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Aug 16, · Madonna lost her virginity in the back of a Cadillac. It was revealed by her brother Christopher Ciccone in his book, Life With My Sister Madonna. She also dated Tupac, John F. Kennedy, Jr., Antonio Banderas, Lenny Kravitz, Dennis Rodman, and the artist Jean-Michel Yvonne Williams, Yvonne Williams.

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No, she did not lose her virginity. In order for someone to lose their virginity, sexual intercourse needs to take place. If all she did was kiss, she's a virgin.

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