Bree Olson talks sex life with Charlie Sheen & other “goddess” in Playboy

It looks like all you have to do to go from an escort and adult film actress who does just everyone and everything on camera to the cover of Playboy is to screw a famous guy. Charlie Sheen’s “goddess” #1, Bree Olson, is featured on the August issue. Advance details of her interview have her talking up Charlie Sheen as a lover and claiming she never did anything sexual with the other goddess, Natalie Kenly, who hung around longer than Olson did but eventually ditched Charlie too. (Probably once the money started drying up.)

breeplayboyShe may have broken up with Charlie Sheen in April, but Bree Olson insists she’s “still a goddess. I’m just not Charlie’s goddess.”

How did the 24-year-old Indiana native end up with the troubled actor, who was fired from Two and a Half Men in March? “I suppose it was my movies,” Olson, who has appeared in more than 250 adult films, tells the August issue of Playboy.

When Sheen, 45, first contacted Olson (whom he had never met), the actor invited her over to his house for a meet and greet. After hitting it off, the adult film star — along with Natalie Kenly — soon began cohabiting with Sheen in his Sherman Oaks, Calif. mansion.

“He’s intelligent, he’s charismatic, he’s superfunny,” Olson (real name: Rachel Oberlin) says of the actor. “And he’s good in bed. I mean, he’s had a lot of practice.”

Despite rumors to the contrary, Sheen was “gentle and considerate” in between the sheets, Olson says. “He’s just a rock star. He’s a powerhouse. He’s a very sensual and sexual person, and when I was with him I felt as if we became one together, because he’s just so enticing sexually.”

As for the sex she reportedly had with Kenly? “That was a lie,” Olson now says. “I didn’t really even know her. Okay, all three of us got together, I think, twice. They did their thing together, and Charlie and I did our thing together. And we had two different beds. She and I would go to whichever bed, and he would pick. You know, ‘Where am I sleeping tonight?'”

Currently single and living in Los Angeles, Olson tells Playboy she’s retiring from the adult film industry to focus on becoming a real actress. “I can do this,” she says. “I’m so winning right now.”

[From US Weekly]

Is anyone else skeeved out by the thought of Charlie Sheen making an O face with those gold teeth of his? Bree is being demure and trying to act like she didn’t have sex with the other “goddess,” and it was just straight sex with Charlie. It took me five seconds to google and find a scene where she has sex with famous porn actress Sasha Grey, so it’s not like she’s never screwed another woman. She’s also done just about everything else on camera. Maybe she’s telling the truth though and she only does sex with women for pay. (Strike that, it’s not like Charlie wasn’t paying her.)

Other mistresses of famous guys do sex tapes to make money after they gain a little notoriety, but it’s not like Olson didn’t do that to death already. Now she’s going to be a “legitimate” actress. She did get the cover of Playboy, that’s a start. Maybe Sheen will cast her on that mystery sitcom he keeps leaking to the press that’s about to happen but never materializes. That must have been her motivation to make sex with a bipolar crack-smoking lunatic sound like a harlequin romance novel.


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43 Responses to “Bree Olson talks sex life with Charlie Sheen & other “goddess” in Playboy”

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  1. Sumodo1 says:

    That is one TACKY cover!

  2. teehee says:

    God, grow up and clean up you superficial buttwipe– he really has an empty life now doesnt he.

  3. original kate says:

    does anyone else find it sad that a 24 year old has made over 250 adult movies?

  4. Cherry says:

    ROFLOL! This is such a hilarious item that I’m actually considering buying this issue of Playboy to read the whole interview. I mean, come on:
    ‘Olson tells Playboy she’s retiring from the adult film industry to focus on becoming a real actress. “I can do this,” she says. “I’m so winning right now.”’
    That’s priceless! Yes Bree, you’re WINNING! Woohoo!

  5. Praise St. Angie! says:

    seriously, Somodo…reminds me of the Steppin’ Out cover with that chick that Jon Gosselin dated.

    “Judge this, haters!”

  6. Kelly says:

    Wow, that top picture is scary. I didn’t know teeth could be bleached that white.

    I agree, 250 movies is a hell of a lot of movies. I’m 42 and I haven’t reached triple digits, LOL. 250? I haven’t Googled her oeuvre, but I wonder how many PEOPLE she’s had sex with, as the trend now is for women to have sex with at least 2 men – in every permutation possible. The mind reels…

  7. the original bellaluna says:

    Frankly, I find whatever face that is he’s making in that last pic terrifying!

  8. *bRaZiLiAn* says:

    She’s kinda nasty!
    Sumodo1: i agree…tacky ass cover!

  9. Esmeralda says:

    “That must have been her motivation to make sex with a bipolar crack-smoking lunatic sound like a harlequin romance novel.”

    Ha ha ha! You couldn’t have put it better. And if sex was so darned hot with Charlie, why isn’t she still with him?

  10. Esmeralda says:

    250 adult movies means AT LEAST 250 random sexual encounters – why, she’s a walking bed bug!

  11. Jackson says:

    Ewww. This whole post needs to be washed in bleach and lit on fire. I can see the skeevies running off the page.

  12. MarenGermany says:

    the minute you choose to take it up your butt to make a living you have blown away all your chances of ever doing anything else on camera.
    you are officially at the bottom of the food chain.

    good luck with the acting career.

  13. ZenB!tch says:

    Playboy is not what it used to be (as per my parents) – now they look like Pammy-Monsters and they ARE Pammy-Monsters. It’s just a bunch of tacky plastic porn stars, like Hustler-lite (or Penthouse or whichever the really bad one was back in the day).

    Allegedly, they used to look like Betty Page, naked but classy.

    Oh and look at how much uglier she is in the real picture vs. the cover, that is a helluva lot of Photoshop – more than Rachel Weiss and Drew Barrymore and Kate Winslet put together and that is just to make her look vaguely human.

  14. Anonny says:

    She’s “24”?? Srsly? I’d go higher…maybe as much as 10 years higher.

  15. guesty says:

    She could wind up being Hef’s next gf. *gags*

  16. ZenB!tch says:

    “That was a lie,” Olson now says. “I didn’t really even know her. Okay, all three of us got together, I think, twice.


    So those 2 times didn’t count?

  17. Truthful says:

    skeezy, no matter how mainstream these chicks try to make it sound.


    how did the other chick’s butt taste after you had CS next.

    nasty and sorid.

    who is worse Hef’s ex or these birds??

  18. the original bellaluna says:

    @ ZenBitch – Naww, those 2 times were fine…but all the other times were lies!

  19. Rita says:

    The Playboy brand is barely alive and scraping the bottom of the barrel. I remember when Hef didn’t promote straight-up porn because he thought it demeaned women. As the worm turns.

  20. Stubbylove says:

    Her teeth are REALLY white in that 1st pic. Damn.

  21. Patricia says:

    @Jackson – love it!!!

  22. What is going on underneath her arm in the 1st photo, and why is her skin grey?? And is it just me, or does she look much closer to 30 then to 20 years old???

  23. Stephie says:

    Yuck. Why did I read this?
    @original kate, yes, that is pretty sad, way too many.

  24. ladybert62 says:

    Perhaps she is unclear on the concept of what a lie is (is she related to Casey Anthony?) – egads, 250 adult films and she is only 24 – I dont think so. Looks like she has about as much acting ability as some others in hollyweird.

  25. velourazure says:

    fluorescent teeth and drug-resistant gonorrhea. klassy.

  26. MarenGermany says:

    @ cleveland girl and anonny

    her looking older than she is, as some point out here, is just the make up.

    Have you seen other pictures of her? she looks much closer to 15, which matches with charlies “barely legal”-collection and frankly gives me much more creeps than anything else this bipolar wild hog has ever done.

  27. Anti-icon says:

    I fear these early choices of her … and her complete lack of remorse about them — foretell a “difficult” future as both a “legitimate actress” but mostly as a human being. I pity this person.

  28. Sloane Wyatt says:

    Bree has lost touch with her own sense of worth and dignity.

    Bree has both, as do most all of us who aren’t out and out sociopaths. However, as the years fly by, this sad girl will lose her chance of being at peace with herself if she continues on this path.

  29. Thea says:

    Its a sad day when a porn star dumps you. And even your money cant buy you love.

  30. malachais says:

    She looks so worn out, good grief. 250 movies and 24 years old.

  31. feebee says:

    CB – you google searched for her and another chick? hee.

    I wonder if I’ve SEEN 250 movies. I getting old so I guess maybe I have but she must have been a very busy girl to do (literally and figuratively) 250 movies in so few years.

  32. B says:

    Ugh. I don’t exaggerate when I say that this chick makes my stomach turn. I once visited her twitter to find her asking her followers if any of them were her daddy…she said if she knew her daddy was, she would “*totally* f*ck him”. Another gem: she told her followers to place a paper bag over her head with a picture of another girl…she wanted the follower to think about that other girl while screwing her. Not to mention, her fantasy about being raped by a stranger.

    She’s one sick puppy.

  33. MorticiansDoItDeader says:

    She HAD to be contractually obligated to say those things about Charlie; or she’s whip smart and fears saying anything negative about him will cost her legit acting gigs. You know, the ones no one is thinking about giving her.

  34. SphincterSaysWhat? says:

    @cleveland girl is right… she has vagina pits. She IS NOT 24 years old.

  35. Jaye E says:

    Well, porn is not like mainstream movies where they are on set sometimes for months at a time. And sometimes they only do 2 or 3 scenes per movie, so it’s possible that she did multiple movies per day or week. Based on that, it’s plausible that she’s done 250 movies in the 4 or 5 years she’s been in the business.

  36. Rio says:

    Ok, so if she’s 24 and started working at 18, that’s 6 years of work, which averages about 40 movies a year. That sounds like a lot, and it would be for a “mainstream” actress, but that’s probably pretty representational of porn films.
    Couple of things to remember– porn movies are SHORT and shot on a very tight schedule. There are also often several performers. So it’s not like she had a starring role in 250 2-hour-long opuses…probably more like a scene or two in 30-45 minute videos.

    While hooking up with Charlie Sheen for any length of time certainly speaks of a lack of intellect, I don’t think she’s morally bankrupt for doing porn. Hey, guess what, there’s a market for it, it’s not illegal, and some people like to get it on in front of cameras. Better to make an honest living at it than an “Oopsie! I made a sex tape I never EVER wanted released, despite my professional hair and makeup in it!”

  37. Anti-icon says:

    I am an open minded, older woman who lived through much of the ideas of the women movement of the time in which I was raised. Which is I became a career person and made a good wage (unequal to the men in the field) and I was respected in my field. And still, to this day, what “ruined” my entire life, not just my personal relationship with my husband of 16 years — but all the “other” aspects of my identity — was a homemade porn tape that he made and I discovered. After that, it became a legal issue; and a parenting issue….and a moral issue — big time — in how it was “presented” to the children of this hideous “porn mistake.” But I don’t think it was a mistake now. I think it was a strategy. A legal maneuver based upon an unethical act, and also an immoral one.

    So I think people who participate in born are broken. I pity them.

  38. Anti-icon says:

    Meant to say “porn” not born. (interesting error though, huh Dr. Freud?) LOL

  39. anony says:

    She’ll become a real actress like Ginger Lynn became a real actress.
    Or Jenna Jamison.
    Or any porn actress.

  40. JRenee says:

    Any man doing as much coke/crack as Charlie reportedly does is not having great sex- the penis is not working.
    I’m with jackson, burn this thread- ewww!

  41. Omg! So hot body!

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  43. Josh says: