Maid Chastity Stories

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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...

Sissy's Decline into a Slut Pt. 04

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Six: Chantel's Decline is Achieved, Owned by a Black Master as his Sissy Maid and Slut. I cannot believe at what is happening to me here. Master named Gage is about to purchase me and place me into slavery as his sissy maid and sissy slut. I am near in panic, I want to run away, get into my car and drive for the safety of my home. But I know this wi...

Sissy Maid to Be... Ch. 01

by missjennymaid on Sep 5, 2018
Transsexuals & Crossdressers

Prolog I have always had the desire to dress like a girl. It started at a young age when my mother used to have me try on dresses to "see if they would fit my cousin." As I got older I still had the desire and it got strong enough that I started going out in public in college. I was lucky enough to meet and marry a woman who was accepting of my "hobby". Liz...

Mistress Chronicles Ch. 03

by MistressMtoyou on Sep 25, 2017
Fetish

Title: Decision time Background/update Even if you've been following the last couple of stories about my subject, Muffin, you might want to read this background as there are a few new points of note. Muffin is slightly heavyset, 36 years old, about 5' 7" and 160 pounds. He is quite submissive and seems to be aroused by a number of fetishes, but he professe...

Lock And Key

by ksu328 on Sep 1, 2017
Fetish

As the first snow of the season started to fall on my small hometown, my sex life started to make a turn just like the seasons. Well, I guess since I've never really had a sex life besides jacking off my little pee-pee, you could say that my sexual freedom was changing. The little box (ironic that it came in such a small box) arrived on a Wednesday and as m...

Fantasy: His and Hers

by Storyhacker on Sep 25, 2017
Fetish

When Jim came home from playing golf, his wife Betty was waiting at the door. Jim knew something was wrong. "Follow me," was all she said. Jim followed the nicely shaped woman of thirty nine through the house. Betty wasn't model material but she was more than Jim had ever hoped to land. She had a nice figure, she was fun and treated Jim good. Jim knew Be...

My Live-In Slave

by Martin Young on May 1, 2006
BDSM

It was Friday night and I was having a great time. I had been dating Sandra for almost a month and she was truly the girl of my dreams. She was beautiful, funny, smart and every time I was near her my heart started beating like an angry carpenter with a hammer. That specific night I had taken Sandra out to a fancy restaurant. The food was excellent and we we...

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Donna's Ultra-High Heels Bk. 02 Ch. 12

by SHAFERLINE on Sep 15, 2017
Fetish

Author's Note Chapters 12 through 17 are the final chapters to "Donna's Ultra High Heels - Book 2" and will be sequentially submitted in both the Fetish and BDSM categories in the following order: Chapters 12, 14 and 17 in the Fetish category and chapters 13, 15, and 16 in the BDSM category. ***** Chapter 12 The elevator reached the first floor and Don...

My Life Ch. 01

by lesserMan on Sep 14, 2017
BDSM

I was alone in my room. I sat there thinking how this all began. ----------- After our wedding, I was carrying her across the threshold into the room. She was 5'3" and stunningly beautiful, with shoulder length brown hair and sparkling green eyes. We both undressed to consummate the marriage and she asked "Wouldn't it be fun if we tied you up?" It had al...

Sissy Maid to Be... Ch. 03

by missjennymaid on Apr 8, 2019
Transgender & Crossdressers

I would recommend reading the first chapters 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. Jere...