This lead to years of pleasure with my best friend.
Back when I was in high school, I use to have my best friend Rob sleep over at my house from time to time. We'd usually get up early the next morning and go fishing at the nearby lake. Rob and I use to talk about everything, especially girls.
Well, this one sleep over was very different. My parents had a business weekend away and they put my brother in charge of watching me for the weekend. My brother is five years older than me, and although he wasn't thrilled at doing this, he didn't have a choice. That night he decided that he was going to have his girlfriend over and he made me promise to keep it a secret. Although I knew he was having sex with her, he never really elaborated.
That night when he thought Rob and I were asleep, I heard faint moaning and I got up to investigate. I went out to the hall and I could see that the door to his room was ajar, and the lights were on. I could see my brother's head between her thighs. They were both naked. Before I knew it Rob was beside me and we both watched. I could see from the light through the door that Rob had a hard-on and I imagined he could see mine.
When we went back to my room we both wanted to talk about what we saw, so we sat on my bed and whispered quietly. I could sense that Rob had his hand in his crotch while we were talking and I asked him if he was doing what I thought he was doing. He said yes, he just couldn't help it. He asked me how I was doing and I said I was doing pretty good. It was then that I felt his hand slide up my leg to my underwear and he felt my very erect penis. I couldn't help let a slight moan slip out. Before I knew it we were jerking each other off. I always liked solo masturbation but this was so much better.
We did this throughout high school. We kept this our little secret to this day.