How to Do It

I Accidentally Made an Eye-Popping Discovery About My New Boyfriend’s Sex Life

Do I tell him?

A woman embraces a man.
Photo illustration by Slate. Photo by Drazen Zigic/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,

I’m a woman in a new relationship, and I recently made a discovery about my boyfriend of 10 months that I’m not sure what to do with.

I won’t say why, but I found out my boyfriend is paying for sex sometimes outside the relationship. This is not “allowed,” as we’ve never officially had hall passes, but we’ve hinted at sexual non-exclusivity as being something we’re open to. I’m honestly not really upset—since the sex he is having is purely transactional (and, as far as I can tell, with a safe professional), to me emotionally it’s not a big deal. Even if it was other platonic sex I think I’d be fine with it. Our sex life is solid and I like other parts of the relationship. But at the least, I’d like him to be able to tell me if he’s not sexually satisfied and be honest. I care more about that than what he did to solve the problem, if that makes sense. Should I talk to him, and how?

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—Extracurricular

Dear Extracurricular,

The why, or more importantly how, of your finding out about this is pretty important. If you were looking through your boyfriend’s phone or emails, you’ll need to start with an apology. This might need to be an entirely separate conversation from the conversation about his sexual activities. If you found out through other channels, you can ignore this paragraph.

Even though you profess not to care about what you found out, the language you’re using—”not sexually satisfied” and “what he did to solve the problem”—suggests you might be feeling like you’re deficient in some way, or like you must meet all of your partner’s sexual desires. That isn’t always possible. Sure, people often have this pernicious idea that the two people in a couple should be able to meet all of each others’ needs and desires, but that doesn’t seem to be the case in practice for many people. There’s a big chance that he gets something out of these transactional relationships that can’t be replaced by a partner.

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Still, you are correct—he should have talked to you about this. It sounds like you want to stay in the relationship. If that’s the case, spend some time thinking about what you know you bring to the relationship, and reminding yourself of what you appreciate about him. Then bring it up. If you haven’t been snooping, you can simply tell him you’re aware he has other sexual partners and go from there. Pick your time wisely—when everyones’ biological needs are taken care of, when you have plenty of time to talk and deal with complicated emotions, and when you aren’t likely to be interrupted. Good luck.

Dear How to Do It, 

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I think I’m going to sound stupid, but I’ve been at kind of a loss. My boyfriend loves when I give him head, but it’s gotten majorly in the way of our sex life. I don’t mind doing it a few times a week, but now he wants it virtually every time. I’m hesitant to talk to him because I’m pretty into BDSM and he was a little worried about dominating me. I still want to be dominated and I’m totally OK with him having push me down on my knees every now and then, I would just love it if the ratio changed a little. I don’t even know if he realizes how little we’re actually having sex since he’s getting off every time. Is there a good way for me to ask that I just get a little more PIV time?

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—Choking on Regret

Dear Choking on Regret,

Tell him that you love how in-charge he has become—and then tell him that you’re missing penetrative sex. His response will let you know whether he’s open to taking your desires into account or not. You don’t need to overthink this. Remember, you have just as much power and agency as the person who is in the dominant role.

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Dear How to Do It,

I’m one of those lucky people who figured out how to masturbate as a child and have not had to change techniques since. For context for the parts we’re working with here, I’m a cis woman. Basically, I grind the palm of my hand against my pubic bone, so I’m applying pressure to my clit and basically my entire pubic area. I can reliably get off this way in a matter of minutes. They’re not always Earth-shattering orgasms, but they get the job done. I’ve tried a vibrator, both internally and externally, and I would say about every 10th time I have a truly Earth-shattering orgasm, but almost every other time the battery literally dies before I’ve even come close to coming. And so, in my several years of being sexually active, I’ve only gotten off by a partner once or twice.

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This new guy I’m with has particularly adept fingers, and we’ve been in a lot of positions where he’s stimulating my clit while inside me and I am really loving that, but still no orgasm! I tried using my tried and true technique while I was stomach down and he was entering from behind, but my fingers were kind of getting in the way of his dick, so I stopped. I’m getting frustrated with myself because when I’m masturbating, I can’t stop myself from using my palm grinding technique because it just works so well. Is there anything else I can try to break out of this singular technique? Not just for partnered sex but even just for myself—it gets the job done but it’s boring.

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—Prison of My Own Design

Dear Prison,

There are so many different kinds of vibrators out there, and you may find something that works well for you if you keep auditioning other types. HeyEpiphora.com is a great resource. I’m partial to the ones with a little nub that encloses the clitoris, and hear great reviews from other users, so if you haven’t tried one of those that’d be my first step.

For partnered sex, you might try being on top in a way that grinds your mons pubis into his pubic bone. Think less upright cowgirl and more laying on top of him. It might also help to keep one of your legs between his and the other on the outside of one of his legs. You can also squeeze his dick between your legs while rubbing yourself on the crease between the base of his dick and his pelvis.

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You can also ration your patented palm-grinding technique as a once-a-week thing while you’re trying to train your body to respond with orgasm to other types of stimulation. Cutting it out entirely is likely to leave you frustrated in a way that’s untenable, but wall-climbing levels of arousal are what’s most likely to set yourself up for success with other forms of pleasure.

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Dear How to Do It, 

I am a 28-year old straight woman. For my entire sexual life (13 years), penetration has been excruciatingly painful for me. For 10 years, I have pursued a solution. Please believe me when I say I have tried EVERYTHING. I have seen so many doctors, including some of the most well-known experts on female sexual pain; I did over a year of physical therapy; I’ve done sex therapy, regular therapy, and so many medications and creams. But the pain remains. The next stop on this tour is a surgical solution.

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But I recently realized that I am not even interested in penetrative sex anymore. It’s not sexy to me because it’s so medicalized now. The only reason I am still doing this is because I feel like I need to be able to have “real sex” to find a long-term (assumed cis) male partner. I thought about saying no to penetration forever and felt immense relief and happiness.

However, when I shared this with two close friends, one told me I was giving up on myself, and the other told me she was happy for me but it would be almost impossible to find a long-term partner who will “settle for someone who can’t have sex” (so what, only PiV penetration counts as sex?). Now I’m doubting myself. Can you weigh in? Is saying “no” to penetration forever an empowering choice or giving up? And will it really be so hard to find a male partner who is willing to forgo penetration and find other ways to have a fulfilling sex life together?

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—Wow. Settle. Ugh.

Dear WSU,

You felt relief and happiness when you considered taking penetration of the table permanently, and that’s a strong message from yourself. Finding a long-term partner is simply hard regardless of what your specifics are. We all have our potential deal breakers: You don’t do penetration. I’ve done porn for 15 years. Some of my friends are non-binary, others want children raised in a specific religion, and still more are very specific about what they need to find a person attractive. Dating, no matter our particulars, is a process of sorting through potential matches until we find ones that click.

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The further from heteronormative you are, the more likely you are to encounter reactions ranging from rude to judgemental. The upside is that people who are going to react in that direction tend to do so early, making the dating process that much more efficient. I like to make sure the other person is aware of my job before the end of the first meeting. If I’m on a dating app, I might get it out of the way before we meet. How and when you broach your boundaries is entirely up to you—my career is inherently public, while your pelvic pain is probably pretty personal. If you’re nervous about bringing it up the first few times, warming up with general discussion of sex can be helpful, and preparing what you’ll say and even rehearsing it in the mirror can also ease anxiety.

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You also might make a short list of things you can do to take care of yourself if someone becomes emotionally hurtful. Leaving is a great first step. Maybe you have a third friend who can be more supportive? Sitting in water can be soothing. Whatever you do to help yourself return to balance, make sure you’ve got it waiting for you in case you need it after a bad date. Good luck.

More How to Do It

Well: I saw my girlfriend of six months being orally pleasured by her dog. She doesn’t know I saw her.

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