Brooke Shields Dean Cain
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Brooke Shields lost her virginity to Dean Cain.

Brooke revealed in her memoir, There Was a Little Girl: The Real Story of My Mother and Me, that she lost her virginity to Dean Cain. "It should have been what I had wished for myself, but in an instant, guilt slapped me in the face," she wrote.

"I got so overwhelmed that I jumped out of my bed. I was buck naked, streaking down a hallway and running as if I had just stolen someone's wallet. What a sight!" she went on. "Dean leapt up and ran after me with the comforter in his arms. He threw it around me, grabbed me around my shoulders and stopped me from running."