Sissy Whores 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

Girl's Night Pt. 04

by DifferentBreed on Sep 14, 2017
Fetish

"You want to cum too, don't you bitch?" Sophie said. "But pleasure is only reserved for Mistresses and Dommes. Not sissy whores like you." Sophie looked down at him, grinning evilly, turned on by the lips descending her body and the sight of him kneeling there in sexual servitude and agony. She let her hand fall lightly on the back of Jenny's head as she fel...

A New Toy

by keptsissy on Sep 13, 2017
Fetish

I love this view. It never gets old. I watch the top of his head. I see his tasseled brown hair as his mouth moves back and forth on cock. I see the curve of his perfectly rounded baby smooth cheeks, ever so slightly spread by way he arches his back, his butt perched up on top of his heels, his toes dug into the carpet as he kneels in front of me. I hear him...

The Audition

by bitomah33 on May 7, 2019
BDSM

His heart was beating so hard inside of his chest that he could no longer think clearly. He just realized they really did not plan out this scene ahead of time. He was so drawn to her energy that most of his rules regarding safety were ignored. For some strange reason he trusted this stranger, as if they were intimately involved in a former life. He was begi...

A Sucker for a Stud & His Woman

by Cute Little Thing on Sep 14, 2017
Fetish

Alex . . . Treat me like your sissy slave: Bisexual, Gay, Femdom, domination, humiliation, anal sex, cum, glamour girls. Alex has success with all the ladies, and allows Jeremy to tag along on one of his conquests. Jeremy soon realizes that in sexual situations with Alex, everyone serves Alex's dick - be they a man or a woman. Hot humiliation and bisexual ac...

Sissy Plays the Game of Thrones

by SissyKelly on Dec 1, 2017
Celebrities & Fan Fiction

Kelly Waters, fucking Waters I thought to myself as I shook my head. I think the worst part of being a bastard is knowing you could choose any last name, but having it dictated still by birth. I knew not who my parents were, in fact I only knew I was Kelly Waters thanks to the man who raised me, Lord Petyr Baelish. I was born in his house, his whore house,...

Sissy Plays the Game of Thrones Pt. 02

by SissyKelly on Dec 1, 2017
Sci-Fi & Fantasy

The small man stood in front of me, I was sat on the bed, the last thing I wanted was to stand and make him feel small. Being small was for girls, not boys, I thought to myself. "Miss Waters, it is such a pleasure to meet you. My oh my are you beautiful." Lord Tyrion said. I blushed. I was sat in a black corset, my cock flicked up and hidden in my black un...

Sissy Prince: Origin Ch. 01

by SatinSlip on Feb 6, 2018
Fetish

Prince Oliver skipped through the castle garden. He loved the green and the flowers. He was nineteen and yet to be married. In truth his parents had coddled him as a boy. He knew his numbers and letters. He knew how to run a castle and a kingdom. On paper anyway. But he would never be a warlord. Never be a brave leader of men on the battlefield. His gold...

Sissy Prince: Origin Ch. 03

by SatinSlip on Feb 13, 2018
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** Olivia pulled off his scratchy wool tunic. It had covered him to just below his cute girly ass. It was uncomfortable to wear, made by Orcs. Yet for some reason it turned him on. His tiny sissy bump was now revealed to the world. It was erect, yet not quite two inches long. He...

Julie is a Whore Ch. 06

by Pretty_Sissy_Julie on Jul 14, 2020
Fetish

Ch 6 Hello, my name is julie and I am a sissy CD. I am very passable and by the time of the events in this story took place and I had a nice bra size of 34B. This is a difficult story for me to write because I am going to write it in 3 parts. The first 2 parts will seem to be unrelated, but hopefully the third part will tie it all together. Just as a warnin...

Back-alley Sissy Boy

by Travel_by_day on Sep 12, 2017
Fetish

I saw you while I was walking through the grocery store. You were bent over, picking up something off the bottom shelf. At first, I thought you were a girl, because of your nicely shaped ass and the fact that your low rider jeans were riding down, exposing a lacy white thong. I was so turned on, my cock started to get rigid right away. If I had been wearin...