won’t have much to do today, and lucky for you because he is a tyrant. Bossy and demanding. The bad news is that you were supposed to wear a costume, but no worries, we understand it was short notice. Thanks for coming in, and just answer the phone, take messages and enjoy the day I’ll just hop on about my business.”

He managed to stammer out a simple, “Thanks.” a little hoarse, but he could always claim he had a cold. He was rather insulted by the implication that he was a tyrant and vowed to look into her upcoming Christmas bonus, to make sure it was of an amount worthy of a tyrant.

The phone was surprisingly quiet and no one approached his desk so he worked on his files, a good day to catch up on paperwork. Lots of glances and a few open stares as he sat working…until lunchtime. One of the newer attorneys came over and sat on the corner of the desk. A large “S” adorned his chest, he apparently fancied himself Superman.

“You must be the temp. I’m glad you didn’t wear a costume, because,” he leaned in very close, “then I wouldn’t have known how beautiful you are. He grinned and continued, “There’s cake and treats in the lunchroom, come on and enjoy.”

He stood and offered his arm. She stood, placed his hand on the offered arm and followed him into the lunchroom.

There was enough chatter that he found he could just smile, or pretend to be chewing his food and nod. Lunchtime over, day half over and he was smiling, he had pulled this thing off. But damn, how could they believe that he, He was a woman.

By 4:00 most of the staff had gone home and he decided that he could go into his own office and get a couple of hours of real work done before his usual quitting time of 6:00.

A quick trip to the bathroom and call it a done deal for the wig.

There was another woman in the hallway and they stopped and stared at each other. Wow, she is stunning he thought, how come I never saw her before. And why is she not wearing a costume?

She said, “Hi, I’m a temp here today.”

He smiled, “Me too.”

They walked into the bathroom today making, what he hoped, was girl talk. He stared around the women’s washroom. Not so different from the men’s, apart from the urinals.

He went into the stall and struggled with the panties, then decided he better sit down to have this piss.

They both emerged from their separate stalls at the same time and stood washing their hands. He felt almost like a pervert, in the ladies can, openly leering at a woman, who thought he was a woman. He felt the stirrings of his cock. Oh no, this could be bad.

She reached over and placed her hand on his arm. “I know we don’t know each other, but we are both temps here, will probably never see each other again, and I am attracted to you.”

His heart pounded in his chest. He swallowed hard, thought of the law suit in the making, but hey…this was her idea.

He stammered out, “You are beautiful, and I am so attracted to you, I could do you right now.”

She giggled and led him into the largest stall and clicked the lock on the door.

She leaned in for a kiss and he kissed her back. Her tongue drove deep in his mouth, thrilling him to the point of no return. He grabbed her shoulders and pulled her closer, grinding his hips to hers. She pulled back, and he thought, “She felt my cock throbbing against her hot pussy and knows I am a man.”

But she wasn’t shocked or looking afraid at all. She ran her hands over his shoulders, and leaned in to renew the kiss. She reached up to feel his boobs and this time he pulled back. She’ll know for sure if she goes squeezing on these water balloons.

She looked at him quizzically and said, “This is rather awkward, but maybe if we each put on a blindfold, we won’t feel so self conscious. He readily agreed, just bend her over, fuck her hard and get the hell out of there. “No one even knows who I am.”

“OK, good idea.”

She bent and removed both of her stockings, handing him one. They tied the make-shift blindfolds over their eyes and promised no peeking. He reached for her but it was too late, she had spun him around backwards, pushed him forward over the toilet and was hiking up his dress in the back. With one hand bracing him forward, she ripped his panties off his body and before he could utter a word of protest there was a hard cock pushing against his ass.

The only thought was “Shit…I am not the only man dressed as a woman today and I am about to get it up the ass. Can’t he tell an ass from a pussy?”

The cock kept pushing at his ass and his own cock got harder, thicker and longer, throbbing painfully as it bobbed up and down.

“Stop it you fool…I’m a man too,”

The manly voice from behind said, “I know, I could tell from the first minute you walked in the door Mr. Rexton, but I have been wanting to fuck that tight ass of yours for years.”

“Happy fucking Halloween!” and with that he thrust his cock into the tight ass, letting out a grunt, accompanied by a scream. Without letting up he fucked his ass, hard and fast, full strokes.

Mr. Rexton was numb with shock. He was enjoying having his ass forcefully taken. The initial pain actually made his own cock harder. He reached down to stroke himself as his ass was being destroyed by the monster cock that pistoned in and out like a machine.

The bathroom rang with the sound of two men taking pleasure from one another. The smell of musk hanging in the air. His ass on fire, he felt the first jet of cum and almost lost his own as this ‘woman’ came in his ass. He was still panting, still hard and still needing when the cock slipped from his ass. The other man spun him around again, and dropped to his knees. Mr. Rexton was getting the best blow job he had ever gotten…and from a man.

The man sucked and bit at his cock. He braced both arms on the stall walls and pumped his hips. Throat fucking this heavenly mouth. With a grunt, he felt his balls tighten, drawing up tight to his body and put both hands on the mans head and held him there. His balls resting on his chin while his cock pumped a load of cum right down the throat of another man.

Gasping from the exertion and the pleasure, he felt himself embraced, hugged close to this near naked man…and then the feel of lips on his. He could taste his cum and he licked at the lips eagerly, driving his tongue deep to get more of that taste.

The door opened and he found himself alone, blindfolded in the women’s washroom, cum leaking out of his ass and the taste of his own seed still lingering on his tongue.

He slipped off the blindfold, retrieved his panties and pulled them on.

Still shocked at what had happened he packed his purse and decided to call it a day. Who was that woman/man?

He would have to live with knowing that someone in his office knew what he had done. He would have to live with what he had just submitted to, and the knowledge that he had loved it.

But those were thoughts for another day.

This was Halloween and he was going to enjoy the rest of his day. And he still had to return the borrowed items to the crazy wig lady. The cute crazy wig lady.

He rapped sharply at her door. She answered and stepped back to allow him to come in. Once he was inside, she shut the door and locked it. She turned to look at him and then grabbed him and started to kiss him. He was hesitant at first, then eager as her tongue delved deep into his mouth. Her kisses both shocking and arousing. Her hands ran over his chest, dipping lower to rub at his cock through the dress and thin panties. He wasn’t sure what to think, but decided that thinking might be a little over rated at this moment.

Two sets of girl clothes hit the floor just inside the entry. She clung to him, his recently sucked cock springing once more to full attention as his thoughts strayed to the feel of that cock in his ass. She grabbed his hand and pulled him to her bedroom where she pushed him onto the bed and climbed on top of him.

“What is with all the sexually aggressive people today?” he pondered. Not that he was complaining though. He lay back while she sucked on his cock. Her skills were amazing. His cock throbbed, harder and longer with each poke of her tongue at his piss slit. Her hand cupping his balls, gently at first, then she increase the pressure until he was ready to scream. She let go and lay down beside him.

“So, tell me, how many men hit on you today?” she laughed as she looked sideways at him, licking her lips, one hand lazily stroking his cock.

“Only one. Just the one man…oh,” he grinned, “and one woman.”

“Hmmmmm, did you fuck the woman?” she had just a hint of a frown on her face.

“No, I promise you I did not fuck that woman.” He laughed and rolled on top of her, “But I am going to fuck you!”

He took her hard, her cunt already wet and slippery. His thick cock sliding all the way in and he nestled deep inside for a moment before pounding her cunt as hard as he could, as hard at that man had taken his ass. When he thought of his own ass getting fucked, his cock twitched inside the warm wet pussy.

He pulled his cock free, kissed her on the lips and said, “What I’d really like to do is fuck your pretty little bum. I want to shove my stiff prick right up your tight brown mouth and see how well you kiss at that end.”

She looked deeply into his eyes, “It’s about time. I have wanted you since I first borrowed that coffee.”

With that she rolled over, raised herself on her hands and knees and waggled her bottom at him. “Do you think you can find it, or do you need a little help?” Without waiting for an answer, she reached back and parted her cheeks, fingers digging in, giving him a clear view of her delightful asshole.

He wasted no time, put his cock at that back door and pushed, it was almost painful, the pressure on the tip of his cock. He thrust his hips forward and leaned his body ahead to let his weight push his cock, and was rewarded with a release of her sphincter muscle. The tiny rose bud blossomed around his cock, kissing it tightly. His head now completely enclosed, he felt her body quiver, the snug fit rippling around the crown of his cock. He wasn’t sure if the moans coming out of her were of pain or pleasure but when she pushed back against him he took it as silent permission to drive his cock home.

His balls slapped upwards against her wet cunt, making a delicious sound to accompany the whimpers and moans. He pummeled her ass, hard and fast. His cock a blur as he made full strokes, tip to base, almost letting his cock slip out then driving it back in so that his balls continued the assault on her pussy.

She started to buck underneath him and he fancied himself a rodeo rider trying to stay on the bull. He grabbed a handful of her hair and held on, sealed to her by the tight grip of her asshole on his cock. His own asshole twitched as he felt that familiar and welcome tingle start in his balls. He imagined he could feel the cum surging up and through his cock, felt his little piss hole flare as he shot his load deep in her bowels.

As he emptied his cock, his free hand snaked under her, tweaked at her clit, rubbed hard until he felt her shudder. OMG! when she came, with his cock still in her ass, it felt like she was trying to strangle him. Her ass spasmed and convulsed while her entire body shook with the force of her orgasm. It felt like hours before she stopped moving under him. He pulled his hand free and tasted her sweet girl cum, then untangled his fingers from her hair while his cock reeled itself back in, retracting closer to his body and finally slipping free of the tiny mouth that had tried to devour him.

I lay there on my side, with Sarah behind me her arm draped over me; we were in a spooning position and I could feel her hard cock pressing against me, probing my asshole. She started kissing me on the neck while playing with my nipples; I knew what she wanted. She was really trying to seduce me into it to. Until now I had, had no problems at all with any of the things we had been doing together. Hell, I had even sucked her cock and enjoyed that, but the idea of bending over and letting her stick her big fat dick in my ass…that sort of made me a little uneasy. I had seen a lot of anal sex videos, of course, all of those videos had girls getting’ fucked in the ass; I had never watched a gay porn in my life. Regardless, most of the videos I had seen the girl always made it seem so god damn painful; sure about midway through they would start to seem like they were enjoying themselves but it was the wait they had to endure until it slipped from painful to pleasurable.

She must have known I was nervous because she seemed to be trying pretty’ damn hard to convince me to give her what she wanted. I moaned as she sucked my neck and blew in my ear, sending chills up and down my spine. She was driving me crazy, and I was really trying to figure out if I wanted to go through with this or not.

“It’ll only hurt for a few seconds, I promise.”

She obviously knew what I was worried about; yet strangely, as she whispered that in my ear and ran her hand soothingly over my chest at the same time, I could not help but relax. It dawned on me then; I had only known Sarah for a day that was true.

However, Sarah was not really Sarah; Sarah was really Bryan and I had known Bryan now for two and a half years. By this point, I felt like I should be able to trust him pretty’ well, so what the’ hell was I so afraid of? As she continued pressing up against me I caved in and turned over onto my stomach’ and wrapped my arms around the pillow under my head.

She must have gotten the point because Sarah got up and reached for the lubrication and I jumped at the feeling of the cold stuff hitting my asshole. Then I felt something stiff but not big pushing into me; it wasn’t’ big enough to be her cock, and I realized after a moment it was her finger.

She worked her index finger deep into my ass and started massaging my prostate gland; I moaned as she rubbed up against it and I felt my cock start to go hard between me, and the bed. After a few moments of fingering me, she pulled out slightly and I felt my asshole stretch as she worked an additional finger back into me.

She now had two fingers knuckle deep in my ass, stretching me wide and playing with my prostate. It felt good but I also had this strong feeling of fullness and I realized, if it felt this strange just having two fingers inside of me how out of place was it going to feel when she actually started fucking me?

I felt her pull her fingers from me and she reached for the lube, applying’ more of it to my asshole and I heard an additional squirt indicating that she was applying some to her cock as well.

I took a deep breath and tried to relax myself; I knew from experience of fucking girls in their asses that if you were to tense then it would make it all the more difficult and painful. I braced myself, gripping the pillow as I felt her climb over top of me and she started running both hands up and down my back trying to help me relax.

“Are you ready?” she asked softly.

“Yeah; just go easy okay?”

“Don’t worry baby. I will.”

I felt one of her hands move away from my back, she used it to grab her cock and I felt the head of her big shaft pressing against my well’ lubricated and slight widened asshole. She applied pressure using her hand to guide herself’ into me; I felt myself stretching wider and wider and the feeling of fullness returned but a lot more noticeable. She inched her way into me and I felt as though the feeling were becoming overwhelming.

I bit my lip, shut my eyes and’ held my breath trying not to cave and give up to easily on this.

“Are you okay?”

“Yeah,” I replied.

“Do you want me to stop?” she asked.

I could tell by her voice she was not annoyed at all with me; she sounded more concerned and I could hear it behind her words that she really cared.

“No, it’s okay” I said. If she cared that much about me, then she deserved to enjoy herself so I would at least try to stick it out a little longer.

She continued inching her way into my tight asshole until I felt her full body weight on top of me and I could feel her balls pressing against me. She was all the way inside of me now and’ just staying there not moving an inch waiting for me to adjust to the sensation of her huge cock deep inside of me.

“You okay?” she checked.


With that, she lifted herself up just slightly, pulling her cock about halfway back and then driving it all the way back into me again. I gasped at the feeling of her moving out and then back in and then she repeated the same action a second time. By the third thrust, I could feel a strange hot feeling deep inside of my asshole with each thrust that she delivered. She was fucking me softly, making extra sure not to hurt me in any way and I could feel the dull pain beginning to subside as the pleasure started to kick in.

When she realized I was starting to enjoy myself, I noticed she had started to pick up the pace a little and was starting to fuck me just a little harder and faster. As my cock started to get really’ hard, I arched myself up off the bed slightly so that my ass was sticking out. She took advantage of my cooperation and grabbed me by the hips getting a firm grip; she started fucking me harder and faster now, breathing heavily as she slammed in and out of me.

I started pushing myself back against her to meet each of her thrusts. I could hear the sound of our sweaty bodies slapping together and my cock was throbbing by now; there was this strange sensation in the pit of my gut and it kept growing and growing. It felt like something huge was about to happen and I found myself praying that I was not about to have an accident from all this stimulation.

It felt like my insides were being twisted but in a good way if that makes any sense at all; I moaned and embraced the sensation and could not help but call out to her and beg her to fuck me harder.


It came out in a low raspy voice and she almost didn’t’ hear me.


“I said…harder…fuck me harder!”

“Tell me what you want me to do baby,”

“Oh god…agh, ugh, ugh, fuck’ me harder!”

She did just as I asked and started really pounding away at me now; the bed shaking underneath of us making the familiar creaking sounds of a couple having some really intense sex.

We had thin walls and I was sure by now at least one of our neighbors could hear what was happening. The problem there was they would hear me begging to be’ fucked harder instead of a girl uttering those words, and I was sure that later on one of my neighbors would probably be giving me an odd look when I ran into them.

I gasped as that twisting feeling over took me, and the tip of my cock started to burn as the room began to spin. I’m’ not sure how to describe the feeling really.

It felt like my asshole was squeezing her cock, clenching and unclenching over and, over again. The spasms became more powerful and as they did, my cock started to shoot a hot load of sticky cum all over my bed sheets.

“Oh shit,” I moaned loudly.

Sarah was pounding me now and now that I had reached my orgasm, she could stop holding back on herself. A few more powerful’ thrusts and’ grunting and moaning and she buried herself, balls deep in my asshole and exploded. Pumping me full of her cum before collapsing on top of me and we’ both sank into the mattress my face buried in my pillow.

We were out of breath and both of us were covered in sweat, exhausted and I actually felt kind’ of hungry. I could feel her cock starting to go limb inside of me and she pulled out rolling over and dropping back on the mattress at my side. We lay there for a few minutes, just trying to collect our thoughts before I turned over and smiled at her. She smiled back and moved closer to me, resting her head on my chest as we finally relaxed and managed to catch our breath.

“That wasn’t so bad was it?” she asked

I laughed, and ran a hand through my hair staring up at the ceiling. “Felt pretty fucking good,” I said. I could hardly believe it myself but it was the honest’ truth, I really had enjoyed every minute of what we just did.

We must have drifted off after a few minutes because I lost track of time and when I woke, I glanced at the clock and was surprised to see that it was almost 9:00 at night. We had slept practically the entire day after our little fuck session ended and I was starving now.

I sat up on the bed and that’s’ when I noticed Sarah wasn’t’ beside me anymore. I rolled out of bed slipped into my boxers and made my way out into the living room to find Bryan sitting on the couch watching TV.

“I see your’ awake finally,” he said smiling at me.

“Just woke up; I’m starving’ to.”

“I made a sandwich about two hours ago; we can order pizza if you want.”

I grabbed a few of the menus that we kept in the kitchen drawer and after a few minutes, we settled on the closest pizza shop that we could find and ordered a large pizza with extra cheese. I sat down on the couch while we waited for the food to get there and could not stop thinking about what we had done earlier and the night before.

All of this was so fucking crazy, last night there was kind of an excuse seeing as we were both so drunk and all; but today we had been completely sober and that had not stopped us. What scared me the most was that I had enjoyed all of it more then I had ever enjoyed any previous experiences of my life.

This had been some of the best’ sex I had ever enjoyed; so what did that say about me if the best sex I had ever had was with another man who liked dressing as a woman? I had no idea what was in store for me or Bryan/Sarah or our future for that matter.

I just knew that right now the feeling of euphoria had worn off and now I could feel the head ache of confusion starting to kick in.

Chapter 1

So, there I was dressed up as a girl, ramming my ass back and forth on a dildo suctioned to a wall. In front of me was the blonde demoness responsible. As she moaned passionately, fingering her cunt wildly, my rock hard dick surged with life anew and huge spurts of cum shot out and onto my face and in my open mouth.

To understand my situation, you’d have to understand how I got there. The story starts in earnest two hours earlier.

My name is Robert Rodriguez. I’m currently enrolled in my third year of college and am aiming for a degree in Aerospace Engineering. What can I say? I’m good at building things and have a fascination with flying. I’d received a good deal of money to go to college, partly for my Hispanic heritage and partly for my cross country super-stardom. I’m a tall, athletic guy. 6’2″, about 165 pounds, I’m slender with a runners physique. Toned, but not ripped. Throughout college I’d had a fair sure of girlfriends, but nothing crazy or particularly long lasting. I was a pretty normal guy. Twenty years old, I had a job, a place to live, and no money troubles. Life was good for me, until winter break.

I come from a ski town. We have a local mountain about thirty minutes away and I love the damn place. I was born to ski. Since I was one year old my parents stuck me on a pair of skis and sent me downhill. When I got home, the mountain was barren. No snow, no powder, no winter wonderland.

It sucked.

Three weeks with no snow. I only had two weeks left on break. And I hadn’t skied one run! It was probably about 10 AM when the first event sending my life down hill occurred. I was asleep, my parents and sister had already left when my phone began going off. It was a good buddy of mine, Greg.

“Rob, look out your window!”

“Huh-what?” I mumbled, still not fully awake.

“YOUR WINDOW! Look out it!”

I pulled open the blinds and saw a dazzling beautiful sight. Several feet of snow covered my yard and the street beyond.

“Fuck yeah.” I said quietly.

And then my brain kicked in. Fuck no. Last season I had broken my right ski. Having no snow at home, I still hadn’t bought a new pair because it hadn’t been an issue. Buy a new pair now you might say, well here is the issue. In my town there is such a thing as the powder rule. If the snow is falling every ski store in town will be closed. I was trapped with no skis.

Being a smart guy I refused to accept this. I would ski! As I paced my room a poster (of skiing of course) caught my eye. It was signed by several pro skiers. As I stared at the sheet I remembered how I got it.

One of my dad’s best friends Eric owned one of the local ski shops and when I was ten he had gotten the poster signed for me. Eric, his wife, and daughter had always been great family friends. In the winters we skied with them and in the summers white water rafted. They were good people. I knew that Eric would have ski equipment at his house. I also knew he and his family were out of town. We’d had them over for dinner less then a week ago. This was the second event that continued my descent. I had a spare key to their house. When I was younger I would house sit for them and had never returned the key when I went to school. I would go in, grab a pair of skis and leave. Shred the slopes and return them with nobody the wiser. I enlisted Greg’s help as two hands would be better then one. And I didn’t have a car.

He picked me up and we drove down to Eric’s neighborhood and pulled up to his street. Zipping our sweatshirts up we stepped out into the cold. Having lived their all our lives the thin layer of protection was enough for us not to freeze in the brief crossing to the house, but we still wanted to get out of the cold as fast as possible. I unlocked the front door and we entered. Here I thought fate was kind to me because right next to the front door on the table was several pairs of skis. I sifted through them and found a pair that would work. A car door shut with a loud clunk. I looked at Greg, Greg looked at me. We both looked out the window and saw a car parked in the drive way. I grabbed the skis and we dashed towards the back door. The door we discovered was snowed in. No exit that way. We dashed towards the stairs in hopes of finding a window on the second story to clamber out. I locked the front door again with a loud ka-thunk. We got to the second story and opened what I could only surmise was Eric and his wife’s bedroom window. Greg climbed out first and I handed him the skis. He grabbed hold of them and proceeded to slip off the roof. He landed in a snow drift with a soft puff of snow. He hauled ass to his car with the skis. I could see the person in the drive way, their body and head obscured by a large parka look at the strange man running with skis. Greg got to the car and peeled out of there. That son of a bitch left me. I didn’t fancy my chances with the roof so I dashed back down the stairs. As I got to the bottom the lock on the door began to turn. I jumped behind a couch. The person entered, I could hear their boots. They locked the front door and went into the kitchen. I peered around the edge of the couch and my eyes flicked to the door. The lock was so loud! If I turned it they’d here me and then I’d be fucked. I looked into the kitchen through a plant next to the couch as the person removed the parka. It was… Mia!?! Mia was Eric’s daughter who apparently did not go with her parents on their trip. Mia had been unable to attend dinner the other night, but I’d assumed she’d be going with her parents. Between my panic and mental fretting I looked at Mia. Under the parka she was just wearing a volleyball t-shirt. Her breasts pushing at the fabric straining for release. Damn she had a nice rack. I hadn’t seen her since I went to school which was five years ago. Back then she was fourteen and I was eighteen. I did some quick mental math to figure out if it was creepy that I was ogling her. Nope she would be eighteen now. Not creepy. Asides the fact I was hiding behind her couch. She spun around and opened the fridge and bent over. Her tight little ass showing off perfectly in a pair of jeans. I felt my cock stir slightly. I remember Mia being annoying when I was younger. She seemed a bit like a spoiled brat at times. Her father always gave her what she wanted and I remember being jealous of her massive allowances that she bragged of every time I saw her after I’d gotten of a hard shift at work. Contrary to the annoying gawky girl I remembered was one screaming hot chick in front of me. She pulled out a tub of yogurt and dipped a finger in it. She put the finger in her mouth and sucked it off. Fuck this, I thought. I have to get out of hear.

Event number three. I saw no other alternative. I knew Mia. She knew me. Hopefully, I could explain this rationally and not go to jail. I stuck a hand above the couch and called out, “Hey, Mia. Please don’t freak out or anything, but I’m beyond your couch.” She visibly jumped when I called out and stood up. As I rose I got my first full look at Mia. She was tall, about 5’11”, that explained the volleyball shirt. She had her straight, blonde hair loose and around her face. Her green eyes widened in surprise and her, I’m just guessing, but C sized breasts jiggled as she jumped in shock. I grinned sheepishly.

“Rob!?!?! What the fuck are you doing in my house!?!” she yelled

“Whoa! Whoa! That’s the panic I was hoping you wouldn’t do!”

She just stared at me angrily.

I tried to explain as best I could, babbling about the snow and skiing and how I needed skis to borrow. I watched her carefully as I explained. Her expression changed from shocked, to pissed, to something else, something like crafty.

“Well. That’s it… Please don’t call the cops.”

She smiled, but it wasn’t friendly. More akin to the smile a shark gives its next meal.

“Oh, no. I wouldn’t do that.” she reassured, except I didn’t feel reassured.

She stood up. “Here why don’t you come down to the basement.

“No. No. I really should be going.” I said quickly.

“You just broke into my house. The least you could do is come down to my basement.” She walked past me and I uneasily followed her downstairs.

The basement was well furnished. It had a big couch with a large flat screen tv. I could see a door to the right that I guessed was her room. It was huge with a big closet in the back. Like I said spoiled. I sat on the couch and Mia stood in front of me.

“So, here’s how I see it. You broke into my house with the intention of stealing-”

“No! Borrowing!” I interrupted.

“It’s stealing, Rob.” she continued. “So I think the least you could do for me not calling the cops or my dad is do a few small things for me.”

I swallowed. “What few things?”

She smiled. “For starters you can take off your shirt.”

I didn’t like where this was going. I slowly grasped the hem of my shirt.

“That’s right.” She encouraged.

I lifted my shirt of my body and sat there, the air conditioning raising goose bumps on my chest.

“And now the pants.”

I really didn’t like where this was going. I stood up and undid my belt. As I lowed my pants I saw Mia begin tweaking her nipple with her fingers through her shirt.

“Mmmmmm, very nice. Now lose the boxers.”

I lowered my boxers to the ground as my cock throbbed and slowly began to rise.

“Oh, yes!” Mia let out a gasp of delight.

I blushed in embarrassment and humiliation at my situation.

Mia stepped forward and grabbed my hand.

“Come on!”

“Come on where?” I asked as she dragged me towards her room.

“It’s time for a shower!”

She pushed me into the bathroom and into the shower. She cranked on the water. I flinched from the sudden change in temperature. She shut the shower door and disappeared. I stood under the water like an idiot as the bathroom began to steam up. I heard the bathroom door open and turned. There was Mia. Completely naked and completely gorgeous. Her nipples were erect and her pussy shaved. My cock sprang to attention. Maybe this wasn’t such a bad thing I thought. Until I saw that she had a razor in one hand and a bottle of shaving cream in the other.

“What are those for?” I asked.

“I like my men smooth.” she answered.

Mia climbed into the shower and got onto her knees her face just inches from my dick.

“Oh, you look excited.” she giggled.

Mia began massaging the shaving cream into my legs and then in deliberate talented strokes began shaving them. She then moved up to arms, armpits, and chest. She reached down and began massaging my balls with the cream. I groaned in ecstasy.

Kissed my neck and murmured, “Time for these.” She got back to her knees and completely shaved my balls. My entire body asides my head was completely hairless. She stood up and shaved of my stubble and removed all remains of a beard shadow.

“Now you get all cleaned up. I’ll be right back.” She exited the shower and I stood there in a stupor.

I washed the hair and cream off my body and turned of the water. I stepped out, toweled off, and walked into Mia’s room. Her closet door was shut, but the light was shining out the bottom.

She called from inside. “I’ll be out in a second, leave the towel in the hamper.”

I didn’t want to go back to being naked, but did as she was instructed. I walked back out into the tv room to put on my clothes again. They were gone. I’d left them on the couch and now they were gone. In their place was a pair of black lace panties.

Oh god.

“Put them on.”

I turned to see Mia standing in the door way clad in a matching pair of black panties and an incredibly tight “Ski Bunnies Are The Best” shirt. Her nipples were rock hard through the thin material. She was hiding something behind her back.


“I said put them on.”

Her voice was almost hypnotic. I knew I had no choice. I pulled the panties up my leg, feeling the luxuriousness of the fabric against my shaven legs. I pulled them up and over my crouch, pinning my balls and cock between my legs.

“Oh, my, god. You look fabulous.” She pulled her hands out from behind her back. She was holding a make up kit and a black wig. The wig was the same color as my hair, only a little longer and styled into a girls cut.

“Come here, Robin.”


“I said come here, Robin. Now don’t make me repeat myself again.”

I walked towards her and she led me into her room. She seated me at her desk and spun me around in her chair. She went to work immediately with the make up kit. Applying foundation and plucking my eyebrows until they were thin and girly. She applied eyeliner and mascara.

“Pucker up.”

I stuck my lips out and she applied a dark red shade of makeup. She snugged the wig down over my head covering my short hair cut and fixed in place with several hair pins.

“Shake it out” she instructed.

I shook my head and could feel the wig stay firmly affixed in place.

“Oh, you look so gorgeous, Robin!!!” she squealed. She grabbed a mirror to show me.

Now I suppose I had fairly androgynous face, but having a beard always helped keep me masculine. With such a close shave, make up, and wig. I didn’t even recognize myself. Staring out of the mirror at my was a tan, beautiful, young woman. One who I wouldn’t think twice about fucking. Mia had worked her magic perfectly.

“Ok, stand up!” I rose. “It’s time to get you an outfit!”

She ran back into her closet and rummaged around. She came back with her arms full of clothes clutched to her breasts. I saw sexy stockings, bras with holes in them, crotchless panties, corsets. All sorts of crazy sex clothes.

“Where did you get this stuff?” I asked in amazement.

“Oh, you know, Daddy’s allowance and such.

“Mia, why are you doing this to me, don’t you have a boyfriend or something?”

She turned to and gave my balls a sharp squeeze. “Robin, somethings wrong with your voice, it’s all deep.”

“Mia, what are you talk-”

She gave my balls another, harder squeeze. I sucked air in through my teeth and did my best try at a girls voice. It came out soft and high. I fooled myself as I repeated my question.

Mia smiled at my voice in contentment and answered, “I had a boyfriend, but he was so boring. He wouldn’t let me fuck him. So I tried girlfriends. They were better, but they were missing something. This.” She stroked my cock through the panties.

“Now lets get you dressed!”

“But, Mia-”

“No, buts, Robin!”

She turned me around and lifted my arms. Picking up a corset she wrapped it around my waist.

“It’s lucky were such close sizes, eh, girlfriend?”

I blushed again and shifted uncomfortably.

“I asked you a question.” Mia gave my ass a sharp smack and I jumped.

“Y-yes, Mia, It’s lucky!”

“Good.” She began lacing the corset down my back. “Okay, inhale a little bit.” I took a bit of a breath and she tightened the corset. I looked in the floor length mirror on the wall and Robin looked back. A tall, hot chick stood in the mirror. Not the college student looking to ski.

“God, you look sexy.” Mia whispered in my ear as she pressed her breasts against my back. I stared at us in the mirror. Mia was running her tongue down my neck and was caressing my stomach. The corset pulled my sides in just enough to give me hips and even managed to push my chest up a bit. The only hint that I was no lesbian lover of Mia’s was the straining bulge in my panties.

“Oh, Mia.” I moaned girlishly.

Mia smiled. “Now that’s more like it.” She picked up a padded bra and slipped my arms into it. She buckled it behind me. Next came the stockings. Black fishnet. Last was a tight black dress that barely came down over my ass cheeks.

“And, voila!” Mia cried as she admired her handiwork. I was completely transformed. There I was standing in Mia’s arms, one helluva beautiful girl.

“Now it’s time for fun!” Mia whispered in my ear. I wasn’t sure I wanted to know what fun was, but I was this far down the rabbit hole with no hope of escaping so I put up little resistance as she led me back into the main room of the basement. She ran back into her room and I could hear her rummaging around in drawers.

“Close your eyes!” she called.

I dutifully shut my carefully painted eyes and in my mind I was imagining all sorts of insane things this girl I thought I knew could be getting. I heard her walk back in, her bare feet padding on the carpet.


I opened my eyes and there she was this demon temptress holding an eight inch long, fleshy dildo.

“Oh, no, Mia! I can’t!” Robin’s voice, not mine cried out.

“Oh baby,” she said as she straddled me and waggled the dildo in between our faces. “You know you want to.”

And the thing is, I wasn’t entirely sure that she was wrong.

Mia licked the tip of the plastic phallus and swirled it around in her mouth. She pulled it out a strand of saliva connecting her lips to it. She put it to mine and with a little resistance I opened my mouth. She slowly pushed the cock in and I licked it slowly, lavishingly. She laughed as a closed my eyes and leaned forward to take more.

“Oh, my, my, aren’t we hungry for cock?” she asked.

“Oh, Mia, I-I don’t know…” I answered unsure.

“Don’t worry about it, Robin. You’ll love it! Trust me.”

And I did.

She led me over to a wall and attached the dildo to it with the suction cup at the base. She pushed me to her knees. Her panty clad pussy was just inches from my face. I placed a small kiss on it. She threaded her fingers through my hair and said, “You’re getting ahead of yourself, baby.”

She helped me to my hands and knees and sat on my back, lining the giant dildo up with my ass. I didn’t know what I was doing as she led me towards the buttfucking I knew was going to happen. She placed the tip of the cock on my rosebud.

“Now push back.”

I did, slowly and it felt… I don’t know painful, glorious, I’m not sure. I felt my ass start to stretch around it. I let a whimper of pain out. And then… the tip entered me. I felt my anus stretch and the dildo go in just slightly. Mia stepped off of me and came around to my face. She bent down and looked at me in the eyes. She gave me a wicked grin.

“Too slow.”

She put her hands on my shoulders and pushed me back. The dildo rammed into me, all eight inches. My cock sprang out the top of the panties, rock solid and spewing cum all up my outfit.

Mia laughed. “Ah, Robin, you messed up your outfit. Clean it up.”

I looked up at her, tears smearing my makeup slightly.

“Go on.” she encouraged.

I tentatively shifted, the dildo shifting in me too, causing another spurt of gooey white. I scooped some up in my fingers and tentatively put it up to my lips. I licked it. That’s when I broke.

I smiled up at Mia and scooped up the rest of the cum and eating hungrily. I began fucking myself on the dildo in earnest. Back and forth, harder and harder, and loving every minute of it.

Mia took off her shirt and sat in front of me, playing with her nipples, and frantically frigging her cunt. I moaned loudly at the brutal ass fucking I was giving myself. She saw this and began to pant.

“Oh, Robin! OH! I’m cumming! I cumming! I’M CUMMING!!!” Mia lost it and came hard. And so did I. This brings us to now.

I lay my head in her lap and collapsed off the dildo. Mia stroked my hair.

“Now wasn’t that fun?”

It has been less than a couple of weeks since my time with the guy in the showers at the gym and was still waiting to hear from him.

After his wife caught us he quickly dressed and they disappeared into the night. I hadn’t seen Tara or my ex and was getting a little tired of jerking off. Thinking I might have to go on the prowl I came home as the phone was ringing. As I was returning from an away job I hoped it wasn’t my boss with another assignment as I needed a break.

As I picked up the phone the number was vaguely familiar but I was drawing a blank as to where I knew it.

As I said hello a low girlish voice said: “Is this the beautiful man I met at the beach?”

Remembering Benni now I replied: “Yes, is this the little cutie I sucked off with the sweet cum?”

He laughed shyly and said: “Yes I was afraid you might not remember me, you naughty man.”

Well I could see where this was going and was ready for something new so played along.

“So, hot stuff, what’s up? Have you been thinking about us?” I ask.

“Yes, especially you Daddy, I would really like to show you something special that hardly anyone ever sees. Would you like that?” He continues in a voice that makes me think of a young girl.

“What is on your mind sweet thing? Looking for a top for that cute bottom of yours?” I say playing along with him.

“Yes, I am wondering if you would like to come play with me. I have been thinking about playing with you all the time.” He continues.

“You know, I have been wondering about you too. Tell me the nastiest thing you want to do to help me decide if we meet.” I say, not telling him I was ready almost as soon as I heard his voice. The girl thing has me hard thinking about the possibilities.

“Well, I like to play dress up. Would you like me to dress up for you?” Benni asks.

“Sure, tell me about your outfit, what will you wear?” I ask squeezing my cock through my pants.

“Oh, Benni Girl can’t tell you that. It’s a secret, but you won’t be disappointed. I will tell you that my little boi pussy is ready for you to do to it what you did to your friend. Benni really liked watching Daddy’s handsome cock sliding in and out of that other nice man.” He says really getting into the girl role now.

“Well Benni Girl, Daddy will be glad to fuck that little boi pussy for you. But, you know what, Daddy likes cock sucking too. Does Benni Girl like cock sucking?” Now I am really getting into this myself and have reached into my pants to fondle my hot cock.

“Oh boy! Benni Girl loves to suck a nice hard Daddy cock. I will love to suck for you.” Benni says.

“No Benni Girl, Daddy wants to suck your cock too. Would you like that?” I confess.

“Oh yes, the other men never suck Benni Girls clitty for her. I would love it but want to do yours first. Will you come visit me, please, please, come see me all dressed up!” She says. Shit, now I’m thinking of him as a her! She is taking me somewhere really new and it is making me hot.

“When do you want this nastiness to happen?” I ask hoping for right now!

She tells me where she lives and I figure I can shower and be there in a couple of hours and she (I keep doing that!) says she will be ready.

Fuck it if someone wants to be identified as such I am fine with it.

We say our good byes and I am off to shower and shave. I shave everywhere expecting Benni to do the same.

When I arrive at the address in a nice apartment building,I knock trying not to make it sound like I am trying to take the door down and hear “Come in.”

Opening the door I see she is standing there with one tanned leg off to the side. Platform shoes, purple and pink stripped socks to mid-calf. Micro shorts with a prominent ball and cock bulge. Her balls bulge out in front and her cock looks pretty hard as it points off to the side. Bare mid-drift with a sequined black mini top. She has long straight brown hair that looks real. She must have had it tied back when we met at the beach.

She puts a hand on her out-thrust hip and says: “What do you think Daddy?”

“I think somebody is going to get fucked tonight! And sucked, maybe a couple of times. Come here sweetness.”

As she stepped to me I took her face into my hands and kissed her, wetly and with a lot of tongue. As I broke the kiss I looked at her and said: “I can’t believe this, you look so different and so fucking HOT. I am thinking about you as a girl, is that weird?”

“No Daddy, when I dress like this I am a girl. I’m your Benni Girl and will do anything you like. Tell me what you want me to do for you and I will be your slave.” She says.

“Well baby, the first thing I want is to take off those hot pants of yours so I can see that hard cock of yours.” I say as I search for the opening to her shorts.

She shows me a zipper on the side and tries to open them for me. I push her hands away and pull the zip down and spread her shorts open. She helps me lower them by wiggling her hips and looks so hot doing it. We have a little trouble getting them by her platforms but we both are on a mission and get it done. She has a pink bikini like bottom on but it is only big enough to contain her shaved balls. Her hard uncut cock is under the string to the side and very hard. I didn’t really get a good look at it at the beach and it is beautiful. She is fat, long and oozing juice. I fondle her foreskin and work it back and forth as I cup her balls.

“I can’t believe how hot you look baby! You look so feminine even with this beautiful cock. I cannot wait to feel it in my mouth.” I tell her.

She reaches to my belt and smoothly opens my pants and before I know it I am stepping out of them. I step out of my loafers easily as she moves to unbutton my shirt. I am glad I didn’t wear socks.

“Do you want me naked Daddy?” She asks.

“No my beauty I want you just like you are, just maybe somewhere more comfortable.” I say and she takes my hand and leads me to her bedroom.

It looks like any other young girls room all frills and pink with fresh flowers and candles. She steps out of her shoes and now is just a little shorter than me. We kiss softly as we both try to cover each other’s body with our hands.

She drops to her knees and takes my pulsing cock into her mouth. Before I know it she easily has half in her mouth and is running her tongue all over my length. Spit is flowing out from between her lips and covers my ball sack.

She breaks away to say breathlessly: “Oh daddy you have such a perfect cock. I need to do this before anything else. Please let me suck your wonderful man cock.”

Wanting it as much as she does but know I will not be able to stand long so try to move us to the bed. She quickly gets onto the bed but holds me standing next to it. Before I can say or do anything she is laying on her back with her head hanging over the edge.

“Fuck baby’s mouth Daddy, put your big cock in my mouth.” She moans reaching for my hips to bring me to her mouth. This is one of my favorite positions, either being sucked or doing the sucking and spread my legs around her face and present her my cock. I am pointing up at a 45 degree angle so my balls more easily find her mouth.

She sucks each of my balls working them over very nicely. This does nothing to slow the massive quantity of blood flowing through my cock. She wants my cock and has enough experience to know what to do.

She spins me around so I am facing the other way and pulls my ass cheeks open and lowers me to her mouth. Her tongue finds my ass hole easily with a familiarity of a long time lover. As she works my anus over I almost pass out and all I can do is moan: “Oh baby, eat Daddy’s hole for him.”

She is covering my ass hole and licking it very nicely. But she reaches up to find my cock, and like most guys, it has drooped some and she spins me around again and sucks my cock into her mouth.

“Baby, Daddy liked that, will you do it again?” I ask not knowing what I want now. My cock feels so perfect in her mouth and she made my ass feel so good, but as I look down her body I see her nice cock pointing straight up begging for my mouth.

I can feel my cock hardening and it is making it difficult for her to comfortably suck me so I lean forward to take her into my mouth. Now my cock and her mouth come together smoothly.

As I bury my face in her crotch swallowing her cock I smell and taste something I have never experienced in all the cocks I have sucked.


Over the last year and a half I have sucked and really enjoyed sucking a lot of cock. Many different and some a lot, but I have never tasted or smelled anything this nice.

Her balls are still cupped by the pouch she is wearing and I caress them as I suck her tasty cock.

She raises her ass pushing her cock to meet my mouth and reaches behind me to run her fingers down my ass crack to tease my anus again keeping me hot but not so hard that I still easily slide into her mouth and down her throat. She works my hips without removing her fingers from my crack to start a fucking motion of my hips to match hers.

We frantically get into a rhythm fucking and sucking each other. Still cupping her balls I pull back enough to suck her foreskin, running my tongue around her cock head while stroking her hard shaft with my free hand.

She is working me in and out of her mouth like one possessed. Before I know it I am shooting my load down her throat. Shot after knee quivering shot of hot man juice fills her mouth and she takes it lustfully, moaning all the time.

As my orgasm subsides I realize I have forgotten her cock and as I try to take her back into my mouth she moves out from under me and pulls me to the bed beside her.

“Baby, let me make you cum. You made Daddy feel so good; I want to do the same for you. Let me suck your beautiful boi cock.” I say as I reach for her.

“If you really want to make your baby cum, put it in my little boi pussy. Fuck me like you fucked your friend on the beach, except this time it will make me cum. I bet if you fuck me with that nice cock of yours I can cum without touching my little clitty.”

As I reach for her “clitty” I say: “If this is a clitty it is the biggest one I have ever seen and I would love to have it cum in my mouth.”

She moves so that I lose my grip on her clitty and we roll around gently wrestling. I easily pin her and have her struggling between my legs and the rubbing of my cock and balls starts making me hard again.

As I have her under my outstretched arms and legs she moves rubbing her thighs together and I feel her now very hard cock slip between my ball sack and leg. My cock and balls are sliding around her belly on our mixture of cock leakages.

I could get off again like this but when someone is begging me to fuck their ass when I have had to work so hard to get some women to try it, I am ready to please her.

“Roll over sweet cakes and let Daddy make love to your boi pussy.” I tell her.

She rolls over and pushes her sweet little ass up for me. She reaches back to move the string of her ball pouch out of the way exposing her ass hole to me. It glistened and looked like she had put pink lip gloss on it. As I leaned forward I could smell more cinnamon. As I kissed her anus I knew where the aroma came from, she had used some type of anal lube and was ready for me, but I wanted this ass and was going to eat me some before I pushed my cock into it.

“You are a nasty little slut aren’t you, all lubed up for Daddy’s cock. I bet you have a lot of experience getting cock don’t you my slut.” I tell her wanting to see her limits.

“Yes, Benni Girl is a real cock slut but yours is the one I have wanted the worst. Your juice tasted so good fill my boi pussy with it and make me yours. Fuck me daddy.”

I lean forward and stick my tongue into her ass hole and she opens right up. She taste like her scent and it excites me to know she is such a slut and wants me so wantonly.

As much as I want to eat her ass out I am surprised that my cock is so hard so quickly and as I raise up to place my cock head at her entrance I say to her: “Is this what you want my little sissy slut? You want this hard cock? Tell me bitch!”

“Oh please Daddy, give me that cock I want so bad. Give all of it, every inch until there isn’t any more. Oh Daddy fill me with your love.”

“Hold your pussy open for me.” I told her as I reached between her legs and pulled her now semi hard cock and balls back between her legs and holding her legs between mine I run my balls over her cock and ball sack. This rubs my cock head over her hot open anus. I am holding her in place but she can cause us to rub our genitals against each other’s. When my cock head runs across her ass hole she says: “Put your perfect cock in me and fuck my pussy Daddy.”

Not being able to wait any longer I angle my cock head to her ass hole and slip inside of her. I have fucked a lot of people in the ass lately but no one has been able to take half of my cock all at once. She easily takes it while tightening her colon squeezing my cock.

“You little cock slut. I can’t believe how easily you took that much cock. You are a tramp and I really love it. Here can you take all of me?” I ask as I push my cock slowly into her until our balls rub.

Her moans almost make me cum right then. I have never felt anything as nice as her ass feels right now. I don’t move I just hold onto her hips and relish the feel of my cock inside of her.

I reach for her hair and pull her face to mine, glad she isn’t wearing a wig and kiss her hotly forcing my tongue into her mouth. Force is an overstatement as she welcomes it and meets it with hers. We fuck each other’s mouth wildly.

“My little fuck bunny I have had my cock in a lot of pussies and more than a bunch of asses, male and female and I have never had my cock anywhere as heavenly as your boi pussy right now.”

I start rolling my hips fucking her ass as I tongue fuck her mouth. She reaches around to slide the fingers of one of her hands between my ass cheeks to find my ass hole and press her middle finger into me.

Always wanting more I say to her: “Baby I wish you had two more cocks. One to suck and another to fuck my ass while I am in yours.”

“You nasty man, you are a bigger slut than I am, but I bet I could find some for you.” She laughs. “Now fuck me properly.”

We fuck like this for a while but I want to make her cum before I do again and without pulling out of her roll her onto her back. She knows what I want and pulls her legs up spreading them and exposing her sexual center to me. I take her still semi hard cock into my hand and start to stroke her.

She starts to harden in my hand and I say to her: “That’s it my little slut, get that clitty big for Daddy, I want you to cum for me. Shoot your load everywhere so I can lick it up and taste your juice.”

This pushes her over the edge and she starts cumming while still only semi hard and I stroke her faster and faster until she slows. As she is cumming she is squeezing my cock in her ass and it brings me to the brink and I race over it and shoot my second load into her guts. This excites her and she starts cumming again before she has stopped cumming from the first time. This is a first for me, but one of so many today. I have cum so many times in so many ways and been with many men who have done a lot of cumming too, but never saw this before.

She has thrown her head back and has her eyes tightly closed as she pushes her ass to my cock. Silently begging for all I can give her.

We are lost in the intenseness of the moment. Her ass gripping me. My cock filling and fucking her and my hand stroking her cock.

We both are covered with the sweat of our coupling and I am overwhelmed by the immensity of the fuck. My senses are overwhelmed. Seeing this, the feelings in my cock and hand, hearing her cries of joy and the smell of her cum, my cum squirting out around my cock, our sweat and the change of sent in the lube. To complete the flood of stimulation of my senses I reach down to scoop up some of her cum and lick it off my fingers. As she feels me touch her belly she opens her eyes and sees me sucking up her cum.

“Oh Daddy, you are the nastiest man ever and the best lover I have ever had! I will never forget this moment. You make me feel like a complete girl.” She tells me as she wiggles her ass on my still hard cock.

Sensitive now my cock cannot take any more stimulus and I slowly pull out of her ass. I watch and love watching her ass work around my cock until I am free of her and she remains open for a moment before slowly closing. Almost immediately my man juice leaks out of her anus. I lean down to slurp up some of it and she pushes her butt into my face. I tongue fuck her boi pussy for a moment but am beat.

I roll to lay by her side and pull her into my arms and say quietly: “That was out of this world my little fuck toy.”

As she pulls the covers over us she snuggles under my arm and says: “Well maybe we can try for something more after a little nap…….

A time to wear a costume, Jerry uses Halloween as his excuse to dress as a woman.

Jerry loved October, his favorite month of the year, by far. The Fall was his favorite season, too. With the colorful array of leaves that crunched underfoot and the multi-colored canopy overhead, he loved the cool crisp air that made his nipples as hard as his cock. Whenever he went out for a stroll in the brisk October breeze to enjoy the Fall day, he enjoyed wearing women’s silk panties beneath his pants. The feel of the panty against his hairless skin was pure luxury and the freeing sensation of them helped him to pretend that he was completely dressed as a woman, even when he was dressed as a man. With every step he took, the feel of the soft material continually rubbed against the head of his cock helping to keep him hard.

It was fun being naughty without anyone knowing. Unless he was hit by a car, while crossing the street, no one would know, even suspect, that he was wearing women’s underwear. A man with a secret, a man wearing silk panties, it was his secret not to tell. Remembering what his mother used to tell him to always wear clean underwear, they may not be men’s boxer shorts, but at least they were clean, Mom.

Even though he was the youngest of three children, he grew up as the man of the house, after his Mom divorced his Dad. Jerry adored his mother. He loved his sisters. For him, cross dressing started so many years ago. Whenever his mother and sisters weren’t home, he had a complete wardrobe of their clothes to wear. He’s spent his teenage years serendipitously and stealthily sneaking around the house wearing his sisters’ and/or his mother’s clothes, whenever he was home alone. After his mother passed, he still cherishes a memory of wearing his mother’s panties to school on those days he didn’t have gym.

Now, living alone, after his marriage ended in divorce, too, he’s finally free to live his life in the way he wants to live it. Maybe it was the leaves turning colors, before falling to the ground, but he somehow viewed his life much in the same way. As if he was an artist using a kaleidoscope of color in his new, sexy makeover, as if he was a chameleon changing color to compliment its background, in his case from male to female, as if he was a circus clown with a different colorful costume for each skit, not that he was clownish in any way, although there’d be some who think him a clown or worse for having the incontrollable need to dress as a woman. Nonetheless, as if shedding his skin and transforming his persona in deference to his inner beauty, as a caterpillar metamorphosing into a beautiful butterfly, spreading his wings to allow his feminine spirit to soar, he changed from a man to a woman with the season.

“Viola! How do you like me now?”

The makeover from within, from inside out, instead of outward in, was dramatic and dynamic. He talked like a woman. He walked like a woman. Even without his hair, makeup, and clothes, one could see that he was a woman beneath the man. He looked like a woman.

Changing himself to become his wished for identity and his preferred for gender, it was no one’s business what he did in his private life; that was personal. He was outraged when men questioned him, made him feel bad, and pried into his private affairs, whenever suspecting he was a cross dresser. These were the same men who never should throw stones at their own glass houses, while going to great extremes to keep their personal business secret; he never understood the difference. Why should he confess his innermost secrets when they don’t share their dirty little secrets? We all have skeletons hiding in our closets, don’t we?

When those men, who laugh and point at him, divulge all the strip clubs they visit on their long, liquid lunch hours and all the extramarital affairs they have when they lie to their wives and tell them they were working late at the office, is when he’ll broadcast to everyone that he’s a cross dresser. Until that time, they could all go and fuck themselves. Yet, except for those who have seen him perform in drag, few know his secret that’s he’s a cross dresser.

Even though he was a cross dresser, when he was dressed as a woman, he didn’t feel that he was a man cross dressing to look like a woman. He truly felt like a woman. Because he was a small man, barely 5’7″ tall and nudging 140 pounds, his dimensions were closer to female than they were to male. All his friends were 6′ and taller and most weighed over 200 pounds. They all dwarfed Jerry, that is, until he did his hair up and wore his high heels. Then, he was spectacular.

As if readying for the prom, as if readying himself to attend a debutant ball, he spent weeks readying for the Halloween costume parties that he was invited to and excitingly attended each year. Recently paid to perform, Halloween costume parties not only served as his coming out party in his need to dress as a woman but also fulfilled his need to sing, dance, and entertain, all while making some extra money, enough to pay for his extravagant costumes. He’s even given more than a few one liners to some drunken bashers in the audience. This year, he had received invitations to three Halloween parties, a record number, one Friday night, one Saturday night, and befitting Halloween, this year, one on Sunday night, October 31st.

In previous years, the most Halloween parties he was ever invited to and attended were two and, in this tough economy, an expensive proposition to host with all the food and drink, he was surprised that people still celebrated Halloween with a party. Maybe because Halloween fell on a Sunday this year, with the full weekend to prepare for and to celebrate the holiday, people were more apt to take advantage of the holiday by having parties. Besides, a time of the year that darkness falls over celebrations and holidays and people start to contemplate and dread a long, cold winter, if it wasn’t for Halloween, other than birthdays and anniversaries, there’d be little to celebrate between Labor Day and Thanksgiving.

He wished for the time when he’d have multiple Halloween parties to attend in a day. Much like the Christmas season that starts the day after Thanksgiving and runs through to New Year, he wished Halloween had a prolonged season, too. Wishing he lived in Salem Massachusetts, where they festively celebrated Halloween every day the entire month of October by dressing up and walking around in costume in public, maybe he’d take a vacation there next year.

Then, he thought of Elvira, Mistress of the Dark. Boy, if she wasn’t a woman, she’d make for a great cross dresser. The first time he saw her, he thought she was a cross dresser. She had her year round, Halloween spook movie night. Also, playing year round Halloween costume dress up, there were the fictional freaky Munsters and the Addams Family of television and movie fame. He yearned for a place and a time where he could live as a women every day. Wow, he’d finally be free. He’d finally be at peace. Finally, he’d be who he was always meant to be.

Even though dressing as a woman wasn’t Halloween scary, albeit maybe it was to some, he thought, while laughing to himself, he wondered how he could make more use of the Halloween holiday to his personal advantage. As an entertainer, a singer, a dancer, and an amateur comedian, he wondered if he could make a year round business out of attending or throwing Halloween parties. When the holiday was more about wearing a costume, why must Halloween only be on October 31st? If it was up to him, Halloween would be every day. With Halloween his pretense and his reason for him to play dress up and cross dress, he loved dressing as a woman.

Halloween was the one time of the year that he could be the woman he always wanted to be without feeling self-consciously uncomfortable and guilty. As far as most people were concerned when they saw him, he wasn’t as much in drag, as he was in Halloween costume. As far as he was concerned, he was the woman he always wanted to be, while still being the man that he’ll always be beneath the clothes, the hair, and the makeup.

“Trick or treat.”

Halloween was his special holiday and his special day that he didn’t feel the embarrassment and the shame that he always felt before, when he hid his need to cross dress by hiding in his house. Finally, brave enough to go outside, whenever he ventured out of the house dressed as a woman, he spent more time feeling conspicuous and feeling like the monster that he wasn’t than he did enjoying his moment, as the woman he always wanted to be. His excuse and his reason, should he bump into someone he knew, a friend, an acquaintance, or a relative, whether they were dressed up as ghost, a hobo, a witch, or a goblin, was that he was going to or coming from a Halloween party. Halloween was the day we all dress up as someone or something else, anyway, and it was the day that he dressed up as a sexy and desirable women.

Even though dressing as a woman was a charade, he was tired of the charade. He wished he didn’t have to hide behind Halloween, as his pretense to be himself and who he truly was, a woman trapped in a man’s body. He envied women and wished he could dress as a woman all the time, and not only when in costume on Halloween. For the sake of others having something to say about what he did and when he did it, it wasn’t fair that he was so tortured and unable to live his life the way he wanted to live it without having to endure all the stares and acrimony.

Yeah, sure, he could say fuck them, but the question was, did he believe it and the truth was that he didn’t because he spent more time being too preoccupied, consumed, and concerned with the perception that other people had of him. Why was that? Why should he give a care about them and how they felt, when they didn’t give a care about him and how he felt?

Maybe that was the reason why he was so endeared to certain female celebrities, who really could say fuck you and mean it, Bette Midler, Cher, and Madonna, immediately sprung to mind, along with Christina Aguilera and Lady Gaga. They all danced to a different drummer and they all stayed true to themselves. Truly, they didn’t care what others thought of them. They needed to be who they were and they did. Because of those women is why he’s the man that he is by becoming the woman that he so needs to be.

“Fuck them!” There, he felt better saying it and meaning it. “Fuck them! Fuck them! Fuck them! Who the fuck do they think they are? This is my fucking life. Fuck them!”

Wow. Save the anger, hold it, and then let it go. Even though it’s there, always there, just beneath the surface, he finally felt free. Free to live his life the way he wanted to live it and to do whatever he wanted to do.

“Yeah, baby!”

He loved wearing sexy under things, bras, panties, slips, corsets, stockings, girdles, and garters beneath his clothes. His dead giveaway that he was a man dressed as a woman, besides his Adam’s apple, was that he dressed better than and, if he’d say so himself, looked better than most women his age. Most women don’t know how to put on makeup. Generally, in two groups, those how put on too much and don’t who don’t put on enough.

Most women don’t know how to make the most of what they have. He did, of course, not having any female body parts, what he could do with makeup was artistically amazing. Most women his age, more comfortable in jeans, sneakers, and a sweatshirt, give up and, unless they have money, no longer take the time and the expense to properly care for themselves. He put those women in a non-gender category. Dressing more like men than they dress as woman, when wearing jeans and a sweatshirt, unless it’s a tight sweatshirt and the woman has big tits, that sloppy attire does nothing for their sensuality, sexuality, and femininity.

More comfortable with applying makeup than he was with applying quick set cement for a building project in his backyard that he doesn’t want to do and keeps procrastinating doing, he loved dressing as a woman. He loved doing his hair, a wig actually, and doing his nails and makeup. He didn’t even mind so much shaving all the hair off his trim and fit 5’7″ body, that is, except for all the itching, when it all started growing back the very next day. If he was really a woman and had estrogen instead of testosterone, he wouldn’t have to shave all the places that he shaves now. He could only imagine the time he’d save.

As if shopping for Christmas gifts for others, he spent the entire month of October shopping for the right outfits for the Halloween parties he’d attend. Shoes were important. It was always difficult finding a shoe wide enough and comfortable enough to wear. Always, he’d have to jury rig it somehow to expand the width and find a softer pad to put inside as a cushion. Still, he couldn’t wait to go shopping. He hasn’t been this excited since he was asked to perform in front of a live audience dressed as Cher.

He always wanted to sing, but he never had the talent or the voice. Yet, he had a knack and the ear for impersonating the voices of others. Weird. Just as weird that he could impersonate the voices of others, it was weird that he was unable to find and develop his own singing voice. Always he was deemed a better singer than he was, when he copied the sound of someone else.

That first night at the karaoke bar, after he found the courage to perform with more than a few drinks giving him the who cares attitude, his friends thought it was a joke and that he was kidding when he told them that he could sing just like Cher, that is, until they heard him sing. Then, every time they’d go to the karaoke bar to drink, they’d pressure him to get up on stage and sing. Always, he stunned the crowd. Always, he received the biggest round of applause and for the rest of the evening, he didn’t have to buy another drink. People continued coming to his table buying him drinks and asking him to sing this song or that song, as that singer or another.

“Jerry, you sound just like Cher, better than Cher. It’s unbelievable. If I close my eyes, I’d think you were her. Do Bette Midler.”

Only, for him, it wasn’t the same show visually and he didn’t derive the same pleasure from doing his female singing impersonations, unless he dressed up as the person he was impersonating. Even then, especially then, he’d never felt comfortable enough to dress up as a female impersonator and impersonating a celebrity in front of his friends. Without doubt, even though he’s a straight man, loves women, and never even contemplated having sex with a man, his friends would think him gay. They just don’t get it. They just don’t understand. It’s hard being friends with someone, who really doesn’t know who you are. Certainly, he was tired, so very tired, of pretending to be who he wasn’t.

It’s bad enough they joked around with him calling him a female impersonator and a drag queen, if only they knew his secret. If they only knew that he was. If they only knew he loved cross dressing. Fearing that he’d want to have sex with him, clueless and ignorant, they had no idea.

If they only knew he wished he were born a woman. If only they knew he was wearing silk panties beneath his pants and a nightgown to bed every night, they’d be his ex-friends, instead of his friends. His real friends were other cross dressers. They knew what it was to have that incontrollable need to dress as a woman and what it felt like to have that overwhelming feeling of being so pretty when they did.

Nonetheless, he wasn’t committed enough to becoming a woman by having a sex change operation. He liked his penis and having sex with women too much, and a sex change operation was a step that he was unwilling to take. Besides, he wasn’t gay and wasn’t looking to have sex with men. As much as he loved dressing as a woman, he loved women too much, which is why, perhaps, he impersonated them so well.

For sure, he never wanted to have sex with a man. He wouldn’t mind having breast implants, though. That would be cool to have his own breasts instead of having to wear a padded bra with silicon falsies. He could only imagine the pleasure he’d feel jerking off, while feeling his own tits. Also, it would make him happy to take just enough female hormones so that he wouldn’t have to shave as much hair, as often as he must shave it off his hairy body. The preparation for his male to female transformation was the real time consuming pain in the ass.

It’s funny how most of the women he could impersonate went by one name. Beginning to build quite the repertoire, he had a list of women he could do, Cher, Streisand, Celine, Madonna, Christina, Aretha, Whitney, Mariah, Shania, and Beyonce. Then, there were the more recent female singers, Bette Midler, Lady Gaga, Carrie Underwood, Dolly Parton, and Taylor Swift. Yet, Britney, because of her sexy antics and in the sexy way she dressed, was the most outrageous fun. Dressing up like her with a short skirt and pigtails, while dancing around the stage, was always a good time. He felt the most like a woman, when doing her.

A celebrity impersonator, who used impersonating celebrities to cover his cross dressing, it was his way to feel free. Yet, confined to the month of October and mostly to Halloween, his freedom was short-lived, which is why he loved October and which is why he loved Halloween parties.

It had all started innocently enough. At the Pro-Biotics regional office the crew always launched a rather rowdy Halloween party with loads of alcohol and “medicinal” marijuana. Steven always enjoyed the festivities even though he wasn’t old enough to drink yet.

‘Just one more year,’ he thought, ‘and then I’ll be able to party with the rest of them.’

For a rather boring old office environment, there were loads of nice people who were all entertaining in their own right. Jessica was the office hotty with a nice round rump and long dark hair. Ben was Steven’s best friend, another intern who was a year older than Steven and would be enjoying the booze for the first time at the party. Ben was a little taller than Steven and broader of shoulder, a guy who spent time in the gym but not a complete muscle head. Their boss Eric was a fair man who explained their duties clearly and had proper expectations of what they should and should not be doing as interns. And then there was Stephanie, the office slut. About the same height as Steven but with and amazing rack and long blonde hair, She’d pretty much slept with all the single guys in the office (and even some of the married ones), but she had a thing against sleeping with interns, which pretty much left Steven and Ben hung out to dry when it came to getting any from her.

The boys were always trying to one up each other, and the Halloween party wasn’t going to be any different. Both had been boasting about their costumes for weeks, and tonight was the night of the great unveil.

That is, it would have been if Steven hadn’t been late for the party by about 2 hours. Really, it wasn’t his fault, he just didn’t know his costume would take so long to put on. Going for realism over laughs, Steven had dressed up like Stephanie, including super slutty mini-skirt, loose sexy white blouse and red lipstick. What he didn’t know was how creepy it looked without shaving his chest and legs first, which ate up a lot of time at home. He had to borrow the panties from his sister, which was another level of weirdness. But Steven was willing to go the extra length for a joke. He was just hoping his costume would be better than Ben’s.

Entering the office earned him a lot of wolf calls from his co-workers, most of which were doing so because they thought he was actually Stephanie. He’d never realized it but he and her had very similar builds. Her hips were larger than his, and of course she had tits, but with the skirt on and the fake silicone breasts implants in the bra (something he borrowed from his dad’s home office, a plastic surgeon by trade) he was able to be a fairly accurate double for the office bicycle.

After passing the front desk Steven entered the main floor of the office where all the cubicles were. There people were already fairly plastered as they drank and flirted back and forth with each other, feeling more free and rambunctious than ever. People were dressed in all manner of costumes, from The Hulk, to Edward from Twilight, to a woman in all body paint with a few key pieces of scales placed in various locations to keep her modest. He loved it when someone did Mystique.

Steven lingered around the punch bowl, wishing he could partake, and had to keep some drunken hands off him from the more slobbered of his co-workers. It was embarrassing and flattering all the same time, and Steven felt more than awkward with all the attention. If it was some ladies flirting with him, that would be one thing, but all the attention was from other men, which was odd and confusing to Steven all at the same time. He couldn’t look that much like Stephanie, could he?

“Hey there sexy, need some saving from a real barbarian?” Came a husky voice from behind Steven.

He turned around slowly, already knowing who the voice belonged to. Ben stood there in a leather cod piece with a broad sword strapped to his back, bracers on his arms, and a leather bandana on his brow. Normally this would look campy on anyone else, but apparently Ben had been spending more time in the gym to really make the image look authentic. Muscles bulged all around his body, with veins lingering under the skin revealing how low his body fat was. It was intimidating to say the least, but also very impressive. Steven found himself blushing slightly having never seen his friend like this before.

“What makes you think I need saving from a half naked man?” Steven responded in his best Stephanie voice. It wasn’t extremely feminine, but Ben already looked fairly plastered so it would probably work on him.

“You need saving from my pal Steven, who would like nothing but to get in your panties…” Ben slightly slurred and he leaned over Steven.

Smiling to himself, Steven decided to take this game a little further, just so he could really embarrass Ben later.

“Oh, and you’re saying you don’t want in my panties?” Steven teased.

“I’m just saying I’m willing to earn it is all.” Ben cooed, the booze thick on his breath.

“Oh I’m sure Steven would be willing to earn it as well.” Steven teased his friend, finding it funny that Ben still hadn’t figured it out.

“Yeah, but Steven isn’t packing 9 thick inches beneath his cod-piece.” Ben whispered into Steven’s ear, sending shivers down his spine. Steven had always been proud of his 7 inch cock, but if Ben really had a 9 incher then that truly put him to shame.

“Men always say their packing 9 inches, but few rarely prove it.” Steven purred nervously. He was worried he might have been taking this a little too far, but he felt a need to see if his friend really had such a large cock.

“Tell you what gorgeous, I’ll prove it to you if you promise to help finish it off once it’s nice and hard for you.” Ben whispered further in Steven’s ear while playing with the small of her back. The situation was starting to become more and more confusing to her, and Steven’s felt her reactions shift and Ben became more lustful for her.

“We’re in the middle of a crowded party, you gonna just whip it out here hot stuff?” Stephanie…Steven teased, thinking his buddy was out of options for a private location.

“I just so happen to have a key Mary’s office. No windows on the door or any of the walls, and she’s been out on maternity leave for a month now.” Ben revealed with a smirk, already grabbing Stephanie’s hand and leading her through the crowd.

This was getting out of hand Steven though, his cheeks fully flushed, his mini skirt tenting as his obvious excitement. It was also obvious that Ben meant business as his cod piece was having a more and more difficult time keeping him contained. Steven thought he should pull his hand away and reveal to Ben that he wasn’t Stephanie, but something inside him stopped him from doing that. Instead, he just followed his muscled friend through the back offices until he reached a corner one. Pull the keys out of a leather pouch that hung to his side, Ben swiftly opened the door and led Steven in, closing it quietly and locking the door. Suddenly the music died a mere hum along with the laughter and hollering of the party.

“There we go, alone at last.” Ben said strongly with a wicked smile on his face.

“Yes, alone. Just you…and me.” Steven continued, trying to think fast.

Ben slowly untied his belt and dropped the sword tied to his back. Unfastening various belts and buckles, eventually Ben dropped the cod piece to the ground, revealing a semi-rigid cock pulsing beneath. Steven gasped slightly and sub-consciously licked his red lips. He thought Ben might have been exaggerating about the size of his member, but it wasn’t even hard yet and Steven was willing to bet it would be larger than 9 inches. It was evenly thick, growing larger with each second, the hair trimmed short and Ben’s large balls hanging low. Steven was surprised the cod piece was able to keep all that man-meat in to be honest.

“What do you think honey, nice and large isn’t it?” Ben said proudly.

Steven licked his lips again, and gulped slightly. “I don’t know, it seems awfully…flaccid.” Steven teased, preparing to drop the facade any moment.

Then Ben did something that shocked Steven more. He gripped his cock in one hand, and started stroking himself in front of her, growing thicker and larger with each stroke.

“Oh it gets bigger baby, trust me. Want to look at it a different way?” Ben asked in a very husky and lustful tone.

Steven could only nod, feeling herself weak in her legs.

“Get on the ground babe, on your knees.” Ben almost commanded. What was even more odd was Steven almost instantly obeyed, getting on her knees before her best friend. Ben walked forward and stood over her, stroking his now fully erect 9.5 inch cock above her face.

“Lick my shaft babe.” Ben commanded again.

It was now or never, Steven could either be Stephanie, the office slut, or he could be Ben’s best friend and let him in on the goof.

In answer to her own question, Stephanie stuck her tongue out and licked the salty balls handing between Ben’s legs. She engulfed them into her mouth and rolled them around, feeling their size and weight with her tongue. It was her first time sucking balls, having never thought she’d ever do it before, but Stephanie found she loved the taste of Ben’s balls in her mouth. Ben continued to jack himself off and moaned heavily as he felt Stephanie take him in her mouth.

She continued to lick up his shaft and town the crown of his cock into her mouth, sucking him deeply and loudly. Stephanie sucked Ben like she’d want someone to suck her cock, slowly and with lots of saliva, avoiding teeth and going down as deep as possible, which was difficult with Ben’s huge cock.

“Oh damn, I heard you gave good head, but I had no idea.” Ben moaned, his hips rocking slowly into Stephanie’s mouth.

Stephanie started rolling Ben’s balls around in her hand while sucking his engorged member, trying to stuff as much of Ben’s cock into her wanting mouth as she could. Stephanie felt Ben’s hands running through her wig, giving her worry that he’d find out she was an imposter, but instead Ben just pushed on the back of her head trying to force more of his cock down her throat. She gagged loudly, having to pull away to catch her breath momentarily, but once she had recovered she engulfed his cock again, like it was as important to her as air.

Stephanie had a maze of questions running through her head, having given into a desire she never knew existed in her. She was on her knees, feeling extremely feminine and having her mouth used a fuck hole by her best friend. What had started as a joke had taken a very odd turn to say the least, and the oddest part of all was how much Stephanie was loving it. Her cock strained against her panties, causing her skirt to tent, but luckily Ben’s attention wasn’t there…yet.

Ben continued to push her head on his cock, riding her face like he would her non-existent pussy. Maybe he’d be happy enough with a blowjob and once he blew his load in her mouth, they’d stop and Stephanie could run away and figure out what to do next. But just the thought of swallowing Ben’s load sent shivers up her back again, causing her to moan loudly into Ben’s dick as it rubbing back and forth against the back of her throat.

“Oh yeah baby, you are something special, I need to be inside more of you.” Ben said hungrily, popping his drenched cock out of her mouth. He lifted her up and forcefully bent her over the ouch, tugging her panties down and spreading her ass.

It was all happening so fast that Stephanie hardly had time to even properly freak out about Ben finding out that Stephanie was actually Steven. She had her ass cheeks exposed, her head pressed into the pillows of the couch in Mary’s office. Stephanie started trying to lean up and get out of the shameful position she found herself in, when suddenly she felt Ben’s wet tongue pressed against her asshole. She moan loudly and lustfully, displaying how much of a whore she really was as she ground his ass against Ben’s face while he rimmed her properly. She didn’t think it could get any better until she felt a hand wrap around her engorged cock and begin jerking her off while her asshole was eaten.

“Holy crap! Ben, do you know I’m Steven?!” Stephanie asked in exclamation while still maintaining her Stephanie voice.

“I knew when I first saw you, but that doesn’t change how fucking sexy you look. Does this mean you don’t want me to fuck you.” Ben responded quickly, disturbing his ass eating for a moment while he continued to jerk her off.

Stephanie continued to moan in deep pleasure, pressing her ass against Ben’s face. Finally, in a low and erotic tone she whispered “Fuck me Ben, take my cherry…”

That was all it took and Ben stood up and took position behind Stephanie. He spit on his cock and rubbed the saliva into Stephanie’s rosebud hole. For her part Stephanie was equal parts scared and excited, not sure if she could survive a proper fucking by Ben’s huge cock. She still wasn’t completely over the fact that Ben knew she was Steven the entire time, but the cock pressed against her asshole was pushing those concerns out quickly as she felt Ben start to enter her.

His cock head felt enormous as Stephanie felt her hole expand to fit Ben’s crown. She breathed slowly and steadily, biting her lower lip and gripping the couch tightly as Ben eased into Stephanie slowly. After he was about two inches in, Ben stopped pressing into her ass and just let his cock rest in her shallow opening. Stephanie was about to protest, wanting to feel more of his girth inside her, but Ben just stroked her ass affectionately, indicating that this was for her own good. She needed to relax and accept him inside her before he could continue.

Focusing on her breathing again, Stephanie took a moment to really enjoy how wonderful it felt to have her asshole stretched out by her best friend. She never could have imagined tonight would have led to this, nor did she want it to mere hours ago, but now that it did she realized that somewhere deep down inside she’d always wanted this. It was just something she couldn’t have ever openly admitted to herself. Maybe that was the real reason she dressed up as Stephanie, not to play a joke but to be who she always wanted to be. A cock hungry whore with her best friend’s dick plunger deeper into her asshole. Stephanie perked up, feeling Ben’s renewed movements behind her. He roughly grabbed her hips and pulled her ass back, forcing more of his cock into her ass.

This was the final stretch, so to speak, as Ben plunged the rest of his 9.5 inches all the way into Stephanie’s ass. Her eyes went wide and her cock jumped up as the crown of Ben’s cock rubbed her prostate. Each stroke Ben took into her rubbed her prostate more and more, keeping her erection hard and bringing to light new pleasures she’d never experienced before.

And before she knew it, Ben was entirely inside her, his balls resting firmly on her ass cheeks. Once all of Ben had been shoved deep inside her, he started fucking her with a slowly and purposeful stroke, make sure she felt each inch of his cock pull out of her and then invade her all over again. Each time his cock pushed back in it rubbed lovingly against her prostate, forcing pre-cum to ooze out of her cock and stain her panties. But she didn’t care at all and just sat there, ass high in the air, enjoying the feeling of being well fucked by her horse-hung friend.

Suddenly Ben slapped her ass as he fucked her hard, causing Stephanie to jump a little and moan out loud again, revealing her true slutty nature even more.

“Is this what you’ve been wanting, your best friend to fuck your slutty ass?” Ben asked, his voice full of sexual hunger.

“…yes…” Stephanie managed weakly.

“Yes what?” Ben asked, slapping her ass again.

“…yes, sir.” Stephanie answered, starting to realize just how the dynamics of their relationship were shifting.

“Do you like the feel of a huge cock rubbing inside your asshole slut?” Ben demanded to know with a slap of her other ass cheek.

“Yes, sir, I love the feeling of your cock inside me.” Stephanie explained with a moan, as Ben sharply slammed his cock into her again.

“Do you me to breed you slut?” Ben asked, humping her fast and with more purpose.

The question confused her at first, but then she realized what he meant. “Oh god yes please, spill your seed inside me. Make me a true slut and cum in me with your unprotected cock.” Stephanie truly begged from her new master.

That was all Ben could take and he drove his cock back into her hole one final time before it erupted inside her, cum pouring out of him in waves of sexual delight. The last plunge pushed Stephanie over her limits as well, rubbing her prostate just the right way to cause her to cum also, filling her panties with her seed. Together they bucked and rubbed their bodies together as their sexual highs peeked. And just as fast as they climaxed, they came down and realty sunk in.

Ben had his cock shoved up his best friend’s ass who was dressed up to the nine’s looking a lot like the resident office slut. Steven was bent over the couch, ass spread wide open with Ben’s cock buried deep inside him, his asshole and his panties soaked in cum. The two start to untangle from each other and Ben sat on the leather chair across from the sofa while Steven gingerly sat down on the couch, his rear a little sore from the recent attention.

“Well that was…unexpected.” Ben admitted with a blush.

“So you knew it was me the entire time?” Steven asked, shock returning to his system.

“Well yeah, I already saw and got shot down by the real Stephanie an hour ago. She dressed up as a cheerleader, how unoriginal.” Ben admitted with a roll of his eyes.

“And despite knowing it was me, you continued to flirt, then fuck me?” Steven continued.

“You seemed to rather enjoy it.” Ben returned with a smirk.

Steven blushed, returning momentarily to Stephanie mode. “Well yeah, I wasn’t expecting that I would, but you just took charge and you knew what you wanted, and what you wanted was me. That’s powerfully erotic.” Steven explained, his cheeks crimson.

“And what if I want is still you?” Ben asked, his eyes dark and his tone heavy.

Steven blushed deeply again, squirming in his seat.

“Come here slut, and sit on my lap.” Ben commanded in a tone Stephanie couldn’t resist.

Steven may have sat on the couch, but Stephanie was the one who rose from it and walked to across to the chair Ben was recliner on. She straddled him and lowered her still exposed ass onto his recovering cock, letting it slide past her cheeks and press back into her. She moaned heavily and held onto Ben’s shoulders as she forced herself down onto his cock more.

Then Ben did the truly unexpected. He reached up and pulled her head down to kiss her deeply and passionately. His tongue forced its way into her mouth and rolled around her own tongue, invading her much the same way he invaded her earlier. She groaned heavily into his mouth, enjoying him taking her forcefully again and she ran her hands along his muscled body, delighting in how feminine she felt and how masculine he felt.

Ben broke the kiss and looked her deep in her eyes as he started fucking her again, his cock now fully erect again. “I think Stephanie and I need to hang out a lot more from now on.” He announced boldly.

Stephanie just grinned and moaned again as she felt his cock plunge back into her. “I think so too…master.”

September 2018
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