Diaper Sissy Chastity Stories

13,981 results
Orientation
Length
Source
Infinite Scroll

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...

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...

Uncovering the Sissy Beneath Pt. 06

by jefferyscott745 on Jul 31, 2019
Transgender & Crossdressers

Disclaimer: This story contains extreme fetishes including BDSM and forced seduction. It is also purely fictional. This is part five of my previous work. Be sure to read parts 1-5 if you wish to understand the background of this section. Sherry and I sat on the couch for a while watching fashion shows again. There was no discussion about what had just ha...

Lace and Love Ch. 03

by vaultdweller111 on Sep 19, 2017
Transsexuals & Crossdressers

Jake Orlov grabbed his duffle bag and rifle case out of the cab of his F-250. He had some other gear in the truck, but he decided to get the rest later. He was exhausted from driving back from Kentucky, training the Blackwell county sheriff's department's SWAT team for the past week. Jake was disgusted at how these guys managed to graduate the police academ...

Family Chastity Story Ch. 02

by antares34 on Jul 3, 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+. ***** Having grown bored with how things were progressing with my sissy son, I have recently ventured into a new and fun project –filming and distribu...

Slave Immigrant Ch. 07

by OldGuy1026 on Sep 15, 2017
Sci-Fi & Fantasy

After receiving a cloned body I immigrated 127 Light Years from Earth to Free Skyes. Unfortunately I had to work and pay for that cloned body and I had very few skills a high tech society could use. So it was either become an Unskilled Labourer or a Sex Slave. I guess Human Recourses had me figured out all right. All those years in BDSM chat-rooms and websit...

The Pantysissy Diaries Ch. 02

by JPantyboyVSL on Jun 5, 2018
Transsexuals & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapter 1 before reading chapter 2. *** The Amtrak train Jaymie was onboard with his new Mistress, Sydney had just pulled into NYC. Jaymie had to get...

Becoming Dogshit the Chastity Bitch

by Mastrbull on Jul 27, 2020
BDSM

It had been more than a month since Mistress introduced me to Sir. I didn't understand their relationship, she would spend a night out with him once a week or so and he would come to Mistress's house Saturday evening or Sunday morning most weekends. I honestly didn't know if they were lovers or playmates or something else but as it isn't my business I never...

Halloween Pool Party Pt. 04

by sissymissyct on Sep 14, 2017
Fetish

Monday morning I was awakened early by Miss Annie releasing the air from my plug and swiftly pulling it from my bottom. I cried out from being so crudely awakened from my slumber and that got me a quick but hard smack on my already bruised bottom. "Good morning Brenda, time to shower and get ready for a big day", she informed me. "Thank you Mistress" I answ...

Sissy Lauren Pt. 02

by CdJade on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Two: A New Girl It was the first day of February and almost six months into Freddie's jail sentence. Or at least it would be if Freddie still existed. On his second week inside, Freddie had been transformed into sissy Lauren, the girlfriend of E wing boss, Ronnie. Lauren had now learnt how to apply her make up to the style of most of the instructio...