Permanent Chastity Sissy Stories

27,304 results
Orientation
Length
Source
Infinite Scroll

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

Sissy Maid to Be... Ch. 03

by missjennymaid on Apr 8, 2019
Transgender & Crossdressers

I would recommend reading the first chapters to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jere...

Shopping and Sucking

by Subkoksukr4u on Mar 2, 2020
Fetish

Matt was in the kitchen as usual preparing breakfast. He'd been instructed to prepare all the meals according to a specific menu plan each day. He finished the sauce for the eggs Benedict got on his knees and waited. He was wearing frilly pink crotchless panties and a matching bra, his bright pink CB 6000xs chastity device was barely peeking out between...

Lock Your Phone

by Iamasissy on Sep 15, 2017
Transsexuals & Crossdressers

I am a sissy and I love it like most sissies I dream about belonging to a man to be owned by him. I fantasize about being outed and being forced to become a transsexual. I put out adds on craigslist NY looking for a Master. I take lots of pictures dressed, I take videos dressed saying my name is Karen I am a sissy and I want to become a transsexual for a rea...

Black Lady Cuckolding Black Men

by Samuelx on Sep 17, 2017
BDSM

What's up dear family? My name is Yasmina Hussein and I'm a Somali Canadian woman living in the City of Ottawa, Ontario. A while ago I discovered the world of BDSM, shortly after my divorce, and have been really into it ever since. I discovered that I have a talent for and a desire to dominate people, especially men of color. As a Somali Canadian woman, I wa...

Ultimate Sissy Weekend Ch. 01

by SissyTwinkleToes on Dec 24, 2019
Transgender & Crossdressers

Dressed head to twinkle toes in beautiful baby pink, Sissy Susie nervously waits for her friend to arrive and the most humiliating weekend of her life to begin. She winces as her teeny clitty squirms in its pink prison, a chastity cage that's been on for four frustrating weeks. Her cage is safely tucked away in her pink ruffly panties, covered in sweet littl...

The Dominatrix Order Pt. 02 Ch. 01 - Sissies

by Jwwsmith on Jan 22, 2019
Transgender & Crossdressers

THE DOMINATRIX ORDER: FEMDOM EROTICA 2 BOUND BY LAWS BY J.W. SMITH *** "All Women Are Created Equal" was inscribed on the bronze plated plaque on display in Representative Johanna Aletheia's office. It was the declaration put forth by The Founding Mothers of Femininus, of which Johanna's ancestor belonged to. Johanna was of the oldest lineage of Feminin...

The Set Up Pt. 02

by undermythumb10 on Sep 15, 2017
Fetish

This is the continued story of my life as a sissy and is a continuation from part 1 The Set Up. ***** As I mentioned I am sat tied to a chair with my stepdaughters panties placed so the crutch is over my nose, it's a long story which started when I met and married my wife now Mistress some six months ago. I am now a total submissive sissy cum slut for my...

Turned into a Slut Ch. 02

by xaitonnar22 on Sep 19, 2017
BDSM

I woke in the morning to Jennifer sucking my cock. She had pulled the sheets off the bed and was kneeling between my legs, licking up and down the shaft. Every few passes she would let it slide into her mouth and wash the head with her tongue. Her other hand was busy teasing at my anus, sliding a little in to massage my prostate. I sighed in pleasure and Jen...

Mistress Chronicles Ch. 05

by MistressMtoyou on Sep 25, 2017
Fetish

Background: This story involves my on-line subject Nancy, who I introduced in Mistress Chronicles 4. We've had no in-person relationship. In fact, in all of our sessions Nancy has never actually seen me. I have sent him pictures that I have told him look similar to me, but never an actual photo. * By way of background, Nancy is a computer nerd. Brilliant...