Reddit Chastity Stories Stories

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Cuckold trial

by Crazywriter on Apr 29, 2025

As I scrolled through my phone watching cuck porn I saw an ad Do you want to be cucked ? Are you worried about the consequences? Do not worry as you'll get to experience a baggage free cuckolding experience, choose your appropriate cuckold package I was curious and clicked on it after browsing about the website on Google and reddit and confirming it is legit...

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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 thatโ€™s probably not the best option, if you know how to change that please leave it in the comments|| Intro: Alex Whiteโ€™s mother, Jennifer, died when Alex was 15. But before that, she married an awful man, Dave, who Alex absolutely despised. H...

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Sammi Starts Camming

by Sissy_Sammi_ on Dec 3, 2017
Transsexuals & Crossdressers

Sam had always been rather small and feminine. As a guy puberty seemed to have missed him which left him in the rather uncomfortable position of being very girly. He was only about 5'8" with a womanly rounded face, smaller waist, and slightly larger hips. He had brunette hair, which for a guy was on the longer end. His lightly tanned white skin pieced with...

Changes

by Slave2dbg8422 on Jun 4, 2019
BDSM

Changes Chapter 1 After being locked into the micro-sized chastity device for an incredibly long 37 days of teasing torture and denial, I had become more and more submissive to her with each passing day. I was waiting for her to make the trip to come live with me, after a very long, long distance relationship. We've both been switches throughout our relati...

Long Road Pt. 01 - First Steps from Vanilla

by Henriette7 on Mar 17, 2020
BDSM

Another boring day in the office. It has been seven and a half hours and finally, my coworkers are leaving. I still have an hour to go, but the office is mine. Wasting no time, I switch the tabs in my browser and open up the innocently sounding pages filled with hardcore BDSM. Oh reddit, my dear friend - where would I be without you. Ever since the tumblr s...

Qazzar's Shorts

by Qazzar123 on Apr 29, 2025

This page will serve as a place for me to put any one-off stories I write. I hope to write stories with lots of thematic range, and will put tags alongside the titles to give readers an idea before selecting anything. I am also posting these stories on my Reddit account with username 'Qazzar123Stories'.What's next? Plastic Trinkets [Cuck...

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Stranded But Not Alone ๐Ÿ’•

by LushinLace on Oct 13, 2020
Audio

My naughty mind very rarely cums up with sweet stories. I just get too dirty too fast, ๐Ÿ˜œ๐Ÿ˜ˆ But when I read this sweet (but definitely sexy AF) script written by reddit user u/DPP_NewFrost I couldn't wait to fill it. It's a long slow build with a bit of a "Blue Lagoon" vibe, which I loved. ๐Ÿ’• After a plane crash, a young woman is stranded on a desert isl...

Your friendly neighbourhood sex shop

by asian8335 on Apr 29, 2025

You were surprised that you got a job in a sex shop, considering you have no retail experience at all. But you were broke and couldn't be picky who hired you. You're an employee of a sex shop in a quiet neighbourhood, the only one actually. You never met the owner, only spoken with her over the phone. "Open whenever you like, just keep the customers hap...

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One Shots

by JakeSnakeCakes on Apr 22, 2025

This is a short collection of stories and chapters that are too brief to be expanded into their own CHYOAs. For me, it's a way to get rid of my excess stories and ideas the way users on this site get rid of their excess fluids. I think one of the best things I can do creatively, is allow myself the time in order to express myself. I'll also be responding to...

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Caught in the Act

by taodie on Oct 6, 2020
Transgender & Crossdressers

As you sit watching TV while your wife gets ready for a girls night out, you are not able to pay attention as you just feel your penis strain against the chastity cage. You had been looking forward to this night all week knowing you would have it to yourself. It was during these rare moments where you could fulfill your girly desires you had never dared shar...