Gay Crossdressing Halloween Stories

300 results
Orientation
Length
Source
Infinite Scroll

Gustaf's Castle

by sr71plt on Aug 18, 2017
Gay Male

"Oh, come on, Rob. Come with me," Josh had said. "What's the worst that could happen? You could get laid. So what? It's about time. We've never been to a gay bar before—at least I haven't. And I hear Gustaf's is a gas. All made up in Transylvania style and everything. It's Halloween. They're sure to have pulled out all the stops for the occasion." No, I'd n...

A Night at the Movie turned me Gay Pt. 02

by jamtby on Oct 12, 2020
Gay Male

Entering the room immediately caused my stomach to churn with excitement. Something about entering a place where strangers are in control and you anticipate being involved with sexual activities. The what, why, and how remained a mystery. This only added to the combination of nervousness and excitement. The woman with a strangely deep voice said, "Welcome...

Blood and Love Ch. 05-06

by Eternalivan on Sep 25, 2017
Gay Male

Chapter 5 ************* Daniel's Story I – Yes and No *************************** As I walked out of the Geller residence into the cold night I sensed a presence. My body stiffened, senses alert as I walked down the stony path leading towards the gate. My eyes were fixed ahead but my sharp ears were waiting for an impending movement while my olfactory pe...

So You Want to Be in Movies

by sr71plt on Aug 30, 2017
Gay Male

"So, my agent said it was for some sort of commercials for the Halloween season." "Yes, that's right. It's for commercial use to be released a few weeks before Halloween, yes." I needed the work. The plays on Broadway were shutting down almost as fast as they opened. It was just bad luck, a bunch of new plays that weren't piquing the audience's interest an...

Horsing Around

by grgy56 on Nov 18, 2019
Gay Male

As a cast member of the off-off-off-Broadway comedy play about a girl and her horse, of course I was included in the upcoming Halloween party. It was to be held next week the on Monday before the 31st. It's an off day since almost no one goes to see any show then. On the other days, there was a pretty good sized audience so the run was extended for another m...

The Wingman

by noodneighbor on Aug 18, 2017
Gay Male

My roommate, Kent, was the best wingman I ever had. He was a good looking blonde to my brunette and even though I was in good shape at six foot and 185 pounds, he had a few inches on me with my same weight. Every female I knew asked me about him and I would have been jealous if he weren’t so gracious and such a cool guy. The thing is when he answered my ad f...

Prove It

by Gentleman44 on Sep 14, 2017
Gay Male

As I walked through the goodwill searching in vain for the green turtleneck that would really put my Steve Bartman costume over the top, I thought back over the past few months. Having moved to a new city and started working at a job that I, at first, thought was beneath me, things were starting to look up. They say that you can get through anything if you h...

Hallowiener Pt. 01

by forummj on Jun 5, 2018
Gay Male

"We could dress as girls!?" He was actually smiling at me. Smiling at me across the dinner table in our packed out college cafeteria. He was actually pleased with his suggestion. What the hell was he thinking? "Hey I'm up for that if you two are!" John chirped in rather too enthusiastically for my liking. It was always the same, October would be rolling b...

Four Friends

by KeithD on Aug 18, 2017
Gay Male

"No, I think you should go ahead, take the trip, and do the article on your great-grandfather's winery, Edward. It will probably do you good to get out of New York for a few days." Dr. Peterson and Edward Cordona had finished with the consultation and had risen from their seats to go to the door of Peterson's consulting room. "But the hallucinations—what i...

Easy Access

by Apolo1 on Aug 18, 2017
Gay Male

To say that I was in heat by the time my boyfriend Benny and I headed out for a Halloween party is an understatement, to say the least. What's worse, he knew that I was hornier than a proverbial toad, but for reasons that would only later become clear to me, he decided to make me hold off on getting some nookie. The aforementioned party was an annual shindi...