Green’s Dictionary of Slang

(US black) a sexual athlete.

1934		‘Alabama-Bound’ in Lomax & Lomax Amer. Ballads and Folk Songs 207: Make me drunk ag’in I’m a windin’ ball. [...] If you a married woman, you got no business here, / But if you are single, babe, / Let’s buy some bottled beer.
1941		A. Lomax Mister Jelly Roll (1952) 47: And right there was where I got my new name – Wining Boy [...] footnote: Wining is the term Jelly preferred to Winding, [...] Winding Boy is a bit on the vulgar side. Let’s see – how could I put it – means a fellow that makes good jazz with the women. [Ibid.] 105: All them girls would holler, ‘Listen at Winding Boy!’.