Chastity Cross Dressing Stories

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Orientation
Length
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Slave Immigrant Ch. 23

by OldGuy1026 on Sep 14, 2017
Sci-Fi & Fantasy

After receiving a cloned body I immigrated 127 Light Years from Earth to Free Skyes. Unfortunately I had to work and pay for that cloned body and I had very few skills a high tech society could use. So it was either I become an Unskilled Labourer or a Sex Slave. I guess Human Recourses had me figured out correctly. All those years in BDSM chat-rooms and webs...

Watch the Receptionist

by justincbenedict on Oct 7, 2019
BDSM

When Aram got back from lunch, he saw Holt, his new assistant, sitting in his chair, her long legs crossed, and she did look smashing in her cream muslin dress. Really, it was a bit beyond the office code, as the dress was more of a mini-dress thing, and just ended past Holt's thighs. But Aram enjoyed looking at Holt as did other men (and some women)in the...

The Perfect Pair Pt. 02

by ChangeYourPassword on Jun 9, 2020
Fetish

The Perfect Pair Part 2 (fetish, chastity, consensual & non-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...

Mistress Chronicles Ch. 03

by MistressMtoyou on Sep 25, 2017
Fetish

Title: Decision time Background/update Even if you've been following the last couple of stories about my subject, Muffin, you might want to read this background as there are a few new points of note. Muffin is slightly heavyset, 36 years old, about 5' 7" and 160 pounds. He is quite submissive and seems to be aroused by a number of fetishes, but he professe...

Delving into Femdom Ch. 01

by readytokneel2907 on Jun 1, 2020
BDSM

**Chapter 1. Growing up Oh my where to begin, I imagine it is best to start at the beginning (or as close to it as I can remember). I grew up in a relatively medium sized east coast city living what some may call a normal life with two sisters and both my parents. Growing up I was always into sports and when I entered middle school I had begun to focus on b...

The Keyholder Ch. 05

by AndreaJordan on Sep 26, 2017
BDSM

Locking Ben's cock inside her new Prince Albert chastity cage had been the highlight of Amy's week. When she closed her eyes she could still remember the feeling of control and the surge of sexual power that she'd felt as she'd rolled around on his beautiful white wool rug. Ben's eyes had betrayed his obvious obsession with her body and with her control of h...

Laura's Femdom Empowerment Ch. 04

by Long2bLocked on Jan 15, 2019
BDSM

Chapter 4 Going Pro It was late January and I decided it was time for some new excitement. I had broken up with Jared a few months prior and I wanted a new sub guy to torment. I was thinking about the best place to find a submissive guy and suddenly I remembered Leesa looking for costumes the previous Halloween. She wanted me to go to the party as a domin...

How to Become a Sissy/Cuckold

by Quietoldie on Sep 14, 2017
How To

This is a How To Guide for Sissies and Cuckolds. Please do not read this guide if you have no interest in the cuckold/sissy lifestyle. Like most couples these days both partners will be doing demanding full time jobs. Traditionally husbands have done gardening, cleaning the car, putting out the trash, performing do it yourself jobs around the house, drivi...

Wife And Bull Take Charge

by Cuckyboy3 on Sep 16, 2017
Loving Wives

This is a cuckolding story describing a wife who punishes her cuckold husband. It has elements of humiliation, fetish, chastity belt, BDSM, cross dressing, cuckolding, and tease and denial. It is all in the context of a wife's love for her cuck husband. If this offends you, please skip the story and find something vanilla to read. -------------------------...

Letter from Sherier Place

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: I am a member and Substitute Treasurer of the Keeplock Club, a select group of women who keep their husbands and significant others in chastity belts. Our oldest member is seventy-eight, the youngest, a college junior. It's a constant vigilance, and I thought you might find it interesting, as your column discusses much of this. On Wednesd...