Gay Crossdressing Halloween Stories

300 results
Orientation
Length
Source
Infinite Scroll

Connor's Pretty Horny Pt. 09

by connorwitmer on Jan 30, 2018
Gay Male

So, to say the least, I had suddenly become hot shit. Just kidding. If anything, I now felt like a complete imposter. Alex seemed to have accepted me as somewhat cool, and now Robbie added a level of intrigue, and Henry was ever present. Despite being hot shit, I rarely saw a text from Alex. I had already placed him in the category of "people who don't text"...

It Was So Exciting

by sindyxdresser on Aug 18, 2017
Gay Male

It was about 230 am Friday night when I walked into the Crypt adult book store on 30th Street in San Diego Calif. The Crypt's usual clientele was mostly gay men, and tonight was no exception. I felt my face burning as I walked back into the peek booth part of the store. These booths had no doors or curtains so offered no privacy of any sort. There were sever...

The Reluctant Bear Hunter

by newpaulman on Jul 3, 2019
Gay Male

First I must apologise to any gay men reading this who like their stories with a romantic element. That is not what I am looking for with a man. I am a part-time bisexual. I can go months without thinking about gay sex, but then the urge comes back. The urge to be fucked, that is. The urge to suck a cock and see spunk fly from it. The urge to get naked with...

High School Jock Haunting

by marquis06 on Oct 24, 2018
Gay Male

Warning: this story contains scenes of violent, non-consensual sex. **** Steven could not believe that he had a fat quarterback's cock driving into his throat. A relatively skinny, splayed out like a roasted pig on a locker room bench, with a fat dick plowing into his mouth. It was juicy and veiny, everything he had imagined from the porn scenarios he had...

Costume in a Costume

by MVP6 on Jun 15, 2020
Gay Male

It all began three years ago, in October. I remember because my wife was visiting her sick mother for an extended period of time. Feeling unusually alone and commonly horny I had too much time on my hands to consider the most satisfying ways to shoot jizz. After many lonely nights of jerking off I reflected on the odd realization that many of my fantasie...

Rex's Horny Halloween Pt. 04

by TeamCravings on Jan 7, 2019
Gay Male

Halloween night grew later and more bewitching as each moment passed. The gay party in the chic London flat was reaching new heights of horny debauchery thanks to a very open and eager Rex! The stunning mature 40 year-old ginger haired stud was laying spread and gaping for all the guests to enjoy. The speculum was truly a miracle and the view deep inside Re...

Gloryhole Illustration

by MVP6 on Jul 15, 2020
Gay Male

In my last letter I wrote about my first experience sucking cock. It was really great and if you want to read about it the title of the story is "Costume in a Costume." In this letter I will share my next interesting experience: It was now August and I was anticipating Halloween which would be here soon. This year I was planning to dress up as a woman aga...

Pumpkin Patch Snatch

by KeithD on Sep 14, 2017
Gay Male

I didn't know if it was the unseasonal heat or the heavy work we'd done that day or Jake's scary stories or Miguel's empty bed that kept me awake in the dormitory that night, but I had nervous energy to spare. I would doze, but I'd wake up with a start and look over at Miguel's bed, the emptiness of it now explained, and then I'd check all of the other beds...

Crossdresser's Unexpected First Time

by kprice1984 on Nov 27, 2017
Gay Male

Just want to say firstly, that this story is 100% true. Secondly, it was much better in person. I'm just getting around to writing it after several years. ***** I'm a 20 year old guy, very good looking, easy to get girls. Brown hair, green eyes and a sexual appetite that's hardly ever satisfied. I had always had a craving or tendencies towards being a lit...

My First Kiss

by amygurl on Aug 18, 2017
Gay Male

It all started about 2 months ago when a new neighbor moved into the apartment next door to me. His name is Jason, he is very personable and just an all around amazing guy. He is 34, about 6'3" with black hair and blue eyes and we hit it off pretty much as soon as we met. We are both veterans and newly single and we both liked to watch sports on TV, but we d...