Gay Halloween Stories

239 results
Orientation
Length
Source
Infinite Scroll

Fawned - A PetPlay Romance Ch. 04

by WinterPior on Mar 2, 2020
Gay Male

The next time they saw each other, they did not have sex. Barnaby didn't even know he'd be seeing Gil. It hadn't been a very good day, so he wasn't particularly In The Mood to start with. Hadn't so much as texted his 'friend' (Were they friends?). Gil didn't need to hear about the potted plants he dropped in front of his entire class because he didn't stop...

Cops Get a Treat

by buckeye on Aug 18, 2017
Gay Male

It all started a few years ago when a friend of mine invited me to a Halloween party. I couldn't think of what outfit I was going to wear until one night when me and a few good friends found ourselves in Hooter's. I couldn't help but think that my friends would have one hell of a laugh if I showed up looking like one of the Hooters girls. I went up to the co...

No Solicitors Allowed... Well

by lovetoshowit on Jul 31, 2019
Gay Male

It was a Tuesday and when I got home I found that my wife was going to be gone for a little while. As was my habit when she was gone I slipped into sompanites and a short strapless sun dress, with a set of 4" heels. I loved to walk around like this, and in our neighborhood, it was not unusual for people to be going door to door to try and sell different thin...

Dick - The Teen Gym Stud Ch. 06

by dominanceaddict1 on Nov 18, 2019
Gay Male

After our run in the park, I didn't hear from Ryan for almost two weeks. We had walked out of the park together with Dick's arm around my waist. He had tucked his hand into the back pocket of my opposite cheek. The pocket wasn't meant to be functional, of course, the pants being as tight as they were. So Dick's large hand was clearly outline as he pinched...

Backstage Romance Ch. 01

by ikhneumon on Sep 13, 2017
Gay Male

* Daniel * Everyone knew Jeffrey Williams, of course. A local boy made good, he had gone in a ridiculously short time from community productions to Broadway to a long-running television series. He even had a few better-than-average movies to his credit, though none in a leading role. Not that Jeffrey couldn't have carried the mantle of a leading man—he had...

Halloween Hike

by WRJames on Aug 18, 2017
Gay Male

"Do you believe in ghosts?" It was not the sort of question my wife normally asked. I'm the romantic type. She's a numbers person, a bean counter. "I don't know. Why do you ask?" "Well, we're hiking up to a ghost town, aren't we?" "It's not that sort of ghost town" "It was a thriving village once." A voice broke in behind us. One of the guys walking alon...

Member of the Club: Morning

by hasnoalias on Aug 18, 2017
Gay Male

I awoke in the morning to find I was still in the same position, Bruce was still spooning me from behind. I saw sunlight coming through the blinds and realized we must have slept for the rest of the night. I smirked as I felt Bruce's cock was hard with morning wood. I slowly disentangled myself, so as not to wake him up...yet. I lowered my head to his cock a...

Dick - The Teen Gym Stud Ch. 07

by dominanceaddict1 on Dec 9, 2019
Gay Male

"What's your idea Ryan?" I asked, looking over at him. I was supposed to be the responsible adult escort for Ryan and a friend to go to his school dance. But earlier that night I had been dressed up in a costume—by Ryan's older sister—as a lady bumblebee, complete with giant tits, a short dress, thigh-high stockings and heels. Ryan's had then essentially u...

The Day After

by ifiknewthen on Dec 24, 2019
Gay Male

This is the continuation of Horny on Halloween. Ryan finally loses the dress and while it's no longer Halloween, he's still getting tricks and treats. ***** The Day After: Ryan's Walk of Shame I stirred awake to find myself on a couch. My head hurt and at first, I didn't remember where I was or how I got there. I had woken up to what was officially Novem...

Pauletta Defends His Title

by Boxlicker101 on Aug 30, 2017
Gay Male

This is my entry in the Literotica Halloween Contest. I'm late getting it in, so I will quickly need a lot of votes, hopefully high votes, to win any prize. * The city of San Francisco is almost certainly home to the most beautiful drag queens in the world, and every Halloween there is a competition to determine who is the fairest of them all. Paul Porter...