Shemale Chastity Stories

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Infinite Scroll

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...

Willing Submission to a Dickgirl Ch. 01

by ArthurSummer2 on Dec 7, 2017
Fetish

Note to the reader: This story takes place in a futuristic world where body modifications and high technology are common place. Because of this, there are a subset of women who choose to have male genitalia attached to their bodies. These cocks and balls can be, and often are, much larger than natural male genitalia. So if you are not interested in futanari/...

Willing Submission to a Dickgirl Ch. 02

by ArthurSummer2 on Apr 4, 2018
Fetish

Note to the reader: This story takes place in a futuristic world where body modifications and high technology are common place. Because of this, there are a subset of women who choose to have male genitalia attached to their bodies. These cocks and balls can be, and often are, much larger than natural male genitalia. So if you are not interested in futanari/...

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...

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...

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...

Mistress M Pt. 03

by humblersub on Mar 2, 2020
BDSM

He was once again in her bed between her legs. He had lost track of her orgasms at about twelve. She was way past that now. He had also lost track of time. He never tired of making her cum. And she never tired of him being between her legs. She had given him increasing license to do what he wanted with his tongue and fingers when he was between her legs. He...

Christian College Sex Comedy Ch. 18

by FinalStand on Sep 25, 2017
Erotic Couplings

*If you make one person happy, you save the World. Make a million people happy and you become a politician* (Thanks for Fortima's presence fixing so many of my mistaks (Oddly there is no sex in this chapter; just prepping for the next rollercoaster) (Yes, this tale is supposed to be somewhat humorous and outrageous too. While not always comedic, I'd lik...

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...

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...