Gay Costume Stories

398 results
Orientation
Length
Source
Infinite Scroll

Liam Ch. 05

by Lucas96 on Jun 8, 2020
Gay Male

Author's Note: this story involves cuckolding and humiliation. A month had passed since I had watched Kyle and Liam get fucked by Marcus and Brad. Kyle and Liam continued to fuck whenever they wanted - it was not at all unusual for me to get home from classes to find them making out on the couch or fucking in my bed. They loved teasing and humiliating me, a...

Misdelivered Mail Male Sex Training

by sr71plt on Sep 14, 2017
Gay Male

Allen came to the window of his Maple Street bungalow and looked out at the driveway at the unmistakable sound of the purring of an expensive sports car. He had arrived in time to see Jack unfold his elegant six-foot-four frame out of the red Porsche Carrera convertible and run his hand through a thick mane of auburn hair with frosted highlights. The man was...

Backstage Tensions

by Whorephology on May 9, 2018
Gay Male

The hot dressing room lights beat against my skin, and sweat begins to run down my forehead, making its way past my blue eyes and heading for my chest. I look in the mirror, between the blinding lights, and see that the top button of my costume has come undone. Sighing, I re-button my shirt before exiting the dressing room and heading for the stage. The hal...

Pantomime Cow

by Robert_Furlong on Aug 31, 2017
Gay Male

Part of the 'Butt Monkey' series of stories by Robert Furlong === Jake mentioned over tea that the drama department at his college was looking for someone to help out with the Christmas pantomime. It was still early November but rehearsals were already underway. "I didn't think you were interested in drama, Jake." "I'm not actually in it," he replied, th...

P.A. Club Night

by sr71plt on Aug 18, 2017
Gay Male

"God, Leon. An M-8 special? Eight? I have to take eight of them in one gig? And what the hell is an Edwardian?" I knew what this was really about. I damn well knew that Leon was ticked because I had told him I was taking three months off. "Hey, you're the one who told me in almost exactly the same breath that you were taking a whole chunk of time off but th...

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...

Gym

by MVP6 on Oct 5, 2020
Gay Male

This is my seventh letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore. (M+M, oral, anal) In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick unsuspecting men into letting me give them my first blow job. In my second letter "Gloryhole Il...

Zebulon

by MVP6 on Jul 6, 2020
Gay Male

This is my fourth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side. In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick unsuspecting men into letting me give them my first blow job. In my second letter "Gloryhole Illust...

Dr. Aaron and Officer Brian

by brian420d on Aug 18, 2017
Gay Male

When we met in the crowded living room he was flanked by a big breasted blonde on each arm. It was a Halloween party. He was dressed as a doctor, in scrubs. The two blondes had their asses hanging out of white mini-skirts that came in the nurse costume packages at the Halloween super store. He smiled at me and gestued his head like I should cross the room to...

Rex's Horny Halloween Pt. 02

by TeamCravings on Dec 12, 2018
Gay Male

Handsome Rex Davenport soaked his fit six-foot body in a nearly full tub just before having to get ready for work. It was Halloween and this ginger-haired 40 year-old had a fascinating evening ahead of him. This special night had all been suggested and planned by his dear sex mentor Lorna, a hot MILF who had launched herself headlong into his life in just a...