Free Shemale Stories

A Natural Sissy Part 3

The Reward Once we were at home, I still couldn't keep Stacy quiet. "When do I get my reward, Mistress Gail?" repeated every other breath. Constantly. Finally, after I had changed into my bedtime attire (a pair of 4-inch heeled mules, and a see-through short nylon robe, in pink, like my... read more

shemale lover March 24, 2012 100%

Buying Time

It’s a hundred dollars to use the sex machine in the public restroom. Insert a couple of fifty-dollar coins into the payment slot to remain anonymous, though of course it’s more convenient to just let the data terminal do a neural scan and auto-debit your account. A hundred bucks buys... read more

shemale lover March 25, 2012 100%

Planet Of Men

At 1600 Eastern Standard Time (EST) on September 27 in the year 2020 AD the UN announced that General Atomics Corporation (GAC) had saved the world. After years of panic in every country that the world was doomed due to the effects of global warming, GAC announced that, with funding provided by the ... read more

shemale lover May 4, 2012 100%

Betrayed Chapter 4

I really wasn't surprised when Dianna directed me into the parking lot at Ringers. It was only a few blocks across town from my new home; a five-minute drive, if the traffic wasn't killing at the time. Consciously, it had not been a factor in my decision to take the new place. Sub-consciously... wel... read more

shemale lover May 29, 2012 100%

Fender Bender

It was the first week of June and school was out for the summer, I was 18 and had just finished my Senior year. One night while we were eating dinner, My Mom and Step dad informed me that they were going away for a week. When they got married they did not go on a honeymoon so they wanted to take one... read more

shemale lover July 26, 2012 100%

Fender Bender Chapter 9

My name is Robert, I have been cross dressing since I was 14. I turned 18 last summer and this story takes place during my senior year in High School. I am 5'9" 160 pounds, blonde hair and blue eyes. When I am dressed I call myself Vicki. __________ I had met Julie at a recent party. Well... read more

shemale lover July 27, 2012 100%

One Special Night

Marilyn called me at the office with just three words. "It's on tonight." After a few moments of listening to the silence on the other end of the disconnected call, I realized what she was referring to. Immediately my cock began to swell, sliding slowly inside my satin panties unti... read more

shemale lover September 2, 2012 100%

With an 'E' Chapter 2

Waking the following morning, feeling somehow fulfilled. Then, as I came to, I remembered the night. With my frilly shortie nightie disgustingly clinging to my body, back and front, came the realization "I was no longer a virgin!" And -- it felt great. Sometime in the night, Bobbey had ... read more

shemale lover October 10, 2012 83%

Alleys

My mother told me never to take a girl into an alley at night. She went on about how dangerous they were, with strangers lurking in dark doorways waiting to do horrible things to the people who wander in alleys. Alleys can be dark, imposing and dirty especially in the city. I spent my youth avoiding... read more

shemale lover October 14, 2012 100%

First Time for Everything

At the time I was living in Paris and on sheer whim, I decided to go to Amsterdam for the weekend. I thought to myself, "what better place to act out my fantasies than in Amsterdam?" I packed some of my slutty clothes. I decided on my slutty cowgirl outfit complete with flannel top, jean s... read more

shemale lover October 14, 2012 83%

Double Wedding

I was about to marry my childhood sweetheart Paula Rother. I loved her and she loved me but it hadn't been straightforward. After school she went to Manchester University while I went to work at a local accountants as a lowly paid junior clerk. She said we where inseparable but during the two years ... read more

shemale lover November 8, 2012 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%

The Meeting of Cortney and CiCi p1

Cortney could not keep herself from thinking about the upcoming date with CiCi as she sat in the luxuriant bath water and shaved her legs. She planned to fuck the glam slut whore long and hard. But first, the metamorphosis to turn her into the dome bitch - Cortney. She rose from the bath, patted... read more

shemale lover April 15, 2013 100%

Pounded to submission part2

Two days ago Joesph was checking out porn. A couple of BBW vids here some interracial there, the usual. Then he saw a just viewed picture with a Brazilian She-male and couldn't stop looking. With his curiosity getting the better of him he clicked on it. She was gorgeous! Her face appeared to be as f... read more

shemale lover April 21, 2013 100%

My second time

after failing to loose my virginity,i decided to try again. my man friend love to fish and would make his way to inch early every sat morn. being a creature of habit he always returned at the same time. one sat evening i accidently on purpose bumped into him on his way home. standing at the side of ... read more

shemale lover July 21, 2014 100%

Amara Vadillo ( Sylvia Boots )

Vadillo was born and raised in Cuba. After emigration to Los Angeles she became Amara. After injections of hormones and silicone, she was a 34 DDD. She found work acting in shemale videos and performing at the West Hollywood Club 7969 under the name of Sylvia Boots. She became known for her love of... read more

✘Transensual✘ October 10, 2017 51%

Wife Left Me so I Could be a Girl

I Am The Girl My Wife Did Not Want As the only child of a single mother I grew up around all things feminine. Having lingerie and stockings drying in the bathroom was normal for me and I always loved how pretty the full cut nylon panties and slips with tons of lace looked. I lived at home with... read more

ASSEaster5678 July 9, 2018 83%

Le rire du « sergent », la folle du régiment

En France, « Le rire du Sergent » est une célèbre chanson du talentueux Michel Sardou, Pour moi c'est plus qu'une chanson, avec quelques variantes c'est mon histoire. En effet autrefois les jeunes français effectuaient ce que l'on appelait le service militaire pendant une an dans une caserne, La... read more

Madame de Parme January 27, 2020 100%

HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH

It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... read more

CDDIXIE4U January 8, 2019 100%

BANGING AROUND BANGKOK

BANGING AROUND BANGKOK: THE AMOROUS ADVENTURES OF CAITLIN "MEOW" MORRISON after living and working in Thailand/SE Asia for many years i decided to write an erotic story based on some of the people i have known, venues and places i have been, and the P4P night-scene where i spent way too much... read more

bkkldby June 17, 2019 85%