Chastity Trans Stories

8,649 results
Orientation
Length
Source
Infinite Scroll

Kayla's New Life

by BelleBlack on Aug 24, 2020
Transgender & Crossdressers

Kayla sat on the patio of the coffee shop and fiddled with her latte. The nervous energy flitting around her stomach was matched by the light summer breeze that couldn't seem to make up its mind which way to blow. Although on the outside, she was a perfect picture of demure grace, inside her head her thoughts raced frantically. This is crazy. No it's not,...

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...

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...

Shemale Orgy

by xploring96 on Nov 14, 2017
Transsexuals & Crossdressers

The following story includes transgender characters, Domination/submission and derogatory terms used to humiliate. If this offends you please do not read any further. Feedback on my stories is always appreciated. ***** All Ron could think about while he stared into her sultry eyes with their smoky dark eyeshadow was, how lucky I am that I am a faggot....

Lulu Exposed

by lulu_dools on Apr 25, 2018
Transsexuals & Crossdressers

My name is Louis and i'm 35 years old. I am just a normal guy with an average build and really long brown curly hair. I like a beer on the weekends when i am watching the footy, used to smoke weed but have grown out of that except for the odd occasion. Every once in a while i also like to have a line of speed and this is where my problem started. You see, w...

Ordeal in Elsewhere

by Wifetheif on Sep 16, 2017
Sci-Fi & Fantasy

William and I were on a more or less routine reconnaissance mission when it the incident occurred. If you are at all familiar with trans-dimensional travel most of the excursions are undertaken by people like William and myself, historians AND theoretical physicists. Truth be told I'm better at both of those skills than William but we make a great team, both...

Mutual Experience

by eigengrau on Mar 12, 2019
Transgender & Crossdressers

Hey everyone! This is like my third attempt at writing a story hehe, it's like I start off well then I end up hating it by the end of a few hours of writing. Let's hope this one is good. All characters are 18+. Hope you all enjoy! * "Wait, you're kidding, right?" Shane said, finishing his pizza. "Wait, you actually asked her out?!" he continued. "Yes,...

Caught in a New Life Pt. 02

by Fibaro on Jun 15, 2020
Transgender & Crossdressers

(Hello everyone, here is part 2 of the story requested by one of my readers.) Chapter 3 While Monroe was having breakfast the next morning Lena passed by on her way out wearing a white body con designer dress with a black belt at the waist, black sheer pantyhose, a pair of white patent leather heels, big rounded sunglasses and a wide floppy white hat with...

Jolene's Momma Pt. 01

by ValoryG on Jul 27, 2020
Transgender & Crossdressers

(The names and locations in this story are completely fictional and have no connection with any person living or dead.) My name's Chris. Wife Jolene and I have been married six years now. Live in the small city of Centertown, Ohio. It probably got that name because it's about half way between Columbus and Cincinnati. Being from a midwestern small town, the...

Randi Michelle's Sissy Subjugation

by Randi_Michelle on Sep 16, 2017
Transsexuals & Crossdressers

To me, part of the process in my case of stripping me of my masculinity involves documenting my transformation and the humiliation that it would involve. For me it started through an encounter with a dominant man who enjoys feminizing submissive males and turning them into 24/7 gurls. It just took the right dominant man to make it happen for real. I've spen...