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Tim was a neighbor of mine many years ago. I felt sympathy for him and his brother because their father abandoned them and left the mother to care for two young men. Tim came over often to play games like dart board, pool, and sometimes to wrestle. I was a high school wrestler and liked to keep my skills up. Tim had just graduated from high school and was a wrestler.

One Friday night, Tim asked to spend the weekend and I asked his mother if that was alright. She was always fine with having me take Tim since I would often wash his clothes, take him shopping and getting him needed things. His mom was barely making a living and her ex had failed to pay child support. Consequently, the boys often had dirty clothes and worn out clothes. I would buy him things since I was single and doing well money wise. So, we started wrestling in the living room and it was a hot day with no air conditioning in the house. We soon were quite sweaty. We took off our shirts and shoes and socks. We only had on our shorts. I had never had sex with Tim as I felt more like a father figure and did not want to add sex to the equation, although I was physically attracted to him. Tim had started developing nice arm muscles and a 6 pack stomach. He liked to show me and often times took off his shirt and pants so I could wash them. He would walk around the house in his underwear which drove me crazy. So, this night turned interesting when we began to wrestle. He stopped and said we should make this a contest. The winner of the wrestling match would be jacked off by the other. I asked him if he was sure about that. He said sure and then pointed down to the large lump in his pants. I nearly fainted when I saw the outline of his cock and the tip poking out the top of his tight fitting underpants. OMG. I had never seen him get hard before so my blood pressure went sky high and I too got quite hard.

As we wrestled I could tell he was deliberately letting me win. I ended up on top of him with our cocks pushing against each other through our pants. I tried to feel his cock with my hands and he stopped me. We wrestled some more and I pinned him again. This time he said let's go upstairs and jack you off. OMG. SO, I asked him if he really wanted to have this happen since this would change our relationship. He said he had wanted to have sex with me since he found out I was gay. He had found a gay magazine under my bed once and asked me about it. He admitted he was bi-sexual like his mom. Interesting.

So, we went upstairs and I got some lube. I lid down and he got on top of me facing backward. He lubed me up and jacked me off. I rubbed his back and rear end. When I shot my load it sprayed everywhere and hit him in the chin. He laughed. He cleaned up by wiping my cum on his pants. We then moved to the bed as I offered to jack him off. When he got on the bed, he lay there in his tight underwear. I just sat alongside him and just smelled his crotch area and felt his cock for the first time. It was magical and delightful. I slid his underpants down and took in the glorious beauty of his young cock which was dripping with pre-cum. He wanted me to suck him but I was nervous and told him next time. It did not take long for him to start breathing heavy once I started lubing him up and jacking his cock. Semen spurted everywhere and I loved it. I cleaned him up and he got dressed and left.

Thus our relationship became one of sex buddies. He would end up fucking me, having me try to fuck him although he was really tight and he decided to let me use my fingers in his ass instead. I recall the first time I sucked him and inserted fingers in his ass to massage him prostate. He became rock hard in my mouth and then shot a load like never before. Incredible.

More chapters to come as this went on for 5 years until I moved away and he moved in with. girl friend.