Gay Losing Bet Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

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...

A Tale of Two Brothers

by kurrginatorX on Dec 30, 2019
Gay Male

Editor's note: this submission contains scenes of incest or incest content. * After graduating high school, twins Mark and Clark Dixon took different career paths. Mark joined the Army, feeling the need to give service to his country, while Clark attended college. Although they rarely saw each other, never home at the same time, they did maintain contact t...

College Cock Sucking Slave Ch. 02

by fulhammock on Aug 29, 2017
Gay Male

After losing the bet to Dan, and sucking his dick, it turned out that my straight friend, really liked the way I sucked him off. The combination of me being so into it and my ability to actually get that fat cock head past my lips was one he could not refuse. The next day my phone rang at 3:00pm. He told me he had hockey practice at 4:00 and asked if I was...

The Bet

by mikec1010 on Aug 18, 2017
Gay Male

Lisa and Mike had been married for over seventeen years. Lisa was thirty-nine, blonde, with blue eyes, and a very nice figure, even after having three children. Mike was forty-one, with black hair, brown eyes and in pretty good shape. The two had a very good marriage and a very good sex life. They enjoyed sex and made it fun with role play, toys, and some...

Doubling Bets

by sr71plt on Sep 14, 2017
Gay Male

I should have known that the sneaky Dutchman had all the angles figured when he suckered us into betting against a myth in the Men Only back room at Cowboy's Bar in Bangkok's Patpong district. He waited until the third revolution of the happy hour clock—when we were all soused and sluggish—and then entered with a boy-built Thai. I recognized the Thai immedia...

A Friendly Wager

by binroe on Aug 18, 2017
Gay Male

I stared blankly at the television. It was a chip shot. A gimme. My favorite football team had just missed a 22 yard field goal that would of won the game. Hell my 14 year old neighbor could of made that kick. What rubbed salt into the mental wound was my girlfriend, who was dancing around the living room with glee. We had made a little wager on the game a...

Becoming Jerry's Master

by 0ra11yfix8ed on Aug 31, 2017
Gay Male

So, you like to get sucked. Who doesn't? You've been around long enough to know you don't always get what you want from your wife. Having an affair with another woman is too risky so you started to think about the idea of getting a blow job from a guy. It didn't start out that way. You were reading porn and jacking off. One thing led to another and you foun...

Defeated Jock Ch. 02

by maxpotter on Mar 12, 2019
Gay Male

Taylor's phone pinged. He had been laying on the floor, head buried in his arms for a while now. [Be sure to get to class tomorrow. Enough of your dumb ass skipping!] Kam's text seemed like an order. Taylor just stared at it. How the fuck was he going to go to class? Everyone had seen the videos, he's be a laughing-stock. He didn't want to face that. But Kam...

Our Bath

by Elected on May 14, 2019
Gay Male

"Whew! What a run, huh, buddy?" Lee swung his arm around my shoulder. Immediately I felt the sticky heat from his arm soak my neck, and I recoiled. "Lee, quit it! You're all sweaty!" "What are you so worked up about?" Lee laughed, giving my shoulder a squeeze and pulling me tighter to his body. I wriggled and squirmed, getting myself free and shooting him...

Paradiso Ch. 20

by SlyKink on Sep 19, 2017
Gay Male

Day 5 Continued As we sat and ate I recounted the story of golfing that morning. It was an ordinary, mundane dinner conversation and aside from the fact that we were naked it was no different from a thousand other times we had spoken about our day over dinner. I wanted to draw out the moment so I filled in lots of details about the game; slicing on the thir...