Q I am a straight man who hasn’t been living in New York for very long. I moved here from the Midwest about five months ago to start my career and have been having a hard time finding a sex life. I am interested in group sex, but being from the Midwest, I’m fairly unaware of how the process goes in “applying” for such an act. How do you get to know people here in NYC that are into exploring their sexuality? I have never been with more than one partner; where do I start?

A You are exactly the type of citizen this city should welcome with open legs, but you can’t just expect all of your sexual dreams to materialize immediately. First things first, you have to start having sex with just one person (preferably someone who’s in tune with your adventurous side). Since you’re still relatively new to the city, you should assume the kind of anything-goes persona that people generally develop when they’re traveling out of town. That means laying yourself out there, kinks and all, to women you meet. Naturally, you don’t want to completely skeeve the ladies out, but I think asking how people feel about threesomes is perfectly palatable getting-to-know you conversation (after a series of less scandalous questions, of course). Treat the flirtation process as an experiment to see just how much you can get by coming out and asking for it (you’d be surprised how little this tactic is used, for fear of facing rejection). There are also plenty of venues to place anonymous personal ads seeking what you’re looking for (check out our annual Sex issue for tips; it’s at timeoutnewyork.com/sex07), but I would recommend doing it in person—spot what you want and then go for it.

Q I am 20 years old, attractive and accomplished, and I recently split from my boyfriend of two years for absolutely no reason other than that he is afraid of getting too tied down so early in his life (we had a flawless relationship otherwise). So like a rational girl, I’ve reentered the dating world, but found all of the guys falling woefully short of my ex. Also, I’ve been spoiled with great sex on a regular basis for the past two years, and being single is an unpleasant shock. My feelings (not to mention my body) are all telling me that I’m meant to be with my ex, perhaps forever. But how exactly do you get a 22-year-old man in the most adventurous and flighty stage of his life to realize this?

A I think Mr. Threesome up there has gotten inside my head, that’s why this advice is going to be a bit unconventional, but let’s throw it out there anyway: What if, instead of completely breaking things off, you and the ex opened up the relationship a little? You guys would have to come up with the precise terms of this arrangement (when you can sleep with other people, how often to get STD checks to make sure everyone’s having safe sex, what the level of disclosure would be), but if it’s the concept of being completely tied down that’s freaking him out, why not give the guy a little slack? Since you can’t fight his biological urge to have sex with as many women as possible, just roll with it while providing him with something the other girls can’t: a nurturing relationship that seeks to accommodate the needs of both people involved (I can already hear the feminists screaming at me for letting the guy get the better end of this deal). Obviously, this arrangement would not be for everyone, and perhaps he was just using the “I don’t want to settle down so fast” excuse, when in fact there were other reasons he no longer wanted to be in a relationship with you. Still, if you’re happier having him in your life than out of it, there are ways to make that happen so that everyone gets what they want.

Q Hi. I wanna be a gay porn star.

A Boy, did you come of age at the right time. Thanks to a powerful combination of technology and money, everyone can be a porn star these days. Instead of just jumping into the industry, I would give yourself a little test-drive by filming yourself jacking off (or whatever) and posting it on XTube. That way, you can keep your identity hidden and see if the thrill of having people watch you perform sex acts is as rewarding as you think it is. This is not a career choice you want to take lightly, since it has the power to forever affect your future work and personal life. Another note of caution: Whenever you make something you love doing into your job, it inevitably ruins the experience at least a little. Being forced to get hard upon command and do it with all sorts of people you’re not even attracted to doesn’t exactly sound like a dream job. If it’s the thrill of exhibitionism that really gets you going, there are plenty of ways to fulfill that kink (just ask the guys who clearly get off on having some prolonged naked time in my gym’s locker room) without making a whole career out of it.

Q I think I’m addicted to my vibrator. I’ve been having sex for over four years. Fourteen partners, but only two were able to get me off—and it wasn’t even through sex, it was through cunnilingus! My first was able to only because I didn’t use my vibrator, and the second was a man who knew what he was doing, but it took him the better part of 45 minutes. I’ve been told that using a vibrator can decrease the sensitivity of a woman’s clit, but do I really have to ditch the “every girl’s best friend” to be able to get off the old-fashioned way again? I’m so frustrated!

A It’s not your vibrator you should be mad at, it’s God. That’s right, he (and clearly it must be a he) is the one who made do-it-yourself female orgasms far easier to achieve than the partner-induced kind. In fact, rather than causing desensitization, masturbation and vibrator use actually improve orgasms in women, because they help pinpoint what feels good (which, in theory, can then be communicated to ham-handed, ham-penised and ham-tongued sex partners). Sometimes women overdo the vibrator use in a masturbation session, and clitoral soreness will ensue, but that’s just a fleeting problem. I’m sorry you’re frustrated, but if you’d been reading “Get Naked” more often, you’d know that you are far from alone. If I were you, I’d stop worrying about the specific ways you achieve orgasm and do whatever works best. If that means incorporating a vibrator into your sex life with other humans, then so be it.

Send letters to Jamie Bufalino c/o Time Out New York, 475 Tenth Avenue, 12th floor, New York, NY 10018, or send e-mail to sex@timeoutny.com. Check out “Sex on the Street” with Jamie Bufalino at timeoutnewyork.com/video.

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