Free Shemale Stories

They shaved me and put me in make up

Having crossdressed enjoying all the nice feelings of being a CD for many years.Katie is used by my longtime female partner as my name and she enjoyed me as a small cocked girlyboy as well as a now mature father ! It has now just happened somehow so quickly but in a blink of an eye it seemed to pu... read more

katieboy52 June 4, 2013 63%

A Holiday Job

'Bye!' Paul stirred briefly in bed as his twin, Anne, called out as she dashed from their holiday apartment. Paul glanced at his watch; it would be a rush but she should make it to the airport in time for her flight back to England. They had been on holiday at a popular Mediterranean resort fo... read more

shemale lover March 9, 2012 100%

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%

First time dressing up

I was always interested in women's clothing. I don't know what it was but it just made me wonder what it was like to be a girl. When i was 15 i finally gave into my curiosity and wanted to browse my s****rs clothes. I went into my s****rs room when the house was empty and opened up her closet. I saw... read more

shemale lover July 27, 2014 82%

Growing up CD

Peter, Max and I played together like that for the rest of the weekend. We must have sucked each other's cocks at least 10 times over the three days. Peter and I were both physically drained. Max just seemed to be insatiable for our bodies. He didn't want us to go. He kept on saying how much he ... read more

shemale lover December 4, 2011 33%

My First Sissy Meet Up

I had posted an add on craigslist asking people to let me suck them off at my place. After sorting out all the answers that I got I found a guy, John, that was incredibly eager, we agreed a time and date. The day came and I woke up so nervously. But I was determined to not let it show so I got... read more

Felicia Smith June 8, 2016 81%

Brewing Up A Storm

This short story is based on the two characters that were in my first story Elaine and Me. Some years have elapsed and they are still in love. I think that this story might illustrate the prejudice experienced by TS women everywhere. If anyone has any comments then please let me know. "Darli... read more

shemale lover September 19, 2012 100%

Wife and BFF Set Me Up!

I was married to a beautiful woman a few years back...I'll name her Tammy in this story (or she would kill me otherwise). Tammy was very sexual as we were dating and for about a year after we got married, but after that, she was pretty much untouchable. I thought it was me but as it turns out, it... read more

shemale lover October 24, 2012 100%

My aunt made me a transvestite

My aunt and uncle lived two doors down from me when I was growing up. They had a son one year younger than me. We played together all the time and I was at his house or him at mine all during the summer months. My aunt was a big woman, she was 6ft. tall and weighed around 165. She was even taller in... read more

shemale lover August 9, 2013 69%

Dress Up For The Girls Next Door Part 2

“Hot enough for you?” I looked up from the garage to see Lisa hanging her head out the window. She had a sexy turquoise halter on. Her tits bounced back and forth as she spoke. “Now it’s real hot with you hanging out the window.” No bra, Lisa never wore a bra when it... read more

shemale lover November 19, 2012 100%

Interracial Sissy Story

(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... read more

shemale lover May 1, 2015 93%

Catching Up

It was with mixed emotions that I listened to the message on my voice mail. It was the familiar sound of Mark, a long time friend whose call I had missed earlier that afternoon. Now as I heard it, for the third time, I felt my stomach slowly relax from the uneasy twist that had taken hold the minute... read more

shemale lover March 29, 2012 100%

Catching Up

It was with mixed emotions that I listened to the message on my voice mail. It was the familiar sound of Mark, a long time friend whose call I had missed earlier that afternoon. Now as I heard it, for the third time, I felt my stomach slowly relax from the uneasy twist that had taken hold the minute... read more

shemale lover June 4, 2012 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%

Caught and liking it

Synopsis: after being caught by mum, then auntie, auntie takes over my exploration of my femininity. Aunt Teresa had a friend in psychology. She scheduled a meeting and this lady talked to me for several hours. In short, she informed auntie that I had gender confusion and seemed to relate more to... read more

shemale lover July 4, 2012 100%

The Developing of Emma Part 6

As the weeks went by, Emma was subjected to many rituals before a crowd of masked leering males. Each day she was kept caged and plugged; her dosage of pills never forgotten. Each day Emma felt more and more feminine; one morning Elaine had her stripped naked except for cage and plug, and led her be... read more

shemale lover August 27, 2012 75%

My meeting with tranny milf Sandy 54

Wanna tell you about my meeting with Trannymilf Sandy 54! I met Sandy through an add in a pornographic magazine I was 23 then so she was 31 years older than me. Wanting for long to meet a much older tranny beauty I got really excited when she agreed to meet me. We met in her apartment after I ran... read more

shemale lover October 13, 2012 100%

Shocking shemale surprise

I had been out with friends partying after a professional basketball game and reached my hotel around 12:00 I wasn't yet tired and not needed anywhere the next day I decided to call for a massage. I had an adult newspaper and really didn't read the add. I basically called the first number I came ... read more

shemale lover June 25, 2013 95%

My Story...

Hy my name is Noemi and this is my story... I was nearly five years, my parents sleep and my sister stayed overnight at a girlfriend. I allways looked at her tights, skirts, dresses and shoes admiring (she is six years older)and i was jealous that she could wear such beautiful clothes. I liked to ... read more

Noemi27 July 22, 2013 66%

Shocking shemale surprise

I had been out with friends partying after a professional basketball game and reached my hotel around 12:00 I wasn't yet tired and not needed anywhere the next day I decided to call for a massage. I had an adult newspaper and really didn't read the add. I basically called the first number I came ... read more

shemale lover August 9, 2013 89%