Mature Crossdressing Stories

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Infinite Scroll

A Crack in Reality

by Mr Nice Guy on Aug 20, 2018
Miscellaneous

Something is wrong. There is a crack in reality! Things are changing! Is it human made? Has it always been there? Is someone controlling it? Is there any way to stop it?!What's next? Average Office Worker Alex William Borgman, Mad Scientist Rachel Davis, College Lesbian Goth Girl Daniel, average thief Jason Willows, struggling middle class family member. M...

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Tales of Feminization

by AnonWriter on Jun 11, 2014
Fetish

In a seemingly normal town, a new social movement is taking place. White boys are encouraged to act, dress, and be feminine. You are a student at this school, and this is story of how you become a dirty sissy slut. Choose a boy to play as and be feminized. (All characters in this story are of legal age) (I'm only working on Mark's story right now, but feel f...

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Internship

by nimt on Jul 12, 2018
Transsexual

An internship was compulsory as you approach the final year of your high school. The school believes in providing students with the opportunity to gain valuable practical experience by learning from the industry of tomorrow directly. You went for several interviews and only successful candidates get notified. In the events that the none of the companies pick...

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Second life of Emily

by Alexia Wright on Jun 3, 2015
Fetish

I have always wanted to get fucked by another man. Being 5'6" and weighing little over 60 kilos, my effeminite and near hairless body bore no signs of an able bodied alpha male, so i decided to explore my inner girl since my mother and sister are the only people i live with. It started with simple things, like my sister's school clothes, then her under...

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Dutiful Assistant

by Jagvillhem on Sep 28, 2019
Transsexual

((There might be some changes throughout the chapters. This is because I am finding out the way I like to write. I'm learning different styles and quirks. Because of this, chapters might differ in style from time to time. This is definitely a trail and error kind of thing, chapters might have changed once you re-read them, this is because I might have gone b...

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Life's What You Make It

by HYjaCK on Jun 7, 2020
Amateur

The first thing I see as I wake up is the blinding light coming through my curtains. Sadly, I couldn't afford blackout curtains due to my poorly-paying job that barely covered the bills, but I've slowly gotten used to it. I sit up and get off the sofa, stretching my back and neck. I also couldn't afford a large flat, so I had to make do with a single-room wi...

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With Her Blessing

by komrad1156 on Sep 12, 2017
Transsexuals & Crossdressers

"Hello again, Kyleigh!" he said as he looked at himself in the mirror after carefully pulling on his very expensive human-hair wig. Ky Finley was now Kyleigh Finlay and she felt this wonderful rush of endorphins flood over her as she looked at the beautiful creature she'd become over the last ninety minutes. Ky had sandy blond hair so Kyleigh could easily b...

Sex therapist

by qaz on Sep 1, 2016
Miscellaneous

Who do we follow?What's next? A boy A girl What's next? A boy A girl...

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My Babysitter Ch. 02

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

There it was again. That hard, warm cock in my mouth. I loved it. I needed it. I knew it wouldn't last, though. I awoke from my dream with my hands on my dick as usual, but my mom was standing by my bed. I was so surprised to see her standing over the bed I almost forgot to conceal my erection. "Hey son we're home from our trip to Hawaii!" she beamed. "Oh...

Men and Women Cannot Be Friends

by chloevargas on Jul 15, 2020
Transgender & Crossdressers

"If this is what you want," she said, her tone even and controlled. I could tell she was disappointed. Perhaps she'd dreamed of a relationship or she'd fantasized of an emotional connection with me. She'd never hinted or remotely seemed interested. I thought she was happy with being friends. My few fumbling attempts to offer something more were rebuffed po...