3rd or 4th grade (mid 80s) Apple II - can't remember if it was an original or one of the later models - the school had an entire room of them (was a private school)
Dad bought a RadioShack / Tandy TRS-80 shortly around that time - actually did some programming on it, but had no idea that's what I was doing, haha. Programs had to be saved to a casette drive by pressing record on it and running a command on the TRS.
Used mostly Macs in 7th / 8th grade - when asked what to get, teacher recommended a PC, so we did.
Our first real PC was a custom built 486dx33 / 4mb ram / 250mb hard drive / cdrom / 2400 baud modem in '92. Came with DOS 5.2? Think I road that out until Windows 95, upgrading it a few times. Shortly after, got my first job, bought my first PC - Gateway Pentium I think.
Wasn't until an iPod 3rd gen caught my eye did I really look at Apple. Started taking programming seriously with an iBook G4 (might still have it somewhere) > PPC dual 1.6ghz G5 > Intel Mac Core 2 Duo > Macbook Pro Core 2 Duo > multiple Macbook Pro i5's
Had various 386s and 286s come and go from people looking for a buck or 2 for them. I've built them from bare chassis to now just taking a new one from the store and getting back to work.
While I dabbled with VB4 / VC++ on Windows 95 / 98, I don't think I ever took programming seriously until I got my first office job. It was in technical support; I had played with Microsoft Access and building reports; 1 thing led to another and I spent time doing what I was doing in Access as a real program in VB.Net. One thing led to another and I was looking for programming jobs instead of customer support jobs.
I remember not knowing what a config.sys file was or autoexec.bat and bugging the neighbor who was in IT about it for days, haha. Dad brought home a (I think) Pascal book one day and I ran to my brother (we were kids) saying "this is everything I need to make that football game you want" haha. Sure! It's easy to write a video game - just read this book!