Sissy Feminization Stories

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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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The Sissymaiden's Tale Ch. 01

by ppeaks42 on Mar 7, 2018
Transsexuals & Crossdressers

The world was not always this way. Though few remember it, and even fewer choose to speak of it, there was a time when things were different. Before disease ravaged the land. Before the great feminization. Before the influx. Before the Femocracy. It was whispered that once white men had been just that: men. It was nearly impossible to believe, seeming more t...

Fine Tuning

by cathynylons on Jun 19, 2018
Transsexuals & Crossdressers

As I served my wife Dominique a brandy in the living room, I noticed that she was looking me up and down with her famous wicked smile. After finishing washing the dinner dishes I returned to the living room to see if she desired another glass of brandy. Again, I noticed her looking me over. I worried that perhaps there was a run in my nylons or that my masca...

Feminizing First Step Ch. 06

by antares34 on Jun 1, 2020
Transgender & Crossdressers

(All characters are age 18+) Today my mom was having her friends over for a pool party in our backyard. They had been here all afternoon --mainly lounging around the secluded swimming pool and patio area. Michelle had been first to arrive. She was my mom's old roommate from university and came wearing a black bikini and floral print sarong. Next was Kendra...

'Cumshift' World Rules

by AlexRaymond22 on Apr 1, 2020
Reviews & Essays

So far as I can tell, I invented this world. It draws inspiration from a few other ideas, most of them based around the 'sissy' fetish and subculture, but I've never seen it anywhere else, so please accept my apology if the idea isn't as novel as I mistook it to be. The name is likewise made-up, if anything already has the name, I mean no offense by appropri...

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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Rubymoon Private Asylum Pt. 04

by Tombescent on Sep 14, 2020
BDSM

The patient had been in the custody of Rubymoon for a little over four months. It had been some time since anyone had thought of it as "Dr. Smith". A C note had played hours ago, indicating the patient should be still. It knelt in the center of the room, staring blankly, not daring to so much as scratch an itch lest it provoke the buzzer. The patient was a...

Discovering Mistress Sarah's World

by oneguy4fun on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 1: Meeting Mistress Sarah Joe's heart pounded fiercely as he stood at the door to his Mistress's house. He did not expect to be so nervous at his first meeting with her. After all he had known her for over a year. Mistress Sarah had been gracious enough to allow him into her world. He was fortunate to fall under the control of such a beautiful domin...

My sissy sister

by Alana-S on Jun 9, 2020
Transsexual

Did I really want this? That question had haunted me for weeks now. For years sissy porn had been my main masturbation fodder, and two months ago I had decided it could be more. That I could be more. I always wanted to be pretty like girls were, and had been openly bisexual for years. Why not try this? Why not be a sissy? I signed up to an online feminizatio...

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Sissy Suite

by Titlecardpink on Apr 22, 2025

Here you are. The Sissy Suite. You've been waiting your entire life for this moment, saving every penny, every dime, and every dollar you could come across. You've always felt like a girl, always wanted to dress like one, and you always wanted to be treated like one. Your name doesn't matter, it'll be void once you step through that pink threshold. You're 18...

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