Crossdresser Chastity Stories

7,593 results
Orientation
Length
Source
Infinite Scroll

Vacation with Aunt

by Alice Dragonslayer on Mar 19, 2018
Transsexual

Hello, you are 18, semi long black hair, feminine build, shy and submissive. You visit your Aunt Katy (looks like Katy Perry) for the summer. She may or may not have a daughter. She has a very feminine house and has a pink car. She dresses pretty hot. Her breasts are perfect and she's in her 30's. She doesn't have a husband and stays in an apartment with one...

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sissy's life

by cdbaby on Apr 20, 2018
Fetish

INTRODUCTION: (sorry the way it was originally seemed unclear) Sissies, they're all over the world, and beyond. Discover their origins, their fears, their lusts.What's next? halloween vinny Messaging with a dream Trendsetting slumber pary Are you my Mummy? What's next? halloween vinny Messaging with a dream Trendsetting slumber pary Are you my Mummy?...

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Crossdresser Evolution Ch. 03

by pantyhigh on Jun 12, 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...

Passion over Lust

by sarahchica96 on Sep 5, 2018
Transsexuals & Crossdressers

Introduction I' am living the dream, the dream of maintaining the balance as a regular straight guy and my bisexual crossdressing side Sarah. The 4 years of hard work at University started paying dividends, I landed a job as a legal advisor for one of the top businessmen in London Mr Hayat. My job paid well which enabled me to buy a studio apartment via a...

My Brother, My Sister Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

I wrote this story originally under the title "Be Careful In the Park" about an older crossdresser who meets a street gang in a park and gets more than she bargained for. There was no incest in the original version. I like this version better as it includes all my peccadillos: incest, crossdressing, nylon fetish, and forced sex. A warning to those who find t...

Best Camping Trip Ever Ch. 04

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

*This is a work of fiction. Most of my stories are true, but I do have unrealized fantasies...that I'll try to make reality...hope you enjoy!* *Note-this is part four of my story entitled 'Best camping trip ever for CD'...if you haven't read the first three parts, or at least part two and three, you won't understand what's going on at first. I don't like to...

Michele Nylons' True Stories

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

Introduction For those of you who only read fiction I suggest that you go directly to my autobiographical sex stories contained later on in this essay; but what I thought I would like to do is to take a break form my usual 'physically forced' and 'caught with consequences' Transvestite sex stories and write some of my musings about Transvestism and share wi...

Several Stories from Somewhere Else

by Freyasbearn on Mar 11, 2018
Fantasy

This is the landing page that will take you to the several stories re-archiving here. I am also using this section for new stories with the same themes as my other stories. That way I don't have twenty different stories all over the place that cover the same stuff. You can get it here. If you want to add on, or take a story a different way-- please, please d...

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Unexpected Delivery

by Spindizzy on Aug 21, 2017
Fantasy

You wake up to the early morning sun shining through your Venetian blinds, directly into your eyes. You throw off your blankets, open your closet door, and dig through the clothes on the floor. Searching until you find your least pair of dirty pants. You get dressed not bothering to change your boxers and head into the kitchen through the eerie silence of th...

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Matt Becomes Mattie Ch. 05

by clarepanties on Sep 14, 2017
Transsexuals & Crossdressers

The rest of the weekend was fabulous. I will not go into all the details here, unless you ask me to, except that we had a wonderfully relaxing time. The food and hotel were good and the room warm and comfortable with a lovely bathroom. We took some walks, a short visit to antique shops, but most of the time was spent reading, watching naughty DVDs, and for m...