Latex Sissy Chastity Stories

20,354 results
Orientation
Length
Source
Infinite Scroll

Allyson the Sissy Whore Ch. 01

by sissymaidallyson on Sep 12, 2017
Transsexuals & Crossdressers

Kevin was your prototypical mid 20s guy. He had a decent job and lived on his own. He had good friends and whilst he was single he didn't find any problems getting what -- or who -- he wanted in the bedroom. However he had long been fascinated by glory holes and by being serviced in them but by being the one servicing. He was convinced he was straight and l...

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...

Sissy Instructions

by FrostShard on Sep 13, 2017
BDSM

Dear sissy, I trust you are preparing yourself well for our session next week. This session will be your final plunge into the realm of sissyhood. Thus far, you have simply dabbled in it, all the while essentially staying a man. All that will change starting from this session. Starting now, from the moment you finish reading this letter, one thing will cha...

Rubymoon Private Asylum Pt. 04

by Tombescent on Sep 14, 2020
BDSM

The patient had been in the custody of Rubymoon for a little over four months. It had been some time since anyone had thought of it as "Dr. Smith". A C note had played hours ago, indicating the patient should be still. It knelt in the center of the room, staring blankly, not daring to so much as scratch an itch lest it provoke the buzzer. The patient was a...

Sissy Girl Forever Pt. 01

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

The call from Mistress Andrea made my day. I hadn't seen her for over a week and was looking forward to playing with her & having my chastity finally removed. You should know that Mistress and I have known each other for many years and have I always enjoyed being her sissy sub. Lately she has been training me to be more feminine in appearance. I have been r...

X.S.X Experiment

by njcaptionlover on Apr 4, 2018
BDSM

All characters are over the age of 18 years old. ***** Hello. My name is Justine, and I'm a 25 year old single male whose fetish curiosity had finally gotten the best of me. My owner granted me permission to recount my story. I started collecting Playboy magazines at an early age. When I had my first computer at the age of 18, the world of porn opened...

To the Manor Bound Ch. 01

by Nikki258 on Sep 26, 2017
Transsexuals & Crossdressers

[Hey, just to be forewarned, this story focuses heavily on forced feminisation including aspects of BDSM and non-consent, so if that's not your thing this might not be the story for you. I also feel the need to point out that I don't agree with any of Lord Madison's political views: this is porn, not polemic. With that said, I hope you enjoy it!] Chapter 1...

Mistress Chronicles Ch. 03

by MistressMtoyou on Sep 25, 2017
Fetish

Title: Decision time Background/update Even if you've been following the last couple of stories about my subject, Muffin, you might want to read this background as there are a few new points of note. Muffin is slightly heavyset, 36 years old, about 5' 7" and 160 pounds. He is quite submissive and seems to be aroused by a number of fetishes, but he professe...

March Madness Ch. 03

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

Feminizing First Step Ch. 04

by antares34 on Dec 10, 2019
Transgender & Crossdressers

(All characters are age 18+) It has been months since my mom and therapist started my sissy transformation. So many changes have happened! Shortly after placing me in a chastity device, they revealed to me that the "male hormones" I thought I had been taking were in fact just the opposite -progestogen and testosterone blockers to be specific. To be honest...