Father is a programmer, so I was always around computers. He taught me how to build my first one around 7.
Never cared for anything IT related till I was around 15 or 16 and started doing LAN parties. Got a job working as an IT tech, did my thing only because I knew it ( same reason why I'm working help desk now -_- )
One day I was in my IT class, and used a netsend command to send messages to hot chicks in the class. Shit was hilarious. Kind of went from there.
My initiation moment was hacking a digital billboard to show the Laughing Man logo - out of curiosity too. Ever since then, blackhat, redhat, greyhat applications has always intrigued me. I've never fully pursued much for fear of legal repercussions. Currently in the process for a security analyst position with a Fortune 15 company. Hopefully something will come of it
Beyond dicking around with Backtrack adn Metaspoit, I have built a PwnPhone - most badass little Nokia N900 evar. I brought it in to work once and forgot to turn off active mode and my manager's machine starts screaming out alerts about a brute force attack, the WEP being cracked, and one server suddenly picked up a rootkit.
Whoops.