Free Shemale Stories

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 more

bigtranslover December 19, 2013 77%

Ladyboy orgy in Thailand

During one of my many nights in the sleaze capital of the world Pattaya, Thailand I was at a certain ladyboy bar all dressed up in my sexiest outfit that the "girls" had ask me to wear in as I had shown them some pics of me dressed. Not that I could ever hope to compete with any of them! ... read more

bigtranslover January 5, 2014 86%

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 more

shemale lover March 29, 2014 92%

Growing up wrong

Hello my name is Krystal, but everyone calls me Krissy. I'm 25 & live in the Detroit area. I work at a local hospital as a Physicians assist & I love it! I'm pretty much a doctor but limited at meds I can proscribe & I don't have to have malpractice insurance. Last night was my third ... read more

shemale lover March 31, 2014 80%

My beautiful tranny!

This guy picks up a girl and takes her to his place. Can you imagine his surprise when he finds out that this girl has a dong? Hi! My name is Andrew! I’m a 5.4 feet tall, with some cute beer belly, crew cut light brown haired guy, blue eyes. My friends say I have a big noseJ but it’s ... read more

shemale lover April 27, 2014 82%

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 more

shemale lover May 25, 2014 80%

A Savannah night

Crossdressed fully and very seductively in only fishnet thigh highs; hooker heels, g-string, garter belt, and bra, (all black), I had intentionally let the man walking around the motel parking lot see me. He'd stopped in his tracks, mouth open, and stared, as I stepped out onto my motel room balcony... read more

shemale lover June 17, 2014 81%

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 intima... read more

shemale lover June 29, 2014 82%

My desire continues after Greg's departure

After Greg,my first black lover,moved away,I THOUGHT that my "experiment" was a passing one. Was I ever wrong. I'd be in bed holding the recent centerfold up with one hand and my other stroking away,yet,when orgasm neared,my thoughts invariably turned to Greg and specifically,his big bl... read more

shemale lover July 13, 2014 100%

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 o... read more

shemale lover June 6, 2011 90%

Dana becomes a woman

All her life, Dana had felt different. Born a boy, she always preferred dressing in girl clothes and playing girl games. She was mistaken for a girl from the time she was toddling - her feminine face and manner always convinced people. By the time she graduated high school, Dana discovered her main... read more

shemale lover August 7, 2014 92%

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 more

shemale lover August 11, 2014 95%

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 more

shemale lover August 19, 2014 100%

Lucky Afternoon

For the past few years I have had this urge to have sex with a man. After finding Xhamster The urge has gotten to the point where I was going to have to do something about it. I found a guy on this site who told me what to watch out for and the best places to meet someone. I do not like going to bar... read more

shemale lover August 29, 2014 100%

The Teacher and Me

Funniest and hottest story of my life right here: Growing up in a small, redneck community, I wasn't going to come out of the closet anytime soon. I had to find an outlet for my sexual desires, even if just for a single night. I resorted to Craig's List the day I turned 18. So there I was on c... read more

shemale lover September 5, 2014 61%

The switch

HI have been married for 12 years now. Trim and dapper, this 35-year-old's marriage was satisfactory enough and I played the role of husband well. Sex with the wife was still good, with both making out at least once a week or on rare occasions, once monthly. Twelve years on in this heterosexual rela... read more

shemale lover October 11, 2014 100%

An Eyeful

“Mom you don’t understand and I can’t talk about it, but trust me it’s something that can’t be helped,” Erica explained to her mother. “Honey you’re not being very understanding.” Erica just rolled her eyes and pulled the phone away from he... read more

shemale lover October 23, 2014 80%

When I realized I was Bye and gay

I was a late bloomer I got married had kids bought a home had all the things to make a happy home but I was restless i needed something else. I was going out with other women about once a week and it was fun and sometimes very hot i even had a few three somes but I always felt I needed something ... read more

shemale lover December 9, 2014 100%

Caught in the act

After my first encounter with John’s dick, I couldn’t get it out of my mind. Two weeks later we met at a friend’s party and we talked about it. He was worried his girl friend might find out. I told him he had noting to worry about as I had as much to lose as he had. But I also said... read more

shemale lover November 15, 2014 89%

Practically gang at a sex club!

About 6 months ago I went to my local sex club in Sydney. It was only about 8pm and not much usually is going on at that time. On the 2nd story there is called the "Orgy Room" a place where people go and sit on the bed with no locked door and it's just first cum first served. I stuc... read more

shemale lover June 14, 2011 84%