"Like a Virgin" Glee cover
The actual performance is phenomenal, but Glee has been really good/obnoxious about getting videos removed from youtube.
"Only the Good Die Young," Billy Joel
My mom had to explain to me that this was a song about Billy Joel seducing a Catholic virgin. I had no idea. I was in high school when she told me this.
"Touch Myself," Divinyls
Because sometimes the best love is self-love.
"Strawberry Wine," Deanna Carter
I love this song. I also had no idea it alluded to a teenage girl's first time.
"Fifteen," Taylor Swift
Technically, only the line about Abigail is potentially about virginity "loss." But I love me some Taylor Swift, so I had to include it!