How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to firstname.lastname@example.org. Nothing’s too small (or big).
Dear How to Do It,
My wife of 35 years and I have widely divergent feelings about her premarital sexual history: I’m completely turned on by it and love hearing about her experiences, but she’s fairly tight-lipped about discussing them with me. She’s a lovely, elegant, and intelligent woman with a charmingly offbeat personality who graduated from a very well-regarded college and then from law school, so she dated a lot of men and had sex with maybe five or six of them—a few casual screws as well as a two-year-long engagement that she ultimately broke off. I, on the other hand, had a very limited sex life before I met her. She describes nearly all of her sexual encounters in pejorative terms: “indiscretions” or “slip-ups” or “lack of restraint.” All of her experiences were fully consensual with no hint of coercion. In fact, she seems to have initiated nearly all of them.
Apparently, I’m supposed to be jealous of or disgusted by the fact that she’s screwed/sucked off some guys before she married me. I never got that memo. I think (duh) she was free to do anything she wanted to do, so long as she had a willing partner. Here’s the heart of the matter: I love to hear down-and-dirty details about the sex she had with the other guys. Who had the biggest dick? Who went down on you? Where was the most exciting place you ever had sex? Did you swallow? Did you come? She usually deflects my questions or feigns lack of memory. But on the few occasions when she does tell me specifics, I get crazy hard and horny—like I’m 16 again, instead of almost 60. I’ve struggled with ED for several years and have overcome it with daily Viagra. But the erections I get when she “talks dirty to me” are grade-A hardwood. And I am ultra-appreciative toward her afterward.
I’m saddened that she feels too embarrassed about her prior antics to open up about them. Plainly, she has a fair amount of emotional baggage about her past sexual behavior—but that was 35 years ago! And ideas about how to put her at ease with herself?
Dear All Ears,
I think you might be using the language and concepts of social justice, specifically pro-sex feminism, to justify your desire to get your rocks off imagining your wife with other men. Plenty of people like hearing details from their partner’s sexual past—or present, for that matter. Consent still applies, and active consent is still the goal. If your wife doesn’t want to talk about it, you’re wrong to beg, demand, or otherwise coerce her into changing her mind.
People get to regret sexual interactions they’ve had, even when those interactions were consensual and pleasant. Even if they’re sex-positive. People should get to have privacy around any subject they don’t want to talk about. Even with their spouse. Even if it makes their spouse’s dick hard. And really, it’s simply unreasonable to expect your wife to recall details of sexual experiences from more than three decades ago. Would you ask her to recall the specifics of a lunch she had in 1984? Is my false equivalency any less reasonable than your request that she rank dicks she encountered individually over a span of some years?
If you can’t let this desire go, consider a cam girl who can recount sexual adventures, or read real-life erotic stories—whatever’s within the bounds of your marriage. Leave your wife out of it.
Dear How to Do It,
I am a mid-20s gay man in a serious relationship with an older man, which started as just the usual casual sex buddies. Working in porn, he occasionally reluctantly bottoms for a shoot, but he’s said many times that bottoming for him is deeply intimate and enjoyable only when he’s head-over-heels in love. Around six months ago, not long after we both realized our romantic interest, he was given a double helping of sexual trauma when he was drugged and violently raped by what was supposed to be a hookup, which triggered deeply buried memories of child sexual abuse. I expressed my willingness to pump the brakes or even swear off sex while he mentally recovers, but our sex life never faltered (following his lead) and still continues to be great (which may be because he exclusively tops me and never vice versa).
Nearly half a year later, he’s been talking much more about me topping him, and I’m more than interested in diving in, but every time we try he clenches up, no matter how slowly, gently, and free from pressure I try to be (and I’m talking about 10 minutes of deep, romantic kisses and ass-eating and other such foreplay). It’s difficult because he usually tells me to keep going, even though he clearly struggles with it. I shift into aftercare mode and always eventually call off him bottoming for the night and substitute with lots of cuddling, kisses, and massages. I have no idea how to approach this. I’m more than happy with anything we do in the sack (whether that’s penetrative or not), but he’s been pretty clear in that he wants me to top him till we both come. It’s a bit difficult staying hard when I’m worried I’m hurting him, and I don’t want to accidentally push him too far by unintentionally pressuring him, and stopping every minute to make sure he can relax and reassure him that I love him even if we stop isn’t exactly sexy. How do I simultaneously balance keeping the mood right, taking care of his limits, and fulfilling his sexual desires?
Dear Tense Top,
I think you and your partner ought to have a purposefully not-sexy conversation about pain and his emotional state. No kissing beforehand, overhead lights on, sober, and clothed. Ask your partner how connected he currently is to his body. Ask him what his ass feels like when it clenches up. Find out whether it feels more like good pain or bad pain. Discuss a safe word, and how to address discomfort or a need to slow down but not stop. Talk about why he’s pushing himself like this. Share your own comfort zone and qualms—you get to have your own boundaries and limits, too. If you aren’t comfortable because you’re worried, that is completely valid and needs to be addressed. You don’t mention therapy in your letter, but also make sure he is getting the help he needs to process his trauma outside of his romantic life with you.
On the physical side, I want to confirm a few things about this “other such” foreplay. Ass-eating is great and all, but you need to warm up the sphincters, and not many people can reach the inner sphincter with their tongue. Are you easing your fingers in slowly and leaving time without friction for your partner’s involuntary muscles to adjust to what’s happening? If you are and it still isn’t working, you might need to leave more time or invest in an anal training kit. Even the smallest phallic dildo—smaller than a finger—can be useful because finger bones can feel harder and more uncomfortable than the softer material of a purpose-designed sex toy. Penises can be too large at first.
You might find you need to walk it back even further. Have your partner explore his ass with plugs of various sizes. He’ll be better able to make small adjustments and feel out what the edges of his physical comfort zone are if he’s leading the expedition. Topping can have a couple of different meanings. If there’s any power dynamic to your interactions, you might incorporate it into these prep sessions by taking a role of authority and telling him what to do through the process. You can also use that power to insist on longer warmup times in a way that incorporates them into your play. As in, “I’m not going to give you my dick until that ass is wide open.” He can also be the active partner while you penetrate him, if it’s easier.
Communication will be essential here. Some parts of sex aren’t very sexy, but we do them anyway because they’re necessary. Discussing condom materials and latex sensitivities isn’t usually a boner-springer. Reciting test dates and results doesn’t tend to rev people’s engines. We still talk about these things, though, because they’re a part of safer sex. So even if you can’t find a way to make these necessary parts inherently erotic, I hope you’re still prioritizing them. Safer sex in my definition encompasses STI prevention, sure, but also prevention of mechanical injury and emotional damage. He’s only got one asshole, and you’ve only got one heart.
Dear How to Do It,
I recently ended my relationship with my girlfriend of five years. We live together—we bought an apartment, and we were planning to have kids in the following years. During the last two years of the relationship, sex was scarce, and she told me she was not very interested in it anymore. At the beginning, I tried to motivate her, we tried several games and toys, and in the end, I just gave up. I thought we were happy nonetheless.
About a year ago, after noticing the books she was reading and the Recently Watched on Netflix, I asked her if she was interested in an open relationship. She told me she was, but that she didn’t dare ask because I didn’t seem like the kind of guy who would be interested in that. The thing is, I was. I told her I would be open to anything as long as there was communication.
Well, a month ago she decided to break up with me. Turns out she’s been going out with different people during the last year. She never told me, she lied about who she was with and where, and the worst of all: She does enjoy sex, just not with me. We have been living together for a month since our separation because neither of us have anywhere else to go. I have to see her leave every morning wearing my favorite dresses and perfume and come back the next day wearing the same clothes. I find her boxes of condoms laying around the house, and my favorite underwear with our dirty clothes.
I know it is not my fault, but it is so hard to know I was the only one making efforts for so long to feel so rejected and betrayed. I’m a good person, a good professional with a good job, and I think I was a good, loving partner. But now I feel worthless. I find it really hard to leave bed in the mornings, and I lost all motivation and plans I had. I don’t know how to deal with this anymore.
Dear House Arrest,
Get out of that apartment as soon as possible. Save up and move to a small studio. Crash on a friend’s couch. Can your family take you in? Just get yourself to a place where you can really rest and start recovering so you can think rationally about the process of separating when real estate is involved. In the meantime, separate your laundry and stop looking in what will be her hamper. Do whatever you can to ignore her on her way in or out of the apartment.
The next step is to start seeing a therapist. You’re defending your goodness and describing feelings of worthlessness. I’m concerned that you might have tied your worth to your partner. It’s particularly concerning that you might have tied your worth to a partner who went behind your back after you’d given permission as long as there was communication. That’s a real, painful betrayal. Talk it out with a professional. In the meantime, lean on your friends.
Table sex for a while. Get yourself back to a place where you feel ready to connect and be fully present, if only for a brief encounter. Do it sober when you’re ready to put yourself out there again.
Dear How to Do It,
I’m a woman in my early 30s. I’ve always been terrified of online dating because I’m heavy and have self-confidence issues, but my problem is that I find a lot of sex boring; I like it rough with an element of domination (by him). I’ve never had a full-on domination relationship, so I don’t know if that’s what I want, but I do know that I find gentle sex—and even a guy going down on me—unappealing most of the time. I like being left with visible bruises and bite marks (I bruise easily).
I currently live in a small town where everyone knows everyone and options are fairly limited, but I’ll be moving back to a big city in not too long. My question is: How do I find men who are interested in what I’m interested in? I’m not necessarily looking for a boyfriend. I’m fine with sex-only relationships, but I want them to work for me. If I do get myself to a place where I can go online, how do I communicate what I want so I don’t waste both of our time without letting too many people know? I’m looking for advice both here and for when I move back.
Dear Dom Spot,
OkCupid has plenty of profiles with blurred, cropped, or otherwise obscured faces. People also have kink-specific profiles on that site. You might also want to check out FetLife, which is kink-specific. You might be able to find people who live one or two towns over, and who are likely to be as motivated as you are to maintain discretion. People tend to mention at least a sketch of what they’re into (top/dom, bottom/sub, pain, power exchange, leather, latex, feet) in their profile, and you can let them know your interests upfront or at whatever point in the conversation you feel comfortable doing so.
When you move back to a more urban environment, you can attend munches, sex-focused workshops, lectures, and parties to meet people in a more organic environment than apps can provide.
For both small town and big city, it’ll be helpful to articulate your desires and boundaries to yourself in a word document. Think about what you know you do and don’t like. Consider what directions your fantasies take and what of that you think you’d like to explore further. Feel free to read erotic novels and watch BDSM-themed porn for ideas and to imagine yourself in the shoes of the subjects. Then edit it all down into succinct statements. Get ready to communicate with as much and as little detail as you want in various contexts. If you’re shy, you might practice saying things out loud, first to an empty room and then to a mirror.
More How to Do It
I live with my partner of 10 years in a happy, committed relationship. My partner is a fantastic person and very considerate and giving in bed. So what’s the problem? I desperately want to have sex with other people. Every time we have sex or I masturbate, I think only of other people.
Everywhere I go I get crushes: subway passengers, my bank teller, co-workers, the gamut. I can’t imagine a better partner in life for myself and I really don’t want to break up over this, but I also know that suggesting we open up the relationship would be devastating. I should have known this was going to be a problem before, because even in the beginning it wasn’t his physical appearance that attracted me to him, but we fell in love anyway and have now built a life together. How do I manage this? It’s not going away, and it feels like I’m cheating.