Gay Boxer Briefs Stories

4,839 results
Orientation
Length
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Infinite Scroll

College Roommates Meet Ch. 07

by tomthewriter on Sep 14, 2017
Gay Male

At 7am Devante woke up perky and eager for his first day of college classes. He grabbed his shower caddy and raced to the showers to get washed up and ready for the day. After getting dressed and grabbing a granola bar, he was even nice enough to wake up Spencer before heading out the door. First on Devante's class list was macro-economics. That was then f...

The Boifriend Ch. 02

by AdmiralSquish on Jun 19, 2019
Gay Male

[pre-story]This story's not dead! I was a little stuck trying to figure out what to work on, and I got some comments recently asking for more M/M stuff, and then I got inspired and now here we are. Convenient that the first story to go public in pride month is M/M. Content Warnings: M/M, femboy, sissy, potentially offensive dirty talk Disclaimer: All chara...

Daddy Next Door

by Lsub19 on Sep 14, 2017
Gay Male

Nick was just a regular 19-year-old guy, he was pretty lean with a completely smooth swimmers tanned body. He also happened to be gay and had been dreaming about his next door neighbor for weeks, since he had moved in. James was a single 34-year-old big muscular man who lived alone. He had decided to move in to that neighborhood because it was closer to wor...

Cum Sucker

by BallZucker on Aug 30, 2017
Gay Male

Authors note: This is one of my fantasies. It is not a true story. I have only sucked one cock in my life when i was younger, and haven't stopped thinking about it since. I hope you all enjoy. I was eighteen. Long blonde hair, baby faced, cut build (I was in water polo), and tan. I had been browsing on a hook up website for a while. My parents were out of...

Underwear Friends

by ramon25 on Sep 16, 2017
Gay Male

I was dreading taking a gym class in my senior year in high school. I missed gym in my junior year due to some surgery, so I had to take it as a senior in order to graduate. All of the other guys were juniors that i didn't know very well, but I had to make the best of it. Partway into the school year, a new guy transferred to our school from Texas. Mark...

Cocksucker's Blow and Go

by thejazzdude on Aug 17, 2017
Gay Male

This story is loosely based on a true story. ***** I waited. The room was dark, with only a sliver of light coming through the edge of the blinds, casting just enough visibility in the room to not walk into a wall, but never enough to see anything, like a face. I was on my knees, in just my boxer briefs, staring at the front door of my apartment. Why, mig...

The Older Man Pt. 05

by t2u1ck on Apr 1, 2020
Gay Male

It's some time since I wrote the stories about my affair with a much older man. I'm married and in my twenties and Tom is a widower in his 50s. I had not recognised that I was bisexual until I met Tom but since we first got together I have enjoyed the delights of oral and anal sex and shared a fetish for briefs, especially with shirts tucked in them. We also...

Underwear Friends Ch. 05

by ramon25 on Sep 16, 2017
Gay Male

During the middle of summer, while my little brother was away at camp and my dad was on a business trip, my mother and I had connected during a period of mutual loneliness. My dad had been having an affair, and my best friend and lover, Mark, had moved back to Texas. My mother and I had a drunken night of sex, that led to a few more exploratory sessions, bef...

Web Ch. 01

by Cubanizer on Aug 18, 2017
Gay Male

Web Ch. 01: Greg & Ruben If there was one thing Greg loved about himself, it was his tongue. In his wildest naughty laughs, that tongue would climb out, long and wet. And when he wanted to be particularly filthy, he'd work his tongue like a seductive belly dancer. True, his body wasn't bad at all, but that was something he could work to perfection. His ton...

The Bitch Top

by TuxedoPirate on Sep 21, 2020
Gay Male

He was tall and handsome and toned. He was like Adonis. Even his cock was the epitome of manliness. It was ten inches long and as thick as my wrist. When it was hard, it was like sculpted marble. I was going to enjoy tonight. I was laying on my blue satin bedsheets, arms behind my head and legs spread out. My cock was hard and was straining against my boxer...