How to Do It

I’m a Straight Man Pushing 40. I’m a Little Startled by the New Reaction I’m Getting From Women.

A man with a "This guy!" photo.
Photo illustration by Slate. Photo by razyph/Getty Images Plus.

How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!

Dear How to Do It,

I’m a straight male “freshly” out of a long-term relationship. We started separating over a year ago, but continued to live together. Pandemic, etc. We also thought about co-parenting our young daughter while living together. It wasn’t awful, but even with therapy, the problems that led to our relationship ending persisted. But now I’m finally on my way to a new place that I will have completely to myself 50 percent of the time. Leased signed, movers booked. Custody sorted, completely on the same page with my kid’s mom on all things co-parenting. I still get sad at times, and it’s not all peaches and gravy, but I’m honestly looking forward to the future. And quite hopeful.

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All this to say, I’m very ready to meet some women and have some fun.

I’ve actually started that, and that’s what I’m looking for help with. Not with meeting people—I’ve had surprising success meeting people on the dating apps, have had an introduction to a mutual friend in a similar situation, and have even reconnected with an old college classmate and an ex-girlfriend.

Please believe that this isn’t a humble brag. I’m legitimately surprised. I’ve only been in a handful of relationships in my life, and most of them were short. Sex was an important part of all of those, but I’ve also had years-long dry spells. Casual sex has never been a part of my life. I guess I’m more attractive pushing 40 than I was in my 20s and 30s? I really thought I’d have a much harder time meeting somebody, never mind multiple people. I’ve never dated more than one woman at a time before. And I may be putting the cart before the horse here, but now I’m in a situation where it’s possible and I’m considering it. More than that—I want to do that. I think.

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So I guess my questions are: What should I be telling the women I’m talking to and/or dating, and when? How do I know if I’m really not interested in a monogamous relationship, or if all this attention is just going to my head? Part of me feels like I’ve been conditioned to want a monogamous relationship, but another part of me wants to keep things completely casual, and not even commit myself to one person. That’s very exciting to me, but it also feels selfish. I can be a real people pleaser, and the thought of potentially hurting people by putting myself first like this gives me great pause. Any advice would be greatly appreciated.

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—To Be (Committed) or Not to Be

Dear To Be,

Take some time to think. For some people, that’s taking a long shower or a walk; for others, that’s journaling for more than 30 minutes or making a list; and for still more that means talking through it with a friend who you can trust to give you real feedback. Maybe you use more than one method. What do you want out of your sexual relationships at this time in your life? What are you willing and able to put in? Do these two things seem balanced to you? Ask yourself why every step of the way: Why do I want this? Why do I feel “selfish”? Why do I have this boundary? Why do I need this particular thing?

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Once you’ve got an idea of what you want, communicate that as early as seems appropriate. The ideal timing will be different with every potential partner, but should be done before you have a significant amount of sexual contact—not necessarily before the first kiss, but definitely before the first orgasm. If she brings up relationship structure desires or needs, that’s a cue to share your own wants and boundaries. If the person seems to be very presumptive of monogamy as the default, you’ll want to be extra clear at an earlier time.

As a self-described people pleaser, this last part might be a struggle for you—in my experience, people pleasers are sensitive when they perceive a person to be mad at them. People might get upset. They might judge you. They might even yell at you. They might have assumed interest in monogamy—what they think of as “normal”—and take their confusion or disappointment out on you. Their paint-by-numbers ideas of what relationships are supposed to be aren’t your fault, or responsibility, but it can be difficult to experience the anger that sometimes gets directed at people who live outside that script. Remember that you can walk away from a conversation at any time, that there is no one right way to do relationships or sex, and that you can fall back on all that introspection you’ve done when you’re second-guessing your motivations.

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Dear How to Do It,

I’m a woman who recently started dating a good friend of mine. We’re both in our 20s. He’s been my only sexual partner ever, although he had several before me. We are a great fit in (almost!) every way, and the sex is great. I’d always thought I was a little kinky, and I was excited to explore my sexuality. He is also into non-vanilla sex, and we’ve spent the last few months acting out a lot of our sexual fantasies together, mostly around bondage and domination/submission.

Here’s where my problem comes in: We’d both prefer to be the submissive/bottom in the bedroom. So far, as I’ve been getting comfortable both with sex overall and BDSM more specifically, we’ve taken turns dominating one another. He identifies as a switch and is a terrific dominant but still needs and wants to be in a submissive role half the time.

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I never thought I’d be into being dominant, but it’s been really rewarding to switch for me as well. As the dominant, I don’t get as turned on or have explosive orgasms the way I do as a submissive, but I have found a lot of pleasure in fulfilling his fantasies around submission.

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Here’s the fantasy I can’t seem to figure out: Part of what turns him on is being forced into submission. So, he wants to “fight” back and ultimately be physically overpowered or restrained. He’s only a few inches taller and maybe 15 pounds heavier than me, but a lot of that is muscle, and I can’t seem to get him overpowered or restrained without his cooperation (not for lack of trying!). At the beginning of our relationship, he would passively submit so that I could get comfortable with the dominant role, but now that I have more experience, he’s started resisting when I try to top him. Several times now I’ve set out to dominate him, but it’s ended up with him taking over “the scene” and restraining/dominating me since I wasn’t physically strong enough to win.

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When we’ve talked about it, he wants me to figure out a way to force him into submission, whether that’s via speed, some quick-fitting restraint, or something else. I need tactical advice on how to restrain someone bigger than me without permanently hurting him. A few times I have left bruises! This feels like a weird question to Google, and I’m hoping you may be able to steer me in the right direction. Separately, and this is maybe harder, do you think I’ll ever be as sexually fulfilled in a dominant role as I am in a submissive one? Can people learn to overcome their instincts and be turned on by new things?

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—Wannabe Domme

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Dear Wannabe,

Regardless of apparatus, what will help you speedily restrain your partner is practice. Pick whatever form of restraint you feel most comfortable with and run drills. Get the hang of it at half speed without him fighting back. Then try a little faster. Keep going until you can apply the restraint as quickly and seamlessly as needed. In the meantime, or if you struggle to get the hang of that, he might still find enjoyment in fighting against restraints once they’ve been applied with his cooperation.

As for sexual fulfillment, you might reframe your dominance as service. If your joy in submission involves pleasing your partner, there’s an angle here in which dominating him—which brings him pleasure—is a fulfillment of your sexuality as it already is. And you may find that as you experience sexual pleasure in a role you’re beginning to expand into, you become more aroused by certain activities.

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It’s also possible that domination never becomes enjoyable for you, and that’s OK. As long as you’re taking turns in the power position both of you enjoy most, I see nothing wrong with engaging in sexual acts that are solely for the benefit of your partner. Keep an eye on the balance, and do regular introspection around your boundaries and interests. Maybe that takes the form of journaling, speaking with a trusted friend, or some other way of checking in with yourself.

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If your sexual interactions become all about him all of the time, that’s a problem that needs to be addressed. Good luck.

Dear How to Do It, 

I’m a single woman in my 30s, and I like to masturbate to porn. You can find a lot of curious things on the internet, and I’m surprised at what’s turned me on. In particular, I’m turned on by some videos that I’d NEVER want to happen in the real world, to me or to anyone else. Are you familiar with “chikan,” a Japanese word for gropers on the subway? There’s a whole porn genre of it. It’s 100 percent sexual assault, and I feel terribly guilty watching it. I do watch it, though, and when I do I imagine the groper is my boyfriend (not a stranger) and he’s discretely feeling me up on the train, consensually. But I have to ignore the actress saying “no” and pushing the stranger away. In some videos, it escalates way too much toward rape and I have to turn off because that’s disturbing, but sometimes the actress eventually gets into it and so do I. Is this wrong to watch if it involves actors and not actual victims?

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—Deep Web

Dear Deep Web,

I’m aware of at least one subway location in Japan that appears to be used for pornography. And there are definitely subway sets that are used for more hands-on sex work to fulfill individual fantasies. My point being that the videos you’re seeing, especially the ones that involve significant sexual interaction, are likely professionally produced with performers who are consenting to the work.

If you’ve got the cash, you might consider commissioning a custom video involving consensual groping. If you’ve got cartooning talent, you might make your own erotic comics. You might write your own stories, visualize what works for you best, or even enlist your partner into a roleplay. Do what makes this feel OK for you, but it’s not inherently wrong to have these fantasies or watch porn that dramatizes them.

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Dear How to Do It, 

I am in a long-distance relationship. It becomes difficult to keep sex interesting when we are so far apart. So we have resorted to sexting, which is great. We both have our toys that we use when we are apart from each other. But I have wanted to bring the toys into the bedroom. I did bring this up to my boyfriend in the best way I could think of but he said “No, we are not doing that. Why would you want to bring something into the bedroom that helps you finish when I am here?” He sees the toy as competition rather than a literal toy to have fun with (in my opinion). Do you think it is worth it to bring this up again? And if so, how do I help him see that I am not trying to replace him with a toy?

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— A Little Help

Dear A Little Help,

How attached are you to this guy? If I were in your position, I’d be struggling to refrain from rolling my eyes as I walk out the door. Many straight men gain a sense of sexual worth from providing orgasms. They want to know how many; they want to be the only orgasm-providing stimulus in the room. Their egos flare up when they feel deficient, and they often do fear being replaced. It’s boring, it’s outdated, and it’s tired, but it’s also pretty typical.

If you insist, ask him—coming from a place of curiosity and speaking with a genuine question mark at the end—whether he feels like you’re trying to replace him. Let him talk. Listen, and allow silent moments. You can also ask follow-up questions, like what exactly his emotions are and why he feels that way. Another line of inquiry is what his thoughts are on what sex should be, where he got those ideas from, and, once he’s laid them out, if he’s willing to broaden them. Good luck.

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I’m a woman in my early 30s. About a year ago, I started dating a man around my age from an app. The relationship became sexual quickly, and it has remained more or less the same since then. We’d have dinner once or twice a week, and sometimes he’d stay at my place the whole weekend. We’re both busy, and I work long hours at home, so this balance made sense for us. But I really did like the guy and it seemed like we were moving toward something more serious. He texted me constantly and was pretty doting. 

A few weeks ago, I invited him over as usual, and he said he was leaving town to travel for a week. He phrased this weirdly, I thought, so I talked to him more, and it seemed clear he was going out of town with another woman. I asked him directly and he confirmed it. He even said he’s actually been seeing this other woman longer than me! I asked if she knew about me, and he said she “also” knew they weren’t exclusive. I did not know that about us. He could tell I was surprised and apologized, and said we could talk more when he got back. I haven’t returned his follow-up messages yet. In a conversation about this with a friend, she pointed out that we never talked about exclusivity and said it had seemed casual, and that’s true, but after a YEAR, is it really possible he failed to mention a whole other girlfriend to me by accident? At the very least he could have said, after we spent Christmas together (!) last year, that he still intended to sleep around. We’ve always used condoms, so I’m not that worried about STDs, but I feel really duped. 

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