This happened a few years ago when my friend and I were 15, sophomores in high school. I started masturbating when I was around 11 and always wanted to do it with a partner. I had been very good friends with Kyle (not his real name) for about five years when this happened. We always talked about sex and jacking off, but never did anything with each other until this night.
One Saturday I headed over to Kyle's house for a usual weekend sleepover. When I arrived his parents said they were on their way out and wouldn't be home until past midnight, and his sister was spending the night at a friend's house. We started out doing the usual, we played video games and then watched a movie. One particular scene in the movie was pretty hot, I had a sizeable bulge in my pants and noticed Kyle did as well. I then mentioned how I would love to have sex with the actress in the movie. Kyle said, 'Yea but I bet you don't have a big enough cock to please her.'
So I shot back, 'Like you do?'
He smiled and said, 'Let's measure to see who's bigger.' He ran up stairs and grabbed a ruler. When he came back down he said he would measure first and turned his back to me and declared he was 7.5 in. I called BS and said I should measure him just to make sure. At his point I was fully hard and aching to stroke my cock and when Kyle turned around I could tell he was too.
I took his cock in my hand and felt it jump, it was so hard. This was the first time I ever touched another guy's dick other than my own and I was definitely enjoying it, and so was Kyle. I knelt down and placed the ruler next to his cock and measured 6.5 in. 'Liar,' I said laughing.
Then he said, 'Fine, let's see how big you are.' He undid my jeans and slid them around my ankles and measured my throbbing dick to be 6 in. When he touched my dick I got very excited and began to wonder where this was headed. 'Almost as big as me,' he said and he playfully gave my cock a tug.
I went to pull up my pants when he touched my arm and shook his head. I looked at him questioningly and then he asked THE question, had I ever jacked off with another guy. I nervously said no and he said he never had either. He asked if I wanted to right now, and I agreed. We both are both straight and have had girlfriends but decided this was solely for pleasure.
He was still eye level with my cock and the sight of my dick so close to his face was getting me so horny. He looked up at me as if to get an O.K. and I nodded at him. He reached out and lightly touched my cock, he massaged it at first before taking a firm grip at the base and slowly milking my dick up and down. I was in heaven. He used his other hand to lightly tickle my balls as he began to increase the speed, my cock made squelching noises with all the pre cum oozing from the tip. After about five minutes when I was about to cum I stopped him and told him it was his turn.
I sat him on the couch and knelt in between his legs to get full access to his cock. I wrapped my hand around it and started to stroke very slowly, teasing him as he moaned. I started to increase my speed using two hands and rubbing his balls. He told me to stop right before he came and we ran up to his room to get lube and finish off.
We decided to put porn on his computer while we finished, but neither of us paid much attention to it. We got on his bed and sat facing each other, our legs overlapping so our cocks were almost touching. He squirted the lube all over our cocks and rubbed it in. Then we each took hold of the other's cock and began pumping as fast as we could. Within 30 seconds we were both about to cum and we both let out loud moans as cum spurted everywhere. We both lay back smiling and agreed that that was incredible. Then we cleaned up and went to bed like nothing happened
This was the first of many mutuals I had with Kyle and we continued it all through high school. Although, when either of us had a girlfriend it didn't happen often or at all. We eventually progressed to a little more adventurous things, but maybe that is for another site.