A loaner weapon from my Uncle. M1911. Later, he loaned me his M9. He had some cool Class III stuff he would also share from time to time. Now he keeps a close eye on me for some unknown reason.
Ruger P95DC. I just turned 21 and there was a shop with a small range down the road where I was working at the time. Great gun. I don't think I ever had a failure with it. It just sits in the safe now though.
My Dad gave me my first handgun at 14 so I could "protect" the salvage yard when he wasn't there. .25 Raven Arms. Guess he doesn't like me very much. That was 20 years ago, I still have it, but have not put a round through it in 15 years.
AMT 45 longslide back in the 80s. it was also my son's first as I passed it along to him. who knows, maybe it will start a family tradition and my great great grandson will be carrying it.