According to an authorized biography about Hugh Hefner’s life, the Playboy Mogul had some creepy sexual relations with his wife and brother.  Apparently Hugh got to boink his sister-in-law during a an unsuccessful attempt at a foursome between the two couples.

At first it started out him having sex with his wife while his friend poked his own wife on the same bed.  But then it got creepy when he involved his brother.

Hef then went further, trying a foursome out on his own family. “It did happen with his brother, Keith, and his wife, Rae, one evening,” Watts writes. “[But] while Millie ultimately backed out of having sex with Keith, Hugh slept with his sister-in-law.”

The book also says some dude went down on him once.

I’m all for people having foursomes if that’s what it takes to get off, but there is absolutely no reason to involve family.  I can’t even have sex in my mother’s house.  That to me is the naughtiest of naughtiest and I simply will not go there.

HUGH Hefner has gleefully enjoyed a sexually liberated life, but few know it all started with a little erotic dabbling within the Playboy czar’s own family.

In his upcoming book, “Mr. Playboy: Hugh Hefner and the American Dream,” Steven Watts writes how after Hefner wed his first wife, Millie, in 1949, he enlisted his friend Eldon Sellers, who would later help him co-found Playboy, into a staging a foursome.

The book relates: “One night after [Hugh] and Millie watched a stag film with Janie and Eldon Sellers, he suggested that the four of them make love on the same bed, each husband to his own wife. They did and in Sellers’ words, ‘It was different and exciting.’ According to Millie, Hugh began to hint at switching partners, apparently suggesting it with the Sellerses, although the swap never materialized.”

Hef then went further, trying a foursome out on his own family. “It did happen with his brother, Keith, and his wife, Rae, one evening,” Watts writes. “[But] while Millie ultimately backed out of having sex with Keith, Hugh slept with his sister-in-law.”

The book also claims Hef once tried a gay tryst. “Hefner’s thirst for sexual experience became so strong that he even had a one-time homosexual experience,” Watts writes. “One evening in downtown Chicago he was propositioned and, according to Sellers, he ‘thought, what the hell. Found it an interesting experience. As far as I know, the guy just gave him [oral sex].’ ”

Hefner also once shot a porno starring himself called “After the Masquerade.” Watts writes: “It was shot at a friend’s apartment where Hefner and a female acquaintance had sex while wearing masks.”

Hefner told Page Six he cooperated with Watts and gave him access to his personal papers. “This is the most authoritative book ever written about me . . . It’s all essentially true,” he said.

In the spirit of Playboy I thought I’d post the July photos of Cindy Margolis in the publication.  Unfortunately I couldn’t find them.  So here’s her last Playboy spread. Enjoy!

NSFW Playboy photos after the cut…

Holly Madison, Hugh Hefner’s go-to-Bunny, has been causing big problems on the set of The Girls Next Door. Everyone hates her. Especially Kendra Wilkinson. TMZ says

It’s gotten so bad, those two can’t be in a room for more than five minutes without totally going at it. And that’s posing major problems for producers of the show who have to shoot around the flying fur. As for Bridget, she’s Switzerland, often trying, but failing, to keep the peace.

Our spies also say Holly’s ambition is spilling over to the magazine too. She wants to have editorial control over the mag’s spreads — which is not going over well with longtime employees.:

I’ve never watched the show and I probably never will, but can’t this be solved with a naked pillow cage fight episode? Sure, maybe it won’t resolve ALL their problems, but it definitely will mine. My boner problem! Boooiiiing! Wait, no, just kidding. No boner problem here. Heh.

Hugh Hefner’s most annoying slut, Kendra Wilkinson, celebrated her 23rd birthday at Coco De Ville in West Hollywood earlier this week.

The Girls Next Door reality star was decked out to the max in L.A. Laker’s gear making sure to wear a low top in order to showcase her implants better.

Every time I see Kendra I cannot help but visualize a huge black penis inside her mouth. You know Kendra is all about the chocolate love.

I’ll bet my left ovary that once her Girls Next Door contract is up she’ll be dating a black Laker’s player with a two-digit penis.

I don’t know how girls screw men with 12 inch penises. My vaginal cavity must be really small because the one time I got with a guy sporting a ginormous schlong I wound up running a cold shower all the while grabbing onto my vagina while sobbing.

Bill Cosby quips that he gave up his dreams of becoming a professional jazz drummer and turned to comedy after seeing how easily the pioneer bebop drummer Max Roach handled rhythmically complex tunes that he struggled to get through.

“I finally went to see Max play and he played a song ‘Parisian Thoroughfare’ that Bud Powell wrote,” said Cosby. “Max sat there so relaxed and playing it like he was wiping off a table top or something. And I said, ‘No, no. I got to be funny.”

Despite that career detour, Cosby will be master of ceremonies at the 30th Playboy Jazz Festival on Saturday and Sunday — and he’ll get in some licks on drums with his band Cos of Good Music before thousands of people packing the Hollywood Bowl.

Cosby, 70, thought about retiring from his M.C. role when he skipped the 2005 festival, but he missed it so much that he was back again the following year. Now he’s instructed his agent not to book him anywhere else on the June festival weekend.

The comedian’s friendship with Hugh Hefner dates back to 1963 when he was making his Chicago nightclub debut and received an invitation to a party at the Playboy Mansion. Hefner had no trouble persuading him to host the first Playboy Jazz Festival in 1979 and he’s only missed three since then.

“We’ve been buddies since the ’60s and we both love jazz,” said Hefner. “It’s just a natural.”

Since 1995, Cosby has been performing regularly at the festival with Cos of Good Music, choosing the musicians and repertoire each year. He leaves the heavy lifting on drums to the veteran Ndugu Chancler.

This year Cosby plans to pay tribute to his fellow Philadelphian, Jimmy McGriff, who died last month, by opening his set with one of the jazz organist’s biggest hits, “I’ve Got a Woman,” which he describes as “a fast, popping, storefront church tambourine thing.” And he has selected the fast tempo “Limehouse Blues” to honor his friend Roach, who died last year.

Kendra Wilkinson, the dumbest of Hugh Hefner’s three girlfriends, celebrated her 23rd birthday on Tuesday at Coco De Ville in West Hollywood. And I for one am surprised that Kendra Wilkinson has been alive 23 years — and is still this stupid! Seriously, supporting the LA Lakers and Kobe Bryant? Go ho-me! Someone wrote:

“The Girls Next Door reality star was decked out to the max in L.A. Laker’s gear making sure to wear a low top in order to showcase her implants better. I’ll bet my left ovary that once her Girls Next Door contract is up she’ll be dating a black Laker’s player with a two-digit penis.”

With the Incredible Hulk tracking surprisingly well and threatening to smash Iron Man’s box office records next weekend, director Jon Favreau is keeping Tony Stark and company in the news by hinting at the plot of the Iron Man sequel.

When the original film made mention of the terrorist organization The 10 Rings, it was a clear reference to Marvel history and the alien artifacts The Mandarin discovered before beginning his career of oppression and supervillainy. It seemed like a pretty obvious clue from Favreau and his writers that Iron Man’s arch-nemesis would appear in a sequel.

Now, with the director saying he needs “heavy duty, heavyweight bad guys” to confront Iron Man in the next film, Mandarin seems all but a lock. There’s no mention of casting yet for the Far Eastern troublemaker, but that will have to break soon, as Robert Downey Jr. will be ready to begin filming in the golden titanium suit again when he finishes the Hugh Hefner biography he’s working on now.

A Hugh Hefner biopic, titled ‘Playboy’ is in the works and it is rumored that Hef would like to be played by Robert Downey JR.

The movie is about Hugh Hefner’s past and his life as a sexual revolution icon and the founder of Playboy. The film is being directed by Brett Ratner and produced by Ron Howard. Image Entertainment and Universal Pictures have teamed up to obtain the rights to 48 years of Playboy material for the movie.

Other rumored men to play the role of Hugh Hefner are Hefner himself, Tom Cruise, and Leo Dicaprio. Who do you think would make the best Hefner?

Don’t know who Ninel Conde is? If Hugh Hefner gets his way then you might know her soon enough.

It seems the 82-year-old Playboy Editor-in-Chief has taken a liking to the Mexican actress/model/singer after seeing a photograph of her. As a result of which, Hefner has offered the 37-year-old mother the coveted spot as a cover girl for an upcoming special birthday issue.

“Hugh saw Ninel’s photos and was very impressed by her assets,” a source close to Hefner affirmed.

Will Ninel take after the likes of Pamela Anderson and Kim Kardashian and become a household name? Only time will tell. But with that rock solid body and delicious tush, it doesn’t seem unlikely.

What do you say, would like to see Ninel Conde naked for Playboy?

When will she realize she’s not Marilyn Monroe? She looks like a damn fool in that dress.

Just take it off and show us your tits!

Here’s Hugh Hefner’s #1 girl, Holly Madison, at the 3rd Annual UHI Celebrity Poker Tournament in Beverly Hills Saturday.

Hugh Hefner is quite the dirty old man! The founder of “Playboy” magazine has extended an offer to Disney star Miley Cyrus to appear in the pages his magazine, but noted that the 15-year-old would have to wait until she hit the legal age. I’m not an expert on Miley Cyrus, but didn’t she make like $17 million this last year? I’m thinking she is not going to be signing up for this gig anytime soon.

Hugh Hefner said of the singing Miley:

“She would be welcomed in the magazine. Very pretty lady.”

Miley Cyrus Photos from Wango Tango: