Gay Challenge Stories

1,577 results
Orientation
Length
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Infinite Scroll

Station Ch. 00: Intro - The Game Bus

by darkfaded on Jan 22, 2020
Gay Male

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** ***Writer's Note*** This is my first time writing a story, hope you would enjoy reading it as much as me writing it. My characters narrated in the story, take on the appearance of Adam Foster and Nat Wolff from the show, room 104 season 1 episode 7, "The Missionaries." Sin...

The Game Bus Ch. 00 - Intro

by darkfaded on Mar 2, 2020
Gay Male

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** ***Writer's Note*** This is my first time writing a story, hope you would enjoy reading it as much as me writing it. My characters narrated in the story, take on the appearance of Adam Foster and Nat Wolff from the show, room 104 season 1 episode 7, "The Missionaries." Sin...

The Ultimate Muscle Hunk Challenge

by writerofgayer on Sep 16, 2017
Gay Male

One night I was really bored and I flipped on the TV. It had been a few years since I'd watched any TV show religiously, and I wasn't even sure there was anything good on. "500 channels and nothing to watch," I mused to myself as I flipped through the channels lazily. But then, just as I was about to give up, I saw a brief scene of two shirtless, heavily-mus...

The Challenge

by pdxjo on Sep 1, 2017
Gay Male

It wasn't until I was 27 years old that I had ever been fucked in the ass by another man. I'd given and received blow jobs, and done my share of jerking off with other guys, but I was totally naive and inexperienced about taking it up the ass. In fact, when I first started going to a local gay porno theater to be fascinated by the images on the screen, I act...

The Purple Challenge Ch. 03

by BeltBuckle on May 11, 2020
Gay Male

My friends were a little surprised when I blew them off for yet another Friday night. Of course, I didn't tell them the real reason I wasn't coming... Getting off in The Purple Challenge was so much easier than going out and picking up chicks! I didn't need to pay for any dates or pretend to be interested in whatever they had to say... No, the only thing I n...

The Greek Society Ch. 01

by BigWig69 on Aug 18, 2017
Gay Male

I remember talking to a mate at work about how much I missed my old playing days in football and longed for that team camaraderie, getting together after for drinks. I really missed it. He told me that he recently joined a new club and that if I wanted to come check it out, I was welcome to come. I asked what it was called and he said it was the Greek Societ...

The Purple Challenge Ch. 01

by BeltBuckle on May 11, 2020
Gay Male

It was another Friday night, and I was feeling a little pissed off. My friends and I were supposed to have a night out - drinking, chatting, then going outside wasted and doing something stupid. But all of them, one by one, flaked on me during the day. The last one of them canceled at 6 pm, which is pretty fucking late to flake out if you ask me! I didn't fe...

Twinks' Trivia Challenge

by Tiberius58 on Aug 18, 2017
Gay Male

I found the offices of TTC Productions on the top floor of a converted warehouse in London's Dockland area. After climbing up eight flights of stairs, I was confronted by a middle-aged guy who said, "You must be Peter. You're the last contestant." The guy led me to a changing room where three other young lads were getting stripped off. We took a shower the...

Miles's Revealing Clothing Teases Pt. 02

by sweetcobs84 on Mar 3, 2020
Gay Male

As we exited the staircase and entered the cafeteria, there was a collective gasp from a number of the senior class whose table had them facing our direction. Miles was a few steps in front of me. "What are you doing?" asked Ryan. "I was arrested," replied Miles. Recognizing the confused look on a number of the seniors' faces, I explained, "We were in Mr....

Getting Anthony Ch. 06

by maxpotter on Dec 12, 2018
Gay Male

Things were even better since you had been assured Anthony was doing all of this on his own volition. You had a level of comfort that you hadn't permitted yourself before. And the phenomenal sex had improved, as if that were even possible. Anthony had seemed to pick up on your greater ease and seemed happier than you had known him before. One day you got h...