Shemales Porn Stories
Page 10

A Bad day

It was a rainy and cold night when I entered the smoke-
filled bar just off the Interstate. A series of personal
defeats had sent me home for the comfort of my most
recent lover. My unexpected early arrival found her in
the arms of another and after a flurry of ill
contemplated accusations, we were soon on our separate

Fearing further confrontations, I eased my wheels into
the unimposing parking lot and with a dash of cologne
entered the dimly-lit room awash in the mid summers rain.
My full intention was to drown my sorrows in solitude and
seek solstice in the mote... Continue»
Posted by vdub-guy 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Who's The Sissy Now?

Like many people, I was bullied in school. I was small, slender and effeminate and, as a result, was often called gay, queer, fag and sissy by school bullies. The fact that what they said was sort of true just made it closer to the bone and more painful to hear. Like many teenage boys, I was going through something of an identity crisis surrounding my body and my blossoming sexuality. The feelings that I had always had as a c***d that me being a boy wasn't quite right were now increasingly pronounced. Of course, under the circumstances, this just made me more embarrassed and insecure, I was so... Continue»
Posted by 425olds 4 months ago  |  Categories: Fetish, Hardcore, Shemales  |  

A sexy blonde Mature gets a surprise called Mandy

My name is Irma, and I'm a fit blonde women going near 60, and I happens to be a lesbian. In my long life I have been with a couple guys before, but that's it. Anyway, one night, I took my yet fitted red dress, with transparent sleeves, dekoltee and cutouts for visiting a new club, looking for some cute younger ladies, that maybe I'd take home. I saw a lot of worthy candidates. I wasn't a slut or anything like that, but I definitely played the field. I looked around the entire club a few times, and caught a few eyes. I saw a few ladies casually stirring their drinks, or just flat out eye fucki... Continue»
Posted by mandy_66_night 4 months ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
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Hotel sissy slur blowbang

So....about 3 or 4 months ago i met a guy in chatropolis. In the 'showoffs with webcam room' ill call him tom as im not sure he and his friends would want me using real names on the web. We talked and flirted for bout an hour. I have to get pretty horny to cam for a guy. He was totally into the kinda stuff that gets me off (sissy humiliation and cum eating) so eventually i cammed for him he watched me dress up girly, toy my ass and finally blow my sissy load into my cum cup before guzzling it down like a crazed slut. All of the time egging me on, teasing me, humiliating me, abusing me until he... Continue»
Posted by hornyTVluvr 4 months ago  |  Categories: First Time, Group Sex, Shemales  |  
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Bi MMF, FemDom, Cross Dressing, Cuckold - Part 2

After my mind blowing experience with my friend and his wife, my mind was constantly thinking about how good the sex was and thinking about our next date on Friday. I called my friend on Wednesday after we fucked for the first time. He answered with a slight giggle. We talked about how fuckin hot out experience was and how we should've been fucking since way before. He told me his wife had now lost all respect for him since we had our sexual session, but that she was really excited to do it again. I asked if I could speak to her. He sheepishly talked to her and said I wanted to talk to her. ... Continue»
Posted by chrissylegs 4 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Bi MMF, FemDom, Cross Dressing, Cuckold - Part 1

I have these friends, a husband and wife. For the longest time, I've wanted badly to have sex with both of them. First I wanted just him, but I thought it would be even better if I involved both of them.

I'm bi, but they don't know that. Anyway, after years of hanging out with them, I see how domineering she is over her husband - my friend. She really puts him down, bitches at him constantly and belittles him, in front of anybody and everybody. She's really mean, but she's mostly been nice to me. She's pretty, blonde, curvy but not fat. My friend is not so much handsome as he is "pretty". H... Continue»
Posted by chrissylegs 4 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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Gay at the YMCA

I was standing naked in the sauna. Heat was way up. I had my butt to the door. Suddenly a guy walks in then sits down. I hurriedly covered myself and slowly looked at him. He had been exercising near me upstairs. He sat with his towel across his knees on the higher level bench. His soft curvy cock hung down. His feet on the lower level. I was covered up and I felt a ting in my lil cock as if I was getting hard. {I recalled being in the college dorm boys showers. I saw some other boys with nice cocks and got a hard on. One had red pubic ha... Continue»
Posted by robin48 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Closet Sissy step Son Made Into step Daughter 3

I woke up with my s****r still a sl**p in my arms. At first I thought I had dreamt the whole thing. Mom and s*s had known about me wearing their stuff and had dressed me up and turned me into a girl. My b*****r, Zach, had fucked my ass. My dad had fucked me as well and my s****r showed me how to suck cock. And for the first time I had put my dick in a women's vagina, as my s****r rode me to one of the best orgasms I have ever had.

But I let my s****r go and moved down to her pussy to give her a nice ... Continue»
Posted by Batman_112 4 months ago  |  Categories: Anal, Taboo, Shemales  |  

Restaurant Futa Fuck (Part 2)

Sara sat back on the toilet seat, legs spread, with her girly cock flopped against her stomach. The girthy member still twitched and leaked small globs of cum, and I wanted to put it back into my mouth so badly. But I had a more pressing issue; her dripping wet pussy was begging to be fucked.

"What are you waiting for, Bianca? Fuck me!" Sara looked into my eyes with a pleading look on her face. She had her legs spread as wide as they could, and her pussy looked gorgeous sitting beneath her futa cock and balls. She grabbed my hips and tried to pull me into her.

"Be patient, babe! You'll... Continue»
Posted by BiancaBigTits 4 months ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
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Jamie's Descent Part 7

Chapter 7

Vanessa smiled to herself as she viewed the edited version of the film
she had made of Jamie getting fucked. Jamie obviously had no idea that
she had been filmed but Vanessa was already very pleased with the
result. This film together with a similarly edited version of Jamie's
first session with Fiona would form the basis of the marketing plan for

Vanessa knew that there would be a number of existing clients who would
cream themselves at the prospect of a session with Jamie already but
Vanessa, as usual, was thinking much bigger than that. She felt Jamie
had ... Continue»
Posted by nikkiesilk 4 months ago  |  Categories: Shemales  |  
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Gym pegging

my world of pegging is only just beginning but every time I get pegged it gets me that little bit hornier. This is one of those events that sparked my addiction to taking cock from a woman and being her bitch

When I woke up this Saturday morning I was hornier than usual, but I had to suppress my urges in order to make a 5:30am group fitness class. I put on my normal workout clothes, Gray/ White Stripe Shimera Boyshorts panties, Nike loose leg shorts, t-shirt, hoodie, socks and New Balance cross trainers. I like wearing the boy shorts for two reasons, one- they are very comfortable and two, ... Continue»
Posted by nickfun69 4 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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Andrew’s Angel

Andrew always grew up feeling more then just a little different from the rest of the boys. He never felt sexually attracted to girl’s bodies but instead felt attraction for their clothes. He knew he was straight because he never liked guys so he just assumed he was straight.

This began his seventh grade year and followed him into his senior year of high school. He started off by reading sissy literotica and watching sissy hypnosis. He then began experimenting by trying on his s****r’s clothes that she had left behind when she went to college. It then progressed to putting tampon... Continue»
Posted by prosgasm 4 months ago  |  Categories: Anal, Shemales  |  
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My wife introduces me to submission and cuckoldry

The next morning after an early breakfast my wife and i set out for Jeanie's house, on the way i asked her what she would be doing for the day and she said that she had some stuff that she needed to buy and that i would be more use helping Jeanie out than moaning about shopping as i usually did. I nodded and said what is Jeanie like as i would be spending several hours in the company of a woman that i had only met for a very short time. She thought for a while before answering me and said that Jeanie was a lovely woman but a woman who didn't tolerate fools, that she had a sense of humour, but ... Continue»
Posted by oldognewtrix 4 months ago  |  Categories: BDSM, Mature, Shemales  |  
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Hospital visit

I injured my knee and needed surgery on it, the Doctor set the date and I booked a private room. Not liking a roommate with a bunch of noisy visitors.

The date came and I checked in at administrations, and was taken to my room. My nurses came in and introduced themselves and said if there's anything I need just push the button. That afternoon a nurse came in with a hospital gown and said I need to completely undress and put it on. I waited for her to leave, then I stripped down and put the stupid thing on. No matter what you do you can't keep from letting your ass hang out. I wrapped it be... Continue»
Posted by fengunn 4 months ago  |  Categories: First Time, Mature, Shemales  |  
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My First Doll Sex

Long story short, I got my hands on a pair of little bratz dolls. I had seen the doll cumming vids here on xhamster already, and certainly didn't dislike them. I also like how many doll lovers you can find on here.

I'm not talking about blow up dolls, or simulated faces with mouths, not that kind of thing. Nothing wrong with it, huge turn on... and if you look at my list of faves you will still see dolls like that as well as devices that don't look like anything human but that provide friction in some way shape or form to be applied to the shaft of the needy man's penis.

I love to cal... Continue»
Posted by FigBlaster 4 months ago  |  Categories: Fetish, Shemales, Taboo  |  

Jessica and the strong man

This story carries on with some of Jessica's naughty adventures as she delves deeper and deeper into becoming a cross dressing sissy slut. You can read the previous two part story of her first meet on my profile.

After that first meet with "John" at the hotel, Jessica was doing all she could to meet people and get more experience sucking and fucking cocks. She'd managed to get a few meets, nothing special but it all counted on the learning curve. Then, one night while sitting online and chatting in one of her usual chat rooms, a private message popped up from someone called "musclefck". Nev... Continue»
Posted by Want2BeTrans 4 months ago  |  Categories: Anal, Shemales  |  
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My name is Penny, a nylon loving transvestite and this is my story of a first time kinky encounter out of my home. I have always envied other TVs who seem to lead the kinky life and love looking at their pictures and reading their stories. It was time to venture out myself I am almost 53 years old so nothing ventured nothing gained. I should think for all of my life I've had a great interest in retro lingerie and nylons with memories of high heels clicking around the home. That feminine whisper of sheer nylons and silky petticoats rubbing against tight skirts and dresses always stayed with me.... Continue»
Posted by SheerNylonPenny 4 months ago  |  Categories: Fetish, First Time, Shemales  |  
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My wife introduces me to submission and cuckoldry.

I was instructed to put the DVD into the player which i did, and my wife held out her hand for the remote control which i placed in her hand. She pointed to the sofa and indicated that i should sit as she sipped her drink from the glass that i had refilled, she pointed the remote at the player and pressed the play button. I sat there watching as the DVD played and could feel my wife's eyes on me every now and again as the scenes unfolded before us. The story was one of a man who's wife wanted someone who was "better equipped" to satisfy her sexually and the husband over the length of the DVD f... Continue»
Posted by oldognewtrix 4 months ago  |  Categories: BDSM, Mature, Shemales  |  

Girlfriend Changed My Life Forever


I have enjoyed the sensation of wearing women's clothing since the summer of 1976. I discovered my liking for female outfits after I my girl-friend, Jane, left her black bra in my bag & I found myself trying it on & wanking. When I told Jane about her bra,she said she hoped I hadn't stained it with cum. I looked at her & told her I left it in my bag all the time,& I returned the item to her. Later that night, after a bottle or three of wine I admitted to wearing it to wank. Still giggling Jane asked if ... Continue»
Posted by Tvluver1958 4 months ago  |  Categories: Group Sex, Masturbation, Shemales  |  
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s****rs boyfriend.

There I was trying my s****rs panties on when I here'd a voice say "hahaha I knew you would look good in panties faggot" my hart snack I turned my head to see my s****rs boyfriend standing there with his huge cock in his hand with a look on his face I have never seen before. I said "what the fuck are you doing here dean" he said "I think the question is what the fuck are you doing with your s****rs panties on" I was so embarrassed I had no words to say. I went to walk out the room so I could get changed he stood in the door way and said "where the fuck are you going I have pictures of what you... Continue»
Posted by blacklj 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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