Gay Dress Stories

3,413 results
Orientation
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Infinite Scroll

College Break at Home Pt. 03

by jtwy on Nov 2, 2020
Gay Male

Just then, they heard the house door slam, indicating someone was coming out to the shed. In a hurried mess, they threw back on their athletic clothes, barely getting everything on before the door opened up. "What happened in here?!" It was the bartender. After walking into the shed, he had only needed a second to examine the situation and realize what had...

Accommodating the Rugby Men Ch. 04

by Cumfusion on Sep 14, 2017
Gay Male

It was the strangest thing to try to resume where I had left off in my work the previous day. Since about 6 pm the day before my whole life had changed and here I was at 9 am the following morning trying to organise my mind around work! It wasn't as if it was first thing in the morning and I could think of yesterday as just some fantastic dream. Barry and...

Dick - The Teen Gym Stud Ch. 07

by dominanceaddict1 on Dec 9, 2019
Gay Male

"What's your idea Ryan?" I asked, looking over at him. I was supposed to be the responsible adult escort for Ryan and a friend to go to his school dance. But earlier that night I had been dressed up in a costume—by Ryan's older sister—as a lady bumblebee, complete with giant tits, a short dress, thigh-high stockings and heels. Ryan's had then essentially u...

To Live and Fuck in L.A. Ch. 02

by Fit_for_a_Fuck on Jul 11, 2018
Gay Male

The next morning Mr. Castle had a car pick Nicky up at his apartment and drive him to the tanning salon in Beverly Hills. When he arrived, he walked up to the front desk where a very attractive older woman with brunette hair in a ponytail and big tits was sitting. "Hi, my name's Nicky," he said. "Mr. Castle sent me here." "Ah, yes," she said with a sligh...

Humiliated at a Motel

by missy_willow on Jul 3, 2019
Gay Male

Humiliation has long been an important part of my sexuality. Being called names, getting slapped and choked, and being exposed in public get me harder than anything. I decided to pay a man who advertised as a Master who cared only about denigrating those who employed him. We agreed on a price and I arranged for a hotel room near the highway which was freque...

Co-worker's Man Ch. 39

by rmdexter on Sep 14, 2017
Gay Male

I awoke to the sounds of music coming from my clock-radio. As I came to, my thoughts were filled of the night spent with my face plastered to my mother's steaming twat. I breathed deep and could smell her strong female scent still on me. I ran my tongue around my lips and could taste her heavenly nectar where it had dried on my skin. My face felt tacky and c...

Encounter in the Adult Video Arcade Ch. 02

by walterio on Apr 3, 2019
Gay Male

INTRODUCTION This story takes place in the 1970s before the threat of aids when bareback sex was commonplace. It is completely fiction and all characters are 18 years of age or older. * CHAPTER TWO PAULA'S VISIT Over the next several days until Paula's arrival things stayed pretty much on course around the apartment. I never got tired of fucking Robby...

Truckstop Young Wife Neighbor

by Alluring_Crimson_Shifter on Jun 12, 2019
Gay Male

Wendy lived with her husband in a middle class neighborhood. It was a comfortable neighborhood with a convenience store within walking distance. There was a retail strip nearby with hair salon, a barber shop, parts store, and a book store with an arcade. Also there was a truck stop next to the neighborhood across a wooded area. On this sun shiny day Wendy w...

An Eventful Day

by demwesker on Aug 18, 2017
Gay Male

***** This morning was not the usual one because it's the first time my honey asked me to dominate him. Prior to today, he was always the dominant one, but this morning shows that he loves to be dominated too. "At least one time, please?" His word echoing in my head, it made me wonder that maybe he is a switch. Even though a switch, the reason why he'd al...

Tanglewood Entanglements

by KeithD on Dec 25, 2019
Gay Male

July, 2013 I thought of it even then as my last fuck—our ultimate fuck, the farewell fuck—with Edward Teng. I still think of it that way even though, technically, it wasn't the last time he fucked me, even in a physical sense. He'd rehearsed me early that morning at his cottage, Munch Cottage, on the grounds of the Tanglewood Music Center in western Massach...