Sissy Caught Stories

167,051 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

Sissy Gets Punished

by MsMorrigan on Sep 16, 2017
BDSM

Once upon a time there was an overly eager sissy girl. This sissy girl loved her mistress. She loved her so much she tried to anticipate her every whim before she needed to even speak the words. One day the sissy girl was vacuuming, dusting and general cleaning. She was openly lamenting on how her overly large pathetic sissy clit was getting in her way. How...

The Dominatrix Order Pt. 02 Ch. 03 - Romance

by Jwwsmith on Feb 12, 2019
Transgender & Crossdressers

The next afternoon, Johanna invited many of the Goddesses of the Council over for lunch. Much to everyone's surprise, Representative Pencalia arrived as an uninvited guest. Pomona prepared a fine meal as the Goddesses deliberated over various issues. Pomona was very accommodating to the guests, serving them tea and salad and shrimp. She even placed cloth nap...

Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

My Girlfriend Made Me a Sissy Ch. 03

by libertinaXx on Sep 25, 2017
Transsexuals & Crossdressers

I lay on Jess' bed waiting for her and wondering what would happen for ages. She was in another room getting ready for her new lover, I was already dressed up. Pale blue, see through panties and matching bra, a short black skirt and a blue vest top. With my make up done to show off my pretty green eyes and my long brown hair styled wonderfully, I looked like...

Prankster Ch. 10

by Paris Waterman on Sep 15, 2017
Group Sex

Copyright © 2007 Many thanks to "Techsan" for graciously giving his time and effort to me in editing this and other stories of mine in recent months. As always, I appreciate your excellent support, thanks again, Techsan. Chapter 10 After letting the girls out of the van and escorting them into the warehouse, Tony made a couple of calls to old acquaintan...

Caught in Panties & Dominated Ch. 05

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

Cast Trace - me Tracy - me, dressed en Femme Rick - head of security at work, had just caught me masturbating at work, dressed as a woman Ken - my roommate Ok, ok, I hadn't mentioned this before, but my roommate Ken is gay. He would flirt with me from time to time, even hit on me, and I pretended to discourage him, but sometimes, late at night in my roo...

Sissy Maid to Be... Ch. 03

by missjennymaid on Apr 8, 2019
Transgender & Crossdressers

I would recommend reading the first chapters to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jere...

Alt. Queen of the Left-hand Turns

by maxdname on Sep 16, 2017
Romance

See that beautiful girl in the poster? When I first met her she was a simple hillbilly girl from Appalachia sleeping with stock car drivers in order to get a pit pass. Look at her now: she's a blond and a model with her own TV show that earns her more in a year than most stock car drivers will earn in a lifetime on the circuit. A national racing magazine i...

Sissy's Decline into a Slut Pt. 02

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Three: Another Exciting Night as Sissy Slut Wannabe. Well about a week has gone by since I bought the dildo, wrist cuffs, ice lock and the lubricants at the adult sex shop. Dressing up as a sissy maid or a sissy slut everyday at home and learning how to use the dildo first with my mouth and trying out the flavoured lubes for added pleasure, but most...

Black Femdom For Black Sissy

by Samuelx on Sep 11, 2017
Fetish

Sitting comfortably in her basement/dungeon, Ottawa's premier dominatrix Madame Whitley looked at her submissive, Shane Johnson, as the big and tall, formerly masculine Black dude stepped out. Clad in a pink Tutu, blonde wig, crimson pantyhose and high heels, the brother was finally letting out his inner slut. For years, Madame Whitley struggled to help Shan...