Cunt has been in common use in its anatomical meaning since at least the 13th century. While Francis Grose's 1785 A Classical Dictionary of The Vulgar Tongue listed the word as "C**T: a nasty name for a nasty thing", it did not appear in any major English dictionary from 1795 to 1961, when it was included in Webster's Third New International Dictionary with the comment "usu. considered obscene". Its first appearance in the Oxford English Dictionary was in 1972, which cites the word as having been in use since 1230 in what was supposedly a London street name of "Gropecunte Lane". It was, however, also used before 1230, having been brought over by the Anglo-Saxons, originally not an obscenity but rather a factual name for the vulva or vagina. Gropecunt Lane was originally a street of prostitution, a red light district. It was normal in the Middle Ages for streets to be named after the goods available for sale therein, hence the prevalence in cities having a medieval history of names such as "Silver Street" and "Fish Street". In some locations, the former name has been bowdlerised, as in the City of York, to the more acceptable "Grape Lane".

The word appears several times in Chaucer's Canterbury Tales (c. 1390), in bawdy contexts, but it does not appear to be considered obscene at this point, since it is used openly. A notable use is from the "Miller's Tale": "Pryvely he caught her by the queynte." The Wife of Bath also uses this term, "For certeyn, olde dotard, by your leave/You shall have queynte right enough at eve ... What aileth you to grouche thus and groan?/Is it for ye would have my queynte alone?" In modernised versions of these passages the word "queynte" is usually translated simply as "cunt". However, in Chaucer's usage there seems to be an overlap between the words "cunt" and "quaint" (possibly derived from the Latin for "known"). "Quaint" was probably pronounced in Middle English in much the same way as "cunt". It is sometimes unclear whether the two words were thought of as distinct from one another. Elsewhere in Chaucer's work the word queynte seems to be used with meaning comparable to the modern "quaint" (charming, appealing).

By Shakespeare's day, the word seems to have become obscene. Although Shakespeare does not use the word explicitly (or with derogatory meaning) in his plays, he still plays with it, using wordplay to sneak it in obliquely. In Act III, Scene 2, of Hamlet, as the castle's residents are settling in to watch the play-within-the-play, Hamlet asks Ophelia, "Lady, shall I lie in your lap?" Ophelia replies, "No, my lord." Hamlet, feigning shock, says, "Do you think I meant country matters?" Then, to drive home the point that the accent is definitely on the first syllableof country, Shakespeare has Hamlet say, "That's a fair thought, to lie between maids' legs." Also see Twelfth Night (Act II, Scene V): "There be her very Cs, her Us, and her Ts: and thus makes she her great Ps." A related scene occurs in Henry V: when Katherine is learning English, she is appalled at the "gros, et impudique" words "foot" and "gown", which her teacher has mispronounced as "coun". It is usually argued that Shakespeare intends to suggest that she has misheard "foot" as "foutre" (French, "fuck") and "coun" as "con" (French "cunt", also used to mean "idiot"). Similarly John Donne alludes to the obscene meaning of the word without being explicit in his poem The Good-Morrow, referring to sucking on "country pleasures".

The 1675 Restoration comedy The Country Wife also features such word play, even in its title.

By the 17th century a softer form of the word, "cunny", came into use. A well known use of this derivation can be found in the 25 October 1668 entry of the diary of Samuel Pepys. He was discovered having an affair with Deborah Willet: he wrote that his wife "coming up suddenly, did find me imbracing the girl con my hand sub su coats; and endeed I was with my main in her cunny. I was at a wonderful loss upon it and the girl also...."

Cunny was probably derived from a pun on coney, meaning "rabbit", rather as pussy is connected to the same term for a cat. (Philip Massinger: "A pox upon your Christian cockatrices! They cry, like poulterers' wives, 'No money, no coney.'") Because of this slang use as a synonym for a taboo term, the word coney, when it was used in its original sense to refer to rabbits, came to be pronounced as /ˈkoʊni/ (rhymes with "phoney"), instead of the original /ˈkʌni/ (rhymes with "honey"). Eventually the taboo association led to the word "coney" becoming depreciated entirely and replaced by the word rabbit.

Robert Burns used the word in his Merry Muses of Caledonia, a collection of bawdy verses which he kept to himself and were not publicly available until the mid-1960s. In "Yon, Yon, Yon, Lassie", this couplet appears: "For ilka birss upon her cunt, Was worth a ryal ransom".