Crossdressing Chastity Stories

7,823 results
Orientation
Length
Source
Infinite Scroll

Set Up Ch. 01

by Sissy_Ashlee on Sep 15, 2017
Transsexuals & Crossdressers

This is my first attempt into writing an erotica story. This tale will contain themes of female domination, crossdressing, and eventually MM sex. If any of this is not you thing, please scroll on. Otherwise, please let me know how I did. ***** Since I was a teenager, I had been bicurious. Not really interested in men, but what is between their legs. My obs...

Becoming a Sissy Slave

by mikhaylacumme on Sep 16, 2017
Transsexuals & Crossdressers

He gave me the choice. He had programmed me for a week and knew which way I would probably choose, but he gave me the choice. I could get out. Or I could continue. It was up to me. On my knees or out the door. It was that easy. Now I had to choose. I guess I should backtrack, first. You might be scratching your head saying 'what choice?' Let me start...

Cherry Pt. 03

by Cirkle7 on Dec 25, 2019
Transgender & Crossdressers

We made it to the final installment of Cherry! You may want to read the other two first... I am working on a few more. Finding time is difficult, but I really like sharing my dirty thoughts with you all! Of course this story has no person under the age of eighteen. Thanks for the comments, I like the bad ones the best... makes me happy that I made you sick!...

Jacki's Journey into Sissyhood Pt. 03

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

This is the 3rd installment of the Jacki's Journey series. I'd like to thank those who were nice enough to add comments and feedback on the proceeding stories. I'll try and keep them cumming. ***** I had a couple days to evaluate Steve and Laura's offer and I was no closer to a decision than I had been. I went back and forth on the verdict. How was I goin...

Sissy Maid to Be... Ch. 02

by missjennymaid on Sep 10, 2018
Transsexuals & Crossdressers

I would recommend reading Chapter 1 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. Jeremy is get...

Beta Male Slave Academy Ch. 02

by Tazokm on Jul 13, 2020
BDSM

After being blown and locked, Miss Carly explained to me that the compound we were at had over a hundred rooms and approximately 50 current residents. She began walking me to a room where I was to keep myself preoccupied until they had prepared my sleeping arrangement. I walked butt naked behind Miss Carly down a high-ceilinged hallway. Her ass was absolutel...

Life and Time of Lady Vargos Ch. 09

by rik581 on Mar 26, 2019
Transgender & Crossdressers

Martin walked down the hallway at a brisk pace. Walking with a bit of exaggerated hip movement and fingers out palms down, just in case somebody was monitoring him. He had adapted quickly to walking this way and had found it not too difficult since his daily treadmill walks were done the same way. The walk was cute for others to watch, but Martin felt silly...

Caught Out, Made Over

by TanyaCc on Oct 5, 2020
Transgender & Crossdressers

It had finally happened. To be honest, I shouldn't have been that surprised. But here I was, dressed in my favourite sissy school gurl outfit, heels on, lipstick, wig and chastity cage in place, bent over the kitchen bench, getting reamed to the hilt by an 11 inch dildo on the end of my own fucking machine. I had cum dripping down my thighs, moans and groans...

Whore of the Dragon

by Conan The Librarian on Feb 19, 2020
Fantasy

There, amongst the remnants of the dead race, where their greatest queen reigned, two dragons lie dormant. One of pure evil, one of pure good, both yearning for a vessel, both lusting for a mate... She may be adequate for that purpose, our forlorn child... We shall see. "Silence, fools. We are close to the inner sanctum." The two mercenaries exch...

Open in Reader

Undercover Mistress Pt. 02

by nexomorph on Dec 2, 2019
BDSM

The first part was a bit raw. Sorry, I rushed it a bit. Read it if you want the plot. In this part I cut to the main thing. The series will contain all kinds of BDSM stuff and fetishes Have fun! *** I was in front of woman of my dreams. Aurora. Mistress Aurora. In black corset, garter belts, stockings, black thong, glassy high heel platforms, oriental hair...