Sissy Shemale Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll

Our Only Hope Ch. 03

by The_Technician on Dec 16, 2019
BDSM

This is Chapter Three of a book. The characters and situations will be more understandable if the previous chapters have been read. Because it is a book, some of the chapters are more exciting than others, and some situations do not complete until the next chapter. I could have run this through my regular publisher and made a couple hundred dollars, but I am...

The White Slave

by mspbottom4black on Oct 6, 2020
Interracial Love

Editor's Note: this submission contains raceplay and femdom content. * Not long ago it was a straight and stuffy white male. it was arrogant and self-satisfied with its white male social and economic leverage and advantages. In the rat-race of white society it suppressed its submissive white side. But from time to time it would slip into daydreams of hav...

Vanadis And Viramare

by FutaHime on Apr 22, 2025

Everything had gone to shit. It was supposed to be an easy job. A quick payday. Van and his team were going to head out to find this rogue Warlock, take him out, and grab up the generous bounty. Why Van and the team thought everything would be as simple as that… Who knows? Too many easy jobs? Too long on the road without a break between jobs? Whatever the re...

Sissy/Cock Sucker Dictionary

by silkstockingslover on Jun 12, 2019
Reviews & Essays

Summary: A list of terms to aid in understanding the activities and nature of sissies and cock suckers. Note 1: The author's source material isn't Webster's Dictionary or anything similar, but is drawn from many years of interest in matters sexual and countless conversations, both spoken and online, with other perverts. Note 2: Thanks to Tex Beethoven and...

Exploring My Fetish

by fetishguy81 on Jan 7, 2018
Anal

Note: This story plays off of my previous 2, taking place after both of them. You won't miss too much but you can get more of the backstory by reading my other 2 stories first. ***** I developed to rather uncommon fetish's in pretty uncommon ways through out my life. My first was a fetish around salon capes and haircuts in general. When I was younger I dre...

Locked down in a lockdown

by MrTwister5 on Oct 19, 2020
Fetish

Being a junior software developer, you were one of the first to be sent home when the first signs of the pandemic came up. While you thought that it’d be fun to hang out at the house while everyone else was at work, it soon became evident that everyone else would follow suite. By the end of the next two weeks, all five of you were working from home. At first...

Sissy Plays the Game of Thrones Pt. 02

by SissyKelly on Dec 1, 2017
Sci-Fi & Fantasy

The small man stood in front of me, I was sat on the bed, the last thing I wanted was to stand and make him feel small. Being small was for girls, not boys, I thought to myself. "Miss Waters, it is such a pleasure to meet you. My oh my are you beautiful." Lord Tyrion said. I blushed. I was sat in a black corset, my cock flicked up and hidden in my black un...

Teacher Made Me into Sissy

by johntamilandrea on Sep 13, 2017
Fetish

HI! I am Sissy Andrea. This is one my fantasies about my teachers. This story is about feminization, fantasy. If you don't like these topics Please don't read. ALL THE CHARACTERS IN THIS STORY ARE ABOVE 18 YEARS OF AGE. My special thanks to "mywifesslave" for helping me in editing this story. ***** The story happened when I was 19 years old I loved sho...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

A Sissy Saga Ch. 24

by Snurge on Sep 13, 2017
Novels and Novellas

The early morning sun made the windows of the great house sparkle, and the ancient, dappled walls of Fairyfield Grange looked like they'd been daubed with gold. Abigail swept across the back patio and admired the recent changes. The large windows facing onto the terrace had been taken out and replaced with French doors. It was a facet of his mother's ultima...