First experience? When I was about 14, I borrowed one of my dad's (really) neglected pipes, packed it with some of my grandpa's SWR, and tried lighting it with matches. Naturally, a disappointing experience for a kid who had never tried tobacco and thought pipe smoke would taste like it smelled. I had no notion of how to pack, light, or smoke, but I wanted to enjoy it.
Kept up with it for a few months, enough to get the hang of things, but was still looking for a smoother, more satisfying flavor and experience. Plus, I wanted a different style of pipe and wondered if breaking in my own new pipe would produce a better smoke. Bought a Medico (standard smooth billiard) and some Borkum Riff (on the pretext of buying a gift) around the time I turned 15. Breaking in an unsmoked pipe with a different aromatic definitely bumped up my enjoyment a few notches. Didn't look back after my Medico milestone. I loved the flavor and scent of quintissential BR, which I had eventually learned to smoke with proper technique. Also felt comfortable with the look and feel of the classic straight billiard. I "graduated" to higher-quality pipes and blends at college, as most of us do.