Jacking off (masturbating) to someone of red hair, more commonly gingers.
Suppose your having a sleepover, and your red-headed friend is in the bathroom.
Guy 1: dude, is he in the bathroom?
Guy 2: yeah, he's probably 44ing to himself
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Guy 1: is that a playboy?
Guy 2: yeah, redhead addition. i'm doing some 44 tonight!
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