Dear How to Do It,
I’m a guy, 24, predominantly straight but heteroflexible, I’d say—I’ve hooked up with guys but haven’t felt attracted to men lately. I’m married to a bisexual woman who’s 26 and who has been in (fairly) serious relationships with both men and women. My wife expresses desires to have a girlfriend, which I’m fine with for the most part. She says she’d be fine with me having a boyfriend but not a girlfriend, which is an issue for me because one, I’m not particularly into men anymore, and two, I think that’s a massive double standard. In my mind, having sex with someone else is having sex with someone else, regardless of gender identity.
For the record, I’m not a prude—I’m not completely uncomfortable with the idea of an open relationship (uneasy, but I think it could work if approached right)—and I DO like dick. I just don’t find masculine-presenting people very attractive at the moment, and I don’t see myself wanting to hook up with a guy any time soon. When I’ve expressed that, and that I’d probably rather hook up with someone who presents more feminine before I hooked up with a cis guy again (I have a trans woman or fem-presenting person in mind), my wife seems pretty thoroughly repulsed by it, and seems to reduce the idea that I like dick to me being into guys. Again, I had sex with maybe three or four guys in high school, and I’m not strictly excluding it, but I don’t particularly want to screw a guy at the moment.
Am I in the wrong for believing that a side piece is a side piece, regardless of their sexual organs? Am I a jerk for not wanting to concede and let her hook up with women if I can’t as well—even though I probably would concede?
—Open and Shut
Dear Open and Shut,
sex is subjective. If you believe that a side piece is a side piece regardless of genitals or gender identity, and your wife is using a binary framework, you’re looking at a mismatch in how you see the world. It’s OK. These things happen. You’ll have to decide whether “fair” and the freedom to fornicate with women and femmes are more important to you than your wife’s wishes. You’ll have to decide what you’re willing to bend on, and what you refuse to compromise. Is your wife perhaps afraid that another woman could be a replacement, and operating under the delusion that a man never could? Untangling that might help her be more relaxed about who you might hook up with. Talk it through carefully—it’s important that you enter into an open marriage on solid ground, without grievances about the rules.
That said, I’m seeing a red flag in what you describe as your wife’s “repulsion” at the idea of you hooking up with trans women or femme-presenting people. Now, there’s the possibility that she’s twitchy because woman, but there’s also the possibility that she’s got some TERF or other transphobic rhetoric bouncing around in her brain. Dig into that. Ask her what bothers her about the idea of you hooking up with a trans woman, or a femme-presenting person. Talk about gender. See if you can open her mind to the plurality of gender presentations.
Whatever happens, watch your words too. Have you ever hooked up with a trans woman? In case you haven’t, “dick” frequently doesn’t feel like the most appropriate word for pre- or non-op genitalia. If you do pursue trans or nonbinary partners, follow their lead on that.
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Dear How to Do It,
My little brother is 11 years younger than me, currently 18 years old. He’s becoming an amazing young man, someone that I’m proud to say I had a hand in raising. He’s decided not to go to college, and is instead currently working as a waiter with the goal of maybe going to a trade school in the next year or so. Well, over the holidays, we had a heart-to-heart about his future, and he told me in confidence that he was still a virgin, and that since all of his friends weren’t, he was a little embarrassed about it. He’s only had one girlfriend for about six months in his sophomore year, and she ended up moving away, leaving him heartbroken and a little gun-shy. During our heart-to-heart, I told him not to worry about it, that 18 wasn’t that old, and that there wasn’t anything wrong with him just because he hasn’t had sex yet. He’s a former athlete, so all of his friends are pretty macho and probably not entirely honest about their exploits, either. I’m sure that’s where a lot of his embarrassment comes from.
I guess my question is, since he isn’t going to college, how can I encourage him to meet girls? He doesn’t want his first time to be with a Tinder hookup, and he’s very honest about how he doesn’t really want anything casual and how much he enjoyed being a boyfriend. He doesn’t have many female coworkers, and most of his current friends are from his former football team. He’s very shy when it comes to girls, so I don’t see him as the type to flirt with someone on the street. Since I married my high school sweetheart and have no idea how to even go about dating in our society today, especially for someone who can’t go to clubs or bars, I’m lost. Any suggestions?
Dear Virgin Spring,
Work is not a great place to meet people for relationships—or casual sex, for that matter. And a club or bar is not a great place to meet people for relationships either, although it is a good place to meet hookups. So it’s probably for the best that alcohol-fueled spaces aren’t on the table right now.
What your brother should do is think about his hobbies. He should think about what he’s into, and where he can meet young women who are also into those things. Common ground helps establish rapport, which makes a phone number or even a date more likely. While he’s at it, he might make new, non-football friends of the same gender, and they might have female friends of their own who are cute and looking for someone.
Meanwhile, not all dating apps are for hookups. He could try a place like Hinge that is pretty romance-focused, or a place like OKCupid that matches people based on some personality overlap percentage and attracts people looking for both hookups and committed relationships. It might be a bit overwhelming at first, but he can ease into it.
Mostly, your younger brother should take as much time as he wants. Being 18 and not having had his first sexual experience—and what exactly are we calling a “sexual experience”?—doesn’t make him that much of an outlier. American boys tend to lose their virginity around 17, at least as defined by heterosexual penetrative sex, and plenty of people wait until their mid-or-late 20s. Support your brother in setting his goals, which at this stage seem to be committed romance, and be there for him with an open ear and a dry shoulder as he’s working through the frustrations and disappointments of dating.
Dear How to Do It,
I’m a woman in my mid-20s who has only ever dated and slept with men before. A couple months ago, I started casually seeing a woman, “Kate,” whom I work with, and she’s incredible. She’s smart, beautiful, and we get along really well. Though we haven’t put any labels on anything, she spends the night at my place frequently, and when we’re not at work, we text or talk on the phone most days. I don’t think any labels are all that important, but I guess this would make me bi.
My issue is that I’m either scared to, or have no interest in, going near her vagina. Honestly, I’m not sure which it is. We hold hands, cuddle, make out, and she’s fingered me before and gone down on me once. It’s hot and I get super turned on, and I fantasize about doing the same to her, but when we’re actually in the moment, I can’t do it. I’m not too worried about not pleasing her; I’m confident she would tell me what she likes, and I have the same parts so I know what generally feels good. She’s a lesbian, so she knows what she’s doing and has a lot more experience.
We’ve talked about it and she’s extremely understanding, knows I don’t have experience with women, says I never have to do anything I’m not comfortable with, we can take it slow, and that she gets turned on plenty by turning me on.
But this isn’t fair to her, right? I need to return the favor before it becomes much more “unequal”? I’m 100 percent attracted to her, but maybe I’m having some sort of early midlife crisis and I’m not actually bi? Right now, I think my options are to either suck it up, get a little drunk, and just go for it, or to break it off before we become anymore involved. I am so into this woman, but I don’t think a relationship is possible if I can’t be intimate with her in that way eventually. Is there any hope for us?
—South of the Border
Dear South of the Border,
Let’s get the identity part out of the way first. Even though you say you don’t think labels are all that important, they’re still in your head—when you question whether you’re really bi—and you’re tripping over them. Give “bicurious” a try. Stand in front of the mirror. Say “I’ve been behaving as a straight person for years, and now I’m interested in this woman and having sex with her, and I’m curious about what my identity is.” There will be no easy answer. You’re going to have to sit with questioning your identity for a while. It might be years before you figure it out. You might change and grow—as we all tend to do. That’s OK.
Now try to narrow your focus to this particular woman. She doesn’t need to be the site of any grand identity crisis. From a different angle, she’s a babe who thinks you’re a babe, and wants to have sex with you. So what is sex? Is it kissing? Is it oral? Is it fisting? To me, sex is all of these things. Kate is offering you the space to get comfortable. Take her up on that. She’s saying she’s fulfilled by what the two of you already do. Believe her when she says that. Take the pressure to perform off of yourself.
If you decide to go the get-tipsy-first route, talk about it with Kate before you take the initial sip. Drinking before banging, especially the first time you do something, is in a gray area of inadvisability, but I agree that a nice sipping shot or a glass of wine might get you over your intellectual hang-ups, if that’s what they are. Just make sure everyone is on the same page and comfortable with it.
You also might try stimulating her through her panties, trying to give her an orgasm through nipple stimulation, or all sorts of other ways to please a person without confronting the vagina up close. Ease into being the do-er. I’m curious about how active or “top”-like you’ve been with the men you’ve hooked up with. This all might have to do with the dynamics of being the active participant.
Dear How to Do It,
I recently went on a date with a guy who had a severe spinal injury—he broke his back while skiing in his early 20s. The break was at or close to the neck. He had to learn to walk again but made a full recovery in about nine months (!), except that he says he sometimes has “performance issues.” He’s now 40. I like him and am interested in getting to know him further. I have so many questions about this “performance issue”—does he feel turned on, but not get hard? Is it part psychological? Does his sex drive suffer? If we become intimate, I want him to feel good and at ease, and part of making that happen is understanding how his body works.
I realize this is very sensitive territory for a guy. (I am so impressed that he brought it up on the first date!) What’s the best way to navigate this with grace, other than being patient and following his lead?
Dear Hard Question,
Grace is certainly aspirational. But this guy brought up his “performance issues” on the first date? That’s a sign that he’s open to discussing them. Ask—gently.
You could say, “I’ve become curious about your penis,” and let him fill you in. Not especially graceful. Or you could say, “I’m developing a desire to have sex with you, and I want to know what sex looks like for you.” which can open up all sorts of subjects, from the nuts and bolts of his, er, nuts and bolt to what he thinks of as sex in a more general way. All of which is useful information.
Don’t get so focused on his injury that you lose sight of all the other aspects that make a pair compatible. Do remember that whatever the status of his shlong, he’s a whole human with likes and dislikes that may or may not match up with yours. Scout that out before, or as you’re asking about the function of his member.
More How to Do It
My wife and I are in a wonderful, 28-year monogamous marriage. When we were in our 40s, she started losing interest in sex and blamed herself and possibly early menopause. I dove into studying sex techniques. I taught her to squirt, have multiple orgasms, extended orgasms, sensory play, light bondage, etc., plus I started taking her away for three-day sex weekends.
My transformation fixed her interest problems. Early on this adventure, when she was hanging on the edge of an orgasm and having difficulty getting over the edge, I slipped a finger in her butt, and this tripped her over the edge with a loudly expressive, convulsive orgasm. For several months, I only occasionally used this when she was needing a little more spice to get off. Then suddenly she said she did not want me touching her back there. She admitted it had felt good but said it was dirty and gross. I get it—no means no—but when something was so effective, it makes me want to push her boundaries a little. I can’t get her to budge. Any ideas to warm her up to the idea again, or am I being unreasonable?
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