Theres a long discussion of the provencance of Winding Boy in Mr Jelly Roll Jelly Roll talking his reminisences to John Lomax. Jelly Roll said he was called Winin' Boy - on acoount of him liking fine wines. The general consensus however was that Whinin' Boy was some sort of slang for pimp.

In fact, viewed dispassionately - rather like Pretty Baby - its graphic message from inside the sex industry.

I first heard the song playing in trad. jazz band, but Ian Buchanan's masterly guitar/vocal version on the Blues Project sampler album followed soon afterwards.

I put the song on my first cd -St Peter and John Dillinger. The sleeve notes for that and on other songs are on this page:-
http://bigalwhittle.co.uk/id1.html