Free Shemale Stories

Annie's Birthday

A few weeks before her birthday Annie started letting her hair grow out. She'd always kept her auburn hair in a cute pixie cut. "Just long enough to grab on to" she'd say. I had asked her about it and she just shrugged the shoulders resting on top of her petite frame. She had small perfect... read more

shemale lover December 13, 2012 100%

Chapter 2 - Cuckold Cruise

If you read Chapter 1, you know how I’ve been a weak, submissive sissy my whole life. My tiny nub of a penis never fully developed has never been inside a woman. I was fortunate enough to find and marry a strong and beautiful woman who accepted my submissive nature but only learned the full scope ... read more

Sissy Annabelle October 7, 2022 80%

I Love To Love You

I Love To Love You Baby By Sabrina G. Langton Author's note: I have published this story on two other sites. I always said it was slightly aurobiographical, but reading it back it is a pretty accurate account of my summer of '88. There are only 3 things that I changed. 2 are itsy bitsy tiny deta... read more

Brina Giselle September 24, 2023 100%

Make that Date

Below is a transcript of a recent episode of a new made for TV series called 'Make that Date'. Chuck: "Hi, everyone, this is Chuck Woolery, and welcome to another episode of . . ." "Make that Date," the audience screams in unison. Chuck: "I would like everyone to pu... read more

shemale lover March 7, 2014 42%

Miko and Mali; Thailand's finest teen sisters

Last August my friends and I went on a “lads holiday” to the beautiful country of Thailand. We had booked a fortnight, which was to consist of five nights in a city hotel in Bangkok, and the remainder in a stunning 5* resort in Phuket. It was my first time in the country, my friends hav... read more

shemale lover June 25, 2014 86%

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 more

shemale lover August 31, 2015 69%

From Gloryhole Peegasm to Shemale

I was in a porn video booth. I young guy stepped into the next one. I was already jerking my small dick, but he didn't even pull his pants down. He asked me if I wanted my dick sucked. Actually I think he said something like, "hey, let me suck your dick." Recently I had let some weird, ... read more

shemale lover August 18, 2011 38%

My Beautiful Surprise

Mark Holloway groaned as he sat up in bed and reached behind him to touch Madison. It was six o'clock on Saturday morning in Birmingham, Alabama. His hand met only a cool pillow and undisturbed sheets. Then he recalled with an increase in his heartbeat that she was due to arrive at the Birmingham In... read more

shemale lover November 1, 2011 100%

Caramel And Devin

I began crossdressing at 12, but it wasn’t until I was 17 when I dressed up completely for the first time. When my parents went away for the weekend to Atlantic City, I took advantage of the opportunity to explore my feminine side to the fullest. As soon as they left the house that summer morn... read more

shemale lover November 10, 2011 77%

Cincinnati Apocalypse Part 6

Faith felt no sensation in her artificial penis, for it lacked nerves and could feel nothing. She felt deprived. In playing the male, she'd like to feel what a man felt, not merely a simulation or a facsimile of what he felt. She wanted to feel the actual feelings themselves. Instead, her cock-that-... read more

shemale lover November 23, 2011 50%

Story for adults Part 4

Alice's place in the household proven to be quite complicated and very demanding. First and foremost she was Mistress Angela's slave and her needs came first. Pleasing and servicing Mistress Angela and Mistress Janice both sexually and otherwise took up a great deal of her time. Her life acquired a ... read more

shemale lover December 20, 2011 75%

Debbie Part 8

Moira sat in her booth at the entrance to the subway station and saw people pass by. She sat there every day selling tickets, and although several thousand people passed her during a shift, she could now recognize many of the regulars and she even knew when to expect them. It was now almost 9 o'cloc... read more

shemale lover December 23, 2011 100%

Chinese Extremes Part 4

The ride to Master's residence was completely uneventful for Lien. The whole way she lay in the trunk of his limousine, hooded and gagged, with her legs strapped together and her arms secured with the armbinder. The trip may have been uneventful, but Lien wasn't bored. She spent the whole trip fanta... read more

shemale lover January 17, 2012 66%

The Greatest Lie Part 2

Never take a long distance bus if other transportation is available. If I had just lobbied my parents a little harder, they probably would have sprung for the plane fare for my summer school session at Minnesota. They were still pissed at me about the problems I had at the end of senior year, but th... read more

shemale lover January 18, 2012 50%

The Greatest Lie Part 3

My weekend escapade with my first real lover, Jake, convinced me that I was destined to live as a girl, despite having been born a boy. Unfortunately, it was my male persona to whom the University of Minnesota had extended admission and a scholarship, and I wasn’t quite sure how they would rea... read more

shemale lover January 19, 2012 100%

Harem Slut Nikki

It has been one year since I began making adult films. I have an exclusive contract with Drew Wilson, the porn director. In that time I’ve mad some 40 odd films and I’ve become quite the internet celebrity. There are tons of fan websites dedicated to me. I was nominated for a few adult v... read more

shemale lover January 30, 2012 100%

Body Image

"Sit down Mona. We have to talk." He had heard those two tiny sentences more than a few times in the last several weeks. Every time he did he felt a strange queasiness in the pit of his stomach. Yet no matter how hard he tried, he could not refuse. He walked over to the couch across fro... read more

shemale lover July 23, 2012 100%

Fifties Housewife

I walked in Timeless Fashions to see if anything new had arrived. Sheila smiled and said, "I have some new things I think you'll love." She waved me to follow her behind the counter and into the back of the store. Sheila has known me for a few years now. I fumbled into her store trying ... read more

shemale lover August 3, 2012 100%

The Slave and the Sissy Part 3

I was more frustrated than ever now; Ella laughed wickedly as I was led away on my leash, my cock pulsing and dribbling like mad in its cage, was there no end to this torture? We turned a corner and we were approached by a smiling harem girl who, giggling passed a sack to mistress. We stood by a doo... read more

shemale lover August 12, 2012 55%

Polish Maid

'You want to get tips,' I explained to Marek, our Polish cleaner, 'You should be more a maid more like her.' Across the street was a girl of about 19, dressed in a fancy dress French maid's costume stumbling home, presumably from a party the night before. She was dressed in a tiny black dress, l... read more

shemale lover September 1, 2012 50%