Kim Kardashian

Go figure. According to 27-year-old Kim Kardashian—Hollywood socialite (she hangs out with Paris), voluptuous sex tape victim, star of the E! reality show Keeping Up with the Kardashians and Playboy cover model—the five-foot-two beauty of Armenian descent says she's the normal, grounded one of her combined nine siblings. In fact, she only drinks maybe twice a year.

Despite a famous family—her mom is married to Olympic gold medalist Bruce Jenner; her late father Robert Kardashian was a defense lawyer on the O.J. Simpson trial; and her over-protective but younger step-brother is reality TV heartthrob Brody Jenner from MTV's The Hills—Kim managed to avoid the spotlight until February 2007, when a sex tape surfaced of Kim and then-boyfriend Ray J (singer Brandy's brother). She won a lawsuit with Vivid Entertainment that had the tapes pulled off shelves. "But I can't erase that it's out there," she says. "Because of the Internet, I can't take back how people see me."

So when Ryan Seacrest approached Kim to star in her own reality TV show, the soft-spoken girl-about-town jumped at the chance to set the record straight. "Ryan said, 'Your family is hysterical. People see you hanging out with all these people, at all the cool parties, dancing on tables...but you're the one controlling your mom from getting wasted at night.'" While in Chicago recently to host a party at Crobar (she drank water all night), Kim talked about everything from her much-buzzed-about backside to the craziest place she's ever had sex.

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1. Would you ever videotape yourself having sex again?

KARDASHIAN: Never, never, never again—obviously, because of what happened. I had to explain it to my little sisters, who'd be watching TV, and they'd see on E! or Extra, or something, my picture, and they'd be like, "Kimmy's on TV!" And right next to it would be "Sex Tape." And they're like, "What's that?" Just to have to sit down and explain it to them. My step-dad wouldn't talk to me for three weeks. The stress that I know it put on my mom and my step-dad—just the whole family. If my dad were here to witness all of that, I don't even know what I'd do. It's just not worth it, basically.

2. How old were you when you lost your virginity and what were the circumstances?

KARDASHIAN: I was young. I had a boyfriend for four years...my first boyfriend. I was with him when I was 14; I'd say around late 14 or early 15, I don't remember. We were sooo in love; I thought we were going to get married. I told my mom—I brought her in my bathroom and I'm like, Mom, I think I'm gonna have sex. I think I should go to the doctor and get put on birth control. And my mom was like, Okay. What else was she gonna say?

3. You get a lot of attention for your backside. What's your favorite part of your body?

KARDASHIAN: My toes; I like my feet. But I'd say my butt. I like [the attention]; I think it's funny. It bothered me when people would come up with rumors, like, "Oh, my god, she has butt implants, it can't be real." Who gets butt implants? Come on. Do you know anybody who has butt implants?

4. What do you wear to bed?

KARDASHIAN: I love lingerie. I love the little booty shorts—boy shorts. I sleep in lingerie every single night, whether I'm by myself or not. I like to wake up feeling good. You'd think a guy was coming over. Sometimes if I'm by myself I'll wear cottony ones instead of lace ones and my girlfriends or sisters will come over, and they'll be like, "Who is coming over? You're so weird. There's no guy around; what're you doing?" But it's totally for me.

5. Who do you think has the best ass in Hollywood?

KARDASHIAN: Jennifer Lopez; I love her. Jessica Biel has a cute butt, too.