My first time started with a massage. My straight friend and I were watching tv, but I was tired and started to fall asleep on the floor, face down. I was shirtless, and he kept poking me gently in the back from the couch above, trying to get me to stay awake (as young as we were, 2am was far to early to go to sleep). It wasn't working, so he started to move his fingers along my back, rubbing them into my muscles. I told him in a joking manner that it felt good, so he continued. I loved every moment his hand was on my skin, but never thought it would lead to more. Thus, I was shocked when he brushed his hand along my waist band and slid his fingers under them, if only a little bit. I immediately became hard and shuddered at the novel sensation, which he seemed to notice. He continued to move his hand up and down my back, but every time he reached my waist band, he pushed it down a little bit until he ended up caressing my cute-boy bubble butt. At that point, my erect cock was straining against my boxers, and was harder than it had ever been before. Heart racing, I slid my boxers down and silently let him continue. I was in complete extacy. I could not believe that my fantasies were coming true, and nearly came when he rubbed his hand down through my crack and onto my balls. He played with them and then pulled on my arm to turn over. I rolled over and looked at him, but he wouldn't give me eye contact. He just remained facing away and put his hand on my cock. I could tell he was a bit shocked by the size and loved stroking it. I was too when I played with my cock while he was stroking it; my head had never been so full and straining. It was so hard it hurt. I nearly came too, but managed to fight against it. He rolled onto the floor next to me, bringing a blanket, and, still avoiding my gaze, pulled off his boxers until he was completely naked. I grabbed his smaller cock and began working on it like I normally did mine. I had been jerking for a year longer, and was much more skillful at giving him pleasure than he was at giving it to himself. We jerked each other off until he came, and I immediately followed. I never though so much cum could flow from our cocks, but the hot sensation that completely covered my hand said otherwise. My orgasm was just as fantastic. It lasted longer than I thought possible, and I came everywhere until his hand, the blanket, and the floor were soaking wet.
That first time is still one of the best.