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by Izabella St. James


  11: In Da Clubs .

  “I drink to make other people interesting.”

  —George Jean Nathan

  Why, you may ask, does a seventy-eight-year-old accomplished businessman want to go out every other night to nightclubs with people a third, or even a quarter, of his age? Why would this inveterate jazz fan, who actually launched the Chicago Jazz Festival, subject himself to blaring, pounding hiphop music made by people he’s never heard of? How can he possibly get any satisfaction or pleasure out of this? Sure there’s the self-promotion angle—Hef is the living, breathing embodiment of the Playboy brand. Publicity is one of the main reasons he continues to go out. Everybody likes to be seen and noticed and catered to. But there is another motivation for going out: girls.

  Out in the clubs is where Hef can meet new Girlfriends—and he’s always looking. Outside of Holly and Bridget, he wasn’t really getting much action at the Mansion. And if he went out, then he could have an after-party in his room and invite girls back. And you’d be surprised how many girls we met who, inside of two minutes, would want to come home with us. They wanted to ride in the limo, go to the Mansion and drink champagne, and have sex with Hef. Most of those girls had the illusion that he’d make them Playmates if they slept with him. Many others wanted to become Girlfriends, but there were some who simply wanted to sleep with an icon or were just curious and sexually adventurous. And so it is not a coincidence that the two nights a week that we went out, usually Wednesdays and Fridays, were also the two “sex nights.”

  The night would start off with all of us meeting downstairs in the great hall. Most of the time, it was the seven steady Girlfriends (if we didn’t have seven official Girlfriends, then there were usually “potential Girlfriends”), as well as guests such as the girls who came to test for Playboy or girls shooting their Playmate centerfolds. The girls who came to shoot their centerfolds usually stayed in the guesthouse for a couple of weeks and were always invited to go out with us, and many times they ended up coming to the bedroom as well. Sometimes other Playmates came out with us; after her very public divorce, Shauna Sand came out with us regularly. I think she just needed to be cheered up.

  When we were all gathered and after taking pictures (the first of many pictures taken throughout the night), we would hop in our limo, where Hef would take pictures again. Our limo was awesome, a white Hummer with spinners, leopard-print interior with Playboy bunny logos sewn into the seats, Dom Pérignon champagne, apple martinis, and a booming stereo system. In the limo, Hef would also hand out Quaaludes to whichever Girlfriends wanted them; he always broke them in half so that the girls didn’t get too rowdy. Quaaludes were supposed to give you a nice buzz—make you feel like you had a couple of drinks without the bloating. The problem was that some of the girls would also drink, and the combination was toxic. I would always accept one from him because I didn’t want to seem like a party pooper, but I very rarely took them, and to this day I have some left over. Hef confessed to me once that they used to call them “leg-openers” back in the day, because they made girls feel horny. That explained a lot. On the ride to the club, things were usually tame in the limo; we were just listening to the music and having a drink, getting warmed up for the club.

  When we arrived and got out of the limo, an on-staff photographer and sometimes paparazzi would be there waiting and we would pose for pictures again. In the club, we would make our way to our usual roped-off area. We ordered drinks and scoped out the scene. I would laugh at Bridget and Holly’s dancing. I can’t tell you how many times girls came up to Emma and I and asked why, with all his millions, has Hef not paid for dance classes for Holly. The funny thing is that he did, but I think she took ’50s dancing (part of her plan to turn herself into Marilyn Monroe). Then there was Hef, so endearing doing the sprinkler and the shuffle, or pumping his elbows to the sounds of Eminem.

  Hef had a lot more energy than all of us when it came to going out frequently and staying up late. It was always us who complained about being tired and feeling run-down, never him. Going out to clubs was a blessing and a curse. If we did not go out to clubs, we would not see the world as it existed after 9 p.m. That is a weird thing for anyone, let alone young women who crave attention. On the other hand, the fact that we had to go out, always on the same nights and to the same clubs, did get a little tiring. There were certain clubs we went to that were cheesy Hollywood clichés—the ones that attracted the rich older men crowd, the men who thought that their money could buy them young girls, and often it did. The girls who attended these clubs were suited to these expectations. Then there were clubs like Las Palmas or Concord, which had hot, funky young crowds and cute guys. This was where we thrived. From behind the velvet ropes, we flirted as much as we could. However anticlimactic the situation might have been, it was all we could do, and it got us by.

  The thing that sucks about going out to clubs with Hef is that he gets comfortable with going to the same places for as long as they are operational. When I started out, it was Las Palmas on Wednesdays and Barfly on Fridays. After Las Palmas closed down, we alternated between Purple Lounge at the Standard, Ivar, and finally the Concorde when it opened. By the time Barfly closed, we were so sick of it. But Hef loved his Barfly. It was usually Emma who sat to the left of Hef, and then next it would be me and then Susan on my other side. We liked sitting on his left side because his left ear is the good ear, so it made talking to him much easier. Most people don’t know that he is deaf in his right ear, and there were many awkward times when he would turn his head so that they could talk into his left ear, but they didn’t get the hint and kept speaking in to his right; he would get frustrated and just yell, “I can’t hear you!” We always ordered this delicious thin-crust cheese pizza at Barfly (besides the previously mentioned edamame, it was the only thing he ever ate that was not prepared at home), and he always insisted on eating it and talking at the same time. Emma used to complain that he would spit little bits of pizza on her and, in fact, when I looked at her black outfit, I saw little bits everywhere. I laughed so hard. Next she noticed that her face would break out on the same side that he was sitting on and spoke to her from. Every time thereafter, when he started eating his pizza and turned to her to speak, we would just burst out laughing. She learned to quickly get up and dance. Needless to say, when Barfly closed down, Hef was disappointed. We started going to Bliss, but he would still reminisce about the pizza. Emma didn’t miss it.

  Most people think it’s cool to be in a VIP area, so exclusive that it must be marked off with that crimson velvet rope—we didn’t. Oftentimes, we felt isolated, and we took every opportunity we could to go walk around; Emma even pretended to take up smoking. We wanted to mingle, we wanted to flirt with the cute boys that would be staring at us from afar, we wanted to be young and wild. Eventually Emma did take up smoking at the clubs so that she could have an excuse to get away from the table and go outside to the smoking area, and of course Susan and I would join her. Or we kept going to the bathroom every half an hour and we would walk through the whole club to get there. That was our time to talk to guys and exchange numbers or make plans or whatever. And while our/Hef’s security was constantly at our side, waiting for us outside of the bathroom doors, they never reported to Hef that we talked to guys, and if they did, he never did a thing about it.

  Though it was nice to have the security most of the time, sometimes it was just too much. They were all cool guys, but we had too many with us all the time. Sometimes we would go to these small clubs and sit at the corner table or booth and they would line up around us like a wall. We couldn’t see a damn thing; people-watching was the reason we liked to go to clubs in the first place. Instead, on many nights we just sat there and stared at the backs of men in black suits. Wild times with Hef! It was ridiculous; you’d think the president was there instead of Hef. I couldn’t figure out the reason: was Hef in danger? If so, I would have liked to know about it.

  But who would hurt cute, little, aged Hef? Al
l of the men who saw him high-fived him and thanked him for years of good articles in the magazine. (Yeah, right.) It was always the same story: the son found the magazine under the father’s bed and then started his own collection, and of course Playboy was the first magazine that they all pleasured themselves to—or another heartwarming story like that. Out-of-towners and celebrity fanatics oohed and ahhed over Hef and the Girlfriends, asking him to pose for pictures, and sometimes an autograph, while security held them back. So if Hef was not in danger, why all the security? To keep an eye on the girls, of course.

  Ironically the only time the girls got into a fight, the guards stood outside of the ladies bathroom and did nothing. I did not go out that night because I had a cold, but apparently four of the Girlfriends went into the bathroom and some of the other club-goers—you know, the bunny-blonde haters—in there started provoking them, and they pushed one of the girls. So Holly and Tammy hid in their stalls while Emma and Susan kicked some ass. Security was nowhere to be seen. But thanks for coming out, guys! A couple of times, security did get into an altercation, which usually happened when some guy was trying to come past our velvet ropes, and the few times it happened, security got too rough. There were so many of them, and they are all strong and bored, so when a fight came their way they made sure to each get a punch in there. One time in particular, I remember we had a talk with Hef about the security being too violent. I don’t recall the details, but I remember one of the girls was crying because what she saw disturbed her so much.

  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). After that he would constantly check his watch to make sure we left at the right time because if we didn’t or the timing got messed up, he wouldn’t be able to perform later. We would leave between 12:30 and 1 a.m. This caused tension among Emma and Hef and Holly. Emma, along with Susan and I, wanted to stay and have a good time instead of leaving when the party was just beginning. Many times, we saw celebrities (usually the hot male ones) arriving as we were leaving, and we resented it. So many times actors or singers came into our area to say hello to Hef and to us, and then they would stick around and start dancing or talking to the girls (gasp). I would immediately notice Hef getting antsy and staring at them. “Oh no, he’s getting pissed,” we would say to each other. I thought he was so insecure and jealous about other men that he needed to be the only one with a penis in his zone to feel comfortable. When he could handle it no longer, we would hear him yell at his main security man, “Mark! Mark! What the fuck is so-and-so doing? Get him out of here!” And we would stand there mortified that the celebrity had heard and would realize how rude Hef was being. There were many incidents like that over the years. He would also get pissy when we were leaving a club. We had to line up like geese and follow each other out, but eventually, some girl along the way would stop and say bye to someone she knew and halt the line. Hef is known to push and poke the girls forcibly. I remember several girls being upset and embarrassed that he pushed them like that in public. When he didn’t get his way, things would quickly get ugly.

  Sometimes things got rowdy when we got back into our limo, depending on how drunk everyone was. Usually the girls who were testing for Playboy or the ones trying to become Hef’s new Girlfriends would take their tops off and Hef would take photos. They would start dancing, or giving other girls lap dances, which usually escalated into the girls kissing and fondling each other, to Hef’s delight. I didn’t participate in the debauchery; after the first few months at the Mansion, I never got drunk enough to do things like that. I was the jaded Girlfriend who had earned her right to just sit there and be entertained. And it was entertaining. Back in the early party posse days, it would go even further than that—the main Girlfriend would unzip Hef’s pants and pleasure him orally while the one sitting on the other side sucked on his nipple. I saw this a couple of times when I first went out with Hef, before I ever became a Girlfriend. I remember being stunned and feeling awkward, and some of the other new girls or girls testing for Playboy were completely disturbed. Sometimes we would get home before Hef and the participants realized it, and Hef would be zipping up his pants as security opened the back door. Eventually, I got used to it all and thought it was funny; I sat at the other end of the limo so I never got dragged into it.

  Another funny thing about the limo ride home was the selection of music. Sometimes at Hef’s request, Holly would play the “Face down, ass up, that’s the way we like to fuck” song just to get everyone in the mood. I think it was done to set the tone with the new girls. I was sick of that song after months of continuous play. I was tired of the lyrics and hated the beat to begin with—to have to listen to it all the time was painful.

  When we got to the Mansion, the Girlfriends would go to their own rooms to change into something more comfortable, while Holly would run a bath. Bridget usually “guided” whatever new girls came home with us, telling them what to do and how the night would unfold. Hef always asked Emma or Bridget to coach the new girls and encourage them to join him in the bedroom. The bedroom would always be prepared by Holly before we even went out to the clubs. She would lay out certain paraphernalia on the bed—toys, handcuffs, lubricants, whatever he had asked for or might come in handy. There would be porn on two screens the whole time—never unconventional or gay porn, contrary to one popular rumor I’ve heard many times. Maybe there was a time in the overindulgent, promiscuous ’70s when that happened and that is why the rumor persists, I don’t know, but I never saw any gay porn at the Mansion in the two and a half years I was there. Also, Hef never brought any men into the bedroom during the time I was there. It was only him and the girls.

  We would all meet up in Hef’s bedroom. The room is beautiful architecturally—all wood with carved naked nymphs. The bed is very large and sturdy, practically built into the wall. There is a back shelf (which holds many “toys”), a big mirror behind the bed, and one on the ceiling, and there are bookshelves and a magazine rack in front of the bed with the latest copy of a variety of magazines, everything from business to entertainment to tabloids. In front of the bed, there are two huge TV/projection screens side by side. There are pictures of Hef, his wife Kimberly and the kids, and all of his past Girlfriends covering the main wall (although right before I moved out, Hef said he was going to take down all of the family photos and put up pictures of the Girlfriends). There is a couch with stuffed animals—he loves stuffed animals—in front of a fireplace. There is also a winding staircase that leads upstairs to his office/scrapbook room and connects with the movie room and the video department. And last but not least, there was clutter everywhere: hundreds of videotapes, magazines, books, and gifts from people all over the world.

  This is the place where people think Hef’s deepest fantasies are played out. They imagine we’re all swingers and do all these wild things. That could not be further from the truth. First of all, I guarantee more scandalous and wild things happen at college parties than in Hef’s bedroom. I certainly had way more fun and learned much more in college than at the Playboy Mansion. Secondly, it’s not a free, uninhibited environment where anything can happen—regardless of what Hef thinks. It is a very structured setup. But you probably want details, don’t you?

  12: How to Make Love like a Rabbit .

  “Here am I: at one stroke incestuous, adulteress, sodomite, and all that in a girl who only lost her maidenhead today! What progress, my friends . . . with what rapidity I advance along the thorny road of vice!”

  —Marquis de Sade

  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 gift-wrapped goodie bag from his doctor at his annual Mansio
n birthday party—one of the first prescriptions written for Viagra in Hollywood. And the little blue pill does its job when duty calls, meaning it does get the penis hard. 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 he slept with would get yeast infections, which they blamed on the baby oil. (To this day, the smell of baby oil makes me gag.) Holly would start off the festivities by orally pleasuring Hef until he became erect. 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 hard, 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 then her, because the only other time Hef physically moved to have sex was for a particular scenario, and that scenario involved only her.

 

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