Crossdressing Wedding Stories

34,998 results
Orientation
Length
Source
Infinite Scroll

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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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...

A Transvestite Odyssey

by lynntg0444 on Mar 18, 2020
Transgender & Crossdressers

I like playing a girl, but it's complicated. I have always been more attracted to women than men, and had many relationships with women including two marriages. As a young man I had several sexual experiences where I played a feminine role. Wearing girly things was a real turn-on for me, and it seemed to make it less queer for us both. I would later learn th...

Sissy Escape

by Haley_Hazel on Sep 26, 2017
Fetish

You are John Doe An average man, not too young, not too old. You have zero money, no car, no girlfriend... Basically a real loser. You live in a dive apartment downtown. It's not a great place to live, but it's home. Everything you need is right nearby. Groceries, Bar, Restaurants, it's near a park, and there's even a porno shop down the road. Because it's d...

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Real Life: The RPG

by Katnaace on Nov 25, 2019
Fetish

Having logged in, you get to the biggest question of all - who are you going to play? It's not like this is a big deal. You can just create your character and be on your way.What's next? Danny Hopkins - Dude with a sister Lydia Onava - Widow waking up in an unknown place Claude Rogers - On his way to visit his Aunt Henry Wells - Protesting H20 What's next...

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Submission

by Domestic on Sep 24, 2019
BDSM

Your name is John Doe. Where this story takes you is up for your decision. You can choose your gender, you can choose your significant other. But after that, you will lose the ability to choose. You will become obedient, like you know deep down you should be. Ready? Pick one, and begin. NOTE: {[email protected]}It is highly recommended that you play thi...

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