Bondage Sissy Stories

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Sissy's Decline into a Slut Pt. 04

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Six: Chantel's Decline is Achieved, Owned by a Black Master as his Sissy Maid and Slut. I cannot believe at what is happening to me here. Master named Gage is about to purchase me and place me into slavery as his sissy maid and sissy slut. I am near in panic, I want to run away, get into my car and drive for the safety of my home. But I know this wi...

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...

My Sissy Cuckold Life

by SissyCuckMike on Jan 2, 2021
Fetish

Hello everyone, my name is Mike and i am now a sissy cuckold. If you don't know what a sissy or a cuckold is i will explain, a sissy is like a cross-dresser but usually dresses up in pink frilly women's clothing and cuckolding is similar to a hotwifing where she goes out on dates and fucks other men without her husband/boyfriend around but with cuckolding it...

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The Journey

by born2srvtv on Sep 19, 2017
Transsexuals & Crossdressers

Tom couldn't believe he was wearing a CB-6000 chastity device while driving to Knoxville to actually meet face to face with Jason. He and Jason had been chatting on a kink oriented website for the last few months. Jason had asked him to buy the CB6000 and Tom found himself incredibly eager to comply with Jasons' desire. Jason had asked him to wear it while t...

Recruiting of a Sissy Maid Ch. 02

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Two: Onto Her Training and Breaking Down. The feeling of fear and dread falls over Chantel as she sits on the flimsy bed in what is for now her prison cell. Totally alone and isolated except for the fact that Mitch and Nate Burrows will lord over her as they orientate, train and ultimately break Chantel from a fantasy sissy to what will be a living...

A Sissy Cuckold to another Sissy

by Gemsissy on Sep 26, 2017
Fetish

"Christ, Bob!" snaps Julie. You just sigh as you feel your skinny cock throb and spurt into the condom next to her bottom. "What about me?" "I'm sorry, honey. You're just too sexy! I came so fast!" you say, blushing in embarrassment that you couldn't fuck your own wife for more than 30 seconds. "Are you some fucking teenager dweeb?!" She spits as she glare...

Becoming a Sissy Maid & Slut Vol. 12

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Bonus chapter added to keep this story moving forward. I felt it should be told and enjoyed. ***** Chapter Twenty One: Sluts at a Party. Our Masters always looking at ways to get the word out about us three sissy sluts all to make sure we become looked for and hunted street walking sluts for sex starved and horny males leads them to putting us out in very...

The Slave and the Sissy Ch. 02

by Sputnik57 on Sep 12, 2017
Transsexuals & Crossdressers

Ella took the chain from their collars when they reported to her, together for the first time, in the morning. Pepper's eyes were exceptionally bright this morning, and slave looked full of vigour and ready to carry out any command that befell him without the slightest hesitation. Pepper gripped his hand tightly, lest she should suddenly wake from this beaut...

Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

Family Chastity Story Ch. 03

by antares34 on Jul 30, 2019
BDSM

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** My gimp son and I have settled into a routine. Permanent chastity with monthly releases. These releases occur on the first day of every month. I...