Black Maid Stories

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Orientation
Length
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Infinite Scroll

Emilia

by Cavalliere on Sep 17, 2017
BDSM

It was early evening, but still the darkness closed in, the fog swirling oppressively round the street corner. The carriage slowed, and halted outside a terrace of substantial houses. The door swung open, letting in the cold air. Emilia shivered, hunching her shoulders together under her cloak. Her companion, an older woman, perhaps thirty, leant over and wh...

Molly The Maid Boy

by Otaku_Apologist on Sep 14, 2017
Transsexuals & Crossdressers

The frustrated sigh of his master was signal enough. Lying on the bed, his fine silk pants unwrapped, the young master was clearly in need of a helping hand. In the corner of the dark room, the bare-chested maid boy had waited all night to fulfill his duty. His black lace skirt was wrinkled, the fabric stiff like a ballet dancer's. The skirt's style was in h...

From a Husband to a Dutiful Sissy Ch. 04

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

A quick note about this chapter. It runs a tad long as I want it to really set things up for Chantel's future, not just some sissy maid for her now Mistress wife, as cool as that can be, but to develop a more varied sissy, crossdressing, maid and slut story. I hope it works for my readers. ***** Chapter Four: Moving on to reinforcing my new lifestyle Satu...

From a Husband to a Dutiful Sissy Ch. 05

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Five: I'm going to be more than just a sissy maid. Waking up Sunday morning, I sit in my bed and think about my slut duties last night at the rest area. I get into the shower and it all floods back to me as I shower, then dry off, moisturize and get back to my maids quarters and do my makeup, put on my bra, panty and maids outfit, black one today wi...

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

Recruiting of a Sissy Maid Ch. 11

by Sissy_Chantel on Nov 23, 2017
Transsexuals & Crossdressers

Chapter Eleven: People Moving into New Roles and More. Chantel has made her way back to her club dorm room, enjoying the corrective measures of being a Domme over Biff and Marty. She is certain they will be much more mature and even though they still hold powers over the sissy girls like all other male minder/staff, they will better respect what these sissy...

Dionaea

by _ourladytamara on Dec 2, 2019
Erotic Horror

The wheels of Eliza's skateboard clicked as they rolled over each gap in the sidewalk. A cool wind gently blew down the streets in stark contrast to the heat that bore down upon the entire city; it wicked the sweat from her brow and flowed through her tank top as she coasted down the hillside streets. It was a lazy Tuesday - though, so far as Eliza was conce...

Cassandra and the Cave Ch. 02

by MJKnight on Jan 29, 2020
Group Sex

Cassandra sat down and rested her back against the cave wall. She looked around the room and tried to clean the cum from her lips and her breasts as best she could. The salty taste still filled her mouth so she swallowed again. The guard was unshackling the slave beside her and the man standing behind Ophia was already waiting obediently to be led out of...

Recruiting of a Sissy Maid Ch. 03

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Three: Training Done, Chantel is On Her Way. Waking up back in her cell, Chantel finds that her days being trained, orientated and broken off will here with the Burrows brothers are wrapping up. Mitch enters her cell and has her come back out and back into the house with him and Nate. Mitch says, "Well Chantel, time has come for us to part our ways...

From a Husband to a Dutiful Sissy Ch. 03

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Three: My sissy maid lifestyle becomes more set in reality. Morning comes and I carry on my new sissy morning ways, shower, shave, makeup and dress up in my maids dress, this morning a pink satin one over pink pantyhose and pink patent 5 inch spike heel pumps. I dutifully prepare breakfast for my Mistress Helen and get a bowl plain porridge for myse...