Some time ago on Facebook, several posters ended up chatting about the vocabulary for talking about a gay man’s anal virginity. The term cherry plays a central role in this vocabulary domain — taken over, like some other sexual vocabulary, from reference to women and their sexuality.
We start with women. In Green’s Dictionary of Slang, it begins with the cherry as an image of ripeness, with two related subsenses (both originally U.S.), with the second as an extension of the first:
(a) (i) the hymen; (ii) one’s viriginity [antecedent cites in Green from 1641 and 1700, clear cites from 1918]
Subsense (ii) has the syntax of virginity, normally with an obligatory possessor, as in the collocations
save, keep one’s cherry; lose one’s cherry (to someone), give (up) one’s cherry (to someone); have, get, take, steal someone’s cherry
plus the very common pop and bust someone’s cherry, with a vivid allusion to breaking the hymen.
Now the anus has no real analogue to the hymen, but the ‘viriginity’ subsense can be transferred to anal intercourse, giving the full range of possessive collocations as above, but now used of gay men rather than women.
Back to vaginal intercourse, with another sense of the noun cherry, referring to a person rather than virginity:
(b) (orig. US) a female virgin [antecedent cites from 1881 and1889; clear cites from 1942 on] (c) a male [vaginal] virgin [from 1948 on]
These uses have the syntax of count nouns — Kim’s a cherry, Kim and Sandy are cherries — but there’s also an adjectival predicative use, as in Kim is cherry,
Finally, we get the gay analogue of (b) and (c):
(gay) an anal [receptive] virgin [also 'anal virginity', together with cites from 1941 on]
In the Facebook discussion, I recalled that the man I lost my anal virginity to, many years ago, didn’t use any of the cherry expressions, but instead referred to what he did as breaking me in.
