How to Do It

My Husband and I Had a Bad Threesome, and Now I’m Questioning His Character

I just can’t this out of my head.

A woman looks pensive next to a neon 21 sign crossed out.
Photo illustration by Slate. Photo by fizkes/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 in a happy, stable, loving, open marriage. We’ve been together two decades and have two children. A few months ago, we went to a sex party and he met a nice young lady. She said she was a lesbian just starting to experiment with men. Subsequently, we were both texting/flirting with her and finally had her over. During the threesome she was WAY into his dick (which, to be fair, is great), and I felt sidelined/ignored by both of them. It was the least pleasant threesome I’ve had—not a disaster, but not something I want to repeat. Since then, he has continued to see her. They are having hot sex and he’s thrilled.

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The issue? She is 21. We are in our 40s. When we first met, I assumed she was in her mid-20s and did not clarify—although I still had misgivings and felt that was too young for me! She’s smart and seems relatively sane, lives independently, has a job and a college degree, and seems to be close to her parents as well. Up to now, my baseline assumption would be that any man who sleeps with someone less than half their age is a predatory creep. I feel like this reflects poorly on him and bodes ill for the future. But I’ve talked to some poly friends who shrug and say if she’s legal, it’s fine. I have never exercised a veto before, and I don’t want to do so now, especially since part of me feels like I’m just hung up from being rejected. I am really in my feelings about this and it’s hard for me to sort it out. What do you think?

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— Dirty Old Woman

Dear Dirty Old Woman,

Many things can be true at once! Your feelings of rejection may have increased your sensitivity to the situation, which is an eyebrow-raiser, even from my completely uninvolved perspective. If you felt accepted and super into her, you might be willing to overlook the stark age difference along with your husband. I’m not convinced that your bias and jealousy are clouding your judgement—more likely, distance is affording you clarity. People in their early 20s are generally inexperienced and more likely to take risks/overlook (or simply not be aware of) the repercussions of their behavior. I mean, your husband has a dickmatized 21-year-old lesbian on his hands—how much experience could she possibly have in this specific arena? How could she even have a concept of how things might go, and any resulting emotional collateral? I think your side-eye is in order.

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That said, I tend to agree with your poly friends that in purely sexual terms, this much of an age difference doesn’t have to be an issue. Young, horny people are going to find a way to have sex, and with a certain mindset, it won’t matter if the good dick they’re getting has been on this earth for as long as they have or twice the amount. But I also think knowledge and experience afford a certain amount of power, especially when the knowledgeable and experienced party happens to be a guy and both parties happen to live in a patriarchal society. And so, it’s really important for that guy to be careful with the younger person’s feelings and to be clear about the parameters of the relationship, with regular conversations. You can assume that as an adult she will be able to handle and advocate for herself, but you also shouldn’t be surprised if she turns out to be deficient in those areas.

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I think your challenge is to test your assumptions. Take stock, observe your husband insofar as you are capable, and ask yourself if you were right: Is he a predatory creep? Sweeping generalizations are like 21-year-olds: capable of being right on, but prone to falling apart before your eyes. For the sake of keeping the peace, I think it’s best if you watch closely and speak up only when you can raise concerns that he doesn’t seem to be considering. It’s your job as a partner to draw attention to oversight. You’re his backup eyes. But I think that’s about as big of a role you can play here unless you really want to revise the terms of your agreement. Unless you actually do want to introduce vetoing, it’s going to be hard to put the 21-year-old back into the bottle without major drama.

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Dear How to Do It,

I’m a straight cis woman who has been in a four-month relationship with a trans guy I’ll call Jay (he/him). He is hilarious, kind, empathetic, and smart, and although I’ve never dated a transmasc person before, I’ve always thought of myself as attracted more to someone’s personality than by their physical attributes. I’d known Jay for several years, including those when he was living as a woman, and have supported him through his transition. He chose to undergo top surgery a couple of years ago to help with his dysphoria, but is leaving the downstairs alone—in his words, “I don’t need a dick to be a man.” I find his confidence in living authentically as himself very admirable, and we have worked through what makes him most comfortable in bed. (For example, when it comes to giving head, I’ve learned that he likes a degree of roughness: pushing/pulling, taking the whole pubic area into my mouth to suck.) For the record, I love being in a submissive role, while he prefers being dominant.

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Here’s where I’m hung up. Despite the surgery, he is still not very comfortable having his chest or nipples touched—something I’ve always enjoyed doing very much with cis male partners. And although I feel absolutely terrible for feeling this way … I miss a penis in the mix! We use toys and strap-ons, but there is nothing to match the feeling (for me, as a submissive) of being crushed and filled with warm, living flesh—flesh that I know is enjoying my body as much as I’m enjoying being penetrated.

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I really hope I’m not transphobic, but I worry that these thoughts and desires would hurt Jay TERRIBLY if I were to share them—it seems like pretty much the worst kind of rejection for a trans guy. I’ve been starting to think that the kindest thing to do would be to split up with him, despite the awesome connection that we have in all other respects. But the thought makes me feel incredibly sad—and cruel! Is that my only (kind) option here? Or is there a way to discuss these very sensitive topics without absolutely crushing Jay’s hard-won (and very sexy!) self-confidence?

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— Confused

Dear Confused,

On one hand, Jay is an adult, and adults must endure tough conversations they’d rather not have. On the other, dysphoria is a bear. Even after surgery, it seems that he is still dealing with dysphoria, so I think the best course of action is to tread lightly here. Technically, you’re entitled to free expression and not obligated to the sensitivity I’m suggesting, but sometimes being a compassionate person means relinquishing some of your freedom to spare someone else’s feelings. I don’t mean that you should worm out of this relationship with no explanation, but I think for everyone’s sake, keeping things vague might be useful, if you go that route. Where does this rupture in the sexual connection leave you? Unsure of your future with him, conflicted, and kind of sad. Sharing this specific information might be all Jay needs to understand that this relationship’s prospects are not looking good. If he wants to know more, let him ask for it and even then, be sparing with the details. Saying that you’re not feeling a sexual connection is going to be more useful than composing an ode to cis-dick. If it gets to the point where you feel you have no other choice but to reveal the extent of your feelings about having sex with him, warn Jay that the conversation you’re about to have may trigger dysphoria. Then he can decide if he actually wants to go forward with the talk. You also have the option of requesting an open relationship. By many standards, it’s early in your relationship to be doing that, but it might be what you need to preserve things.

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I don’t think it’s useful for you to beat yourself up about this, though. You tried, but it’s looking like Jay isn’t for you. Not everyone is for everyone. I don’t want to let you entirely off the hook because transphobia is so baked into our culture that this is worth thinking about some more, but I’d be a hypocrite if I suggested that you had to alter yourself and live without the kind of dick you want. I sure couldn’t! That said, it’s probably worth looking at Jay as the specific human he is, and not as a representative of a group. Every partner will have fixed traits and habits that you will jibe with or not. If Jay were a cis guy who wasn’t into giving oral or whose dick was too something (short/fat/skinny/long/ugly/curved/pink/purple/cut/uncut/etc.) for your taste, you’d be much in the same boat. Not everyone is going to be an ideal partner, and it sucks to have to make that call, but when you care about someone, that call is going to suck irrespective of their gender identity. You’re four months in. For many, the point of dating is figuring out exactly what you have: whether the person in front of you is a long-term prospect. Signs point to no here. It’d be far crueler to lead him on.

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Dear How to Do It,

I am recently married and bisexual. I didn’t get a chance to date many women before I met my husband (partially due to coming out a bit later in life, partially because it’s easier to find straight men than gay women to date). I’ve recently been missing this part of my identity, and have been struggling with the feeling of “missing out” on dating women. My husband is OK with me dating other women casually, but isn’t interested in dating anyone himself. He’s worried I will end up leaving him for them, and a part of me is worried he isn’t really OK with this despite him reassuring me that he is. Is exploring with his blessings the right thing to do? And if so, why do I feel so guilty about it?

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— One Way

Dear One Way,

How OK is your husband with you dating a woman if he’s also worried you’re going to leave him? Sometimes people say they’re OK with something, and then they say they’re not OK with something and they really mean the latter but your horniness compels you to believe the former. It’s annoying to have to think for adults and to ferret out what they actually mean when your relationship is theoretically based on openness and honesty, but it’s a necessary inconvenience sometimes when navigating the highly uncertain and insecurity-instilling world of nonmonogamy.

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I’ve taken the route that’s tempting you and had sex outside of a relationship where that was technically allowed but a consistent point of tension. It just created chaos. It felt wrong no matter how often my partner said it was right because it consistently came back around to bite me. Though we had essentially banished the concept of cheating from our relationship, I was punished with rage and resentment as if I had callously betrayed him. I don’t really wish that on anybody. If you go forward with things as they are, you may face major strife. I think it’s important to square your husband’s seemingly conflicting feelings before dipping a toe in. How can he be OK when he is so insecure at the same time? What would make him more OK and less insecure? And how could you both work to tend to his feelings without saddling you with joy-obstructing guilt? I think you should go back to the drawing board and figure out a more solid plan, boundaries, and how to balance the equation.

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Dear How to Do It,

I have been with my husband for 25 years. Always monogamous, mostly happy. Except in that entire time, we have only had sex initiated by me a handful of times. Hes always too tired when its my idea, and I feel annoyed and rejected and just dont try again for a long while. We have sex frequently enough for exhausted parents, and I almost never say no when he initiates because I can usually get in the mood. I find this one-sidedness even more irritating in our 40s, though Im not even sure why. What gives?

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— My Turn

Dear My Turn,

If you’re not sure why you feel what you feel, I can’t be either. But I can guess that you’re frustrated that things seem lopsided. Egalitarianism is noble and worth striving for, but in some facets of our relationships, it’s not practical in its purest form, and pursuing it to the T can lead to some petty tit-for-tat squabbling that ultimately wastes time. It seems like, for whatever reason, your husband prefers to initiate sex, which works because you’re able to usually get in the mood so that the act can be completed. It seems when the dynamic is inverted, though, he can’t get in the mood. This might just be how his break and accelerator function, and while an explanation would be interesting and probably help you deal, the reasons why may never be clear. Let’s just assume your husband’s wiring is operating your shared machine. You could say, “Hey no fair!,” but look: The machine is working. You might want more variety, you might want reciprocation, but not everything we want can be achievable with one partner. So we make do. From an outsider’s perspective, you’re doing just that. Since this is bothering you, a conversation is in order, but come to it without accusation and with willingness to accept your partner. You’ve been together for 25 years, you’re in your 40s, and you’re having frequent sex (or at least, frequent enough). You’re kind of killing it.

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— Rich

More How to Do It

I’m a bisexual woman in my early 30s, and I’ve been in a relationship with an amazing woman for the past nine months. We both care about each other deeply, and it’s the happiest and most stable relationship I’ve ever been in. Here’s the thing, though: Before her, I’d only ever slept with and dated men, while she’s dated almost exclusively women. I feel painfully inexperienced compared to her, which is uncomfortable for me because I’m used to being the more experienced one. It kind of feels like being a virgin all over again. For what it’s worth, these worries are all coming from me—she has never made me feel bad about my bisexuality or my past relationships with men. But I can’t stop worrying. To me, the sex in our relationship is great—but what if she thinks something is lacking? Mostly, I worry that I might not be as good as her exes (several of whom are “gold star” lesbians). How do I compete with that?

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