Shemales Porn Stories
Page 80

3 Teen Cross Dressers Misadventure - Part 3 Final

I was with two of them on the bed. One of them spread my legs and began to rub his cock up and down my stockings, I could feel him growing hard. The other sat over my chest and told me to open my pretty mouth. I did but no way could I take it all, he must have been around 8". He shoved his cock into my mouth and down my throat thrusting as I gagged. Although I couldn't see, I heard pleasurable moaning from the man on the bed with Sean. Craig, on the couch with Brett said "I’m gonna screw that pretty little hole of yours and make you scream like the bitch you are." No words came from his mouth,... Continue»
Posted by ClaireCD 4 years ago  |  Categories: Hardcore, Shemales, Taboo  |  
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The ConVentioN part

2. Arrival
Pulling against the chains that secured her arms over her head, Sasha whimpered in frustraition
yet again. Her bonds hardly rattled at all as she shook and twisted her body to try and get free.
All she succeeded in doing though was making her heavy tits jiggle and bounce painfully. Alone
and naked save for the few cow patterned garments her mistress had allowed her, Sasha cried
softly in the darkened room. Her breasts were swollen with milk, now each one was larger than
her head! Pink bands had been tied to the base of her nipples, preventing any of her milk from
leaking out.... Continue»
Posted by peterbtrs 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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First Time By Transsexual

When I was 21, I spent a summer in a southern city doing a service project. I was engaged to a girl and excited about marriage, but I was also extremely curious about the male body. I was one of those k**s that masturbated constantly, and almost always about sex with a man or a transsexual. The summer before my senior year, I was down in this southern city living completely on my own for the first time. Since I was doing a service project, I only got one night a week off. I wasn't sure what to do with that night since I didn't know anyone, so I decided to get d***k. Several times, I just went ... Continue»
Posted by kbking64 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Gay Roommate crossdress

I have been cross-dressing since I was 7, always been a bit in the closet about my homosexuality and cross-dressing but I have always loved it and kept it close.

I had one roommate when I was living in Boston his name was James. he was a pretty good looking guy who seemed to always be doing well with the ladies and I always secretly watched him as he paraded around the apartment in his underwear always hoping one day he'd notice m little did I know he already had.

it was a typical Saturday morning I had gotten up and said hi to James on my way out for a jog, went out the door and st... Continue»
Posted by alex_boycd 4 years ago  |  Categories: Gay Male, Shemales  |  
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Boy gets Fucked by Shemale

This is the story of my first she male. I had always been curious about dicks. I had always been attracted to women and I loved to watch a woman get pounded by a big cock. But after awhile I realized that when I tried to imagine the porno, I always imagined myself in place of the girl. One day, when I was sixteen, I decided to see what it felt like to be a girl. I had never tried anal before (I could never bring it up to my girlfriend) but I knew I had to try something. So I gathered all the necessary tools and went into my room. I locked my door so my mom wouldn't accidentally walk in on me a... Continue»
Posted by ClassicCockx 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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Str8 Guy Seduced By A Tranny (ch1)

Str8 Guy Seduced By A Tranny (ch1)

For a str8 friend here at xHamster... who is a fan of my writing and when I told him I would write a story with him in it... I'm not sure he knew what he was getting into..

Chapter 1

~~~~~~~~~~~~~~~~~~~~~~~~~

To say I was nervous was a bit of an understatement... but I was also very, very excited. This was my first time putting it out there in a big way.

Back home, I had gone out a few times and was completely passable... I guess I should explain more...

I am Lexi, that is my girl name... I was born a boy, or I should say... Continue»
Posted by TomStone90045 4 years ago  |  Categories: First Time, Shemales, Taboo  |  
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Another time Another Place Finale

A NIGHT OUT

A taxi was waiting outside. I was ushered by Richard towards the rear door and he hissed, “Don’t forget you are a girl now Charlotte and you should have been taught how to get into a taxi” In a haze of nervousness I did as I had been told. I tried to follow Renata’s instructions but it was not so easy with a real car. Richard got in the other side and issued some instructions to the driver about the centre of Roma.

He sat close to me and was holding my hand down close to my left leg with my other hand I tried to pull my dress down but still there was a huge expanse of silk... Continue»
Posted by charlottekerscot 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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Willows transformation 1


Fern and I had been married for three years. Our sex life had become bland, routine, and, frankly, I preferred masturbation to the work it took to cum by intercourse. I was pretty sure that Fern felt that way, too. You see, my cock is, at best, 5 inches. My touch, or my tongue, on her clit seemed to be much better received than my cock inside her.

I've always been a cross dresser. I can remember being in first grade and wearing my older s****r's clothes and pretending I was on a date with a boy. Before we married I told Fern about this. She treated it as something that would go away once ... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Adult Bookstore Dancer

Adult Bookstore Fun
At one time there were eight adult books in my city now there is only one. Makes me very sad as I loved dressing up like a twenty-five cent whore and visiting them on the weekends. I think I enjoy all the humiliating comments and condescending looks the customers would make about me in the front as much as I did sucking off cum filled cocks in the mini booths in the back.
One of stores had girls working in the front that would give you a privet dance, for a fee, in one of the many privet room available. I meant Ida there. I was in drab and looking at the BDSM magazine... Continue»
Posted by littleoralvee 3 years ago  |  Categories: Shemales  |  
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How I became a GURL part II

So I'm in college now, I've learned to love and use porn in all its forms, I've learned to be a great cock sucker and to have my ass fucked. I've learned to tie myself up -- as best as possible -- to pee all over myself to get that humiliating feeling. I'd spread the porn mags all over the floor and spend the entire night playing, trying to shoot my cum onto a photo of a cock so that I could lick it up.

The feeling of release whenever I gave in to all of those instincts was fantastic!

I loved cock! But I was a horny 20 something and still chasing pussy. Eventually the girlfriends star... Continue»
Posted by jenn1 3 years ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
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cross dressed cocks

I was looking forward to the fun I could have in my own place. I spent some time on the male chat line looking for someone to play with. he to liked to dress but like me was not at all passable . when he showed up at my place he hade on black thigh highs open toe heels and a corset ,he was taller then me and of average build . it was the bulge in his panties i was interested in. I was dressed in pink thigh highs red strappy heels pink panties and a light purple chemise with a pink bra under it.

we sat on the couch watching some porn he took out his semi erect cock and told me he wanted to s... Continue»
Posted by amitokinki 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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My sister, my first, the tranny

A little something different to spice up your lives

*******************************************************************************************************************************************************************************************

It was the first week of June and school was out for the summer, I was 18 and had just finished my senior year. One night while we were eating dinner, My Mom and step dad informed me that they were going away for two weeks. When they got married they did not go on a honeymoon, so they wanted to take one now. Jack, my stepdad, told me they were going to... Continue»
Posted by 6270daniel 1 year ago  |  Categories: First Time, Shemales, Taboo  |  
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Fooled by a tranny

When I was 19 y/o and in the military I took a 2,000 mile motorcycle trip from my base to my home on the West Coast. Bad weather made me stop for a few days near Nashville, Tennessee, and I decided to go bar hopping. I ended up in a rather dark and smokey bar where there was a very bad four-person band, but it gave me a chance to have a few beers and dance with a couple of women. Shortly before closing a young lady came into the bar who was beautiful. She was short, a bit under 5', and very petite.She had very small breasts, which I like, and her mini skirt showed she had shapely legs, and... Continue»
Posted by 1kaboom1 29 days ago  |  Categories: Shemales, Taboo  |  
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Ladyboy Secrets

LADYBOY DIARY
by utubeslut

forgive the misspellings but inocent words get sensored
by the auto censeless

Diaries can be dangerous and have unexpected
consequences if they fall into the wrong hands.
Or the right hands ….


Early Spring and that meant a visit from my
Aunt Becky and my cousin Susie.
I loved Susie but she was kinda weird.
She had mood swings like she had permanent
PMS, very unpredictable.
Otherwise she was very sweet.
Crazy bitch.

The neighborhood girls were drawn to Susie
like a magnet. Crazy peop
... Continue»
Posted by Utubeslut 3 years ago  |  Categories: Lesbian Sex, Shemales, Voyeur  |  
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The Arrangement





My wife and I have been married for 10 years and are very much in love but we do have our own little fantasies as we have learned over the years. She is 5'8" tall, blonde hair blue eyes, in my mind, quite a sexy body, with great legs, a nice ass, and ample breasts. She really looks pretty hot.......when she wants to. As for, me I am 5'10" about 165-170 lbs, and as her I have blonde hair and blue eyes. I have a fairly nice build, having been a collegiate athlete and still in ok shape.

That being said let me set the scene for what has taken place in our lives. Early in our marriage w... Continue»
Posted by lonicd 2 years ago  |  Categories: Fetish, Shemales  |  
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Tranny Gas Station Attendant

This happened about ten years ago and I thought I'd share it with you all for your enjoyment and mine! Like I've said before, although I'm bi-sexual, I don't walk around checking out other guys, nor do I like to be intimate with one. Sure, some might consider taking a cock in the mouth or ass intimate, but I consider it just sex. When I say I'm not intimate with other guys, I mean I don't kiss or cuddle or anything like that. It's always just sex, with no strings attached.......usually! There are exceptions to any rule, and this experience is one of them!

... Continue»
Posted by panteeluvr 4 years ago  |  Categories: Shemales  |  
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The Making of a Gloryhole Gurl Part 3

Making of a Gloryhole Gurl! Part 3
By Kristy

I look back on some of the Pictures from my early days, going to the Adult Bookstores and the Park and can’t believe how bad badly I was at putting my makeup on and some of the things I wore. Although I still like to dress slutty!
I could sneak away for only so long before I had to change back and make it home without a trace. I made a major breakthrough soon and began going into the bookstores completely dressed and I was going more and more to the ABS’s and sucking as many cocks as their were, and if I got real lucky I would fi... Continue»
Posted by kristygurl 4 years ago  |  Categories: Shemales  |  
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tranny hooker ( UK GUY SEEKING CONVINCING TV &

I was out late looking for a cheap hooker with £15 in my wallet I should at least get a blowjob. After 20 minutes of searching I see a young girl stood on the corner. I pull up along side her she tall long legs short skirt stockings m holdups long dark hair as she bends down I tell her how much for a bj. For u darling £10 for everything I m more than happy with that. Once in the car she tells me to drive down the road and take 2nd left. We end up down a dark alley at the end a quite car park. Once there I turn off the car she opens her legs grabs my hand and slides it down the inside of her th... Continue»
Posted by crbigboy 3 years ago  |  Categories: Fetish, First Time, Shemales  |  
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me and connor say goodbye..

Connor and i were f***ed to separate some time ago due to his f****y moving for work. he never specified where but when he told me this we only had a few days together before he had to leave.. we spent the next day trying to figure out if there was a way for us to have a long distance relationship, and we did our favorite thing to do which was to walk through sex shops together, and we saw some kit to clone a dick.. i got excited because i thought maybe i could give it to Connor as a piece of me so we would stay somewhat close... Connor didn't know i was making it but i had it ready the day be... Continue»
Posted by drewcd 3 years ago  |  Categories: Anal, Fetish, Shemales  |  
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Riding the Lakefront-Chapter 2

August 13, 2008...8pm....Rec lot...Irving Park Rd...Chicago lakefront bike path

The event that actually changed my life began when I needed to piss about 6:30pm while on my bikeride. Tightfitting bike shorts were worn because of the padding in the ass area. But had I worn a pair of shorts with a zipper, none of this would have happened. Had I not worn a zippered tight biker shirt with my 48D tits showing, this might not have happened. But, it also was extremely hot and to be zipped up would have been ridiculous. 95 degrees, humid...typical August summer late afternoon/evening. Even a... Continue»
Posted by titsR4abuse 3 years ago  |  Categories: BDSM, Interracial Sex, Shemales  |  
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