Sissy Maid Training Bdsm Stories

85,925 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...

Sissy's First Day

by whispy_sub on Sep 13, 2017
Transsexuals & Crossdressers

Sissy let out a disheartened groan as he closed the classroom door. He looked down despondently at the discipline demerit clutched in his gloved hand, "It's my first day and already I screw something up; I can't believe this." It was only his fourth hour here at the Academy, and already he recieved a demerit. He wasn't quite regretting his decision to enrol...

Few of My Ultra-Perverted Fantasies

by whiteboibbclicker on Sep 16, 2017
Transsexuals & Crossdressers

Hello, I am a white boi who's addicted to sissy porn and have a lot of wicked and perverted fantasies. In this list, I will enumerate some of them. I would ask the readers to name the one that they like the most in the comments section so I can write a story about it. Authors are more than welcome if they want to write about any of the themes mentioned here...

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...

Domina Katarina Goes Shopping

by pbs444 on Sep 17, 2017
BDSM

Several days ago, there was an e-mail in my inbox. It was of course from my Domina, Katarina, because the e-mail account is for her exclusive use, when she wishes to communicate with me. Because I am her sissy slut, and from time to time she finds ways for me to prove my usefulness to her. The e-mail read: "Hello, sissy slut, I have decided I wish to go...

To the Manor Bound Ch. 02

by Nikki258 on Sep 26, 2017
Transsexuals & Crossdressers

This is part two of a series; you'll probably need to read part one to get a grip on what's going on. As with the first part this focuses on forced feminisation including aspects of BDSM and non-con, so if that's not your thing, now would be the time to leave. Chapter 2 -- The Next Day Peter was barely able to find a second's worth of sleep that first nigh...

To the Manor Bound Ch. 03

by Nikki258 on Sep 26, 2017
Transsexuals & Crossdressers

[So I finally got around to finishing chapter three, apologies for the delay. As with the other two chapters this includes forced feminisation, BDSM, and non-con, so it might not be your cup of tea. Regardless do comment and email me to let me know what you think, or just to say hello!] ***** Chapter 3 -- Three Weeks after Transformation "Now it is ver...

To the Manor Bound Ch. 04

by Nikki258 on Sep 26, 2017
Transsexuals & Crossdressers

This probably won't make too much sense unless you've read the other chapters first. Like the other chapters this includes forced feminisation, BDSM, and non-con, so it might not be your cup of tea. Regardless, do comment and email me to let me know what you think, or just to say hello! ***** Chapter 4 - Five Weeks After Transformation Peter held the d...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

The Dominatrix Order Pt. 02 Ch. 01 - Sissies

by Jwwsmith on Jan 22, 2019
Transgender & Crossdressers

THE DOMINATRIX ORDER: FEMDOM EROTICA 2 BOUND BY LAWS BY J.W. SMITH *** "All Women Are Created Equal" was inscribed on the bronze plated plaque on display in Representative Johanna Aletheia's office. It was the declaration put forth by The Founding Mothers of Femininus, of which Johanna's ancestor belonged to. Johanna was of the oldest lineage of Feminin...