Sex Advice from . . . Urban Planners

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Michelle, 24

I’m moving out of my scummy bachelor pad and I want my new apartment and neighborhood to be chick-friendly. What should I look for?
Use ArcGIS (Geographic Information System software) to map out the spatial distribution of female residents in your age group in that area. Choosing an area with a high concentration of women will not only meet your immediate needs, it will also provide easy access to future girlfriends in the event that you find one and she dumps you.

My boyfriend can’t seem to find my g-spot. What are the best positions to make sure he’s hitting it squarely?


If you aren’t able to figure out the spatial configuration of your partnership, try drawing conceptual plans
of the two of you in various positions. That should be effective and make you laugh.

I had a threesome with my boyfriend and my best friend. Afterward, all three of us agreed it was like having the best of all worlds. Could this be the beginning of a successful three-way relationship?
It could be. Or it could be the beginning of your boyfriend and your best friend’s new relationship together. Since you’ve essentially given them approval to hook up, don’t be surprised if you start finding her undies on your bedroom floor when you come home late.

When is break up sex appropriate, and when is it a bad idea?
It’s definitely a bad idea if you know your ex is still dangerously into you. Nothing ruins the afterglow of break up sex like being stalked.

Mike, 38

My girlfriend and I want to have a foursome with this couple we’re friends with. How do we approach them?
If you want to keep these people as friends, you should avoid seeing them naked. But if you’re more interested in dirty sex than friendship, my advice would be to make up a story about you and your girlfriend having had a three-way. Or better yet, go out and find a third so you can tell your friends the truth. Then mention the three-way to them at some point, as casually as possible, and start a discussion about the topic to see where that leads. If they’re grossed out, drop the subject. If not, keep going. Or all four of you could just take Ecstasy and let chemically enhanced nature take its

When is break up sex inappropriate?
When you know it’s break up sex but haven’t bothered to inform your partner.

I’m moving out of my scummy bachelor pad and I want my new neighborhood to be chick-friendly. What should I look for?
A neighborhood nowhere near a college or a Hooters. Go onto the internet and search for day spas in your town. Then find a place within a five-minute walk of there.

Should every sexually dominant person go submissive occasionally?
Do great chefs taste the food they’re serving? Every dom should sub now and then — otherwise you have no idea whether what you’re giving out is good, bad, or indifferent.

What methods can I use to delay my orgasm besides just going slow and taking breaks?
If you’re young and virile, you should be able to have more than one orgasm in a relatively short amount of time. Instead of falling asleep or turning on the TV, keep fooling around till you’re ready to go again. The second time will take you longer to climax. If that doesn’t work, buy your girlfriend a dildo. It never gets tired and never needs Viagra. And you can learn to operate it just as well as, if not better than, your willy.

Betsy, 42

I like putting guys on a leash and making them lick my shoes and bark like dogs. Would it be healthy for me to play the submissive occasionally?
This reminds me of that movie about a slumlord. Was it Danny DeVito? [Ed. — Joe Pesci] The housing judge sentenced him to live in one of his cruddy buildings and deal with real people for a change. He learns empathy and grows emotionally. That’s what should happen to you in your situation. You might also spend some time with dogs and get into their mindset. Have you seen the TV show Dog Whisperer with Emily the pit bull? She had to learn to lie on her belly and get sniffed by a bunch of big dogs instead of chewing their throats in two.

I like to be really loud during sex, but our neighbors are freaked out by all the noise. What can we do?
If you’re not in a position to install double-pane windows and insulation in the floor and ceiling, test out ball gags. One person’s attractive nuisance is another person’s complaint to the police.

I’m moving out of my scummy bachelor pad and I want my new apartment to be chick-friendly. What should I look for?
You want it clean, clean, clean — especially the bathroom, kitchen and the sheets on your bed. Look for something new with a washer/dryer in the unit or close by. Also, good ambient lighting, not a sixty-watt bulb swinging twelve feet overhead.

My landlord is hot. Should I make a move?
This is kind of like hooking up with your boss. How secure is your lease? How likely are you to need him or her to actually do repairs? On your side may be local tenant-landlord laws and rent-control laws, which, if they exist in your community, generally don’t let him evict you for failure to have sex. If you like complications around your home front, go for it, but be prepared to move if it doesn’t work out.

Valerie, 26

How can becoming an urban planner help me get laid?
Urban planning opens the door to the exciting male-dominated world of architects, builders and engineers. Merge those parcels. And for men, saying you’re an urban planner is at least cooler than being an accountant.

My girlfriend and I want to have a foursome with this couple we’re friends with. How do we approach them?
Invite them over for an innocent evening of hot-tubbing and alcohol consumption. Then break out the Twister.

How can I get an urban planner to go home with me?
Talk shit about Wal-Mart, brag about your frequent public-transport ridership and drop phrases like “spatial morphology.”

How can I delay my orgasm, besides going slow and taking breaks?
Recite the twenty-one principles of New Urbanism in your head over and over again. 

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

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©2006 Kate Sullivan &, Inc.