Chris and I grew up with each other. We lived in the same neighborhood and hung out with the same kids from about the time we were six. While we were never 'best' friends, we always shared a bond of being just a few weeks apart in age and sexually fascinated with each other's bodies.
There had always been somewhat of a sexual history between Chris and I, nothing too serious, just typical pre-teen fooling around I suppose. There were times when we would watch each other pee outside, hug standing up with boners in the woods, pretend one was the guy and the other was the girl while having 'sex' on my bed, and so forth. However, we reached a new level one early summer day.
It started out with Chris and his younger brother coming over in the afternoon for a sleepover that evening. We had just gotten Crash Bandicoot for PlayStation and played that for a while. At one point, as my brother and his brother were playing the game, I asked Chris, who was sitting in an old but comfortable rocking chair, 'Where to, miss?' (imitating the Jack Dawson line in the then-popular 'Titanic'). He responded, appropriately, 'To the stars!'
I then pulled him over the back of the chair and onto the couch behind us, little to the knowledge of my brother and his brother entrenched in Crash Bandicoot. From there, he proceeded to lay down on the couch and pull me on top of him. As I lay there, somewhat nervous as he pulled me closer, I felt our boners rubbing up against each other, sure signs of young teenage boy lust.
Nothing much came of that, except for some dry humping of his crotch region. It wasn't till a little later when I asked, 'Who wants a massage?', that our sexual relationship would take a big leap. Until this point, I had never truly handled anybody's genitals, be it guy or girl. That was about to change.
As he eagerly laid down on the sofa, I looked into Chris' beaming brown eyes and giddy smile. I knew he was just as excited as me for his 'massage,' and we both knew there was only one bodily region that was going to get that.
For fun, I started off rubbing his chest underneath his T-shirt, being sure to feel his nipples and hairless armpits before running my hands slowly and sensually down to his stomach region. I felt this area for a minute and teased his pubic area by slipping my fingers beneath the waistband on his shorts and boxers. I teased him some more by rubbing my hands along the inside of his thighs around his knees. I was rock hard by this point, and I could tell by the bulge in his mesh shorts that he was too.
After that, Chris pointed eagerly at his pubic region, giving me the unofficial approval to pull down his pants. I happily obliged, slipping his shorts and boxers down just enough so his hard-on would be out in the open. I was stunned with what I saw, a big circumcised penis, about six or so inches long, that didn't have any pubic hair yet and whose head was almost a purple color. I immediately thought that his young dick looked exactly like mine, which turned me on even more.
Once I got over my brief fascination of Chris' boner, I went to work, despite my inexperience in the area of masturbating another guy. I squeezed my hands up and down his shaft, making sure to rub every inch I could as his dick pulsed. I rubbed around the smooth base of his penis, and eventually made my way to his hairless scrotum and balls, in which I played with and even squeezed too tight on one occasion, causing Chris to laugh in horny pain.
Nothing more became of the couch encounter, but he told me then, 'Let's have sex tonight!' I responded, 'Alright,' not really knowing what he meant or how even to have sex, though I supposed it would be fun. We went through the evening doing the typical pre-sleepover things, playing in the field behind my house, having a bonfire, playing manhunt, etc. Before we knew it, it was midnight and time to go to bed.
We got into our sleeping bags on my basement floor with our shirts off. We laid there for a little while talking while our brothers fell asleep. As we laid on our sides facing one another, he eventually pulled down his mesh gym shorts to reveal the stiffy I had felt up just a few hours before. My dick got hard almost instantly as I began to stroke and rub his smooth hard-on and balls. Unlike the earlier occurrence, it was dark now, which gave us the privacy and intimacy to go further than we'd gone earlier.
I leaned over to Chris, put my arm softly on his back and kissed him. To my surprise, he was more than receptive, as we began to make out. My hand rubbed along his back and eventually down to his butt, where I teased his hole and tickled the bottom of his scrotum. As this was going on with my eyes closed, I felt Chris rub his hands along my stomach and then reach into my boxers to grab my dick. At this point, my hard on was as big as it had ever felt, and my horny level was at a new high as we stroked each other's hard ons.
While we were both on the verge of puberty, neither of us had noticeably started, with the exception of increased size of our penises and our balls dropping. I stroked Chris' dick so long that eventually I noticed his breathing deepen and become very passionate sounding, almost like the people I heard on Cinemax having sex. Then, it happened, Chris shot a small load of cum onto my sleeping bag. I was astonished and pleasantly surprised I had made somebody cum. He later told me it was the first orgasm he'd ever had.
We fell asleep that night in the same sleeping bag, both naked lying on top of each other. For two horny young teen boys, it was a dream come true. Fortunately, we've been able to stay friends throughout the years, although no experience will probably ever live up to that night nine years ago.