Chastity Cross Dressing Stories

77,281 results
Orientation
Length
Source
Infinite Scroll

Helping Jess Pt. 02

by mski on Sep 18, 2017
BDSM

The First Date It was a bit strange driving with the chastity belt on. I had worn one before for some days, but a long time ago. We got talking about different stuff. It just clicked – as long as I forgot about the belt, or how good she looked. She asked me to go via the office, she said she had forgotten something. I did so, she came back soon after with...

Cuckolded by Kate Ch. 01

by cuckytoher on Sep 12, 2017
Loving Wives

It's 7:45 am and I'm sitting outside Target waiting for them to open while my wife Kate and her lover Michael are home snuggled up in bed sleeping. I can barely keep my eyes open considering I didn't get to bed until after 3:00 am. My CB3000 chastity device is making my cock shrink smaller than it already is due to the cold air this morning. I have a lot to...

Letter from Gander Cove

by justincbenedict on Nov 20, 2018
BDSM

Dear Shoeblossom, My teachers always said to me, "Norbert, you'll never amount to much, smoking weed and playing video games..." but I found I had hidden talents... Recently I joined a sadomasochistic group. It's a local thing. Amazingly, I met the hottest girl who wanted me to punish her! Victorine is a very attractive woman who's got about twelve or thi...

A Different Kind of Home Ch. 01

by starmanz1 on Sep 16, 2017
BDSM

Author's note: Fiction. Gregg finds his life upended after a difficult breakup, and finds it leading him to an entirely new kind of household. I wonder what would have happened if I had never confessed. At the time life seemed good. I had settled down with Alison and even proposed marriage. When I proposed we had agreed to wait before we set a date. This...

The Perfect Pair Pt. 12

by ChangeYourPassword on Oct 6, 2020
Fetish

The Perfect Pair, Part 12 (fetish, chastity, consensual, cross dressing) By ChangeYourPassword Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not for everyone, but those of us who delve into them understand the allure. The characters in the story certainly do. If you enjoy this story an...

Mistress Taslima of Angola

by Samuelx on Jul 4, 2018
BDSM

"You came to the right place, Ismail," Mistress Taslima Ali said, and the towering, dark-skinned, bodacious Black Canadian Muslim dominatrix looked at the chubby, small-dicked Black man who knelt at her feet. For ages now, Ismail had been scouring the web, looking for the elusive Black dominatrix who was interested in submissive Black males. Sadly, those str...

March Madness Ch. 02

by jbirdman on Sep 16, 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...

Black On Black Cuckolding : Hell

by Samuelx on Apr 3, 2019
Group Sex

Officially, we don't exist. That's what conventional wisdom tells us. If you were to type the words "Black Cuckolds" on Google, all you'd get are references to the standard-issue Cuckolding, which typically involves a big Black guy fucking a White woman while her husband or boyfriend, also White, watches. Nothing wrong with that if that's what moves you. My...

Frustration Pt. 05

by kalkstein1970 on Sep 19, 2017
BDSM

I woke up slumped on the floor, naked, my cock flaccid, the memory of that incredible orgasm still fresh in my mind. You were still there, lounging on a comfortable chair, legs crossed, one stiletto heel dangling, watching me with a mix of amusement and affection. "Good morning, sleeping beauty," you said. I shook my head to clear it, and stood up slowly....

Chastity Debauched: Penitent

by MorganHawke on Sep 15, 2017
BDSM

In Which Chastity has an appointment with the Unholy Father... For Bear Part One: The Club “I can’t believe my Dad had me to come to his company pool party at the Club.” Chastity grumbled to herself while standing before the tall mirror completely nude. She stared into the mirror’s reflection of her deep violet eyes as she tied her waist-length, strawberr...