Get Naked: Sex advice for New Yorkers (August 9, 2012)

Jamie Bufalino wants you to have a serious talk with your spouse.

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Q It is with trepidation that I write to you with a nagging problem. I am a 59-year-old man and I have been happily married for 14 years. (This is my third marriage, but each one ended amicably and I have never cheated.) My wife is some years younger—we have a healthy sex life and communicate very well both in bed and out. We often have impromptu sex in whatever room of the house we are in. My problem: For about four years, I’ve had the urge to suck another man’s dick (no one’s in particular). I find myself looking at “pretty” men, as I am not attracted to macho types. I also feel attracted to good-looking transvestites. I travel for work and was recently in the Philippines; the opportunity arose to satisfy my urges, but my morals wouldn’t allow me to exploit someone in that way. I just went back to my hotel alone and masturbated while fantasizing about the beautiful ladyboy that I had been chatting with and buying drinks for. I came like never before, but it wasn’t enough. Do you have any advice for me? Are there places I could go discreetly and safely in New York where the men would understand my situation, yet still be willing to indulge me?

A This situation is befuddling for a number of reasons. Although it’s not that unusual for a predominantly straight guy to have thoughts and curiosity or even fantasies about a same-sex encounter, it is kind of rare for someone on the cusp of 60 to suddenly feel those urges and to be able to pinpoint the year they started popping up. That makes me wonder what happened four years ago that might have unearthed these feelings. I know you said you don’t fantasize about any guy in particular, but surely someone must have kick-started this late-blooming preoccupation. The really problematic part, however, is figuring out a respectable way for you to satisfy this urge without winding up losing wife No. 3. First of all, since you’ve made it nearly six decades without being a cheater (Kristen Stewart didn’t even make it to her mid-twenties), you’re not going to ruin that admirable streak now. That’s why, as hard as it might be, you’re going to have to sit your wife down in one of those rooms you often use for impromptu sex and tell her about what’s been going on in your head. It sounds like you both are extremely sexual people, so she should at least be able to empathize with the concept of having a serious libidinous craving. Obviously, the stickiest part for her is going to be the “ladyboy” angle. It may throw her for such a loop that she’ll start questioning if you’ve been gay all along, wondering if your marriage is a sham, etc. You’re going to have to be well-prepared for this discussion. Assure her that no one would be able to fake the authentic passion you have for her. And also, dig deep and find a more clear-cut explanation for why these desires emerged so recently. Then, once you’ve been through that grueling process and (hopefully) convinced her to let you indulge your fantasy, you’re going to find someone to help you make it real—only it’s not going to be a sex worker. Head on over to trannydates.com, the “real people, real sex” dating service, and browse for the pre-op woman of your dreams. And if your wife puts the kibosh on the whole idea, you can always use the site (complete with lots of fetching pictures) as your go-to wank address.

Q I’m a 34-year-old gay male who’s been in a relationship with my 37-year-old spouse for more than a year now. We met at a sex party and, against all odds, we fell in love, moved in together and got married five months ago. This is my second relationship. The first one ended traumatically, due to cheating by my ex. I am a very dedicated partner and so is my spouse. Here’s my worry: We were on the subway and this cute Italian tourist asked for directions. My partner, who is way more sociable than me, started a conversation with him, which I noticed was going a little beyond the quick transmission of info about trains. I felt that there was mutual interest between them, to the point that my partner shared his phone number. After we left, we had an argument. He told me the guy was friendly, and since my spouse’s holidays (not mine, unfortunately) are coming and he is going to have free time, maybe they could spend time together, go to the movies, etc. I couldn’t believe what I was hearing. He told me that there’s nothing wrong with making friends. We love each other a lot, but these episodes worry me. Am I being overly insecure?

A It’s always the Italian tourists, isn’t it? Swarthy little fuckable relationship-ruiners! Okay, so let me take a moment to quickly recap your life: Sex party, love, cohabitation, marriage, subway, Italian tourist, fight, anger, worry. Now let me delineate a future game plan for you: Mellow out and come to terms with the fact that you got hitched to an extremely gregarious people person! Just because you don’t like to chat up complete strangers doesn’t mean that anyone who does is trying to get into their Italian pants. I’m sorry you got cheated on, but this is a different dude, so you need to give him the benefit of the doubt and also not poison the relationship with your insecurities.

Q One topic you haven’t spoken about much is female ejaculation. This happens to only 20 percent of women, and it is certainly a topic that has to be approached delicately. As someone who has this amazing ability, you have to plan ahead—telling new lovers that it might happen, being willing to have new lovers run away because of lack of knowledge or fear, and making sure there is a towel around at all times. Most men do not know what to do with such an unusual situation. I started dating an older gentleman who not only knows what to do but doesn’t stop, and makes me come like Mount Vesuvius.

A I have covered the topic of female ejaculation before, and since you didn’t actually provide a question for me, I’m not sure what else you’d like me to say about it. How about I supply a little factoid for any gal out there hoping to gush like a Super Soaker: Studies show that in order to become a “squirter” most women need to have an extended session (at least several minutes’ worth) of vaginal, clitoral and G-spot stimulation, so that ejaculatory fluids get the chance to build up and then blow.

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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