The first time I had a wet dream I was 14 and a friend of mine let me borrow an issue of Penthouse from his stack of nudie magazines. Even though I'd never masturbated before I studied all the pictures in that issue because my pubescent mind was starting to really enjoy looking at naked women. That night I remember my dreams being filled with images of beautiful women showing their breasts, asses, and pussies. I woke up in the middle of the night to find that my underwear was soaked. For the first couple of moments I wondered if I'd wet the bed, but I realized that it didn't smell like urine and it was too sticky. Then it hit me that I'd just experienced one of those "wet dreams" they told us about during the sex education class.
My first orgasm while awake happened a few months later. My family had recently gotten dial-up internet access, and after being left home alone one evening I found myself scouring the internet for pictures of naked women. I also found an erotic story archive which I read from with great interest. I had recently discovered just how pleasurable it was to hump my mattress while aroused, and after getting good and turned on by my online porn hunt I proceeded to mattress-hump while thinking of all the things I'd just seen online. Pretty soon I felt a tightness in my balls followed by contractions that were so intense they actually felt kind of painful. I knew right away that I'd just had an orgasm, although because it was something my body wasn't used to at the time my balls felt quite sore afterwards. That didn't stop me from doing it again a few days later, though. Eventually I got to the point where the soreness went away entirely and there was nothing but pleasure.