Gay Lost Bet Stories

11,538 results
Orientation
Length
Source
Infinite Scroll

Bill's Sexy Straight Grandson

by javierp25 on Aug 18, 2017
Gay Male

Mike always took time to visit his grandpa at the retirement community. He owed that to the guy who had been a father to him after his own dad left when he was a toddler. Bill had been a tough with Mike, but strong hand had made Mike the successful young man that he is. At six foot two, two hundred and twenty pounds his beefy muscular body and gorgeous bla...

TJ Ch. 03

by jt_hooks on Mar 6, 2018
Gay Male

"Hey there, Little Buddy. How are you?" Those seven words broke my heart. No, that's not it, it wasn't the words. It was the look on Josh's face that made my heart shatter into a million tiny pieces. How fucking stupid could I have been? There were signs everywhere, written with big, bold, red letters, warning me to proceed with caution. He played football...

My Giant Cock Obsession

by richardgranite on Sep 14, 2017
Gay Male

I was playing some basketball down at the gym the other day with a bunch of my buddies. We had a great game, strenuous, but fun. Afterword, instead of hitting the showers, Cody and I just stayed in our gym trunks and t-shirts and I went out for a couple of beers. Cody's a great guy. A 31 year old divorced stock broker, 6'4" tall and chiseled out of granite....

Losing Bets

by XxPrinceAnonomousxX on Dec 9, 2017
Gay Male

"I'll make you a bet," Giovanni said. I looked over at him hesitantly. "I bet you our team will win tonight," he said, and I thought about it, our team never wins, though. "But our team never wins." I said, and he smirked. "What are the terms of this bet?" I asked. "If you win you get a hundred dollars. If I win you have to do whatever I want for an enti...

Education of a Skateboarder

by timmywells on Aug 30, 2017
Gay Male

Some people figure out who they are early in life, it takes others a bit loner. Some never do. For Brad Keeler, he started figuring things out after graduating from high school. ... "You sure this is okay here?" the driver of the car said after I told him that he could let me out at the corner. "I can take you right to your house if you want." "No, this...

Old Guys Teach Me a Lesson

by RSchwuler on Oct 15, 2017
Gay Male

This story is a very over the top work of fantasy, and it contains non-consent, blackmail and humiliation elements. ***** I work late so I like to go to the gym in the last hour before it closes, when I practically have the place to myself. Even though my job is crazy these days, I still take working out seriously and get myself to the gym every day, and...

The Adventures of Ted and Mark

by sensual_senior on Aug 18, 2017
Gay Male

Mark and I met at a local Senior's Center. Both of us are healthy, active retirees in our mid 60s. He had lost his wife, Carrie, of 26 years to cancer about 9 months before we met. I had lost mine to surgery complications abour 11 months before. Our mutual interests and lonliness drew us together like old friends meeting again after years apart. We watched...

Workout Buddies Ch. 02

by 60031Guy on Nov 27, 2018
Gay Male

Author's note Hi there, thanks for taking the time to read this story. Please let me know what you think. This is my second story submitted anywhere, and is a continuation of, Workout Buddies, Chapter 1, The Bet. Folks seemed interested in the first chapter, so this is the first of several additional chapters that continue the story of Larry and Dave (and n...

Shopping Fun

by hasnoalias on Aug 18, 2017
Gay Male

I had attended a rather disappointing gay orgy about two weeks ago. I found myself to be lost in a sea of other bottoms and very few desirable tops. I was naked like most everyone else, but I just wasn't into it. I had received several offers to have me fuck someone's ass, but I preferred to be the one who took the hard cock up my young ass. Before I left un...

Blissfully Hooked Ch. 01

by adjoaq on Sep 25, 2017
Gay Male

Comments, critiques and tips are welcome. Kyle Parker vs. Aaron Hunter The Contract! *** Kyle Dylan Parker was what most people would call enthralling. He was at least six -feet-three, good-looking and extraordinarily sexy. With his captivating soft hazel eyes, long dark eyelashes, dark blonde hair cropped very short, and his heart-stopping smile, Kyle...