Get Naked

Q:

I really need your help. I’ve been happily married for more than ten years, except for one problem. That’s right, you guessed it: Our sex life has slowly but surely deteriorated. It’s not that the sex isn’t great—it is. It’s just ridiculously infrequent. I’m sure we’re both to blame—we’re getting older, we’re tired, we’re not feeling well, it’s too hot, what about the dog?

A:

It really doesn’t matter whether your past includes plastic surgery, plantar warts, a penitentiary stay or a penis—the same rule applies: The early stages of a relationship are all about building trust, so it’s important that you put the real you front and center. Does that mean telling someone that you’re transgender before the tricolore salad arrives on the first date? Probably not, but frankly, the news should come not too long after the tiramisu. A friend of mine just went on a date with a 31-year-old woman who immediately fessed up to being the proud mother of a 13-year-old son. Yes, that kind of confession would kill the mood (and the chances of a second date) for many guys, but that’s actually a good thing: Often, in their quest to avoid rejection at all costs, people forget that the whole goal of dating is to weed out the people who are completely wrong for you, so you can zero in on the keepers. The faster you know someone’s not the one, the better, so trying to sell yourself to a guy who can’t handle who you are is horribly counterproductive. Obviously, it’s a delicate balancing act, but in your case I’d let the first date run its course, let the guy get to know you without the transgender label and before the next date rolls around, call and deliver the news. You probably don’t need me to tell you that you’re likely to feel disillusionment about the state of humanity in this process, but just keep being the self-secure, nonneurotic person you are, and ultimately you’ll meet the right guy.

Q:

I am a good-looking, healthy, virile, prosperous and creative 60-year-old single man. I am in love with a vivacious, bright, sexy, multiorgasmic 34-year-old woman with a keen sense of sexual fantasy and pleasure. We feel that we are the loves of each other’s lives. We communicate intellectually, emotionally and physically. However, there are significant complications: She is married and has a two-year-old child. Her marriage is sterile, boring and mechanical. She is not intimate with her husband, and she maintains that she made a grievous life choice by marrying him “on the rebound” years ago. However, she does not want her child to come from a “broken home.” She is also intimidated by what her parents and society think. In addition to those concerns, her husband is quite successful in business, and she enjoys a lavish lifestyle. Essentially, they are coparenting roommates. I frankly feel that she likes having two lives. I think it’s easier for her, and more pure in some way. I struggle with wanting to be with her 24/7, which is not possible. It is probable that we will eventually get caught by her husband. Her life will be hell at that point. We are very careful, but there are no guarantees. Her husband travels extensively on business. I am interested in your opinion about this.

A:

It sounds like you found yourself quite a woman. Let’s take a look at her wonderful traits: (1) She’s strong-willed: It’s not every woman who can crush her own soul just for the sake of lavishness. (2) She’s got traditional values: And by “traditional,” I mean “straight out of the 1950s”; you know, that era when people had no fucking clue how to be parents and were moronically obsessed with what the rest of the automaton-filled cul-de-fucking-sac thought of them. (3) She’s a great lay (hey, even I have to concede that one—now if only her brain cells were as multi- as her orgasms). Does she honestly believe that it’s better for her child to grow up in a home filled with simmering resentment than to have to deal with the issues that come with divorce? And do you both honestly think it’s a viable life plan to just wait to get caught by her bound-to-be-apoplectic husband? I’m happy that you found your soul mate (actually, I don’t really give a shit, but the official sexpert handbook mandates that I include one positive sentiment in every response), but if you two really have a good thing going on, why don’t you deal with things honestly, have her end her failed marriage and rescue the kid from an emotionally screwed-up future? Do that, and then I might actually be impressed by your good-looking, healthy virility.

Q:

I have a friend who is turning 18 in October. He is already in college. I want to get him a book about sex for his birthday. A book that doesn’t insult the intelligence of an extremely bright young man who—despite having grown up with the Internet and porn—has not had a lot of success with women. When I was 14, my friend gave me her sister’s copy of Everything You Always Wanted to Know About Sex but Were Afraid to Ask. That book helped me tremendously over the years and is still probably stuck between the mattress and box spring of my old bed in my parents’ house. So I turn to you to help me. Please guide me in picking an effective book. This is a very sensitive subject and I want to do it right.

A:

That’s an easy one: I’d get him the latest edition of The Good Vibrations Guide to Sex. Brought to you by the same folks who’ve helped usher in the age of the sex toy, TGVGTS is better than most sex manuals because it’s comprehensive, it’s written in a way that doesn’t make you want to autoasphyxiate, and best of all, it doesn’t ghettoize information by orientation or proclivity—it just lays out all the facts and lets you gravitate to what you’re interested in. (Who knows? Maybe it’s not women this guy is into.) To give you an idea of just how gloriously unclichd TGVGTS is, check out this passage from their chapter on anal sex: “For convenience’s sake and to avoid a morass of pronouns, let’s assume that Tarzan and Jane are about to try anal intercourse for the first time. Jane has fashioned a beautiful dildo harness out of jungle vines, and Tarzan is eager to enact his fantasy of feeling Jane moving inside him.” Any sex manual that can turn Tarzan into a big whimpering bottom deserves to be on the shelves of every American household.

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. Find more “Get Naked” online at timeoutnewyork.com.