Trans Chastity Stories

8,649 results
Orientation
Length
Source
Infinite Scroll

Induction Day at Spread Legal

by MKarpenter on Feb 10, 2020
BDSM

I got up early on my first day that Monday morning so I could get ready and make it to the office just before 9am. Not wanting to make a bad first impression for The Mistress was a powerful motivator even though there was a part of me that wanted to misbehave, so that she can stretch out my ass with her strap on once again. Since the interview I couldn't sto...

The Roommate Pt. 15 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

Note: For those who may be jumping into the story only in these advanced chapters, know that Lori is Josh. At home and often around town, he's a woman. When Lori is teaching college, and with family and so on, he's Josh. ***** Lori had obtained his chastity device's combination from Miranda before she departed, and the impediment was quickly removed. Now,...

A Freshman's Summer Class Ch. 08

by CapnSteelBoy on Jun 1, 2020
Transgender & Crossdressers

**All characters are of legal age for adult content.** We Continue from where we left off with our brave hero, as his adventure continues during his summer of higher education learning! This is a continuing series I'll be releasing as my busy editor(s) help me clean up my keystrokes of mess.. Much thanks goes out to them, as the editor(s) that helped will b...

Roommate's Surprise

by Eroreader55 on May 21, 2019
Transgender & Crossdressers

My name is Tom and I recently moved to a new city after graduating from college. I'm 24 and I didn't know anyone in my new city so I was looking online for roommates. I tried to find a guy roommate but had no luck finding someone who was clean and fit the bill for what I wanted. I work in the medical field so I am on 12 hour shifts and I needed someone to ac...

Lost Empire Ch. 66

by Pars001 on Mar 11, 2019
Non-Erotic

0001 - Tempro 0003 - Conner- Thomas 0097 - Ace - Zimmel 0098 - Lucy 0101 - Shelby (mother ship) 0125 - Lars 0200 - Ellen 0301 - Rodrick 0403 - Johnathon 0667 - Marco - Brown 0778 - Jan 0798 - Celeste - Shelby (human) 0805 - Toran 0808 - Radella 0908 - Tara - Mara ------------- Ungrown - unnumbered ------------ 2 - onboard She...

From a Husband to a Dutiful Sissy Ch. 15

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Chapter Fifteen: A Big Decision and Telling Mikel. Helen and I are dressed and ready to go to the ladies gym for a morning workout. I love this and dressing in my girlie workout clothes. Today I am going all black, a black leotard, black tights and black ladies shorts. I am going to contrast with my bright pink trainers. My now comfy long, just below my sho...

A Late-Night Visit

by Alex_Lockheed on Jun 15, 2020
Transgender & Crossdressers

Hi all, just a quick one this time, nothing complex. As usual, it's a trans story involving a girl with a dick. The guy is the top, the t-girl is the bottom. Hope you enjoy it :) * * * * It was 1 am. There was a knock on the door to my holiday villa. The sound echoed through the little building and onto the small veranda at the back. As I sat reading under...

Lost Empire Ch. 07

by Pars001 on Sep 13, 2017
Non-Erotic

Derrick jerked awake as the proximity alarm began to wail, "Shelby report!" Derrick shouted. "I am reading multiple ships heading in this general direction," she reported. "Configuration," I shouted as I ran to the bridge. "I am reading at least four; first class Ranger ships, closing on our location." Shelby replied. Damn it! First class? Plus there...

Becoming a Sissy Maid & Slut Vol. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Title: How I became a Sissy Maid and Slut for a Dominant Master. Preface: I would like to begin by thanking all who will read my story here. This is a sissy story based on many thoughts I have imagined, many times throughout my life. These erotic thoughts have been enjoyed for a long while in my life. Like many sissy girls, stories like the one I will wri...

ABCD

by NormaJane on Sep 16, 2017
Transsexuals & Crossdressers

Obviously trans-women vary, like cis-woman, in psychology as much as in appearance, and my first four encounters with trans-women illustrate this. I have given them these names, because they are appropriate to their behaviour. I met them some years ago, through a free online dating site, which covered the English region I was living in. You posted a note abo...