Smutty Sissy Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll

A week of

by Sissysub on Apr 29, 2025

||Reminder to make your nickname a feminine version of your name, sorry I made the default Faggella, I was horny but that’s probably not the best option, if you know how to change that please leave it in the comments|| Intro: Alex White’s mother, Jennifer, died when Alex was 15. But before that, she married an awful man, Dave, who Alex absolutely despised. H...

Whitewash High Ch. 03

by EnglishTeacher on Sep 25, 2017
Interracial Love

The couple turned towards the woman at the classroom door. Fresh cum dripped off of Principal Weiss' face, cumdrunk lust still apparent on her face. "You two are lucky I'm the only one in the building," Michelle said, walking over, shaking her head at the mess. "How long have you two been fucking?" CRASH! Michelle slipped on a puddle of cum, falling on...

Changing Destinations

by the Troubador on Sep 13, 2017
Loving Wives

As usual, don't read a Troubador story if you are looking for sex. This is different from my usual story, but I think you'll know the people I'm writing about, like some of them and dislike others. _ _ _ _ _ _ "Dammit! Another big week planned with Susan, another 'emergency' call from the boss!" thought Darwin as he hefted his big portmanteau in one hand,...

The Long Resignation Pt. 01

by AndersonCoombs on Oct 22, 2019
Exhibitionist & Voyeur

Chapter 1 – The Surface The dream had always repeated itself with a surprising specificity. Nicole was at the bottom of a pool – the kind with those miniature tiles, mostly white with the occasional blue tile in the mix for the sake of contrast. She was never quite sitting on the bottom, just drifting, fluid like the water all around her, inches from the ti...

Faye's Official CHYOA Story Contest 2025

by Spindizzy on Apr 29, 2025

Hey there, sexy readers, it's me again, Faye, your faithful flirty filthy CHYOA librarian. Gosh, it's been simply ages since we've had a chance to chat, but I've been so busy filing away all your delightfully dirty stories I've hardly had a moment to relax. What I really need is a little me time. A chance to unwind with my favourite toys and the highest qual...

School Doctor Strips Schoolboys

by aaronburr on Feb 6, 2018
Exhibitionist & Voyeur

It happened over breakfast, in the Marcello household in Upper Elm. And it came from Johnny's sister. Without warning, in front of their Mom, as they ate their Corn Flakes, she said, "The boys at school? Like Johnny?" That's all. "The boys at school? Like Johnny?" And she let the question hang there. They were all at the table: their mother, Johnny's yo...

Mistress Joan Ch. 01: Punishment

by slutty_sissy_nikki on Mar 10, 2020
BDSM

BASED ON A TRUE STORY! All characters are over the age of 18. This is my first short story and I welcome constructive feedback. PRELUDE The cane cut through the air to deliver another mark onto my plump bum. I tried, unsuccessfully, not to flinch when I heard the wish sound of the cane travel through the air. Knowing it was coming was the worst part, or ra...

Wife in Control Ch. 06

by wifetoy on Sep 25, 2017
Fetish

I will bring you your Magic Wand and Trigasm. And suck on your toes, while you enjoy every spasm. Your humiliated sissy in panties, tights, and stilettos. This is the sixth chapter of my wife's execution of the punishment poem I submitted to her suggesting ways to atone for my inability to control my orgasm. Please read the earlier chapters for the full...

Thank You Miss 'Nessa

by Cleverlicious01 on Sep 13, 2017
BDSM

Of one thing, Vanessa was most certain: She savored the feeling of taking a typically, naturally dominant man, and turning him into a servile sissy. By chance, Mike already happened to have the secret calling encased in his DNA. His alpha male appearance, with lean muscular physique and beaconing hazel eyes, would have made any other woman weak in the knee...

A Mistress to Obey Ch. 04

by gbr2004 on Sep 12, 2017
BDSM

This story includes female domination, forced fem, forced bi and discipline. Not your thing, please find a different story. I follow Mistress into the playroom wearing just the thigh high nylons and heels. I'm so hoping she is in a good mood after watching her have several orgasms with Terrell. Maybe she will be in a more playful mood, hopefully, thinki...