Sissy Maid Chastity 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

My roommate new sissy maid

by Carterdruzba on Dec 29, 2020
Interracial

I been living with Gina who happens to be muscular and stronger than me I haven’t paying my rent for 2 months so one day when I meet her in the living room “you been not paying for months so I have idea for you to repay me so I got this” it was a pair of pink panties heels and black stockings and a maid dress “I decided to should be my maid until you paid me...

The Sissy Trap

by Slavedogg on Apr 29, 2025

As you struggle hopelessly your black leather restraints locked shut tightly making escape impossible. You have to wonder what you did to wrong to end up in this situation. Yes you wanted to be a sissy maid to a Dominant couple, yes you wanted them to use and humiliate you. You was the one to search and suggest this to your captors but now they are talking a...

Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...

Maid for Cum

by slcmalemaid on Aug 18, 2017
Fetish

The first thing one notices is the spent condom. This would normally be a very odd thing on a kitchen counter. However, I am not only not surprised, but I expect it. Next to the condom is a list of cleaning chores. And there I am, alone in a slutty french maids uniform getting ready to clean the house. How did this turn of events happen? Well, one night, a...

Sissy and Missy

by ChristopherDB on Feb 12, 2019
BDSM

Copyright 2019 Christopher D.B. * The central vacuum system made barely a sound as I made my way through the apartment. It was spacious and occupied the entire third floor. Although fully furnished and containing some of Countess Tori's personal items, she only stayed here a few nights a week. My feet were hurting, as the toe box on my pumps fit a little...

Sissy School

by zeta515 on Jun 19, 2018
Novels and Novellas

Copyright 2018 by Zeta All rights reserved This story may be freely distributed in electronic form but must include this copyright. Sissy School is a work for pure fiction and all locales, names, characters, places, and incidents are the products of the author's imagination. Any resemblance to actual events, locales, or living persons is entirely coincide...

The Chastity Trap Ch. 02

by slavemalcom on Mar 13, 2018
BDSM

Malcom rushed back through town to his house, all he wanted to do was get to his room and see what could be done about the chastity device trapping his cock. As soon as he opened the door however, Emma came rushing out of her room and looked down from the top of the stairs. "Lott...Oh it's you." She said. She didn't even try to hide the disappointment and d...

Erin Ch. 15: Perfect Sissy Cuckold

by Graves94 on Nov 16, 2020
Fetish

Erin Ch. 15: A Perfect Sissy Cuckold By Jonathan Quincy Graves {Note: This is the fifteenth in a multi-part story series cataloging the progressive evolution of a relationship between a dominant woman who provides leadership and discipline for her husband. Each installment can stand alone, but they read much better if you start at the beginning. Go to: Eri...

My Teasing Hotwife Ch. 05

by footslave85 on Mar 26, 2019
Fetish

Part five - watching the fun I had just finished getting everything ready when I heard a car pull up outside and I quickly rushed back to the living room to wait for the new lovers to arrive. I just made it back into the room as the front door opened and they walked in holding hands. I saw my wife was a little tipsy and had a big smile on her face and I cou...

Transforming Brent

by sissymissyct on Jul 9, 2019
Loving Wives

Katherine decides she wants to live with her lover Wendy. They come up with a plan to slowly change Wendy's husband, Brent, into their girly sissy maid full time. Will his resistance be broken? I put it in loving wives but it fits multiple categories. Will he will learn to love his new role in life? Yes, The narration switches between characters. If this bo...