Chastity Cross Dressing Stories

77,281 results
Orientation
Length
Source
Infinite Scroll

Derek & Amy: Derek's Turn

by Kalira on Sep 16, 2017
Transsexuals & Crossdressers

As I walked into the hotel room hours in advance, my cock is rock hard with anticipation. The last time me, my lover Amy, and her husband Matt were all together, it was my dear love Amy's turn to be in charge. Amy had Matt and I dress like two Fifties sluts. The kind of girls uptight parents used to believe would cause the downfall of society. It was both...

The Perfect Pair Pt. 07

by ChangeYourPassword on Sep 14, 2020
Fetish

The Perfect Pair, Part 7 (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 and...

My Friday Night: Switch

by honey28 on Sep 5, 2017
Fetish

Driving home on Sunday night, my phone rang when I was stopped at the light waiting to turn onto my street. Seeing Nick's name, I put him on speaker phone. Before I could say anything, he very loudly declared, "I want to lick your pussy." Hearing that deep, sexy voice usually makes me melt, but I had to giggle. Note to self: never answer his call on speakerp...

Punishment from Poisoned Rose Ch. 01

by PeachandCream83 on Sep 17, 2017
BDSM

I feel empowered; I feel control and even a bit god-like. I am the goddess of pain and retribution. This is my alter ego, The Poisoned Rose. I use the St. Andrews cross completely vertical with four legs; better access to all his personal parts. He is completely restrained face down and at my hands. He has been a very naughty little shit. I have to teach...

Helping Jess Pt. 01

by mski on Sep 25, 2017
BDSM

Jess and I were co-workers. I always thought she was pretty hot, and I thought a few times that she made quite a lot of eye contact with me. She had a great body with long blond hair – that she normally kept in a pony tail and no fat that I could see. She had a mischievous smile, as well as a naughty sense of humour. I thought about making a move on her occa...

Work Day, Fun Day

by manatdawnrise on Mar 28, 2018
Transsexuals & Crossdressers

Showering for work, I look down at my chastity bound cock, still struggling to come to terms with the events of the weekend. A sense of relief washes over me. The relief found when a lifelong secret had been broken. I was no longer wracked with guilt of my crossdressing dark side. No, I was now liberated in mind yet bound in a physical sense. My wife had a p...

The Perfect Pair Pt. 09

by ChangeYourPassword on Oct 6, 2020
Fetish

The Perfect Pair, Chapter 9 (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...

March Madness Ch. 01

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

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 offended, stop reading and do something else. The author retains all rights to this story. You may re-post the story un...

No Going Back Ch. 25

by Devotedadmirer on Sep 16, 2017
Novels and Novellas

Life was just about perfect. At least two or three times a month, Denny and I spent the evening experiencing the wildest sorts of decadence. I was beginning to think that nothing was impossible. The Cult even had a "special interest group" devoted to S&M and domination/submission fetishes. Surprising to me, there was never any trouble finding women (and me...

The Visitor Ch. 06

by Leanne_sissy on Sep 26, 2017
Transsexuals & Crossdressers

The shower when it came on surprised me, he had the shower head in his hand and played the spray up and down over my body, I blinked, recoiling in my shock and looked up at him, the shower gel squirted at me. "I like a clean sissy" I just hated that alien electronic voice so much, but I knelt there in front of him only too glad to be rid of the smell of hi...