For a word so common today, fuck was almost never written down for most of its history. The taboo was that strong. When it did appear, it was often disguised, coded, or buried in legal records.
Roger Fuckebythenavele (1310–1311)
In 2015, Dr. Paul Booth of Keele University discovered what may be the oldest sexual use—not in a poem, but in a Chester County Court record. A man named Roger Fuckebythenavele appears multiple times, his surname spelled variously.2
Either it refers to an inexperienced copulator... or it's a rather extravagant explanation for a dimwit.
— Dr. Paul Booth
The Coded Poem: Flen Flyys (c. 1475)
A satirical poem mocking Carmelite friars survives in British Library Harley MS 3362. Written half in English, half in Latin, it contains:
Encrypted:
Non sunt in coeli, quia gxddbov xxkxzt pg ifmk
Decoded:
"fvccant vvivys of heli" — "they fuck the wives of Ely"
The scribe knew the word was dangerous enough to require encryption.3
William Dunbar (c. 1500–1503)
Scottish poet William Dunbar used the word openly. In "The Flyting of Dunbar and Kennedy," he writes of a "wan fukkit funling" (a "wanly fucked foundling"). The OED cites 1503 as its first clear English entry.4