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 have been married for over 28 years to my wife, and we have three children. Neither of us were that experienced sexually. We had sex prior to our marriage, and it was great at the time. She was the most wonderful, beautiful woman I ever met. Historically, our sex drives were not equal, but about eight years ago she began experiencing pain during intercourse. She went to see doctors, and I was patient and felt I supported her. She has not touched me in almost seven years. A little over two years ago, I had a conversation with her and asked if she wanted to stay married. She said yes and that she loved me, but she had no interest to ever have sex again with anyone. She even told me she could be asexual. I told her that sex was important to me and I was not willing to give up sex. She surprised me by saying, “I give you permission to see other women.” I said, “You do realize that I could fall in love with someone.” She said she understood, and she even repeated her permission to our therapist. She stopped attending counseling, and I joined Ashley Madison and Seeking.
I have met no one on Ashley Madison but have slept with numerous young women over the past two years that I have met on Seeking. Some experiences have been exciting and positive. Others not so much. I am proud of the fact that I was always faithful to my wife and did not sleep with another woman until I was given permission. While my wife has given me permission to sleep with other woman, she would be surprised at the number of women I have slept with and she would not approve of the money I have paid these young women. (We are wealthy, so I have not jeopardized our finances.) I have gotten to the point where I would like to have a sexual relationship without a financial transaction. Can you recommend any other websites? Can you also provide some long-term advice? Our kids are out of the house in two years. I will need to make a long-term decision on whether to stay married or move on.
—Looking for an Ethical Extramarital Relationship
You specifically mention young women in your letter, which leaves me wondering if you’re hoping for non-financially-transactional relationships specifically with women two or three decades younger than you are. If that’s the case, your options are likely to be slim, and those who are interested may objectify you based on age or expect a certain lifestyle, even if you aren’t directly giving them cash. Set your expectations accordingly to avoid disappointment.
Choosing a dating site is a balance between the crowd a site attracts and what’s popular in your area. I recommend setting up a few—OkCupid, Tinder, Bumble, Match—and seeing which ones have a lot of local users who you find attractive. You’ll want to be clear about what you can provide in terms of time and intimacy, and you should mention that you’re married with permission to be nonmonogamous. Whether you do that in your profile or in the first few messages is up to you. You also might consider meeting potential partners the old-fashioned way (presuming you’re vaccinated for COVID or have social opportunities that are outdoors).
As for your long-term decision, it’ll help if you can figure out what you want. Are you happy to stay married to your wife and have other (sexual) relationships that are limited in scope? Are there reasons to stay in your marriage other than stability for your children? Would you prefer to divorce, then date around with the goal of finding a second wife? If so, would you want to have more children? Do you want to spend some time as a bachelor? Think through different scenarios. It might help to make lists of potential pros and cons for each. And take your time—you’ve shared 28 years with your current partner, and that’s not something to toss away lightly.
Dear How to Do It,
I’m a cis female in a wonderful, loving relationship with my boyfriend of more than two years, and until him I had a lot of trouble having an orgasm during sex. We were able to figure that out fairly quickly, which is great, but now I’m running into a slightly different issue. I need external stimulation to get off, and I find that once I have an orgasm, I’m incredibly sensitive and need some time to recover. Not to mention the fact that when I do finish, it takes me a while to get back into things. I’m so envious of women who are able to have back-to-back orgasms, and I’m wondering if I just need a little more time in between than most? Are there other techniques or forms of stimulation I should try? Or should I just push through the slight discomfort after the first orgasm and see if we can make it to a second? For what it’s worth, I have the same problem when I masturbate. I recognize this is a pretty great problem to have, and I guess I’m just wondering if there are other options I haven’t thought of yet, or if I should learn to appreciate what I have.
Dear Too Greedy,
You might need time for your clitoral sensitivity to calm down before attempting to have a second orgasm or continuing with sexual activity that involves that area of your vulva. You might give your clit a break by stopping to get water or a snack or by focusing on giving your partner pleasure with other body parts like your mouth or hands. Or you might switch to stimulation of a different area—your whole body is a potential erogenous zone, and after an orgasm you might find yourself more sensitive everywhere. Try your ears, under your breasts, the back of your neck, the inside of your elbow, and anywhere else that you can reach. Post-orgasm could be a great time to explore your urethral sponge, taking the pressure, as it were, off of your clitoral glans. You also might find that you enjoy stimulation near your perineum, or on the lower portions of your inner and outer labia at this stage. And, hear me out, a light slap to your vulva might jolt you into a different experience of sensation.
I do think you should try pushing through your slight discomfort after your initial orgasm. If it becomes overwhelmingly uncomfortable or painful, stop. I encourage you to try this on your own and with your partner, as the experience of each can be different. You might enjoy pushing through, and you might not, but at least you will have given it a shot.
You absolutely should spend some time appreciating the body you have and the pleasure it brings you. Maybe this looks like you standing in front of the mirror noting parts you love. Maybe it’s making a list on paper. Whatever works for you, take five minutes every once in a while to focus on what you love about your physical self. And you’re definitely not being too greedy. You want to see what your body can do. You’re interested in pushing your limits to see what you’re capable of. I think that’s beautiful.
Dear How to Do It,
For most of high school, I assumed that my hormones were just on backorder and that I was a really late bloomer. However, I’m in college now, and I’m realizing that I’m probably asexual but heteroromantic. It was a relief when I first found out this was “a thing”—I always felt self-conscious because I never really got the appeal of sex, and I thought there was something wrong with me. However, I’m starting to realize how incredibly hard it’s going to be to date guys. I’m not sex-repulsed, just kind of meh on the topic. I could foresee myself maybe having sex with someone if I really liked them, but that wouldn’t be for a very long time. All of that goes to say that I’m not sure how to date or even if it’s morally OK for me to date. It doesn’t seem fair to deprive someone of sex just because I’m not into it, and it’s pretty hard to find other people who have no particular interest in sex but still want a relationship. The only solution I can think of is maybe nonmonogamy, but I don’t know how I’d feel about that in a long-term relationship. I would love to get married someday, but I can’t see how that’s possible without sex. Do I just have to suck it up and realize that I can’t always get what I want, that dating this way isn’t fair to others, and throw myself into fulfilling friendships instead of love? Or is there some way for me to move around this?
—I’m Overthinking This, Right?
Yes, you’re overthinking this. I’m guessing that you’ve been through a large process of life planning recently—what you want to study, informed by what direction you want your career to take—and I’m wondering if you’re feeling pressure to figure out the romantic aspect of your life in the grand sense, too. If that’s the case, you might consider giving yourself a break. You don’t have to have it all figured out right now. It seems like you’re currently borrowing a lot of frustration from your potential future self.
You’re correct that the majority of people are allosexual—meaning they regularly experience sexual attraction. So yes, you’ll encounter more people who are frequently aroused than those who rarely or never want sex. The thing is that most of us allosexuals have criteria—based on sexual orientation, faith or political beliefs, and aesthetic preferences—that drastically narrow the field of possible mates. And a person being allosexual doesn’t necessarily mean that sex, or frequent sex, is something they require. It isn’t so much that you can’t always get what you want, as it is that—like most people—you’ll have to spend significant time looking. You’ll also probably experience rejection, disappointment, and hurt along the way. It’s part of the process.
If you’re up front with potential romantic partners, it’s their choice to be with you or not. That’s not deprivation, that’s honoring their agency in deciding which kinds of relationships they want to participate in.
I encourage you to spend some time thinking about what you do want out of a romantic relationship. What is your idea of marriage, and why do you want that? Is there something about the idea of nonmonogamy in a long-term relationship that feels scary or otherwise unacceptable? And what does romance look like for you? Is it giving each other flowers? Netflix and actually chill? What makes those things different from friendship? These are all things worth contemplating, without needing to have any answers or decisions right now.
Dear How to Do It,
I’m recently divorced. After a year, I’ve met a really great guy who is sweet, caring, and feels like home. Our only issue is that he has a difficult time getting fully hard when we’re having sex. Yes, sometimes he’s been drinking, but his penis seems to react the same whether alcohol is a factor or not. When it happens, I usually say something along the lines of “Hey, it’s OK. We’ve got time. Let’s play some more.” However, I can see that he is really frustrated. Eventually he will get hard enough that he can come, but the buildup is intense, so he doesn’t last long. He has not been in a relationship recently. Since he is eventually able to come, I feel like it’s a mental block to the blood flow, but if it doesn’t resolve itself, I’d love for him to go to the doctor just to ensure nothing is physically wrong. When, and how, is the best time to have this conversation?
—Shouldn’t This Be Harder?
Before we dig in, I want to applaud your response to your sexual partner’s spongy state. You’re able to separate the turgidity of his penis from his interest in you, and your response is supportive. You might consider reminding him that penetration doesn’t have to happen at all, but you’re already doing great.
I’m not sure how your sexual partner’s ability to ejaculate implies a mental block, but I do think your instinct to encourage a visit to the doctor is sound. Pick your time wisely—well before any sexual advances begin and well after any sexual interaction. You’ll also want to choose a calm moment when both of you are sober, have plenty of time to talk, are well-rested, and have your other biological needs taken care of.
As for how to have the conversation, you’re the expert here. Will your partner respond well to a direct “I’d love for you to see a urologist to make sure everything physical is OK”? If so, dive right in. If he’s likely to be sensitive, you might want to warm up to it by starting with what you’ve said here about how wonderful he is and how much you value having him in your life, before gently letting him know that you’re somewhat concerned about his physical well-being and would like him to see a medical professional. Good luck.
More How to Do It
I’m a fairly inexperienced woman in her mid-20s. To keep it short, I have had a few partners, but until recently, the relationships I had weren’t very healthy and sex wasn’t especially pleasing to me. I figured that I might be asexual. Sex wasn’t great, it wasn’t terrible—I was basically just doing it to please my previous partners. I am now dating a person I have grown to really like. They have been wonderful in helping my own sexuality, so much so that I have discovered arousal, attraction, pleasure, and, for the first time, desire. (I now think I’m more demisexual as a result.) But I have now been confronted with some issues. First, how do I manage this whole attraction business? Now I want and think about sex with my partner a lot. I feel like I’m imposing myself on them and belittling them with my desires. Second, how do I find balance between sex and other stuff in our relationship? I’m scared our relationship is becoming mainly sexual. I don’t know how much sex is too much. How do I find out?