Gay Halloween Stories

239 results
Orientation
Length
Source
Infinite Scroll

Halloween Kink

by toddstop on Aug 18, 2017
Gay Male

"Hurry up, babe, we have to get going," Jared called through the door. I had to grit my teeth and tear my eyes away from the mirror to answer with, "Just a minute." The matching costumes had seemed like such a good idea when I came up with the concept. Now, staring at my reflection, I wasn't so sure. Too late now, I told myself. It was our first Halloween p...

DJ Pt. 09

by o2byoung on Dec 17, 2017
Gay Male

I frequently refer to the boys in this story, the boys I refer to are DJ, Jamie, or Matt, they are all age 19 or more. At my age (76) anyone under 25 is a boy! DJ Part IX Sunday morning it was raining when I woke up about 8:30, not at all surprised that the boys were still sleeping. I made coffee, and was on my second cup when my phone rang, it was Jamie's...

Horny on Halloween Pt. 03

by ifiknewthen on Sep 25, 2017
Gay Male

Quick Summary of the Previous Chapters: Ryan really gets into the role that his dress is creating and finds that the quickie he had in the car with Graham didn't quite satiate him for the night. Balancing between the roles of eye candy and tease, Ryan has Travis and Chase in the palm of his hands... or maybe it's the other way around. Will the sexual tensi...

Unknown Love Ch. 01

by lessthanperfect on Sep 14, 2017
Gay Male

Cigarette butts lay scattered on the ground as the aroma of cheap cologne and wildflowers wafts through the air. Typical, nothing day on a community college campus. The newness hasn't worn off yet. Everyone is still walking around with that wistful air of happiness. It's enough to make man puke. Give it a week or two; they'll be bitching soon enough. This i...

T Was a Bopper

by endthedream on Aug 18, 2017
Gay Male

T Was a Bopper-A Real Show Stopper (for Dreamshell, who asked me to continue the world of T a bit longer) * A real show stopper, me, and what a rattyworld, but ace was there for me together with Sin and Trinity and we got to getting some prayer life on, for here is the adorable me, with out adolescent pimples finally at long last. Rotting world needing bl...

Not So Boring Afternoon Ch. 03

by agpatch2 on Aug 30, 2017
Gay Male

Quick recap: my first gay sex was getting gangbanged in an adult bookstore during spring break. My second time was a one on one with a guy I met through a glory hole the day I got back up to school. Here's the thing... So I'd been curious about sucking dick and getting fucked for a while and when I finally did it (and loved it) I went to the extreme. I ende...

Buddy

by MVP6 on Jul 15, 2020
Gay Male

This is my sixth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side. Maybe not my best but it has an important message. In my first letter "Costume in a Costume" I describe how I dressed as woman in a Halloween costume to trick unsuspecting men into letting me give them my fir...

Playdate

by NattySoltesz on Jul 3, 2018
Gay Male

Naptime. The girls were asleep downstairs. Allen and I, in a lazy state from a lunch of chicken nuggets and french fries (the girls' choice), were sprawled out next to each other on the couch, yawning and gazing at the TV. Just another rainy Sunday afternoon playdate. Allen and I had been doing this for the past two months, giving ourselves a chance at a mo...

Halloween Treat

by MWMottawa on Sep 1, 2017
Gay Male

It was 1987. I was married to my first wife and living in a small town in the south of Alberta. My wife and I had been invited to a costume party at my brothers’ house in Calgary. As much as we would know nobody at the party other than Ron my wife was anxious to go so we agreed. She had decided to dress as Vampirella and I went as the bearded lady from the c...

Blood and Love Ch. 11

by Eternalivan on Sep 25, 2017
Gay Male

Chapter 11—Halloween blues ******************************** Sean's Story VII -- Separated ********************************* I stood transfixed, unsettled and unnerved by what he had just spoken. His words were still ringing in my ears as the realization of the reality of the situation came crashing down upon me. I stumbled backwards for support. I could...