mine:
Who: Dad
Age: 16
Where: Empty Parking lot of Madison Jr. High School, Trumbull, CT
What: 1972 Toyota Corolla
Transmission: Manual, dammit!
He said I did good!
And now I can add Audient Jr’s:
Who: Dad
Age: 16
Where: parking lot outside Dad’s friend Jeff’s woodworking shop, Hopedale MA
What: 2005 Ford Focus Wagon
Transmission: Manual, dammit!
He did good!
yours?
What a coincidence that both fathers were 16 at the time. 
Anyway…
Me, age 15/Dad, age 44
Some sidestreet in south Minneapolis
1964 Chevy Bel Air 283 Powerpack 4-bbl 225 hp
Transmission: 3 on the tree
Some leapfroggin’, but otherwise OK as I remember it
Who: self
Age: 13
Where: Streets of my neighborhood, Highway 50 and surrounding areas
What: 1975 Ferrari 365GT4/BB, “borrowed” from a neighbor while he was on a European vacation.
Transmission: Manual 5-speed
This is the first anybody has ever spoken about it! 
My dad took me to a deserted country gravel road. We went one mile and I never went fast enough to get out of second gear. Kicked up a lot of dust and the gravel kept the wheels from driving straight without a struggle. We went home and my knuckles were still white from the death grip on the steering wheel. I didn’t drive again until the school driver’s ed program started.
That was my son’s first experience. A pal talked him into taking turns with his mother’s minivan. They were pulled over by a cop for going 30 down the freeway and the pal’s parents had to come and drive them home.
Who: friend
Age: 14
Where: Lonely 2 lane in rural Ft. Worth, midnight.
What: 1966 Imapala, 327, “borrowed” from my grandmother while she slept.
Transmission: TurboHydramatic 2 speed