Hef's Little Black Book (11 page)

Of course he did try it again. With Kimberley Conrad, whom he saw as an antidote to difficult times, a safe harbor after having ridden rough waves. He saw her wandering about his property, another lovely visitor staying in the Guest House, and he decided he wanted her as he hadn’t wanted any other Special Lady ever before.

“Despite the age disparity, we enjoy the same kind of life,” he had said. “She enjoys spending her evenings here with me and with friends and watching old movies and playing games and just being together.” On the night of July 23, 1988—six months after their first night together, when she had agreed to begin to get to know him—he led her out of the Game House, where she had just beaten him at foosball, and over to the wishing well, where he did what he had not done since 1948, with Millie. He begged her hand in marriage. And Kimberley said, “Do I have to answer now?” And his jaw dropped. But she recovered within seconds and said, “Of course I’ll marry you!”

The following July 1, they returned to the well and pledged their troth before friends and family. Then he became a father again, this time to two boys, Marston and Cooper, became settled and serene. But as these things happen, after ten years together, she somehow no longer enjoyed spending evenings watching old movies and playing games and experiencing the hurly-burly of Mansion activity—even though, as never before in his life, he remained true-blue faithful to her. So he bought her the
house next door, a two-and-a-half-acre property, and she and the boys moved. Not far, ever close and close to his heart, but moved.

He would say, “I think it’s clear that being married—raising children, settling down—is not the answer for everybody. There are alternate ways of living your life, very ethical and appropriate ways.” Meanwhile, he would have new romantic adventures to pursue, as only he could. He said, “If I had known what was waiting for me after the marriage, the marriage wouldn’t have lasted as long as it did.”

Making Love Like the Master

H
ow a sex god—well, how
the
sex god—became such: First, he was born into the most repressive of Midwestern households, wherein the subject of bodily functions of any sort incited great embarrassment. It was only during his army years that, at age nineteen, he learned to pleasure himself, an act that he had not yet fathomed to attempt. And so he came quite late to the party. There were females by then, and soon after, with whom he might have had his way, females other than the one he took as his fiancée, but he abstained conspicuously: “Although I’d had opportunities to go all the way with a couple other girls, I really didn’t want to have sex with someone that I wasn’t planning on marrying. In that sense, I was a very old-fashioned boy.”

At such time, in fact, there was no play at all in the boy, just abject conformity to a rigid society that had long vexed him. What vexed next: After he and Millie at last achieved clandestine consummation (the aforementioned holiday in Danville, Illinois, whose sole purpose was, in short, Let’s Get This Over With), and after she had graduated months before him to accept a teaching job elsewhere, she then proceeded to embark upon an affair with a high school coach. Once she confessed to it, Hugh Hefner’s view of sex shifted completely—which eventually shifted the course of American sexuality every bit as completely. She told
him it had happened just one time, which squashed his heart entirely, but he learned years later that it was ongoing until weeks before they were wed. Still, he would recall: “I never doubted that I loved her or that I wanted to marry her, but things would never really be the same again. I sat alone in my room and tried to make some sense of it all, playing Billy Eckstine records like ‘Fool That I Am’” Also, he said: “This was the single most devastating experience of my life, and in a certain sense, I don’t think I ever got over it.” But they married nonetheless, which was what was supposed to happen. And only then, suddenly stifled by constraints of career and household, unable to forget Millie’s indiscretion, objecting to a culture of sexual hypocrisy where blame was useless, because sexual adventure was forever to be the elephant in the room of life, he felt something snap inside, and he began to consider options, notions, possibilities, fantasies. He began to think randy thoughts he had not permitted himself to think before. High jinks ensued.

Other couples came to their stylish new apartment, whereupon he stylishly instigated new and extraordinary adult activities: “We’d play strip charades,” recalled his childhood friend Janie Borson Sellers, who with her husband, Eldon, showed up regularly. “We were all experimenting. We played strip poker, strip spin the bottle. We were all married, but it was very arousing. I remember one time we watched a stag movie, the four of us on their big double bed, and we decided to make love, each to our own partner. It seemed natural. Hef suggested it.” Said Millie, who gamely indulged the whims of her spouse, even though just a little concerned:
“He was the initiator of a lot of different things. Yet he was sensitive enough to know how to balance it with humor so that people would willingly partake. What he was reaching for was just under the skin of everybody, and he was the leader. I really had a sexual education and was probably lucky for having it. But I also thought, “There’s something wrong here when he needs to do all these new and kinky things.’”

Meanwhile, the leader himself would later proclaim: “It was the American fifties and I was suffocated and needed air. I was convinced that there was an exciting world out there and I wasn’t part of it. I felt like an outsider without any real connections to a world I knew only in books and movies. I didn’t want to grow up safe and sorry like my parents had.”

T
here Is a Message in a Bottle for You

T
he Female Body Is Aroused in More Than One Place

Once the magazine was up and running in late 1953, so too was his libido, as never before. “Sex in the office was commonplace,” he said. “We were on the cutting edge of a sexual revolution that wouldn’t really hit mainstream America until the mid-sixties. If Kinsey had done the research, I was the pamphleteer, spreading the news of sexual liberation through a monthly magazine—but also living the life as well.” (Paul Gebhard of the Kinsey Institute once admiringly noted: “Hefner’s genius was to associate sex with upward mobility.”)

Regularly, during staff meetings he would excuse himself when informed that a woman awaited him in his private office quarters. “Duty calls,” he would announce to his small band of employees, then go take care of business before returning to the meeting, where he had also been taking care of business. “We’d sit there waiting for him while he got laid,” said Arthur Paul,
Playboy’s
legendary art director, the man who also designed a rabbit-head logo that was to become instantly recognizable around the world. “We were envious as hell.” Thus, the editor-publisher was never especially circumspect about his early dalliances. Said the magazine’s first photo editor, Vince Tajiri: “I had the feeling he was proud of it, excited about making discoveries about sex. It liberated him. He was very open about it with me, which was surprising at a time when affairs were hushed-up experiences. I think he came to sex a little late, bumped into it, and then became obsessed with it.”

Well, yes. And this was good, he said, and this was correct, he also said (if conducted openly and honestly and lovingly, he always said; he would end his marriage in 1957, after sharing such open honesty), and this was only where it began, really. The fire burned hard from then on. Author Gay Talese, in his 1981 landmark exploration of American sexuality,
Thy Neighbor’s Wife,
described the life and mind of a forty-five-year-old Hefner, a Hefner who had by then slept with hundreds of nubile bedmates: “Each occasion with a new woman was for him a novel experience: It was as if he was always watching for the first time a woman undress, rediscovering with delight the beauty of the female body, breathlessly expectant as panties were removed and smooth buttocks were exposed—and he never tired of the consummate act. He was a sex junkie with an insatiable habit.”

Well, yes.

T
each Your Hands a Few Tricks

His hands would always be equal opportunity explorers, for certain. (It is said that his fingertips should one day be enshrined at the Smithsonian.) As the nineties dawned, however, a preponderance of silicone and saline graced his pages, and thus at decade’s end, his love life. Rare was the new Playmate whose décolletage had not been reconfigured.

T
he Handful Quandary: Real Breasts Versus the Enhanced Version

Incidentally, by the end of 2003, exactly six hundred Playmates had appeared in the magazine, wearing skimpy things and no things at all. Only because he was asked, he once said, “Just how many Playmates came to my bed over the years? There would be times, depending on what was going on, in which I would be romantically involved with maybe eleven of the twelve Playmates in a year. But of course there would be a time when ten went by and I wouldn’t be involved with any of them.”

To that end, this would be a good place to dispel one of the urban myths surrounding
Playboy:
the secret of the stars on the cover. “According to legend,” he would reveal, “the number of little stars on the cover of each issue was a code for how I rated that cover girl or centerfold in bed. The stars actually represented regional editions for advertising purposes. But the myth began in the early sixties and we didn’t attempt to discourage it. It had become so widespread that they satirized it on
Saturday Night Live
when I hosted the show in 1977. Sometime in the seventies, we discontinued the regional editions and the stars became unnecessary. And I said, ‘Just leave ’em on for a while.’ It had, after all, become part of the mystique.”

T
he More You Know, the More They Want You

L
acy and Racy Notions

B
edroom Accessories Never Hurt the Cause

He has always been legendary for his fondness for home gadgetry, and his bedroom has long known the purr of battery-powered foreplay, of pulsating electronically enhanced lovemaking. It was to be no other way. Plus, whenever the Bed was unusually crowded, the toys worked well to distract unattended-to participants. From one such participant: “Granted, when there are six girls and one guy,
what are you gonna do? I think a lot of us liked playing with the vibrators, and there were a lot of times that’s all you got.”