First Apple product I ever used: Apple II and IIe, in high school.
First Apple software I used on a computer I owned: iTunes for Windows. Even though the software was in its infancy, I still preferred this over Musicmatch, Windows Media Player and of course RealPlayer.
First Apple hardware I possessed: An old IIe, given to me by a relative. I kept it around for a few months, but gave it back when the nostalgia factor wore off.
First Apple hardware I purchased: iPod Nano 4Gb 2nd gen, blue. Up to that point, the nano was the most elegant piece of electronic hardware I had ever had. It worked perfectly with my already well-established iTunes for Windows library, no extra configuration needed; this combination led me to investigate getting into the Mac side of things. I'd still be using it today had it not been taken in a burglary.