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To be so in love with someone, that head over heels is not enough. You are crazy in love. You are literally and figuratively upside down in love, hence "heels over head." Crazy awesome love.
Bernard loves Harriet so much that he is "heels over head."
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When a woman is laying on her back with her legs open and in the air during sexual intercourse.
Spin off of 'Head over Heels'.
Girl: "I'm straight Head over Heels for my man."
Other Girl: "Damn i'm just Heels over Head for mine...😏"
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A variation or play on words of "head over heels". However, Heels over Head specifically refers to Cunnilingus, with "head" being a term for oral sex.
The woman receiving the Cunnilingus, or head, is on her back, with her legs above her.
Especially appropriate when she is wearing high heels.
Girl, to a friend: I was Heels over Head last night with the boyfriend. I was running my stiletto heels up and down his back as he went down on me.
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