Sissy Maid Chastity Stories

25,197 results
Orientation
Length
Source
Infinite Scroll

An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...

French Lessons

by lipsticked on Sep 13, 2017
Fetish

I first saw the ad on the internet. The website was a listing of Dominant Women on the West Coast. Since I live in Los Angeles, I was checking out the pictures and information on local dominants. The one that caught my attention was unique. Madame Darcy was based in Paris. Her ad stated that she traveled to Los Angeles frequently and had family here. She re...

Getting Nailed

by jbirdman on Sep 25, 2017
Fetish

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), cross-dressing (CD), mild bondage, Trangender (TG) and a few other fantasies of mine. I hope you find it entertaining, but if you might be offended, stop reading and do something e...

A Morning's Service Ch. 02

by Philippasubmaid on Dec 10, 2017
Transsexuals & Crossdressers

This story is a graphic tale of a Dom and his very submissive crossdresser. If you are offended by tales of BDSM and sex between consenting adults then read no further... other wise enjoy. Feel free to leave honest comments or suggestions, it really does encourage those of us who write to continue... ***** As I laid on the floor I strained to hear what m...

Feminizing First Step Ch. 03

by antares34 on Oct 21, 2019
Transgender & Crossdressers

(All characters are age 18+) *** I felt like I was losing control. My body and mind were becoming less and less masculine with every passing day. And I was secretly ENJOYING it. I couldn't help myself. Every time I looked in the mirror, I found myself loving the ever-changing reflection. First, my dyed pixie haircut. Then, my bikinis. Then, my nose, ear, a...

Flowers in Her Hair Ch. 15-16

by NSEW1 on Mar 11, 2019
Fetish

Alpha Male Linda made her request as she moved towards the bed, "Brad, I want nothing more than to be fucked rough and deep by the Alpha male in this room." She looked coyly at her lover, using her finger to beckon him. Linda didn't care that he was all sweaty from the gym. "Come here and fuck me now." Brad looked condescendingly at Victor, taunting him, "...

My Teasing Hotwife Ch. 04

by footslave85 on Mar 25, 2019
Fetish

Part four -- the evening out I look down and see a small dainty gold chain with a little item hanging off it. I wince as I see that it's not the key to my chastity cage but a symbol, the ace of spades, which signifies her status as a hot wife who enjoys the company of black men while her husband is caged in chastity. She can barely hide the giggle from her...

My Teasing Hotwife Ch. 05

by footslave85 on Mar 26, 2019
Fetish

Part five - watching the fun I had just finished getting everything ready when I heard a car pull up outside and I quickly rushed back to the living room to wait for the new lovers to arrive. I just made it back into the room as the front door opened and they walked in holding hands. I saw my wife was a little tipsy and had a big smile on her face and I cou...

The Live-in Maid Ch. 02

by Quietoldie on Jan 31, 2018
Transsexuals & Crossdressers

I think that everyone has deja vu every once in a while. Well when Barbara Kane walked through the front door of the shoe shop I had this strange feeling that I'd met her somewhere before. She has a commanding presence. Quite apart from her beauty there is something else about her. She's tall, but it's not just that, there's an air of confidence about her to...

The Pantysissy Diaries Ch. 03

by JPantyboyVSL on Apr 23, 2019
Transgender & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapters 1 and 2 before reading chapter 3. ***** It was nighttime in NYC, and Jaymie and her 6 Mistresses had just left their apartment to head to Vic...