Shemales Porn Stories
Page 82

Moms teaches son to become a sissy sperma slut

I never knew my dad.

That's not an excuse for what I've become – and that's not to say I need an excuse – it's just a simple fact that some people find relevant when trying to examine what I've become.

Anyway, he was killed in a plane crash before I was born. Technically, he was killed in a plane crash while I was being born, but he died without knowing that. He'd been overseas at a business conference when my mom called to tell him she was going into labor, and had boarded the first plane he could back to North America. Ironically, it wasn't that long, turbulent, twenty hour flight that... Continue»
Posted by momandboys 2 years ago  |  Categories: Gay Male, Mature, Shemales  |  
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First time dressed in a club Pt # 1

I had been wanting to go out to a club dressed for sometime but was having a hard time deciding to do it, up to this point I had been only dressing in my apartment and for my friend Bill who live upstair from me mostly when he would come down and we would have sex together. I had told him several times of my need to do this and I asked him if he would go with me but it seemed he was into only seeing me dressed here and having sex with me.
I decided that I needed to do this for me just once to actually see if I could be around people dressed as a girl so one night I got a hotel room away fro... Continue»
Posted by MonicaBond 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Where I have never gone before


It feels like I haven’t been used in ages. I’m too much of a scared sissy. I find guys from all over, talk, email, text sometimes. But when it really comes down to it I get too scared. I’ve been with this guy before, his cock is soda can thick and he’s really rough. The day after my first encounter with him, I literally couldn’t walk properly or sit down comfortably. It’s exactly what I look for in a guy. Tall, muscular, dominant, big cock. Lately though, I’ve been dodging him. We agreed to meet this one time two weeks ago, I was really horny and constantly emailed him throughout the week. B... Continue»
Posted by cocksucker1966 1 year ago  |  Categories: Shemales  |  
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Amy The Tranny Chapter 1

I met Amy at an adult theatre in town.
She was dressed to nines in a mini skirt, tight
halter top, and pumps leading up a pair of fishnet
clad legs. I invited her into a private booth
and once inside, went over her price for some
adult fun. She told me I couldn't fuck her as she
was on her period but I knew something was up and asked
her flat out if she was a tranny. She looked at me wearily and slowly nodded her head. I assured her I was into tranny sex and she relaxed and asked if I was into just a quicky or a longer more relaxing session back at her place. Of course I opted for th... Continue»
Posted by panteeluvr 4 years ago  |  Categories: Hardcore, Shemales  |  
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The best s****r ever part 4

Yes these stories are true and please start from the beginning. So far me and my s****r have been fucking for about 4 or 5 years and our dad has recently caught us and joined in.

Out of our parents our mom spends the most time at work so we always found it easier to have sex now that our dad knows whats going on. Over time he let us fuck him anal and he enjoyed it as much as I did and we started to do something called "naked hour" which happened every friday evening, where our mom works until 11pm if she comes home early.

After several months of doing this naked hour sessions and we coul... Continue»
Posted by horndogs 4 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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horny

It was a Friday night and my boyfriend Conrad and I were at a sports bar getting wasted and watching games. Conrad loves watching me flirt and this night was no different and there were lots of men to flirt with. We were playing darts when we were challenged to a game by these two black guys. They introduced themselves as Travis and Kevin and in no time, we were having fun playing and drinking. Kevin was the larger of the two at about 6’2”, 250 lbs. He was really dark and the quiet type. Barely spoke, just smiled. Travis was light skinned and tall and thin, the outgoing/player type and instant... Continue»
Posted by conradherts1 2 years ago  |  Categories: Shemales  |  
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my first cross dressing play time

i sucked my first cock the other day. i posted a ad on craigs saying i like to cross dress and would like to find somebody to dress up with and take turns being sluts to each other and then i posted a few pics of me from my xhamster profile and actually got alot of replies. it took a few weeks but i finaly found somebody that like to dress up and he came over during the day and we started watching porn and i pulled out all my slut clothes and we picked out things that we wanted the other person to wear. he wanted me to dress up just like the pics i sent him so i did, after we got dressed up we... Continue»
Posted by floyd1985 3 years ago  |  Categories: Fetish, First Time, Shemales  |  
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Found my Way

New Years eve I met some guys at a bar that invited me to a party. There were about five couples and they were leaving and going to a house a few miles away. Follow us and don't drive d***k they told me.
Another two rounds of shooters and we left.
Fifteen minutes later I followed the group into a big house in Buckhead.
Ten minutes later I was sitting back on a couch smoking a joint sipping on a mixed drink.
I was so high my vision was blurred and I dropped my drink. I was about to pass out. Billy was one of the guys that invited me to the party came to me and helped me get up and he moved... Continue»
Posted by CrossdresserAtlanta 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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The Perversion of Bev - Part 1: The Beginning

“Some fucking romantic weekend this is turning out to be” thought Bev as she sat alone in the hotel room. Phil had told her he’d booked something special to celebrate their Silver Wedding anniversary and she’d been so looking forward to a weekend away without the k**s. The first setback was a phone call from Phil to say he’d been delayed at work but she should still go to the hotel as planned and he’d meet her there. Now, with the Friday rush hour traffic clogging the A1, he reckoned he wouldn’t be getting there for at least another couple of hours. “Just wait till he gets here” thought Be... Continue»
Posted by Suveran 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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Summer Fun

*Crossdress Story*


Living with your parents is exceptionally annoying, especially when you're 26 and have a fetish for crossdressing. It kind of hampers your "need" for putting on slutty outfits and parade yourself in front of a webcam with a pink-glass buttplug up your ass and a giant rubber cock vibrating away as it burns down your last pair of batteries.
But alas, it's the position i'm in and somehow i've made it this far without too many suspicions.
There was the incident a few months back when my mum and dad were at work and I took the opportunity to clean all my sex toys; taking t... Continue»
Posted by KitsuneTV 4 years ago  |  Categories: Shemales  |  
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My very first experience with my classmate (episod

He was amused by the sight...of me in lingerie..standing on the porch,it was obvious he was in a shock (or state of extacy?) and couldn't take his sparkling blue eyes off my firm body inside the dress...he closed the door behind,like he was worrying if someone could see us ..I don't know why but i felt the tears running down my cheeks as a result of this emotional discharge and hugged him,saying ''I was scared to death..of losing you...I thought you would never talk to me again''...Maybe i was being hysterical but i really wasn't thinking healthy at that moment..a typical girl:) I started to ... Continue»
Posted by Slave4str8twinks 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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Daddy's Popper Challenge

Since I've been enjoying the users’ stories here so much I thought I'd share one.
I'm a pretty good looking guy, love girls and pussy, but I am a closet tranny chasers. I love hooking up with crossdressers and transgender. I dressed a little in high school and college; I left behind the clothes but not the lust for the femme bois.

Last week when work was tough I needed a five minute distraction to clear my head so I called up Craigslist and browsed the Casual Encounters T4M. This was around 2:00 in the afternoon, a very hit and miss time. The ad that peaked my interest was "Mature Crossd... Continue»
Posted by gypsy61 3 years ago  |  Categories: Mature, Shemales  |  
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He Got Used and Didn't Mind (Part Two)

I got the 1,000 views so here is part two. 1,000 views or 10 comments and I will write part three.

As Dave drove home from Jesse's, he called Lucy to let her know he is on his way home. She told him she had gone out with Carla for a girls night. When Dave got home he hit the shower, put his clothes in the hamper and went to bed.

Lucy picked up Carla from her house went to the bars in down town. Guys were buying them drinks and hitting on them. Their conversation was getting disrupted so much they decided to go to the gay bar just to see if they could talk and have a good time. Once there... Continue»
Posted by mrman1982 2 years ago  |  Categories: Voyeur, Hardcore, Shemales  |  
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how i got my start as a sissy

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Growing up was tough . I spent a lot of my younger years trying to figure out if I was normal or not . Had many girl friends but still I had an attraction to cock . This all started at a very early age and abuse continued till upper ages from both sexes . I really started exploring my sexuality after I joined the army and got away from home . There I was used by other army high ranking men who knew what they were looking for . I had a command sgt. major for my first dom who took me out one night , Made me dress for him and then proceeded to **** me . I found that this turned me on deeply ... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  
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working at a house

I'm fitting a kitchen at a couples house right now. They are both in their thirties. as I arrived in the morning they were waiting for me, they needed to go out and would be most of the day, to which I agreed to be fine on my own.
After about an hour or so I decided to look around in her bedroom. she had lots of sexy dresses, suspenders and stockings. I also found some lovely slightly soiled knickers in her washbasket. After sniffing and licking the gusset, I was getting very hot. I decided to dress up in her sexy gear. I put on her stockings, suspenders and bra along with the knickers I'd b... Continue»
Posted by tarajenkins53 4 years ago  |  Categories: Shemales, Voyeur  |  
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Life with Brian

Brian and I had been best friends for as long as I could remember, although I wondered why from time to time. Sometimes he drove me nuts. He sometimes behaved really oafishly - or just insensitively - and he could be opinionated, too. Not that he didn’t have good reason to be. He was always one of the smartest k**s I knew, and he was captain of the football team when we were at high school. Brian was one of those good-looking golden boys for whom life always naturally came easy, smiling his way through difficult situations with a flash of his blue eyes and an easy laugh. Whenever we fell out h... Continue»
Posted by lana100 1 year ago  |  Categories: Shemales  |  
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The Curse (Sissy Story) by sdvine

I wasn't really having a good time that night at the bar. Truth be told, I had been practically dragged out in the first place by my best friend Joe, who told me he was tired of me "sitting on (my) ass" every night "finding new ways to be boring." Quite frankly, if this is what qualified as being not boring, I'd rather be bored to tears. To begin with, I'm not much of a drinker, so leaving the house to go to place designed for buying and consuming alcohol made little sense to me. Additionally, I'm not what you'd call a people person. I was generally okay with individual people as met them, but... Continue»
Posted by sissyAlyna 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
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Loving TS Sex

living in a medium size city 30 years ago, it was necessary to stay into the closet. That way of live is really still the reason why I never outed myself, even after years living in different bigger cities and several countries.

I had acquired a taste for transsexuals, considering them the best of two worlds. Never could resist the view of a beautiful girl knowing that there were a certain something between her legs.

When I felt the urge inside me I cruised into the night looking for the zones were the TS used to hunt. I always made sure to pick up a girl when no other cars were aroun... Continue»
Posted by bloodyhugo 5 years ago  |  Categories: Gay Male, Shemales  |  
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Hedonistic Crossdressing, Part 3

The best way to describe Vince, probaly is that he was a socially functioning pervert. I had no idea just how varied, and intense, his sense of erotica was, but I was going to find out as time went on. Perhaps the worst thing is (or best perhaps, depending on your point of view), is that I became quite the little "apprentice", you might say.

I'd been his "guest" for only a few hours, and I'd experienced more than I'd ever dreamed. I've dressed, I've sucked my first ever cock, been fucked hard up the ass, taken cum, been made to cum like a girl, been made to take ass to mouth, w... Continue»
Posted by elainetgrl 4 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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An On-line Sissy Lives Her Dream

(Dedicated to a hot little sissy here on xhamster, Sluttish, whose looks and fantasies inspired this story. Her fantasy name is April. That’s where this story starts.)

It started innocuously enough with what seemed like a harmless exchange of private messages on a friends-based porn site. A person identifying as a male sent a note to a young sissy whose profile expressed some fantasies about being made into a full-time sissy, perhaps involving some f***ed feminization and even surgical “enhancements.” The young sissy, April, responded openly and eagerly, and the conversation developed into ... Continue»
Posted by scatpetsmaster 1 year ago  |  Categories: Anal, BDSM, Shemales  |  
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