Gay Challenge Stories

1,577 results
Orientation
Length
Source
Infinite Scroll

A Challenge

by drmweaver705 on Jan 20, 2020
Gay Male

All participants are over 18. ***** "The most I've ever come in a single night is four times," Dylan said, doubting his friend's claim. "I'm telling you I made him come six times in a three-hour period in one night." Anton said again. "I'd get him over here to tell you, but he says he's a straight boy like you, so he wouldn't appreciate me outing him wit...

The Purple Challenge Ch. 02

by BeltBuckle on May 11, 2020
Gay Male

The next Friday, I didn't even bother texting my friends. I knew exactly what my plans for the night were gonna be. Last week was fun, but I was ready for something more. Something better than a handjob. I felt confident and horny as hell. I knew I wouldn't sleep well until I got my rocks off, so I did what I have always done - I got up and went to get what...

F5: Cooking It Up

by sabb on Aug 18, 2017
Gay Male

(Author's note: This story is an entry into FAWC (Friendly Anonymous Writing Challenge), a collaborative competition among Lit authors. FAWC is not an official contest sponsored by Literotica, and there are no prizes given to the winner. Every story for this FAWC begins with the exact same line. Where it goes from there is up to the author.) * * * * "Upon...

Ultimate American Boy Challenge

by hasnoalias on Aug 18, 2017
Gay Male

*All characters in this story are above the age of 18* This story is the continuation and conclusion of a story titled "The Ultimate American Boy Contest" by redbeardedsf. I received full permission and blessing to continue the story. I suggest you read that story first, or you will be lost. ***** With loud music blaring, strobe lights flashing, and the...

Bet Upon Pool

by FadeEstates on Aug 18, 2017
Gay Male

The story starts out, one late afternoon, of course. The sun was shining, the birds were chirping, and I was planning to play a game of pool with my friend James. James is a good friend of mine, I have known him since he was 13 years old. James was smaller then I, height wise that is. When I was about 17 I always imagined what he was packing in-between his l...

The Game Bus Ch. 01

by darkfaded on Jan 28, 2020
Gay Male

**Station 1: The Game Starts** After stepping a few steps into the room, the light from the door illuminating his path suddenly vanished as the door automatically closed shut and locked itself. Adam is now standing in total darkness, void of any light, as though he had closed his eyes shut. He put out his hands and feels around, stepping ahead one foot at a...

Bigrig Ch. 18

by windstormy on Sep 14, 2017
Gay Male

The flight to Arizona seemed so long to Jonathan. He was quiet at the moment while he looked out the small window beside him. The ground was coming closer as they were making their final approach to the airport and the runway. His stomach lurched as the plane bounced for the thousandth time. Gripping the arms of the chair, he abruptly wheezed, tossing his h...

Heal Me Pt. 01

by chiquinquira on Aug 30, 2017
Gay Male

David My life is quite boring to the strangers' eye. I start my days taking my border collie Koda, for a morning run in the nearby park. After showering I leave to work and have my breakfast while driving. Then work, work, work and after that I usually go hiking or biking with Koda for an hour or two. When we get home I make dinner and have a nice quiet eve...

MTMF League Ch. 01: Connor vs. Johnny

by the1deros on Jan 16, 2019
Gay Male

Connor has been fucking the newcomer back and forth for almost one hour now. He has turned the poor boy in his whining bitch. Connor would have some mercy on the younger man if the freshman wasn't a cocky bastard that thought he had a chance against him. Connor not only is a bigger and stronger specimen of pure toned muscles, he also has 2 years of experienc...

Ben Loves a Challenge Ch. 05

by PDreadful on Dec 3, 2019
Gay Male

Dean brought him home again, only this time he was sober. Ben was so nervous and excited that he could barely contain it. To be honest, he felt like a teenager again. He only had a week to convince Dean he was serious, so he had to make tonight count. "What were ya thinking for dinner?" Dean asked, kicking off his shoes near the door. Ben looked down at hi...