Free Shemale Stories

Adventure with a Couple

A friend of mine, who thinks that i lead an exciting sex life (okay, i DO, lol) has asked me to relate an incident from my experience where i had a session with a couple. So, R, here goes. i guess i should relate a bit about myself, so that you understand how this affair took place. i am a 41 yea... read more

shemale lover October 15, 2011 100%

Tony to Tanya

My name is Tony and I'm an average 19 year old boy. I'm 5 foot 7 inches tall, have shoulder-length brown hair and blue eyes. I often get mistaken as a girl from behind because of the length of my hair and because I look after it really well. I've been told I'm as good-looking as most girls my age. M... read more

shemale lover December 19, 2011 100%

Debbie Part 5

Debbie didn't wake up until her gag was wrenched from her jaws. Her hood, collar and earplugs had already been removed. "Wake up, shit-head," Mistress spat and slapped her face hard. Debbie came awake and noticed that all the straps holing her to the couch had also been removed. She felt a... read more

shemale lover December 22, 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%

Becoming A She-Males Bitch Part 2

After last nights ordeal I was given something to drink and taken to a bedroom upstairs. What I drank must have had some kind of drug in it because I was knocked out. I bet I was asleep in just a couple of minutes. I barely even remember lying down. When I woke up I was naked, sore as hell and fe... read more

shemale lover January 4, 2012 100%

My wife and I switch roles

One night my wife Stacey and I were laying in bed. She told me that she had a dream that she used a strap-on dildo on me. She told me that she would like to try it and started to rub my cock. I started to get hard as she started to talk dirty. She went down on me and started to suck my cock. When I ... read more

shemale lover April 9, 2012 100%

Amanda and Me Chapter 2

I rolled over after reading Amanda's note with a big smile on my face. I couldn't believe that after all the time I had spent masterbating to shemales and fantasizing about meeting one it had actually happened. Not only had it happened but it had been the most amazing sexual experience of my life. ... read more

shemale lover October 21, 2012 100%

Anastasia's Life

Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember, not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barb... read more

shemale lover November 26, 2012 100%

Anastasia's Life So Far

Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barbi... read more

shemale lover November 27, 2012 100%

Young Sissy Chapter 1

I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a man, just to s... read more

shemale lover January 4, 2013 100%

Lady and the Cop

A cab pulled up to the front door of the Orbit Lounge bar and three curvaceous figures, Regina, Alice and Rita stepped out, paid the cabbie, and moved gracefully towards the main entrance. They were all so jubilant and any observer would suspect correctly that they were already under the influence. ... read more

Regina10 March 2, 2018 100%

I Give Up

The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... read more

ASSEaster5678 September 14, 2018 100%

Continua mi mundo Tv

Como les decía a mis 20 años ya era otro mundo, ya compraba mi propia ropa intima femenina mas que todo ropita muy chica, pues siempre he sido muy delgad@, a esta edad aun era virgen pero con hombres ya que aproximadamente a los 17 le robe un consolador a una tía, "les admito que ha sido uno de ... read more

Carla Travesti December 10, 2018 100%

janine 2

After my epiphany, after my fainting, after my two near consecutive, mind melting orgasms, I was ready to meet the world with new resolve. No longer would I keep my true self under wrap. I was ready to become Janine, however I was going to have to be cautious, for the time being anyway. The first th... read more

bunny cat February 8, 2019 100%

Lady In The House Ch. 05

A story by MicheleNylons (Crossdressed prisoner is forced into prostitution.) From Part IV Then Eddie looked down at my body and noticed the semen pooled at the front of my panties. My semen! He looked down at his tight belly and saw a slimy stain that was the result of my ejaculate spread th... read more

✘Transensual✘ February 25, 2019 100%

Mi primo y yo (2da parte (historia con mi vecino))

Bueno ahora toca el turno a la historia que les prometí con mi vecino. Recuerdo bien que todo comenzo un dia que mi primo y yo estábamos solos en mi casa como de costumbre por uno de los tantos viajes de mi familia, ese día me arregle super linda para mi hombre pues había comprado un conjunto de ... read more

Janin December 27, 2019 100%

Weekend Fantasy

have so many fantasies....the one that gets me lately, is having access to a house out in the middle of nowhere, for a week or weekend, where i can dress up, all day. No one knows of my lustful secret....so the idea of being able to stay this way without thought, gets me so hard and such in the moo... read more

martley July 20, 2020 100%

Camming down the rabbit hole Ch3

Slowly stirring from my sleep, I stretched under the covers and a pleasant sensation spread across my torso, remembering what I was wearing when I went to bed I smiled at the caress of the fabric on my skin. It was a strangely comforting feeling, the pressure from the bra, panties and nightie felt l... read more

Dani_does_Dallas August 18, 2021 100%

Camming down the rabbit hole Ch4

It was the morning after the night before, and as I stretched under the bedsheets, a smile spread across my face. Remembering last night’s events, I felt myself stir a little and pressure from the panties I had on adding to the arousal. It has been a while since I had morning wood after a big show, ... read more

Dani_does_Dallas September 6, 2021 100%

Camming down the rabbit hole Ch5

I was jolted out of my sleep by the phone on my bedside table vibrating, bleary eyed I picked it up and saw a message from the couriers that a package would be delivered today around 4pm. The realisation that this was the package I had been waiting for and I could finally wear something else in my s... read more

Dani_does_Dallas September 29, 2021 100%