Chastity Plug Stories

24,707 results
Orientation
Length
Source
Infinite Scroll

First Time Sissy - The Bike Path

by Phillysissylexi on Jun 15, 2020
Transgender & Crossdressers

My roommates had gone away on a trip for a week, so I had the house to myself for a few days. I had been waiting for a moment like this. As soon as they left I went to my closet to find all my girly clothes, toys, makeup, heels, and lingerie. I couldn't contain myself. I was so excited to turn myself into a sissy. I turned on some sissy hypno to listen to wh...

The Office Boy Ch. 03

by Aussie Worm on Sep 25, 2017
BDSM

In the previous episode slaves Samantha and Steven both earned 3 months locked away in chastity for sharing a bed. However Steven earned another 3 months for running away from home for the day. Katrina who was beginning to like her slave invited Steven to her bedroom for the night, although he had to sleep on the floor. --- "Steven wake up." Katrina said...

Slave Immigrant Ch. 30

by OldGuy1026 on Sep 14, 2017
Sci-Fi & Fantasy

After receiving a cloned body I was immigrated 127 Light Years from Earth to Free Skyes. Unfortunately I had to work and pay for that cloned body and I had very few skills a high tech society could use. So it was either I become an Unskilled Labourer or a Sex Slave. In the end I guess Human Recourses had figured me out correctly. All those years in BDSM chat...

Almost Damsel Almost in Distress

by shawnavinyltv on Jun 19, 2018
Transsexuals & Crossdressers

Finally! I had the day off from work and I planned to spend it indulging two of my favorite activities... crossdressing and self-bondage! I've been dressing since I was 10 years old, and about the only thing that was more exciting than getting all femmed up... was locking myself into some strict bondage and struggling to get free! I lived in a small apartme...

Lowest of the Low

by bracemaiden on Aug 31, 2017
Fetish

Chapter 1 – Moving in - Sunday, November 13th My name is Patricia Teresa McKlellan, but my friends call me "PT". I was going through a dark time in my life. I had gotten fired from yet another dead-end job a few months ago. My self-confidence and enthusiasm were buried in a grave in the deep recesses of my psyche. The one bright spot in my life was serving...

End Scene

by felicia_rene on Sep 28, 2020
Transgender & Crossdressers

This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy Description: When a rich wife discovers that her husband married her for her money and to add insult he turned out to be gay. ROLL CAMERA My rich wife had me over a barrel after finding out about my affair with my handsome boy toy assistant. She took a...

The Hot Tub

by nameshavebeenchanged on Sep 17, 2017
BDSM

Master got a new hot tub to share with slave. He had it heating all day. Slave got wine and candles to make the night romantic. She set everything up while master was at work. Knowing when he gets home, she showered and shaved just before that so she would be nice and fresh and smooth for master. She put her hair in pigtails, just like master likes it. She p...

Nocturnal Anal Stimulation. A Study

by suppleWriter on Sep 17, 2017
Fetish

Note: this is a story, fiction. None of the facts are correct, and all the names are false, invented. So enjoy! (Re-posted with the above clarification, and links deleted). Nocturnal Anal Stimulation in Orgasm-Denial Relationships - A Study NOCTURNAL ANAL STIMULATION IN ORGASM-DENIAL RELATIONSHIPS. A STUDY BY: Willsoin,D.E., Arangji,T.F - UCNYCE - Dept...

Halloween Pool Party Pt. 03

by sissymissyct on Sep 15, 2017
Fetish

I soon headed to town and told the apt manager that I was sorry but I would have to move out immediately. It was a family emergency and I would be leaving the area the next day. I asked if he knew anyone that would purchase my furniture, appliances and household stuff, and he asked to see it. It was all quality furniture and he said he would take it and offe...

Everything Has a Price Ch. 13

by MALIBUMAN666 on Sep 16, 2017
BDSM

The challenging option... I ......................................... (hereafter referred to as 'slave'), agree this day ....../ ...... / ................. to be bound by the terms of this agreement as laid out below, for a period of one year. 1. Slave's cock will be completely under the control of Mistress at ALL times. 2. Slave will wear a chastity de...