This was my first bike, a '66 Bridgestone 50 Sport.

My dad was a mechanic all his life and we had moved off the road to stay put for a while. He was a mechanic for a very large construction company our of Ann Arbor MI back in the late '50s through the early '60s. We move from road building job to the next road building job. I went to 11 different schools before we settled down in our home town area in the middle of my 7th grade.
So to keep me occupied in the summer, we lived on a lake, he got a gas pump and 275 gallon tank from his nephew and put it in down by the lake in front of the house. We built a dock and I started to sell gas on the lake. He bought my first tank and case of oil and then at the end of the summer I paid him back.
Well at the time I didn't realize all the people my folks knew and how many of them wanted my dad to look at their outboards etc. So along with the little gas pump, we had a little building that I stocked spark plugs, some ski ropes and misc items that they could buy from me instead of walking up town to the hardware store.
So after a year of this, the building got bigger and we ended up putting up a building up behind our house on the blacktop road around the lake. This turned eventually into a pretty good size marine business and I was the mechanic. It still amazes me how older people back then would trust their motor etc to a "kid", me. But they knew my dad and that was good enough for them. You would not get away with that today.
Anyway, my cousins that lived out of the village a couple miles had some money and wanted to buy small motorcycles for themselves. So my dad took on Bridgestone bikes and he had to buy four I believe to get the dealership. A 60 Sport went to one cousin and to his brother went a 90 Trail with dual rear sprockets... I only had the 50 Sport as a demo and didn't really get to do with it what I wanted, but hey, I was riding and only 15. We eventually sold Johnson, Mercury, Artic Cat, Polaris, Crest pontoons, and a bunch of other stuff.
So the 50 Sport was my start. We didn't have a lot of money and I was always wheeling and dealing to get bikes of some sort. I'm still doing the same thing.

My first Harley came when I was about 18.

This was a '56 KH. The H I believe was the stroker motor with a 3/4" longer stroke than the stock 750 flathead. I paid $50 for this and that was a LOT of money to me.
Hope I didn't bore you all with my ramblings.