How to Do It

My Boyfriend’s Very Specific Sexual Demand Is Wrecking My Life

I wish we could go back to before he got obsessed with this.

A woman covers her face next to an illustrated key
Photo illustration by Slate. Photos by mar1koff/iStock/Getty Images Plus and PeopleImages/iStock/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,

My boyfriend and I have been together for five years and are very in love. I want to spend the rest of my life with him and hate to imagine breaking up over this—just as a preface. But recently, we’ve been struggling with some sexual incompatibility.

We’ve always had a really active and communicative sex life, but it has been teetering off recently because he wants me to be his keyholder, or the person who holds the key to his chastity device. He also prefers me to peg him rather than to do penis-in-vagina sex. I really understand that he may like to do less PIV, but I’m uncomfortable with being a keyholder. I prefer kink to be more peripheral to my sex life—more like something fun for a weekend, rather than a Tuesday night after work. This has been causing some tension. If I ask for PIV, or even for him to orgasm, he feels resentful, because he’d rather build up to an anal session. He feels that coming too often takes away from his ability to have a prostate orgasm. He also hasn’t been able to have a prostate orgasm (he thinks, but he’s not sure) and wants to use the caging to try to get there.

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I feel a profound sense of loss that I’m struggling to get over, and I am also having a hard time with the cage. I really love PIV with him, and I miss the ease of sex without toys and preplanning. I don’t mind domming on occasion, but it’s not something I feel comfortable doing regularly. I’m also having a hard time getting over the feeling that he doesn’t want to have sex with me—he doesn’t feel that desire the way I do. While I don’t mind pegging, I don’t find it particularly sexy—I find the strap on clunky and disconnecting. It’s very sexy to watch how he reacts, and we’ve found some compromise with me using my hand to move the dildo, but it’s generally not something I want to do every time. He says this makes him feel jealous, because in the past he’s penetrated me every day but I won’t do the same for him.

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We have been having long, emotional conversations about this, but both feel we are giving up something important. He feels if we have PIV or even if he ejaculates, he’s giving up the chance to have a prostate orgasm. I feel as though my boundaries around the cage aren’t being respected, and that I miss vanilla sex. We’re generally non-monogamous, but he’s indicated he has a hard time finding and trusting other partners to do this with. I’m emotionally wrecked and don’t know what to do. Do you have any tips on how to strike a balance between kink and non-kink, topping and not topping?

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— Reluctant Dom

Dear Reluctant Dom,

I have some tips, but for your boyfriend, not you. To hear you tell it (and I’m qualifying here to acknowledge that we’re just hearing one side of the story), you have damn near perfect form. Maybe too perfect, even! You might be generous to a fault. You’re willing to indulge your partner even by participating in some acts that you’re not particularly enamored with or that trigger discomfort, for his sake. However, his satisfaction seems indirectly contingent on obstructing yours. All things being equal (and they aren’t playing out that way—more on that in a sec), you’re at an impasse.

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I don’t know how you can proceed without compromise from both sides. You’ve been compromising; it’s his turn. His desire to pursue prostate orgasms is cutting directly into your desire to continue having sex as you know it. What makes his position less tenable than yours is that it’s based in theory (which, I’m assuming, has been gleaned from reading about prostate orgasms online, probably in the context of his kink). He thinks abstaining from PIV sex will eventually satisfy him. You know that PIV sex will satisfy you. There is often no use in being right in an argument between you and another person, but I think the shaky ground of his argument makes it so that he should at least consider accommodating you. Some people never get that prostate orgasm they’re looking for. Your boyfriend might be one of those people—imagine if he ends up having disrupted your sex life in vain.

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That’s not to say that he shouldn’t pursue his interests, but if he wants to be a big boy whose primary sexual outlet is getting railed, that means accepting the consequences of this kind of experimentation. His current desires are not what you signed up for, and you’re under no obligation to participate. You’re basically at your limit—if he needs more, something has to give. He’s having a hard time finding interested partners and, well, that’s life. He should keep looking. And he should stop trying to manipulate you with the tit-for-tat whining that you mention (“He says this makes him feel jealous because in the past he’s penetrated me every day but I won’t do the same for him”). That’s baby stuff. It irons nuance out of the situation, as these are entirely different activities and it does not follow that if you’re into one, you should be into the other. This is not a situation to “Hey! No fair!” one’s way through.

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You’re uncomfortable, and you’re not into what he’s asking for. He keeps pushing it. It’s his job here to course correct. I agree that it would absolutely suck to break up over this, but sometimes irreconcilable differences show up late to the party, unexpectedly. Even if it’s for the exercise alone, ask him how he sees this situation improving without your participation—tell him to imagine a scenario in which you don’t agree to do the things that you’re uncomfortable with. What are his other paths to pleasure? This is something he needs to figure out for himself, and given the nonmonogamous nature of your relationship, he has the means to pursue them. What a great position to be in. If he doesn’t take advantage of that, it’s on him.

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Dear How to Do It,

I am a woman in my late 50s and getting divorced. We didnt have sex for the last 10 years of the marriage because of my husbands lack of interest and sexual problems. Now I am ready to go, but cant find what I want online. Most of the men want sex once and never want to see you again. I want to find someone to date and have sex frequently. I have a very high sex drive, so just a sexual relationship would be okay for now. But I need at least a little bit of an emotional connection too. I went without it for so long, and now I want it all the time. What do you suggest?

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—Friends With Mild Benefits

Dear FWMB,

I think you should just try to date someone using whatever connecting channels feel right for pursuing that. Instead of explicitly looking for sex in spaces only devoted to hook-ups, look for someone that you’d like to spend some time with. Definitely state your sexual interests up front, but maybe wait a date or two to get naked so as to reinforce your goal of a more ongoing sort of thing. That doesn’t mean people will grasp it, but if you move directly to sex, there’s at least a slightly greater chance that your connection will remain only in that realm, if it remains at all. That “little bit” of an emotional connection you seek is actually going to color the dynamic in such a way that it will look quite different from one that is just a sexual relationship. Even a drop of emotional connection will require a disproportionate amount of cultivation.

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You could easily look into local swingers’ parties/groups, but it really doesn’t sound like that’s what you want. You want someone that you like, that you have good sexual chemistry with, that you want to see again. That’s not something you’re going to be able to order in for yourself. You need more than a few taps to get something that actually covers a range of different connections. A partner like that is special, no matter how casual the nature of your interactions. Finding such a mate requires work, inevitable disappointment, and a decent amount of confidence to state what you’re looking for in no uncertain terms and face the possibility of being rejected for that. But from writing this column, I have a sense that there are people out there who are looking for what you have to offer (especially the skyrocketing libido), and I have little doubt that you’ll find a good match. Just have patience and be kind yourself.

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Dear How to Do It,

Im a 43-year-old male. By choice, I never married or had children. In my 30s, I chose to have a rather active sex life with many different partners. Im absolutely confident I could still get laid regularly if I put forth the effort. I just dont want to anymore. My time is filled with a good job, a small-but-reliable social network, and caring for my beloved German Shepherd. Basically, life is great and Im grateful! I also feel my sex drive slipping away. Im certainly not asexual. I’d enjoy a good fling if the right opportunity presented itself. If it doesnt happen thats also fine. It just probably wont because Im currently putting forth no effort toward that end. Is it okay to just retire” from sex? Ive had my fun. Honestly, its a relief not to think about sex as much anymore. Is this normal? Should I go see a doctor? Maybe a therapist? It just seems to me that at my age I should still be putting myself out there. Im just too busy with things that feel more satisfying right now. I dont want to regret this in 20 or 30 years!

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— Early Retirement

Dear Early Retirement,

You found happiness that doesn’t involve sex? You’d make a mint if you could bottle and sell that. As it stands, think about pursuing a book deal because it seems like you figured out life. Look, the implicit message of just about everything Jessica Stoya and I have written in this column is that sex is an amazing component of life in its idealized state. The steady torrent of questions that fuels this column, however, shows a diverse spectrum of obstructions to said idealized state. Sex often comes with complications, hassles, and consequences—even the most positive sex-positive person will find themselves wondering if it’s worth it from time to time. Cut out the sex, save yourself problems—the allure of good sex, in fact, is why people put up with a lot of shit that they might not have in other situations.

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If you don’t want sex right now, it is your right to abstain. It seems that you’ve arrived at this conclusion quite naturally, after having a good decade of fun. Sounds like evolution to me. Beware, though, that your waning sex drive could be the result of decreasing testosterone, which has implications beyond the bedroom (moodiness, fatigue, and osteoporosis are just some of the symptoms of low T). It might be good to get that checked. Your doctor may suggest hormone replacement therapy. It’s worth a conversation, at least. You don’t seem like someone in desperate need of therapy, so unless you don’t quite have the handle on the situation that you present in your letter, it doesn’t seem like a must, though just having someone to talk to regularly about this stuff is useful to some people who aren’t anywhere near a crisis. If you want therapy, go to therapy.

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There is one thing that you could potentially talk to a professional about, though—your anxiety, whose particular strain is a sort of preemptive FOMO. Who knows how any of us will look back on our choices in a few decades (if humans haven’t been burned off Earth by then)? Worrying about what you might think of yourself in the future is a great way to inhibit your present. Disabuse yourself of this notion. When you make your choices with the kind of clarity and reason that you evince in your letter, you set yourself up to understand your past behavior in the future. You can’t say for sure whether you’ll look back in regret, but you can ensure that you’ll look back in comprehension.

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Dear How to Do It,

Im a 27-year-old man who has never been in a relationship or even had sex, for that matter. Whenever the subject of sex comes up or is hinted at I get uncomfortable and nervous. I dont want to be a virgin anymore, but I also dont know how to act or where to begin when it comes to seeking sexual partners. Where do I start?

— Very Virgin

Dear Very Virgin,

If you bone on principle alone, you’re setting yourself up for underwhelming sex. My suggestion for satisfaction: Don’t have sex because you no longer want to be a virgin; have sex because you want to have sex. Is your lack of sex a result of simple disinterest, or have other things been blocking you? Do you feel lust for other people? That lust is what galvanizes so many—can you put your finger on why it’s not doing the same for you? I don’t recommend moving forward if you can’t answer any of these questions.

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If you don’t feel sexual attraction for others, you might be asexual. As always, I recommend reading Angela Chen’s Ace: What Asexuality Reveals About Desire, Society, and the Meaning of Sex. Whether you are or aren’t ace, the book could give you some useful language.
Talking to a professional, especially a sex therapist, could also help you unblock. It would be unwise to go from zero to orgy-frequenter overnight—more power to you if you can pull it off, but I think easing in is going to be the safest course of action for you. Partners that you care about or at least find sexy will also help the process. Try to see things less in terms of taxonomy and more in terms of managing desire. After the first time, the “virgin” label will no longer apply to you. Then what? That’s for you to figure out.

— Rich

More How to Do It

My question has to do with casually viewing porn on the internet. If you believe the New York Times, child pornography is basically everywhere. As I am someone whose tastes run to younger-looking, smaller-breasted women (but no kids!), I am concerned about the possibility of accidentally viewing something illegal. Just how hard—or easy—is it to run across that on the major porn sites?

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