Gay Crossdressing Halloween Stories

300 results
Orientation
Length
Source
Infinite Scroll

Miles's Revealing Clothing Teases

by sweetcobs84 on Oct 9, 2018
Gay Male

Disclaimer -- Miles and I, as well as the other students involved in this story, were all 18 years old and seniors in high school at the time the event described below took place. * Miles and I grew up together. We lived within about 5 blocks of each other; went to the same elementary school, and our moms took turns carpooling us to/from school. We also hu...

Salt's Quest for Charisma

by JasonClearwater on Oct 15, 2017
Gay Male

Salt Lucius Ulysses Tennery hated his mother, and for many and various reasons—not just because her dark sense of humour had made his teenage years a living hell. Her vexacious naming of him so traumatised him that, at thirteen, he retreated from reality entirely, gavaunting about the place with a cast of imaginary friends (he was certain 'gavaunt' was a wo...

Midnight Masquerade

by Xathandra on Aug 18, 2017
Gay Male

Getting out of his car, Mark turned to look at his sister, Katie, shaking his head. Once more she had talked him into another crazy idea and he couldn't quite figure out how she'd done it. Ever since they had been young children, his twin had the uncanny ability to bat her eyes at him and get him to do her biding. He contemplated getting back into his car an...

A Natural 'Gurl'

by sexyR2 on Aug 18, 2017
Gay Male

Yes, I know that it has been a few years since I last posted. I was busy. I hope, however, that this new story makes up for the delay. It is in a new category for me, gay male instead of gay female like two of my previous submissions. Enjoy! Debbie, er, sexyR2... ***** Today... When the somewhat urgent knocking came to the door, Debbie knew in an inst...

Fawned - A PetPlay Romance Ch. 09

by WinterPior on Mar 30, 2020
Gay Male

Mornings with Gil typically went like this: First, well, Gil's alarm would go off, and Barnaby would wake up with the sinking realization that he'd fallen asleep on top of him again. He'd be apologizing before the man was completely coherent, so the first thing to come out of Gil's mouth would be "It's fine", "Don't worry about it", or "How did you sleep?"...

Billie's Sore Ass

by erectus123 on Jan 13, 2018
Gay Male

Billie's Sore Ass: Sexual Fraternity Hazing [Readers, be assured all events take place between men who are 18 and older. There are no minors or Appalachian miners depicted here. Most are college guys who range from 18 to 32 years old. A few older men do appear towards the end of the story to add a mature balance. All characters in this story are based on re...

From Straight to Gay Submission

by silkstockingslover on Sep 25, 2017
Gay Male

Summary: A straight engaged college guy becomes a submissive cocksucker to a dominant black man. Note: This is a story based (remotely true) on a request from a fan. It is my first attempt at writing gay male fiction. The story is a little extreme, so if that offends you please stop reading now. If it doesn't, I hope you enjoy. Note 2: Of course, all part...

Thirsty Old Men

by TheReluctantKnight on Sep 14, 2017
Gay Male

A word to the wise: This is a work of complete fiction. Never happened in real life. Also, I debated long and hard before posting this one as to where to post it. Finally, I settled on "Gay Male" because it is about gay men. HOWEVER, you should know that this almost landed in "NonConsent/Reluctance". I don't condone rape. This is a fantasy about a young (str...

Football Match

by Robert_Furlong on Oct 15, 2017
Gay Male

The start of the 'Butt Monkey' series of stories by Robert Furlong === Considering the impact it was to have on my life, it now seems difficult to believe that it came with no warning. But then, I suppose that's true of almost all of life's most momentous events: they emerge unannounced amidst the most boringly ordinary of our daily routines. === The day...

The Reluctant Heterosexual

by GhostHunterDude on Aug 18, 2017
Gay Male

Authors Note: I wanted a writing challenge. So I picked the genre I was most unlikely to write a story for. This an experiment to see if I could put my mind into a character that I would most likely never become. Most of my stories are based on my experiences, this one is based mostly on my imagination. I hope if you're into gay stories that you enjoy it. If...