I’m a Gay Man Who Wants Sex With Women

I’m Zachary Zane, a sex writer and ethical manwhore (a fancy way of saying I sleep with a lot of people, and I’m very, very open about it). Over the years, I’ve had my fair share of sexual experiences, dating and sleeping with hundreds of people of all genders and orientations. In doing so, I’ve learned a thing or two about navigating issues in the bedroom (and a bunch of other places, TBH). I’m here to answer your most pressing sex questions with thorough, actionable advice that isn’t just “communicate with your partner,” because you know that already. Ask me anything—literally, anything—and I will gladly Sexplain It. To submit a question for a future column, fill out this form.

This is an edited and condensed transcription from last week’s “Sexplain It Live,” which was recorded on Men’s Health‘s Instagram. I was joined by Chrstine Emba, author of RETHINKING SEX: A Provocation.

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I’m a 48-year-old man who’s identified as gay since I was 25 and has never had sex with a woman. But now, I’m beginning to realize that I’m bisexual. Bisexuality really wasn’t a thing 30 years ago, so I didn’t think it was an option. My question is: How do I go about meeting and sleeping with a woman? Do I tell her that I’ve only had sex with men, or no need since it’ll likely be a one-night stand?

CE: I think honesty is the best policy. Still, in a one-night stand, I don’t know that we have to disclose everything about our history unless it’s pertinent and affects what we’re doing [sexually] now. But if we’re trying to start a relationship, you should give the person a heads up because it’s a big part of who you are. That said, are you only trying to sleep with women, or are you looking for something more? Because women aren’t objects to test out your sexuality. You can’t just use them to fulfill your desires. You also need to think about the other person, their feelings, and what they want in this encounter. So I wonder if the framing [of this question] is also something that we should look at here.

ZZ: Yeah, absolutely. You don’t want to use a woman and dispose of them after just because you’ve never had sex with a woman. That said, I think there’s a way to be clear about your desire for casual sex. When you are transparent about your wants, it gives the other party the ability to fully consent to what you want to do. Also, in general, I think disclosure is helpful, and not because you are obligated to disclose to them. But because if you’re anxious or in your head because you’ve never had sex with a woman before, you’re not gonna be able to enjoy the experience. You’re not gonna be able to get it up, or whatever it is. So I think just disclosing everything makes the experience more comfortable.

CE: Yes.

ZZ: It also lets them know that it’s not their fault if there are any issues in bed, or it explains why you’re terrible at eating a woman out. You have no experience! So this lets them know why. Also, I know of women who love the idea of taking a gay man’s virginity with a woman, and that would be a super turn-on for them. So all parties would get what they want from each other. They like the experience of being able to teach you, being your first woman, and you get the experience of having sex with a woman, but this only happens when you disclose. So I would just be direct in your dating app bios. Say, “I’ve identified as gay forever, but really wanna experiment with a woman. I’m super nervous. Is anyone down?” Lay it all out on the table!

I often end up in relationships where all the plans are on the other person’s terms. They’ll say, “I’ll let you know when I’m free next week,” and I’ll end up having to leave every night open because I want to make sure I get to see them. How come I never get to be the “I’ll let you know when I’m free” person?

CE: It’s so interesting. There’s the question, but then there’s a whole different stratum underlying the question.

ZZ: Oh, always.

CE: So with this question, is it about free nights, or is it about power? It actually sounds like this person wants to be the person who directs the relationship and calls the shots. So the question really is: How can I be the person who’s in control in more of my relationships, as opposed to the person who feels controlled. My view is that I think relationships shouldn’t be antagonistic with one person trying to have power over the other person. You want them to be fifty/fifty, or, better yet, one hundred/one hundred with both people fully invested.

ZZ: Totally.

CE: Maybe that’s also something to be attentive to. So ask yourself, “Is the person as into the relationship as I am?” Like that should be a baseline categorization for whether you move forward. And then make sure and have boundaries and be clear about them. You don’t have to wait around for somebody to be free. You have stuff to do in your life. You can go do it and tell the person, “I’m busy, let me know, but I may not be able to join you.” Establish the norm that you’re also a human being with needs, desires, and your own schedule. And they need to respect that. If you don’t want a relationship only on someone else’s terms, don’t settle for a relationship like that. Tell them. Don’t settle for relationships where you don’t feel valued.

ZZ: I think there’s always the fear that if you advocate for yourself, this person will leave you. Right? Because otherwise, why wouldn’t you have done this beforehand? You could easily have responded to “I’ll let you know what my schedule is” with, “Okay, well, my availability for next week is Tuesday and Friday, so let me know sooner rather than later.” That’s all it takes. But they haven’t said anything like this because they fear they won’t be able to see them if they do. Still, you have to be willing to take that risk. Also, if they don’t put in that minimal effort to see you, you shouldn’t be with them. Like, yes, I know you don’t wanna lose them, but you can’t do everything on their terms all the time. So, in summary, I see a lot of fear here, and that fear is what’s allowing this power imbalance. You need to be willing to lose them.

Watch the full conversation here: