Sissy Maid Punishment Stories

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Infinite Scroll

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...

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...

Threshold of Desire Ch. 4

by Cuthbert on Sep 19, 2017
Fetish

Chapter 4: Maid service Three weeks had passed since our last 'special' time, yet it still angered me when I thought about your transgressions that evening. Your first transgression, of 'forgetting' to shave your face as directed, had earned you a fitting punishment – being made to shave your legs, balls, and pubes as a 'reminder.' But the second transgress...

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...

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...

The Collaring of Chloe Ch. 13

by MemoryofSnow on Sep 18, 2017
Novels and Novellas

Chapter 13 -- A Maid Man **Characters and text are protected under copyright law The hot burning in Chloe's rear end tingled like a million tiny pins as she went about her work fixing lunch in the kitchen. It had been a couple of hours since Master had taken her to the Dungeon that morning, but the glorious spanking that he'd administered had left her rump...

Training Aide Ch. 03

by Angelscuck on Sep 14, 2017
BDSM

Just as the class started to break, one of the women said, "Great, I really need to pee!" "Wait a minute," Mistress Elaine announced. "We can use this as part of our training. It's called "Human Toilet". A plastic tarp was placed on the floor and I was positioned on top of it, on my back and ordered under punishment of canning, not to close my mouth. The w...

Mistress Chronicles Ch. 03

by MistressMtoyou on Sep 25, 2017
Fetish

Title: Decision time Background/update Even if you've been following the last couple of stories about my subject, Muffin, you might want to read this background as there are a few new points of note. Muffin is slightly heavyset, 36 years old, about 5' 7" and 160 pounds. He is quite submissive and seems to be aroused by a number of fetishes, but he professe...

Mistress Chronicles Ch. 02

by MistressMtoyou on Sep 25, 2017
Fetish

2 – Hurry Background/update In my last story, my new subject Muffin and I had our first live session. He is slightly heavyset, 36 years old, about 5' 7" and 160 pounds. He is quite submissive and seems to be aroused by a number of fetishes, but he professes to be most interested in being gradually transformed into a sissy maid and forced to serve in variou...

Jacki's Bitches

by reddbunnz on Sep 15, 2017
BDSM

Chapter One: Carol's Parents Return Carol was sitting in the parlor of her Uncle Rob's home awaiting the arrival of her parents. Carol, an 18 year old high school senior, was staying with her Uncle and his girlfriend, Joy, in order to finish high school while her parents were on an extended, three-month long European vacation. Carol was not only wanted to s...