The next day, Sunday, I headed out to the pool at the appointed hour. This pool was enormous, with a curving design and that lush California greenery around. Hef was already seated, playing backgammon with one of his friends. He was dressed in his trademark pajamas, and his main girlfriend was lounging in the chair positioned very close to him. All the official girlfriends seemed to have a certain order and positioned
themselves in an array around Hef. I walked by him and nodded my head in greeting. I sat by Michelle and her daughter up on the grass. She had brought her dog. Many new girls I didn’t recognize were in chairs by the pool. Kelly showed up and situated herself next to me. Her friend, Susan, who was a Sunday-guest, joined us. Michelle looked very annoyed that we had joined her.
I said quietly to Kelly, “We should move.”
“No. You picked the perfect spot next to Michelle. You want to stay in good contact with one of his girlfriends so that it appears you fit in.”
I thought, fitting in with what? I didn’t have sex with him. I just sat there because all of the recliners were spoken for, and I loved playing with Michelle’s dog because I missed mine. More people drifted in to play backgammon with Hef. He was completely immersed in the game, and there was no talking the entire Fun-In-The-Sun-Day, other than a few quick kisses from girls who were late or were new to the Sunday events. Hef didn’t talk to any of the girls. Two butlers were taking orders from the special Sunday menu. They were also photographers, and they took pictures of any girls doing something memorable. Kelly told me that if we wanted to get into the front of the magazine “Hanging with Hef” we had to flash and Fun-In-The-Sun-Day was the best time to do it. Okay, I thought. We took off our bathing suit tops and started rubbing oil on each other. We were perfectly positioned in Hef’s line of sight, able to distract him. It worked. He stood up and called for one of the men to start taking pictures. The main girlfriends were glaring at us. This was the only moment that Hef moved away from his game. We were proud of ourselves. Two other girls joined us, Bridget and Susan, and we all posed topless for the cameraman. Afterward I looked over and one of Hef’s sons was watching us. Then I felt horribly embarrassed. To top it off the other girl’s son was swimming in the pool keenly interested in the action.
“I’m surprised they let the kids out by the pool area on Sundays,” I said to Michelle. Realizing that Hef’s two sons, Marston, born 1990, and Cooper born 1991, were looking at us.
She shrugged. “They’re used to it. They don’t care.”
I looked around. Many of the girls were topless in the lounge chairs. I was shocked to see them uncovered. One girlfriend had stretch marks marring her breasts and was lying there naked. I was surprised that she would dare to lay out undressed. Otherwise the Sunday was very tame and unexciting. A few of the girls went down to the gym to work out and use the tanning beds. Kelly and I went out to the aviary and took pictures of ourselves with the monkeys, birds, and flamingos.
Brande Roderick was there, and she was swimming in the pool. I got Kelly to take a picture of the two of us standing near the pool. She was very thin and beautiful and seemed to be at home at the mansion.
When the afternoon drew to a close I went back to my room to start all over again getting dressed and putting on makeup. Buffet dinner and a movie were going to begin shortly. On Sundays was always to be first-run movies. I called Bruce. My rock was not so rock-like at this point. He insisted I come home. Over
the last few days he had said so many wonderful, supportive, and loving things to me. He had told me how much he loved me, how special I was, how proud he was, and how great my morals were. He missed me. He was lonely. I felt much loved and told him I would leave after the buffet and not stay for the movie. This seemed to relieve him. We hung up, and I started to redo my makeup for the night’s events.
The buffet was served outdoors. Mostly the same older people who attended the Friday night Fight Night were there. No celebrities; mostly just old friends and Hef’s current, and aspiring to be, girlfriends. I helped myself to more food than I normally would have since my figure wasn’t going to matter so much the next day. The desserts were wonderful—chocolate mousse, éclairs, pies and cakes asbeautiful as any you see at a high-class bakery.
I waited at the buffet area to tell Hef I was going to be leaving early.
I followed him to the pool bar and approached him slowly. “Hef, I’m leaving and just wanted to thank you for having me here.”
“Okay, dear. Wait right here a moment.” He headed back to the mansion.
I waited a little while and when he returned he handed me a stack of photographs.
I was so surprised. “Thank you so much!”
He looked at the bartender and asked him to take a picture of the two of us. I smiled and said,
“Thanks, Hef.” I headed back to my room. I had already packed. I told the valet that I was leaving and turned my key into the security room, and he helped me get out to my car. I drove out the back exit of the Playboy Mansion and watched it disappear from my rearview mirror. I headed to the casino and Bruce.
When I arrived, he was waiting for me out front. It made me feel good to see him, especially outside watching for me. The valet took my car and helped unload my luggage. Bruce didn’t seem glad to see me. I was puzzled and disappointed not to have been greeted with more enthusiasm. He did not even give me a hug, a hello, nothing, there was just silence. We went up to the room, and he wanted to be intimate right away. I was pretty turned off with the way he had met me, though I had been looking forward to sex when I had seen him standing out in front of the hotel. I told him how I felt. We talked for a long time, and it all worked out. I realized it was realistic for him to feel out of sorts over my stay at the mansion, and he realized that in my heart, I was still the same Jill Ann I always was.
We went back to Arizona, and I had to tell my mother and grandma the story about what goes on in the Playboy Mansion. All I ended up saying was, “They have sex with him, Mom—and all at the same time” I couldn’t say much else, because my grandfather was in the room, and I had to whisper what I did say as it was.
“So? What did you expect? What happened?” My mom was surprised that I thought it would be any different. “Only twelve girls get chosen. They have to stand out to get picked.” She seemed surprised that I thought it would be different and seemed to wonder why I did not stay. She knew how much I had wanted to be in Playboy—and she wanted it at my age.
“Mom, they don’t use any protection!”
“Oh, my God. Really? In this day and age with so many diseases? Well, I can understand why you didn’t stay.”
That was the extent of our conversation. My grandma told my grandpa that those girls probably have to have sex with Hefner to get into the magazine. She let Grandpa think she was guessing even though she knew the truth from me.
“Oh, Hugh Hefner has so many women there at the mansion they probably have sex all the time. He probably has orgies—just him and a whole bunch of girls.”
My grandpa replied, “No, he does not have orgies. That’s not how they get into the magazine. How ridiculous! What an imagination!”
Actually, I couldn’t have even imagined or thought up just how strange and treacherous it could be at the mansion
158 Bridget, Jill Ann and Kelly
Jill Ann inside Hugh Hefners office where he gives most of his interviews. Make sure to notice the picture of him and his wife and the bust of Barbie Benton.
Fun in the Sun Sundays with the Flamingos
Leaving the mansion after my stay. A few last pictures before I am on the road. This is the front door to the mansion. The famous stairs leading Upstairs is to the left when you enter.
160 Leaving the mansion after my stay. Posing next to the fountain in the front circular driveway.
Jill Ann feeding the monkeys.
Jill Ann feeding the monkeys.
Michelle with her dog out by the Mansion pool.
162 Hugh Hefner playing backgammon with some of his friends while many of the girls lounge by the pool.
Left; Brande Nicole Roderick Playmate of the Year 2001 and Jill Ann. Fun in the Sun Sunday June 9th 2002. Right; Jill Ann feeding the monkeys.
Left; Jill Ann holding a bird during "Fun in the sun Sundays." Right; Resident bird.
164 Posing in front of the Go Lakers Truck infront of the Commerce Casino after leaving the
mansion.
Go Lakers Truck in front of the Commerce Casino after leaving the mansion.
166 Go Lakers Truck!