Derek and I began masturbating together. One occasion I remember happened during the summer after we had started. Derek and I had birthdays that are pretty close together, his in late May and mine in early June. So one day in early June, a few days after my birthday, Derek stayed the night at my house. We spent the beginning of the night with my brothers, watching TV and eating, whatever. Then when midnight rolled around our parents told everyone to go to bed. Derek was going to sleep in the basement and no one else wanted to, so I said I would sleep down there with him too. My basement had a huge V-shaped couch along one wall and a big-screen TV on the opposite wall. We played a baseball game on the PS2 hooked up to that TV and after much trash talking, we decided to make it interesting. "If I win," he said, "you have to suck my dick." We laughed at this because it was obviously a joke, but there was a hint of anxiety behind the laughter. Did he really mean it? "Okay," I replied, "and if I win you have to suck mine." We laughed again. "Deal. Get ready to suck some cock."
We played on for the next few innings and I ended up losing. He boasted and jeered at me while I sat there and just took it. What else could I do? Then he did something I didn't expect. He pulled down his pants and revealed his soft penis. "What are you doing?" I said, surprised, but not upset. "We had a deal," he reminded me a little nervously. "I don't wanna suck your cock." "You lost. So you have to do it." It went on like that for a little bit until I finally caved. "But you have to suck mine too," I said. He consented and eagerly sat down to prepare himself for what I assume to be his first blowjob. Of course, it wasn't a real one. We decided that we would only suck for ten seconds. That's how I found myself on my knees, staring at my friend's four-inch erection, standing straight into the air like a short flag pole. "Do it!" he prodded me.
I took a deep breath and inched my face closer to his penis. Then I gathered my courage and opened my mouth for his member. It wasn't actually that bad. His dick was so small that I could fit almost the whole thing in my mouth. The taste was rather unpleasant though, like a mixture of sweat and old lotion, but I manned up and moved my head up and down a little until the ten seconds were up.
"My turn!" I said, spitting out a cock. We quickly switched spots and I pulled down my pants to free my already hard five-incher, slapping against my navel. He took his time as I had done but finally did it too. It wasn't that great. Actually, I didn't really like it at all. It gave me almost no pleasure and I'm pretty sure his teeth scraped my head once. After the ten seconds were up he spit me out and we just sort of sat there with our pants off. "You know," he said slyly, "you never gave me a birthday present." I could see where this was going and it made my dick throb a little. "You never gave me one either," I reminded him. "How 'bout we give each other handjobs as gifts," he suggested.
I happily agreed and he pulled a bottle of lotion he had in his backpack out. It was decided that I would receive first, so I took off the rest of my clothes and sat with my hands behind my head, ready for his hand to get me off. He lubed up his hand and spread it on my dick and I about came right there. I told him to go slow though so that I could enjoy it longer than I had before. He slid his hand up and down my shaft, focusing on the head as he reached the tip, and I forgot my name it felt so good. He stroked a litle more and then he started to lightly rub my balls too. This was too much and I told him I was about to cum. Then I let loose a few streams of cum that hit me in the chest as I groaned and twitched, his hand still stroking. He pumped the last of the juice out of my tender dick and threw me a towel to clean up.
Without a word, I cleaned up and grabbed the lotion while he got himself comfortable on the couch. He kept his shirt on (I think 'cause he was a little self-concious about his weight) but threw his shorts off into the middle of the room. I grabbed his dick and began to jerk him off. I tried to do it all slow and light like I do it, but he told me to squeeze tighter and to go faster, so I did. The problem was that I couldn't get him to cum. I must have stroked for like ten minutes, squeezing the head and rubbing his ballsack, until he finally said that he was gonna cum. He took his dick in his own hand and rubbed furiously until he noislessly dribbled his cum into his hand. I gave him the towel to clean up, we dressed, and then went to sleep. That wager of the loser sucking dick kind of became a regulart thing for us to do when we were alone, and I intend to tell you about other times it happened in another story.