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Get Naked: Sex advice for New Yorkers (August 16, 2012)

Jamie Bufalino helps a reader develop some orificial intelligence.

Q I’m a straight male, and a few nights ago I went home with a girl I met on a job. We were making out and groping on her couch, and things were great, but when we got in the bedroom and I started going under her pants, I noticed her genitalia seemed weird. Her clit seemed less sensitive, and when I inserted my fingers, I thought, This feels like an anus, not a vagina. When I couldn’t find another hole that would be the anus, I thought maybe something there was artificial. I also felt grooves that could have been surgery scars. She did have some male-ish features in her facial structure. Unfortunately, thinking all this made me lose my erection, but I continued to finger her until she came. Now, I was slightly stoned and I was afraid to ask her anything because I thought maybe I’m being paranoid, and I didn’t want to totally offend her. She also didn’t seem confused by my confusion. She didn’t ask why I lost my erection; she seemed to enjoy everything. I’m not an anatomy expert, but I’m certainly experienced enough to recognize the different parts of the vagina, and this was different. I never got down there with a flashlight to really confirm anything, but I’m still not sure what happened. I didn’t think M-to-F surgery involved the anus. Is it possible she’s had some sort of surgery there, or was I just way too stoned? BTW, I would not be ashamed or upset if I found out she was hermaphrodite or transgender, I just want to know if I should stop smoking weed before sex.

A I usually don’t think it’s wise to give a thumbs-up to any kind of drug use, but in your case I’m going to make an exception, mostly because I look forward to you getting majorly baked, having all sorts of freaky encounters and then writing more amazing letters like this one. I might also suggest, however, that you study up a little bit more on human anatomy before your next stoned sex date. There is, after all, something called the perineum (you might know it better as the “taint” or the “grundle”), which is the stretch of highly erogenous territory between the genitalia and the anus—which would still be there even if the genitalia in question used to be a dick and then got surgically inverted into a vagina. I’m just going to assume you didn’t notice a set of testicles down there, because they would have either (a) been removed, (b) not existed or (c) seemed like a couple of Hacky Sacks to your pot-clouded eyes/hands. Oh, and just for the record, male-to-female reassignment surgery would have no reason to involve the extremely gender-neutral anus. More than anything, your story has me wondering what you think you were fingering when you were aiming to work over her clitoris, but then decided you were actually in her anus. A hemorrhoid? A skin tag? A joy buzzer? The grooves/scars you felt do suggest that some surgery took place, but there are plenty of other reasons (like childbirth or an injury) for actual women-since-birth to have an incision on that part of the body. I suppose we’ll never know what happened on that fateful, THC-addled night, but there is one thing I do know—you’re one of the coolest, most laid-back lover-boys I’ve heard from in a really long time. Any straight guy who can write the sentence “I would not be ashamed or upset if I found out she was hermaphrodite or transgender” is aces in my book. Although just so we’re clear, if she were a hermaphrodite, there would be one other big, dangly anatomical sign that you probably would have noticed.

Q I’ve been with this girl for a little over six months now. We have an okay relationship, but it’s clear we’re not “the one” for each other. I could go into specifics, but we can narrow it down to one giant thing: She knows that she will eventually move back home to the Midwest to raise a family, and I have no intention of ever leaving the Northeast. Because I’m at the age where I’d like to find “the one,” I’d rather not stay in a relationship that doesn’t have a future. The tricky part is that despite being in the city for about six years, I haven’t developed any real friendships. I’m not sure you know just how hard it is for a straight 28-year-old guy to make close friends from scratch. I work almost exclusively with older married men with families. I joined a social sports league, but there’s only so much chitchat that can happen during a sports game or in a crowded bar full of people playing flip cup. There’s certainly no straight-man-date arranging going on. Anyway, this girl I’m dating has some amazing friends, and I get along with them great, but I haven’t hung out with them without my girlfriend. Every time I’ve had a breakup where we decide to stay good friends, it never happens. How can I develop friendships with my soon-to-be ex’s friends, or is it just too weird to attempt?

A I certainly don’t think it’s too weird to attempt, but it depends on how well the breakup goes. The key question is whether she realizes that the geographic issue is as big as you say it is. Getting dumped is never fun, but six months isn’t really a heart-crushing amount of time investment, so chances are she won’t be super pissed at you. (Either way, the friend thing should give you even more incentive to end things as calmly and thoughtfully as you’ve laid out the reasons here). I’m actually more concerned about your inability to make friends on your own. Going six years without platonic friends is kind of strange, particularly in super-social New York. I get the whole older, settled coworkers obstacle, but you definitely need to be more proactive in other venues. If none of your sports buddies have made a bromance move on you, you should take the initiative. Get a phone number, write a text, set up a movie outing or a beer-grabbing and let the bonding begin. Back to your girlfriend’s friends: If she does end up moving back to the Midwest, it would seem silly and spiteful of her to cut you off from her NYC circle. I would play the “poor friendless me” card, but only after an appropriate amount of time has passed since you had the breakup talk, and she’s on her way to having a happy life post-you.

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.

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