Gay Crossdressing Halloween Stories

300 results
Orientation
Length
Source
Infinite Scroll

College Days Ch. 06

by jjdtx on Sep 14, 2017
Gay Male

Chapter 6 -- Tim and I get even with Pete My playing boss to Tim was an awesome turn on. He loved being told exactly what to do. He had been coming over to my dorm about three times a week. He'd only come over when Stephen, my roommate, was not going to be around, which I was hoping to change so that Stephen could see his perfect smooth body too. He came o...

A Halloween Carol

by RubenR on Oct 24, 2018
Gay Male

This is my contribution to the 2018 HALLOWEEN CONTEST. It is not a sex story. For those looking for detailed descriptions of strong, muscled bodies, or hot, steamy sex scenes, try the next one on the list; you won't find it here. As always I like to know how the story is received. Comments are very much appreciated (even critical ones; insulting ones not so...

Blood and Love Ch. 12

by Eternalivan on Sep 25, 2017
Gay Male

Chapter 12—True Love ******************************* Sean's story VIII ******************* The sudden noise made by the screaming alarm cut through the dead silence in the room, pulling me out of the thoughts I had buried myself in. I sighed but didn't take my eyes off the ceiling. With usual habit I extended my arm and hit the alarm shut. Immediate sile...

Drag Queen and the Indecisive Guy

by jim_janes on Jan 16, 2019
Gay Male

Walking down the steps my mind was at war with itself. My two personalities were screaming at each other. I have always had debates in my head. I envy those who know what they want or know what must be done without hesitation. I was never that lucky. Every decision was a WWE match between my ears. Indecision was my middle name. Mostly the internal argument w...

The Sound of Your Voice Ch. 04

by Nyhtfall on Sep 14, 2017
Gay Male

It was still dark and storming when Evan awoke. He glanced over to find Josh still sound asleep. Leaning over, he placed a kiss on Josh's forehead, who mumbled and snuggled deeper into the bed. Smiling, Evan slipped out of bed, and pulled on a pair of sweats and shirt. Quietly, Evan made his way downstairs. The power was still out, and the candles throughou...

The Bartender Ch. 02

by Pan2 on Jun 8, 2020
Gay Male

As soon as Roger walked through the saloon-style doors, Kent reached for a glass. He'd never before seen a man in such need of a drink. If the dark rings under his brown eyes weren't enough, his incorrectly buttoned-up shirt and mop of dishevelled brown hair clearly used to more attention than it was currently getting were a clear indication that Roger was...

Can I Borrow Your Boyfriend?

by knowsbetter on Mar 2, 2020
Gay Male

"Ok, Ok, I got one," Josh said. I was out with my friend Melissa and her new-ish boyfriend Josh, and we were three glasses of prosecco into a late brunch. The waitress was clearly hungover and didn't give a shit, service was winding down, and we were off in a corner gossiping and talking trash. The current topic: terrible first-date icebreaker questions. "B...

Dick - The Teen Gym Stud Ch. 08

by dominanceaddict1 on Dec 24, 2019
Gay Male

The pickup truck pulled to a stop. I was in the front seat of a Ryan's car, on my stomach laying across the wide bench front seat of the pickup truck. My ass was sticking in the air and the high schooler's strong hand was on it, squeezing. My head was in Ryan's lap, licking up and down on his massive, mostly-erect, teenage cock. At the moment, I was playi...

Historic Costumes

by MSTarot on Aug 18, 2017
Gay Male

The phone has been ringing off the hook for the last week. "Historic costumes," I paused and waited for the inevitable question given it was October. "Yes, ma'am, we do rent for Halloween. No, we only carry costumes from pre-nineteen hundred." I rolled my eyes at the Hanna Montana as a slut request. "Yes, we have several pirate costumes in stock." Holding...

Last Months in the City Ch. 04

by thealphamale on May 11, 2020
Gay Male

Chapter 4: The strange case of Danny Phantom and Marty McFly Jamie woke up first, immediately feeling the warmth of Chris' heat all over his body. He eased into the muscled frame that proved to be soft enough for him to feel comfort as he listened along to the quiet little breaths the boy let out- the same ones that lured him to sleep the night before. All...