Sissy Maid Chastity Stories

25,197 results
Orientation
Length
Source
Infinite Scroll

How it began

by Thehypest1 on Apr 15, 2019
Fetish

You wake up after a long night of drinks with Casey. You hear the jarring sound of the alarm echo in your head. You think to yourself 'How much did I drink last night.' Your head is pounding and you lay in bed for a bit before heading to the kitchen to get water. You run into Allyson there. She made breakfast, she really is too kind. "Good morning, slee...

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Always Read Before You Sign Ch. 02

by Reaver90 on Apr 6, 2020
Transgender & Crossdressers

Sam stood outside Miss Turner's front door. The weekend was hell was for him. He couldn't sleep, he had to sit down on the toilet and pee like a girl and more importantly, he couldn't jack off. The young man feared what the beautiful woman but deadly woman had in store for him. He took a heavy breath and knocked on the door. He waited for a few seconds as t...

Chaste (A One Week Chronicles Story)

by Louise69 on Sep 16, 2017
Transsexuals & Crossdressers

This is probably the darkest of the One Week Chronicles story - Part 2 certainly is! - but I enjoy trying to find new ways to write and explore characters. I'll be very interested to know your thoughts on this one as it's probably the furthest from me, but was still huge fun to explore. As ever, it slots perfectly into the timeline and happens before the v...

Mamma Mia - En Femme

by ppeaks42 on Sep 16, 2017
Transsexuals & Crossdressers

"Ah chico, I think you already know the answer. It's making you into exactly the lover I want," Mia said as she brought a hand over to rub her cuddling stepson's chest. "It's making you into a woman like me." All the changes he'd experienced over the past weeks suddenly clicked in Tommy's head. The swelling and tenderness in his chest. The slight widening o...

Caitlin and Mistress Vicky Ch. 02

by Jemina004 on Sep 19, 2017
Transsexuals & Crossdressers

I hummed softly as I put the finishing touches on the salmon. Teriyaki salmon was my wife's favorite dish and it filled me with pride to know that I was making her happy. My mouth watered slightly as I arranged the tray. (I would only be having a salad myself, as I had to maintain my figure.) Taking out a pocket mirror from my apron, I checked myself to ma...

Bdsm adventures

by Sgtwolf on Dec 7, 2017
BDSM

This story is for a compilation of many different bdsm adventures. It was formerly known as latex adventures, but as chapters developed they dealt more and more with different aspects of bdsm, and less consistently with latex. Latex still exists as a strong element in many of the chapters, namely because I like to write about characters wearing it. I created...

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How to Become a Sissy/Cuckold

by Quietoldie on Sep 14, 2017
How To

This is a How To Guide for Sissies and Cuckolds. Please do not read this guide if you have no interest in the cuckold/sissy lifestyle. Like most couples these days both partners will be doing demanding full time jobs. Traditionally husbands have done gardening, cleaning the car, putting out the trash, performing do it yourself jobs around the house, drivi...

Virtual maze

by Sgtwolf on Dec 20, 2019
BDSM

It’s finally here! You scrimped and saved, and the most hyped technological breakthrough in years is finally yours! You open the package and pull out the black spandex full body suit, almost midnight in color except for the neon blue thick line running down the body and each limb. The Virtual Integrated Suit System, or VISS, claimed to be able to perfectly r...

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Becoming a Sissy Maid & Slut Vol. 08

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Fourteen: Chantel Learns a Lesson. Another bright and early morning for me. Another busy day ahead as a sissy maid and later on as a slut. What plans Master has for me as a sissy slut tonight, I don't know, but I'm sure it will be exciting, with lots of creamy cum for me to taste and swallow as well as good for hard core butt fucking. I'm already ge...

Trixie's Chastity 03

by trixie47cd on Sep 19, 2017
Transsexuals & Crossdressers

By the time I pulled my car into our driveway, most of the semen coating me from head to toe had dried to a flaking crusty shell. I stuck to the driver's seat as I climbed out on wobbly legs. The sun was just coming up and I hurried to get inside the house before any neighbors saw me like this. I started a pot of coffee, put the gallon jug of sperm in the f...