c. 1230 - 1588Gropecuntlane used as a street name in at least twenty locations in Medieval Europe. Keith Briggs, OE and ME cunte in place-names, Journal of the English Place-Name Society, 41, 26-39 (2009). pdf.
1325 or earlier, from The Proverbs of Hendyng (quoted from An Old English Miscellany Containing a Bestiary, Kentish Sermons…, 2001):
Ȝeue þi cunte to cunnig and craue affetir wedding.
(Give your cunt wisely and make (your) demands after the wedding.)
What aileth you to grutche thus and grone / Is it for ye would haue me queint alone?
1673 or earlier, poem A Ramble in St. James's Park, by John Wilmot 2nd Earl of Rochester (published in The Works of The Earl of Rochester, Yale, 1968):
Had she picked out, to rub her arse on,
Some stiff-pricked clown or well-hung parson,
Each job of whose spermatic sluice
Had filled her cunt with wholesome juice, ...
1880 Samuel Langhorne Clemens (Mark Twain), [Date: 1601.] Conversation, as it was the Social Fireside, in the Time of the Tudors
[Y]e abbot, spying through ye key-hole, did see a tuft of brownish hair with fair white flesh about it, wherefore when ye priest's prayer was done, his chance was gone, forasmuch as ye little maid had but ye one cunt, and that was already occupied to her content.
1991, Silence Of The Lambs, by Thomas Harris:
"I can smell your cunt!"
1993, Trainspotting, by Irvine Welsh:
"The only problem [with heroin], at least the only principal problem is that you have to put up with all manner of cunts telling you...", "No way would I put that stuff in my veins."