Two first's.
First one I played was my parent's Harmony acoustic archtop with f-holes, probably made in the mid-sixties. They still have it.
Action is fairly high, and I remember as a little kid that the strings hurt my soft little fingers.
Recently I restrung it (probably first new strings in 25 years) with light d'Addario PB's, and it actually sounds pretty nice.
First guitar I bought was a Peavey T15, not sure but probably made in the '80's. Was a 3/4 size (I think), had a blackish (maybe a hint of super dark green?) and a whitish pickguard, reminiscent of a Tele. Got it for about $100, sold it a few years later when my interests wandered. Don't really miss it, although now I regret not keeping up with guitar back then.
When I 'restarted' I began messing around with a Strat, then became more of an acoustic guy and have been playing my brother's awful Norma dreadnought. Warped neck, action super high, thin tone. But, it got me motivated to seek out a better guitar and become a better player.
I graduated to Taylor's only a few months ago, had a GC5 for a bit, but was unsatisfied with the bottom end and now have the GSLJ (~610).
So, that's my guitar journey thus far.
Of course, now I'm already flirting with another Taylor. The GSLJ will stay, it may just gain a roommate.
-K