Kendra Wilkinson reveals details of her first sex session with Hugh Hefner (update)

LOS ANGELES, CA - AUGUST 15:  (L-R) Girls Next Door Kendra Wilkinson, Bridget Marquardt, Playboy publisher Hugh Hefner and Girl Next Door Holly Madison attend Playboy and Stoli's celebration of the September cover appearance and pictorial for 'The Girls Next Door' on August 15, 2006 at the Social Hollywood in Hollywood, California.  (Photo by Michael Buckner/Getty Images for Playboy Enterprises, Inc.)
Is there anything Kendra Wilkinson won’t do for money? She stripped for a living then moved in with octogenarian Playboy patriarch Hugh Hefner at the age of 18. She got married to a sports star, had a baby, and made a reality show so we could all revel in the details of her goofy life. She released a sex tape and then tried to act like she was upset that it was out there. She was upset that people realized that she was the one cashing in for a $680,000 initial payment plus 50% of sales.

Kendra, 25, now has a new biography coming out on Monday called Sliding into Home. Some of the tabloids have excerpts this week and it looks like an interesting read. The former Playmate and stripper has led a colorful life so far, but she seems to have a kind of emotional detachment from her past, as if she hasn’t really come to grips with it yet. She did some crazy and self-destructive things and she relates them with a sort of shrug as if she’s talking about someone else’s life, not her own. This is just the impression I got from the excerpts so far and what little I know of her personality.

Here are some excerpts, thanks to People and Star magazine.

On drugs, cutting herself, overdosing and ending up in a mental institution
The coke, weed, acid, crystal meth, alcohol and whatever pills I could get my hands on kept my mind in a haze. My mom was very worried. I felt terrible putting her through so much, but that didn’t stop me…

I’d take scissors and jab them into my arm, slicing until a stream of blood ran down to my hand. One day I went through the medicine cabinet and took everything I could find. My mom and grandmother rushed me to the hospital. The doctors made me drink pure charcoal….

For two weeks I stayed there [in a mental institution]. I felt like a crazy person. I got into a fight and they put me in one of those white rooms with rubber walls.

I heard somewhere that you could overdose on toothpaste, so one night I tried to eat an entire tube. Nothing can describe my pain during that time more than the fact that I tried to overdose on toothpaste….

On becoming a stripper after she quit doing drugs
I was feeling sexy because of the attention I was getting [for modeling at car shows]. I was eighteen. I thought, “I shoule be a stripper.”

For the first time in my life I felt sexy and powerful. I was the top earner in that club. But I thought I’d do even better if I were bigger. I worked for two straight nights to collect my boob job money and had them done. I had my dream boobs and business was good!

On having sex with Hugh Hefner for the first time
One of the girls asked me if I wanted to go upstairs to Hef’s room. In my head I could hear my mom’s voice: ‘You know they have orgies there.’ I said “Okay, if I have to.” It seemed like every other girl was going, and if I didn’t it would be weird.

One by one, each girl hopped on Hef and had sex with him… for about a minute. I studied their every move. Then it was my turn… it was very weird.

I wasn’t thinking about how much older Hef was – all the body parts worked the same. I wanted to be there.

On deciding to be Hef’s girlfriend
The next morning Hef came into my room to see how I was doing. Hef never went into the guesthouse. “Hello, my darlin'” he said. I felt special, loved and pretty. Isn’t that all a girl really wants out of a boyfriend?…

There was a world outside San Diego that I needed to explore – and I felt like Hef was the guy who would help me do that. Moving into the mansion when I was 18 felt like a spiritual event.

[Most text from People, print edition, July 12, 2010. More graphic details of sex with Hef from Star Magazine]

Star has more, including the detail that Kendra lost her virginity at 13. She writes that she called up a male friend of hers to do the deed and that his mom “dropped him off a boy and picked him up a few hours later a man.” Eyeroll! She also had a sexual relationship with a female classmate in high school. I’m interested to see if the rumors that Kendra and Bridget regularly got it in the mansion on are true.

Kendra has a very simplistic writing style that doesn’t seem to reveal much insight into her troubled past. I can’t hate on her, though. She cleaned up her act, changed her life and is now cashing in with her minor celebrity status. For all the do-nothing reality stars that are out there, Kendra is one of the least annoying and most entertaining. That’s really saying something.

Update: I can’t believe I reported this and just glossed over the part about all the nubile young ladies hopping on and off Hef’s elderly dick. This part seemed kind of obvious to me because I just assumed that’s what happened and had already read a similar account from a former Playmate. In fact Kendra pretty much confirmed what’s already been said. You can read all about it here.

MUNICH, GERMANY - MAY 31:  Hugh Hefner and girlfriends Kendra Wilkinson (L) and Bridget Marquardt attend a party May 31, 2006 at a nightclub in Munich, Germany. Hefner celebrated his 80th birthday with a party tour in seven cities throughout Europe.  (Photo by Jan Pitman/Getty Images)

42103, LOS ANGELES, CALIFORNIA - Wednesday June 30, 2010. Kendra Wilkinson and her husband Hank Baskett are spotted having lunch in San Fernando Valley. Upon arriving, Kendra could be seen adjusting the crotch of her trousers as her husband Hank wore a The Angry Beavers t-shirt, a animated show in the late 90's. Photograph: Juan Sharma,

42105, LOS ANGELES, CALIFORNIA - Wednesday June 30, 2010. Kendra Wilkinson and her husband Hank Baskett go for a job on a trail in the San Fernando Valley after having lunch together. Kendra recently revealed to People Magazine that she and husband Hank will be spending their 1 year anniversary in Seattle, where he proposed to her. Photograph: Juan Sharma,

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80 Responses to “Kendra Wilkinson reveals details of her first sex session with Hugh Hefner (update)”

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  1. heb says:

    Go Kendra!
    I don’t care about all the nasty things people say about her, I think she’s fun and I’m buying that book 🙂

  2. guesty says:

    kendra is just…kendra. thought there might be a confidentiality agreement where hef was concerned tho.

  3. Marjalane says:

    It took everything I had to click on this story. Seriously. Sex with Hugh? Shudder. However the first bit was well worth it: ” All the coke, weed, acid, crystal meth, alcohol and pills I could get my hands on” “MY MOTHER WAS VERY WORRIED”. Uh yeah, I guess she would be- she probably called you once or twice a week to lecture you on it. As funny as she can be in person, I think Kendra’s a nasty skank with maybe a single digit I.Q..

  4. mikaila says:

    Wow! They all hop on and hop off. I hope they changed condoms in between all of that hopping!

  5. Jack says:

    wow..just wow. i didnt know about her drug use and i kinda never thought that she had actual sex with hefner..
    hank baskett is way to good for her!
    simple fact: she is white trash, just look at her mother

  6. Leticia says:

    Wow, 13 years old. That makes me very sad.

  7. LOVE ANGELINA says:

    Gag Me!!!!!!!!!!!! OMG!!!!! Really bad mental picture. I never really thought Hef had sex with them. He is soo old. UGH!!!! He is to old. OMG Gag!!!!!!!!!

    I like Kendra as well. She was my favorite. I am glad she is in a better play. She and Hank seem really in love.

  8. DD says:

    I’m still grossed out about the line of women hopping on and off Hef. F’ing ewww.

  9. snowball says:

    “One by one, each girl hopped on Hef and had sex with him… for about a minute.”

    My little mini blueberry muffin and some coffee just came up a bit in my mouth.

  10. wtf says:

    disgusting. wow. all this time, didn’t she claim that she never had sex with hugh?

  11. Kitten says:

    It is cruel of C/B to post this early in the AM. At least let me get some food down first..

  12. Danielle says:

    “One by one, each girl hopped on Hef and had sex with him… for about a minute.”

    LOL Sexy stuff, huh?

  13. ligeia says:

    old news, howard stern described the whole how hef has sex with his bimbos ages ago. though i guess glad it’s confirmed? hurray for bimbo train…who is next?

  14. Electric says:

    o come on, does anyone really think that bag of rocks wrote a book? please. I don’t have anything against her, she actually seems like the most human of Hef’s girls…but she doesn’t have a lot in the brain department. of course someone else wrote the book.

    • paco manuel says:

      Exactly. If Kendra wrote a book, then Snooki must have completed a Doctoral Thesis.

  15. Trillion says:

    It all sounds humiliating, but hey, that’s just me. And moving into the Playboy mansion a “spiritual event”? WTF? What will happen to this woman when she’s no longer able to use sex to feel valuable? What then? More plastic surgery to fill the void?

  16. Tia C says:

    Wow, Hef must have a physician on staff to treat all the inevitable STDs. You know he’s not the only man those skanks are banging. Gross.

  17. margo says:

    I remember reading about those orgies in a book I downloaded was called “Hefnerland” by Jill Spaulding

    It details those gross bedroom scenes and the total lack of condoms, hef’s gay porn penchant,eeeew-I just remembered some more sordid details…too early, won’t go there!

  18. qb says:

    She is funny but I find her nasty and dumb.

  19. MSat says:

    I disagree about the least annoying part. I hate this hobag. I hate all those hags from that Hefner show. They’re glorified hookers and I wish they would all go away forever. She’s gross and 100 percent STUPID.

  20. kelbear says:

    I still think she is awesome, always was my favorite on girls next door.

  21. jane says:

    She is white trash! Dumb as a rock!

  22. EMV says:

    Her poor family and what she is putting them through and what she will be putting them through in the future…ugh

  23. Persistent Cat says:

    I’ve never seen that show or heard her speak, nor do I want to. Like someone else wrote, they’re glorified hookers. I don’t know how people can like her. Her face is so freakish looking, she’s clearly a complete idiot who’s self-worth is based on strangers thinking she’s pretty.

    And yeah, I think you can bash her for her “writing style.” That drivel got a book deal and was published. A 25 year old whore gets to humiliate her child. Again.

    Thanks for helping the woman’s movement.

  24. original kate says:

    “his mom dropped him off a boy and picked him up a few hours later a man.”

    i don’t think a real man needs to be picked up by his mommy.

  25. hottathanholywatta says:

    wow! I am sooo emberassed for her. Why rehash the past especially when it makes you look dirty and because you’re now doing it to make money. I would not stand for this if I we’re her husband

  26. Persistent Cat says:

    As for the title of the “book,” why a baseball metaphor? Are there no whore metaphors?

  27. skins says:

    You listening Hank?

  28. The Bobster says:

    The doctors made me drink pure charcoal….


    Kendra: From coal drinker to coal burner.

    Sex at 13? No wonder she looked so experienced at 18.

  29. okay.... says:

    I have a feeling that her hubby wishes she would just shut the door on her past and stop putting it out there for everyone to see.
    Stupid girl.
    Isn’t she the one who said she didn’t know how to mail a letter?

  30. Vajayjay says:

    All this b.s. she keeps pouring out is gonna come back and bite her in the ass.. It basically already is and her husband has to deal with it.. Then her poor little boy will deal with it when he’s grown. She should stop everything now, while she can, and live a normal life focused on loving and raising her son (and loving her husband).

  31. Leek says:

    Nothing says I respect my husband like talking about an ex-boyfriend’s ancient dick.

    I am in total shock that he really does have sex with these girls. I thought it was pretend.

  32. teehee says:

    I felt special, loved and pretty. Isn’t that all a girl really wants

    ^^ Seeking worth and love in the wrroooooonnnggg places.

  33. Marjalane says:

    I don’t feel sorry for her husband- the baby, yes- I saw the two of them on one of the tab shows and he was talking about how it was up to Kendra to start bringing in some money because his future was not looking so promising afetr he was cut.

  34. Cinderella says:

    Wow, times are tough if you have to make a living the Kendra way.

  35. jon says:

    this is f’in sick! hopping on and off some old, rich guy because he is famous. these women are hookers. no different. wait, I think hookers have the sense to use condoms and get the money up front…these skanks are lower than hookers.

  36. Kimberly says:

    I like her. She is not intentionally offensive. She is kind of refreshing!!!

  37. javagirl1 says:

    Hef is awesome! What a stud!

  38. Persistent Cat says:

    How is she refreshing?

  39. Katija says:

    “I got into a fight and they put me in one of those white rooms with rubber walls.”

    I started reading this in the middle and thought she was talking about the Playboy mansion. Which would have been AWESOME.

  40. sickofit says:

    i feel sorry for her. she must have had real problems at home when she was young.
    you dont do drugs and sex at that age when your family is a real home and you dont need to go for attention at a strip club with what age: 17?
    she seems to be bright but she needs to go to school or something, go get a bit of education, girl….

  41. mollination says:

    local radio station interviewed this trick and confronted her about the fact that she was a glorified prostitute and she got all pissed and hung up. They we’re as respectful and serious as possible about the queston – it pisses me off they won’t admit that.

    And gag me –> “I worked two straight nights to pay for my boobs”.

    NO! Not TWO whole nights of work!!! OH noooes!

  42. gee_gee says:


  43. Jeri says:

    mikaila: The article said he did not use condoms. That story grosses me out & if I had participated I would never ever talk about it. Eww…

  44. Tia C says:

    I also find her to be “one of the least annoying and most entertaining” of the “reality stars.” Her lifestyle certainly wouldn’t be what I would want necessarily, but her openness and honesty about what she’s done in her life could be considered “refreshing,” I guess. Each to her own.

  45. piedlourde says:

    So incredibly, utterly sad.

  46. Missfit says:

    She didn’t have to go up to that room to “f*ck” him, just because she didn’t want to feel “weird.” Well I would have preferred to have been the nerd odd bunch of the crowd instead of being a nasty whore and blending in with everyone else. Doesn’t mean you have to have that crack at the drugs to “be cool” then again, her dumb ass did go there and had her drug faze. I don’t get these stupid little girls having sex that young and most getting knocked up at that age too. I was still playing barbies at that age, geeze. I’m sure her man knew what he was getting into when he was messing with a playboy skank, they are all most likely the same. Hardly any of them are dignified ladies and most likely Hef has to take a tap at all those asses and most likely sleeps with girls under 18, he’s just about a pedophile.

  47. dj says:

    I agree Kimberly. I’m saddened by what kind of decisions she has felt compelled to make, at least she is admitting them and taking responsibility for them. Not pretending that all of a sudden she is an intellectual or getting a wax replica (for no apparent talent). She has pulled herself up and out of an unhopeful situation (suicidality), while her choices are not mine, I can appreciate the struggle. Unlike other reality stars she has had some hard knocks. That is refreshing and honest!

  48. Aspie says:

    She is absolutely disgusting. There’s nothing “cute” or “sweet” or relatable about her.

  49. shelby says:

    ha ha ha LOL am laughing and also grossed out about the line of chicks hopping on and off heff,its just foul but i cant stop laughing ha ha ha

  50. Ogechi says:

    Go Kendra darling…I can’t wait to watch your show tonight. I love u for real.

  51. Trillion says:

    She’s glamorizing and capitalizing on her tacky, stupid life decisions for our culture that has become increasingly hungry for vapid bullshit.

  52. carly says:

    She really packed on the pounds. She looks like a blonde midget in those jogging pics! lol

  53. Jenny says:

    her husband must be okay with it.

    also sounds like she has been through a lot of pain and suffering.

  54. lilkunta says:

    Early last year she said she never had sex with Hugh. That is was all for show. So now she did have sex with him?
    This girl is lying lying lying.

    I wonder if Hank is going along with this for the $. But it honestly doesnt bother him that not only does the whole world (especially his football teammates) see her naked from her pplayboy days, now they are able to watch her have sex over & over (& pre implant when she looked god) & now they will be able to read about her having sex.

  55. J.K says:

    I actually thot it was all fiction. I neva knew she was actually having sex wit that old fool who can’t kip his d*** lonely 4 once! She’s lucky 2 ve a husband who is undastanding.

  56. abby says:

    I thought she said that she has never seen Hef naked (like any of us wants to see that). Maybe she just didn’t take a peek when she was with him.

  57. Amy says:

    I doubt if she actually authored the book herself, she must have used a ghost-writer.

  58. Krista Jean says:

    The truth of the matter is…one never knows what they will do until they have walked in all of somebodys shoes. What happened to the golden rule? If you were Kendra how would you like to be treated? Everything is circumstantial.

  59. Krista Jean says:

    Why anyone would judge a person for being different is beyond me….and talking about her mother?? How would you feel if someone talked about your mom? Just because you were born into a different cast(so to speak)does not make you better. She can have sex with whomever she’d like…I don’t find her preference wrong. Really think about what actually makes things right or wrong…don’t just go by what someone told you. We all follow certain paths because it is what we know, but what if what we knew were different. Like cultures in third world countries. So relax a bit. Let people be who they are w/o acting superior!

  60. just my opinion says:

    Sad 🙁 she has a great husband a beautiful child, leave your past in the past kendra! why tell everything? poor Hank show some respect to Hank. It’s all about making money I guess.. Where is her mother now? help her make smarter choices lady! Hugh Hefner is a disgusting pedofile yuk just had to add that

  61. just my opinion says:

    forgot to add…kendra is very funny 🙂

  62. Issy says:

    It pisses me off that so many people are calling her dumb. The girl hasn’t had the same opportunities as most people here. She’s hardly been to school. If you read her book (before you started rambling on this blog) you would know she has a learning disability. You can’t possibly call someone with a learning disability stupid!! She’s obviously had a really hard life and still struggles with her dad abandonning her, not to mention her grandmother telling Kendra, SHE was the reason he left. It’s a lot for someone to take. Stop pretending you’re all perfect!

    • paco manuel says:

      Um no, actually the definition of dumb, is to have a learning disability, as you so aptly demonstrated. The girl is a moron. And her ability to make money has nothing to do with smarts, and all to do with a willingness to do immoral shit. I could choose to make money sucking guys off or selling drugs if I wanted to but I don’t, because I have values and self-respect.

  63. enticegirl says:

    you can’t call someone who knows how to make money stupid. nowadays it’s all about money and kendra knows how to make it. i mean, look at yourself. you say shit about someone and yet you don’t even take a good look at your own lives. why? are you successful? if those things happen to you, do you think the outcome would be the same? kendra rose above it all. could you? you see, people’s circumstances are all different. so don’t act like some perfect angel with a halo.

  64. Deb says:

    Seriously, the thought of sex with someone old enough to be my Grandfather makes me feel like I’m going to vomit. Kendra doesn’t seem to have much of a brain in her head or she would never have admitted this nasty nasty detail.
    She is just a child in a womans body.

  65. GAbbs says:

    Kendra is not dumb just because you think she is dumb because shes a blond stop stereo typing on blond Women Kendra is funny and sporty and she doesent want people saying this stuff about her BTW she is not a whore or a slut she has had some hard times in her life as she has said. I really injoyed the Girls next door. But Hugh hefner is a little over top with a girl sex thing ..

  66. Lindsay Joanne says:

    How does someone using the terms “whore” and “skank” have the right to make comments on the “womens movement”? Stopping the use of these terms may be your first step on the right path?? AS far as her right to talk about her past? If it were sunshine and lollipops would it validate discussion? Well guess what…grow up and feel secure enough in your own life that you can accept someone else’s right to their past and story. Kendra seems like a funny, pretty and secure young women who has more class in her pinky finger than some of the ignorant people commenting on here.

  67. jimjam says:

    that is one of the saddest things i’ve ever read. imagine what it would be like for things like that to seem normal to you.

  68. Pinky says:

    Kendra was never a Playmate, never a centrefold.

  69. They hop on,then they hop off.They’re called bunnies for a reason.

  70. Dani says:

    WHATEVER omg I rolled my eyes about 100 times reading all these comments.

    To start with who gives a toss about her learning disability? Half of my office are dyslexic and somehow still manage to work a normal 9-5 job like everyone else.

    If more women put their tits away and kept their legs closed men might start to take the rest of us normal women a bit more seriously.

  71. Brad says:

    I have read so many opinions and usually I do not comment. However, I am sadden by how many people want to put down someone else for the way they want to live their life. I will never stand in judgement over someone’s personal choices regardless if I agree or disagree with it. There are many things that most of us are ashamed of and are unwilling to stand in front of others and risk persecution. Kendra is willing to stand in front of society and proclaim her decisions whether you like them or not . I also can not get over how many comments that I am reading where as they think that it is gross for Kendra to have physical contact with Hef. Two consenting adults can do whatever they want…. Thank God for Freedom !!!

  72. Magic says:

    I love this story because it corroborates the story told by the former playmate years before. Hefner is basically a pimp. Not in a cool hip hop sort of way. Like a real disgusting pimp praying on young vulnerable women, who sometimes are poor and dumb/ditsy like Kendra.

    Obviously the girls are getting something out of it but it doesn’t excuse the fact he’s a disgrace. It’s a little upsetting that when he dies, probably heavily medicated mixed with some viagra, a random Playmate potential taking her turn on his ancient tool, while gay porn is on in the background, the story of his life won’t have any of what the man was really about. It will be this fabricated image he created.

    I’m not conservative in the slightest and I’m as open minded as they come. I don’t care if people want to be swingers, that’s their business. The one thing that bothers me are liars. Hugh Hefner isn’t a swinger, he’s a pimp, or actually a john I guess with a very large payroll.

    At least Larry Flint is upfront with his scumbagness.

  73. paco manuel says:

    I can not believe they blow that guy and let him stick his Dick in them. Really? Are they that money and fame driven? They talk themselves into believing they are attracted to him. So much for the girl next door.

  74. paco manuel says:

    Look, the bottom line is that anyone who goes to Los Angeles looking for fame has to do sick shit in one way or another to get what they want and most of them are
    Completely vaccuous and unscrupulous to begin with, worshipping only fame and money. And if not, they learn to be that way in time. The people who choose to say it’s not worth it, get back on the bus and move back to Kentucky. And that is what takes brains, being able to read between the lines of what people really want from you and what they are trying to do to you for their own sick gratification. It takes to effort to get sucked in because your a stupid twit. Just an ability to manipulated, to be gullible, and to conform. Be an individual. Don’t suck Hugh’s dick girls.

  75. Johns says:

    The women are just whhores (yes, with two “h’s”). They will sleep with a man for money and drugs. What is that? something for men to feel proud of getting? They’re not “getting” anything because these women don’t love Hef (or much older men). It’s just the money, and it is prostitution. nNothing more. Donald Trump, Hugh Hefner, clint Eastwood, and on and on. If these men were suddenly “broke”, do you think their young wives would stick around to take care of them? No, they wouldn’t. And as a woman, trust me, women who say they’d stick with a broke (and broken down) old man (who can’t even get it up to make love 9x out of 10), they are either prostitutes themselves, or looking for a Sugar Daddy (aka a “John”).