How to Do It

Can I Let My Bisexual Boyfriend Sleep With Other People—but Only Men, and Only on Top?

Photo illustration of a woman looking over at a man texting in bed.
Photo illustration by Slate. Photo by SanneBerg/iStock/Getty Images Plus.

Dear How to Do It,

I’m a straight(-ish) woman in a relationship with a bisexual man. (We’re both in our early 30s.) He told me, soon after we got intimate, that he’s had sex with men for most of his adult life, though he’s only ever dated women. We got more serious, and we’re now exclusive and a year into our relationship. He’s always said he’s willing to be a one-person guy but would like to open things up when I feel ready, because he does have a high sex drive and desires that go in a lot of different directions. I now feel ready for this, but I’m struggling a bit with the limitations that I want to put on the situation. I really only feel OK with him seeing other men for sex, not women, and I’m not comfortable with him being the receptive partner with other men. This is mainly because of higher risk of STIs, though he’s said he would go on PrEP, but I also am just not comfortable with the idea of him putting himself in a vulnerable position with another man. (He said he’s done both positions in the past.) Are these reasonable boundaries to have, or am I overstepping? The discussions are just beginning, and I haven’t told him how I feel yet.

—Rules of Engagement

Dear Rules of Engagement,

I’ve noticed in my limited research on polyamorous people that veto rules are rather unchic. That is, most people I’ve talked to and read about within that community aren’t OK with their primary partners dictating the terms of any of their other partnerships (including whom those partnerships are with). It’s a lovely philosophy, the idea that the bond of love needs no rules, as well as a potential working example of the cliché that goes, “If you love something, set it free; if it comes back, it’s yours.” But I am sure it’s not without its drama. Personally, I can’t imagine an open scenario that isn’t informed by my partner’s wishes. (Granted, I am not poly, just slutty.)

So, speaking on principle, I don’t see anything wrong with you setting stipulations that will help make your partner’s dalliances more palatable for you. Practically speaking is another matter. I think, in general, you have to understand that his brain off sex and on sex are two very different entities. You can tell him you’d prefer that he didn’t bottom, but don’t be surprised if he ends up doing so because his dick was hard, the other dick looked like it needed a friend, and one thing led to another and his butt inhaled it. It’s really hard to referee each play remotely, though I think a general expectation of sexual safety (however you define that: condoms, PrEP, no fluid bonding, etc.) is crucial. I think you’ll have more success in drawing partner-gender boundaries, since coordinating is generally done before sex brain really sets in. This isn’t to say you shouldn’t set boundaries and your boyfriend shouldn’t follow them—I just think that particular one may be difficult to enforce.

To your STI concerns, yes, receptive partners typically are at higher risk, but you don’t have to bottom to be receptive. (If he’s giving head, he’s receptive, and if he’s like the vast majority of the population, he’s not using condoms when he does that.) Some STIs are highly contagious regardless of the position; I feel sometimes like a stiff breeze is all I need to contract gonorrhea. HPV is like glitter. I don’t mean to freak you out. I only want to point out that in light of this sea of threatening microbes we’ve found ourselves floating in, these positioning concerns often amount to splitting hairs. As to whether bottoming makes someone more vulnerable, it really depends on how you do it and whether you have predilections for vulnerability in the first place. Putting your dick in the mouth of a stranger who could bite it off without a hell of a lot of effort and of whose history you know nothing? Pretty damn vulnerable.

As for the rest, it’s going to play out the way it’s going to play out. In my own experience with open arrangements, another very effective guideline I have noticed is: “Don’t ask, don’t tell.”

Dear How to Do It,

I’m a 56-year-old woman. I’m straight but somewhat bi-curious. I’ve had a few boyfriends, but I’ve never had a serious and emotionally satisfying sexual or romantic relationship. That means I’m a virgin, among other things. I struggle with anxiety, depression, and low self-esteem. I have also lost or am not close with most of my family, and I have lymphoma—I was diagnosed six years ago, went through six months of chemo, and went into remission for four years before it recurred. (I currently have a “watch and wait” medical status.) Physically, I’m OK. Mentally, not so much. I cannot help thinking that each test or checkup could be the one that sends me back into chemo and upends my life once again. I’ve been in therapy for years, working on all of this and more.

Even though I do like a lot of things about being single and I know I can be happy without a partner, I have also longed to be in a relationship since I was 14. If you’re doing the math, that’s 42 years of longing! I’m not just longing for that mysterious thing called sex. I want someone to love, someone who loves me—and once I find them, I want to be able to enjoy having sex with that person. Now that I am in my late 50s, it seems that nearly everyone else my age has had at least one successful long-term relationship. About 99.9 percent of people I know who are my age or older are married. Or they are divorced, so they once were married. Meanwhile, I can’t seem to even attract potential dates. With the exception of the men I’ve met in church-sponsored singles groups, I guarantee that within five minutes of meeting me, a man will tell me he’s married, he has a girlfriend, or he’s gay. Whenever I get involved in non-singles activities (public speaking, community theater, book clubs, cancer support groups) or go to parties, everyone else my age is married or female. No, I am not interested in married men (not that they ever seem interested in me). Several times in my 20s and 30s, I suffered with having intense unrequited love for unavailable men. I do not ever want to have another terrible, awkward, and painful “crush” on someone who cannot or will not care for me. Also, I’ve also wondered if I might be bisexual. I feel more emotionally comfortable among women. At times I’ve felt sexual attractions to other women. For most of my life, I have wanted to be with men even while I was nervous and frustrated around men. Now, I just don’t know what or whom I want.


Dear Unrequited,

I was tempted to start my response by telling you I’m sorry that you’re struggling, but then I realized, more than that, I’m happy you’re surviving. You’ve been through so much and you keep going, putting yourself out there and attempting to connect with someone. That’s amazing. Keep it up. You didn’t mention online dating in your letter, so allow me to encourage you to cast a few virtual nets with some profiles. Sites like Elite Singles have special sections for 50-plus daters, and there are sites that wholly cater to that demographic, like Our Time. AARP has a subsite that provides tips and more resources for mature daters.

I felt a lot of compassion for you while reading your narrative, but I thought the last sentence of your letter was the most telling. Unfortunately for you, it signals work you must do alone. I can’t tell you what or whom you want, but I can advise you to figure it out and firm up your goals. Right now, it seems that you feel adrift and at the mercy of the universe. Even if you ultimately are—during my darkest moments, I’m sure that we all are—at least we can fool ourselves with the illusion of organization within the chaos by properly setting our sights. Failing to obtain the thing that you know you want may make disappointment sting harder than a perpetual, vague throb of dissatisfaction, but by now you have shown yourself you are more than equipped to move on. I’d rather have short blasts of intense pain than chronic aching, but maybe that’s just me. You put yourself out there, you might get hurt, but if you never put yourself out there, you might not feel much of anything. You’re tougher than you think. There are no easy choices, but time’s a-wasting, so decide.

The gay agenda tells me that I must encourage all questioning people to manifest their possible queerness, so by all means, go for a gal. I’m kidding, mostly, but why not explore that side of yourself? One positive thing about your bad luck is that it’s put you in the position of only standing to gain from further attempts at romance. In short, I don’t think there’s a panacea to be had here, especially since you already do so much to forge connections. I just want to encourage you to keep going and to invest in your great worth, which is apparent to me just from reading a few of your words.

Dear How to Do It,

Both my wife and I are on the autism spectrum (both high-functioning). With my increased stress levels and overall shutdown, withdrawal, and overwhelm issues, I just can’t face the signal-reading confusion and emotional demands of getting physically intimate. We both see psychologists and we’re seeing a counselor together, so I’m working on this. I’m interested, however, in whatever advice you’ve given to high-functioning ASD folks in the past and whether you know of any good resources for this situation. I’ve been looking all over the web for stuff to read that I can relate to, but I’m not having much luck. I should say, in my particular situation, my wife generally wants me to take the lead (which is tricky, given the intensive face-watching it requires on my part). She also experiences anxiety and sensory overload, which present similarly to vaginismus, so penetration in any position other than missionary with me on top is uncomfortable or painful for her. Unfortunately, given the rich fantasy life I’ve inhabited since I can recall, being put in charge of vanilla missionary is not enticing. That’s callous, but it’s also the calculus of my brain, unless we’re at full energy. What should I do?

—Mixed Signals

Dear Mixed Signals,

I’m happy to receive your letter and help bring attention to issues that neurotypical people may take for granted. But having no experience serving the ASD community in this capacity, I thought I should turn to someone who has: Michael Ian Rothenberg, who among his many titles is a psychotherapist and clinical sexologist who specializes in sexuality, relationships, and autism spectrum disorder. He told me via email that he comes across challenges like yours fairly often in his practice and acknowledged the lack of resources on the subject, given that many therapists aren’t fully versed in ASD issues, particularly sexual ones. He’s shared quite a few specific, practical techniques for you to try.

One suggestion Rothenberg has to help ease your burden is to create a window for sex to occur—he gave the example of Friday night through Sunday morning. “Having a time to initiate removes some of the guesswork that comes with reading facial cues,” he explained. “If your wife is not in the mood during the window, she’ll let you know.” For nonverbal communication, a specially designated scented candle your wife can light when she’s in the mood, Rothenberg added, may also help eliminate the question of whether or not to initiate. “When you smell the candle, it’s time to make your move,” he wrote.

To help foster sexual communication, Rothenberg suggests using what he calls the “ ‘yes’ method,” which he has found to work well with couples on the spectrum. “As you explore each other sexually, your partner only need say the word ‘Yes’ if they like what you’re doing or how it feels. That’s your cue to continue,” he explained. “If they say nothing, then stop and try something different until they say ‘yes.’ By only using this one word, it helps those who struggle to communicate and moves things along in a positive direction.”

Regarding the incongruousness of your fantasy life versus the vanilla missionary that your wife seems to require, Rothenberg recommends using your own words during sex to describe what you’re fantasizing about. He explained, “The language of sex can really be broken down into three categories: describing what you’re about to do sexually, what you’re currently doing sexually, or what you’ve done before sexually, i.e. ‘I’m going to lick your nipples.’ ‘I’m licking your nipples.’ ‘Remember when I licked your nipples?’ Your wife may, in time, also add these verbalizations to her sexual repertoire by repeating back what you’re saying, i.e. ‘You’re licking my nipples.’ ‘Are you going to lick my nipples again?’ People with ASD follow patterns of behavior and are resistant to change, but the good news is that once you create a new pattern of behavior, that becomes the new pattern of behavior. Though it’s not always easy, you can always add new sexual activities and behaviors into the mix.”

Finally, Rothenberg recommended discussing your anxiety, particularly that which is related to sex, with your therapist. “If your therapist does not specialize in this area, they should be able to refer you to a certified sex therapist who can help,” he said.

I hope you find something useful in this answer. It’s heartening that you are already working on this and I wish you luck in building a mutually satisfying sexual connection with your wife.

Dear How to Do It,

I’m a gay guy with a pretty hairy butt who tends to bottom. I’ve never shaved or waxed it, and I rarely trim my body hair, honestly—I like it, and the guys I see like it, so I don’t see a reason to. Recently, however, I got the first back wax of my life, and I kind of love the feeling of a guy on me without the hair. I’m more sensitive and I feel … transformed? Now I’m curious what would happen if I went a little further down on my next wax, but I have a much bigger mental block getting my butt waxed—I’m worried about inflammation (I’m sensitive down there), most of my partners love the hair, and I just have no idea if it’s worth exploring. Any words of wisdom?


Dear Rearscape,

These words are not particularly wise, but they are true: Hair grows back. Give it a go. I felt a sense of active discovery in your letter, as if your beliefs were transforming before both of our eyes, from sentence to sentence, so go forth and push away your butt hair like Alice parting overgrown Wonderland foliage to encounter bread and butterflies and oppressively mannered giant flowers and shit. There’s only one way to find out how many eccentric characters and puns you’ll fit down there.

Yes, inflammation is a potential hazard, and the preliminary bumps can turn to whiteheads, but in all likelihood that will calm down soon enough and you’ll have your sasquatch ass back in no time. What’s the worst thing that will happen? You’ll flare up so bad that your butt will be out of commission for a few days (or weeks)? Then you’ll have learned a valuable lesson, which is more than can be said about most of even truly enjoyable sexual encounters. Or, if you don’t feel like taking a boning breather, you might have to (gulp) top while you let the swelling go down? Give me a break, you’ll be fine. Variety is fun and can teach you new things about yourself, as your back wax has already shown you. Do you really want to get to your deathbed and wonder what turns your life would have taken if only you had let your butthole be bald that one time?


Advice From Dear Prudence

I love my girlfriend very much and at the age of 27 feel like I’m finally with somebody who I could spend my life with. I have been supportive of her naturalist attitude regarding hair removal and even find her hairy pits, legs, and other parts sexy. The trouble is that she also has scattered hairs growing across her chest and about a dozen long ones around each nipple. How can I explain to her that, although I support her natural ways and was well aware of her preference going into things, a little bit of removal would go a long way? It’s the nipple hair that really throws me. When I’ve brought it up she’s acted offended and explained to me that it’s natural for women to get hair all over. She says she could pluck them but they will just grow back. I’m really falling for this girl but am fearful that as we age it’s going to become more and more of a turn off until our sex life is dead.