Started with Paint, then Microsoft PowerPoint (yes, really), and then found AutoRealm, which I only used a couple times and just didn't like. Got turned on to Dundjinni 5 or 6 years ago and used that exclusively for a couple years, then started to do post-Dundjinni work in GIMP (which I initially used just for photo retouching), and now use GIMP almost exclusively.
I used to use a mouse. Then I got a Bamboo Fun for Christmas, which I used for almost a year before my toddler got a hold of the pen and broke it. Desktop's in storage, so I'm relegated to my netbook (temporary housing necessity) and the touchpad, which sucks, or a mouse if I can swipe my wife's from time to time. I will gladly purchase another Bamboo when I can scrape the money together.