I have owned and shot handguns since the age of nine, but of course they were gifts from my father.
The first handgun I bought with my own money was a Ruger Old Army. Why ? Because I wanted to buy a new handgun and I wasn't old enough to buy a cartridge handgun (I think I was 18 years old at the time). I always liked black powder and spent several years enjoying the Old Army.
The first cartridge handgun I ever bought on my own was on my 21st birthday. It was a Raven in .25 ACP. The reason was that I was going to school and working for minimum wage. I didn't have much money and wanted to exercise my "right" to buy a handgun. Growing up, I had seen plenty of small hideout type handguns on TV, but had never actually fired one, or even held one. So, I didn't just settle for the Raven, I was actually excited about it. I have told this story before, but... Since personal use of the internet wasn't around back then, I didn't know the Raven was a POS. So, I enthusiastically shot it, and even refinished the stocks and bought an outside the belt holster for it. When I eventually sold it, I was completely content with it's quality, accuracy, and reliability of function. I was far from enthusiastic about the performance of the ammunition.
Last summer I came across the identical gun, used, at a store and purchased it for old time's sake. I haven't gotten around to actually firing it at this point and probably won't.
The first handgun I ever owned period was a Ruger Standard Model .22 autoloader that my dad purchased for me at a gun show for $50. He also owned a S&W Model 17 which I got to shoot. Contrary to what the libs would have you believe, none of them ever got up and shot someone on their own, and dispite the fact that I was nine years old at the time, I never shot anyone, never had an accident with them, and never destroyed someone elses property with them. I still own the Model 17 along with a duplicate I bought recently. I still own a Ruger Standard Model although my first one is long gone.
