Free Shemale Stories

Sexy Young Shemale

When I was twelve my next door neighbors Sam and Ted trained me in the art of cocksucking and creamy yummy delicious cum eating for hours everyday during my summer vacation and I fucking loved it! I was small framed and wore my long blonde hair in a pony tail and always wore my smallest shorts so I ... read more

shemale lover September 28, 2018 74%

Shemale First Time

First time Sex with a shemale. Intro. I have read several stories of first time sex with Transexuals and none relate to my experience. So for those who are truly curious about how to go about it and what it is like this is my tale. I have always been a straight guy as far as I know. Married... read more

shemale lover August 24, 2011 87%

Giving Away Virginia Holton

Today would have to wait, thought Marla Holton as she hurriedly gathered her bag and notebook in preparation for a no-holds-barred departure from her office at Prism Design. As general manager she had the privilege of arriving and leaving at will, though no one could ever fault her for not putting i... read more

shemale lover October 8, 2011 50%

Barbara & Vikky Part 1

I'd known Barbara for some time now. She was a mutual friend of a friend, Trina, and we often bumped into each other in the street, or at the store. I liked her and appreciated her company and humour. She was 57, somewhat older than me, being in my mid-30's. We spent many evenings chatting and laugh... read more

shemale lover October 22, 2011 100%

Barbara and Vikky Part 3

In my mind's eye, the scene was as lurid and downright perverted as anything constructed by any artist or photographer: a confusion of golden curls, shoulders, thighs, tongues and pulsing cocks. The sound was a low, constant mesh of breathing and moaning, grunting and sighing: a languid, private mon... read more

shemale lover November 8, 2011 100%

Mel and me in rochester!

The musical orchestra Mel and i are in had a performance in Rochester ,New York and i needed someone to share a room with at hotel. Mel was the first person who came to mind,and since blowing him last time i thought i would ask him. Mel told me his wife wouldn"t be going and he would love to sh... read more

shemale lover November 24, 2011 100%

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%

Sadopsychorama

He liked Clyrissa. She was a cock-hungry female if there ever was one. At 5'5", she had platinum blonde dyed hair, big tits, and a tight waist. She was a hot lay. But the best thing about her - the thing that stiffened his cock whenever he saw her was the fact that she was 53 years old. Somethi... read more

shemale lover December 24, 2011 50%

True story tv first dogging

I am a mature TV living in the north of the UK. I have been dressing since I was 7 and having nylon led sexual fun since my early teens. The result today I have a very large wardrobe of clothes and shoes, am 100% smooth apart from a landing strip and have manicured nails and shaped eyebrows and with... read more

shemale lover January 8, 2012 100%

Family Frolic

FRIDAY My sister and her husband wanted to take a few weeks off in the sun and asked me to look after their kids for a while. I'd move out of my tiny apartment and into their house for the duration. As I was still living off my severance and they had a nice spread with an indoor pool and a h... read more

shemale lover January 14, 2012 95%

Baby Face Jack's Biggest Fight

The referee held his gloved hand high in the air. The crowd was hushed as the ring announcer spoke, "Ladies and Gentlemen, the winner of this World Featherweight Championship Boxing Match to unify the title, by technical knockout, and still undefeated; Baby-face Jack Mc Coy." The crowd scr... read more

shemale lover February 8, 2012 50%

Teacher Student Confidentiality

It was raining cats and dogs outside as Ms. Catherine Walker (Cat by her friends) graded her Accelerated Integrated Geometry test scores. Her was long and flowing and her sweater was purposely pulled low to embarrass the male teachers with her cleavage. Her cock twitched as she shifted her leg to a ... read more

shemale lover February 11, 2012 83%

A Game within a Game Part 1

Epilogue Rob came home from work. His wife Jenny was waiting for him. In her hands she held a letter. Jenny said: "We received this letter today. It is sad news from Marion S. We have met her and her husband John a few times - do you remember? John has had a car accident while driving fas... read more

shemale lover March 5, 2012 100%

A Perfect Life

The reasons I am not writing this myself. I have finally convinced someone to do it for me. She promised to post it on the Internet, but only as fiction. I suppose it is a bit unbelievable. It all started with the best of intentions. I had married my love while we were still in college. She... read more

shemale lover May 5, 2012 50%

The Bitch Bites Back

Pamela stood huddled in the dark doorway, halfway down the back alley. It was cold and a light drizzle had settled in, the sheets of fine rain just discernible in the dull light of the single working lamp halfway down the alley. Pamela was in her mid forties and fighting a losing battle against t... read more

shemale lover May 12, 2012 100%

Bike Shed Rendezvous

Chapter 1 A meeting you can't refuse The sun is shining brightly, but the ground is still damp from the morning's rain and the air is very cold. It's lunch time and you quickly walk across the College car park to the sports pavilion. Becky your sweet heart has told you to meet her and she's been ... read more

shemale lover June 11, 2012 100%

Black Love: Transsexual Edition

My name is Steve Vincent. A big and tall young Black man living in the city of Brockton, Massachusetts. Currently, I'm a graduate student at the University of Massachusetts in downtown Boston. When I'm not in class, I work for the Department of Corrections. I'm openly bisexual, and love to have fun.... read more

shemale lover June 27, 2012 83%

Al Fresco: An Erotic Sci Fi Tale

"Thank goodness for modern science," Ali said as she smoothed her tight black skirt across her shapely hips. The tall brunette turned this way and that in front of her mirror, admiring her taut, toned, and trim figure. Her hands moved up from her hips to cup the twin handfuls at her chest,... read more

shemale lover September 19, 2012 50%

Buying Heels

I have to know what it feels like to wear heels. I have the house to myself tonight and I'm going to play. I already have panties but want to buy some new ones. My wife bought me a black, frilly thong which I wore for her when we went out one night; I also have a cheap, supermarket pair of sheer ... read more

shemale lover September 30, 2012 100%

First Time Sissy Maid

I had been fantasizing for many years about serving a dominant Mistress, watching lots of movies online, and generally lusting over the doms I saw posting ads. At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for... read more

shemale lover October 27, 2012 70%