Sissy Fisting Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Sissy Powers Ch. 14

by ClarasBestFriend on Sep 29, 2020
Sci-Fi & Fantasy

When I woke up the next day, I smiled as I felt Clara's arm resting across my chest, indenting my breasts with a pleasant pressure. It was amazing being a woman; every part of my body felt electric with sensitivity. The slightest touch, which before would have been completely inconsequential, now gave me a staggering amount of stimulation. I wasn't really su...

Sissy Powers Ch. 13

by ClarasBestFriend on Sep 29, 2020
Sci-Fi & Fantasy

"You know, once you take my ass, there won't be a single one of my holes that another man could use..." Heather moaned, overcome with arousal at the thought of belonging to me so totally. "Uh, what about your mouth, babe?" Clara teased from slightly to the side, rolling her eyes at the overly horny girl forgetting one of her own fuck-holes. "Nuh-uh, becaus...

Black Sissy For Black Dominatrix

by Samuelx on Sep 1, 2017
Group Sex

As a Black mistress, I totally love it when my Black male Sluts dress up for me. Gleefully I slid my strap-on dildo into Reginald/Slut Gina's ass while spanking him and cussing him out like the bitch he is. The big Black dude is now wearing a frilly pink dress, red panties, stockings, and a wig, and his ugly mug is well-made up. Transforming macho Black truc...

Simon Sissy Slave Ch. 01

by Timewarp10 on Jul 30, 2019
BDSM

It was late summer in 1964, and it was Simon's first day at his new job. Simon had read his letter of appointment several times; and he held it in his hand now, standing anxiously outside the imperiously heavy door, embossed with "Post Room" in faded gold lettering. The door was probably victorian, Simon judged, and perhaps it had been a post room for many d...

Simon Sissy Slave Ch. 03

by Timewarp10 on Jul 30, 2019
BDSM

Mr Berne watched with satisfaction as the sissy paraded in the post room. Sissy walked gracefully in high heels. His ballet training made it easy. He knew how to walk like a woman. He had practiced, and he could walk with a book balanced on his head. It gave him poise, and the high heels gave elegance to his calves. The skirt was short enough to look slutty,...

Simon Sissy Slave Ch. 04

by Timewarp10 on Aug 20, 2019
BDSM

Simon staggered in for work the day after the slave auction, his body stiff and sore. Mr Berne and the others in the post room were shocked to see the sissy's bruised and lacerated buttocks. Barry's stiff cock betrayed his feelings; whipping and torture excited him. His sadistic nature relished the thought of thrashing Sissy senseless. Sissy was his fuck t...

HypnoSissy: Cum Cravings

by silkstockingslover on Sep 26, 2017
Fetish

Summary: Videos entrench his hunger for cock and cum. Note 1: Thanks to hfernandez1983 for the story idea and the intriguing revelation that hypno sissy videos exist. Note 2: Of course, all participants are at least 18-years-old. Note 3: Thanks to TexBeethoven, Robert, and Wayne for editing this chapter. Apology: This part was originally announced as bei...

Slave Ch. 02

by slaveheathen on Sep 25, 2017
Fetish

Chapter the Second Just a note: This story contains bisexual sex, fisting, bondage, piss play and more. That's why it's in the fetish section. If this isn't your cup of tea, don't read it. If it is, enjoy! Now, on with the depravity... As I knelt there on the piss soaked blanket in my piss soaked clothes, I tried to gather my wits, not to mention catch my...

Jack and Jill Pt. 03: Anna

by candyflosslover on Jul 13, 2020
Loving Wives

The next day Jill was at work in her office, a parcel had arrived for her and when she opened it to her delight she saw it was a double ended dildo. She had ordered it some weeks ago so she could use it with her sissy husband. It was longer and thicker than she imagined and she felt heat between her legs at the thought of what she would do with it. She was s...

A Mistress to Obey

by gbr2004 on Sep 12, 2017
BDSM

This story involves bdsm action, forced bi, pain and humiliation. Not your thing? Please pass on by. * I met her online. She was older like myself and was looking for a submissive man. We exchanged a few emails but she really wouldn't say much about what she was looking for and expecting from her sub. In her profile she said she was into such things as bo...