Sissy Cuckold Reddit 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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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...

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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...

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...

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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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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...

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...

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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...

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Cuckold Hypno Assignment

by DivinaTellsAll on Jan 1, 2019
BDSM

My name is Divina. I serve Goddess K. and Madam Vega. I am on a journey to become their perfect sissy girl, and a cuckold slave to Goddess K (who is my wife). The following is a true story of an assignment given to me by Madame Vega, and carried out with Goddess K. Assignment: Watch cuckold hypnosis video pornography, with my chastity cage locked and and...

Lexi's Date

by Sissy_Sammi_ on Dec 24, 2017
Transsexuals & Crossdressers

As Lexi scrolled through the photos of lewd sissies, she felt her sissy cock press against its pink cage. She wiggled her butt against the chair to feel the plug that was in her. She felt the soft panties against her smoothly shaven bum, and smiled her pink lipstick covered smile. She checked the time, 1:23 AM, and decided that she needed to finish up and ge...