Dirty Dozen: Cindy Margolis
I would have been the biggest slut.
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MILF. Cougar. Internet queen. Cindy Margolis, a former Barker's Beauty on The Price Is Right, is sexy and single and ready to mingle. The buxom blonde, who's singlehandedly changed the way men look at women over 40, became the most downloaded woman on the Internet in the '90s, thanks to accolades from AOL -- and before celebrity blogs even existed. She also held the Guinness Book of World Records title, with reportedly more than 70,000 downloads in a 24-hour period. "To be able to do all that, for being the girl next door, was a great achievement for me," says the two-time Playboy magazine cover girl who once famously dated Friends star Matt LeBlanc but never slept with him. "I thought I would be the one out of a million girls who doesn't sleep with him, because that would make him want me, but it backfired," she says. "If I could do that again I would've slept with him in a second."
Surprisingly, that's not Margolis's only regret. Before her July 2008 issue hit newsstands, Playboy spoke to the newly single mother of three about her six-month dating dryspell, why sex only gets better with age and her ultimate sexual fantasy.
1. Your lingerie collection puts Victoria's Secret to shame. What's your favorite thing to wear to bed?
Cindy Margolis: I don't wear lingerie to bed by myself. But every time I am with a man, definitely. Every time for 10 years with my ex-husband I never once didn't dress up for him. Now that I sleep alone, I just wear a big T-shirt and -- I hate to say it -- sometimes my granny pajamas. When no one's around I can be a slob with my zit medicine on. But hopefully I'll find a man who loves me like that too.
2. This is the first time in your life you've been single. How many men have you slept with in your lifetime?
Margolis: I've been with more than you can count on one hand, but less than you can count on two. But I will say, looking back, if I could do it all over again, I would have been the biggest slut. I wish I could tell you I was in double digits or triple digits.
3. How old were you when you lost your virginity and what were the circumstances?
Margolis: I really wanted to lose my virginity to my first love. The first time I saw him it was the first day of school -- I was in 10th grade and he was in ninth; my first younger guy! I loved him all through high school. However, he was too cool for me and only dated much older girls. It took me three years, but I finally got him. When I told him that I saved myself for him, he was only too happy to be my first. I was 18 years old and the last one of my friends to lose my virginity. I was hoping to lose it on prom night, but my date got drunk and threw up all over me! After that neither of us were in the mood. So it happened in my bedroom at my house. I had this romantic notion that I wanted it to be in my own bed where I had dreamt about the fantasy of it so many times.totally forgetting that my mom's bedroom door was right across the hall from mine. I kept thinking she was going to catch us, but she didn't.
4. You've always dated younger guys. Why are younger men better in bed than older men?
Margolis: Well, I've never been with an older man, but it all depends on the guy. I haven't had that much experience. With younger guys, most men want to please you, which is really nice. But I love pleasuring men. I am 100 percent a giver. I think that's what actually blows most guys away.
5. What's your favorite sexual position?
Margolis: There's fucking and there's making love. I don't think many men know what making love means or how to do it.
My favorite thing would be to actually have someone make love to me, but my favorite sex thing to do -- I love giving blow jobs. I'm a romantic. I'm a very generous lover. I love to give pleasure to my man. I want every kiss that I give to his lips, and the rest of his body, to be the most passionate experience he's ever had. I also want my man to love to please me too. I want our hot sex and the all-over body kiss we share years from now to be just as exciting as the first blow job I gave him.
6. Does sex get better with age?
Margolis: Abso-fucking-lutely! Guys will say that any time they get to have sex is "good" sex. If a guy is lucky enough to have sex with a 22-year-old girl, and then gets to have sex with a 35-year-old woman, there is no doubt that the 22-year-old hottie may rock his world, but the 35-year-old sex goddess will blow his mind, take him places he's never been and have him begging for more, more, more! The more you have sex, the more you love it. I am way more open with my sexual desires, way more comfortable with my body and I know what pleases me, and I'm not afraid to tell the person how to please me. Plus, let's not forget about older women hitting their sexual peak!
7. How many orgasms have you had in one night?
Margolis: In a session would be five. If guys just knew how to please a woman, and if you're woman enough to tell them how to, then you can achieve that. It's really up to the woman to be able to do it -- it's not really how skilled the man is at all. Every woman's body is different, and you need to tell them what pleases you. I would not blame the man if I didn't come.
8. Where's the craziest public place you've ever had sex?
Margolis: Trying to get pregnant, we had sex every place possible. We went on a 14-day marathon. I had sex on our honeymoon on the beach, in the water, in the pool, in cabanas, on balconies. I've had intense, long sexual marathons when we were trying with the three kids. We've had sex at a Madonna concert; in the car, I've had sex while the guy is driving, and I was on top of him. It was fun, but when it ends up being about only trying to have a baby, then sometimes it's not so fun.
9. What kind of music do you like making love to?
Margolis: I have a special sex playlist on my iPod called "Getting My Groove On" -- it has everything from Marvin Gaye, Prince, Mariah Carey, 50 Cent, Akon, Pussycat Dolls, Journey, Justin Timberlake, Bon Jovi, Seal, Barry White -- my sexy music list is all over the place. But the best song to fuck to by far is "Crazy Bitch" by Buckcherry. Oh, yeah!
10. Do you use props in bed and what kind?
Margolis: I've tried almost every type of sex toy -- most are more hype than pleasure -- but when wearing my hottest, sexiest lingerie with my "come fuck me" high heels, my favorite toy is a good vibrator and a paddle that I give to my man. I liked to be spanked!
11. You've tried Internet dating, but how do you feel about text sex on your cell phone?
Margolis: That's a lot of fun! Especially before you are going to see that person. And now that you can add sexy pictures to it too -- oh, my God -- that really adds to the excitement.
12. Have you ever had a threesome?
Margolis: No, I have never had a threesome. I am single for the first time in my life. But I will tell you that having a threesome is at the top of my list of things to do. To have a threesome with Brad Pitt and Angelina Jolie would be my ultimate fantasy.
Photo courtesy Cindy Margolis