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Nov 12, - 'I was buck naked streaking down a hallway': Brooke Shields recalls her 'overwhelmed' reaction after losing virginity at 22 to Dean Cain.

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Nov 13, - Brooke Shields lost her virginity to Dean Cain at age 22 and is writing all about it. Yes, before her husband Chris Henchy, before ex-husband. Nov 12, - When she was a junior at Princeton, Brooke Shields fell in love with a Chris Henchy, recalls losing her virginity as a "beautiful" experience.

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Nov 12, - Brooke Shields tells all about her celebrity romances, her mom and her crazy life as a child star. Subscribe now for instant access to our. Subscribe: Follow @JimandSamShow on Facebook, Instagram, Snapchat, and Twitter.

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Brooke Shields tells Meredith about how supportive Dean Cain was when she lost her virginity. Be sure to. Brooke Shields - Losing Virginity, Michael Jackson Relationship, Joe Jackson, Fame, Modeling. Leonel Kris.

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Brooke Shields' first time was with Superman! Brooke Shields Reveals She Lost Her Virginity to Dean. Nov 12, - Brooke Shields has admitted that her mother “kept track” of her virginity, which she lost at the age of The year-old actress, who has dated.

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Nov 13, - Case in point: Brooke Shields discussing her intimate but guilt-ridden first time in her new memoir, There Was a Little Girl: The Real Story of My. Dec 4, - Dean Cain spoke to the Today show about his "college sweetheart" Brooke Shields losing her virginity to him many years ago.