Bondage Sissy Stories

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Orientation
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Appointment by Card Only Ch. 07

by Sputnik57 on Jul 1, 2019
BDSM

Bruce was now under no illusion as to the ruthless level of cruelty the woman who had claimed him as her own, and her feminine associates, would go to in order to sate their sexual lust for the domination of masculinity, and their pleased indifference at the fate of Miriam's husband at the cocktail party he now observed on his knees in a corner, further emph...

Making Francesca Ch. 03

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

As Frank lay there on the thin mattress, listening to Justin climb the stairs, he thought about all that had happened and what he feared was still to come. The dull ache in his ass told him that Mistress Celia was definitely not someone to trifle with. He also thought about the reaction his penis had shown to the various activities he had endured since arriv...

Home Alone: Day 02

by sissy_boy_stu on Sep 16, 2017
Transsexuals & Crossdressers

Day 02, The Mistress It was 12 o'clock in the office, I couldn't wait 5 whole hours before I got home so I decided to take the rest of the week off. After racing home I ripped my clothes off and dived straight into my sisters panty drawer and took out a pink matching g-string and bra with hearts on. The feeling of them on sent my cock rock hard so that it s...

Delving into Femdom Ch. 01

by readytokneel2907 on Jun 1, 2020
BDSM

**Chapter 1. Growing up Oh my where to begin, I imagine it is best to start at the beginning (or as close to it as I can remember). I grew up in a relatively medium sized east coast city living what some may call a normal life with two sisters and both my parents. Growing up I was always into sports and when I entered middle school I had begun to focus on b...

It's a Wonderful New Life

by alexyzia on Sep 16, 2017
Transsexuals & Crossdressers

I met Sherry at a bar. Imagine that. I often picked up women at bars. I'm a good looking man, have a nice sporty car, cash flows freely from my pockets - at the bar anyway. So I do OK at snagging a tipsy babe for a nights folly. But all of the sudden karma has caught up with me. When I hit on her she told me to back off or I'd be sorry. When I persisted, pol...

It Really Does Happen

by lipsticked on Sep 26, 2017
Fetish

This story is copyright 2009 by (lipsticked11). All rights reserved. No reposting without permission. * I am owned by a dominant couple and their niece and used as a live-in maid, cook, and sexual slave. My name was Michael, now I am Michelle. This is my story: When I was 35, my wife Connie and I lived next door to another married couple, Denise and Steve...

Poker Night

by grizzley123 on Sep 14, 2017
Fetish

We have the house ready. My chip set has been unpacked and stacks worth $50 are ready for the buy in. The men play dealer's choice from 7pm till 9:30 and then a Hold'em tournament or two often till late at night. Dinner is at 6pm. My wife has that ready. Since it is a cooler day in November she has made her delicious Massaman Curry with rice. There are other...

Covid 19 - Pete Turned into Charleigh Pt. 04

by His_fag_wife on Jul 27, 2020
Transgender & Crossdressers

Red unlocked the locks, unclasped the clasps on the box and then popped the lids back on the two bottles of poppers, but popped them in place for later. After this first session being so much of a hit, she thought Charleigh might be in the box for some time, every day for the coming weeks, if the lockdown remained in place for that long. At least then the du...

AliExpress and Sissy Downfall Pt. 06

by His_fag_wife on Mar 6, 2018
Transsexuals & Crossdressers

"Ok, now you've been fed, back in the chair and Candice will get your make up done, so that you are as pretty as you can be when you return to your Mistress and Master." "Get all that mess cleaned off her face please Candice and start making her up to look pretty." "Yes Miss Bell." Charlie got back in the chair and Candice prepared to make her look as pre...

Becoming a Sissy Maid & Slut Vol. 05

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Prefix: A continuation of my sissy maid and slut journey. I hope you all do enjoy my unfolding story here. I am writing further chapters with hopes to give you all a semblance of some of my sissy ideas and thoughts so that these may excite you as the reader. I will try hard to keep each chapter on an exciting flow of what I feel may be life of a full time si...