Sissy Shemale Captions Stories

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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...

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:...

Twenty-Two More Questions

by silkstockingslover on Jan 20, 2020
Reviews & Essays

Twenty-Two More Questions Summary: 22 questions asked by readers answered. NOTE: Thanks to Tex Beethoven and Robert for editing. I wrote the essay Twenty Questions in December 2017 and Twenty-one More Questions in 2018. I answered the following questions, in case you want to read them. 1. Are you really a teacher? 2. How often do you wear nylons? 3. Wh...

A Latex Crossdresser's Dream Pt. 05

by shinyglove on Nov 18, 2019
Fetish

Please read A Crossdressers Dream parts 1-2-3& 4 before moving on to this story. *** The party was certainly in full swing as we had all seen some sort of action. The room smelled entirely of sex and latex, I was very happy with this as the aroma of rubber turned me on. Every time I opened the bag where I kept my latex collection the smell coming from it w...

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...

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...