Our families have been friends for my whole life. But our friendship really flourished when I got into high school and we were on the same swim team. Because he was 2 years older than me, he would drive me every morning. We became my best friend. Dan and I would hang out all the time. I would stay over his house with our other friend, Tim. Dan and I would sleep on his couch in his basement, and Tim would sleep on the ground. I loved his basement. It gave us the security of knowing if his parents were going to intrude. And the fact that we were all boys meant that we had more privacy than normal. During one of the sleepovers our relationship really started escalading.

Dan and I started cuddling, not as if we were a couple, just lying together.. We started watching a movie, and we were lying together. He only had boxers and shorts on. I was wearing shirt, boxers, and shorts. Every couple minutes we would switch positions to get more comfortable. We were lying on our stomachs next to each other. Our feet were behind our bodies, semi-intertwined.

Then, without warning his phone rang, he was texting his girlfriend. Prior to us lying together he had thrown it behind him. He sat up and leaned back to get it. He replied to her message. But he didn’t return to his position next to me. Instead he stayed, leaning up against the back on the couch.

He then made a move, he started tickling my legs, and then he began to move up my leg, nearing my crotch. He would stroke up and down my legs. Our friend, Tim then interrupted his actions, laughing at the movie. We were barely paying attention, but we played along, laughing also. I laid back next to him, on my side. He motioned me to put my head on his peck. i took off my shirt then I laid down, and put my head on his chest, hesitant where to put my hand, I decided in an instant, his other side, just below his nipple. Every so often I would play with his peck, moving my figures and softly, almost unnoticeably squeezing it.

My left arm was on my underside, so I put it across my body. He saw that it was there, and intertwined his fingers with mine. We would stroke each others hands and fingers. Throughout the movie, I would drift in and out of consciences. I would move my hand up my arm up and down his body. By the end of the movie, I was around his waistline of his shorts. They were about an inch above his crotch. I loved how he had no hair on his chest or stomach. It just allowed me to get that much closer to this dick without it being too awkward. By the time the movie ended I had fallen asleep on his chest. 

He awakened me and we laid adjacent to each other, our heads almost touching. I had gotten a text from my sister I unlocked my phone to read it, and it lit up the couch. He was lying there, not asleep, just looking what I was doing. I replied to the text message, then turned it off.

Then we agreed that we weren’t that tired, we began watching videos on my phone. He placed his head right next to mine. I had my arm back around the back of his head, playing with his hair. It was short, and soft, I loved it. I fell asleep soon after, he returned to where he set up his covers.

Early the next morning I awoke to the feeling of something playing with my hand, I had fallen asleep with it above my head. It was Dan, he was holding it, smoothly stroking my palm, and fingers. it was pitch dark, he couldn’t tell that I was awake. But it was at that moment that I could tell that this relationship was going to be something more.