Cross Dressing Stories

72,522 results
Orientation
Length
Source
Infinite Scroll

Her Doll Ch. 01

by WickedDoll on Sep 16, 2017
Transsexuals & Crossdressers

'What would you like, girls?' Quietly amused, I smiled at Samantha who eagerly gave our drink order as we settled into a corner booth at one of his favorite alternative lifestyle bars. Or should I say her. No difference. Sam was Samantha during the weekend and I was accepting of his chosen uniqueness. As long time friends, I knew it pleased him when he was...

An Unwelcome Visit

by BabyPink on Sep 16, 2017
Transsexuals & Crossdressers

It had been over a year since I had split from my boyfriend, Rick. We had a terrible row in which he had accused me of seeing another man. He walked out, never to return. I had tried to give up wearing girls' clothes afterwards in an effort to become a 'normal' person and to try to blot out some bad memories, but the desire was just too strong. I had got bac...

Street Fair

by Rocket19 on Sep 25, 2017
Fetish

Today is the big day, the day you have anticipating for months. You have been a slave to your master for almost a year and several months ago he announced to you that you would be the star attraction at a live bondage and discipline show. He did not immediately tell you where but exactly four weeks ago he let you in on the secret, it would be at the Folsom S...

Be Careful What You Ask For...

by StephanieLGFrancis on Sep 16, 2017
Transsexuals & Crossdressers

I've been living with Janet for ten years now and for the first eight all was well. But over the last two years things have changed completely, and not for the better. I started looking at various sites over the years, you know the type, and I concentrated on cross-dressing and transvestite sites. But this would only be every now and then. I did look at othe...

Age/Sex/Location

by LeanneSinclair on Sep 14, 2017
Humor & Satire

The scene: a text-only cybersex chatroom. "MistressLisa" has just invited "bi_curious_debbie" to a private chat. The following conversation ensues. MistressLisa: Hi, how are you? bi_curious_debbie: fine thanks, you? MistressLisa: Good thanks. A/S/L? bi_curious_debbie: Sorry i'm new here. Whats ASL? MistressLisa: Age/Sex/Location. bi_curious_debbie: Oh...

Chrysalis of Kirsten

by KirstenEclipse on Mar 23, 2019
Transsexual

Date: March 22, 2019 Author: Kirsten Addison Subject: Chrysalis of Kirsten Chapter 1 By KirstensubTS My name is Steven aka Kirsten. This story is about how I went from a closet cross dresser to becoming a full time transsexual slave. This story is mostly true, based on my journals with dramatic license to make it more exciting and readable. Names have been c...

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Daddies Slut

by XxPrinceAnonomousxX on Nov 26, 2017
Group Sex

I looked around the apartment happily, the candles in the room giving off a nice glow. I knew what I was going to do tonight; I was going to really entertain my longtime boyfriend. Since him and I met three and a half years ago he'd been obsessed with my feminine body, my long red hair, and my girlish figure. I'd never really cross-dressed much before I met...

Wendy The Haitian Sadist

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

Salutations, dear readers. It has most definitely been a while, hasn't it? The name is Wendy Stefania Polydor, and I'm a young Haitian-American woman living in the City of Boston, Massachusetts. Mother of two, divorcee, college graduate and nurse, I am all of these things and more. I have been delving into the world of BDSM, and more fun things like swinging...

The Transvestite Divorce Transcript

by desireethtttv on Aug 1, 2018
Transsexuals & Crossdressers

We begin with the plaintiff, the woman of the marriage of 33 years, from hereto within known as Mrs. S. Verses the transvestite husband we shall call Desiree. Mrs. S Attorney (referred in future testimony as AFM: Please state your reason for the divorce proceedings, if you please Mrs. S. Mrs. S: I wish to divorce my gay transvestite husband due to the lack...

A Roleplay Gone Awry

by ronald81 on Sep 15, 2017
BDSM

All people within this story are over the age of 18. ***** For as long as I can remember, I have always been into cross-dressing as a young boy. Yet, I would hide these feelings deep down as I grew up. The following story is partly true, as much as I can remember. It all started when I was playing a roleplaying game featuring a text based game that was su...