Risque Sissy Stories 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 Prince: Origin Ch. 02

by SatinSlip on Feb 6, 2018
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** "I'm sorry about this." Jentif whispers in the Elf's ear. Larallin gives a slight nod. The big red woman was actually quite nice, and the wife of his new friend Oliver. But, like the rest of the slaves, she would do anything their monstrous master ordered. The ginger, Elf man...

Indoctrination 03: Starlet

by cuck4Traci on Sep 25, 2017
Fetish

"Ya know," I said to my wife, "I'll bet this movie was a little controversial in its time. The premise of a woman sleeping with two separate men that knew about one another had to be pretty risqué back then." We were sitting on the sofa watching Paint Your Wagon, an old musical comedy in which two unlikely prospector partners share the same wife in a Califo...

Limits

by The Style Guy on Apr 14, 2020
Loving Wives

Author's Notes: Recently, TheMarlboroMan, one of my favorite authors, has introduced right-wing politics into his stories. The overall political bent got me thinking about stereotypes and how they might play out within the cuckold lifestyle. As I outlined this story, Chris, a Trump supporter and Rush Limbaugh fan and his business partner Ben, a long time B...

Dominating Ken Pt. 01-04

by oneguy4fun on Sep 26, 2017
BDSM

Part 1: The Online Encounter Story Overview A thread of e-mails quickly blossoms into an erotic relationship of domination and humiliation between Ken and Karena. Karena develops a growing need for power and control while Ken finds himself drawn into a state of submission and inferiority. * Ken anxiously opened his e-mail to see if Karena had responded...

Enslaved by an App Ch. 10

by sadkins116 on Mar 20, 2018
Illustrated

I want to thank all the readers who voted, commented and offered their suggestions. Unfortunately, I'm afraid that Rebeccasm has moved on and will not be providing any more art to this series. I want to let everyone know that as far as I know it wasn't anything to do with the stories but it appears that she has moved on. I am submitting this chapter with all...

Virgin Fix

by UltimateHomeBody on Jul 30, 2019
Romance

Any similarities between this and real people is coincidental. If you recognise yourself here, feel privileged. All sex participants are at least 18. It has taken me a long time to get this written, then I read a similar plot. Oh well, guess great minds think alike, or all shit moves in the flush. not sure which. I have rarely beaten around the bush with...

Courtesan Ch. 07

by Goodhusband on Sep 19, 2017
Loving Wives

This is the seventh episode in a series entitled "Courtesan". If you have not read the previous six episodes of this series, I encourage you do so before beginning this chapter. "Courtesan" is romantic story about a dominant hot wife and her submissive cuckold husband. While they have a deep and abiding love for each other they do lead an alternative lifest...

I Fell in Love with a Ghost

by qhml1 on Sep 19, 2017
Romance

This is not a Halloween story. I just added the bit at the end in honor of the holiday. Hope you enjoy. ................................................ He just showed up one day, and the bar owner did everything but kiss his ass in front of everyone. He even set up a small table in the back near the restrooms, and no one was allowed to sit there except h...

Pharr Flung (Well Hung) Tours

by SandyMarl on Mar 31, 2020
Humor & Satire

Author's note: I believe this whimsical tale best fits the category of Magical Realism; alas, although such a category exists in the broader world of literary genres, Magical Realism is not a choice available for submissions at Literotica. I have chosen to place this story in the Humor & Satire category, as I am hoping the dear reader will find the absur...

Jackie and Artie Ch. 02

by Goodhusband on Sep 18, 2017
Loving Wives

This is the second episode in a series entitled "Jackie and Artie". If you have not read the first episode of this series, I encourage you do so before beginning this chapter. "Jackie and Artie" is a romantic story about a dominant hot wife and her submissive cuckold husband. While they have a deep and abiding love for each other they do lead an alternative...