Green’s Dictionary of Slang

1. (also peppered off) very badly infected with venereal disease; occas. crab-lice [pepper v. (1) + play on hot adj. (6a)] .

1599		Nashe Praise of the Red Herring 44: He was peppered for it.
1607		Rowlands Diogenes Lanthorne 14: Matters marke the end of him that hath beene laide fiue times of the Pox [...] if he be not throughly frenchified, and well peper’d for his venerie, then I will for seauen yeares eate hay with a horse.
1615		J. Stephens Ess. and Char. iv. 28: And then you snarle against our simple French As if you had beene pepperd with your wench [Nares].
1623		Middleton & Rowley Spanish Gypsy I v: Yes, peppered, on my life.
1660		Wandring Whore I 7: [She] was terribly pepper’d with herds of Crabblice (as visible in her tayl as cloves in a gammon of Bacon).
1678		J. Ray Proverbs (2nd edn) 88: He is pepper’d.
1696		Motteux (trans.) Pantagruelian Prognostications (1927) II 694: Swaggering huff-snuffs, bouncing bullies, [...] tory-rory rakes and tantivy boys; peppered, clapped, and poxed dabblers .
1700		‘The Sound Country Lass’ in Playford Pills to Purge Melancholy II 212: Their Tails are pepper’d with the Pox, / and that you’re welcome to.
1710		C. Shadwell Fair Quaker of Deal II i: I could wish a Punk of my Noble Captain’s was well pepper’d with it.
1725		New Canting Dict. n.p.: Pepperd off, Damnably Clapt or Poxt.
1737, 1759, 1760, 1776		Bailey Universal Etym. Eng. Dict. [as cit. 1725].
1772		Bridges Burlesque Homer (3rd edn) 145: All atrides got, / Was to come here, and stink, and rot; / Which lot did justly fall to him, / For following such a pepper’d brim.
1785		Grose Classical Dict. of the Vulgar Tongue.
1794		Sporting Mag. Oct. V 49/2: Flats were very few indeed; and the peppered tails returned as they came, without purchasers.
1797		Bridges Burlesque Homer (4th edn) II 46: I wish the brimstone’s pepper’d tail / Was in the belly of that whale.
1811		Lex. Balatronicum.
1823		Egan Grose’s Classical Dict. of the Vulgar Tongue.

2. dead, badly hurt [pepper v. (1)].

1622		Massinger Virgin-Martyr IV i: Gone, gone; he’s pepper’d. It is thou Hast done this act infernal.
1832		Egan Bk of Sports 190: The right side of his face was sadly peppered.
1847		R.F. Walond Paddiana I 313: I’m peppered, I warrant, for this world! Ask for me to-morrow, and you shall find me a grave man!

3. euph. for damned adj. (1)

1884

Sporting Times 25 Oct. 2/2: ‘Ghost be peppered,’ replies he contemptuously’.

4. in fig. use of sense 2.

1899

‘Pot’ & ‘Swears’ Scarlet City 147: The Marquis of Eastbourne got pretty well peppered over that Derby.