Sex Advice from . . . Celebrity Impersonators

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Natalie Reid (Paris Hilton), 21
natalie-reid.com

After twenty minutes of giving my boyfriend head, my jaw starts to hurt and I can’t feel my face.
Obviously.

How do I transition out of oral sex without making it obvious that I don’t enjoy it?
Is it that you don’t like doing it, or that you don’t like doing it for twenty minutes? Twenty minutes is a very long time. Just tell him, “My mouth is getting sore, and I want to hop on top of you.”

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My girlfriend is a porn-prude. I want to incorporate porn into our sex life but don’t want to worsen her phobia. What is the best way to introduce it?
Soft-porn channels. Let her know that it’s only fantasy, and that it turns you on and makes you really hot. But if she really hates it, you can’t force her to watch it because it’ll just make her resent you. There are some boundaries you have to respect. But you can try to introduce soft porn and watch it together. But if she’s still not comfortable, then just drop it.

My girlfriend of three years just told me that she thinks she’s bisexual and wants to explore sex with other women. I want to be supportive, but the thought of her sleeping with someone other than me — male or female — is too much for me to bear. Should I be supportive of her sexual identity?
This is very tricky for the man, especially if he’s jealous. But you should definitely be supportive because either way, she will explore it, and possibly do it behind your back. Then she’ll be cheating on you. So if she feels strongly about it, and really does want to explore this, you have to be supportive of it.

I’m single and want to answer a personals ad for no-frills oral sex. I’ve never done this before, and I’m afraid of meeting the person and not being attracted to him. What advice can you give me?
Answering an ad can be dangerous, whether you’re a man or a woman, but more so for a woman. Meet in a public place first before you decide to go to his apartment. And let that person know that your friends know where you are, even if you didn’t tell your friends you were doing this. But don’t say it in a way that makes the person you’re meeting think that you were skeptical. Just drop it subtly or say in a playful manner that other people know where you are.

I have a history of cheating on my partners. I don’t want to make those mistakes again, but I feel compelled to tell my new partner about my past. Is it better to be honest, or would I be causing unnecessary drama?
If you told him, he would probably dump you or start cheating on you. That’s something you should definitely not let him know about. You can’t always tell your partners everything about your past.

Richard Halpern (Austin Powers), 44
richardhalpern.info

Does the line “do I make you horny?” actually work?
Yes! It actually does! Especially when I say it in Spanish: Te hago sentirte caliente, baby? Si? Te hago?

I want to break up with my boyfriend, but he’s depressed, and I’m afraid that the break-up will throw him over the edge. I still care about him, but I’m unhappy in this relationship. Should I wait until he feels better, or just cut the cord?
You can do both. You can break up with him but still be his friend to help him get through this. Tell him, “I don’t want to see you in this way, but I’m not going to abandon you.” Now, if he freaks you, then you let him go because then he’s going to pull you down too.

What’s the best way to initiate role-playing during sex?
Break out the teddy, heels and the fishnet stockings. Then hand them over to him and say, “Okay, whenever you’re ready.” Try improv. Play charades with the neighbors.

I’m a woman and my boyfriend just told me he’s dated men in his past. Should I be concerned that he’s gay?
It depends on how long you’ve been together. I would be concerned if you’ve been dating for two or three years, then all of a sudden, he’s springing this on you. Because then what else hasn’t he told you? But if you don’t know each other that well, then it’s okay, it’s part of the getting-to-know-each-other process. It’s up to you whether you want to accept it or not.

My girlfriend is a porn-prude. I want to incorporate porn into our sex life, but don’t want to worsen her phobia. What’s the best way to introduce it?
Make a video of yourself, pop it in and don’t tell her. Tell her she doesn’t want to watch American Idol and that she would much rather watch this. That’s what I’ve done.

Pat Rick (Bill Clinton), 59
counterfeitbill.com/cb.html


I’m having an affair with a married man, and he keeps emailing me and sending me text messages. I’m worried about leaving a paper trail. Am I being paranoid?
If a President can get in trouble, than the average man should be very paranoid. Our technology has set traps for us, and we’re paying the price. So leave the poor man alone.

I’m a thirtysomething woman. A few of my thirtysomething boyfriends have left me for much-younger college students. What’s this about?
It’s about thirty-plus women learning too much too soon, and us having to change our strategy. The older we all get, the wiser we get. In spite of people saying we don’t want to play games anymore, we know how to play the games even better the older we get. Generally speaking, younger women find older men more powerful. When women get older, they become more powerful and that’s intimidating for men.

I want to break up with my boyfriend, but he’s currently unemployed and depressed, and I’m afraid that the break-up will throw him over the edge. I still care about him, but I’m unhappy in this relationship. Should I wait until he feels better, or just cut the cord?
Cut the cord, and take him out of misery too. When a younger man is depressed and unemployed, if he continues to be dependent on his girlfriend, it’s not a good sign. You will be doing both parties a favor by moving on.

I found a stain on our living-room couch, and I suspect it’s a come stain and that it’s my roommate’s. I don’t want to accuse him of having sex on our couch unless I’m sure. How can I find out if he’s doing this without asking him?
If you have a friend in the local police department, have them send out CSI. Invest in the types of light that will light up when you scan things, like they do on CSI. And avoid reconstituting the juices because it could result in pregnancy.

Is it a bad idea to sleep with an intern?
No, it’s not a bad idea. Some of our best friends are interns.

Charles Kim (North Korean dictator Kim Jong Il), 34
opmcomedy.com

After twenty minutes of giving my boyfriend head, my jaw starts to hurt and I can’t feel my face. How do I transition out of oral sex without making it obvious that I don’t enjoy it?
Twenty minutes without coming? This may be a blow to your ego, but I wonder if he is enjoying it? The next time you bob down on his kebob, try “accidentally” biting or scraping your teeth down there. Keep doing this until he asks you to cease giving head. Another way to transition out of oral sex is to transition into anal sex — the forbidden fruit for most men.

I’m a thirtysomething woman. A few of my thirtysomething boyfriends have left me for much-younger college students. What’s this about?
Age is all in the mind. Dear Leader feels young because he acts young! Have fun, enjoy life and watch others have fun with you! Try hitting the gym, maybe losing a few unwanted pounds, and a new wardrobe wouldn’t hurt. If none of this appeals to you, maybe cosmetic enhancement here or there? There’s always the prospect of dating more mature and stable men, say, in their fifties. You would definitely be a spring chicken in such company.

My girlfriend is a porn-prude. I want to incorporate porn into our sex life but don’t want to worsen her phobia. What is the best way to introduce it?
Dear Leader finds that people are more willing to accept an unpleasant task when they realize they have no other choice. So secretly tape you and her making love. Prepare your video and surprise her with a “Blockbuster Night.” If she likes it, you can move on to watching real porn.

My boyfriend likes it when I sometimes wear a wig during sex because it makes him feel like he’s screwing someone else. Is this a healthy fantasy, or should I be worried that he wants to sleep with other people?
If he is an otherwise normal and active male, this is likely just a healthy fantasy, but he probably does want to sleep with other people anyway. Don’t worry — he probably asks them to wear wigs as well. If you’re still concerned, get a new hairdo, one that he actually likes.

I’m having an affair with a married man, and he keeps emailing me and sending me text messages. I am worried about leaving a paper trail. Am I being paranoid?
Yes. As long as you don’t print these messages, there should be no paper trail. Also, there is a wonderful function called “Delete.” You might find this helpful.

My friend has been whining about her ex-boyfriend for the past year. How do I get her to move on?
North Korea has been condemned by the U.S. for violating treaties and developing nuclear weapons in blatant defiance of international law. In response, Dear Leader has publicly called George Bush a “hooligan” and Condoleezza Rice an “idiot,” all the while developing and testing weapons. What does this mean for you? Just be true to yourself. Honesty is the best policy, so tell her how annoying her behavior is. If she’s smart friend, she’ll thank and respect you for your truthfulness.  n°

Interviews by Kai Ma. Sex Advice From… appears on Thursdays. Have questions for the general public? Send them to .