When betting between male friends goes too far (part 1?)

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We had met online, on reddit. Mutual interest in table tennis of all things. I had played a bunch years and years ago in school and was itching to get out and play again. I’m married and mostly content, even with a dead bedroom, but it was a nice reason to get out of the house regularly and do something on my own.

Anyway, I met him on reddit, he was local, played table tennis and even had his own table in his finished basement. There was nothing sexual assumed or even implied, just a couple of guys getting together to compete at something.

We met in a bar first though and got to know each other over beer. It was easy conversation and it was nice to entertain the wondered of making a male friend once again. Things went well and we went to his house and played our first game. It’s been decades for me and I lost, but it was fun.

We ended the evening and I drove home, but we kept in touch. Decided to meet again, at his house this time, for more table tennis. It turned into a weekly thing. Every Friday night I’d go over and we’d just lose ourselves in playing. He often beat me at first, but a lot of it was from unforced errors, or so I wondered. As that muscle memory came back though, I made less errors and eventually was winning more than I was losing.

This went on for quite awhile. We developed a nice casual friendship over ping pong. We started some good natured trash talking and fake gloating when winning. As things were more comfortable, we often had a few beers while playing as well. But I was happy to get out of the house, have a friend, get some exercise, and some time separate from the wife. Things at home continued to be fine.

Things changed the last time we played though, in a big way. I had arrived like typical, trash talking and drinking started early, and we got to playing. I kept winning and was feeling pretty cocky (and a bit buzzed).

He proposed a bet for the next games to make it more interesting. And a little humiliating for the loser. Find out though, that up until this point, there had been nothing to suggest we were just two straight buddies competing.

He proposed that every time someone lost a game, they forfeit an article of clothing to the winner. It was interesting phrasing, but I was so shocked by the bet, and the subsequent taunting from him that I didn’t think it through.

I was beating him pretty consistently today and between the beer and the taunting, I agreed, thinking it would be embarrassing for him.

The next game started and it went much differently. He smoked me. I was red faced as he gloated and demanded an article of clothing. I took off my shirt and practically through it at him. Remember the ‘forfeit’ part? Yeah. So I had to win to get it back. Lose and lose another piece. Maybe I should have quit there.

But of course I didn’t. I was winning before, I could win again. Or so I wondered. My shoes were next. And then socks. Which made me play even worse. He kept winning by greater margins.

I was pissed and determined to win. I couldn’t go home shirtless and without shoes. I had never tried to win so hard. I failed and that meant…. Pants. And nudity. And then playing nude in order to win my clothes back. Completely humiliated, I took them off and handed them over. I couldn’t even meet his eyes.

He drank from his beer, smiling and full of confidence. Despite my embarrassment, I was determined to play again. And win damn it, but he paused. I could feel his eyes on me as he said, “we have a problem. If you lose again, you have nothing else to strip off, so… I’m going to need something else. I won’t force you but… If you want your clothes back, we have to play again and you need to win. But if you lose… Well, let’s just say it’s been a long time since I’ve had a blow job. You can refuse to play of course… And go home naked, which might be a little awkward. So… It’s up to you dude.”

I was floored. And humiliated. And pissed. He was so calm as he spoke. It was infuriating. I stammered at him, my face red. I was mortified and scared. I couldn’t go home naked. And my clothes were nowhere to be seen. How had he managed that?!

He had trapped me. Thoroughly. I didn’t really have a choice here but to agree.

We played, him smiling and me sweating. The game was close. Very close. It reached deuce. I had never played so hard, nor had the stakes ever been so high. I got the benefit point and one more and I would win! Nope, ball hit the net and went out, and back to deuce. He won the next point, smirking. And then..

Game, set and match.

He couldn’t be serious. He couldn’t be. I couldn’t help it, I looked down to his crotch and to my horror, could clearly see the outline of his large and shockingly hard cock against his pants.

“Excellent,” he said quietly, “I am in sore need of some release. It doesn’t matter that you’ve never done it before, you’ll be fine. Unless…. Well, I suppose we could keep betting. You could win and not have to do it. That would be a bummer. But…well, if you lose again… There would have to be another price to pay. What do you think?” he asked.

My knees nearly buckled. I could suck off man for the first time right now, or try again and what? He hadn’t said. But trying to get out of this, no matter the odds, was very tempting.

“What….what would the additional stakes be?” I asked, my voice tenuous.

His smile was deep, and his voice smooth as he said, “have you ever been tied up?”

NSFW: yes

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