Gay Sissy Bitch Stories

5,483 results
Orientation
Length
Source
Infinite Scroll

The Exploits of Cockslut Kelly 05

by CSK on Aug 29, 2017
Gay Male

WARNING!! THIS IS A GAY MALE STORY, BUT IT IS ALSO AN EXTREME BDSM STORY AS WELL. THIS STORY COULD EASILY BE PLACED INTO ANY OF THE FOLLOWING CATEGORIES DUE TO THE CONTENT: GAY MALE, BDSM or FETISH. I HAVE REQUESTED THIS FOR THE GAY MALE SECTION, BUT IT MAY END UP IN THE BDSM SECTION OR ANY OF THE OTHERS IF THE EDITORS OF LITEROTICA DECIDE TO RE-CATEGO...

First Time Sissy Sub

by stevn on Aug 31, 2017
Gay Male

My first time was in a booth at an adult video store with an older guy. This is a work of fiction, but if it came true... Please email any comments to the contact on my profile, I would love to hear from you. I'll follow this up with part II. ***** I had placed an ad on Craigslist while on vacation alone in another town. It said: "Submissive sissy bottom...

Sissy Bottom Has a Nite Out

by lostsoul1974 on Sep 14, 2017
Gay Male

My wife had gone out of town on a weekend business trip, so I invited my Fuck-buddy Eric over for some fun. I met Eric a couple years ago when he passed me his business card through a Glory Hole after he had fucked my asshole raw. After I eventually called him, we hit it off and have been friends ever since. Of course, hot raunchy sex can really help cement...

On No He Didn't

by felicia_rene on Sep 21, 2020
Gay Male

Description This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy safely. Rick a tall well-built handsome entertainer catches the eye of his boss as he works at his night club. The man's lust consumes him and he conspires to twist him and make Rick his bottom. Despite the fact that Rick insists that he was a...

Converted to Gay

by bart_allen on Sep 14, 2017
Gay Male

This story is partly inspired by messages from fans, with slight adjustments. Thank you for reading. ***** I wanted to share with you one of my current projects. A twenty five year old male by the name of Eric. Nothing too special in the looks department, but not too shabby either. He was neither heavy or slim, perhaps a slight softness to him. His eyes we...

Ozark Bitch Pt. 02

by oskarwild on Sep 14, 2017
Gay Male

Caged It was a long night for Patti. He wasn't used to sleeping with someone and Zeke stayed snuggled against him all night with his arms wrapped possessively around his new slave. Zeke snored and he mumbled in his sleep. Patti couldn't make out what he was mumbling, but occasionally "Patti" came through. Zeke dry-humped him a couple of times that night an...

Feminized by My Father

by YANKEE DAN on Aug 30, 2017
Gay Male

I opened my eyes, blinked, yawned, closed them again. I felt confused, disoriented in a way that was... strange. It wasn't like waking up was supposed to be, I wasn't half asleep. I can't remember getting in the bed, in fact I can't remember the last thing I remember. Where did consciousness end last? I was clueless. I tired to move my body and I found it...

Breaking In Pt. 02

by Iamkrazy4 on Dec 24, 2019
Gay Male

After laying on the ground for a few more minutes, I got up, grabbed my phone and headed to my bedroom. I quickly unlocked my phone and watched the video of what had just transpired. My dick immediately got hard, but instead of taking care of it, I slipped two fingers into my still lubed ass and fingered myself hard for the duration of the video. I spent a...

Drunk Friend to Sissy Slut

by olybiguy27 on Sep 14, 2017
Gay Male

What follows is the completely true story of the weekend that changed my life. This really happened to me and took place in the summer of 2008 just after graduating from high school. My name is Andrew and I was a major stoner in school. I had a lot of friends, mostly due to the fact I always had really great weed that I would get from my rich old neighbor...

Special Inducements

by bjmichaels on May 1, 2018
Gay Male

I was reluctant, but my ex-boyfriend Brian talked me into going to his younger brothers graduation pool party. We were sitting in my car in the parking lot of the liquor store. He had bought two kegs of beer and I helped load them in the car. "Why should I torture myself staring at all those eighteen year-old hard bodies?" I jokingly asked him. "Because yo...