Reddit Sissy Chastity Stories

282 results
Orientation
Length
Category
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Infinite Scroll

Paul's Birthday Gift: My Wife's IUD

by donaldelliott11 on Jun 1, 2020
Group Sex

[The idea for Paul came from a Reddit post. The author, who has since deleted his account, gave his approval for me to expand, elaborate, develop, and publish this story as my own.] ***Our First Bull*** I'd wanted this for so long: a hard young teenage dick for my wife. She laughed about it, didn't take me seriously. Called it my "frat-cock fantasy," or my...

A week of

by Sissysub on Apr 29, 2025

||Reminder to make your nickname a feminine version of your name, sorry I made the default Faggella, I was horny but that’s probably not the best option, if you know how to change that please leave it in the comments|| Intro: Alex White’s mother, Jennifer, died when Alex was 15. But before that, she married an awful man, Dave, who Alex absolutely despised. H...

My Teacher is Blackmailing Me

by Yelawolf on Apr 29, 2025

(Everyone is 18 year old or older) I stare at myself, my body mask in a sexy schoolgirl skirt. The plaid coloring is the typical kind, a regular red and black. The white blouse matches exceptionally well. I fasten the cute small black tie around my neck. I'm John, kicking off my senior year of high school. I recently turned eighteen years old as fall began t...

Long Road Pt. 02 - Self-care

by Henriette7 on Mar 30, 2020
BDSM

It has been two days since my first real play-session with my girlfriend. And oh my, was it two very long days since then. My hope that living my fantasy would reduce my horniness and leave me free to think about other stuff was absolutely crushed. I couldn't stop thinking about it, about her. About her thighs, the change of her tone when she commanded me, t...

X-Change

by Noah_Peal on May 15, 2015
Miscellaneous

Pills Pink pills change males to females. Blue pills change females to males. Purple pills (X-Trans) change males or females into transgenders, can be combined with pink or blue. X-Change (Formula subject to change) Acquired from unlicensed "street" vendors. Changed (defective/in testing) formula. Cheapest. High pregnancy risk. Can lead to mental a...

Anonymous

by KingBandor on Sep 11, 2018
Loving Wives

George stared at the glowing computer screen from the depths of his dimly-lit "man cave", as he called it. In reality, it was the basement of his mother's house, where he spent most of his spare time. It was very cave-like, being dark, damp and smelling of moldy things growing. There was little that would be considered manly about it. It had a furnace in on...

VooDoo Doll

by OathkeeperPath on Apr 22, 2025

The sun was setting over the horizon, painting the schoolyard in hues of orange and pink. Graduation caps littered the ground, reminders of the euphoria that had swept through the air just hours earlier. Amidst the abandoned caps, there was a lingering sense of farewell, a mixture of excitement and melancholy. In this bittersweet setting, you found yourself...

Turned into a Slut Ch. 01

by xaitonnar22 on Sep 19, 2017
BDSM

This is a repost/reedit of my story. The beginning hasn't really changed but I did add a fifth ending chapter. * My girlfriend and I have always been a little kinky. We liked to tie each other up every now and then. We both enjoyed it every time we did it. I didn't realize that it was only the start of something that would land me in the position I am in...

For Betterment of My Family Ch. 04

by jay_kumar on Sep 14, 2017
Loving Wives

Important; The Sub-Chapters IVa and IVb posted earlier are now merged with the parent Ch. IV. with Ch. 3c, which was posted earlier. The story is based on some true incidences ;nothing has been added or concealed unnecessarily. ----------------------------------- I had a clear view of greenhouse through the window and the split I had made in the synthe...

Ignore the Warning Label Pt. 07

by Lydra on Aug 24, 2020
BDSM

Author's Note: This is NOT the kind of Part 7 that is designed to stand alone. You will be very lost without having read the first six parts. This is also the final chapter of the series. Fair warning, it is a long one. Please remember that this story is set in 2018, which was the present back when I started writing it. As always, many thanks to EGRI, Ec...