My dad (long passed) and my brother. Started on BB guns, went to everything else as quickly as physical size and maturity allowed: single shot shotgun, single shot .22, .38 Special, .45 ACP, double-barreled 12 gauge, 6.5mm Carcarno, 9mm in surplus Astra.
One of the things I enjoy the most is talking to my brother about firearms and shooting. Unfortunately, we're half a country apart. Makes for some memorable range sessions when we do get together...