Chastity Trans Stories

8,649 results
Orientation
Length
Source
Infinite Scroll

Just Look at Me Now Ch. 05

by GFfan on Sep 14, 2020
Transgender & Crossdressers

ACT ONE: PARTY PREP "If the item is defective, you can return it for a full refund, but no, you cannot return it if it's simply too big. I'm sure you can understand why." This was the saleswoman's reply to the question I had been instructed to ask about an item Jude and Becky had assigned me to buy. "I doubt that will be a problem though," the clerk, Felic...

The Perfect Pair Pt. 12

by ChangeYourPassword on Oct 6, 2020
Fetish

The Perfect Pair, Part 12 (fetish, chastity, consensual, cross dressing) By ChangeYourPassword Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not for everyone, but those of us who delve into them understand the allure. The characters in the story certainly do. If you enjoy this story an...

My Secret Revealed Ch. 05

by jealouscuck on May 30, 2018
Transsexuals & Crossdressers

The trip to New York was indeed the watershed moment in our relationship. Karen was showing me off as her submissive husband. I could have been resentful of the way she had me come out, but I was enjoying the excitement too much to complain. She had made such a show of chastising me when she found out about my fetish because we were not to have secrets from...

The Perfect Pair Pt. 02

by ChangeYourPassword on Jun 9, 2020
Fetish

The Perfect Pair Part 2 (fetish, chastity, consensual & non-consensual, cross dressing) By ChangeYourPassword Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not for everyone, but those of us who delve into them understand the allure. The characters in the story certainly do. If you...

Writing Healthy Relationships

by yumeko on Sep 16, 2017
Reviews & Essays

I love written pornography. From the time I first discovered the written pornography in magazines when I was young, the written word has always been my favourite way to get off. And perhaps that should have been a clue to me, because I found out later that supposedly boys and men prefer visual material, but at the time I didn't much care. I only cared that r...

Broken on My Break Ch. 02

by TopSeeker on Nov 13, 2017
Transsexuals & Crossdressers

**Disclaimer, all people places and events in this story are completely fictional and made up by me. This story contains the following elements: non-consent, dominant shemales, spiked drinks, shemales/transgenders being the penetrative partner to males, many terms used which are derogatory both in general and specifically to trans-gendered individuals. Pleas...

Lost in a Female's Pleasure Pt. 07

by LucysFox on May 27, 2019
Transgender & Crossdressers

Synopsis: Damien was looking forward to a relaxing weekend free from his abusive father, but things quickly took a downward turn when he got kidnapped. Turns out it was maybe for the best though, or at least not as bad as staying with his dad would be. In this chapter Dee becomes feisty as the hormones kick in, and she's introduced to chastity and butt pl...

How to Write Realistic Transsexual Characters

by TGirlNerd on Sep 1, 2017
How To

Table of Contents [1] Introduction: [2] Who are transsexuals? [3] Who are cross-dressers and transvestites? [4] What are cross-dressers and transvestites like? [5] How can I relate to my transsexual characters and get into their heads? [6] What terminology should I use? [7] What terminology should I avoid? [8.1] What do trans women look like naked?...

A Day in the Lifestyle: Cock Cage

by secondsamuel on Dec 3, 2019
Fetish

Author's Note: My wife and I have been together for nearly ten years. In that time, we have been heavily involved in the local BDSM/Kink/Swinging scene, usually labeled ubiquitously as the lifestyle. I am incredibly fortunate to have such an open-minded and sexually adventurous partner. With her permission, this series shares and amalgamates some of our mo...

Lost in a Female's Pleasure Pt. 08

by LucysFox on Jul 3, 2019
Transgender & Crossdressers

Synopsis: Damien was looking forward to a relaxing weekend free from his abusive father but things quickly took a downward turn when he got kidnapped. It appeared that maybe it was for the best, or at least not as bad as staying with his dad would be. Things start to become more complicated though as Damien reaches the brothel... Authors Note: I just want...