Even though I still consider myself straight, I think about this event many times when I jack off.
Back when I was 14, I invited my cousin Kyle to come over and spend the night. Kyle and I always got along well. He was 13, about 5'6', and had an athletic body for a kid his age; he's a good looking kid. Anyway, before this incident, the only thing we had ever 'done' together was we once jacked off ourselves in my bedroom at night after watching a porno. We didn't touch each other and it was so dark, we couldn't see each others' cocks. Still, I was hoping that this night we could mess around some more.
At about midnight the rest of my family had headed up to bed leaving me and Kyle alone in the family room. We decided to change into our pyjamas (which consisted of boxers and a T-shirt) and started to play some video games. After a while, I asked Kyle if he wanted to go outside and lie down on my hammock for a bit. He said that that sounded like fun.
We headed outside to my rather private backyard and lay down on the hammock in opposite directions so his feet were by my head and visa versa. We started talking about school and girls, and the conversation quickly turned to masturbation. We talked about how we learned about it, the weirdest place we'd ever done it, etc. Then we started talking about body hair and both admitted to shaving our pubes before. Kyle then mentioned how he had a lot of hair on his legs, so I started rubbing his legs to see. He did the same to me. As I got closer and closer to his thigh, I could see two developing bulges in our boxer shorts.
After a while we stopped and just lay there a little longer, our bulges not going away. I then finally asked, 'Hey Kyle, do you want to play truth or dare?' 'Sure,' he answered. After a couple of stupid truths, Kyle finally picked 'Dare.' I dared him to take off his clothes and walk to the corner of my backyard naked. 'Okay,' he said, 'but I might get a boner...' 'That's fine,' I responded. So Kyle stood up and, facing away from me, took off his clothes. Boy, he had the perfect bubble butt. My cock was going crazy. I slowly began to jack myself through my boxers as he walked across my lawn.
He turned around to head back, but, because of the darkness, I still could not see his dick. He quickly jumped back into his boxers and laid back down on the hammock, this time with an even bigger bulge. 'Truth or Dare?' he asked, as he squeezed his cock through his boxers. I picked dare and he dared me to do the same thing. I quickly jumped up, faced away from him, and took off my clothes, my 5 1/2 inch cock jumping to attention. I then began to walk across my backyard, giving my dick a couple of jacks here and there. As I turned back to the hammock, I saw Kyle slowly stroking himself inside his boxers. I quickly put on my clothes again and asked him, 'Hey, do you want to finish this game inside?' He said yes, and we walked back into my family room.
Kyle sat in a chair and I sat on the couch so we were directly across from each other, each slowly stroking our dicks through our boxers. 'Truth or Dare?' I asked again. He picked dare. I dared him to take off his clothes and jack off right in front of me for a whole minute. Without missing a beat he walked over so his crotch was about a foot and a half from my face. In one swift motion he pulled down his boxer shorts, finally revealing his cock.
It was huge, about seven and a half inches, sticking straight out, and as thick as a banana. I gasped and complimented him on his size. He said thanks and began to jack off. I slid down my own boxer shorts and began vigorously jacking off myself. Before I knew it, a minute had passed and he returned back to his chair, not bothering to put back on his boxer shorts. 'I dare you to do the same,' he said. I stood up, walked right over to him, and began jacking my own cock in front of his face for a minute. Watching him stare intently at my cock as he beat himself off made me hornier than ever. After a minute had past I returned back to the couch and took the game to the next step.
'I dare you to jack me off for five seconds.'
He thought about it for a moment as he jacked his own monster and finally said, 'Okay.' He walked over to where I was sitting on the couch, got down on his knees, and proceeded to jack me off. This was the first time anyone else had touched my cock, and I could not believe the pleasure I was feeling. Five seconds ended too quickly though and he headed back to his chair. As I had assumed, he then dared me to jack him off for 10 seconds.
I knelt beside his lap, reached out to his huge penis, and slowly began to jerk him off. Using both hands, I found myself getting hornier and hornier each time I jacked his dick. I must have gone on for about a minute and then I said, 'Why don't we move over to the couch?'
We sat down next to each other on the couch and started jacking each other off. I wish I could remember more details from this moment, but I was so caught up in the moment that all I can remember is the pleasure I felt from him jacking me off and me rubbing his huge cock. I then said, 'Here, let me finish you off.' He took his hand off my dick and I continued to work on his. With my right hand I rubbed the entire length of his cock and with my left I rubbed his inner thighs and played with his balls. For about five minutes I continued until he gasped, 'I'm cumming!' His breathing quickened and he sprayed two hefty squirts of cum on my hands.
I then spread his cum all over my cock and responded said, 'Finish me off.' He reached over and started jacking me again. I could feel the pleasure building up inside of me. I began breathing really heavily and started to moan. Finally I practically yelled, 'I'm gonna cum,' and, sure enough, my jizz began to spray everywhere. It landed all over my chest, my face, and his hands. I was yelling so loudly I can't believe I didn't wake anyone up upstairs. We both sat there for a second, drenched in each others' jizz. 'Have you ever done anything like this before?' I asked him. 'No,' he responded. 'Man, that felt great, though,' I sighed. 'Yes,' he agreed.
We then walked to the bathroom sink, cleaned ourselves off, and proceeded to go to bed. I think we were both a little freaked out over the whole situation to do anything else that night. He has since expressed that, now that he has a girlfriend, he doesn't feel comfortable messing around. Still though, I hope that one day, I can jack off his huge cock again, and maybe we can possibly take things to the next level.