Green’s Dictionary of Slang

1. a clever, cunning person [they are ‘sharp as a whip’].

1590		R. Harvey Plaine Percevall (1860) 9: They had neede be large long Spoons (say you) if I come to feed with such whipsters.
1656		R. Fletcher trans. Martiall his Epigrams VII No. 29 64: From Memphis comes a whipster unto thee, And a Black Indian from the Red Sea.
1667		Dryden Sir Martin Mar-all IV i: There were those that would have made bold with Mistriss Bride; an’ if she had stirr’d out of Doors, there were Whipsters abroad i’faith, Padders of Maiden-heads, that would have truss’d her up, and pick’d the Lock of her Affections.
1672		M. Atkins Cataplus 25: This whipster had a plaguy knack / At trumpet blowing and horn-crack.
1697		Vanbrugh Provoked Wife V i: My innocent lady, to wriggle herself out at the back door of the business, turns marriage bawd to her niece, and resolves to deliver up her fair body to be tumbled and mumbled by that young liqourish whipster.
1715		‘Nickydemus Ninnyhammer’ Homer in a nut-shell 68: But yet could get no tare or tyding, / Where the young Whipster was abiding.
1725		New Canting Dict.
1785, 1788, 1796		Grose Classical Dict. of the Vulgar Tongue.
1811		Lex. Balatronicum.
1823		Egan Grose’s Classical Dict. of the Vulgar Tongue.
1836		Hereford Times 11 June 3/1: Our skin can never be injured to the extent of a scratch by the finger of such a whipster.
1843		Devizes & Wilts. Gaz, 10 Aug. 1/3: Our swaggering whipster might attempt to exercise his threat.
1859		Matsell Vocabulum.
1895		Crowe Aus. Sl. Dict. 94: Whipster, a cunning fellow; a sharper.

2. (Irish) a forward, impudent woman, also occas. a man [whip v.¹ (1) as they are inclined to steal].

1910		P.W. Joyce Eng. As We Speak It In Ireland (1979) 349: Whipster; a bold forward romping impudent girl.
1918		K.F. Purdon Dinny on the Doorstep 35: He had enough to do, without having to argufy with two young whipsthers like that.
1920		S. O’Kelly Leprechaun of Kilmeen 50: It’s that whipster Maura Lally that’s on for the ruination of him!
1948		P. Kavanagh Tarry Flynn (1965) 13: Not that I care a straw for that whipster of Reilly’s – a big-faced stuck-up thing.
1952		B. MacMahon Children of the Rainbow 197: Mean, lousy dirty, impoverished Cloone! Burrow for wren-boys, spree-boys, rakes, rapsters, whipsters, mummers, flagwallopers and poachers!