Sissy Maid Chastity Stories

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Miss A's New Play Thing Pt. 04

by Pornenthusiest on Mar 2, 2020
BDSM

Recap: Miss A had just finished a luxurious bubble bath and was returning to her slave who was chastised and gagged with her pantie hose and a ball gag, with Miss A's wetted panties draped over his nose. Locked away in her dungeon, after an arduous breath control play session, her slave was spread wide at the ankles with a spreader bar, bent at the waist wi...

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...

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...

Sissy Chantel, New Reality Ch. 06

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Six: On My Way to My New Life at The Agency. Well the day has come for my transition in my life to becoming another sissy maid and sissy slut (aka: comfort girl) to 'The Agency'. Over the last two hard and humiliating weeks Master Camron and Sir Gage now as paid agents to my joining the team at 'The Agency' have helped me sell, give away or toss o...

Trixie's Chastity 01

by trixie47cd on Sep 19, 2017
Transsexuals & Crossdressers

Part 2: Trixie learns his new role. Since my wife came home early and caught me masturbating in women's frilly lace 2 month ago, so much has changed. She has taken control of my life since I begged her not to spread the story and pictures of my humiliation around town. After I made the choice of submitting to her feminization training, there really was no...

Sissy Chantel, New Reality Ch. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eleven: Sunday Fun Well now that our Masters and Mistresses have left us here in the locker room, with all twelve of us sissies now freed from our chastity, our sissy dicks are getting quite hard. We have been allowed a period of sissy sexual freedom. For the next 45 or so minutes we are to engage in a sissy orgy to relieve our pent up sexual desire...

Becoming a Sissy Maid & Slut Vol. 06

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Twelve: Chantel's day off. Ohhh, and ahhh as I awake and stretch in my bed. Mmm a blissful sleep where I see the clock and that it's actually 10:00am. At first I freak out a little bit as it normally would be very late for me. But I soon realize Master has allowed me a blissful and free Sunday off. I then get out of bed, my butthole is sore from the...

Her Male Wife

by Zippeduptight on Nov 6, 2018
Transgender & Crossdressers

Sometimes I wonder how I got into this mess. The answer is obvious but it usually comes during the day when I pee. Carla's orders are to sit when I pee. I lift up my skirt, and tuck the exposed chastity device down, and relieve myself. Just like now. The shiny pink pvc sissy maid outfit she bought for me is locked on at the neck. I stand up and flush walking...

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...

Samantha Meets a Dom Master

by SamanthaSatine on Sep 16, 2017
Transsexuals & Crossdressers

A true story - I am the main character and all the various activities described were undertaken with my consent...no harm came to me in any way... ***** The date was fixed. The room was booked – neither of the willing parties could accommodate, a not unusual event in the world these two inhabited from time to time. The morning of their meet had now arriv...