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Photo courtesy Cindy Margolis

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COULDA, WOULDA, SHOULDA:
"I would have been the biggest slut."
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By Sarah Preston

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.com 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?

Cindy 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.

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