Bree Olson is Doing Playboy Now

May 11th, 2011 // 58 Comments

Looking to finally do something pure and innocent with her life, former Charlie Sheen goddess/porn star Bree Olson is posing for Playboy, according to TMZ:

Bree — who dumped Charlie Sheen last month via text message — reportedly swore off the adult industry after she started dating the Warlock … but now that the relationship is over … it appears she’s easing up on her no-adult policy.

Just to put things in perspective, it’s almost impossible not to see Bree Olson naked anytime you’re on the Internet. Christ, look at her Twitter background. I’m pretty sure I could Google a recipe for gazpacho, and the top result would be a bowling pin up her butt. It’s like asking air to pose for Playboy.

Photos: Courtesy of (NSFW)


  1. Youdrink waytoomutch

    Wow…didn’t see that one coming….no, really!

  2. Myah, what’s up, slut?

  3. Rancid

    For fuck’s sake – she was Charlie Sheen’s hump bag.

    That makes her more worn out than a pair of rented bowling shoes.

  4. should fit right in at the mansion, being a whore and all

    • Lady Blah Blah

      Dude, Thanks again for the suggestions for DC restaurants. We decided to stick to establishments within walking distance of our hotel (Capitol Hill Hyatt, mostly paid for by work), and our best dining experience (I would say my best dining experience EVER) was at the Indian restaurant Rasika. Expensive but real gourmet food and killer drinks.

  5. Cock Dr

    Must need money. Nude photoshoots are certainly less physical stress than DP and/or rough anal intercourse.
    How long until she totally sells out crackhead Charlie with a series of “tell-all” interviews?

  6. Keyser Ballsy

    I believe the beef curtains will have to be airbrushed out.

  7. Bree Olson Playboy
    Commented on this photo:


  8. Fisherman

    I’d rather Heidi Montag did another spread, that’s how pathetic this news is. The editors at PB are literally retarded if they think this is a good idea.

    • ghost

      The editors of Playboy are trying anything they can to keep it all from going under.

      • Jacob

        They are trying anything that doesn’t involve actual effort or doing a good job. It’s not like Playboy has some super complicated formula, but they keep fucking it up. Their current editor was poached from a failing Maxim. Think about that.

  9. Yeezy's Son

    “It’s like asking air to pose for Playboy” GENIUS! well done Fish

  10. vv

    This girl looks quite pretty when wearing make-up etc, but she looks like crap in any candid pic I’ve seen of her.

  11. She’s like the girl next door, provided you live at 68 Bukkake Court.

  12. Bree Olson Playboy
    Commented on this photo:

    Is that…is that a large bruise on the inside of her upper left leg? Dear Lord

    • Hurrrp

      No, it’s just a very horrible Photoshop job. Look at her right leg, and look at her left. It’s almost as if the “artist” didn’t know how to blend shadows properly. And don’t get me started on the horrendous masking job they did (ie: the blur around her left hamstring, and the hard edge on her left calf. Unless she’s standing up against a wall that the “artist” removed and neglected to compensate for, that’s just wrong)

      Had it been a bruise that was known to exist prior to the shot, top priority would have been to remove it. It’s just a shitty shadow, on top of a shitty photoshop job. It’s obvious that’s a professional shot.

      And yes, while I know everyone on the internet took a Deviant Art tutorial and calls themselves a “shop pro”, I do this shit everyday, but unfortunately I don’t get to mask and clean up porn stars :( Truthfully, I would let her pay me in anal.

  13. Meh, she’s in penthouse this month.

  14. Richard McBeef

    I love it when daddy issues manifest themselves as a willingness to take it in the ass for approval.

  15. Gigs

    Who wants to see her in Playboy when they’ve already seen her with 2 cocks in her ass and another in her mouth?

  16. Deacon Jones

    Some may claim this happened awhile ago, but Playboy has officially jumped the shark if this story is true.

  17. Parker

    I’d like to stuff her hot little fudgepot full of my penis.

  18. Bree Olson Playboy
    Commented on this photo:

    Oh, good. Now we FINALLY get to know what she looks like.

  19. sdrizzle

    Isn’t a hooker in Playboy a little redundant?

  20. Bree Olson Playboy
    Commented on this photo:

    fuck you superficial. thank you bree olsen for giving us heteros a truly blessed life. she obviously could have been a cowardly regular model but no, this girl gave us the full package. Thank you. Looking forward to her playboy shoot, they always make the girls look extremely gorgeous unlike low budget pornos.

  21. Jessesgirl

    She’s prettyish in some of these pics but looks like another person without makeup.

  22. Make it stop.

  23. Bree Olson's Poontang

    I can say for a fact she hasn’t done a DP yet.

    • Bree Olson's Brown Eye

      Lol, yeah you are probably right, she has never limited to only a DOUBLE. She is pretty careful to always have at least three cocks in her at once.

      Personally, I am surprised she has not been reduced to diapers yet. I bet she can effortlessly shit a football.

    • The Man

      I agree. I do not believe she has had double penetration. She has a nice and tight twat however. Completely gets into the sex. You should check out Brees Summer Camp the movie. It was great! One cream pie in it!

  24. Playboy? Damnit, I thought for sure she’d be featured in my favorite outdoor magazine, Spelunking Weekly.

  25. Bree Olson Playboy
    Commented on this photo:

    So now one of America’s most cherished and veritable institutions, Playboy Magazine, is the purveyor of flapity flappity roast beef lips.

  26. That’s like The New York Times doing a detailed expose on how water is “wet”.

  27. Will the pages of this edition come pre-soaked in Valtrex in her honor?

  28. Bree Olson Playboy
    Commented on this photo:

    Why would I look at a photoshopped, fake phoney fraud nudie pic in Playboy why I can watch her her crack whore ass get rammed by a giant black dick on Pornhub?

  29. anonym

    now why the fuck would i want to look at playboy pics when her hardcore pics are all over the internet already?

    lame ass fucking playboy. they can’t get anyone worthy to pose for them these days

    • lindsay

      thats so true! ive always admired playboy for being the best and classiest mens magazine. playboy is ICONIC and the greatest sex symbols of all time have posed for and/or been in the magazine from marilyn monroe to bettie page to brigitte bardot. but in recent years, playboy has fallen WAY off! it doesnt get much lower than tara reid and heidi montag.

  30. Veronica

    I’ll never have gazpacho again!

  31. the captain

    yesterday was her eighteenth birthday, folks!!

  32. cc

    Remember when Playboy had beautiful, natural women? Me neither.

  33. Ken Kaniff

    Why would I pay to see her in Playboy when I can get her off Craigslist for the same price?

  34. Wow. With an intro like that how could anyone avoid clicking your spam link?

  35. For most women, doing Playboy is an opportunity to step outside of themselves and be Photoshopped within an inch of recognizability. For Bree Olson, doing Playboy is a chance to have at least one photo taken without five penises in or around her.

  36. argleblargle

    Makeup is pretty amazing. It makes guys think they want to get into her pants and distracts them from thinking about what’s actually down there.

  37. Bree Olson Playboy
    Commented on this photo:

    she must be related to a tortoise, there is no other way i could explain why her neck looks like that

  38. Bree Olson Playboy
    Commented on this photo:

    I haven’t seen a smile like that since Jack Nicholson was the Joker.

  39. Bree Olson Playboy
    Commented on this photo:

    Why is she cleaning the countertop with windex?

  40. tlmck

    I thought first you did Playboy, and then porn.

  41. Bree Olson Playboy
    Commented on this photo:

    Why is she using Windex on the countertop? Woman fail!

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