Free Shemale Stories

Caught in the Act....

One summer, my cousin Nancy came to stay with us for a while, as her parents had gone away on a cruise trip. At 18 years old, she was a couple of years older than me and in the full bloom of her young womanhood, so to speak. She knew it, too, and it was obvious that she had no problem at all in pull... read more

shemale lover September 26, 2011 100%

My Psychology Of Been A Cross-Dress

It has to be said, why this was wrote I am not sure, I am finally beginning to understand the journey I began at the age of six and perhaps doing it this way helps. It's a short narrative, that attempts to explain my thinking and the frustration of accepting who I am. This is not an erotic story;... read more

shemale lover September 30, 2011 50%

Caught cross dressed Part 1

My name is Philip. I am married to a beautiful woman called Helen, and a few days ago... I did something very stupid! My wife, her mother, her beautician, my P.A. from work, and any of their friends, (in fact, anyone that they choose,) are now completely in control of my life. They are my Mistres... read more

shemale lover October 2, 2011 75%

Turned into a Toy

I clicked the lock shut on the locker containing all my clothes and looked down at my now naked body. I was in very good shape for a fifty year old. I'd always been thin and now I was shaved from the ears down and all six feet of me looked smooth and toned. My cock was a bit tumescent, larger than a... read more

shemale lover October 3, 2011 75%

Summer whoring Part 2

She kissed me with a deep wet kiss. She touched my tits through my dress and pinched on my nipples. Then she slid her finger between my already wet pussy lips. I was trembling from excitement. She asked me if I want to continue this at her place and I agreed. She took me by my hand and led me to ... read more

shemale lover October 3, 2011 100%

Caught cross dressed Part 2

"As Pippa is now completely unable to move her head... I think that we should begin with her eyebrows." Alice told the others. The others each nodded their consent, and Alice began her work on me. My already thinned eyebrows were plucked pencil thin, and were shaped into a high arch ove... read more

shemale lover October 7, 2011 66%

My shemale mother!

I am 35 years old and had always been living with my mother, who is almost 50 since my father left us 20 years ago. I am not sure of the reasons but I do know that my mother is an average looking woman with nice looks and a not so fantastic body. Her pear shaped figure is a norm for any woman with I... read more

shemale lover October 7, 2011 62%

Sight Unseen

"People do not see that at which they look." Professor Emile had just projected a series of ten young female nudes upon the screen. Asking us to study them carefully, he'd left each enlarged photograph on display for three minutes, treating us, for half an hour, to these magnificent ima... read more

shemale lover October 8, 2011 100%

The House of Lesslie Part 2

I. I woke up. Even after having taken over the House of Lesslie weeks ago, each morning was still the same, and came with the same feeling of disorientation, in need of a few moments to adjust to the realities around me, as new as they were. The bedroom around me was still darkened by heavy... read more

shemale lover October 14, 2011 100%

Bewitched, Bothered And Bewildered Part 3

RULES OF THE GAME Where Vivian's mother lays out exactly what she expects from her son if he wants to keep her onside and help him to achieve his dream. Vivian went into the bedroom with a towel wrapped around his waist. He was whistling, there was a spring in his step. "You've been ag... read more

shemale lover October 15, 2011 50%

The Zodiac Coins: Libra

2400 YEARS AGO... He was a humble shepherd. It was night and the flocks were sleeping. As he gazed at the stars, he saw a shooting star. He knew it was a portent of some kind, but was not mystic enough to know what. A little while later he saw another shooting star and guessed that wha... read more

shemale lover October 18, 2011 50%

Transvestite in trouble - the internet porn quee

Bright light filled the room, waking me from my unconciousness. so bright it took a while for my eyes to focus. When they did the first site i saw was myself, in the wall sized mirror opposite me, strapped to the chair. It was me only now i had masses of long blode hair, tied up in 2 pigtails, lo... read more

shemale lover October 22, 2011 100%

Daddy's little bitch

As a young boy growing up I always had a fetish for dressing up like a girl. When I was 20yo I had my first experience with an older man, Tony a man in his 70s. I met him through a phone chat line and we seemed to hit it off right away. He told me that he would buy me some clothes and lingerie to we... read more

shemale lover October 25, 2011 66%

Looking-Glass Ladyboy

I was taking a walk to stay--all right; I'll admit it--to get in shape, when I saw the "Going Out of Business" sign in the second-hand furniture store a block north of my condo. I wasn't in the market for anything, new or used, but I can't resist a bargain, and what was better for finding ... read more

shemale lover October 29, 2011 0%

You've Got Shemale

This is my first story of this type, so please, be gentle ;) It's a semi-true story, but definitely more fiction than fact, and it will be at least two parts. I moved to a smaller town when I was in college and found that I didn't fit in at all. I actually got so lonely that I took up a friends... read more

shemale lover November 1, 2011 87%

First fuck for Freda

I'm such a slut. It's not easy to know where to start. I suppose my routine - that's what got me into this, I guess. Each morning, after my mother went to work, I had three or four hours before my shift at the factory started. I would get the box from under my bed and dress myself. The stockings,... read more

shemale lover November 2, 2011 100%

Alpha Gamma's Secret Part 2

-4- Molly awoke to the annoying sound of her alarm beeping. Groggily, she reached over to her night table and turned it off. It was 7:00 AM, way too early for a 19-year-old college girl to be awake, in her opinion. As she stirred, her girlfriend wiggled up against her, eager for body heat. ... read more

shemale lover November 2, 2011 100%

Innocence

I had just gotten off the train from my work, and now I was standing outside of the station, waiting for my bus in the freezing cold. I wasn't overreacting; it was really cold. I was wearing a thick winter coat and gloves, but I wished I would have remembered to bring a scarf or something, because I... read more

shemale lover November 4, 2011 87%

Dressed in holiday style

I watched the speed limit, which is unusual for me, as I pointed the car west towards the Evil City. It was about 1:30 a.m. and dark on the interstate that stretches across the prairie, so I was wearing a black mini-skirt, fish-net garter stockings and my four inch stilettos as I drove through the n... read more

shemale lover November 6, 2011 50%

The Bottles

Fred shivered in the cold winter air. With his head down and feeling very self-conscious, he trotted out of Birmingham New-Street station in the strappy high-heels and headed down the road as he had been instructed. He couldn’t believe he was doing this. It wasn’t that it was the first t... read more

shemale lover November 6, 2011 50%