This site is amazing!
Back when I was fourteen I had a mate stay round my house, let's call him Richard (he's quite fit!). He had been acting a bit funny in the months leading up. We were always play fighting and touching each other for periods of time that were longer than necessary, which was noticed by some people in my school, but not enough to convince me that he was up for anything sexual.
Anyway, it came to about 11:30pm and we decided that it was getting late, due to the fact that we did not want to be tired for our day of water-skiing and wakeboarding the next day (hence the reason why he was staying). We got changed in separate rooms, into our boxers, I got into my bed and he laid on the floor next to me under a quilt. We started chatting a bit and to enable us to speak quietly I got out of my bed and laid on the floor next to him (that was my excuse anyway!). I had left my pillow on my bed so I asked Richard if I could use his stomach as a pillow. He agreed and so I rested my head on his flat stomach and we carried on chatting.
A little later in the night I rolled over onto my stomach, so that I was sleeping kind of on top of him. He didn't seem to mind, so I tried to see how far I could push him. I slowly reached over and rested my hand on his tight arse; he didn't budge so I started stroking him up and down his arse crack. He seemed to be enjoying this quite a lot, so I slowly but surely progressed down his boxers, so that I could stroke down his inner thigh.
After about ten minutes of this he rolled over onto his front, and I softly started running my hand up and down his leg (outside his clothing). I could see in the faint light that he was smiling, a good sign. I rested my hand where his cock was, and felt that he was rock hard. I rolled my leg on top of his crotch and started to grind up and down his penis, really slowly. I then slid my hand down his boxers, and grabbed his cock in my hand. If any of you have done this, you'll know that this is the best feeling in the world (bar the other way round!). I started jacking him off, increasing my pace little by little.
He suddenly 'came awake' and reached for my boxers where he found my five and a half inch cock (reasonable for 14yrs, his was about four and a half) as erect as it had ever been before. He started wanking me really fast, which felt amazing. About 25 seconds later he started to wriggle around, he let out a huge moan, arched his back and came everywhere. The sights and sounds of this put me straight into climax, and I had the most amazing orgasm ever. We cleaned ourselves up and went to sleep, never to mention it again.
Hope you enjoyed my story, I certainly did! Got to go now, I'm about to cum myself; this site is wicked by the way!