Few things are as nauseatingly disgusting to me as the thought of Hugh Hefner having sex. It’s not because he’s old – though that doesn’t help – but skeezy old men who classify their girlfriends (plural) by their hair color and rotate them as such really freak me out. Holly Madison – one of Hef’s current blond trio – has made no secret of the fact that she wants to have Hef’s baby. And I’ve gotta say that, although the idea of ever doing anything to a naked Hugh Hefner terrifies me to my very core – if she’s doing it anyway, birthing a little cash cow probably wouldn’t be the worst decision Holly Madison has ever made.

“There has been lots of trying — lots of trying!” [Madison] told Usmagazine.com at Playboy’s Ninth Annual Super Saturday Night bash in Arizona.

Hefner was tight-lipped when asked if they have plans to tie the knot. “There will certainly be a lot of romantic years ahead, but a wedding we will see,” he told Us.

Next up for the two: Valentine’s Day. “We are just going out to dinner,” she said. “I am trying to think of something creative, but at this point I am just going to save all of my ideas for Christmas cause Valentine’s Day came up fast.”

What does she hope Hefner will get her? “I don’t know,” she said. “I want like a house and a kid.”

[From Us Weekly]

A house is a pretty nice present – especially for Valentine’s Day. I’m pretty sure that if I asked any of the men I’ve dated for a house, they would have given me a lovely crayon drawing of said house. And considering all the conditions that I’m guessing would be attached to Holly Madison’s real estate, I’d prefer the crayon drawing. I guess a kid is a nice Valentine’s Day present if that’s what you’re really looking for. It’s probably not as awesome if it’s a surprise.

Picture Note by JayBird: Header image of Holly Madison (left), Hugh Hefner, and one of Hef’s other girlfriends, Bridget Marquardt at the E! Entertainment and L.A. Direct Magazine’s “Remember to Give Holiday Party” on December 13th. Note that Holly is holding an American Girl Place bag. That is some incredibly weird Playboy swag. Images thanks to PR Photos.

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.