Maid Chastity Stories

20,460 results
Orientation
Length
Source
Infinite Scroll

New Girl

by tiffanymanners on Sep 12, 2017
Transsexuals & Crossdressers

'Hey girl, watcha doin?' To this day, I don't know why I answered like I did. 'It's Jess!' 'Pleased to meet you, Jess! I love that show too! You actually look like Jess from that show 'New Girl'!' 'You're kidding me, right dude? I don't look at all like Jess, and that is not even my costume! For your information, I don't look like that actress, and furth...

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...

Mistress Monique

by bleedndkn on Sep 25, 2017
Fetish

I met Monique at a show. She wore a tight black dress, dark eyeshadow and was by far the hottest girl at the venue. I didn't have a chance. A mutual friend introduced us and I became immediately enraptured with her and in the days to come would constantly think about how to spend more time with her. Then, after an evening with Monique and mutual friends at...

Flowers in Her Hair Ch. 13 - Failed

by NSEW1 on Feb 11, 2019
Fetish

Failed Then came an unexpected knock on the door as Linda walked back in. She was with someone. Victor ducked into the guest suite to avoid being seen in his embarrassing maid uniform. But she called out for him, "Hi, honey, hey I've asked the cleaning crew to show you how to tidy up the room. Come here." Victor saw two cleaning ladies enter into the apartm...

Hotel Porter to Private Maid Ch. 02

by KinkyBiLad on Sep 12, 2017
Transsexuals & Crossdressers

Thank you for your comments and feedback about my first chapter in this series. I hope you enjoy this one just as much. Please leave comments and tell me what you think. Thanks KinkyBiLad "Next time I want you on your knees when I come up here" Matthew shouted, as he swung the paddle one more time on to Alexi's ass. Alexis couldn't do anything, her hand...

Help Wanted

by maidgirl on Dec 16, 2017
Transsexuals & Crossdressers

Brian found a table at the coffee shop, and sat down. This shop was his haven during the day. He had been applying for jobs since being laid off three months ago, and would use the shop's free internet. His savings were running out, and Brian was starting to feel desperate. "Order ready for Brian" the barista called out. Brian quickly grabbed his coffee. As...

Steamy Stories from Another World

by Fiftyfiftyfifty on Jan 17, 2021
Fantasy

Welcome to the fantasy world of Absoterra! It technically began with my story, "Erotic Dungeon Crawl," but didn't become a full blown world until my largest story, "A New World! Your Party of Hopeless Hotties". The more I wrote the latter, the more I wanted to flesh out the world, but there's only so much you can see when you read the sto...

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Erin Ch. 15: Perfect Sissy Cuckold

by Graves94 on Nov 16, 2020
Fetish

Erin Ch. 15: A Perfect Sissy Cuckold By Jonathan Quincy Graves {Note: This is the fifteenth in a multi-part story series cataloging the progressive evolution of a relationship between a dominant woman who provides leadership and discipline for her husband. Each installment can stand alone, but they read much better if you start at the beginning. Go to: Eri...

Girlfriend Turned Mistress

by gamerxbox41 on Jan 22, 2020
Fetish

Two years ago, was when my girlfriend and I started dating. She came from wealth, and was very smart, and turned that money into more. I didn't really see why she wanted me of all people, but love is love, I guess. I didn't have a job, never really did. Just went from fast food place to grocery store clerk, and never stayed at one too long. Which when you...

JoeBob, Submissive

by justincbenedict on Sep 17, 2017
BDSM

JoeBob waited with great nervousness at the table at Solozzo's Pizzeria. He wondered whether his date would show up. Would she be a beast? A lot of the women who were involved in the BDSM scene were just uggoes or fatties who were desperate for a man, why not a kinky one? That had been the problem with Elaine. She actually had had a pretty face, and nice bi...