Gay Halloween Stories

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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...

Halloween Cruise: Night 01

by Bright_Star on Sep 1, 2017
Gay Male

I needed to get away for a few days, so I decided to book a cruise. I figured that would be a great way to escape the problems of the real world, and I would be able to relax for a fun-filled seven days and get to visit some great destinations and do some things that I hadn't been able to do before. And who knows, I figured, I might be able to meet someone n...

Halloween Filmfest Conversion

by sr71plt on Aug 18, 2017
Gay Male

The champion soccer player for the night, all decked out in his silks and his team-color knee-high socks, left his basement apartment in the old row house and strutted down St. Phillip and across Basin Street and North Rampart, into New Orleans' French Quarter. He held his head high, his chest out, his tight butt tucked in, and his basket thrusting out in fr...

Halloween Revisited

by sack on Aug 18, 2017
Gay Male

David felt a heaviness in the air as he hurried toward the hidden wine cellar. The sky had turned inky black and a few stray raindrops stung his face in the overcast gloom. It was Halloween, and night was swiftly falling. David had taken his strongest flashlight, complete with new batteries to cut through even the pitch black hiding place he had recently dis...

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...

Halloween Job

by timtrack on Aug 18, 2017
Gay Male

Throughout college I took several opportunities to work what could best be described as seasonal jobs to give me some extra spending money. So at the beginning of the school year, I'd work at some of the last festivals of summer, Oktoberfest, then Halloween and usually some extended work for the holiday season. It sometimes paid cash but always allowed for m...

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...

Halloween Rabbit Holes

by hornyyoungboylovesolder on Jan 15, 2019
Gay Male

I had seen some men, one man many times, and was having a lot of fun. The one guy I was seeing constantly was 58 a bit of a belly, but an amazing cock. After a bit he had gotten me into cross dressing. It started with panties. Then stockings and heels. Leading to bras, skirts, and wigs. Eventually I was putting on make up, eye lashes, lipstick, the whole nin...

Halloween Party Hollow Weenies

by walterio on Nov 4, 2019
Gay Male

INVITATION Sitting across from Archibald Thompson, the private school's Headmaster, was Stanley Morrison, the school's largest benefactor. Stanley was having a Halloween costume party for his special clients. He needed five students to attend the party. "So, Stan, you are asking me to send five gay students to your home for a Halloween party." "That is c...

A Halloween Carol

by RubenR on Oct 24, 2018
Gay Male

This is my contribution to the 2018 HALLOWEEN CONTEST. It is not a sex story. For those looking for detailed descriptions of strong, muscled bodies, or hot, steamy sex scenes, try the next one on the list; you won't find it here. As always I like to know how the story is received. Comments are very much appreciated (even critical ones; insulting ones not so...