Chastity Cross Dressing Stories

77,281 results
Orientation
Length
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Infinite Scroll

Delving into Femdom Ch. 02

by readytokneel2907 on Jun 1, 2020
BDSM

**Chapter 4. Navigating the Next Step The next day I awoke and had to go to the mirror to confirm if my ass was red or if this was all really a dream. However I had actually had my first FemDom experience and my head was racing. The encounter with Mistress Veronica was so vivid I could recall every step that occurred last night. I wasn't sure what my next m...

The Halloween Party

by DMaster_14 on Sep 13, 2017
Erotic Couplings

The Halloween party was to start in 3 hours and my husband called me into our bedroom to get dressed. I had already showered and shaved so this was no problem. My costume was on the bed, what there was of it. We had decided that a pirate theme for this year would work for us. My husband would dress as a Captain and I would be the haughty noble woman captured...

Free Day

by Joephus511 on Mar 20, 2018
Loving Wives

'Last Day': Late in the day I'm locked in my chastity cage. My wife checks the brass lock and all the rings to make sure the cage is secure and I can't get free. A half hour before being locked in I masturbate into a small plastic container and my wife puts it in the freezer. Most months I will eat the contents of the container shortly after being released f...

X.S.X Experiment

by njcaptionlover on Apr 4, 2018
BDSM

All characters are over the age of 18 years old. ***** Hello. My name is Justine, and I'm a 25 year old single male whose fetish curiosity had finally gotten the best of me. My owner granted me permission to recount my story. I started collecting Playboy magazines at an early age. When I had my first computer at the age of 18, the world of porn opened...

The Captive Prince

by PrinceCai on Apr 3, 2020
Fantasy

Marcus was reading in bed when his kingdom fell. It was over an hour past his bedtime, but the young prince wanted to stay up and finish his book by candelight. It was way too exciting a story to put down, all about a brave and noble lady knight who saved a peasant boy from the clutches of an evil sorceress. He had his heart in his mouth at the thrilling act...

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March Madness Ch. 03

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

Adversity in Buttermilk Falls

by justincbenedict on Sep 17, 2017
BDSM

When Blume and Chloe got home from their BDSM party, they were still shaking their heads over the odd goings-on at the dinner party. But Chloe had a funny smile on her face. "You know, Blume... What's this porn stuff about?" Blume blushed. "Chloe, you have to understand, there's fantasy and there's reality... The whole chastity thing is kind of a fanta...

Arcadia Castle Ch. 09

by Hal1031 on Jun 26, 2019
BDSM

Chapter 9: A Visit to Dr. Chastity Each of the chapters in this series may be enjoyed as standalone stories, but the events and characters are richer within the context of the whole story. ------- I was startled to find Cole stretched out on my lounger the next morning, his intense gaze trained on me as I attempted to stir myself awake. "That's a lit...

Made to Obey Ch. 10

by madetoobey on Aug 6, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). I'd been forced into a chastity cage and made to wear panties all the time. Humiliation was now a frequent event. Esther, who had investigated my internet usage on my laptop to see if I'd visited shema...

A Trip to Remember Ch. 01

by marykay9 on Sep 16, 2017
Transsexuals & Crossdressers

I live in Los Angeles and don't get much of a chance to practice my hobby of cross dressing. Once per year however, my company sends me to an industrial convention and I take full advantage of the opportunity. This year I was to travel to San Antonio, Texas, to attend a conference at a large hotel located on the River Walk. I packed two bags, one with my b...