Sort by
Date Added

Free Stories

84%
The One That Got Away
I was out on a Friday night seriously just looking for a couple beers and a burger. I had a lot of work to do around the yard and house on Saturday and was having some guests for brunch on Sunday. Full weekend, tired from the week. I went downtown to a new gastro pub I’d seen reviewed in the local p... Read full Story
Giantsquid 2017-05-15 5,536 Amateur Bareback Lingerie guy on shemale
68%
Mary Ann and the Tim the Ranch Hand
A few months after my girlfriend moved away suddenly to her grandparents home across the country,( I learned a few years ago she got pregnant) I was riding around on my bike in the street when my neighbor Mary Ann called me over. She was 18, I was still 12 at the time and very horny since my girlfri... Read full Story
Julliana 2017-01-13 7,198 anal pussy Blowjob cum oral sex kiss sissy Love young faggot
86%
Cindy and Juanita Kinky Shemales
Her name was Cindy and she had been born a male. Cindy was a beautiful woman is every way except one. She didn't like the term tranny and preferred being referred to as a shemale. She was truly happy living as a woman. She began taking light doses of hormones at 19 she had stopped hormones beca... Read full Story
darrell 2016-11-30 10,943 anal Big Cock deep throat swallowing foot fetish piercing
86%
My First "Real TS Encounter"
September 2007 Alright, so I’m going to put into writing the story of my very first “Real TS Encounter.” This was back in 2007, so I’m going to do my best to remember as much detail as possible. However it’s been nearly a decade, so we’ll see how it goes. I had be watching “Shemale” porn for a... Read full Story
cngwriter 2016-11-22 15,848 first time shemale transsexual ts encounter
97%
FEM FIRM 4-POP SECRET
Fem Firm 4: Pop Secret by: B-Man View Story Details Rating: XXXAdd Review Added: 11/20/2016 Complete:no Synopsis: Ruby learns a family secret which will change her life forever. Categories:Bimbo Workplace Situations Keywords:Long Finger Na... Read full Story
bennyx709 2016-11-22 9,752 anal sex cocksucking workplace situations
40%
Lay Report #5
Lay Report #5 8/10/2016 Craigslist Style Meet-up from TS Dating Hey, It’s been a few weeks, but finally hooked up again and therefore I am presenting to you “Lay Report #5.” So I was in Manhattan at around 12:30 am on a Wednesday. I was in my car about to go back to Long Island when I... Read full Story
cngwriter 2016-09-04 3,851 ass fucking tgirl
77%
How I Became the Sissy Slut
It all started when I was about 11. I was a very petite and short and had long straight brown hair with whispy bangs as a child. I was often mistaken for a girl. I have a sister who was 6 years older than me about my size she used to dress pretty sexy with the tight jeans and the skin tight sailor b... Read full Story
Tvtrinity 2016-08-29 71,258 Teen (18+) Crossdresser transgender sissy slut.trinity
75%
Jasons dream of becoming a woman comes true
Once upon a time, there was a boy called Jason. Bored with his every day life, he found himself drinking in the pub most nights with his friends. He would come home and sit down in front of the television and flick through the channels. Satellite TV was ok, showing 10 minutes of free view here and t... Read full Story
Katie Fox 2016-08-29 4,665 tranny shemale transformation ts
90%
DISCOVERING BLACK COCK
To the greater Boston general public it was simply a small little known quite private night club located in the back part of Roxbury called The Black Rooster Bar. While in local Gay Community circles, insiders called this private by membership only pub, THE BLACK COCK CASTLE! When first learning... Read full Story
CD DIXIE IN NH 2016-05-10 9,983 Big Cock cumming sperm ebony cock
59%
NORTH HOLLYWOOD GAY BATHHOUSE
Hi so the first time i went to a bathhouse was when i was 18 , i was dating a 44yr old dominate top tranny (Tina) who had the biggest uncut latino thick cock, her cock was the one that made me not only give up on girls but she turned my body and mind into a complete bottom sissy , my butt became her... Read full Story
daddyssissyla 2016-02-22 12,774 anal submissive sissy bbc doggy styду
65%
Perhaps I’ve Read One Too Many Of The Shemales Stories
At the time, I was living in the street that was full of the shemale working girls. I had the opportunity to watch them every night and listen to their amazing shemales stories. After a while, from all those shemales stories I realized that their customers were not after the anal sex as I imagine... Read full Story
shemale lover 2016-01-09 5,214 first time asshole shemale
88%
Purple Kiss, part 1
It happened during a week long trip for work. By the third night in a strange city I had grown tired of the hotel bar and broke away from my work colleagues for change of scenery. I told my coworkers that I was going to bed then quickly made my escape. The night was warm so I decided to take my o... Read full Story
Transadmirer 2016-01-02 9,859 Creampie Shemale Fucks Guy Fetish cum domination gangbang sex
80%
JUERA MARICON
My name is Keven Jeanne and, Yes, I am a Sissy! When I was 13 I put on my mom's panties and some of her lipstick when she was at work. I had longish blonde hair and I ruffled it up - kind of teased it up - and when I looked in her dresser mirror, I almost ejaculated. Because what I saw looking ... Read full Story
Kevyn-JeanneHarris 2015-12-25 6,119 blonde shemale submissive cocksucking
94%
Daddy and his wicked ways
My name is Miss ________________ (You fill in the blanks). I am a TV/TS/CD who likes to be used in a sexual context by manly men. This tale is about me and my desire to be used over and over again. In a way I'm a little reluctant to share my fantasies with the great British public because they&... Read full Story
Daddy knows best ! 2015-11-24 6,236 suck submissive ts cd tv
91%
Eight Inches
Got stranded at my pal Devin’s place this week when it started sleeting like crazy. I decided to wait it out, and wound up bunking on the couch. I couldn’t sleep in my clothes, but I didn’t have anything else to wear so I wound up in nothing but an oversized shirt Dev lent me. A... Read full Story
shemale lover 2015-11-03 6,901 anal shemale handjob
93%
The Hot Girl at the Bar
My girlfriend and I broke up the week before, so I was pretty depressed. The guys at work decided to take me out to the bar after work to get wasted cause that’s what we do. So we all packed into the truck and headed to the bar. When we got there we were the first ones in that night so we sa... Read full Story
shemale lover 2015-10-01 10,187 anal suck Creampie
84%
The Making of Erica - Sperm Loving Crossdresser
Confessions of a Crossdresser I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I have only sucked cocks, but over a hundred at my las... Read full Story
shemale lover 2015-09-03 16,390 shemales Masturbation Fetish
69%
Kits Adventures in the North
**Crossdress Story** It had been about six months since I'd had any chance to dress, any chance to feel sexy and been even longer since I had any kind of sexual contact. Work tends to do that; gets in the way and screws about with "me" time. Luckily, though, it was only a temporary job... Read full Story
shemale lover 2015-08-31 5,429
83%
Cindy She Thong
Dialogue from Cindy’s point of View: Her name is Cindy and she is a shemale. Cindy is a beautiful woman is every way except one. She does not like the term tranny and prefers being referred to as a shemale. She is truly happy living as a woman. She began taking light doses of hormones at 19 she had... Read full Story
mrstanley 2015-07-29 4,961 Big Cock ass fucking deep throat piercing
60%
TAKING CONTROL OF CJ-CHAPTER 1
Two days passed. Then a third. CJ began to feel as though perhaps this was all a 'bluff'. Perhaps this was part of her imagination gone wild. She knew she couldn't tell anyone at this point. Just as her mind started to clear, thinking it was just that the phone rang. Called ID said Easter Seals. She... Read full Story
Titbitch 2015-05-13 3,299 anal gangbang oral
93%
Interracial Sissy Story
(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... Read full Story
shemale lover 2015-05-01 14,933 first time ass Cumshot suck cd sissy make up
78%
Emily and Jane
I'm very proud and happy to publish another jewel today, a story about two shemales from 26-th century, Emily and Jane. Props for this truly delightful story to our forum member, Ila. Excellent work bro! It is the 26th century. Human genetics has advanced to the point where anyone born male or fe... Read full Story
shemale lover 2015-04-11 4,195 anal licking cock sucking
60%
Road trip in India
Well as it happened i had to go out of town for some work and since i was travelling alone in my car i carried my bra n panty with me. i had to go to delhi and i got free around 9 pm and i started the drive back to my place abt 3-4 hrs drive on the way ii stopped on the out skirts of Delhi on a dark... Read full Story
shemale lover 2015-03-17 4,698 anal shemales gay male
92%
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 no... Read full Story
shemale lover 2015-02-27 6,730 ass Cumshot sucking cd sissy
93%
My First Girly Cock
It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. ... Read full Story
shemale lover 2015-02-27 5,432 tranny Cumshot Shemale Fucks Guy ass fucking Guy Fucks Shemale
81%
Ladyboy Switch Story
I am messed up with how I feel about this. I still love looking at women. I love tits and arse. I like the soft feel of women – kissing them and feeling their bodies. I don’t look at men in public and get turned on – men with clothes on do nothing for me. Put me somewhere that I can see those same m... Read full Story
shemale lover 2015-02-27 6,762 Cumshot suck Shemale Fucks Guy Ladyboy ass fucking swallowing
96%
Suck like no other
This is a guest post from our reader, Richard In Houston. He met a beautiful young lady, Terry, who taught him to "suck like no other". An awesome shemale story to read, if You ask me! I was separated from my first wife the first time it ever happened to me. We had only been separated f... Read full Story
shemale lover 2015-02-03 6,939 suck Blowjob shemale
81%
First time in Bangkok
If you have read my story about the first time I was with a TS girl then you know my experience was limited to just a few times. So about 4 years ago I went to Thailand to visit my buddy who was working there in a high profile job with the Thai government. We stayed in his apartment on the 40th floo... Read full Story
shemale lover 2015-01-13 13,343 shemales hardcore Group Sex
91%
For a while I worked as a transsexual street prost
When I first moved to Sydney in my mid 20’s I had trouble meeting the bills. This was desperate times so after a lot of soul searching I decided that the only thing I could do was to become a prostitute. I knew Sydney that the transsexual prostitutes picked up clients on William Street near... Read full Story
shemale lover 2015-01-05 7,282 anal shemales hardcore
85%
The invitation
The envelope was waiting on the mat when Jack and Sally got home from college to the small house they shared in North London. Sally scooped it and what was obviously yet another bill up from the floor and plonked them down on the table in the hall as she shrugged off her coat. The young pair were se... Read full Story
shemale lover 2014-12-15 6,588 shemales Fetish
90%
Painted Laddie for Mr. R
Gabe had had many strange photography assignments for the eccentric, but very rich Mr. R, an avid collector or erotica, but this was perhaps the most challenging. The money was better than good, however, and when he’d put a little thought into it, Gabe saw little problem in the execution of th... Read full Story
shemale lover 2014-12-07 3,583 sucking shemale stroking
95%
A Black Tranny Fantasy
It was only when she emerged from the bedroom in a purple silk nightie that not only clung to her full breasts, but also betrayed the hint of a bulge between her legs, that I realised that it was actually going to happen: my fantasy of sl**ping with a black shemale was about to come true. She paused... Read full Story
shemale lover 2014-12-03 5,587 tranny Cumshot suck ass fucking Interracial
94%
Miss Tiffany Fulfilling Her Dream
Finally, I had everything I needed to dress up for a little fantasy today. Ever since I was a little boy, I had always thought my neighbor Steven was extremely handsome and sexy. At 6 feet 3 inches, Steven is exactly what is described as tall, dark, hard tone and muscular. Tonight, I would finally h... Read full Story
shemale lover 2014-11-17 4,400 ass licking perky tits face fucking
88%
Tgirl trained to be the town whore to serve ALL Black men
A few years back I spent time on and off with several shall we say more dominating types of gentlemen One of them, who for this I shall call Leroy, just loved when we got together to make me totally helpless. It was our 6th or 7th meeting. Leroy and i had been chatting on Yahoo and when he f... Read full Story
__tiffanylondontv__ 2014-09-30 5,868 suck shemale ass fucking Interracial big cocks
90%
A Halloween Hoodie story
This is the story of my first time going out dressed; it was halloween last year (2009). I figured i'd have less to worry about walking around dressed in a gothic tartan corset, spider-web mini-skirt, fencenet tights and about 10 armbands and bangles. It wasn't exactly brilliant but it was the excit... Read full Story
shemale lover 2014-09-29 5,024 sucking shemale cum swallowing
85%
Fucked by indonesian ladyboys
this is a true story of what actually happened to me in bali When i was 17 i was on holiday in bali, indonesia. i'd only had sex once prior, with a genetic girl, and i barely managed to get hard and wasn't able to cum so i knew pussy wasn't for me. i had been clubbing several tim... Read full Story
shemale lover 2014-09-17 60,576 suck Bareback Asian Ladyboy ass fucking
100%
More TS sex
Some time passed since my first encounter with the lovely transvestite and I often remembered it in my lonely bed. But I couldn’t make the decision to seek her again. Maybe afraid from being seen, as she used to walk around near my office I started leaving office before dark. When I went ou... Read full Story
shemale lover 2014-08-19 5,365 shemales gay male oral sex
95%
First TS sex
I think I was near my 35Th birthday and, believe it or not I had never had experience with a transsexual. I had plenty adventures with men and liked it very much as well as with women. Decidedly I was completely bi. As I wrote in previous stories, I’m writing about near 30 years ago. It was... Read full Story
shemale lover 2014-08-11 5,750 shemales gay male wanking
85%
My Date with a Crossdresser
A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity. We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready ye... Read full Story
shemale lover 2014-08-01 18,298 Crossdresser hardcore suck Lingerie ass fucking cd
100%
Dance Contest
My name's Dan and I own The Glass Cat. The Glass Cat is a Female Impersonator club, although lately we're getting a lot of transsexuals, too. The club is pretty well-known and sometimes we get some big-name shemale porn stars in to do a show. Our biggest draw is Tuesday nights. Tuesday night is d... Read full Story
shemale lover 2014-07-01 4,944 sucking shemale teasing
71%
Joanna Tranny Prostitute
Joanna stood on the street corner and casually shifted her posture from one leg to the other. So far it had been a quiet evening for her with few punters around. Not many girls were plying the streets either. She’d had one customer earlier. He had been an Asian guy in a Toyota who’d stop... Read full Story
shemale lover 2014-06-19 6,867 shemales Masturbation voyeur
80%
Trance club
It was the worst day in my life. My girlfriend Ally and I had been quarreling and rowing for several weeks, we were on the verge of breaking up. I just wanted her to be happy. I lived my life for her. I guess I stood no chance to make her smile at me again. We broke up. Ally said everything was chan... Read full Story
shemale lover 2014-05-25 7,665 sucking shemale
92%
A new girl around!
You know, things, I’m gonna tell you about started when I was a teen. I was like every teen guy, I loved web porn, looked at porn on the internet, surfing porn sites through the web space and masturbated a lot. I loved and now love to watch lesbian porn: it was so hot watching girls having sex... Read full Story
shemale lover 2014-05-21 18,326 shemale fingering cumming
33%
Sleazy Walking
I was bored one night, and began to email wanted ads on craigslist to see who was hosting in my area. I lived in spokane, wa at the time in the east central area, sorta behind the fred meyer. This night was boring, my friends had left a while ago with their girl friends, jealousy began to set in. I ... Read full Story
Ville Lohner 2014-05-15 2,722 Stockings Crossdresser Amateur suck Lingerie
90%
Italian hoe!
Verona is a nice city. Here, a motherland of Shakespeare’s “Romeo and Juliet”, there are lots of places of interest to see and enjoy. Verona has much more to offer. The city, also known as Urbs Nobilissima, is the second biggest city in Veneto (after Venice). It is one of the citie... Read full Story
shemale lover 2014-05-11 4,861 ass shemale boobs
100%
More Dirty Sex with Tania. Part Two
Luckily most of the guests at the Premier Inn had now checked in so when we both went down through the reception area it was again deserted except for the receptionist who only acknowledged the door key being placed on the counter. There were a couple of people in the car park but most were only int... Read full Story
shemale lover 2014-04-09 4,825 anal shemales Masturbation
92%
My First Girly Cock
It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. ... Read full Story
shemale lover 2014-03-29 18,537 anal first time shemales
75%
More Dirty Sex with Tania. Part One Hotel Sex
It took quite some planning, after our last meet in the lay-by, but at long last we had both been able to get away at the same time. We, well actually Tania, had arranged our meet to be at the Premier Inn at Witcombe, just south of Cheltenham and just of the A46. Tania was arriving just after lunch ... Read full Story
shemale lover 2014-03-27 4,446 anal shemales Masturbation
74%
My Daughter and I Visit a Lesbian Bar
It is an extremely warm Saturday night and my eighteen year old daughter Krissy and I are sitting around in the house having conversation while we drink sparkling wine. Around midnight I suggest it might be fun if we took off our clothes and sat outside on the front porch. Krissy giggles for a few m... Read full Story
shemale lover 2014-03-17 8,305 shemales Group Sex lesbian sex
93%
SHEMALE SEX IS THE BEST
I had been in sex with gays for 1 year, but had always been intrigued by those hot looking chicks who packed more than a pussy between their legs. I had no idea where to find one in Kanpur I was definitely bi-sexual, still seeing whores, and still going to gloryholes for my cocksucking needs. I w... Read full Story
shemale lover 2014-03-07 4,522 tranny Big Cock ass licking doggy style big boobs rimming
88%
Strip Gaming gets with Kelly
After taking an extremely boring Christian ethics class (required by my college, not by choice) on a late Friday afternoon, I checked my cell to see I had a few messages. It was Kelly and she was celebrating a well deserved A on an Calculus test. The first message read: "Got an A in Calc. Vo... Read full Story
shemale lover 2014-02-27 5,606 anal shemales hardcore
88%
Alaska adventure
I was stuck in my parents apartment, living with them and working at a bar downtown for the summer. I got bored hanging out alone in my room,. so I snapped a few pics and put an ad in the TV/cd section on craigslist. I waited a bit and it wasn't long before someone replied. Then a few dozen ... Read full Story
Ville Lohner 2014-02-18 4,381 anal Crossdresser hardcore Big Cock Interracial
77%
Changes
A story about a mysterious change and how it changed the life of two people forever. The sunlight practically burned my eyes as I slowly woke up. I blinked several times and closed them again for a moment. I felt like crap, way worse than I should have. Last night the guys and I had gone to the bar... Read full Story
bigtranslover 2014-02-11 5,835 female transformation
98%
Shemale Delight
I have always considered myself a, women only, kind of guy. After an experience I had 10 years ago, I have added shemales to my list. Anyway, I love to take road trips and visit different cities, usually out of state. I go on-line to do some research about different cities to see what kind of si... Read full Story
bigtranslover 2013-12-27 10,751 licking sucking pussy
77%
A Night i will Remember 4 Ever
About six months ago I went to a transvestite bar and dance club in the centre of the city where I live. I was dressed in my sexiest all-leather shift minidress, sheer stockings and 4-inch stilettos, and my favourite blonde wig. I was fully made up with long false eyelashes and blue shadow, painted ... Read full Story
bigtranslover 2013-12-19 7,330 anal shemales Group Sex
36%
The Surprise Visit
I had been chatting for some time online with a guy who said he liked crossdressers and loved getting his cock sucked. we chatted numerous nights, roleplayed online. i guess, i don't remember, but i guess i gave him my address. but i worked long changing hours. one thursdau night about 2 am i was co... Read full Story
bigtranslover 2013-12-17 4,552 first time shemales hardcore