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One that comes to my head immediately is "Walk this Way" with Run-D.M.C. and Aerosmith. Walk this way = losing your virginity. Hell at one point in the song Stephen Tyler sneaks in "just give me some head".
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Actually that song was inspired by the Mel Brooks film Young Frankenstein. At one point in the movie when Gene Wilder (Frankenstein) first meets Igor, Igor begs Frankenstein to "walk this way" and he starts sidling/walking in a weird way. Gene Wilder does the same.
Aerosmith wrote the song "Walk This Way" in tribute to the film, basically.
As far as songs that I listened to when I was a kid and didn't grasp...I guess a lot of the oldies (60's and 70's stuff) that my dad listened to was over my head. Take Neil Diamond's "Cherry Cherry". Yeah, obviously it's about a girl who's great in bed and Neil wants to get her back in there to see her moves again (read: a good lay). But when I was a kid I was just like "yay, it's a happy song!"
Jam it back in, in the dark.