Sissy Transformation Stories

14,811 results
Orientation
Length
Source
Infinite Scroll

Magic Panties Ch. 06

by nolfon1 on Sep 12, 2017
Transsexuals & Crossdressers

This story is a work of fiction, all characters are fictional and obviously the events are fake. You may reprint this as needed, just give credit to the author. If any differences occur between continuity, accept the one you like better as truth, and enjoy! Here's the last recap for you loyal readers out there (I apologize for the delay, life got hard, un...

Aunty's Toys Ch. 02

by novelcriss on Mar 25, 2019
Fetish

**Thank you everyone for reading and taking time to vote on Ch. 01. Do please feedback. I hope you like the evolution in Ch. 02. It has taken a lot longer to get going than planned!** ***** Simon stared at his phone in his office, not quite comprehending. Sally or Aunty as she'd told him to call her had sent him a text. "Simmy dear, don't forget your app...

Somewhere else.

by latexdoll on May 23, 2010
Fantasy

Waking up this morning I bet you didn’t know it would be the last day you spent here on earth. Climbing out of bed you hit the alarm clock for the third time, you can’t quite place what is wrong, you just can’t seem to get out of bed. Getting ready for work is more of a chore than usual. For whatever reason nothing seems to want to cooperate. Your shower hea...

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My Glorious Transformation Pt. 01

by switchhitter420 on Sep 18, 2017
Transsexuals & Crossdressers

My first stab at erotic literature, let me know what you think! Part one of a serialized fantasy journey into sissy faggotry. ***** About ten years ago, I ended a pretty serious, 1-year relationship with a woman I had met while working at a bar. She was this classic beauty: elegant, dirty-blonde hair, thin frame, striking facial features, an amazing ass an...

Alex, The Closet Sissy

by Areallysissyboy on Feb 11, 2019
Transgender & Crossdressers

My name is Alex, a closet crossdresser. 18 years old, never had a date. Too skinny, too weird, too feminine. I wore my hair long but not a hair on my body tho, not very athletic. Just a 5'3" skinny 125lb pale white boy with long black hair. Who loves dressing like a girl every since my older sister, Sam, moved out 1 years ago which left her old room unsuperv...

Desiree and Big John

by desireethtttv on Sep 12, 2017
Transsexuals & Crossdressers

It had been only a week since I'd introduced "Desiree, the Hot to Trot Transvestite" to my girlfriend Suzie, leaving me not a bit surprised that she chose not to spend the very next weekend at my place. While she hadn't freaked out, she was concerned I was gay since I was so convincing but I assured her I was not. I planned on revealing the truth I'd been wi...

A Tale of Misfortune

by AstralRider on Aug 25, 2017
Fantasy

Update 1: Story revealed. Update 2 will host several chapter depths to a path or two. Stay tuned! Preface: This story will take you down different roads rather you are a male or female. Generally the same sort of kinks will play out with differnces peppered around to make them unique in some fashion. The end story should be different regardless what path you...

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Hung like a Grape Ch. 02

by sissysherry2 on Apr 10, 2018
Transsexuals & Crossdressers

The story of our sissy heroine continues... We left things in the last chapter where a female coworker uncovered "Sherry's little secret" and proceeded to humiliate and dominate her. This is part two of three. Thank you to those who reached out for suggestions and hope you enjoy this chapter. I am still new at this and appreciate any guidance either below or...

Planet Pretty Sissy

by Hayleykim on Aug 18, 2017
Fetish

Louise ordered her kinky slave to stand naked in front of her. He was in his late forties, about eight years older than the pretty blonde, who had him like putty in her hands. "Welcome to your ultimate fantasy. We don't take passengers on this parallel planet. Is that perfectly understood?" said Louise. "Yes of course, Louise," he replied in a stuttering w...

A day in wonderland

by BadUsername1 on Jun 26, 2015
Fetish

You awaken in a strange room in a haze. Your vision is foggy and you become aware of your body, you feel it dragging as you get up to move. You rub your eyes and your vision clears up. Your first sight is the floor below, its a white and black chess floor pattern. You follow it with your eyes up to the wall, its a regal beautiful pattern, a deep red. Somethi...

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