Seems it's usually used for the type of guy who has to have a 'Busa for a first bike and rides around in shorts and no helmet or any gear doing 150 mph blasts in a neighborhood, flip flops on the feet, silly things like that. Basically a dangerous rider to him/herself and others.
That's just what I've gathered from others talking about them, took me a bit to figure it out at first too.
Squid............an idiot you dont want to associate with. He'll wreck his bike and probably take you out with him. You know who they are already, shorts, t shirt, no helmet and a bigger than life ego trying to prove he's always cooler than you. Squid.............also see ASSSHAT, BUTTMUNCH, JACKASS,JAGOFF,DICKHEAD and any others you can think of when he takes you out doing some "way cool" stunt to impress the non riders.
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