Crossdressing Wife Stories

121,758 results
Orientation
Length
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Infinite Scroll

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...

The Good Wife

by komrad1156 on Sep 13, 2017
Transsexuals & Crossdressers

Chapter One "Let's go! Dig deep!" Jason told himself as he passed the nine-mile point. Just one more to go—for today. Running was one of his four biggest passions in life. He also loved his job more than most people. At least he thought that was the case based on the way most people talked about "work." For Jason, work was fun. He couldn't wait to get there...

My Story of Degradation

by Philippasubmaid on Aug 28, 2018
Transsexuals & Crossdressers

A Story of Degradation. 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. I was 47, just divorced for the second time and for the first time in years able to be myself and enjoy what I wanted to do in my own time. I should explain...

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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Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

My Neighbor's Submissive Ch. 01

by marissacd on Nov 27, 2018
Transgender & Crossdressers

Chapter 1 - Exposure They moved in next door shortly after we bought our house about five years ago, a nice couple who were a few years older than my wife and me. My name is Michael. I'm twenty-eight years old, white, five-seven, brown hair, blue eyes and a lean build, suitable for cycling, which I do a lot. My wife, is five-four, slim, athletic and blonde....

Jolene's Momma Pt. 01

by ValoryG on Jul 27, 2020
Transgender & Crossdressers

(The names and locations in this story are completely fictional and have no connection with any person living or dead.) My name's Chris. Wife Jolene and I have been married six years now. Live in the small city of Centertown, Ohio. It probably got that name because it's about half way between Columbus and Cincinnati. Being from a midwestern small town, the...

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...

Ghosts From The Machine

by Halode on Apr 17, 2021
Miscellaneous

Emilia leaned on the railing surrounding the Ghost Machine, tucked away in one of her many rooms at the King estate, watching as her staff put the finishing touches on their restoration project. The machine was polished to a mirror finish, the brass and steel gears and cogs stretching upwards to affix to the high-vaulted ceiling. The dome occupied the center...

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The Chronicles of Miss-chief

by vanillathunder on Feb 21, 2020
Transsexual

These are just some prompts to get started, feel free to add threads for new ones! Salon-the-Job Training: When a young man gets a job sweeping up at a salon, his co-workers decide to teach him about the various treatments they do there. Spell-ing Error: Two friends get more than they bargained for when they try to conjure up a woman with a stolen spell book...

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