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Toby Billowitz, 31

How do I avoid awkwardness and clichés when I want to invite someone up to my apartment after a date?
Just use something blatant. A friend of mine in college would always say, "You want to come see my fish tank?" Whenever anybody said that in their fraternity and sorority circle, it was automatically understood.

Female ejaculation: have you experienced it? If so, how do you make it happen?
Some girls do and some girls don't. I think that's sort of a strange goal. You should probably ask her if she does, and then what her thoughts on it are.
Take the position that she has the most orgasms from and try to make it more intense.

My partner wants me to wear a cock ring. She says it intensifies her pleasure. I want to make her happy, but imagining myself wearing a sex toy feels very unnatural and even makes me feel a little bit inadequate. Is there a way to phase out that feeling?
You feel the way you feel. Trying to convince yourself that you don't have a right to feel that way is not going to make you feel better. You just have to accept that's the way you feel: "Okay, I feel like this, but I like her, so I'm going to do this for her." And be sure to let her know that."You know, I'm doing this just for you. I'm willing to try this a couple of times."

Asides from condoms and lube what's the number one thing everyone should have in their sex drawer and why?
Hand towels, so you don't have to get up immediately afterward. That can be time well spent.


Laura, 22

How do I avoid awkwardness and cliches when I want to invite someone up to my apartment after a date?
I'm a big fan of just putting your intentions out there. "Listen I'd really like get to know the inside of your mouth. Would you like to come up to my room?"

Have you used that line before?
Something like that. I would have somehow steered the conversation to tonsils. I'm usually just blunt. When we're leaving a bar or a restaurant, I say, "Listen. Let's go hook up." Generally that gets the response I want.

I made out with a friend who's in the process of breaking up with his girlfriend. Forgivable or heinous?

It is heinous. Being the other woman or the other man is just as bad as being the cheater. If you still want to hook up with him, you can wait long enough for him to break up with his girlfriend.

Female ejaculation: have you experienced it? If so, how do you make it happen?
No and no. I don't understand what's so great about female ejaculation. I think one of the best things about heterosexuality is learning to explore a body totally unlike your own. I think guys like female ejaculation because it's so exotic, but it also makes the girl like them. Female orgasms aren't necessarily like that. Men and women are different, and that is awesome.

Do's and don'ts for dirty talking?
Don't ask too many questions. If the person is really into a sexual act, they don't want to play twenty questions. Do describe your fantasies in detail, letting the person what you like and how they can help you achieve that. Don't breathe too heavily in the other person's ear. Don't say "uh, uh" a lot.

My girlfriend just got out a long relationship. She wants to have casual sex but is having a hard time finding partners. I think she's not sending out the right signals at bars and parties. Any suggestions?
Friends of friends are best for casual sex. That way you can get a recommendation on who's cute, single and horny. Strangers at bars can be bad. You don't know if you're going to get someone with a really tainted sexual history or someone with strange preferences. And if they take things too far, you don't have anyone to complain to. With a friend of a friend, you can't get too out of line because there's a risk you're going to offend the middle party.

My friend (a girl) just started dating a girl for the first time. She is intimidated by the prospect of going down on a girl. Do you have any tips for her?
Lighter is always better, and stamina is hard to achieve but absolutely critical. I've never been that excited about receiving it myself, so I can't really say. Approach it as a scientific experiment. You have to do a little investigation.

What's the best way to get a frisbee player to come home with you?
Ask him if he wants to go deep with you or lay out.


Andrew Winton, 25

Sex in public: what are the best locales?
Newark airport. There's an air train that goes from the station to the actual terminals. Each of the cars is only big enough for two people. Almost always you'll be alone in the thing, and it takes a good four or five minutes to get from the station to the terminals. My girlfriend and I went with the expressed purpose of doing it, and the door closed between me and her, so I got off and I tried to go back, and she got on the next one going the other way. At that point, we were like, "Okay, this was not meant to be." But that was the plan.

Aside from condoms and lube, what should everyone have in their sex drawer?
I don't think you should have a sex drawer. I wouldn't be turned off, but I imagine there'd be plenty of girls that'd be turned off by a sex drawer. That seems very high-school and freshman-in-college to have a drawer full of sex items.

So where do you put your condoms and lube?
In a drawer with other things. Put it next to your drugs so it's an all-bad-things drawer. Well, they're not bad things, but they're things you don't want your grandmother to see when you're showing her around.

My friend (a girl) just started dating a girl for the first time. She is intimidated by the prospect of going down on a girl. Do you have any tips for her?
It's a good idea to use your hand as well as your mouth. Then you can massage certain parts and seem more attentive. As far as tips, probably all the girls I've talked to say that slower is better. Don't attack the clitoris with your tongue too soon.

My boyfriend and I have been together for three months and I have yet to orgasm during vaginal sex. I know I'd come with a little clitoral stimulation during sex, but am too embarrassed to ask for it or to do it myself. Please advise.
Tell him what you like. Even if he is embarrassed for a minute or two, there is no reason for him not to make you happy. Also, I've been told that if you have sex with someone from behind pretty forcefully then the balls mash into the clit a lot.

I made out with a friend who's in the process of breaking up with his girlfriend. Forgivable or heinous?
It's forgivable, but not because you didn't do anything wrong. Tact dictates that you should wait until they're broken up before you do anything else. I've known people who've had very successful relationships that started out being a rebound thing, so I see no reason why not. It's not the healthiest situation in the world, but relationships don't necessarily have to start off healthy.



Elizabeth Baron, 29

My girlfriend just got out a long relationship. Now she wants to have casual sex, but is having a hard time finding willing partners. I think it's because she's not sending out the right "signals" at bars, parties, etc... Any suggestions for how she can get the casual sex she's been looking for?
Go to bars on the Upper East Side. She shouldn't have a problem. How to approach guys? Just go up to them and say hey.

Sex in public: what are the best locales?
Prospect Park seems to be high on everyone's list. I see a lot of condoms there. Not that I've done that, though. I would do a park bench in winter. It's cold, but if you wear big jackets no one's going to know. Discreet, but public.

I made out with a friend who's in the process of breaking up with his girlfriend. Forgivable or heinous?
Forgivable. He's not married. He's started the process of breaking up with somebody. It's a grey area. But it's not worth sticking around. If he's going to do that to his girlfriend, he's going to do that to you.

Aside from condoms and lube, what is the number one thing everyone should have in their sex drawer and why?
A girl should have a vibrator, definitely. There are two good vibrators. One is the $90 Hitachi Magic Wand. There's another one, a five-speed.

Do's and don'ts for dirty talking?
If it's a guy, it's got to be graphic. There must be details involved, like, "I want to slam you against a wall and fuck you senseless." That's good dirty talk. What you shouldn't do: if I'm with a guy and it's not serious, a lot of guys think that telling me they love me will turn me on or make me want to sleep with them more. That just doesn't work with me. Don't introduce feelings. Just keep it real.

Interviews by Catherine Adcock.

Sex Advice From... appears on Thursdays. Do you have sex-advice questions for the general public? Send them to .



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