Chastity Cross Dressing Stories

77,281 results
Orientation
Length
Source
Infinite Scroll

Halloween Pool Party Pt. 04

by sissymissyct on Sep 14, 2017
Fetish

Monday morning I was awakened early by Miss Annie releasing the air from my plug and swiftly pulling it from my bottom. I cried out from being so crudely awakened from my slumber and that got me a quick but hard smack on my already bruised bottom. "Good morning Brenda, time to shower and get ready for a big day", she informed me. "Thank you Mistress" I answ...

Fourth Slave

by RubberBudcus on Sep 16, 2017
Transsexuals & Crossdressers

I had been to this particular establishment before. I knew very well what they did and the women here were nearly all abducted. I knew that. What had brought me here today or rather on this night, was the loss of my slave. I had sold her when I got bored with her. I had a particular taste in women that required them to be both submissive and very slight in b...

The Game

by teasemedenyme on Sep 13, 2017
BDSM

Stretching as she slowly gained consciousness and feeling an unaccustomed ache and freedom, Melanie slowly opened her eyes. Running her hands down her body she discovered what the sense of freedom was... her chastity belt was missing. And the ache? She remembered a wild night of sex... being used by her Master for His pleasure... but receiving so much pleasu...

Prize or Penalty - Back for More

by AlinaX on Jul 9, 2019
Exhibitionist & Voyeur

"Are you ready?" the voice in my ear asks, even as I ask Ellie the same. She nods, her expression etched with fear and uncertainty. "It's not too late to back out," I reassure her. "Oh God, please don't," the voice says. Sarah is the show's director, and co-conspirator in tonight's mischief. I can't help feeling a little guilty that I'm putting Ellie thro...

A Different Kind of Home Ch. 03

by starmanz1 on Sep 16, 2017
BDSM

The following night, Thursday, I was not on service duty and so ate with everyone, but even though the conversation was pleasant, I did not seem to be learning anything new about what was going on in the house. After dessert I went to my room. A couple of hours later, Miss Becky walked in. After I kissed her feet, she had me stand up. With a look of disgust...

First Time

by eroticbisexual on Sep 15, 2017
First Time

My wife and I have been married for a long time. We are deeply in love, and have a great sex life. I have always been kinkier than her, but over the years she has explored with me and over time become a sexy minx who secretly loves our kinky play. She is very beautiful, slim, erotic and with a body that make me proud to be her husband. I have always had bi...

Where did My Damn Key Go Pt. 01

by PascalSage on Apr 17, 2018
BDSM

I had to admit it. I had a slight problem...okay I had a pretty big problem. But now I'm going to address it once and for all. And the solution was right in the UPS man's hands as he approached my front door. I stared at him silently, keeping myself fixed on the small brown package that he held, watching him from the window of my apartment. My mind was swimm...

The Journalists

by Wifetheif on Sep 13, 2017
BDSM

I started in the participation journalism business because of my wife. Of course we started back before we were married. We met in college and quickly realized that we were soul mates. The fact that she was so easy on the eye certainly helped My wife is beautiful, long auburn hair, porcelain complexion. Fabulous legs and great tits. I won't lie, her looks op...

A Freshman's Summer Class Ch. 03

by CapnSteelBoy on May 11, 2020
Transgender & Crossdressers

Edited by HotandHollow **All characters are of legal age for adult content.** We Continue from where we left off with our brave hero, as his adventure continues during his summer of higher education learning! This is a continuing series I'll be releasing as my helpful editor(s) help me clean up my mess.. Much thanks goes out to them, as the editor(s) tha...

Roles Reversed Ch. 02

by lyzunchik on Sep 14, 2017
BDSM

TWO Several days later Bridget returned home from shopping, after I had returned home from work. She had stopped by her office before going on what was obviously a shopping spree. She had a multitude of bags and sent me to fetch them for her out of the car. I had already prepared dinner, as she had instructed per her note left on the kitchen counter. Brid...