Sissy Shemale Chastity Stories

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Loraine's Self Bondage Re-Creation

by loraineveritas on Mar 12, 2019
BDSM

The following is my re-creation of an event that happened a few years ago. I had been a sissy slave to Mistress Marie for over 2 decades during which I become a totally submissive slave to Her every desire. I think of Her often as She has passed now. While doing Self-Bondage activities shortly following Her passing my wild imagination conjures up the Mistres...

The White Slave

by mspbottom4black on Oct 6, 2020
Interracial Love

Editor's Note: this submission contains raceplay and femdom content. * Not long ago it was a straight and stuffy white male. it was arrogant and self-satisfied with its white male social and economic leverage and advantages. In the rat-race of white society it suppressed its submissive white side. But from time to time it would slip into daydreams of hav...

Whitewash High Ch. 03

by EnglishTeacher on Sep 25, 2017
Interracial Love

The couple turned towards the woman at the classroom door. Fresh cum dripped off of Principal Weiss' face, cumdrunk lust still apparent on her face. "You two are lucky I'm the only one in the building," Michelle said, walking over, shaking her head at the mess. "How long have you two been fucking?" CRASH! Michelle slipped on a puddle of cum, falling on...

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...

Secret Makes Him a Cuckold Bitch

by Subkoksukr4u on Jul 29, 2019
Fetish

Getting caught doing something kinky or sexual for some people is a turn on, for others it's humiliating. There's lots of different variations. Like when you get caught doing something with another person or get caught doing something by yourself. Anyway way you slice it, getting caught can be embarrassing to some degree. This story is about someone finding...

Bayonetta's Abuse Ch. 03

by ChainedToAKeyboard on Sep 13, 2017
BDSM

As anticipated, James will be spending the weekend at Jeanne's manor while Bayonetta is away on business. What pleasures and horrors await within? Bayonetta's Abuse III - Weekend At Jeanne's It was another bright spring day as James and Bayonetta made their way up the long walkway to Jeanne's estate. The compound was well fortified with a chain link fence...

The Secret of the Island Pt. 04

by neoview on Oct 30, 2018
Sci-Fi & Fantasy

You thought the story had died but it was just my lazy ass refusing to continue. Also I was busy with my girlfriend so I couldn't really focus. Yes, I have a girlfriend now. Well "she" prefers to be called a girl even if she isn't. Without her I would finish this story much faster, but... she gave me some interesting ideas which were too good to ignore. ***...

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...

Imprisoned in Chastity

by Longjohnsilver30 on Aug 31, 2017
Fetish

Lynchburg prison was a low security prison for non-dangerous criminals. Mostly white collar criminals with money ended up in this place. It was actually not too shabby a facility. It had single rooms with en suite bathrooms equipped with private showers, drawers for your limited clothing choices and a TV in each room. I was even able to take my Xbox into the...

The Ranch

by lonerancher on Sep 17, 2017
Fetish

My wife Brenda came home and confessed to having an affair at work with Robert a black man. She said he made her cum so hard and apologized to me. Then she said Jess if I slip again will you leave me I said I would cross that bridge if it came. We had been married for two years, both with good jobs and great house bought life looking good then this affair. I...