This is the first time I ever jacked off to an orgasm.
Unlike many of the stories here that I've read, I am not one of those that 'have been masturbating for as long as I can remember.' I may have gotten some small pleasure from bumping up against objects like the floor or the couch edge when I was a younger kid, but if I did, it definitely wasn't anything I committed to memory or ended up persuing. I remember really well the first time I actually conciously jacked myself off. Back about 5 years ago, halfway through sixth grade, I remember beginning to wake up with erections. At first I was a little curious, but that didn't last. Normally, I'd simply wake up, take a shower and by the time I was out my dick had gone down to normal and I'd totally forgotten about it till the next morning. Fast forward to the first or second week of summer vacation after the end of sixth grade, though, and there was the morning that I first experienced the great sexual pleasure of jacking off.
I had then recently turned twelve years old, and I woke up, as usual, with a hard on, but this one was different. It was a hell of a lot bigger and stiffer than usual, and the veins were throbbing. I was a little weirded out but tried to do as usual, taking a shower. I stepped out of the shower and dried off, but interestingly my dick was still hard as ever. I wasn't totally sure what to do about it, the thing would not go down. I sat down against the wall of my room, looked at it for a few seconds, then I touched it. I remember how mind-blowingly sensitive it felt when I touched it like that. I kind of liked the sensitivity, it felt really weird but kinda cool, so with the four fingers of my hand I rubbed my dick's underside.
This felt amazing. I remember gasping sharply at the sudden pleasure I felt. I was thoroughly wierded out at this point, my 12 year old self wasn't sure what masturbation was, or what this great feeling was, only that it was amazing and probably related somehow to sex, so I thought what the hell. I clasped my whole hand around my cock and started pumping it up and down, it felt great. Within a couple minutes, my breathing was getting shallower and shallower, and I was wondering how or when the great feelings were going to end.
Finally, after a few minutes, my gasping was at its shallowest, my free hand was gripping the carpet, and every muscle in my body clenched up hard as I involuntarily groaned out loud, coming in the intense pleasure of my first orgasm. I was totally amazed, but wierded out once more by my cum. I pretty quickly figured that's what gets a girl pregnant, however, and for the next week or so, I was totally preoccupied by jacking off.