I Think I Want To Smash A Sissy Reddit Stories

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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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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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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...

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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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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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...

Crossing The Line

by groundhogsarethebest on Aug 21, 2018
Transsexuals & Crossdressers

Before last night I could still pretend that it was the idea that attracted me. Claim that it was the tabooness of the act that attracted me, not the fact that I was dressing up in girl clothes and fantasizing about being used by a group of men. Last night it became real. I'd posted ads on craigslist before, hit up grindr, the whole shebang, but dudes wo...

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...

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 New York Tale Pt. 05

by neuromancerzero on Aug 26, 2019
Fetish

I woke up early the next day, despite us staying up late. The warmth of all five of us on a queen bed was too much for me. I was thoroughly entangled by limbs and I had to carefully extricate myself as so note to wake them. After five minutes of untangling notes, I was able to discretely slide into the shower and rinse myself off of the potpourri of bodily f...