Ashley Dupre in Playboy

April 14th, 2010 // 160 Comments

Because Hugh Hefner will sue my young balls off and use them as his own, I can literally only get away with posting one shot of Ashley Dupre from the May issue of Playboy. That being said, I couldn’t be more supportive of everything going on here. It’s important to let women know that, with enough hooking, you too can land a profitable spread in a men magazines where your chance of getting rolled up in a carpet is barely 15%. So if anyone wants to practice breaking into the fast-paced profession of turning tricks, think of me as your personal pommel horse who won’t get attached.

The Superficial: Giving Back to the Community

UPDATE: Sorry guys, Playboy made me take it down. But enjoy this cover image which is almost exactly like seeing a woman’s bare breasts and vagina once you use your imagination and go look at porn instead.

Photos: Playboy

  1. Rolf


  2. Von Don

    She doesn’t need the money. she made like a million dollars from that song she made and sold online.

  3. swansons

    i’m saving my nickels for that coin slot

    because a quarter is not going to fit into that shorn wonton. definitely not a sacagawea.

  4. FishBone

    Ooooohhhhh MYYYYYY~JD you missed out!

  5. doogie

    Looks like they placed her head on someone else’s cartoon body.

    Look at the her neck

  6. Mel

    Wait a minute… Are you telling me Playboy has started featuring hookers who fuck Governors? Isn’t this the magazine that featured Madonna, Raquel Welch and Marlyn Monroe? This is a new low, Hef…

  7. @46 the bikini pic is hotter, even though her boobs look droopier…you’re right her stomach is rockin’ in the bikini pic – i would make love explosion! doesn’t even look like the same girl here.
    And, it’s creepy how her vageen looks like a 12 yr old’s here…I go either way on the pubes – it all depends…but this is a hooker’s gash we’re talking about!
    Playboy is crap anymore.

  8. Armando

    I agree. Young, hot, 20 something chiks who want to sell sex for money is alright by me. And boobs.

  9. Mel

    Oh wait, she’s a singer too?… AND a sex columnist?? WTF, I think this girl is having an identity crisis.

  10. Tek

    Playboy is targeted towards old men. I guess in their minds a shitload of airbrushing = hot? I don’t know. She’s pretty hot either way. The more I look at her the less I can blame old-ass Eliot Spitzer, LOL.

    @ 25
    Oh brother, here we go again…

  11. Mr. Nice Guy

    Great Body, Face and I love the Bald Pussy.
    Lenny, if you look at a women with this body and think 12 year old boy you are nuts; or a gay guy who does not like looking at a perfect pussy.

  12. Jon

    Don’t know who she is, or care..

    but she looks pretty good.

    It’s rare for this site these days to see pics like this. An actual attractive woman. Wow.

  13. The Equality Petition

    Post more of her pooper.

  14. obvi

    where is her other arm?

  15. Landon "Reaper" Armstrong

    Way to go, Spitzer! One question: Does she swallow? Or does she Spitz…??? Hahahahahahahaha…

  16. Landon "Reaper" Armstrong

    Hey, #64…I hope you’re being facetious. You can’t really be that stupid, can you?

    BTW, I think she looks great! But that’s just my opinion. I could be wrong (with thanks to Dennis Miller for a great line).

  17. A True Public Servant

    @31 SOS: “eeew #25 Pubes are masculine.”

    Ahem…pubes are *HUMAN*. Don’t be retarded. Somehow a whole generation of people have turned against this natural area of the human body en masse. You must have all been raised in a sanitary napkin or something.

    Ashley is an awesome looking babe and not too bad a singer either. She did the nation a public service by getting that publicity mongering Spitzer out of the public arena, for at least a while. She deserves extra cash just for that.

    Anyhow, she’s gorgeous.

  18. missywissy

    My first thought is, that’s a great photo, but then when you really look at it and if you’ve seen her in real life, they have air brushed her into somebody else! And I agree, even the vag looks airbrushed! Makes ya wonder what the real thing looks like???? I agree with the shaven thing, it’s weird that some guys like that, but then look at how many men molest little girls, so it just doesn’t suprise me. Those poor babies over there in Taiwan. American men keep that place in business. Sad, sad sad. When are dudes going to grow up and want to hit the real thing???

  19. turd da third

    Damn I though she had a nice clit hood piercing poking out,, turns out it was only a dirt spot on my monitor, what a disappointment, I am totally bummed now

  20. djstoop_id

    she’s pretty hot.

  21. HackSaw

    I’d hit it.

  22. rickardo

    I’ve seen her in real life, she’s weeeak!

  23. Snatchatarian

    Enough with the “ewww….bald beaver!….are you some sort of child molester??!!” bullshit. One can enjoy a “clean slate” and not be some fucking pedophile. Grow half a brain, you accusatory fucks.

  24. redpop

    I love a big bush!

  25. lol

    lol “the equiality process” or w/e is a fag or a jealous chick

  26. yay

    my tits look like hers! only maybe a bit smaller…

    “tits or gtfo”, i know i know

  27. yay

    ps. her vag looks so airbrushed, like it was painted on or something.
    not that vaginas dont or cant look like that, but doesnt it kind of look…drawn? it looks 2d. and the vag is ANYTHING but 2d. shaved or not, it looks like a babys vagina. or something done by someone who knows how to paint a babys vagina.

  28. Sponsored

    Governor Spitzer; You are forgiven.

    Who the fuck wouldn’t pay eleventy hundred big ones to pile on that.

  29. Joe

    She hottie

  30. Alan

    OMG!!!!!!!!!!!she is so hot and i thingk he will be an fantastic superhero he has the mucsles for it .Taylor is so hot and sxy in alll the twilights that i have seen so far and i think that he will be sxy in all of them.I saw him at a place ”—-plusflirt dot com —”,there are more handsome boys and big beautiful girls.

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  35. Bear hug

    I’m a girl (therefore I have a vagina) but I don’t understand what people mean when they say a vagina looks like a baby vagina. Because it’s shaved? Because she doesn’t have meat flaps hangin out? Thank you in advance for explaining this confusion to me.

  36. Ken

    She’s amazing!

  37. Jenn

    why does the writer always delete posts from the people that say he’s not funny? you over-sensitive hack, get a life. YOU’RE NOT FUNNY

  38. Fati87

    Don’t khow who she is but she is delicious!

  39. nothergirl

    I was thinking that myself, GIRL #44

  40. Julie

    Ha. This site is Drunken Stepfather lite.

  41. Gando

    Is her twat airbrushed? That doesn’t look like the average twat of an adult.

  42. Dave

    Amazing!!! —>

  43. cellphone

    And THAT’s why i like landing strips folks.

  44. Nero

    Usually i’d barely see the twat’s front.

  45. Rhialto

    Don’t tell me that a ten-year old girl is doing Playboy’s airbrushing?!

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