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

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.

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