1. shooter26

    What’s up or should i say down with her rack. Put a bra on please.

  2. Well this makes complete sense when you consider their proclivity for younger men…

  3. Better posing with than posing for. I just ate.

  4. Happy_Evil_Dude

    “Imma take stupid picutres of her and call it art. Thums up y’all!”

  5. “For this picture, Demi, I want a shot that looks like you’re dating a more “age appropriate” man…and say “cheese.”"

  6. “Terry, could you make my daughter look hot with your photographic wizardry?”

    “Well, I’d have to have sex with her firs—oh wait, which daughter? Oh, wait.”

  7. She’s aging gracefully.

  8. MRF

    His thumb is like a desperation ESP.

  9. tlmck

    Demi Moore and Terry Richardson. This cannot end well.

  10. Martina

    at first I thought it was Jennifer Connelly …

  11. that damn Terry Richardson hangs out with all the hot bitches—-oh wait, nevermind

  12. Fuck your:
    • thumbs
    • handlebar-to-chops-mustache
    • stupid receding hairline
    • flannels
    • officer Poncharello glasses

  13. Jamriqua

    He couldn’t find his grandmother, so he grabbed the next best thing

  14. Well, it’s finally happened: they managed to invent ironic cleavage.

  15. toopier

    pornographer photographer meets gravity cavity

  16. THIS fucking truck driver hillbilly is Terry Richardson? Now I understand why his photography is so shitty.

  17. Donkeylicks

    I used to hate Terry Richardson but then I realized (if) I was a visitor from the future he would be me and I would be him.

  18. Demi looking as beautiful as every. So sexy.

  19. I didn’t know Tori Spelling’s chest hole was contagious.

  20. MissJonesy

    She’s gotta get some new boobs for real.

  21. Creeper creeper creeper creeper creeper …

  22. Timothy

    He is old enough to be her next boyfriend’s father!

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