BY THE SIMPLE FACT that I was living at the Playboy Mansion, I became freer. There is this mystique, this aura of sexuality. It’s like the house fondly remembers the’70s, when sex ruled, and it tries to seduce you back into the swing of things. Even if a person is not that sexually open-minded, at the Playboy Mansion he or she can pretend to be. When in Rome, do as the Romans. We all explored the sexual side of ourselves; we played the role of sexy girls who love sex even though in reality that was not the case for some of the girls. Although fairly traditional, I am comfortable with my sexuality. I always have been. I think I am innately more lustful than romantic. It seems like lust is a natural aspect of being human, while romance is an engineered process, an enlightened and polite way of unleashing the lust. At the Mansion more than any place in the world, you can explore that part of your nature. But things are not nearly as wild as people imagine them to be, unless you consider two nights a week of structured sex to be wild and exciting.
The thing about the bedroom is, you’re not seduced, and you’re not always there by choice. You’re there because it’s a rule—an unspoken rule. I didn’t go in there for a long time, initially because I wasn’t ready to confront whatever awaited me. Hef was always cool and understanding and always repeated, “You’re more than welcome to come along, and you don’t have to do anything you don’t want to do. All the girls are clean, and we just have a good time.” The girls assured me that if I didn’t want to do anything I should just keep my panties on (that was a long-standing rule). Eventually my curiosity and drunkenness won and I went in. I kept my panties on for weeks and didn’t have to do anything but watch what was going on in this bizarre, wild, yet peculiarly structured world that was Hef’s bedroom.
The question that is on everyone’s mind: does Hef really have sex with all those girls? Yes. Yes and no. All the crazy things that you think happen there do happen there. There’s just so much more to it. Everyone knows that Hef is the self-proclaimed King of Viagra. Hef was introduced to “Vitamin V” one year on his birthday when he received a giftwrapped goodie bag from his doctor at his annual Mansion birthday party—one of the first prescriptions written for Viagra in Hollywood. And the little blue pill does its job when duty calls. Hef can and often has had sex with several girls in a row. How do I know? I have seen it many times, too many for my liking. But while I lived there, Hef was in his late seventies, and Viagra isn’t magic; it’s not like you take the pill and you all of a sudden become the world’s greatest lover. First of all, timing is everything. If the pill was not taken at an exact time in advance of the expected “performance,” then he would not be able to perform. Also, whenever there was stress or drama in the group (and trust me, this happened a lot), the blue pill could not do its trick; angry and frustrated, Hef would kick everyone out of the room.
When Viagra did work, it didn’t work alone. The bedroom encounters all started off the same way: 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 would get yeast infections, which they blamed on the baby oil. (To this day, the smell of baby oil makes me gag.) Holly, the No. l Girlfriend, would start off the festivities by orally pleasuring Hef. It seemed to me as if she never wanted to let other girls do it; I assumed it was a part of her plan of sexual monopoly over Hef, which was quite okay with all present. As soon as she got him aroused, some new girl would be ready to have sex with him. That was the thing about Hef; he was always on his back, so whoever had sex with him would have to get on top. I guess this was good because the girl was always able to control the length and the involvement of the encounter. Occasionally he would get up and get on top of a girl. It’s sad to say, but this usually happened when he wanted to have sex with some new girl who was shy or hesitant to have sex with him. He knew he would have to get up to get any action. This was rare, and though it used to crack me and my friends up, Holly’s blood boiled when this happened. She was jealous that he made an effort for anyone other than her, because the only other time Hef physically moved to have sex was for a particular scenario, and that scenario involved only her.
After the first girl had her brief session with Hef, there was a second and a third... and sometimes even a fourth would do the same. Finally, when it was confirmed that no one else wanted to “go,” it would be Holly’s turn to assume the position. However, by that time Hef was already limp and Holly would have to orally excite him and get him going again. I think it gave her a sense of power. Frankly, I thought it was disgusting that she would do that after all those girls (even if it was just one) were with him. Finally, Hef and Holly would have sex. Holly was always quick and full of moans and groans and “Oh daddy” shout-outs. This from a girl who would tell Hef that everyone else fakes it in the bedroom, and here she was, to me, the biggest faker of all. After that was the grand finale: Hef masturbated while watching porn, and Holly spread herself all over him so that no one else had physical contact with him during the moment of his ultimate ecstasy. He always masturbated, and it was always the same: too much baby oil, and the visual support of porn or the better alternative of a couple of the girls making out. It was all over with the loud, dramatic “God damn it... wow.” Lines we knew so well that we would laughingly mimic them exactly when they were being voiced. At this time, Holly would climb on top of Hef to snuggle and do some post-coital bonding to the exclusion of everyone (again, part of her plan of domination).
Some sort of a sexual relationship with Hef was inevitable for all of us, and the day my time came, I was ready. This man was sex personified; of course I had a desire to know what it is like to sleep with a man regarded as an icon of sexual freedom. I remember being curious to see if Hef was a good lover; age aside, I wanted to see if this experienced King of Sexdom knew anything the rest of us did not. But that inquisitiveness was pretty much over with the first experience.
Even though Hef might have sex with three or four, or sometimes even more, girls, it is important to realize that each of these experiences was brief. So truly and honestly to all the envious men out there: it all lasted as long as the time you spend (or should spend!) with just one woman. There are many people out there who think Hef has sex with several girls the way that they have sex with their sole partner, but it is not like that. The experiences are brief and uneventful—it’s almost as if he is doing it for show and for his ego. It is all an illusion; an illusion that he is still a swinger, a man with many women in his bed, a crazy orgiastic experience. It is just not so in reality. Many of the girls said he kept track of the number of girls and who he slept with every time. I thought it was ridiculous, but considering his egotistical obsession, it may just be the truth.
As all women know, a man’s sexual ability is best judged by the way he moves his body, whether on top of you or around you, the way he moves his hips, the way he lifts and moves your body. It is judged by the amount of time he spends pleasing you, his touch, his intensity, and his patience. Those things did not exist with Hef. It seemed to me he just lay there like a dead fish. Never thought I would say that about the icon of sexuality! In my opinion, Hef was not a good lover. No passion, no physical abilities, never a moment where I thought, Wow. Besides the lack of skill, there were also technical difficulties. He had a hard time getting aroused. When he did, it didn’t last long. Many poor girls had to revive his extinguished flame as it died in the middle of their time with him; such awkward moments killed whatever spark there may have been.
I never saw Hef use condoms. Period. He wiped himself off with a wet bath towel prepared by Holly in advance after he had sex with each girl and before the next; no, there was no germicide or anything but warm water on those towels! Doesn’t everyone worry about sexually transmitted diseases? Of course; that is one of the reasons I, and some of the other girls, never wanted to be intimate with Hef after we learned there was no protection. I can honestly say I have never had an STD in my life, but I know some of the girls at the Mansion did, and do, have baggage for life, so to speak.
WE OFTEN WONDERED WHY he did it at all. Why bother with this whole charade? The words of former President Bill Clinton come to mind: “Because I could.” Hef has the money and influence and charm to get this show to go on, but he must know deep down inside that it is just a show. Hef is trying to live out this fantasy he has been selling to people since 1954. He wants to live up to the Playboy image he created and the expectations people have of him; it wouldn’t be as cool if he slept with only one girl once every few months, like all the other 80-year-olds. Without the magazine and the wealth, Hef would not be able to attract all of these women, and without the Viagra, there would be no sex nights. In my opinion, Hef is not exactly the irresistible Casanova that he portrays himself to be.
The few times I slept with Hef, it was always brief and always the same. After a while, I didn’t bother. And the great thing was that he never brought it up to me like he did with some of the other girls. In my opinion, every Girlfriend played a different role in the relationship: Susan was needy and Hef liked that, Emma was fun and outrageous, Bridget had the same likes as Hef, Holly was totally devoted to him, Candy was easygoing, and I was the sensible one with whom he could talk about anything. Living at the Mansion was not about having sex with Hef. If it was, I would not have moved in, nor would I have lasted long after I did. My relationship with him was not based on that. He had a certain respect for me that allowed me to stay in the relationship without being intimate with him. I was the token “brain,” the token smart girl that validated the group in an intellectual way.
I don’t believe that many of the regular Girlfriends really wanted to have sex with Hef. Some of us always kept our panties on: in fact, we quickly adopted boy-shorts to make things even less intimate. We always had excuses; we had periods that went on for months, and when that excuse got old, we would suddenly get yeast infections. For all the people who speculate and wonder about how the girls feel, I think it’s quite simple really: I just don’t think many were attracted to Hef sexually.
Physically, Hef looks great for his age. His skin is surprisingly soft and supple and so white that he glows in the dark. He doesn’t have any weird veins or skin discoloration, and I would say he looks much younger than he is. All those years of being an eccentric hermit and workaholic, cooped up in his Mansion, have paid off for his skin. But for me, it wasn’t about the way he looked. I just did not have that close, passionate relationship with him, and so I did not want to have sex with him. That is the basic truth. But there were exceptions. Whenever any of the Girlfriends wanted something, he would use it as a major weapon: “You know, you girls never do anything in the bedroom.” He never mentioned it to me, but I would hear about it. It certainly contradicted what he told me at the beginning of our relationship, which was that there was no pressure to participate in anything in the bedroom. Sometimes Emma and I pointed that out to him: “We thought the relationship wasn’t about sex, Hef?” He would get all defensive and say it wasn’t. But we knew what he really wanted. Whenever a Girlfriend wanted something, she would have to participate more in the bedroom. Sex was a weapon, and it was skilfully used by both sides.
The majority of the time we were in the bedroom, it was not that exciting. We were there to unwind after a night out, to hang out while our alcohol buzz wore off, to see what new drama was bound to arise, and to meet his numerical presence requirements. We ordered drinks and snacks while he did his thing. When we were there, we would dance around on the bed and cheer him on as he had sex with whomever, or we did the pseudolesbian thing. We got a kick out of making him think we really did it with each other, but mainly it would be Emma plopping down on me and tickling me until I pushed her off me and pinned her down on the bed, or playfully smacked her around with one of the toys. We would get silly. Hef really got excited by watching two girls make out, and so to get a rise out of him, we would pretend sometimes.
Don’t get me wrong, there were times when the sexual vibe was real and strong. We would come home after a night of drinking and dancing, and all that sexual energy needed an outlet. When you have gorgeous young women who are comfortable in their own skin, with bottles of champagne, and surrounded by the mystique of the Playboy Mansion, magical things happen. Many times the other girls who would come up to the bedroom, in addition to the Girlfriends, were models and current Playmates who truly are into girls. When a beautiful Playmate of the Year is trying to climb on top of you and kiss you, and you’re already in that kind of environment, sometimes you go with the flow. It is a very sensual experience to be seduced by a beautiful woman.
I noticed that several times when a truly hot girl came up with us, it was because she wanted to be with the women, not with Hef. And that was fine with Hef. But he did get plenty of action from other girls. One time these two knockouts showed up from Australia, a married girl and her lesbian lover. They basically rocked his world—did all kinds of kinky things with him and had sex with each other so that he could watch. He seemed to become obsessed with them and their blatant sexuality; he eventually made one of them a Playmate and would have made her a Girlfriend, but then he found out they were also sleeping with one of the Playboy Mansion butlers and they got kicked out.
I remember a time when one of the Girlfriends started to caress me and kiss me and told me to remove my panties. I told her they were on for a reason, but she continued to try to remove them. I finally just said no in a blunt way, and she stopped. After the night’s activities were done and I was walking to my bedroom, she ran after me and started screaming that she was not a lesbian, that she was just trying to be nice and could not believe I was being so mean to her. I was dumbfounded, but wrote it off as her being drunk and high and continued to my room. Next thing I knew Hef was in my room to have a “talk” with me because she went to him crying that I rejected her. Now I was in total disbelief. A painful reality check: here I was, a law school graduate, getting a talk from my “boyfriend,” because one of his other Girlfriends was hurt that I did not allow her to pleasure me. I could have cried, but I started laughing. It was all so ridiculously absurd that it was actually hilarious. I told him I had my period, had my panties on—as per the obvious rules—and I wasn’t in the mood. Heaven forbid someone not be in the mood at the Playboy Mansion! The truth was she and I had fooled around on other occasions, and I was attracted to her inasmuch as I can be attracted to a girl. I let her suck my toes a few days later, and she got over the rejection. She was the only Girlfriend I ever did anything with.
Months later, a new girl joined the group who also seemed legitimately interested in girls, and she had a thing for me for the longest time, always telling me how she was going to “get me.” Emma and Susan thought it was funny and kept telling her I was ready for her, which of course was not true, so then I had to hide and avoid the girl. I did not think she was an attractive girl in any way; in fact, I was surprised she became part of the group. But she was one of those quiet, nice girls who didn’t ruffle anyone’s feathers, and Hef let her stick around. One night when I was really drunk, I let her kiss me and it was terrible. That was it for me. I had my few experiences with gorgeous models, and I had to close the chapter on experimentation with girls while the memories were still pleasant and erotic.
WHY DID I HAVE SEX WITH HEF? The main reason, if there must be a reason, was the fact that I did have a relationship with this man. And there were many times when I had real feelings towards him. Besides the feelings of gratitude, there was also appreciation, respect, and a certain type of love. Not love in the raw sense of true, complete, infinite love. But a love in the sense that you care about someone and what happens to him. There were times when he and I would discuss business or world events and I appreciated his perspective. I loved hearing about the early days of Playboy magazine, his trials and tribulations and successes. I tried to learn what I could from him. More than anything I liked when he joked around, when he was silly, especially when he did his dolphin sounds. He was human then, he was lovable. I was also proud of him; I remember when an African-American jazz musician spoke about what Hef did for him and other musicians by having them perform on the TV show Playboy After Dark and at the Playboy Jazz Festival, I could not help but feel pride and joy to be associated with this man. These were the times that I recalled my initial fascination with him—the man who founded Playboy magazine and revolutionized sexuality. I looked up to him, and there were times when I felt connected to him.
The problem with the relationship was that there was no intimacy. There was no alone time with Hef; therefore, nothing felt personal. And the sex, more than anything, was impersonal. The few times it did occur, it was in front of an audience and it was brief, no longer than a minute. We never really kissed Hef either; most of the time, it was just a peck on the cheek or a goodnight kiss on the lips, which is not a big deal considering everyone kisses Hef on the lips—female friends, Playmates, any female acquaintance. French kissing between Hef and his Girlfriends was rare; if it occurred, it was mostly in the bedroom. I love kissing; it is my favourite thing to do, and it was just another thing that never happened in my relationship with Hef, and that contributed to the lack of intimate feelings in me toward him. While I lived there, he never came to our rooms to spend time with us alone, one-on-one. It is unbelievable to think that in two years of living at the Mansion, I have shared less than fifteen intimate minutes with Hef. But it is true. And so even if the feelings going into it were genuine, the experience did not feel like it was. Maybe because having sex with Hef was part of the unspoken rules. It was almost as if we had to do it in return for all of the things we had, for sharing his life at the Mansion. I think in his eyes, it was the only way we had of showing our gratitude for all that he did for us. But expectation becomes an obligation, and obligations are not performed out of desire but out of duty. And when I look at it that way, it makes me resentful and makes the whole thing ugly and meaningless. In the end, it always left me with conflicted emotions.
The Mansion has the aura of being this free, uninhibited place, where you are more than welcome to expose your sexuality. You are free to be your true sexual being. And maybe it was like that in the ’70s and ’80s before Hef got married. But it is not so anymore. There are too many unwritten rules, too many power plays, and everyone acts.
Enjoy more great stories from The Maclean’s Archives. Start your 30-day free trial today.