Latex Sissy Chastity Stories

20,354 results
Orientation
Length
Source
Infinite Scroll

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...

Sissy Life Pt. 02

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

I scurried to the bathroom, tears streaking my face. I was dripping cum on the bedroom floor as I went, but I didn't stop. I just wanted to get out of the room. I couldn't believe how badly things had gone! 20 minutes ago I was stood in my May babydoll, black stockings & red heels set for some intimate time with my wife, my Mistress, but now? Now things were...

Faro's New Brother

by Gman26 on Sep 17, 2017
BDSM

If you're going to be critical just for the sake of being critical, don't say anything because I will flag you with the webmaster. Be constructive with your criticism. I welcome feedback. ***** Shopping day rolled around. For the first time Master was going to take it to town and "teach" it how to shop. It is as if Master forgot it was once free, shopping...

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...

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...