Gay Sissy Caught Stories

10,521 results
Orientation
Length
Source
Infinite Scroll

The Trucker Ch. 01

by Woody110 on Mar 16, 2020
Gay Male

I was running late by the time I walked to the gym on Thursday evening, and the place began to empty out as the clock hands swept towards its 10pm closing time. I decided to skip my shower rather than cut my workout short. By the time I was done the evening cleaners were moving through the building, carrying mops, buckets and the rest of their equipment. The...

Darren & Dean do Dale Ch. 02

by betamale08 on Aug 7, 2019
Gay Male

It was still dark when I was woken from my sleep, feeling Darren's movement in the bed. Spooning me now, my eyes opened groggily in the morning darkness but I could feel it there first touching my back then with his moving, I could feel it even more, moving into the cleft of my ass, just sitting there, resting, Darren's hard cock, I could feel it with him pr...

Cocklust Ch. 24

by briacon429 on Dec 10, 2018
Gay Male

It turns out making a good sex tape is harder than you'd think. The first things we ran into were nerves. As soon as the thought sank in, I started getting cold feet. After all, I knew how much could go wrong, having been a victim of revenge porn before. At the same time, I trusted Chad in a way I'd never trusted anyone. We both knew so much about each othe...

Roomie Issue Pt. 02

by Samhdjd on Jul 10, 2019
Gay Male

FRIDAY NIGHT Once my ride arrived, I gave the driver my exact address then I shoved my hookup guy roughly into the backseat before climbing into it myself. The car moved and I knew I'm about to have a fun night. Even more fun than I thought I would. He kind of leaned back against the door and he put on that oh-so-gorgeous smile that only made me want to ru...

The Nude on the Balcony

by KeithD on Jun 25, 2019
Gay Male

I knelt there on the artist's couch between Rafa's spread thighs, my hands gripping his knees—moving his knees out as I buried my cock in him and moving them together as I withdrew my cockhead almost to his opening, never, though, losing purchase inside him. The young Greek man, not more than nineteen by my reckoning and as handsome as Apollo, slitted his ey...

Sexual Secrets Ch. 04

by DickSwett on Sep 21, 2020
Gay Male

Inside the safety of a tiny dorm room on the campus of a small liberal arts college in central Maine, two freshmen boys were at it again. It was the night before Thanksgiving break, when everyone on campus would head home for a week of rest and relaxation before the frantic last push of the semester commenced, and Aidan Simmons and Logan Temple were in the m...

Dick - The Teen Gym Stud Ch. 08

by dominanceaddict1 on Dec 24, 2019
Gay Male

The pickup truck pulled to a stop. I was in the front seat of a Ryan's car, on my stomach laying across the wide bench front seat of the pickup truck. My ass was sticking in the air and the high schooler's strong hand was on it, squeezing. My head was in Ryan's lap, licking up and down on his massive, mostly-erect, teenage cock. At the moment, I was playi...

I Wanna Be Degraded Ch. 03

by 1077ad on Dec 25, 2019
Gay Male

Author's note: After a near-fatal hard-drive incident I was backing up some old files when I came across this. Somewhat to my surprise, this was abandoned in a nearly-finished state and then forgotten about. I mostly just had to spruce it up a little and give it an edit. I'm not sure that at this point, eight years (!) later, there's anyone looking for a con...

Phallus Hunger

by sethreptilian on Mar 31, 2020
Gay Male

Nemesis Horizon Project David Lazarian * © 2019 PROLOGUE The midnight moon was blaring over the small southwestern Ontario, Canadian town. the neighborhood bar was crowded beyond its capacity. No one noticed or even cared about the three men sitting in the dark corner. The taller of the three stood up. "You guys have been stalking me since I've left Mo...

Gangbang Party Ch. 05

by exodus_69xXx on Jul 6, 2020
Gay Male

Author's Note: Gets a little extreme, with pissing and extreme cum play involved towards the end. Thanks for reading. *** Saturday morning. What strange, lucid dreams I had. I opened my eyes and immediately groaned, disgusted by the nasty taste in my mouth. My head hurt and felt like it weighed a tonne. As I stumbled up, I felt a little sick... and insan...