[Bare Confessions] paying up

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Jimmy and I would often make bets on stuff like trivia games at the bar, sports games on the TV, or whatever he could think of to bet on. When we first started doing it, we’d bet on stuff like each other’s underwear or who would get fucked first. Over time, we progressed to looser had to find a third for us to fuck or get fucked by.

One time, we both had a bet to pay off, so we arranged for an afternoon session at Jimmy’s where we’d both pay off getting fucked by someone else, and maybe also fuck the guys. The guy I had arranged with showed up first, and we went in, Jimmy stripped down, and got on all fours. The guy just took out his cock, had Jimmy lube it up with some spit while I rimmed Jimmy’s ass getting it slick with my spit. He slid into Jimmy’s ass and really pounded on it for maybe ten minutes before he just pushed in and shot his nut into Jimmy. He pulled out, and put his cock away. We told him that we had another guy coming over, if he wanted to hang out and have some more fun. He said he’d stick around to see what the guy looked like, and we headed out front to wait for Jimmy’s find. Jimmy’s guy was this lanky Skater type, who I was excited to see, but my guy was like “fuck no, I’m out of here.” So he left, and Skater boy joins us, introductions around, and we head in.

We all got naked, and were having a real hot kiss and suck session. Soon we were all hard, and Skater had a real nice big cock and low hanging balls. Jimmy lubed up my ass, and skater slid in. He fucked me for a while as Jimmy watched. Finally after about 15 minutes of working over my ass with a combination of slow gentle strokes and furious pounding strokes, Skater pulled out and apologized that he just wasn’t going to be able to cum. He said he wasn’t even getting close, and that maybe he shouldn’t have jacked off before coming over. Jimmy suggested maybe a BJ; but Skater said that he just didn’t think he’d be able to cum. We talked for a bit, and Skater offers us both his ass. Jimmy and I took him up on that, and both of us planted a load deep in Skater’s ass, with me going first. While Jimmy was fucking him, he tried seeding me, but even with his ass full of my seed and Jimmy fucking him, he still couldn’t blow his wad. After Jimmy had planted in him, we all laid around kissing and chilling. A while later, Jimmy told us we had to leave as his roommate would be home soon, so Skater and I left. I still hang out with Skater and though we don’t fuck any more, though I wouldn’t mind if we did, we still have a good friendship.

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