Ex-playmate reveals nasty details of Hugh Hefner’s sex sessions

An ex Playmate has self-published a book about what goes on at the bizarre sex sessions at the Playboy mansion. She says that if you’re a hot nobody and want to get into Playboy without riding the then 78 year-old Hugh Hefner’s six inch Viagra erection, you can forget about it.

From her description, Hefner’s evening sex romps sound more like a freaky ritual than a fun-filled free for all. Here are the highlights:

  • Women who live in the house must show up for Wednesday and Friday sex night. They are given rare exemptions in the case of major surgery (like a nose job), but if it’s that time of the month or they’re sick, they’re still expected to come. Even Hefner’s secretary has to participate.
  • Hefner invites women into his lair. The night the source was there, 12 women were in the room. Each must bathe and wear identical pink pajamas. If they don’t want to have sex with the 78 year-old perv, they can leave their pajama bottoms on.
  • Gay porn plays on two big screen TVs in the room.
  • On the night the source was there, Heff got a hummer from his current girlfriend to start the action. 10 of the 12 girls then took turns having sex with him, taking about two minutes each while the other participants cheered him on. He took Viagra to perform and did not wear a condom.
  • Women paired up for simulated lesbian sex for Heff’s benefit, but according to the source most of them weren’t into it and didn’t even like each other.
  • The session ended with him having anal sex with the girlfriend, who wiped off his penis beforehand, as if that did something to prevent STDs.

In terms of what sex with Hef actually entails, it sounds like it’s strictly women on top:

How is a man who’s 78 years old able to have sex with that many women?

He doesn’t really do anything. He just lies there with his Viagra erection. It’s just a fake erection, and each girl gets on top of him for two minutes while the girls in the background try to keep him excited. They’ll yell things like, “F-k her daddy, f-k her daddaddy!” There’s a lot of cheerleader going on!

Playmates are discouraged from talking about Hefner’s orgies through ongoing business deals with Playboy enterprises, including invitations to parties and ex-playmate get togethers, where they are paid for their appearance. There’s a code of silence around it because to reveal details would jeopardize their future earnings.

Strippers and lesser known porn stars get in Playboy by sleeping with Hef in these prearranged orgies, and the source claims that no woman has ever made playmate of the year without playing along at the sex sessions.

It looks like the answer to Bastardly’s question “Would you sleep with a dude the age of your grandpa for $3,000,000?” has been answered by a lot of the Playboy playmates, who would do it for fame and much less money.

Update: Hugh Hefner is just shy of 81 at this point, as commentor Jenna points out. He was born April 9, 1926 according to Wikipedia.

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31 Responses to “Ex-playmate reveals nasty details of Hugh Hefner’s sex sessions”

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  1. mimosa says:

    I actually have that e-book. I didn’t care too much for it but she does have pics included of her time spent at the Mansion (nothing scandalous). If anyone wants a copy, let me know.

    That Jill Ann (the author of the book) never made it as a Playmate bc she wouldn’t sleep w/ him.

  2. frewtloop says:

    I’d vomit if I wasn’t laughing so hard.

  3. Miss Mya says:

    I would love a copy of the book. I have just finished ‘Bunny tales’ which basically says the same stuff except the gay porn part. Go Heff! If you still girls wanting you at 80 then go for it I say! I hope Im still at it then too!!!!

  4. mandi says:

    I want to say that Hef’s a dirty old man, but at the same time, these women are stupid for being willing to take part in it for the fame.

  5. mimosa says:

    Miss Mya, email me at mimosapop at yahoo . com and I’ll forward you the e-book.

  6. xiaoecho says:

    Nothing that Marilyn Monroe didn’t do to get an entree into the biz.

    gotta feel sorry for Hef..a real renaissance man..not!

  7. Lady Metal says:

    Hey, Mimosa, I want a copy!

  8. vdantev says:

    I imagine having sex with The Hef sounds alot like corduroy pants rubbing together.

  9. Bex says:


    That’s all..

  10. Jenna says:

    It sounds like a bunch of chicks doing what they have to do to get what they want. Not that I agree with it, then again I have no desire to be a Playmate either. At least it only lasts for two minutes….;)

  11. Jenna says:

    And I forgot….are you sure he’s only 78? I coulda swore I heard something a while back about his 81’s birthday party.

  12. Husband says:

    Thanks Jenna! According to Wikipedia, he is 80 and will turn 81 this April. I will update the post and credit you.

  13. Gigohead says:

    A few years back, my boss was approached to doing investor relations for the Playboy company. It’s a publicly traded company. I can understand why most folks won’t put their money into this stock. It’s cash for all of Hugh’s concubines. Please..all these gals are pulling a “salary” to bang the old man.


  14. alexi says:

    Nothing like paid prostituion right? Listen, Hugh is most straight men’s dream life…Altho why the gay porn? He must be bi. I get sick when all these girls say how much they love hugh. They love the mansion, the diamonds and the money. I dont’ care about who sleeps with who – but HIV is a factor if you have an ounce of self respect these ladies or Hugh would wear a condom. Oh – then of course they would need self respect!

  15. Fleegle says:

    Probably female gay porn – what else?

    This whole thing makes me ill and sad. It’s abuse and the women all need therapy.


  16. Jenna says:

    Hehe…I’m famous 😉

  17. Other Karen says:

    Two minutes each? Awfully unsatisfying for the girlfriends, considering they don’t get laid for the rest of the week. But he pays for their educations. That’s something, I guess.

  18. suki says:

    I knew I shouldn’t have read this one. I’ll have to scrub the mental image away if I ever want to have sex again. Ugh.

  19. Adrienne says:

    No way this is true…NO WAY!!! Playboy seems to be an org that helps women become successful, not turn them into sex slaves. Sorry, this is fiction.


  20. ThisGirl says:

    Sick, and doesn’t surpise me the least. I pity those girls. They chop up their bodies, bleach their hair to a VERY unnatural blonde, and for what? Money and sex with a dirty old man? SO not worth it.

  21. mimosa says:

    Well I don’t know if the details in these books are true or not but until I read it I had assumed he had one “real” girlfriend (Holly) and the other girlfriends were just a part of his image, like Mickey Mouse and Donald Duck are apart of Disneyland.

  22. FogCityKitty says:

    The book is available for free at:


    It’s not very good, and remember that this masculine woman was only at the Mansion for a few days.

    Much of what you read is true, and is confirmed by much more reliable sources.
    Izabella St. James book, Bunny Tales is much much better-but it has much of the same lurid type of stories about her as a live in girlfriend.

  23. mimi says:

    I have read somethings about their sex nights. FRom what I read, I gather that the women have to bath in hugh’s bathroom and then put on the outfit (keeping your pants on means no sex)Each girl gets a toy for herselve and they just take turns with hugh hefner(no condoms though)THe no condom thing is what grosses me out, the rest is just stuff that I figured went down out the mansions with all his girls.

  24. Azraelle says:

    I could swear Hefner is 80 or 81. Also, isn’t Holly the one who shares a room with him? She’s older than 22!

  25. Marianne says:

    It’s true…an aquaintance of mine was in Playboy in ’05…she slept with Hef twice…once in the grotto, once in his bedroom. In her case, the other girls told her to leave her panties on if she did’t want to have sex. Her story depicted power strips filled with sex toys too. Gay porn was never mentioned. Girl on girl action was mentioned. Oh yes, and Hef DOES have unprotected sex.

  26. catty says:

    I worked with a playboy playmate once, and when we out after work, she was drunk and she started talking. She tells a very similar tale, so I don’t think Jill Ann is lying.

    The part that bothers me is women getting horrific infections and bloody pee because wiping off with baby oil after each woman = tons of nasty bacteria into your vag = UTI/kidney infections galore. UGH.

  27. TT.Quick says:

    I don’t believe the “all PMOY’s Playmates had sex with Hef” thing..I know a former PMOY, and she would have told me! So don’t think it’s true – believe none of what you hear and half of what you see!

  28. DivaStar says:

    mimosa I also would like a copy of the book gemstone1966@yahoo.com thank you

  29. Oscar says:

    Sounds like Hefner fits the definition of “pimp”. Has he ever been charged with ‘living off the immoral earnings’ or whatever the equivalent is?

  30. liz says:


  31. ktdesigner says:

    Can I have a copy of the book too!? The link must have been taken down because I cannot download the PDF.