Green’s Dictionary of Slang

(US black) pertaining to the world of pimping.

a.1954		‘Ball of the Freaks’ in D. Wepman et al. Life (1976) 110: Long-Shoe Sam and Cocaine Smitty / Brought a bunch of faggots from New York City.
1979		‘Iceberg Slim’ Airtight Willie and Me 73: I broke the long shoe rules and played peel off stuff with a couple of fellow losers.