Sissy Crossdresser Stories

7,061 results
Orientation
Length
Source
Infinite Scroll

Crossdresser Evolution Ch. 05

by pantyhigh on Aug 7, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties. Though there was still a feeling of shame surrounding it, I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's pantie...

Becoming a Sissy Maid & Slut Vol. 06

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Twelve: Chantel's day off. Ohhh, and ahhh as I awake and stretch in my bed. Mmm a blissful sleep where I see the clock and that it's actually 10:00am. At first I freak out a little bit as it normally would be very late for me. But I soon realize Master has allowed me a blissful and free Sunday off. I then get out of bed, my butthole is sore from the...

A Morning's Service Ch. 02

by Philippasubmaid on Dec 10, 2017
Transsexuals & Crossdressers

This story is a graphic tale of a Dom and his very submissive crossdresser. If you are offended by tales of BDSM and sex between consenting adults then read no further... other wise enjoy. Feel free to leave honest comments or suggestions, it really does encourage those of us who write to continue... ***** As I laid on the floor I strained to hear what m...

Sissy Maid to Be... Ch. 03

by missjennymaid on Apr 8, 2019
Transgender & Crossdressers

I would recommend reading the first chapters to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jere...

The Writer's Secret Ch. 01-02

by AnnMichelle on Sep 13, 2017
Transsexuals & Crossdressers

Hi everybody! This is one of the many stories I've written over the years. I've decided to clean them up (read: edit the heck out of them) and start sharing them. This one has some light-femdom, a pretty willing husband, and a few fun surprises. Enjoy! * Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor...

Sarah Had to Give a Blowjob

by SarahCD on Dec 18, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. ---------------------------- After collage, my girlfriend's best friend, Alison, and I found ourselves working in the same city and...

A Crossdresser Gets Fitted

by Vennessa on Sep 16, 2017
Transsexuals & Crossdressers

Not long ago I was out shopping and stopped at one of the clothing outlet stores that I frequent when looking for sexy clothes and shoes to wear when I go out clubbing or to wear in my adult videos. I was looking through the display rack of my favorite brand of pantyhose, trying to find the colors I wanted in my size, when I noticed a cute guy checking me ou...

Stood Up Pt. 01

by LadyJae01 on Jan 21, 2020
Transgender & Crossdressers

I hate bars, especially being alone in one. So, I make the best of being stood up. I pretend like I meant to be here, all dressed up, in a slinky, off the shoulder red dress, by myself. I migrate from the bar to an open booth, so I can people watch more easily. As I walk, I have to tug my dress down my thighs as it tries to ride up. Nothing is ever quite lo...

The Bargain Dress

by HeatherMaureen on Sep 25, 2017
Transsexuals & Crossdressers

I was in my late teens before I found out how submissive my dressed self was. I'd never really considered myself to be a submissive sissy crossdresser but was about to discover that I was one. I called an ad about women's dresses, heels and other things in the local bargain finder from a payphone. An older woman answered. She wasn't taken aback by my tellin...

Becky's Video

by purekink on Sep 13, 2017
Transsexuals & Crossdressers

I suppose I was the one that first mentioned porn to Nikki. We'd been chatting on a girls' night out and laughed abut how I'd never found any porn in the house. She giggled and said I was bound to find some sooner or later -- all men had some, somewhere. A few days later, I'd completely forgotten our drunken conversation and so when Nikki showed up at mine...