Silly Bets

I came here just to tell this story. I’ve never told a soul; not even my shrink, but this time of year always brings it back to me in a nagging way.
My mom’s brother (my uncle) had the money in the family. He was in construction and probably other things. His house was the party house for all family events and what seemed like non stop pool parties during the summer. As a kid it was awesome. Tons of stuff to do and drunk parents not really paying attention to anything. They’d get loaded and it would be a sleep over with my cousin “Kevin” who was two months younger than me.
One night the adults had all gone to bed and we knew we probably wouldn’t see them so we decided to do a sneak raid on the kitchen for snacks. One of us decided the tighty whities we slept in were to bright and would make us easy to see so we kicked them off and did our nude kitchen assault running back to his bedroom which was on the third floor on its own.
There in the light we stood nude with our snacks and boners that at that point in time we laughed about. We compared them, surprised at the differences. I was a bit longer. We ate our snacks and went to sleep. The rest of the summer when we’d have our sleep overs were pretty much the same but we were naked a lot. We’d make bets and the loser would have to run out in the back yard naked or dump a glass of ice water on their private parts. Silly stuff.
It seemed like it was just curiosity and I think by the next summer we had discovered girls and that was the end of that.
Flash forward some years later. Kevin and I were both 19. I was in college. He was working for his dad. The family all got together for a Holiday season bash at the uncles. Lots of drinking and lots of laughs. It ended with the old folks crashing and Kevin and I hanging in the basement bar, drinking beer, shooting pool and talking about everything and nothing.
We were laughing about how things never change. The same old drunk arguments between uncles about some football game from 40 years ago. The women huddled together talking about whoever wasn’t there. Kind of comforting really.
Suddenly Kevin says “I know one thing that has changed. You used to be bigger than me but I’ve grown boy. You got nothing on me now.” I laughed it off but he kept going until finally he was trying to bet me $100 that his dick was bigger than mine.
The money kind of pissed me off a bit. I said, “First off you’ll always be the little cousin and second I go to school. I don’t work for daddy. I don’t remember the last time i had $100.”
“Fine” he fired back. “We’ll bet something else.” I told him he was crazy and leaned back down to take another shot on the pool table. He of course questioned my bravery and we were kids all over again.
“So what do you want to bet?” I asked
He leaned back with a devilish grin and said “The loser has to hold the winner’s in their hand for 30 seconds and tell him how beautiful his cock is.” He laughed but I saw he was serious and still feeling the sting of that $100 I said. “You’re on!”
With that we kicked off our pants both rubbing to get maximum size. Well, he sure did grow. He had at least two inches on my maybe 7 inches. Before I could say anything, he said “Pay up.” So there I was naked from the waist down holding my cousins huge cock in my hand and telling him how beautiful it was. I could feel his pulse pounding why I did it. He was loving it.
With the 30 seconds over I let go and said, “Let’s play some pool.” He laughed and took off his shirt. “Going to go for some payback on the table?” he asked. I was pretty pissed and a bit humiliated by then so I said “Sure, what do you want to bet?”
He said, “Its your game. Make the bet.” I figured I’d call his bluff and shut him up. “Loser sucks the winner.” All he said was. “Rack ’em up.” I did and we started the game.
My hand was shaking as I set up for the last shot, “eight ball, top corner” and with the lightest tap it dropped in. He threw his cue down and said fuck a few times. I just said, “Pay up.”
He got down on his knees in front of me looked up and said “just don’t cum in my mouth” and started giving me head. He should have knew better because in no time I was blowing my load in his mouth. He coughed gagged and spit onto the floor, cursing me the whole time. I had to laugh. “Sorry.”
He was having none of it. “Do it again. Same bet!” I said I didn’t think I would be ready again if he lost. He said, “Okay, if I lose I’ll pay you the $100.” I laughed “No thanks.” He countered with “$500, but if you lose you swallow!” What I could do with $500 and I had been out shooting him all night ….. “Rack ’em up.”
My third shot in I chipped the cue ball which slammed the eight ball and I watched it drop, costing me the game in the same exact pocket I had won the last one.
No talking this time. He walked over with a diabolic grin. I got down on my knees and took him into my mouth. If nothing else it gave me an appreciation for what I had put some women through when he grabbed the back of my head and thrust into me till I was gagging. I slapped his hand away then wrapped my hand around the base of his cock to keep him from choking me. I worked the hand and my mouth together. He complimented me on my technique which I could have done without.
Unlike me it was taking him forever. I was doing everything to get him to blow, licking and sucking his balls while stoking him. Then I realized he would get close and pull away a bit. He was really enjoying himself and wanted it to last.
I remembered one thing that has worked for me on occasion and I reached around and gently pushed my finger into his asshole. Almost immediately I felt my mouth fill with the milky fluid. Seemed like a gallon. “Swallow!” He yelled and I choked it down grabbing a bottle of vodka off the bar to wash the taste and maybe the memory away.
He fell back on the sofa with a dazed look in his eyes. “I am wiped out, ” he sighed, “time for me to crash.” I just agreed. He got dressed and went upstairs. I got dressed and crashed on the sofa. It was never mentioned again.
That was 11 years ago. I’m married with a kid. He lives with a girl and they have a kid. We both work for his dad now. The thing is I have never been attracted to men ever. I honestly don’t think he is either. Its not something I would ever do again but for some reason, as I said especially around the holidays I get this sick guilty feeling.
I guess my reason for writing this is to find out if anyone else has had a similar experience.

Leave a Reply

Your email address will not be published. Required fields are marked *