Green’s Dictionary of Slang

four-eleven-forty-four n.

also 4-11-44
[a ‘lucky number’ popularized by numbers, the n. or policy n. bettors from late 19C+, and known in numbers’ jargon as the fancy gal roll or the Washerwoman’s Number; note 1872 The Galaxy (NY) 495: ‘Sometimes a mania seizes the entire fraternity of colored players to play some particular “flat gig,” which is generally 4—11—44, and the numbers being sure to be drawn only after everybody has been tired out and quit betting on them, their appearance evokes a storm that is comical in its intensity when its occasion is remembered.’]

(US black) the penis.

[[US]Criminal Life (NY) 19 Dec. n.p.: James Brennan (4-11-44), [...] Jew Smidt and a few others].
[[US]Nat. Police Gaz. (NY) 15 Nov. 14: When 4-11-44 comes out, and it does about once a year, Africa goes on a drunk].
S. Call Barrelhouse Dict. 95: 4-11-44 surfaced as a black term for penis.