Crossdressing Chastity Stories

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Orientation
Length
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Infinite Scroll

My Story of Degradation Ch. 02

by Philippasubmaid on Sep 5, 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. As I sat there sipping my coffee, I thought about our brief email exchanges, I still knew nothing about her, and I realised that I was very nervous, how should I address her, was I goin...

A Perverse Plan

by Candyboi on Sep 25, 2017
Transsexuals & Crossdressers

It started off with little things, small suggestions, that quickly snowballed into perversion. My wife Carla, who for the first decade of our marriage displayed little interest in kinky sex games became a hot wife virtually overnight with total control over me... Carla is 44, has a very curvaceous ass, 34DD tits, and works as a doctor at the local hospital....

Sissy Maid to Be... Ch. 03

by missjennymaid on Apr 8, 2019
Transgender & Crossdressers

I would recommend reading the first chapters to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jere...

Lucy's Revenge Ch. 06

by Cynthia_D on Sep 18, 2017
Transsexuals & Crossdressers

Final Chapter It was Friday night after a very long week of being humiliated. I had a couple of cocktails to calm down after my latest forced outdoor adventure - being exposed to numerous people while crossdressed. The phone had rung and I made the mistake of answering it thinking it was my wife who was due home that weekend. But the caller wasn't my wife i...

Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

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A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...

From Submissive to Slave Pt. 01

by HerBetaBoy on Sep 25, 2017
BDSM

So I sat there, my wrists and ankles bound to the chair I was sitting in. My mouth forced open by the pink ball gag wrapped around my head. My cock, as pitiful as it looked at the moment, was locked in its cage covered by pink lace panties. The view in front of me was both humiliating and exhilarating at the same time. My wife of 4 years was on her back, her...

Mamma Mia - Forced Femme

by ppeaks42 on Sep 16, 2017
Transsexuals & Crossdressers

"We need a little more feminine energy around here." The words hung in the air as Tommy's devoted licking of Mia's ass slowed to a stop. "You mean another woman?" Mia hooked her legs behind Tommy's head and pulled his face back into her ass. "No, I mean you, you dumb sissy bitch." Once Tommy finished with pleasuring Mia, she led him into her closet. She...

Rubber Doll at the Girls Party

by MiOtroYo on Sep 15, 2017
BDSM

Mel always liked the fetish porn – girls in those crazy latex outfits were performing the weirdest things ever... Add to that insane piercings, multi-colored tattoos and such – and you can cum in no time when watching. He was somehow skipping the idea of trying stuff like that himself, but his new girlfriend resulted to be an exact person for some fetish fun...

The Basement Ch. 03

by FiveDots on Jan 20, 2020
Transgender & Crossdressers

Welcome back to The Basement. Warning that this story continues to become darker. The sodomy begins here... --------------------- Once he started fucking me, he didn't stop. I complained, I pleaded, and even begged but, so far, after weeks of blowjobs and cock worship, I had ultimately complied with every demand. So, it was pretty obvious, in retrospect,...