Green’s Dictionary of Slang

1. one who is retreating or leaving; an absconder.

1909		J. Ware Passing Eng. of the Victorian Era 225/2: Skipper (Criminal, 1870). One retreating.
1935		A.J. Pollock Und. Speaks n.p.: Skipper, a hotel defrauder who registers, has a bag, remains a few days and then leaves without paying his bill.
1936		Bath Chron. 24 Dec. 11/1: We must do a skipper next Monday night, old son.

2. a young woman, esp. promiscuous and under the age of consent [SE skip, i.e. from partner to partner].

2000

Ebonics Primer at www.dolemite.com 🌐 skipper Definition: a girl who is under the age of 18. Example: Yo remember that ho I fucked las week? Man, I woulda neva thought that bitch was a skipper, now her mama tryin to press charges an shit.