My first was my 1942 "45" I bought in 1955. I was a freshman in high school, and as soon as the previous owner delivered it to the house, I jumped on and rode off. Wish I still had it.
First one I rode was a buddy's chopper in 1971. Sometimes it would go for several miles without breaking down.
First one I owned was a 1987 Sporty 883. It never broke down.
My '07 Superglide Custom. My first Harley and my first own bike ever (third bike considering the two I rode during training course to get a licence).
Yes, I'm a rookie.
First Harley i ever rode belonged to my cousin, it was back in 82, and all i know about it is that it was a homebuilt hardtail, with a 1200 Shovel, suicide shift and had ape hangers on it. it was a pretty cool ride, but it just beat the living snot out of you.