First Sissygasm Stories Reddit Stories

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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...

First Multiple Sissygasm Today

by JessC on Sep 16, 2017
Transsexuals & Crossdressers

I had my very first multiple sissygasm. I own a fucking machine. It has been the source of much pleasure since I bought it. I decided recently to try for a really great sissygasm. For those of you that don't know, a sissygasm is having an orgasm with a soft cock from ass/prostate stimulation. Well, I decided that I was going to prep myself to have a nice la...

A Date with Destiny

by StarrOftheNite on Aug 20, 2018
Transsexuals & Crossdressers

Most people like to have a mind's eye picture of what the narrator of a first person story looks like, and since this is a true autobiographical story about my personal quest for gender identification, sexual orientation and self-realization, it's probably important to the narrative, too. Physically, then and now, I'm almost six feet tall, broad shoulders, n...

Simone

by Sissyhalo1 on May 11, 2020
Transgender & Crossdressers

I'm so sick and tired of my life. It was like I'm cursed. I wasn't a great looking guy in high school with bad skin and bad grades because well... I was poor. My old man was a night watchman and mom was a stay at home mom because she was poor and had no real education past junior high when she started popping us out. So everything was tight and for the m...

Sissy Pills Pt. 02

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

There's nothing like waking up like this. This being after being fucked. Not fucked but riding a dildo until you have a sissygasm. And yet that's not the first thing in my brain waking up. It's the cum. It's that eating my own cum. And really feeling this need sort of burned in my brain from the semen and the pills. I really, really want to suck a co...

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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Cockland Island Pt. 06

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

I woke up and I was sucking that realistic dildo cock like a soother and it was so weird and right and made me smile as I pulled it out trying to make my lips do the pop you can do sometimes with suckers. I giggled and did it a few more times then pumped it in and out of my mouth trying to get that dick lips feeling going on. That's a sexy sissy trick, all...

Stranded But Not Alone 💕

by LushinLace on Oct 13, 2020
Audio

My naughty mind very rarely cums up with sweet stories. I just get too dirty too fast, 😜😈 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. 💕 After a plane crash, a young woman is stranded on a desert isl...

White Boi Learns his Place Ch. 06

by sissyashley4bbc on Oct 31, 2018
Transgender & Crossdressers

Sunday arrived and vacation was over. As I sat in the backseat of the Jeep with Daddy, I could help but think of how much had changed. 4 days ago I was a straight guy on the mend from a breakup just looking to start fresh by getting fucked up with some new friends. While that definitely happened, so much more did too. I was completely seduced by Daddy and...

Family Business

by fantaseeboy on Jul 27, 2020
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** Laying on my bed in my room in my mom's trailer, my laptop was set on the table beside me with my webcam aimed where I lay. White, satin, bikini panties were looped around my left ankle. The snug-fitting, stretchy crop top clung to my narrow, smooth chest and left my midriff bare....