Crossdressers Chastity Stories

18,166 results
Orientation
Length
Source
Infinite Scroll

Trailer Trash Tranny Ch. 02

by Travel_by_day on Sep 26, 2017
Transsexuals & Crossdressers

Chapter 02: Truck Stop Jeannie grew up poor in a trailer park just outside Omaha. That made it tough at school. So did being born with the wrong gender. She was a girl trapped in a boy's body. Even though as a kid she only dressed up as a girl in private (what little there was of that in the small trailer she shared with her mother), it was obvious to every...

High and Low Ch. 11

by bisexualsmoker on Sep 16, 2017
Transsexuals & Crossdressers

One could say Terry became Simon's first gay boyfriend. The muscular blonde drop in center social worker had taken the lost boy under his wing. He was giving him a degree of confidence it seemed. Very feminine, now thirty year old Simon, didn't feel so completely lost anymore. He was now well known at the West Holly Wood drop in center where he hung out. He...

Summer Ch. 02

by princessnocturne on Sep 16, 2017
Transsexuals & Crossdressers

I didn't sleep at all that night. Philip's ultimatum, and the implications behind it, danced hatefully in my mind every time I closed my eyes. I was petrified imagining what he might want me to do. I knew it was desire that I had seen in his eyes, and it didn't take a genius to figure out where the next day's activities were likely to lead in light of that....

I Visited My Sister In-Law

by SarahCD on Sep 13, 2017
Transsexuals & Crossdressers

I went over to my sister-in-law, Alison, for a casual chat. We had always got along really well. She was my wife, minus my wife's attitude towards me. We sat in the living room and chatted over a glass or two of wine. Then the buzzer on her clothes dryer went off. She said, "I need to fold my clothes while they're still warm." I followed her into the laundr...

The Ffitch Nortons Ch. 02

by RickyRooster on Sep 16, 2017
Transsexuals & Crossdressers

Notes for the Reader This is the second chapter in a series describing the sexual experiences of a young man through University and his relationship with a hedonistic family with whom he becomes more than acquainted. There are some elements of my real experiences and fantasies woven into the series but overall it is a work of fiction. All characters depic...

A New Life

by alwaysreadyfryou on Sep 13, 2017
Transsexuals & Crossdressers

Hey guys. Hope everyone is enjoying the series so far! With this being a tranny story, we are skipping over the details of his time with the Majin. It will be referenced to heavily, but we are focusing on his time with the shemales! Enjoy! Tommy was exhausted. He had spent the last two days with the Majin and the reality of his situation had finally set in....

A Failed Escape

by alwaysreadyfryou on Sep 13, 2017
Transsexuals & Crossdressers

Tommy woke some time later, not really knowing the time. For all he knew, time wasn't real here. It was dark though, so he assumed that there was day and night here. He reached for his wrists, and felt the shackles on them. However, there were no chains binding him to anything. He nearly exploded with joy at this revelation, and slowly got up off of the pill...

Barrack Room Betty Ch. 04

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Four - A Night at the Flicks Michele was confused; she didn't like Leading Recruit Jason Jones one bit, he was a bully but he was also handsome, strong and actually quite intelligent. She knew he had a thing for her as soon as the Leading Recruits made the grommets crossdress, and of course last night he had ejaculated in his pants when he was span...

Hotel Porter to Private Maid

by KinkyBiLad on Sep 12, 2017
Transsexuals & Crossdressers

This is my first story, please leave comments below and tell me what you think, I hope to carry on the tale, if the readers like it. I suppose I should explain how I got like this. How an ordinary guy who was a porter in a hotel became the sissy, dressed as a maid, with a butt plug firmly inserted into my tight sphincter, on my knees, and throbbing 8" cut...

Caught by the Past Ch. 02

by Tomsparty on Sep 14, 2017
Transsexuals & Crossdressers

Chapter 2 - Tight or Loose Previously - After a drink with a new friend he invites you back to his house. Strangely drawn to this handsome guy he persuades you to dress in girls clothes... Now You're wearing a sexy leather mini skirt, fishnets and high heels, your cocks like rock and you're just about to show yourself... At the sight of James, you get a se...