Chastity Sissy Cuckold Stories

18,147 results
Orientation
Length
Source
Infinite Scroll

Girlfriend Trouble

by lovelymess212 on May 29, 2019
Fantasy

You've been dating Sam for a long time, even thinking of popping the question sometime soon. She's perfect in every way, and its near your second anniversary. You have your own apartment together, living with each other to count on. Maybe life is far from perfect, but you have each other. Of course, sometimes life throws you a curve ball. You wake up one mor...

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A Cuckold's Story

by yumacd on Sep 25, 2017
Fetish

Part 1 I sometimes have submissive tendencies when it comes to sex. These are never full-time thoughts, just fantasy interests I like to explore occasionally. A while back I started gravitating to this one particular dominant woman on the interent. Her name is Lexi Lapetina. She has a cool website, but that's not where I found her. I first discovered her...

Cuckolded by Kate Ch. 05

by cuckytoher on Jul 3, 2018
Loving Wives

The early morning sun streamed through the balcony doors onto Michael's muscular thighs and legs. His head buried beneath a pillow, he slept soundly. Kate stood naked on the balcony, the ocean breeze caressing her naked body like a million tiny feathers tickling her. Glancing down to sand below her she spotted a cat playing with mouse, toying with it, decidi...

A Very Public Sissy Adventure

by DivinaTellsAll on Jun 4, 2019
BDSM

At Madame Vega's instruction I had spent the last hour edging myself. This is not always an easy task for a sissy who is not allowed to stroke her clitty. The edging was primarily accomplished by the use of a vibrating wand inserted in my fuck hole, and an Hitachi wand that I could rub my clitty on, as I teased my fuck hole deep inside. I had been banned fro...

Black Cuckolding In Montreal

by Samuelx on Sep 11, 2017
Interracial Love

Never say never, I guess that's what the moral of the story is. When my husband Benjamin "Benny" LaCroix told me that he wanted me to cuckold him, I think my jaw hit the floor. Benny is six-foot-one, lean and muscular, with dark brown skin, curly Black hair and lime-green eyes. My darling husband is biracial, born in the City of Montreal to a French Canadian...

Mistress Training Guide

by Kerrysslave on Jan 1, 2019
How To

Slave Training basics Let me start by saying that I love my husband. Some people have a desire to submit, some have a desire to dominate. This is the way I trained Allen. People very quiet a bit. I will explain why I have these basic rules and steps. The most important thing is to be consistent. 1. Never let him know what your ultimate goal is. Never e...

How I Became a Chastized Cuckold Ch. 09

by gizzard on Jun 18, 2018
Fetish

**Warning** This fantasy story series contains or will contain elements of Male Chastity, Orgasm Denial, Female Domination, Cuckolding, Interracial Sex, Bi-sexual Innuendo and Tendencies, Teasing, and BDSM Activities. If any of these topics are offensive you to, I recommend not reading. * The next week and a half seemed to skirt by as if Father Time himsel...

OMG Mom!

by TheSecretlyUnlikelyDuck on Feb 5, 2019
Interracial

You pull into the driveway of 15 Preston Road at around 3pm on a friday afternoon. The light of the late spring sun pours over you as you come to a halt, parked behind the red BMW belonging to Mary Lange. She is a gorgeous blonde, who looks far younger than her actual age of 39, and is unarguably the head of the Lange household. You don't see her husband's c...

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Wife Left Me so I Could be a Girl

by TammyPanty on Jul 10, 2018
Transsexuals & Crossdressers

I Am The Girl My Wife Did Not Want As the only child of a single mother I grew up around all things feminine. Having lingerie and stockings drying in the bathroom was normal for me and I always loved how pretty the full cut nylon panties and slips with tons of lace looked. I lived at home with my mother until she unexpectedly passed away when I was 23 year...

Becoming a Sissy Cuckold Ch. 01

by Pantieslave on Mar 27, 2019
Fetish

Beth and Dan were married very young, just 20 years old each. As such both were virgins when they married. Beth wasn't an outstanding beauty but very attractive with a nice body and very nice breasts, 36D. Dan, on the other hand, was rather feminine looking and wore his hair long, in a ponytail. Being slightly built, on more than one occasion he was mistaken...