Maid Chastity Stories

20,460 results
Orientation
Length
Source
Infinite Scroll

Chastity

by wishfulthinking on Sep 18, 2017
Romance

Kinlee was a curious minx that courted mischief. Her father, having caught her at a tender age curiously fondling the unspeakable parts of a handsome if dull guard, had sought to protect the value of his property. Thus, Kinlee had found herself swiftly burdened with a gold chastity belt and her budding sensuality curtailed. To a point. For the golden belt cl...

Lady Connie Ch. 01

by Snowkemper on Sep 25, 2017
BDSM

Author's note-I've submitted two series of stories to this site, and both have been dark, violent and frankly pretty unpleasant. I wanted to write a BDSM story with people that were happy, content with their roles and getting what they wanted. This is the result. Feedback, votes and comments are always greatly appreciated-even negatives! ***** JIM closed h...

Innocence Lost Ch. 30

by bradley_stoke on Sep 14, 2017
Novels and Novellas

In Which Kedi rediscovers Innocence by choice, Chastity by circumstances, and meets Honore who is herself reunited with Innocence. Kedi knew that Innocence was soon due to arrive to spend a few days with her, but she wasn't exactly sure when she'd arrive. She had been quite surprised to hear from her, although they'd kept in touch all the months since they'...

Maid for Cum

by slcmalemaid on Aug 18, 2017
Fetish

The first thing one notices is the spent condom. This would normally be a very odd thing on a kitchen counter. However, I am not only not surprised, but I expect it. Next to the condom is a list of cleaning chores. And there I am, alone in a slutty french maids uniform getting ready to clean the house. How did this turn of events happen? Well, one night, a...

First Time Cuckold Ch. 05

by Angelscuck on Sep 14, 2017
Fetish

Oscar started sucking my well fucked pussy with great zeal, licking up all the cum that Jordi had deposited. Jordi's cock was so big and thick that it had left me quite sore and Oscar's attentions were both soothing and stimulating. After about an hour and four orgasms, I reached the conclusion that I really enjoyed being sucked to being fucked. Oscar looke...

Laura Love Ch. 07

by Long2bLocked on Jun 26, 2019
BDSM

Note to readers: This series is a continuation of "Laura's Femdom Empowerment". You should read that series before this one. ***** Chapter 7 Female Led Destiny The next day was Monday. I couldn't wait to see Bodhi at work. I took one of his chastity keys out of the safe in my bedroom closet. I put it on the same silver necklace I was wearing in his domina...

A Sissy Maid's Tale Ch. 01

by Erotictales4u on Sep 19, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy in the femdom niche, it is focused on male submissive humiliation and has a Sissy theme running through it. Is set in an imaginary future. ***** The cool air licking at my almost bare ass cheeks enhanced the feeling of nakedness, but I wasn't naked. In fact, it would have been...

March Madness Ch. 03

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

Sissy Maid to Be... Ch. 02

by missjennymaid on Sep 10, 2018
Transsexuals & Crossdressers

I would recommend reading Chapter 1 to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jeremy is get...

My Story of Degradation Ch. 03

by Philippasubmaid on Sep 10, 2018
Transsexuals & Crossdressers

This story involves BDSM and crossdressing, change of lifestyle and full submission both mentally and physically. If this is not for you feel free to read elsewhere, please. ***** "Yes." Was all I replied. I saw her nod to Cindy and felt Cindy behind me and the cold steel of the handcuffs go back on my wrists, Cindy shut them, and I heard the ratchets go...