It’s weird, but I’ve always liked Hugh Hefner.

He’s kind of like this quiet, unassuming, kinky playboy who probably laughs as much as he screws. I respect that. He’s made a career out of vaginas and boobs, but he doesn’t really seem skeevy — at least at 80-Something. He seems cool. And really relaxed. Probably from all that screwing.

And while I can’t understand how he can tolerate those three chicks who follow him around everywhere, I do often wonder what life as Hugh Hefner is like.

Apparently, life as Hugh Hefner includes a foursome and a one-time tryst with a man.

Steven Watts, author of the new biography, “Mr. Playboy: Hugh Hefner and the American Dream”, reports that very early on in his kinky career (1949, to be exact), Hugh spent one night sexing his wife up next to his friend and his friend’s wife – who were sexing each other up on the same bed. Hugh wanted to switch partners that night, but no one was biting (metaphorically, of course). Later, Hef was finally able to attain foursome enlightenment – with his brother and sister-in-law (notice the italics. The italics symbolize my amazement that anyone could stand, let alone want, to have sex within inches of their sibling). Read More »

[Editor’s Note: New York Magazine does these Sex Diaries that are sometimes cool, sometimes lame. Sometimes they’re interesting portrayals of every day life, and sometimes they make it seem like EVERYONE in New York City is having copious amounts of crazy sex — which isn’t always the case, btw. What would happen, I wondered, if some of CC’s writers blogged about their sex life for a week? Would it be cooler? Funnier? More believable?

Let’s see…]

DAY ONE
7:05 a.m. Boyfriend wakes me up to kiss me before he goes to work, like he does every morning. Like every morning, I feel guilty about my morning breath, but he doesn’t seem to mind.
3:45 Boyfriend comes home early and suggests a quickie.
3:46 Boyfriend catches my unenthusiastic response and tells me never mind. I feel awful, as I do every time I turn him down, but I’ve been cleaning all day without a shower and I had just finished an hour of wii fit so I was sore. I promise him that I’ll make it up to him later that night.
1:22 a.m. Come home from seeing a friend’s band play. Still too sore and tired for sex, so I offer him a blow job as soon as we get home. Read More »