My first handgun was 6in Colt Python. I got it 2 months after I got married in 76. The guy said make him an offer and I said how about a hundred - His answer was THAT MUCH!! I damn near broke mywrist getting the money out of my pocket. Spent the 2 weeks grocery money on it. My wife was a little perturbed, but I still have her and the Python. Which has gained more value then most investments.
I've been thinking what handgun was my first, I think it was a .22 derringer, I was 18, I bought it at a small gun shop, I remember giving the guy $15 and he handed me the gun, (and no, it wasn't Luddco). I didn't shoot it a lot, because I had a Marlin .22 rifle I was trying to wear out. I still have the derringer, just came acrossed it in a box of junk.
Glock 17 3rd Gen with a ghost ring rear sight... got it from a buddy for 250.00 with a bunch of mags, holster, mag holster, and some ammo(still have it)
Jennings 9mm - once upon a time when i knew nothing about guns i paid way too much for an inferior pistol from Don's Guns. I will never go there again.