Free Shemale Stories

Andy In Pantyhose

He had the house to himself for a few hours. Andy slid his older sister Kelly's taupe nylon pantyhose slowly up his nice, smooth legs, wriggled them up around his narrow boyish waist the band snapping in place. His penis was so stiff against the wispy fabric! He sighed happily. Sitting down on ... read more

ALEXEAMES January 18, 2024 100%

A Fantasy in Pantyhose

I always go out to the same bar on thursdays. The women are hot and long legged and they always wear pantyhose. Like usual, I dress in jeans, collared shirt and a jacket, deck shoes or dress shoes. Underneath, pantyhose. Always sheer to waist, no underwear and always nude. My jeans are long enough t... read more

jonezn4ph November 24, 2012 88%

Bi Pantyhose Passion

I've had a Pantyhose Fetish for over 30 years now, and love wearing them on a daily basis. But back in the summer of 1995, I suffered a heat stroke, and almost died, when I recovered, I vowed I would stop fantasizing, and live out these dreams and fantasies. I had been masturbating while dress... read more

shemale lover June 4, 2012 100%

My story, more or less pt.3

Earlier on, when I was scouring through various drawers and closets for feminine clothes in my home I have stumbled upon two old skipping ropes. "A fun time" I thought to myself, not giving them another look and continuing with my search. Little did I know they would become the backbone of my "sessi... read more

Thigh_High_Boi January 6, 2023 100%

My story, more or less Pt.1

I always knew I was different. I enjoyed playing with dolls and being around girls, I felt safe and in my place. When I got my first smartphone I have discovered porn, and boy was it an adventure! I have watched every type you can think of, but eventually I settled on shemales, the perfect cross ... read more

Thigh_High_Boi December 22, 2022 100%

From accidental trans porn addiction to a cum filled booty

One night when I was around 30 or so I was watching some porn, nothing unusual for a guy like me, aka a sex addict. Sex addiction is great if you’re Tiger Woods and swimming in poon, but for guys like me - regular, awkward, slightly handsome in a very boyish way, weirdos — it’s not that fun. We... read more

CDJaneBooty April 1, 2022 100%

My story, more or less pt.2

So there I was, a boy with a desire. (Refer to pt.1 for context) A few months went by from the "initiation" and I've progressed quite a bit I have switched from shemale porn to femboy porn, to relate to the main characters more. I have also scoured every closet in desperate search f... read more

Thigh_High_Boi December 23, 2022 100%

From a 50's virgin to a Mature good for all

***Prologue - Confessions: Every day since I offered my virginity, I put myself in the shoes of a woman. The little town where I live forbids me to show myself socially. However I made myself an accomplice, my epilator who receives me after closing. Since my new beginning, male masturbations are not... read more

hippocampus_171 January 11, 2023 100%

Karen, My School Teacher Part 2

Just Staying a bit By FoxyHosed “Don't mention it. Now let me start on the pasta with meatballs!” She stood up from her chair “And besides, it will be nice to have someone to eat with, for a change!” She went to the kitchen to start dinner. “Make yourself feel at home!” I watched some TV ... read more

FoxyHosed February 1, 2021 100%

Karen, My School Teacher Part 3

Regret... Hmm Maybe Not. By FoxyHosed My excuse for a cock got hard again. My horniness got the better off me. I went to lock the front door. I took my shoes, pants and sweater off. I stood in the hallway only in pantyhose and t-shirt. ‘Don't do this. Walk away from this now. But you go to boa... read more

FoxyHosed February 5, 2021 100%

Karen, My School Teacher Part 4

Meeting my other teacher By FoxyHosed Next morning as I woke up, I jumped in my clothes and got myself a coffee, and went to school. I got in 15 minutes early because I didn't want to run into Karen. As I entered the door to the school, I saw some of my classmates. I thought the coast was clea... read more

FoxyHosed February 17, 2021 100%

Mommies little sissy slut

I have been crossdressing for years now not known to my mother (or so I thought). she is the only person I live with at the moment. when she was going to be out for a few hours I went to her underwear drawer and inside was the most sexy, silky, feminine underwear set I had ever seen complete with ca... read more

shemale lover September 9, 2014 71%

Emily's First Daddy

This is a story how a curious male can become a sissy slut seemingly overnight. So I was in an online adult chat just talking with random people and happened to mentioned where I live. Then all of sudden, I got a message from a man calling himself bear daddy. He introduced himself and said he was ... read more

User Removed October 21, 2019 100%

Karen, My School Teacher Part 5

The Bus Station By FoxyHosed I looked around, but no one was there. It was dark and pretty cold night outside. I felt the air blowing around and up my pantyhose encased legs and ass. Mmmm nice. I started walking to the bus stop a few blocks further down from the school. I felt very attractive g... read more

FoxyHosed March 15, 2021 100%

A Downtown Moment

I had reason to head downtown for a meeting with some industry colleagues and after my meeting I dropped in to see a friend of mine who I used to work with. Loretta and I worked together for about a year on similar project as contract workers, I moved on to other things and she stayed with the compa... read more

shemale lover February 28, 2012 100%

Whores and Pimps - Part I

Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm h... read more

shemale lover May 13, 2012 85%

Karen, My School Teacher Part 1

The Meet By FoxyHosed It all started when we got a new class teacher. Her name was Karen. She was a mature lady and had dark red hair to her shoulders. That first day she wore some short dark blue jeans and a brown blouse. My other classmates started whispering about her. “He-he! Have you seen t... read more

FoxyHosed January 29, 2021 80%

Becoming Carla's Girlfriend

Carla and I were watching Netflix at home just relaxing after a long day of work. I remember laying down next to her and looking at the pink toenail polish on her feet. I taunted her as said "I could do a much better job painting your toes than you could." Carla smirked and said, "It's much ha... read more

lacemint August 19, 2023 75%

A Crossdresser Gets Fitted

Not long ago I was out shopping and stopped at one of the clothing outlet stores that I frequent when looking for sexy clothes and shoes to wear when I go out clubbing or to wear in my adult videos. I was looking through the display rack of my favorite brand of pantyhose, trying to find the colors I... read more

shemale lover February 25, 2012 100%

On the Run

“Your first mistake was stealing hundreds of thousands of dollars from me. Your second mistake was thinking you could get away with it.” As I stood trembling before his desk, Mr. Atwater regarded me as if I were a bug on the windshield of his Lexus. “Do you have anything to say for... read more

shemale lover September 1, 2012 90%