Gay Sissy Bondage Stories

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Infinite Scroll

Stevie's Journey Ch. 03

by gbr2004 on Dec 2, 2019
Fetish

I get up and put on some of my regular clothes, workout shorts and a t-shirt and flip flops. Try to digest what happened yesterday and how everything just spiraled out of control and now I find myself in this impossible position. It's like all choices have been taken from me and this group of people took over my life. It was exciting but I can't be doing the...

Wet Dream Pt. 03

by sissymissyct on Jan 28, 2020
Fetish

Gayle finished ordering items on line and checked the cam to be sure Georgia was asleep. The wetness in her panties told her what she needed to do. The payback for all those years that bastard cheated on her and how he had no idea what was coming to him, just made her pussy so wet. She was soon in bed enjoying her favorite toy. "I can't believe I slept so l...

Mistress Red Fox Becoming a Devotee

by His_fag_wife on Sep 24, 2019
BDSM

A story of what might have been a dream. Names have been changed. *** One evening I was looking through profiles on a BDSM website and came across one for a local Mistress, she was developing a new dungeon and she was asking for suitable subs for her to try it out on. Someone to test the new equipment and layout on. I read the ad over and over again, this...

Short stories and other tales

by Mr_anderson on Jun 3, 2023
Fantasy

Short stories and other tales Sometimes short is good too Synopsis A compendium of stories inspired by pictures or just ideas on the go. Chapter 1: Introduction I wanted to make a story where I wasn't bound to any premise, so I created this one. Every path bellow is a different story, a different context or universe. M......

More Than I Wanted

by gbr2004 on Sep 12, 2017
Fetish

This story involves man to man sex with bondage, discipline and forced fem involved. If not your thing, please disregard. Enjoy feedback and suggestions. Hope you enjoy. I need to tell someone about what has happened to me. My name is Steve. I'm 28, single white man, 5'9, 140 pounds, brown hair and blue eyes. I work out at the gym three days a week mainly...

Dan's Conditioning

by headrush274 on Jun 9, 2020
Illustrated

Miss Kendra was standing over Dannie, looking down, proud of her creation. Dannie was an excellent example of what a sissy ought to be. She was down on her knees, legs spread wide, in white thigh-high nylons. Her little sissy cock was dripping precum down onto her white mini skirt, as its head protruded out of the waistband. Miss Kendra strutted around Danni...

My First Visit

by gbr2004 on Jan 1, 2019
BDSM

This is fiction. Do not read if gay action and discipline aren't your thing. ***** I was nervous as I drove through Tucson on my way to meet a man I had met online. I saw his ad on Craigslist and he said he was into dominating other men. I emailed him telling him my interests in this but also told him about my lack of experience with other men. I had been...

Constantly Cucked Cloud

by princessjasminedoll on Mar 17, 2025
Fan Fiction

Constantly Cucked Cloud An FF7 Remake Fanfic Synopsis Cloud Strife is a man of multitudes. From a small town, he ascended to the height of SOLDIER. Now a mere mercenary, he tries to forget a confused past and land some pussy...any pussy. Chapter 1: Introduction Cloud Strife nimbly unzipped his fly on top of the train.......

A Changed Man Ch. 1

by sub5000 on Sep 12, 2017
Fetish

Part One - Beginnings It had to happen one day I guess. I had such a collection of porn on my hard drive, that it was inevitable that one day my wife would stumble across it. It wouldn't have been so bad if it was average, everyday porn, but my collection consisted of more 'specialist' images. There were pictures of shemales with big hard cocks dressed in s...

'Ween Contest

by Nathan_Brazil on Sep 3, 2017
Erotic Horror

Greetings to everyone! Yes, this is my entry into the Halloween contest. It's sort of a Satire/Celebrity/Erotic Horror piece with some gay sex, group sex, oral, and even some implied fisting. Yes, something for almost everyone in the Literotica family! Oh yeah, there's some Fetish too. I hope everyone loves it and I get to sell the film rights! * "Oh look!...