Getting the nerve to ask for it from a teen guy.
When growing up I had jacked-off with my neighborhood friends out in the woods or at our houses when we were all alone. It was the natural thing to do when hormones were raging. One friend was special to me however.
When we had gone through puberty and our cocks had grown bigger I began wanting to jack another guy to see how it felt. One day at my good friend's house we were naked and stroking our cocks when I asked if he would let me stroke him. He was fine with it and after doing it awhile I lowered my mouth over his cock and began sucking it. He loved it and came in my mouth after a bit and asked if I'd like mine sucked off. I did, and he sucked my cock til I came in his mouth.
Fast forward 6-8 months and he wanted me to stick my cock in his ass. No problem as I was very horny. I lubed up and buried my length into him and began pumping his ass until I came in torrents. I thought about it and asked if he wanted to stick his cock in my ass. He also did and lubed up. His cock was much thicker than mine and he slowly inserted it and began humping to get it all in. Wow! I was about split in half but endured his width until he came in me.
We had sex at his folks place for over 2 years until we moved on to having sex with girls. I'll never forget the great sex we had at his house.