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I'd say he's to big and spikey so he might tear it, but then again he's worn other articles of clothing. So...yeah that is a good question. Why didn't he get a swimwear look?
It just occurred to me (after 5 years): How come Raph is the only one that didn’t get a swimwear look?!
Spider-Man (Peter Parker) is crazy strong, right?
Poor guy would probably break every stress ball in existence, without even trying.
So, hear me out: Custom made Vibranium stress ball!
He could probably put some kind of slime coating or smth to make sure he doesn’t cut himself on sharp metal, too.
With the added benefit of looking super badass to anybody watching/finding out what it's made of.