Sissygasm Stories

121 results
Orientation
Length
Source
Infinite Scroll

A Sissy's Halloween

by Evangeline_E on Oct 29, 2018
Transgender & Crossdressers

Disclaimer/authors not: All characters in this story are over the age of eighteen. This is my first story so criticism is wanted as long as its constructive. I make these stories based on what I want and my own sexual fantasies. Thank you 😊 . * To tell this story right I need to start at the very beginning, the time where I first started to question my se...

Awakening My Inner Trixie Ch. 01

by Sissyhalo on May 29, 2018
Transsexuals & Crossdressers

All characters are over 18+ years old. *** I was as stunned as everyone else was when Kiki came into the comic shop. Oh sure we had girls come in but we never had a girl as gorgeous as Kiki come into the shop and she was tall and had the most stylish red hair just kissed with blonde that tumbled down in these long waves and she was in this tiny little dre...

Femboy Caught in Locker Room

by Femboy_Anna on Sep 11, 2018
Transsexuals & Crossdressers

Hello everyone and this is the first part in possibly a series I will upload. The characters in the story are of the age of 18. I collaborated with another person in making this story in a discord server. The story is done as it was typed and sent however I will be editing small parts for such things as spelling errors. The story will be back and forth. Begi...

Covid 19 - Pete Turned into Charleigh Pt. 02

by His_fag_wife on Jul 13, 2020
Transgender & Crossdressers

Again it was as though she'd slapped him back into reality, just as she intended, she'd noted his angry response earlier that day and wanted to trigger him again, but trigger him much more this time. She simply would not accept rudeness or attitude from him. Pete had to realize that as Charleigh took over his psyche, that she would need to be more and more s...

Sammi Gets Adventurous

by Sissy_Sammi_ on Dec 3, 2017
Transsexuals & Crossdressers

Sammi has been doing cam shows and posting photos online for a few months now. She's gotten into a steady rhythm with it, and loving every second of it. She has never felt so alive as when she's fully dressed up and putting on a show for some perverts online. And the money that she brings in from her shows certainly doesn't hurt either. Over the time she's...

How I Became a Sissy for BBC

by Caged4goddessd on Mar 12, 2019
Transgender & Crossdressers

It really all started in college. I was a fairly typical and somewhat popular guy. I was involved in a few different clubs and a member of a popular fraternity on campus. Of course, this led to me knowing quite a few of my classmates and at the time I had my share of success with the females in my classes. It was my junior year and at the time I was dating...

The Molly Virus Ch. 05

by Sissyhalo on Mar 12, 2018
Transsexuals & Crossdressers

*Before... I kiss him leaning down and shoving his legs up with me as I fold him in half and fuck him over and over as we kiss then it happens. There's this inside resistance that stops as the brain and body reconciles getting fucked and relaxes and lets it happen. There's this sweet sigh of surrender that comes out as I bottom out inside of him and then h...

Re-tooled

by Sissyhalo on Mar 13, 2018
Transsexuals & Crossdressers

Re-tool your life. Re-tool yourself. Sick of not getting what you should? Sick to fucking hell of all these assholes getting with hot people they really don't deserve? Sick to hell of Liberals and Feminists making impossible to jump through hoops so that only the privileged people get to be happy? Sick of being a goddamned incel? Look we all know that...

Descent into Submission Ch. 04

by Cyanlot on Mar 26, 2018
BDSM

Chapter 4: End of the Day Rewards When I got home, Charly was already there. Normally, she'd be in kitchen starting on dinner. We usually cooked together, but whoever got home first started. Tonight wasn't a normal night, though. Charly was in the living room, with a glass of wine in her hand. "What are you cooking me for dinner tonight, Honey?" she said a...

The Secret of the Island Pt. 04

by neoview on Oct 30, 2018
Sci-Fi & Fantasy

You thought the story had died but it was just my lazy ass refusing to continue. Also I was busy with my girlfriend so I couldn't really focus. Yes, I have a girlfriend now. Well "she" prefers to be called a girl even if she isn't. Without her I would finish this story much faster, but... she gave me some interesting ideas which were too good to ignore. ***...