Yes, Joe, a song sung in the voice of a long-since 'deflowered' woman may refer to when and how she lost that maidenhead:
"Oh, we left 'em in the ale house
And passed the jug around!" (Three Drunken Maidens)

"Four and twenty virgins came down from Inverness ..." (The Ball At Kierymuir) (sp?)

"Earl Marshall had my maidenhead underneath these cloths of gold." (Eleanor & Henry)

Paddy Graber sings a song called "Arbutus Tree" that would fit your category. (She prays to the gods for rescue from a forced 'maidenhead-verification procedure' and is turned into a tree.)

The song "Unquiet Grave" is one of many songs that alludes to virginity in the context of impossible things:
"Go bring me water from the desert
Or blood from out a stone.
Go bring me milk from a young maid's breast
That young man never has known."