Gay Cowboy Boots Stories

768 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com

Cowboy Wannabe Gets His

by NKY_man on Sep 14, 2017
Gay Male

The clubhouse at my apartment complex has a well-equipped gym as well as an outdoor pool and shower facility. Strangely, these amenities are rarely taken advantage of by the people who live in the apartments. As it is, the sign-in sheet at the clubhouse routinely lasts for three months before it has been filled up and even then few signatures except mine ar...

Derek Pt. 03

by TAHammer on Apr 27, 2020
Gay Male

Everybody was decked out in cowboy boots, jeans, and bandannas at the afternoon barbecue. Of course, Derek with his sleeveless button-up shirt, tight jeans (with a big buckle belt), and cowboy boots looked like the Playgirl cover model for the cowboys issue. Everyone watched him swagger around the patio. Karen gave him a cowboy hat, and every gay guy and str...

Cowboy Hats and Calamine Lotion

by PheeGee on Sep 14, 2017
Gay Male

"Dude, I have something you so want to get in on!" Mitch whispered excitedly into Craig's ear. Craig turned away from loading paving stones onto the back of the truck and eyed his bud suspiciously. They'd been friends ever since Craig had hired on, right out of high school, with Mitch's dad's landscaping company, and the subsequent four years had taught Crai...

Cowboy Wannabe Rides Again

by NKY_man on Sep 14, 2017
Gay Male

I last wrote about a guy I met at the clubhouse gymnasium of my apartment complex. Almost from the day of our first tryst I had thought about another encounter with this man. While it is not uncommon for me to fantasize about past conquests, it is very uncommon for me to want to go back for seconds. Since I had become sexually active in high school I realize...

Raunchy Cowboy

by casper hunt on Aug 18, 2017
Gay Male

Hi there, one more story for you. This is a story about an affair with a cowboy. I think it is everyone's fantasy to have sex with a cowboy. Let me tell you one more thing. I have written about something called 'gay tests' in this story. I conjured it up right when I was writing. I have no way of knowing if these tests work or not. They are just a figment of...

Champagne Surprise

by pdxjo on Aug 17, 2017
Gay Male

When in any bar, gay or straight, I love to watch people without them being aware. It's fun to try to figure out the stories of their lives and those of the people they are with. On this night, from across the smoky and noisy bar, I immediately noticed the two guys who seemed to be arguing about something. Every few moments they would glance my way and again...

Jason's Trip to Mexico Ch. 04

by beefylatn on Sep 25, 2017
Gay Male

Jason was pushed into the jail cell by the two officers causing him to stumble and fall, landing on top of a large snoring drunk inmate as the cell door clanged shut. "OOOOFFFFF!" the large hairy sweaty inmate exclaimed as his eyes flew open and he glared at the naked blond stud that landed on his belly. "I'm so sorry, the cops threw me in here and I trippe...

Death in the Rockies Ch. 02

by sr71plt on Sep 14, 2017
Gay Male

The Ranchero was a bull-riding bar, complete with sawdust and peanut shells on the floor and a twangy country and western voice singing a "girl done gone up and left me" song assaulted a raucous crowd of men from the rafters. The basement club was set smack dab in the middle of Manhattan, but you'd never know it was there—unless you were a gay male, cruised,...

Suits

by sr71plt on Aug 30, 2017
Gay Male

It was a steamy, smoke-filled night at Hernando's, and I and the other two guys had been dancing to the music on the small stage for twenty minutes. I was already down to the ten-gallon hat, the pinto pony vest, the cowboy boots, and the low-slung belt and six-gun holsters with the even lower slung eight-inch gun swinging in between and nothing else on when...

Tramp Steaming Ch. 02: Christophe

by sr71plt on Nov 27, 2017
Gay Male

I pulled a pair of low-rise shorts and a sports shirt out of the closet, put them on, leaving the sports shirt open and not tucked into the shorts, and padded down to the hotel reception desk to start the process of reporting I'd been ripped off, was temporarily destitute, and needed help to start the process of canceling cards and replenishing my funds. I w...