Gay Lost Bet Stories

11,538 results
Orientation
Length
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Infinite Scroll

Poker Party

by buckeyes on Aug 18, 2017
Gay Male

Once a month, me and the guys get together for a friendly game of poker. We talk a lot of shit, drink a lot of beer and take turns losing money to each other. This must have been my night because I was down about 50 bucks. I was having a good time so it really didn't matter much but I only had five dollars left and the game was not going to be over for about...

Our Bet Ch. 01

by Elected on Apr 24, 2019
Gay Male

Lee grinned. "Won again." I grit my teeth in anger. What the fuck? This was my game. I'd barely even shown him how to play but somehow he'd gotten the hang of it in a few hours—and now he was beating me? This was such bullshit. Lee flipped my controller away carelessly and climbed to his feet, stretching with a groan of satisfaction. "I guess all that talk...

Two Married Friends Discover They Have Bi Tendencies

by floridaguy2001 on Sep 15, 2017
Gay Male

I have known Tom for many years. I have always been attracted to him, always wondering what it would be like to suck his cock. I have had opportunities, like the time he was staying in my house and I came out of the bedroom, he was in obviously jerking of because he very quickly acted as nothing was going on when I entered the room. I pretended as if I hadn’...

Straight Chris Makes a Bet

by dunnohowtosex on Aug 18, 2017
Gay Male

Chris chortled and said "No way that's true! I've had sex with women multiple times in one day but I've needed a couple hours in between 'sessions'." I rolled my eyes and just face palmed. He had been talking about how unfair it was for women to have multiple orgasms when he was pretty much just one and done. I had just said, "You know what foreplay is? Wel...

Girlfriend's Bro Takes Charge Pt. 01

by somebody123 on Apr 17, 2019
Gay Male

I couldn't believe what I'd heard. "Two months?! Your brother will be here for two months?!" My girlfriend and I had just bought an apartment together in Manhattan and we finally had a place to ourselves. For years, we'd lived with roommates in the close confines of New York City. Now that we finally had a studio apartment to ourselves, Stacy had invited he...

The Soccer Bitch

by LDNBTM21 on Oct 15, 2017
Gay Male

Prologue: I had joined my local Sunday soccer league team not too long ago. It was a small county side based team with only 15 players. I joined knowing I had always been a good left winger. This I suspected was down to my small height and slim frame which gave me some pace and a good centre of gravity. I was also very energetic, at 20 years old; I could ru...

Fight Night: Round 01

by xzay24 on Apr 10, 2018
Gay Male

*This is my first story so please leave comments and let me know how I can improve. Thanks and Part two is on the way.* ***** How the hell did it come to this!? Why am I enjoying it so much!? Face down in a pillow I ponder these questions as the man I hated pushes his fat dick into me. "So tight." I hear him growl. "This must really be your first time hu...

The Bet

by WhiskeyIsGood on Sep 14, 2017
Gay Male

It was a Friday night, early and nice out; just nice enough for a trip down South Street by' myself. I loved coming down here in general but it was almost' always so much better when I was alone. Sometimes, I would walk around for a bit, and then take a trip down to the river and sit there for a while. Instead, tonight I was thinking of stopping in a bar t...

Joanie Ch. 01

by bjmichaels on Sep 24, 2018
Gay Male

"You look very nice today, Joanie," Mister B said to me as I climbed into his car. "Thank you," I replied, not even bothering trying to correct him yet again. My name is 'John' but since the day we met he has called me 'Joan' or 'Joanie.' He claims I misunderstand him due to his thick, southern accent, but I don't know, it sure sounds like 'Joanie' to me....

Roommates to Bedmates

by LoneOwl on Aug 30, 2017
Gay Male

I had just got back from work on a Friday. Brandon was already back at our apartment. He hugged me once I walked in. Since we're just room mates, I wasn't comfortable with it at first, but over time I got used to it. It's not much of a big deal for me anymore. It's sort of the kind of guy he is. We got along pretty well and had been living together for about...