Gay Crossdressing Halloween Stories

300 results
Orientation
Length
Source
Infinite Scroll

Charlie

by Dennis_St_John on Aug 30, 2017
Gay Male

I froze in shock, not wanting to believe what I was seeing. This had to be some sort of sick stupid joke my best friend was playing on me. I pulled my eyes away from his chest and looked him in the eyes, seeing tears and shame on his face. Anger surged through me like a bolt of lightning, feeling betrayed and a little stupid. I couldn't help myself, I sa...

Exploring my Sexuality Ch. 03

by alexis19901 on Jul 6, 2020
Gay Male

I could have put this story in a number of categories but it consists a lot of gay sex so that's why I've picked it. It does contain some elements of taboo, group sex, crossdressing and gay sex. The other chapters do provide some of the back story. After my last meeting with Mark, I went back to my normal life. Going to work, college and seeing my girlfrie...

The Lure of Cock from the Closet

by jakladd on Oct 15, 2017
Gay Male

It's true. We desire cock. Our wives have no idea what goes on inside of us with this desire to submit...to cock. We hide it from everyone but in our minds it's a runaway train. To touch, feel, pull on, sniff, rub our faces in it, lick it, taste it, suck cock. We've done it before, maybe a short time or a long time ago. The specter of guilt and shame dampens...

The Yule Log

by artisticbiguy on Sep 25, 2017
Gay Male

I sighed as I saw the signs for Morrisville. My home town, the place I had struggled to escape over fifteen years ago; now I was coming back with my head hung low and my tail between my legs. It was humbling and humiliating. I had left when I was eighteen and never looked back. I wanted a career, I wanted a life, and I wanted love. I'd gotten the career, I'd...

Avery's Desire Pt. 11

by Chancem77 on Feb 13, 2018
Gay Male

"This is fucking bullshit!" Mikey wadded up the newspaper and threw it across the room. "They shouldn't even have been allowed to enter. Having Cole Rhoads as part of the band is a fucking joke. This is supposed to be for amateur bands, not seasoned musicians." "Dude, take a chill pill." Kassidy Lane, the pirate from the Halloween party, was stretched out a...

Cupid's Sophomore Year, Semester 01

by xaviermayne on Sep 25, 2017
Gay Male

This story involves acts of both sex and romance between consenting adult males, so if that's not allowed where you live then you should march in the streets. I'm releasing this story under Creative Commons by-sa-nc license, which means you can do pretty much whatever you want with it, as long as you give me credit and don't use it for commercial purposes of...

North Star Ch. 03

by rem1324 on Apr 24, 2018
Gay Male

All characters are 18 years or older. I appreciate your feedback in the comments. Thank you for reading my story. ***** The realization upon awakening that I was not alone in bed brought with it the weight of more than the left leg, arm, and head laying on top of me. This other weight was a force beyond the basic gravity of his mass. It was the paral...

Clark's Story Ch. 02

by robcub32 on Sep 25, 2017
Gay Male

Ch. 2: College Boy I had a hard time adjusting to college. My roommate had other friends and I didn't click with anyone in the dorm or in my classes. It was about three weeks in when I broke down. I called Gordie on his cell phone and I broke down and cried. I told him how much I missed home, my parents... and him. I told him how awful it was, how I didn't...

Unexpected Ch. 11

by BNDMTL on Sep 25, 2017
Gay Male

It's the day before Thanksgiving; Alex has gone to pick up all our happy helpers. While he is gone I'm sitting at the table trying to organize his Christmas present. I am getting him new hockey gear and bag. His current gear is from when Jesus lost his skates and falling apart. He refuses to part with any of it. "These are ok for another season." He says all...

Sex, Drugs, and Princeton Ch. 02

by phineas2014 on Sep 14, 2017
Gay Male

Author's Note: This is chapter 2 in an ongoing story about the characters Brett & Travis during their first year at college. More to come soon! * A few weeks had passed since that night when Brett and Travis had jerked off together, er...separately, in the same bed, different bunk. They'd never talked about it. It was as if the alarm clock going off zappe...