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Get Naked: Sex advice for New Yorkers (November 1, 2012)

Jamie Bufalino on how to rebound from a fellatio faux pas.

Photograph: Courtesy Shutterstock
Q I’m writing to you because I recently experienced one of the most embarrassing moments of my life. I can’t seem to shake it, so I’m hoping you’ll at least make me feel like it’s really not that big a deal. I went out on a few dates with a guy I like very much. I’m a woman who believes in taking things slowly, so on the first two dates we didn’t do anything with our clothes off—just a little kissing and some groping. I could sense this guy was a little frustrated by the slow pace, so on the third date I decided we would explore each other’s naked bodies and enjoy some foreplay, although I made it clear I still wanted to wait on having sex. I didn’t count on how hard he would try to get me to go all the way. He was really insistent, saying how horny I was making him and how good it would feel. I didn’t give in, but I also didn’t want him to feel like I’m a frustrating bitch, so I tried to give him the best blow job he’s ever had. The problem was that I overdid it and tried to take his dick as deep as I could, and ended up gagging myself and throwing up all over his crotch. Obviously the night was ruined, and although he and I have communicated since this incident, we haven’t seen each other in two weeks. How do I get things back to normal with him, or do I have to face the fact that I fucked this one up and move on?

A I’m not going to lie—it’s hard for a dude to recover from such a fellatio trauma. It’s a truly shocking transition (and yes, I am speaking as someone who’s had the misfortune of being on the receiving end of such a scenario) to go from basking in the delights of having your rock-hard dick tantalized to suddenly seeing your quickly wilting member covered in gastric acid and trying to identify exactly what kind of food chunks are taking up residence in your pubic hairs. But here’s the thing: Sex faux pas happen all the time. Whether it’s a guy’s fumbling inability to insert his penis into an eagerly awaiting vagina (which is currently looking at its cute little vagina watch and seeing that a good ten minutes have passed), or that loud farting sound that happens when two sweaty stomachs unsuction from each other, or some honest-to-goodness actual farting, or the pièce de résistance—puke on the pecker. Ultimately, it’s not the fact that something awkward and disgusting happened, it’s how the couple reacts to it that reveals the nature of the relationship. The unfortunate thing is that this happened at such an early stage of the dating process. If you had gotten to know each other better, you might have just been able to laugh the whole thing off, soak the sheets in the tub and call it a night. I still think you’ve got a shot at repairing things—you just have to tell him exactly what you told me: that you were trying so hard to please him and got carried away, and the universe gave you an immediate, messy lesson on how important it is to stick to your principles and maintain your self-esteem in relationships. If he’s the kind of guy you’d want to have a long-term thing with, he’s not going to let a little crotch vomit ruin a potentially solid relationship. If he does, you should be glad you got the chance to douse his dick in stomach contents before sending him on his way.

Q Three years ago, my husband killed himself, leaving me a widow at the age of 46. Since then, you would not believe the men I have met. First of all, there are plenty of married men who want to have a “relationship.” I don’t want that. Then there are the 28-year-olds who want a “cougar.” Not interested. And then there are the men who think nothing of telling you upon meeting that their very specific sexual preferences are threesomes, anal and shemales. I think I’ve met them all. I really am an intelligent woman with a good job, money in the bank, a fun personality and a sexy, curvy body. Should I just give up on finding a normal man who wants a relationship with a normal woman? Am I too old? Are there any men out there who are interested in a woman who loves sex, is smart and just wants to have a nice, fun relationship?

A Did you forget whom you were writing to? Of course I would believe your stories about the men you’re meeting out there. I’m truly sorry to hear about your husband’s death, and I understand that the last thing you need now is to deal with a bunch of bozos who don’t have the same serious perspective on life that you do. But you can’t give up, and you’re definitely not too old. Put yourself in situations that lend themselves to attracting serious men (or at least men who have an interest in something other than sexual fetishes). I’m talking about volunteer organizations, various culture and film clubs, or museum-aficionado groups. It’s not a foolproof method, but it will give you a better chance at meeting a like-minded mate than at a random site or a bar.

Q I’m a 27-year-old straight guy who’s had two near misses with condoms breaking. What am I doing wrong? Luckily, they didn’t break after I had ejaculated, but now I’m wondering if that did happen, what’s the proper way to deal with that situation?

A The first thing I’m wondering is: How old are these condoms? If they’ve been trapped in your wallet for a while (do people still carry them that way?), they might be getting too beaten up for use by the time they actually see the light of day. Second, you need to make sure you’re using enough lube with the condom. Too much friction equals higher propensity for condom breakage. And by the way, you should probably get an STD test after a condom mishap—just to be on the safe side. And if there is any presence of semen at the time of the malfunction, the woman you were having sex with should really get Plan B (“the morning-after pill”) to guard against pregnancy.

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.