Sissy Anal Chastity Stories

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My Husband, My Slave

by SubbyHubby27 on Sep 19, 2017
Fetish

My name is Candice, I am 26 years old, and I am writing and sharing this story because my darling husband, Ricky, is too shy to do so. It all started in 2010. We were on a trip with another young couple our age. My husband's best friend Trey and his girlfriend at the time, Amber, whom he is now married to, were quite the partiers. Drinking, smoking, and...

Sissy Slave

by mikedoreilly1973 on Nov 24, 2018
Fetish

It was late friday night, and Mike had just gotten home from work, he was tired and filthy from work and decided to take a much needed shower, he went to the bathroom and noticed the door was slightly ajar, he peeked inside and saw his 18 year old daughter Samantha taking a shower. Samantha was his daughter from his previous marriage which had ended badly wh...

My Sissy Cuckold Life

by SissyCuckMike on Jan 2, 2021
Fetish

Hello everyone, my name is Mike and i am now a sissy cuckold. If you don't know what a sissy or a cuckold is i will explain, a sissy is like a cross-dresser but usually dresses up in pink frilly women's clothing and cuckolding is similar to a hotwifing where she goes out on dates and fucks other men without her husband/boyfriend around but with cuckolding it...

Sissy Prince: Origin Ch. 02

by SatinSlip on Feb 6, 2018
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** "I'm sorry about this." Jentif whispers in the Elf's ear. Larallin gives a slight nod. The big red woman was actually quite nice, and the wife of his new friend Oliver. But, like the rest of the slaves, she would do anything their monstrous master ordered. The ginger, Elf man...

Sissy School

by zeta515 on Jun 19, 2018
Novels and Novellas

Copyright 2018 by Zeta All rights reserved This story may be freely distributed in electronic form but must include this copyright. Sissy School is a work for pure fiction and all locales, names, characters, places, and incidents are the products of the author's imagination. Any resemblance to actual events, locales, or living persons is entirely coincide...

Sissy and Missy

by ChristopherDB on Feb 12, 2019
BDSM

Copyright 2019 Christopher D.B. * The central vacuum system made barely a sound as I made my way through the apartment. It was spacious and occupied the entire third floor. Although fully furnished and containing some of Countess Tori's personal items, she only stayed here a few nights a week. My feet were hurting, as the toe box on my pumps fit a little...

The Chastity Trap Ch. 02

by slavemalcom on Mar 13, 2018
BDSM

Malcom rushed back through town to his house, all he wanted to do was get to his room and see what could be done about the chastity device trapping his cock. As soon as he opened the door however, Emma came rushing out of her room and looked down from the top of the stairs. "Lott...Oh it's you." She said. She didn't even try to hide the disappointment and d...

Teased, Denied and Sissified Ch. 04

by subbieman on Sep 12, 2017
Fetish

Quick Recap It had been nearly two weeks since Ashley caught me trying on her panties and I was now wearing a fresh new pair every day along with a bra as she encouraged me to find my "inner-sissy" and explore my fetish. I had also learned that she obtained more pleasure from her toys than my cock and, as part of this "exploration," she had decided it was b...

Transforming Brent Pt. 05

by sissymissyct on Dec 2, 2019
Fetish

I awoke early, partially due to the pressure of morning wood in the chastity. Once I settled down, I showered and slipped on a robe and quietly made my way to the kitchen. I quickly familiarized myself with the layout and, finding what I needed, started cooking a nice breakfast for my mistresses and myself. Ham and cheese omelet, OJ, toast and sausage, along...

The Business Trip

by OOAA on May 11, 2020
Fetish

My wife and I had been married for about 3 years when I first developed an interest in enforced male chastity. I had always had a very kinky and active fantasy life to fuel my almost daily masturbation habit. I was a 22-year-old virgin when I met Irene and I was looking to resolve that problem. Irene seemed like an exciting 20-year-old girl and I thought tha...