Chastity Sissy Cuckold Stories

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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...

First Time Cuckold Ch. 05

by Angelscuck on Sep 14, 2017
Fetish

Oscar started sucking my well fucked pussy with great zeal, licking up all the cum that Jordi had deposited. Jordi's cock was so big and thick that it had left me quite sore and Oscar's attentions were both soothing and stimulating. After about an hour and four orgasms, I reached the conclusion that I really enjoyed being sucked to being fucked. Oscar looke...

Black Cuckolding Dreams

by Samuelx on Sep 11, 2017
Group Sex

Sometimes what you're looking for is closer than you think. Take my fiancé and I for example. My name is Stacey Walton and I'm a young Black woman living in Milton, Massachusetts. I studied business administration at Bay State College and earned my MBA at the University of Massachusetts at Amherst. Presently I work for a real estate company in Brighton. I me...

The Wedding Ch. 09

by betamale08 on Apr 1, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 9 – Coerced, Consumed and Consummated... After wrestling my Uncle John out of his suit and laying him out on his back, I knew his passed-out routine was all a farce as he looked to me winking with a smile before going back into his pretend-coma... Faking it in front of Patti and no doubt doing so in the want of stay...

A Pro-Wrestling Cuckold Ch. 06

by longhairedcuck on Nov 4, 2019
Fetish

We walked up the driveway, silently, the nervous excitement palpable in the air and in us. I gave Lily a once over, she looked incredible, dressed in a quaint top and shorts. Her long blond hair flowing down her back in loose curls, all the way to her ass. I stared at her bottom longingly. Darren had forbidden me to touch it, deeming it as his 'property'. O...

BWC for Black Male Sissy

by Samuelx on Sep 12, 2018
Transsexuals & Crossdressers

Meet Bass, which is short for Bashir Malong, a six-foot-seven, dark-skinned and ruggedly handsome man originally from the nation of South Sudan. Bashir is definitely more than he seems, and that's just the tip of the iceberg. A lot of people, upon meeting the tall, handsome brother with the deep voice, wonder if he's some sort of professional athlete, and Ba...

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...

Enslaved by Myself Ch. 05

by Lausunaht on Sep 14, 2020
Fetish

I had fully accepted my place as my clone's personal slutty sex slave and did anything he asked. I became his cum bucket and fleshlight and secretly became addicted to being his. I was still attracted to girls more than guys, but I hadn't seen a girl in months, in fact I hadn't seen anyone in person for months, except for my master. I had no choice but to...

My Cuckold Wedding

by CuckinChastity on Sep 16, 2017
Fetish

Note - this is a piece of fiction. The characters are not real. The scenario is purely a fantasy and does not describe any actual relationship. Laurel is not my actual wife. Enjoy! ***** I stood at the altar alone with Rev. Carl, the minister, looking out at the wedding guests. It wasn't a large wedding, still to me it seemed there were a lot of people l...

A Pro-Wrestling Cuckold Ch. 07

by longhairedcuck on Mar 3, 2020
Fetish

It didn't matter to Darren that I hadn't come in 5 weeks. He insisted on keeping me caged for a week longer even though I was supposed to be let out earlier. He broke the news to me one fine Saturday morning after he'd stayed over at our place. I stood there gaping as he calmly told me about my prolonged chastity. "But, but..." "No buts cucky. This is ex...