Trans Chastity Stories

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An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...

Slow Descent into Sissy-Hood... Ch. 01

by Slipperylock on Oct 31, 2018
Transgender & Crossdressers

Beta boy beginnings. It started when I was online, lonely and drunk. I'd been at University for maybe three months at that point, struggling along with a Masters degree in Economics. Unlike my undergraduate years, I had decided to live alone in a one bedroom flat - I thought that with more privacy would come more focus. What I hadn't counted on was that wi...

Writing Erotica For The First Time

by LitKate on Sep 16, 2017
Transsexuals & Crossdressers

I always found it somehow difficult to type on a laptop when it was actually on my lap. Even more difficult when crammed into a car that's driving around on bumpy af roads. But I had wanted to try writing erotica. Nothing overly fetishy or magical. Just something that spoke to what it's actually like being like a modern trans girl or whatever. I just wished...

Becoming Daddy's Girl Ch. 02

by Sungmehetu on Aug 20, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** After the groceries were put away, I was allowed to shower. The warm water was instant relief to the stickiness I felt in every pore of my skin. I was still aghast on how I had been altered so permanently in just the last 48 hours. A liter of warm water was now being pushed into m...

Retired to a Whole New Life Ch. 02

by sissymissyct on Feb 11, 2019
BDSM

As my fate was now sealed by the lock, Mistress Michelle handed me the key and instructed me to put it on Cara's ankle bracelet. I gently undid the clasp and attached the key as instructed. I re-fit the bracelet and lovingly kissed her foot, and then Mistress Michelle's. They helped me too my feet and we went back out to the living room, Michelle locking th...

Femdom Scenarios

by unknown156 on Apr 29, 2025

Live through your wildest femdom fantasies as these sexy girls dominate and humiliate you to orgasm. Anyone can feel free to add their own storylines but they must abide by the following simple rules: Every character involved with the JOI or any other sexual activity MUST BE 18+. You can have characters who are under 18 but they can not be in any way involv...

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Butch's Bar Slut

by sissymissyct on Jan 7, 2020
BDSM

(A bit darker than most of my tales. It would fit in gay or nonconsent as well. Gay sex, sissy sex, chastity and punishment.) *** I love this bar, Butch thought to himself as he finished another beer. And why shouldn't he. It had everything a Leather Bear could want. Plenty of hot men in leather, and some women as well. A bunch of trans girls and some siss...

Slow Descent into Sissy-Hood... Ch. 02

by Slipperylock on May 11, 2020
Transgender & Crossdressers

I started pretty slow. I'd wear it for at first hours, then a day, and then finally overnight. That one had been the hardest, no pun intended. I would wake up multiple times a night, locked in sweet torture between the inevitably erotic thoughts in my head and the bittersweet tightness between my legs. The first time I'd tried it, I'd made it till 2 a.m. bef...

A Trans Woman's Submission

by ahbedeah on Aug 20, 2018
BDSM

Mistress can't blame you. She knows that you need someone to do your thinking for you. She knows that you need someone to control you. But she wasn't there. Sara was there. You couldn't remember why you were in the bar or what you had ordered. All you knew was that your glass was half-empty when you first noticed her. Her hair was black, streaked with th...

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,...