Stephen Wayda/Playboy Magazine
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Kardashian first made a pictorial splash when she posed nude in a 12-page spread in the December 2007 issue of Playboy. Three years later, she says she regrets taking it all off for Hef & Co. "I'm sorry I did Playboy. I was uncomfortable," she said. "[My mom said], 'Go for it. They might never ask you again. Our [reality TV] show isn't on the air yet. No one knows who you are. Do it and you'll have these beautiful pictures to look at when you're my age.'"