Gay Sissies Stories

124 results
Orientation
Length
Source
Infinite Scroll

Cowboys Don't Kiss

by KenJames on Sep 14, 2017
Gay Male

I was in the Automotive section of K-Mart, scanning the stack of air filters for the right part number, when I noticed him. He was about thirty-five, dressed in a cowboy hat and boots, with an expensive western shirt and blue jeans. His body was slender but strongly muscled. His eyes were shadowed by his hat brim, but I could see he had a bushy moustache. He...

Guys' Retreat Pt. 05

by Cyanlot on Apr 21, 2020
Gay Male

Part 5: Brianna's Training "Vince had a terrific idea, Brianna," Kent said. "It's really going to make this easier for you." "Yeah," I said, noncommittally, knowing full well that whatever Vince had come up with wasn't going to be to my benefit, though I was sure it would benefit them. "Yeah. We've been downloading some videos for you to watch. You're goi...

30-Days of House Arrest Ch. 02

by bjmichaels on Dec 4, 2017
Gay Male

It was hard to concentrate on washing the breakfast dishes and cleaning the kitchen. Mister G was in one of his playful moods and couldn't seem to keep his hands off me. He massaged my shoulders and back and occasionally a hand would slip beneath the waistband of my shorts and claim possession of a buttock, squeezing and pinching it. Needless to say, I wou...

My Journey Continues

by corkscrewjohnny on Sep 14, 2017
Gay Male

Brad had left for college 2 weeks ago and I had settled into my job at a local restaurant. I worked in the kitchen preparing food for the cooks. It was a typical go nowhere boring dead end job but I needed the money. I became friends with a waiter named Jeff who seemed like an okay guy. We got along pretty well and after a while I confided in him my desire...

Chubby Sissy Meets His Daddy

by vulpinechub on Sep 19, 2017
Gay Male

The following story is a work of gay fiction. It contains sexual acts between males. This story focuses on: Humiliation, diapers, sissy play, domination. Copyright 2014 -- Feedback is appreciated. * My university decided to cancel classes for the day, but it was too late: I was stuck in the worst traffic of the decade. Mainly due to the incompetence of b...

Zeke in the Park Bathroom

by JimBob44 on Sep 14, 2017
Gay Male

*Author's Note: Any and all persons engaging in any sexual activities are at least eighteen years of age. Disclaimers: Yes, I need an editor. No, I do not want an editor. Yes, it jumps around too much, yes there's too many people to keep track of, yes it's too short, yes it's too long, yes this is stupid shit, and yes, I am a horrible writer. For those of...

You are a Sissy Pt. 02: Public

by Roland15Rollin on Dec 24, 2019
Gay Male

Welcome back, sissy. Welcome back, my little sissy bitch. We came so far in our first session. You came so far. You once thought you were a man but now you know better. You are not a man. You have never been a man. You are a sissy bitch. And that makes you so happy. So fulfilled. You love being a sissy bitch. A faggot. A gay little toy for real men to use...

Surprise!

by paladin1954 on Apr 3, 2018
Gay Male

It never occurred to me that I was doing anything wrong. I had always been a tease and I would continue to be until the day I died, but my good friend knelt at the edge of my bed, crying his eyes out and I felt really bad about it. I knew there really was nothing I could do to satisfy him. There were no options in my plan, but for some reason I felt pity. "...

How I Became a Sissy Pt. 03 - Final

by Yngwhiteboi on Jan 23, 2019
Gay Male

Abdul opens my door and I slip in, then swing my legs in. He closes the door. He gets in next to me and starts the car. As we back out the drive, I ask "Where are we going sir? I thought I wasn't allowed to remove my new collar? Did I displease you?" "I wasn't displeased but the collar is for home and special occasions, not for everyone. We are going to my...

Jack Hammer Ch. 01

by KenJames on Dec 12, 2018
Gay Male

Private investigator Jack Hammer smiled as he looked at the men gathered around the wrestling mat in Steel Steve's big main room. There were at least thirty of them. A couple were totally naked. The others were dressed in Speedos, jeans, or leather gear. Lots of leather gear. That was the main vibe at the converted gym on East Riverside Drive. The jockstrap...