Sissy Bondage Maid 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

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...

Sissy Shopping

by Candour on Sep 25, 2017
BDSM

My first story, finally edited and tidied up. I hope you enjoy it, I enjoyed writing it. --------- You were standing in your local department store in the make up section, looking for foundation. Not too sure what you are doing, and must have looked a little lost as one of the sales girls came up quietly behind you. She was a delightfully pretty 18 year ol...

Cyber Sissy Ch. 05

by missvicky53 on Sep 25, 2017
Fetish

A fantasy by Miss Vicky Part 5 (The Last One) The rest of the evening passed with the two of us cuddling on the couch, each with a glass of wine. Megan had changed into a black floor length nightgown with a lace inset running diagonally across the front. This meant that with each movement of her body, I would catch a glimpse of various parts of her body. T...

Cyber Sissy Ch. 03

by missvicky53 on Sep 25, 2017
Fetish

"Good, you may begin by repaying my hospitality. I want you to clear the table and rinse the china. You may then put everything in the dishwasher. When you are finished, I will continue your training." I obeyed at once, being very careful with the china. I wondered where Megan was while I was doing my domestic chores. The answer to that came a minute later....

Mistress Natasha

by maidevie on Sep 26, 2017
BDSM

The soft black and chrome leather bustier pushed Natasha's breasts upward to astonishing heights; the mounds of soft flesh trembled with every step that she took. John sucked in a deep breath as she walked towards him. She was truly a Goddess. Her legs were on display in black thigh high vinyl boots, the heels of which had to be at least 6 inches high and de...

The Unsuspecting Candidate Ch. 03

by missvicky53 on Sep 11, 2017
Fetish

I awoke at 6:00 A.M. and set about preparing for my sissy's surprise. I opened the door to see him there on the bed, his ankles and wrists still cuffed to the four corners of the bed. His head was still encased in the bondage hood and he lifted it as I shut the door and approached the bed. "I trust my sissy slept well," I cooed as I began to release him fr...

The Unsuspecting Candidate Ch. 02

by missvicky53 on Sep 11, 2017
Fetish

Part 2 Helen continues Mike's training, this time in a French Maid's uniform The aftershocks of his climax were still coursing through his body as I teased him. "Did you have a nice cum, sissy?" I cooed at his still bound form. "Do you want me to release you now?" "Yes, please," he replied. "I'd like to get dressed now." "And get dressed you shall," I tea...

Devoted Cuck Ch. 02

by cuckyfucky on Dec 18, 2018
Fetish

This is Chapter 2 of my ongoing series. Chapter 1 can be found in my profile. ***** I was cleaning the kitchen in my sissy maid outfit when the phone rang. Seeing it was Lina, my wife, I immediately picked it up. "Hi cucky, are you finished with your chores?" she asked. I could hear music in the background and so I knew she was still at the club. "Yes L...

Mistress X 02: Pixie's Predicament

by Long2bLocked on Jan 22, 2019
BDSM

Note to readers: This short story is not part of any series. The setting and characters are based on those from my "Laura's Femdom" stories. My Mistress X stories stand on their own but are best read in order. This particular story describes a predicament bondage session. ***** Mistress Alexis X has a female live in slave named Pixie. She works at Red Ro...

Inquisitorial Interrogations

by EstebanMamono on Oct 19, 2020
NonHuman

It started as a monstergirl chronicle/encyclopedia and turned DID-Bondage-BDSM-Drowsploitation-Bisexual stuff. Sorry, my bad. Still, I intend to add more vanilla monstergirl sex later on. Enjoy, fuckers. - Esteban de Chucha ***** Inquisitorial report: Subject: Human male, age 28. Well educated, local clerk, locksmith and jeweler. Married, has no child,...