The Hollywood Gossip Caption Contest 52

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    Welcome, celebrity news fans around the world, to The Hollywood Gossip Caption Contest, our Friday tradition. Who won this week's Caption Contest?

    The winner is Katy Lynn. Congratulations! The winning entry appears below. Thanks to all of you for playing and best of luck again in this week's contest!

    Hugh and His Women

    Oh no! I have a hole in my right boob!


    she just wants guys to like that why she asked someone to take a picture of her.


    ohh goodie these are the first non wrinkley balls i have seen since i started dating hef!


    hmm i wonder what cup size these would be!!


    hey hef - look ..i got bigger balls than you


    maybe i need them bigger so hef will take me back...hmmm


    These are kinda similar to Hef's but not so red!


    I wonder how much boobs this size cost?


    "I can't wait to drop these on Kendra and Bridget's heads while they're sleeping!"


    Holly Madison is used to gripping balls, but not like this


    Hmmm, I like this size. Maybe I should get them done this big?

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    Holly Madison Biography

    Holly Madison Photograph
    Holly Madison is a Playboy model and the ex-girlfriend of Hugh Hefner. As for Madison, she is best known for getting naked a lot and... More »
    Astoria, Oregon
    Full Name
    Holly Cullen

    Holly Madison Quotes

    We are no closer to getting married than we were years ago. It's like a car stalled at the side of the road.

    Holly Madison [on Hugh Hefner]

    I have no pull anymore. Hef and I aren't together.

    Holly Madison