But Hef, What About Holly Madison?

With the news that Hugh Hefner, 84, became engaged to his 24-year-old girlfriend, Crystal Harris, over the holiday weekend, we’re left thinking about his former-number-one girl Holly Madison, and how she got fucked in the ass—figuratively and literally.

During the seven years that Holly and Hef were together, she had to endure his revolving-door-harem-of-blondes phase, which ultimately led to the more stable polyamorous setup involving Bridget Marquardt and Kendra Wilkinson that was documented on the E! series Girls Next Door. One of the main plot points of that reality show was Holly’s desire to marry and have babies with the Playboy founder. This dream of hers—to start a family with a wealthy octogenarian—brought on accusations of being a gold digger. But if there’s gold to be had, we say give it to her—she earned it, after years of Viagra-induced butt sex.

There are several accounts of what intercourse with Hugh Hefner is like—from ex-bunnies and ex-girlfriends (Kendra Wilkinson)—and they’re all basically identical, from the baby oil to the wipe-off cloth. But ex-girlfriend Izabella St. James’ description in her memoir Bunny Tales is perhaps the most detailed, when describing Hef’s sexual relationship with Holly:

At around midnight, Hef would take his Viagra; it was always wrapped in a crumpled Kleenex (although Holly bought him a nice Tiffany pillbox once, he always stuck to his habits).

Hef would lie on his back in the middle of the bed, and as some of us were getting stoned or drinking Dom, he would cover himself in baby oil. Many of the girls he slept with would get yeast infections, which they blamed on the baby oil…Holly would start off the festivities by orally pleasuring Hef until he became erect…when it was confirmed that no one else wanted to “go,” it would be Holly’s turn to assume the position. (That appeared to be the distinguishing mark of the number one Girlfriend—not only was she the only one who had sex with him regularly, but she was the only girl that ever had that particular kind of sex with Hef.) Holly was always quick and full of moans and groans and “oh daddy” shout-outs. After that came to the grand finale: Hef masturbated while watching the porn, and Holly sucked on his nipple.

And despite her efforts in the bedroom and beyond, Hef never really took Holly all that seriously. In fact, the entire time they were together, he refused to finalize the divorce of his marriage to Kimberley Conrad (which he finally did in March 2010). In 2008, after seven years with Holly, Hef said, “I love Holly very much and I think we’re going to be together the rest of my life, but marriage isn’t part of my puzzle. It’s not a personal thing; I just haven’t had much luck with marriages.” A couple months later, she left him. But before she’d even moved all of her stuff out of the mansion, he had already lined up his next chippies, one of them being Crystal.

To add insult to injury, Hef got a little snippy in his post-Holly interviews, saying, “[With Crystal Harris] I have found the relationship that I thought I had found with Holly. In retrospect I do believe in the most recent years, I was without being aware of it, starting to look for a more serious one-on-one relationship.” And it seems he has. He announced on his Twitter account that he gave her a ring and everything. (Holly has yet to respond to the news on her own Twitter account.) It’s a classic case of someone reaping in the benefits of someone else’s hard work: These days, Hef doesn’t even take his Viagra that often, as it can lead to heart problems. So one might assume that this new girl Crystal has—in the two years that she’s been dating him—only been subjected to a fraction of the baby-oil horror show that Holly had.

But, in the end, Holly seems happy, living it up in Vegas with her own TV show, live burlesque show and paid promotional appearances. She may not have achieved her long-term goal of being Mrs. Hefner, but on the bright side, she doesn’t have to straddle a lubed-up old man anymore.