Sissy Gangbang Stories

10,687 results
Orientation
Length
Source
Infinite Scroll

Wishful Thinking

by Artican on Dec 20, 2001
Fantasy

The day is bright and sunny. You are on your way to school, taking your time to appreciate the sights of the bustling people moving around to get to where they might need to be. Upon passing an alleyway, you are alerted by a muffled scream of distress. You move in to investigate. You discover a girl. Her clothes are shredded and there is a large thug looking...

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Bdsm adventures

by Sgtwolf on Dec 7, 2017
BDSM

This story is for a compilation of many different bdsm adventures. It was formerly known as latex adventures, but as chapters developed they dealt more and more with different aspects of bdsm, and less consistently with latex. Latex still exists as a strong element in many of the chapters, namely because I like to write about characters wearing it. I created...

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A New Spin on Role Playing Games Ch. 02

by shawnavinyltv on Nov 19, 2018
Transgender & Crossdressers

The next LARP event came by and I was more than ready! I was so horny and worked up I could hardly believe it. The last session had been such an amazing time and this one promised to be more of the same, and then added twist of me being the prize for one of the guys was just well, scary, but also a bit of fantasy come true! I did make sure to do all of my n...

Escapade

by Da_Vida on Sep 13, 2017
Transsexuals & Crossdressers

I'll never forget Homecoming this year. My boyfriend, Blake, came by my dorm to pick me up around 6 pm. He was in a very excited state and I could tell something was in the works. I asked him why he was so hyper and he told me that he was about to win the sex escapades, which was an annual challenge his fraternity put up each year to its members. There was a...

Candi is a Sissy Cam Girl Ch. 01

by CandiCumminz on Jan 15, 2019
Transgender & Crossdressers

This is the 6'th story in Candi's tale. Please read the Candi's conversion series and Candi Gets an Upgrade for the full picture of what's happened so far. - Hi! My name is Candi Cumminz and I'm your new favourite bimbo sex-doll. My camera's always on and I'm always horny so stop by any time for a good time! I love dressing up for my fans and putting o...

Opening Him Up Ch. 08

by humbleboy on Sep 14, 2017
BDSM

A couple of days had passed since they boarded Rachel's ship and they had the gangbang. It was almost dinnertime and Amy was in C5 with her slave. He was tied up and gagged. Amy was in a comfortable dress sitting on a chair across from her slave pondering what things were going to happen to him. There was a knock at the door. It was the Captain. Amy yelled,...

Aspiring Actress Ch. 04

by Tosshhh_ on Dec 3, 2019
Exhibitionist & Voyeur

The Premier was coming this Friday. It had been weeks since he had discovered the extent at which his girlfriend had committed to her role. He thought of nothing else besides the fact that his girlfriend had spent the past couple months fucking other men. He wrestled with the idea that soon she would be fucked by these men and their huge penises on stage. He...

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...

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

Sissy's First Gangbang

by TaykenByDaddy on Sep 12, 2017
Transsexuals & Crossdressers

I had been seeing Daddy Larry for over a year at this point. He was the third cock I ever sucked and the one to claim my sissy virginity by being the first to fuck my ass. He was exactly my type; early 50s, stocky hairy build with a small gut and over seven thick inches of manmeat that wanted nothing more than a younger guy to drain his load. The more femini...