This thread reminds me of the first time I saw a longboarder.
I was maybe 10 years old. This was ~2000 so they weren't as omnipresent as today.
Anyway, I was practicing my ollies and shuv its on a tennis court by the high school when some older boys cruise by on some biiiiig fat longboys. Phish shirts and flip flops but still jocks. Probably played lacrosse. You know the type.
I watched them cruise in circles and practice slides for a while, perplexed at the sight of their fat-wheeled, concave-lacking behemoths.
They eventually stopped cruising to play a game of hackey sack and I took the opportunity to approach them to ask them why their boards were so big.
The lead boy (and best hackey sacker) laughed and told me "The bigger your dick, the bigger the board."
I left the tennis courts feeling confused and slightly insulted
True story