Skateboarding is primarily a white person sport. 50 is saying that Wayne is acting like a white boy when they’re bored, going to skate board. And in the case of Lil Wayne skateboarding, it ended up with him getting some stitches.
50 is also asking why are Lil Wayne’s pants so tight.
Well 50 the answer to your question is that the pants he’s wearing are women jeggings.
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