Gay Lost Bet Pegging Stories

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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...

It’s Independence Day

by DavidPatrick on Sep 5, 2018
Gay Male

Every 4th of July, I travel from my downtown loft to my sister's vacation homes on Thomas Hill Reservoir, an expansive lake in north central Missouri. The lake, which is huge and placid, is virtually unknown. On any given 4th, there are a half dozen or fewer boats on the water, in stark contrast to the more bacchanialian and busier Ozarks two hours to the so...

Dangerous Games Ch. 01

by bjmichaels on Aug 18, 2017
Gay Male

JOHN'S STORY I don't know how I got myself into this mess--I only wanted to earn some money and buy new tires for my car. Now I am trapped, being forced to do things I would never have done in a million years. The worst part is I can't tell anyone. There is no way in the world I want ANYBODY to know what I do for Tommy, or for that matter, what I'm accused...