Green’s Dictionary of Slang

1. to infect with venereal disease.

c.1580		‘I.T.’ Grim The Collier of Croydon V i: She hath pepper’d me, I feel it work, My Teeth are loose, and my Belly swell’d, My Entrails burn with such distemper’d heat.
1611		Davies of Hereford Scourge of Folly 139: Phrina (hot whoore) takes Pepper in the Nose, Because her Noses Pimples some call Poxes, Wherewith she peppers both her friends and foes; So, makes her Nose and Poope, two Pepper-boxes.
1630		J. Taylor ‘A Bawd’ in Works (1869) II 97: She is able to Pepper as many as have any dealing with her.
1660		‘Peter Aretine’ Strange and True Newes 2: Being terribly Pepered with the French pox.
c.1700		London-Bawd (1705) 58: Having so pepper’d him with the Pox, that in a little time he was neither able to go nor stand.
1723		Present State of Russia I 277: A Woman of the Town [...] having peppered some hundreds of the Preobrazinsky Guards [OED].
1733		Laugh and Be Fat 87: She could not sleep for laughing in her Sleeve, to think how she had pepper’d off the Spark.
1772		Bridges Burlesque Homer (3rd edn) 34: So sure this God, for rage or fun / Has pepper’d every mother’s son.
1797		Bridges Burlesque Homer (4th edn) I 47: This god, for rage or fun, / Has pepper’d ev’ry mother’s son.

2. to hit hard; to shoot dead.

1589		Nashe Pasquil’s Returne in Works I (1883–4) 97: That’s a bragge Marforius: yet if there be any such [...] I wyll picke out a time to pepper them.
1631		H. Chettle Tragedy of Hoffman III G: If I pepper him not, say I am not worthy to be cald a Duke, but a drawlatch.
1640		‘Mary Tattle-well’ Womens sharpe revenge 191 I have heard some to brag, as he payd one, hee pepperd another, hee sawced a third, he anointed a fourth, hee scowred a fifth.
1742		Fielding Joseph Andrews (1954) I 82: I’ll pepper you better than ever you was peppered by Jenny Bouncer.
1764		K. O’Hara Midas III ii: I warrant we pepper his jacket.
1775		in F. Moore Songs and Ballads of the Amer. Revolution (1855) 93: How they powder’d your pums, / And all the way home how they pepper’d your ----.
1789		Both Sides of the Gutter part II 16: I have led my ragamuffins where they have been pepper’d.
1797		Bridges Burlesque Homer (4th edn) II 298: The Greek their noddles peppers, / Till down they dropp’d upon their kneppers.
1833		M. Scott Tom Cringle’s Log (1862) 11: The French [are] sufficiently strong to pepper us very decently in the outgoing.
1841		Comic Almanack Aug. 278: Sum got Pepprd by the John Dams.
1841		True Flash (NY) 4 Dec. n.p.: [P]eppering away right and left, bored him to the ropes.
1848		Bell’s Life in Sydney 18 Mar. 1/3: Ben succeeded in peppering his opponent in the face.
1854		Delhi Sketch Bk 1 Jan. 24/1: The Rebel forces had entered the province of Chihli. It is more than probable therefore that they will get well prepared.
1856		C. Reade It Is Never Too Late to Mend III 133: This is the beggar that peppered the hole for me, and now we will pepper him.
1868		H.L. Williams Black-Eyed Beauty 36: Oh! you peppered the big Johny Bull of a moll!
1869		Sportsman (London) 8 Dec. 2/1: Notes on News [...] The poor thing [i.e. a squirrel] was again ‘peppered’.
1873		Sl. Dict.
1874		‘Old Calabar’ Won in a Canter II 17: ‘Jack is the worst shot in the neighbourhood, he has peppered half the keepers [...] in the county’.
1884		(con. c.1840) ‘Mark Twain’ Huckleberry Finn 148: The Grangerfords staid on their horses and capered around the old man, and peppered away at him.
1886		‘Ned Buntline’ Buffalo Bill 18: ‘Pepper into ’em, then, till I tell the boys here where we're goin’, so they'll be keerful how to shoot’.
1894		Star (Reynoldsville, PA) 24 Oct. 5/6: Small game that annoys them while waiting for larger game run the risk of getting ‘peppered’.
1900		Bulletin (Sydney) 29 Sept. 24/1: They bore into each other, banged, bashed, roughed and clinched. Joe peppered with his left. Tim smothered mostly till Joe gave a chance, then rushed and swung punches that staggered every time they made impact.
1909		L.A. Herald 22 Dec. 12/2: Wolgast took Picato’s peppering blows smilingly and rushed Frank to the ropes.
1930		W.R. Burnett Iron Man 18: Jeff [...] increased the pace, and continued to pepper Coke.
1941		P. Gallico Snow Goose 42: [British speaker] ‘Jerry [...] give us shrapnel and ‘e give us H. E. an’ ’e peppers us from the bloomin’ hatmosphere with Jittersmiths’.
1937		T. Thursday ‘License for Theft’ Ten Detective Aces Sept. 🌐 All you have to do in order to save your fat body from a condition resembling a sieve, due to a large peppering of lead, is to remain quiet.
1962		(con. 1940s) G. Mandel Wax Boom 193: The whole Kraut army’ll pepper you.
1973		Csonka & Kiick Always on the Run 42: We’d pepper the cars [with snowballs] until somebody called the police.
2015		Section Boyz ‘Trapping Ain’t Dead’ 🎵 Manaman ah pepper man easy.
2020		G. Krauze What They Was 199: Couple man went to smoke one yout, they blatantly peppered the brer, let off a full clip.

3. to tease, to deceive [SE throw pepper in someone’s eyes].

1675		F. Fane Love in the Dark III i: I cannot chuse but laugh at him. How his Wife pepper’d him!
1843–44		Dickens Martin Chuzzlewit (1995) 359: If he could only have been one of his own forefathers, he said, wouldn’t he have peppered that same Lion, and been to him another Brute Tamer with a wire whip.