Hard to tell who 'lost' this contest, since we both got off good
Brett and I met at the end of our freshman year, when his dad got transferred here. He wound up in my homeroom, but school only lasted about a month after that. Brett lived a mile away, and we'd gone over to each other's house a few times during school. Now that summer was here, we rode our bikes over to each other's place more often.
Brett is tall for his age and dark-skinned, I think he had some Korean blood mixed in. I'm a normal build, lighter skin with just a hint of 'baby fat.' The more we hung out, the more comfortable we were with each other, and I'd call him my best friend.
One afternoon, we were at my house watching the big screen TV. My parents were both at work; I'm an only child. Feeling hornier than usual that day, I decided to press my luck and see if Brett would bite on my suggestion. We were watching a baseball game on the cable, since I like the Cubs. Brett was a Brewers fan, coming from Milwaukee. I said, 'let's make this interesting.' 'What'd you have in mind?' he asked. 'Oh, a little strip-baseball,' I joked, watching his reaction. 'How do you play?' he wondered.
'I got the Cubs, you got the Brewskis, everytime your team gets a hit, I have to take off an item. When the Cubs get a hit, you lose some clothes,' I offered, making it up as fast as I could think. 'What happens when someone gets naked?' he asked. 'How 'bout that person has to jack-off while the other guy watches?' I said. Brett thought about it for a few seconds, and then said, 'OK, but we both have to start with the same number of clothing items, and we can never breathe a word of this queer game to anyone, you perv,' he laughed.
We counted clothes, then got our snacks and sat down for the game. After three innings, I still had two items on, my boxers and a sock. Brett was down to his briefs, which I could see were hiding, and not very well, a stiff bone. Top of the 4th, Soriano led off with a hit for Chicago, and Brett groaned 'oh no.' 'A bet's a bet, my friend, pay up,' I gloated. 'Where do you want me to jack off?' he asked. 'Just stand up in front of me and let the cum fall where it may,' I said.
Brett slid off his briefs and out sprang a dark, long dick. I was surprised at how comfortable he seemed in going thru with this little ritual. He looked at me and started pumping his dick, which got me instantly hard. I gave my crotch a squeeze and said, if it helps you, I'll take my boxers off, too. I didn't wait for his answer. I kicked them off and began fondling my balls, alternately looking at Brett's face and hard-on. He was doing the exact same thing.
After about two minutes of stroking, Brett rubbed his free hand thru his pubes and let out a groan, spritzing my chest and face with an unbelievable load of cum. It just kept coming and coming. He squeezed his dick and sighed 'Ahhhhhhh,' then wiped his hand on my leg and sat down beside me. We couldn't help but laugh at the mess he had coated me with. 'Here, let me show you how it's done,' as he brushed my hand away and took hold of my thick member. Now I was was moaning. Brett reached with his other hand and began squeezing my balls, and within seconds I was erupting all over myself, as well.
I think we both felt comfortable knowing that we were tight friends, and that we'd both done something with another guy that we didn't want broadcast around school for the next three years.
'Let's wash this off,' I said, pulling him off the couch. We got into the shower together, and I don't know what it was, the water, the sex, the skin, but when I turned around to face Brett, he put his hand on my lower back and kissed me. Yeah, I kissed him back, and it was a ravenous kiss, too. We stayed in there making out until the water turned lukewarm, then wrapped towels around us and finished watching the game. Since that day, we've never been closer, and I'd be kidding if I said we haven't repeated our little adventure again and again, with more involved than just baseball.