Crossdressing Sissy Stories

7,212 results
Orientation
Length
Source
Infinite Scroll

BLACKEDmailed Into Being a Sissy

by AnonWriter on Jun 17, 2019
Fetish

Author's note: I've hit serious writer's block with Tales of Feminization, so I decided to try something a little slower and more limited in scope. I'll be focusing on one primary storyline at first, slowly branching out with other choices. You'll notice some chapters will have multiple choices, but this is just to act as a reminder for me for future content...

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Asian Bimbo Sissy Slut Ch. 01

by melltsslut on Sep 14, 2017
Transsexuals & Crossdressers

Soo...where should I start? I'm sitting here now in liquid black leggings, a hot pink crop top, and a carefully teased wig, with D-cup breast forms glued onto my chest. Oh, as well as the special panties my girlfriend designed - for both of us! From the outside, they look like French briefs. On the inside, they're a little more special, if you get my drift....

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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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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A solution

by Seahawker on Apr 3, 2020
BDSM

Hello my name is Mark. I'm a 35 year old marketing accountant with my father's advertising agency. My wonderful wife, Stacy also works as an accountant at my fathers company. We have been happily married for 12 years. With our hectic schedules, children have just not been a real possibility and to be honest, neither one of us are in a hurry to become parents...

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The Transition Ch. 01

by Quantarx on Jun 8, 2020
Transgender & Crossdressers

Greetings and thank you so much for choosing to read my story. This is intended to be a multi part series so bare with me as I try to develop the characters and lay down the backstories. As always, Your feedback is always essential in the development of the story going forward. Please leave a comment down below * I Had been Married for about eight years w...

The Photographers Assistant Pt. 02

by panty_wearing_sissy on Nov 13, 2017
Transsexuals & Crossdressers

If you are under 18, please stop reading and delete this document immediately. This story is pure fantasy. It does not relate to any real events, either past, present or future, and is only suitable for persons over the age of 18 mature enough to understand, and distinguish the difference between fantasy fiction and real-life. ***** Jake didn't remember e...

My Husband a Pornstar Ch. 04

by gtanya on Mar 21, 2018
Transsexuals & Crossdressers

Chapter 4: Conclusion Here is a small brief of what has happened till now: My fairy husband had been seduced by a strong man at home and then had agreed to be a sissy pornstar. Fairy new master had trained him as a sissy to perform in a gay movie without his knowledge that he was making a sissy trainer porn movie the whole time. I found out and threatened...

From a Husband to a Dutiful Sissy Ch. 06

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Six will compress time a bit more forward in moving the story through time. It will be set two months forward from the original start date of the story in Chapter One, when Helen found out her husband Phil enjoyed crossdressing and fantasized about being sissy maid and a sissy slut. It all picks up with bit of recollecting from Phil who is now Chante...

Dreams

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

"Hey! Hey! Wake up, wake up!" "What? Jo, what is it? What's going on?" "I think you should be telling me that!" "I don't understand." I was slowly coming round now, But I was still mystified as to why my wife had woken me at 2 a.m on a Saturday morning. "Erm your cock is as hard as nails and you were waving your ass in the air," Jo said, starting to laug...