Crossdressers Chastity Stories

18,166 results
Orientation
Length
Source
Infinite Scroll

Penny

by Targloyalist on Sep 26, 2017
Transsexuals & Crossdressers

I was in my sophomore year of college when I first met Penny. I remember the exact night I saw her face. It was a warm one in early October, and I was in my room on my computer. I was also wearing a CB6000 male chastity cage. I know, it sounds crazy, right? I mean, why would any guy willingly lock up his own cock? Well, I can't speak for anyone else, but f...

Caitlin and Mistress Vicky Ch. 02

by Jemina004 on Sep 19, 2017
Transsexuals & Crossdressers

I hummed softly as I put the finishing touches on the salmon. Teriyaki salmon was my wife's favorite dish and it filled me with pride to know that I was making her happy. My mouth watered slightly as I arranged the tray. (I would only be having a salad myself, as I had to maintain my figure.) Taking out a pocket mirror from my apron, I checked myself to ma...

Rosa subrosa

by ValoryG on Apr 8, 2019
Transgender & Crossdressers

I first saw Rosa on a kinky-sex dating site. I, as a 35-year-old recent divorcee, had visited it "just out of curiosity" -- or was it rather because I sought a little titillation? I certainly never expected it to lead to anything. I just thought I'd peruse some photos and fantasize about meeting some off-beat women. I ended up beating off looking at a few of...

Black Cuckolding Journey Trois

by Samuelx on Sep 11, 2017
Transsexuals & Crossdressers

Salutations, my friends and devoted readers. Wanda Philogene here. Your favorite Haitian dominatrix, taking the beautiful City of Brockton, Massachusetts, by storm. Ladies and gentlemen, I have some good news. I've dumped Sean Prescott, my favorite white dude, on account of him becoming possessive of me. Sean and I were cool, and we had some fantastic sex, b...

Sissy Cristal Used by Mistress

by mistressandpussyboy on Jan 8, 2019
Transgender & Crossdressers

This is a real life story, another day in my life with my Mistress. We were ready to go out to run some errands, when Mistress addressed me. "Plans are canceled. I want to bang a hooker: get dressed for me." No sooner said than done, I was getting naked, opening my sissy suitcase. I put on a pretty panty, black stockings, a miniskirt and my high heels. M...

My Husband a Pornstar Ch. 03

by gtanya on Mar 20, 2018
Transsexuals & Crossdressers

Please read the previous two stories to fully understand and enjoy this chapter. If you don't want to read them, here is a brief description of what has happened till now: *** My husband was conned by me into exploring his sexuality and he finds out that he is bisexual. He also agrees on being a porn-star to earn a hell lot of money for us. After shooting...

Ms. Alexandria - Interview No. 02 Pt. 02

by gasissynora on Dec 3, 2019
Transgender & Crossdressers

This is the third part of the Ms. Alexandria series and part two of The Second Interview. I believe it will stand alone, but will make more sense if you read the earlier parts of the story, particularly Part 2a. This part starts with the last paragraph of the previous part. Ms. Alexandria: The Second Interview -- A day out. Part 2b Mistress walks up behind...

A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...

My Husband a Pornstar Ch. 04

by gtanya on Mar 21, 2018
Transsexuals & Crossdressers

Chapter 4: Conclusion Here is a small brief of what has happened till now: My fairy husband had been seduced by a strong man at home and then had agreed to be a sissy pornstar. Fairy new master had trained him as a sissy to perform in a gay movie without his knowledge that he was making a sissy trainer porn movie the whole time. I found out and threatened...

BBC Worship Guide

by whiteboibbclicker on Sep 16, 2017
Transsexuals & Crossdressers

This guide is intended for every whiteboi out there wishing to please his black daddy or any black man bcz this is hi duty. First you should be totally naked with a butt plug in your ass and chastity device worn. Then you must approach him while crawling with your ass sticking out and your head bowing in humility. You should kneel in front of him and ask...