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%

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 more

bigtranslover December 27, 2013 98%

A girl from the bar!

This guy picks up a chick in the bar and takes her to a private room, the only thing on his mind is to fuck her, but there’s a surprise that the chick has prepared for him! When I stepped down to the hotel’s bar I didn’t even notice that girl at once. I sat my ass down on the so... read more

shemale lover April 23, 2014 88%

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 more

shemale lover November 17, 2014 94%

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 more

shemale lover December 7, 2014 90%

The Training of Maria Louise

Chapter 1 I’ve decided, since you’ve told me you want to be a little dirty tart, that I should punish you by being a cuckold, someone who’s wife is unfaithful. We will begin by transforming you into Maria, we will apply your make up and dress you in white silk underwear, a nice ... read more

shemale lover March 20, 2016 69%

Unforgettable First Time

I am in my late thirties and have known for a while that I have a sexy body. I'm 5'11", slim and athletic with little cherry butt and shapely legs. A lot of women have told me my body is sexy. A few men have mentioned it too. Sometimes I get photo-snapped at the pool or the beach. I've been luc... read more

shemale lover May 6, 2016 85%

The Roommate

I’ve been rooming with Bob for two years now. He and I met about 5 years back, while we both worked at the grocery store to get through college. We were good friends from the moment we met. We had similar interests, were both outgoing, good looking, and hated working at the grocery store. ... read more

shemale lover February 26, 2018 97%

Butt Sluts

My name is Jimmy James. When I started high school, my parents shipped me out to boarding school to teach me discipline. They were mad because I had always been a disappointment to them. I wasn’t terribly manly and I liked to dress in girls clothes. The more often they caught me dressed like a... read more

shemale lover December 22, 2018 91%

New Girl in Town

Margo sat next to me in the coffee shop late that Saturday afternoon. His real name was Mark, but he was one of the loveliest Drag Queens in New York City. I had been dressing secretly at home in my mother’s and sister’s clothes for just over three years, but at 18 years old, I had never... read more

shemale lover June 4, 2019 94%

Meet with Jan part 2

We sat down, chatting amiably, drinking in the view of each other. Jan had on her black PVC body, with matching corset, elbow gloves and midi skirt. The skirt was already tented, as her lovely big boner bulged below. She always wore black seamed stockings, each held by 8 suspenders, but they were mo... read more

shemale lover August 8, 2011 66%

Exotic Erotic Janaina

As the music played in the background, Janaína, the lovely Brazilian babe and her partner slow danced together. Their bodies moved almost as one and from across the room a tall handsome older man looked on. Behind his glass of wine he admired them, the way they moved together, the way his coc... read more

shemale lover August 13, 2011 100%

Sex In Stilettos

Standing before the full-length bedroom mirror, I treated my reflection to an almost unjustly critical appraisal. My indecently short black leather dress clung for dear life to my every curve and went perfectly with my high heels, whorish fishnets and black leather jacket. It was the sixth outfit I ... read more

shemale lover August 13, 2011 100%

Traci the Maid

Traci had gotten a job as a maid in a rich man's house. She looked just like any blond 26-year old woman - long legs, slender waist and high size C breasts. She had a heart-shaped face and giggled at all the right times. Only Traci had a secret that nobody at her knew job knew about - she had a 6... read more

shemale lover August 14, 2011 88%

Out of Town Meeting

Dinner was seamless, the food, the music, the wine, the company. Tony’s out of town business meetings were usually painful, in that he hated living out of a suitcase and eating alone in overpriced restaurants. This trip, he was enjoying every second of it. He’d met up with Chantal, a wom... read more

shemale lover August 14, 2011 50%

Fancy Dress Erotica

It was Tony's eighteenth birthday and his parents had decided to throw him a fancy dress party. For a laugh, myself and some of the the other guys at the running club decided that we would dress as tarts for the night. My name is Andy by the way. I am 16 and have been running for the SNCC Running... read more

shemale lover August 24, 2011 100%

Father In Law Shemale Adventure

My wife's parents were visiting LA from back east. We live in a small one-bedroom apartment in the valley. She wanted them to stay with us but we didn't have room. They got a room in West Hollywood. My wife and her mom had gone shopping for the day. I was supposed to be at work but at the last momen... read more

shemale lover August 26, 2011 85%

Sudden Shemale

I woke up from the anaesthetic, still very groggy and uncertain. I couldn't remember anything, and my head and body ached terribly. I glanced around, trying to lift my head off the pillow, but it just didn't work. After a few minutes, I tried again, and this time I managed to stand up. I was ... read more

shemale lover August 30, 2011 100%

My Shemale Stepmother Part 1

My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was re... read more

shemale lover September 1, 2011 79%

How I Became Vanessa Part 1

I was a man before becoming Vanessa, and my name was Mike. I was heterosexual and I was going out with my first "serious" girl friend for two years when all this started. I was still living with my mother who had been divorced for a decade before getting remarried. Her new husband moved to... read more

shemale lover September 9, 2011 80%