Gay Chastity Stories

28,507 results
Orientation
Length
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Infinite Scroll

Mistress Monique Pt. 02

by bleedndkn on Sep 25, 2017
Fetish

This wasn't even my fantasy, I thought as I purchased the clamps, butt plug, heels and maid dress online with expedited shipping. The next day I brought the items in a backpack to Mistress Monique's apartment while she was at work. I put everything on then placed the butt plug in my ass and tightened the nipple clamps painfully so they wouldn't fall off, th...

JoeBob, Submissive

by justincbenedict on Sep 17, 2017
BDSM

JoeBob waited with great nervousness at the table at Solozzo's Pizzeria. He wondered whether his date would show up. Would she be a beast? A lot of the women who were involved in the BDSM scene were just uggoes or fatties who were desperate for a man, why not a kinky one? That had been the problem with Elaine. She actually had had a pretty face, and nice bi...

Beta Male Slave Academy Ch. 02

by Tazokm on Jul 13, 2020
BDSM

After being blown and locked, Miss Carly explained to me that the compound we were at had over a hundred rooms and approximately 50 current residents. She began walking me to a room where I was to keep myself preoccupied until they had prepared my sleeping arrangement. I walked butt naked behind Miss Carly down a high-ceilinged hallway. Her ass was absolutel...

A Changed Man Ch. 1

by sub5000 on Sep 12, 2017
Fetish

Part One - Beginnings It had to happen one day I guess. I had such a collection of porn on my hard drive, that it was inevitable that one day my wife would stumble across it. It wouldn't have been so bad if it was average, everyday porn, but my collection consisted of more 'specialist' images. There were pictures of shemales with big hard cocks dressed in s...

The Wedding Ch. 01

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Intro) This is the continuation in the life of Dale Horn and the never ending saga of both his pleasure-- and his plight while living in this new world of sexuality and discovery brought about through the hands of his caring, supportive Mother and as well, his long lost love Patti... Where we left off -and with every ones encouragement our Dale saw himself...

Caitlin and Mistress Vicky Ch. 03

by Jemina004 on Sep 19, 2017
Transsexuals & Crossdressers

I was sitting nervously in front of the mirror in the newly decorated guest room. Chad was set to arrive in half an hour. My wife was getting ready in what was for now our bedroom. She had told me to dress up for the occasion, though I was still to wear my maid's outfit. I opened my jewelry box and tried to decide how to accessorize. I selected a lace choke...

The Perfect Pair Pt. 05

by ChangeYourPassword on Jul 13, 2020
Fetish

The Perfect Pair, Part 5 (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...

Sub Rosa Ch. 02

by Margotcul on Oct 6, 2020
Transgender & Crossdressers

3. Needless to say my night was -- again -- troubled. I removed and cleaned the vibrator before I went to bed, but the cage remained in its place. I woke up numerous times during the night to painful erection attempts. After my second night with little sleep, I was in ruins. I got out of the bed and left my bedroom. There was no sign of Mael yet. I did my...

Black Babies Matter

by JoyGrrlSyn on Sep 13, 2017
Fetish

(Magdelyn K. Bordeaux) 01/03/2017 "Welcome. Welcome. If everyone will just settle down and find a seat. Find a seat. Thank you. For those who don't know me, I am Anita Seamen, President of SFLRC. I'd like to thank everyone who make it out tonight. It's a very large turn out. The Society for Female Led Relationships and Cuckoldry is celebrating five years a...

Trudging The CessPonds

by MrFinesse on Apr 7, 2018
Fantasy

You are a penniless citizen in the kingdom of Gradrod. You are currently living in a large poor house with over twenty other people, taking odd jobs from the farms and plantations outside the kingdom's walls and barely making any money. You have always wanted to be an adventurer, but never knew where to look for treasure and even if you found a spot, it's us...

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