Crossdressers Chastity Stories

18,166 results
Orientation
Length
Source
Infinite Scroll

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...

My Story of Degradation Ch. 03

by Philippasubmaid on Sep 10, 2018
Transsexuals & Crossdressers

This story involves BDSM and crossdressing, change of lifestyle and full submission both mentally and physically. If this is not for you feel free to read elsewhere, please. ***** "Yes." Was all I replied. I saw her nod to Cindy and felt Cindy behind me and the cold steel of the handcuffs go back on my wrists, Cindy shut them, and I heard the ratchets go...

Samantha Meets a Dom Master

by SamanthaSatine on Sep 16, 2017
Transsexuals & Crossdressers

A true story - I am the main character and all the various activities described were undertaken with my consent...no harm came to me in any way... ***** The date was fixed. The room was booked – neither of the willing parties could accommodate, a not unusual event in the world these two inhabited from time to time. The morning of their meet had now arriv...

Lace and Love Ch. 02

by vaultdweller111 on Sep 19, 2017
Transsexuals & Crossdressers

Dan had a quick shower, brushed his teeth, and after giving himself an enema he started the process of becoming Alice. He stepped into their bedroom and opened the small walk in closet revealing men's clothing for him and Jake, Jake's old uniform from the marines, some various camo and tactical clothing Jake wears for his firearms training business then came...

Slut in the Basement

by KittyAshleyy on Apr 27, 2020
Transgender & Crossdressers

"Come on, Slut!" Daddy barked at me with a yank on the chain leash attached to my leather collar, causing me to stumble forward in my black high heels. I knew where he was leading me, the basement, Daddy had told me I was going to entertain some of his friends down there. I knew what that meant, which caused my boipussy to squeeze on the large silicone buttp...

The Future is Feminization Ch. 01

by EvelynWilde on Jun 1, 2020
Transgender & Crossdressers

History books and classes are such faint memories that they feel like something I came up with in a dream. The world changed so suddenly that we seemed to collectively forget about all the little things we did everyday. All of our routines, our celebrations, our passions were swallowed up in an effort to resist fate. But fate has a habit of getting what it w...

Feminizing First Step Ch. 05

by antares34 on Mar 30, 2020
Transgender & Crossdressers

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+. Chapter 5 Today began like any other. I awoke in my bed with my wireless earbuds still in my ears. The sissy hypnosis audio track was gently playing...

Life and Time of Lady Vargos Ch. 06

by rik581 on Mar 27, 2019
Transgender & Crossdressers

Chapter 6 "Lady of the House" Martin had been home three days from his visit to the spa, and things were now becoming a bit more of daily routine for him as mistress of the household. As usual he had been awakened early by his husband with a long passionate kiss on the lips. Martin grabbed the sheets with both hands and groaned as he awoke in the affectio...

Humiliation Journey Never Ends

by Subkoksukr4u on Jun 25, 2019
Transgender & Crossdressers

Here I am once again looking up into the eyes of my tormentor, my superior in every way, especially his cock, 10 1/2 inches to be exact. I know because when I first met him he made me measure it with a ruler. He made me measure mine too. I was embarrassed, humiliated and shamed for being so small. It hasn't been called a penis or anything remotely masculin...

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...