Let's see, I got a small purple tricycle handed down from my older sister...
Then a girl's 24" balloon tire monstrosity, also a hand-me-down from my older sister.
Let's see, I started riding my parent's late '50s J.C. Higgins (Sears) three speed 'English racers' until I got my own Sears 26" boy's 3-speed for my 12th birthday.
At almost 16, the frame broke on the 3-speed after I hit a frozen snow pile while on my way home from school. I had to ride to swim practice and be in the pool at the YMCA at 6am, then to school at 8, then home after school). Had it welded, but it broke again a week later...
That led to my first 10-speed for my 16th birthday (no car for me, HA!), a '74 Fuji 'Special Tourer'
That one got stolen three months later from the high school bike rack. Replaced with the identical Fuji 'Special Tourer'
When I got to Ohio State, my one roommate was into cycling and had a Viscount Pro (with death fork, but we didn't know that at the time, LOL), and so were a few of the other guys in the dorm (one Paramount, one Raleigh Super Course). My other dorm roommie and I couldn't keep up, and after riding one of the dorm-mate's better bikes, I sold my Special Tourer to the older sister of one of my high school buddies and got my Fuji S-10S, and my other roommate got a Viscount GP.
I still have the S-10S, but it has been upgraded over the years so there are almost no original components except the frame, handlebar & stem, and saddle.