Gay Crossdressing Halloween Stories

300 results
Orientation
Length
Source
Infinite Scroll

Gentlemen's Club Ch. 13

by Ywashere on Aug 30, 2017
Gay Male

This one's dedicated to Kevinmd1, who asked to hear more about this character. I fully acknowledge that I know nothing about the medical profession, other than what they show on TV - hope I didn't make too many blatant mistakes :-S Y All characters engaged in sexual activities are at least 18 years old. Mark Jeffreys' first love (never expressed and...

Tied to the Bed

by SluttyBisexualGuy on Dec 3, 2017
Gay Male

"Dude, I need your help, and it's gonna sound crazy, okay?" Caleb immediately said as he opened his front door to let his friend in. His best friend Adam has just arrived after receiving a frantic phone call from Caleb only twenty minutes earlier explaining that it was an absolute emergency and that he needed him to come over immediately. Caleb lived not...

Rory and Sebastian Ch. 12

by sebastiando on Sep 14, 2017
Gay Male

-- All characters are over the age of 18 -- Gaining my uncle, and my parents' permission, to go away for my first weekend alone with Rory was surprisingly easy. My uncle was close to our side of the family and he was Evan's godfather; he liked me and we played tennis together, every now and then. Rory had apparently had to work on his father's permission a...

King of the Strippers Ch. 01

by BothWorld on Aug 18, 2017
Gay Male

I was putting the finishing touches on a website I developed for a multi-national corporation. I had spent the last year of my life on it and was pretty proud of it. I sat back in my chair and thought about the last year. It started with my divorce. I married right out of college, which was too soon and lasted only two years. I was bummed about it in the b...

Under The Full Moon

by Pelaam on Sep 14, 2017
Gay Male

Stopping to adjust his bulky backpack, Ryder took a deep breath. The air was crisp and fresh, the day sunny and a pleasant temperature. He smiled as he took in the view around him. The forest was losing its leaves as autumn headed inexorably to winter. Over to his left, obscured temporarily, were the mountain ranges. As beautiful as they were, they were not...

Earning Danny Ch. 07

by EricMorrison on Sep 19, 2017
Gay Male

Hey guys! Sorry I've been absent for such a long time, but I was busy. First it was the end of the semester, then the holidays, then the beginning of the semester, and well, you get the picture, it's a vicious cycle. Anyway, I'd thought of just giving up on the story altogether, since I never have the time to write, but so many of you have commented and e-ma...

The Day After Ch. 05

by ifiknewthen on Dec 24, 2019
Gay Male

The crickets chirped noisily in the background as if they were trying to drown out the frogs that were croaking by the river. My ears seemed to remember where I was before the rest of me did. I opened my eyes to another morning hidden in the woods. My eyes quickly diverted from the greenery around me and back to my best friend that lay sleeping beneath me....

Fawned - A PetPlay Romance Ch. 07

by WinterPior on Mar 2, 2020
Gay Male

(Content Warning: the end of this chapter mentions self-harm scars) "Barney? Barn, slow down for a sec'- Hey-" The mug was pried from his hands, and Savannah continued making the latte, having to wipe caramel off from the sides. "Why don't you stay up at the register, alright? Let me worry about making the orders. Would that work better for you?" Barna...

Three Strikes Ch. 17

by Mrsgnomie on Dec 12, 2018
Gay Male

A person can only tolerate so much self-reflection before it becomes detrimental to one's health. That's how I was feeling by ten o'clock the next morning. The realization that I was a fuck-tard was weighing heavily on me—so much so that I'd started to feel depressed, which wasn't a normal feeling for me. I was a good person—I worked with sick kids, was debt...

Aquata Cove Ch. 28

by Feare909 on Sep 14, 2017
Gay Male

Chapter 28: Happy Birthday Merrick yawned as he walked out of Adam's bedroom, having slept in several hours after Adam has gone to work. As he walked the hall, he looked and giggled as he saw Nick on Jamal's bed, buck-naked and hugging a pillow. He walked in, and hopped onto the sleeping Latino. "Wake up, Nick! It's going on noon!" He said playfully. Nic...