Paul, the man who had been mentoring me and teaching me about sex was someone who worked at my school. He wasn't a teacher, but he ran a program there that I was never a part of or anything. I'll probably post more about him down the line. He was pretty important to my sexual development. Anyway, I was not the only young man he mentored, and he enjoyed having me top for the younger boys while he watched.
I began to really enjoy topping too, though I didn't do it nearly as much then as I do now. I decided that I didn't need to top only when Paul told me to, I could seek out opportunities for myself.
One of these opportunities was a boy only slightly younger than me named Damien. I was somewhat poor growing up, but lived in a wealthy area, and Damien's family was one of the wealthiest. They paid for their three story house with two car garage in cash. So what initially attracted me to Damien was his pool and his trampoline.
One day in the fall, when it was still warm out, I was at his house with him and we were both jumping frantically, trying to do tricks but not snap our necks. His parents and sister were out of the house and I had a plan. I knew Damien was gay and that he had done some experimenting with blow jobs, but nothing else. He wasn't one of Paul's boys, just a kid I knew from a grade below me who had done some experimenting and wanted to do more.
In previous conversations I had informed him that I had done more. I told him about Paul (though not who Paul was) and about the other men and boys I had been fucking around with. My stories always made him horny, but we were never alone in a place we could play.
Never until this day, that is.
We got hot and sweaty jumping and decided to jump in his pool to cool off. I had figured this would happen and worn my practice suit for swim team under my shorts. The suit was a rather small speedo. To be fair, my friends were used to seeing me in small swim wear because I didn't have a pair of board shorts that fit me anymore. Still, this was all part of my plan to put on a show for Damien. I had been having sex long enough to know what to do to seduce a man, or in this case, a boy.
He took my lead and stripped to his underwear, which were boxer-briefs, if I remember right, and we both jumped in. We splashed and played and every time I got out of the pool I made sure he saw my ass wrapped in tight spandex or my bulge wet and full. It didn't take long for him to tent out.
But I was a tease. Instead of making my move then, I suggested we jump on the trampoline some more. So we dried off and put our clothes back on and went back to jumping, getting very sweaty again quickly.
We went inside for some drinks and moved to his bedroom where we could sit directly under his air conditioner to cool off. I immediately took my shirt off and he did the same. By this time we both knew where this was going so I leaned over and began to kiss him gently, working slowly to more tongue.
Soon we were naked on his floor and grabbing each other's cock with a deep need. He and I sucked each other for a while and moved to a 69 position. When he had me close I stopped for a break. He looked at me and whispered, "I want you to be my first." I remember that moment perfectly and probably always will. He was so naked and vulnerable in his need as well as his physical body. He wanted it, but he was scared.
Carefully I began to work his ass open the way I had been working my own open for Paul and others. The difference was that every sensation was new for him. Every movement of my fingers made him groan, cry out, or sigh. When we both felt he was ready, we moved to his bed.
With him lying on his stomach, I slowly pushed my way into him, feeling his sphincter opening, inviting me deeper and deeper in. I let him push back slowly and take his time, even though every nerve in my body wanted to push all the way in at once.
When he was used to the feeling, I began to gently fuck him. Back then I was young and my cock had a hair trigger. I think I lasted all of five minutes before I was shooting my load into him, moaning into his back.
When I pulled out, he rolled over and his dick was still rock hard. Holding it, I kissed him deeply then climbed on top of him, positioning my ass over his dick and pressed down, taking his smaller size without too much effort (sorry, but it is true, he had a smaller cock than I had been used to) and rode up and down on him. I did all the work so he could focus on the feelings. If I lasted five minutes, he lasted maybe one before he pushed his body up and I felt his cock firing in my ass. To my surprise, he was very quiet when he came. When he was finished, he collapsed on the bed, so I pulled off and lay beside him.
We finished the day with another dip in the pool, this time naked, followed by jerking each other off while we dried in the sun. I left his house that day feeling great and knowing that I had just opened a brand new door for Damien, and he told me he loved every minute of it.
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