Colt 1911 when I was 18 years old. The next one up was a beautiful Belgium made Browning Hi-Power. I sold both over the years as I thought I wanted something else... the then new "wonder 9's" were all the rage back then. I wish I still had them, especially that old Browning Hi-Power.
My first was a Sig P228 9 mm. I bought it used from a police sale and it was nice. It looked like it had only been used to qualify. Too bad it was stolen by my nephew I was trying to help (the little bassturd). I liked it but after running a 1911 for a while, I won't be going back to the Sig.
Glock 17 pre Mag Ban, about 14 years ago? Only came with one 17 round mag. I think the dealer removed, and sold the 2nd one. At the time they were going for over $100.00
S&W Mod 28 Highway Patrolman .357 Magnum. Had to have my mom sign for it at Windsor Gun in 1974 I believe. Joined the Navy later that year on my birthday.