Sissymaid Stories

130 results
Orientation
Length
Category
Source
Infinite Scroll

Alice is Arrested and Goes to Jail

by sissymaidallyson on Sep 14, 2017
Fetish

Alice was a straight A student and was a total goody two shoes. She wasn't ugly but she certainly wasn't cheerleader material but was generally liked and respected by her peers and teachers at her high school. She lived in a relatively small town on the outskirts of Jackson Mississippi and was a happy child. She wanted to experience everything life had to of...

Writing Realistic Female Dominance

by stlgoddessfreya on Sep 13, 2017
How To

Scene 1 I couldn't believe I was doing it, even as I followed the tall blonde in the black PVC catsuit to the door with "Private" written over the door in tilting red script. I just went to the sex club to watch, at least that was my plan, but as soon as I saw her demonstrating the proper way to flog a man in a kneeling position, I knew I would be on my kne...

It Really Does Happen

by lipsticked on Sep 26, 2017
Fetish

This story is copyright 2009 by (lipsticked11). All rights reserved. No reposting without permission. * I am owned by a dominant couple and their niece and used as a live-in maid, cook, and sexual slave. My name was Michael, now I am Michelle. This is my story: When I was 35, my wife Connie and I lived next door to another married couple, Denise and Steve...

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...

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...

Cyber Sissy Ch. 01

by missvicky53 on Sep 25, 2017
Fetish

It was a Saturday afternoon when my submission to my wife began. Megan had gone to do some shopping at the local mall, and knowing her as I did, I knew I'd have at least three hours to surf the web. My favorite sites were those that dealt with the feminization and submission of men. With this in mind, as soon as I heard her car leave, I powered up my compute...

A Sissy Maid is Born Ch. 01

by catalina_francisco on Sep 13, 2017
BDSM

The soft darkness of the blindfold caressed his face, as he lay curled on the damp concrete of the barn where he had been ordered to stay. The cold surface beneath him penetrated his skin, crept into his flesh seeping through to the bone, chilling him as surely as the thoughts that flooded his brain as to what was going to become of him. Storm knew in his mo...

A Sissy Saga Ch. 09

by Snurge on Sep 15, 2017
Novels and Novellas

Miriam Hancock arose in the morning alone but feeling joyous and revitalised. But when her early toilet had been done her smile faded, and she frowned. On the dressing table lay the fat envelope she'd received that morning from the lawyers employed by Lady Diana. It enclosed a letter that was dreadfully succinct. '... Our client as brought to our attention...

Black Sissy For White Queen

by Samuelx on Sep 16, 2017
Interracial Love

I feel so damn great as I slide my strap-on dildo deep inside Ramon Jones. The six-foot-tall, skinny Black guy looks absolutely gorgeous in a bright pink dress, white pantyhose and high-heeled red shoes. His face is perfectly made up, rouged and his makeup and lipstick are applied nicely. The fuzzy black wig he's wearing only adds to his decidedly not so mas...

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...