Gay Crossdressing Halloween Stories

300 results
Orientation
Length
Source
Infinite Scroll

Behind the Scenes Ch. 03

by rightside27 on Nov 18, 2019
Gay Male

Connor's POV: 'Hey stranger, how are you holding up today?' Leo teased in his mock-Southern accent. I love it when he does that, it makes him sound like a sexy cowboy. 'I'm good, and you?' I smiled, he didn't have to know about the stuff with Caytlin. I didn't want to bother him with that, and I didn't want to think about it now that I could see him again....

Chris Donaldson Ch. 04

by tazemebro on Sep 15, 2017
Gay Male

Chapters 1, 2 and 3 tell the story of Chris and Justin, roommates in their sophomore year in college. Justin is an athletic frat boy with lots of animal charm, and quickly turns the sexually inexperienced Chris into his live-in submissive. Justin's volatile and violent personality, however, eventually frighten Chris into asking his Resident Advisor for new q...

Seduction, Submission and Surrender

by yukonnights on Sep 15, 2017
Gay Male

This is the story of another time. The Vietnam war was tearing the country apart and young people were beginning to throw off the outdated rules of a society. The year was 1969 and the place was Boulder Colorado where two young men met and embraced their homosexuality. It is also a story of dominance and submission and the myriad emotions these roles bring f...

Bobby and the Cop

by robcub32 on Sep 25, 2017
Gay Male

Time seems to go by so quickly. It was almost a year that I moved out of my mom and step-dad's house, but it seemed like just yesterday. After graduating from college, I returned home to the Detroit suburbs. I got a job fairly quickly as a computer tech. The company I worked for sold PCs and custom software to small and medium-sized businesses. I did diagno...

Turning Myself Gay Pt. 03

by bart_allen on May 29, 2018
Gay Male

To my mutual humiliation and arousal, the next morning at work, Marie could instantly tell. Truth was, I could see why: Nathan had fucked me three god damn times, and I my ass was sore as hell. Sure, he'd been tender as well at times, but one look at me and she knew. She just rolled her eyes at me, causing me to blush. She wanted to know what he looked like,...

Ben Loves a Challenge Ch. 08

by PDreadful on Dec 9, 2019
Gay Male

**I promise this isn't the end, there's more Dean and Ben to come. I hope you enjoy. -Penny** What he'd felt after Laura left him felt shallow in comparison to the pain-coated emptiness inside him now. Nothing mattered anymore, Dean's cold dismissal broke something in him. Worst part was that he couldn't figure out where he'd gone wrong. Dean didn't call,...

Longing for Change

by Maria24 on Dec 12, 2018
Gay Male

1. John woke up, his mind flooded with mad desires and lust—still influenced by the wet dream that had spoiled his boxers. He took a long, cold shower while coffee brewed. However, the plentiful stream of hot water failed to wash away the strong, bizarre sensations that had tortured his mind for months. He poured himself a steaming cup of coffee and lit a...

Unmasked and Exposed

by LaRascasse on Aug 18, 2017
Gay Male

Hey there fellow Litsters! This is my first (and probably last) attempt at Gay Male. The inception of the story happened when a female author friend of mine (who adores this category) placed a bet with me that a straight guy (namely me) cannot write a Gay story. Here is my attempt at proving her wrong. I look forward to your comments and feedback here. It...

Juan Gets Mace(d)

by DavidPatrick on Sep 14, 2017
Gay Male

This is a follow up to "Lightning In A Bottle." If you have not read "LIAB," then you may want to seek it out for context before reading "Juan Gets Maced." ***** Chapter One As the new guy bent over the water fountain, the first things I noticed were his legs and his ass. His legs were muscled and covered with fine, blonde hair, and his ass cheeks were di...

Bittersweet Irish Cream Ch. 03

by Kabba118 on Mar 16, 2020
Gay Male

If you missed part 1 and 2 of Bittersweet Irish Cream, please go back and read it to get the full story of how these two ended up here. To those that have been waiting for this moment, I hope it satisfies you! I would love to hear your thoughts on Jack and Ethan at this moment so please comment, vote and thanks for the love so far! ~~~~~ Jack had never act...