Sissy Gifs Stories

6,670 results
Orientation
Length
Source
Infinite Scroll

It's a Sissyful Life

by sliderx on Aug 23, 2015
Fetish

John sat in the basement, football on the TV, 4chan on his laptop. The game was pretty much a blowout, so he wasn't really paying attention. He was, however, greatly interested in the adult gifs (although 90% of the entries were webms) page he was on. There were a few threads that were catching his eye, girls playing with their asses, deep throat, but he was...

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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:...

"Sissified": 12 Days of Sissy-mas

by silkstockingslover on Jan 7, 2019
Transgender & Crossdressers

Summary: Straight man is turned into a submissive sissy by.... Note 1: This is my 400th story release. To mark the occasion, I thought I would try something longer... mixing many of my themes into one long, complex story. Thus be warned that with over 40,000 words, this story is a marathon not a sprint, and it includes a variety of themes including: cross d...

A Sissy's Halloween

by Evangeline_E on Oct 29, 2018
Transgender & Crossdressers

Disclaimer/authors not: All characters in this story are over the age of eighteen. This is my first story so criticism is wanted as long as its constructive. I make these stories based on what I want and my own sexual fantasies. Thank you 😊 . * To tell this story right I need to start at the very beginning, the time where I first started to question my se...

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...

Surviving the Mirror Dimensions

by DefeatedDamsels on Apr 22, 2025

Having written a crazy number of chapters without publishing this, the first ones written in late 2022, I finally (August 2024) have decided to at least publish what I've done so far, even though it's so incredibly incomplete. Hopefully you agree it was worth me doing so. If you reach the end of an incomplete branch in Dr. Willow's world (the first world you...

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Castration threat image inspiration

by EYEsoul2 on Apr 22, 2025

Images or gifs of ballbusting or castration threats that might inspire you to write a story. Feel free to add photos or gifs also feel free to add stories. (May also add sections for character based images but unsure also might add a section for cuntbusting)What's next? Need to pop them Better start lifting...

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House of Kinks

by royal22erick on Dec 24, 2019
Fetish

The house of kinks is almost as old as the oldest profession in the history of mankind, its creation was founded upon three unrefutable principles. 1- There will always be a market for the pleasure of the flesh and the house of kink always need to be in touch with the populace needs. 2- No House of Kinks manager should seek power at the detriment of the hous...

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A Cruel Commonwealth

by JohnFlow on Apr 29, 2025

Thank you so much to everyone for reading my story and showing your support through likes and comments here on CHYOA.com. It makes a major difference when it comes to my motivation to write new chapters. I've also recently made a patreon for anyone who would like to show their support, please head over there and check out the different memberships with some...

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Doll House

by TheAiMastermind on Apr 29, 2025

The black market isn’t what you think it is. Sure there’s guns, ****, and all kinds of unspeakable horrors. The biggest thing purchased though? Dolls, and no not the handheld toys. Our job is the remodeling and rebranding of people. Have a bitchy boss who never shuts up? Send us your oder and we’ll take care of it from there. By the end of the week that boss...

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