How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to email@example.com. Nothing’s too small (or big).
Dear How to Do It,
I’m a man in my late 30s. My wife and I have three young children and a satisfying sex life. We have a closed relationship and, although I fantasize about other women and watch porn, I don’t want to hook up with anyone else.
Also, I love dancing. I like to dance at home alone or with my kids, with my wife at a party, and (very occasionally) out with friends at a bar or club. I’m conventionally handsome and a better dancer than people expect, and I sometimes end up dancing with strangers when I’m out, especially when it starts getting late. I’m generally open to dancing platonically with anyone who has a nice vibe, but if I’m attracted to a dance partner and they’re signaling that they’re into it, I’ll dance … non-platonically. It’s a thrill to find a rhythm with someone new, indulge the sexy stranger fantasy for a few songs, and get the ego boost that comes from feeling desired. Dance floor shenanigans are within the bounds that my wife and I are comfortable with, but kissing other people is not.
This past weekend I was dancing non-platonically with a woman who whisper-shouted into my ear, “When are you going to kiss me?” I told her that I was married; she understood the implication and walked away, but found me later in the night to calmly tell me, “What you did wasn’t nice.” I understand why she might have felt annoyed or felt misled into giving her implicit consent to dance close, but I can’t tell whether what I did—lead her on, I guess?—was wrong or otherwise not nice. I always wear my wedding ring and never lie about my marital or parental status, but the music was loud, we weren’t chatting, and the topic hadn’t come up. Also, this dance partner approached me.
So, my questions: What obligation did I have to proactively clarify my limits when I knew she might assume that I was open to more than a little bump and grind? If there was an obligation to communicate, at what point should I have done so? Would the timing of the obligation have changed based on where my limits were? For instance, if my wife and I agreed that we could kiss but not have sex with other people, would I have been in the wrong if I kissed without first sharing that I’m married and that a dance-floor smooch was all I was down for? Coming back to the facts at hand: I suppose I could flash my wedding band to everyone I dance with, but I really don’t want to. It feels presumptuous (maybe they’re also just looking to dance) and buzzkill-y and, more selfishly, would presumably hurt my chances to have the up-late-sweaty-dirty-dancing-fantasy fun I enjoy on my occasional nights out.
Dear Specious Swayze,
I do love a good chance to make sweeping generalizations and unilateral decisions.
We had a letter a few weeks ago from a woman who felt misled by a hookup with a nonmonogamous man. Reading it might illuminate how the woman you were dancing with might have felt, even though the details are a bit different and the stakes here are lower.
The woman you were dancing with didn’t ask you if you were single, and you didn’t tell her. She assumed you were available for more than dancing, and you assumed she’d be comfortable dancing with a married man. Neither is correct. Monogamy is still by far the default relationship style, so assumptions about your availability are going to happen, and people may be hurt in the process.
You might consider attending swingers’ parties early for dancing and leaving as things start to steam up. You’d be dealing with another set of assumptions—that you and/or your wife are available for sex—but you’d be in an environment where everyone assumes there are intricate boundaries to navigate and more likely to talk through things first. You also might, yes, draw attention to your wedding band. We’ve been using them to communicate marriage status for a long time. Aside from symbolizing the eternity of love, they’re really good at telegraphing “I’m married!”
All of that said, there aren’t really any clear rules about what’s OK to do and who is OK to flirt with while you’re married, so you’re going to have to judge the risks of being “not nice” or actually hurting someone versus the pleasure of interaction on the dance floor. You very well may upset someone again in the future, and if you can live with that, so be it.
Dear How to Do It,
I am an 80-year-old widower who craves some sexual interaction. I live alone in a mid-size Midwestern city and check the local online “escort” listings, where is a wide range of prices and descriptions of services offered. I’ve hesitated making contact because of worries about robbery, extortion, STDs, and bait-and-switches, not to mention arrest. I know enough not to provide a credit card number, but do you have any other advice or tips on how to navigate this world?
The first thing I have to address is the legality of what you’re suggesting. There are laws like FOSTA/SESTA that criminalize the promotion of prostitution, among many others. The only direct American providers I can encourage you to visit are in parts of Nevada—which runs on a brothel system—or overseas in countries where the laws are different.
Beyond that, I reached out to Charlotte Shane, former sex worker and author of Prostitute Laundry, for insight into the vetting process. Here’s what she had to say:
I would suggest an attitude readjustment to start. Sex workers are at far greater risk of robbery, rape, violence, and arrest than are their clients, and if you’re going to be too paranoid to be respectful and kind to whoever you contact, I think you should stay home. But if you decide taking a chance is worth it, a little common sense goes a long way. If you show up to an appointment and the person who greets you doesn’t look like their pictures, you should leave.
If you’re exchanging fluids, condoms and dental dams can be used (and the person you’re paying will almost certainly insist that they are). You may want to mention while booking the appointment that this is your first time and you are nervous, without going into details about why: If the provider’s willing to help you feel more comfortable, it’s a good sign of compatibility. As with any service, there are no guarantees you’ll get exactly what you want, but if you can leaven your anxiety with positive anticipation and an intention to treat your escort well, you might be pleased with what you find.
Me again. To reiterate: The theory behind decriminalization is that illegality increases potential harm for the provider and the client. My advice is to keep your activities legal.
Dear How to Do It,
My girlfriend and I are in our early 20s. We both currently ID as cisgender lesbians. We’ve been serious for about six months now, are in love, and have a pretty good sex life. But we do have some breakdowns in communication, especially when it comes to sex.
One of the things that’s been eating at me the most is this: I am generally a Boob Gal, but I know she has hangups about her chest. I think her chest is hot and told her this before I realized this was a sore spot. She identifies as butch, has expressed an interest in chest-binding, and told me that she’s very self-conscious about her boobs, which are on the larger side of average, in part because of how men have objectified them in the past. When I try to talk to her about this, or offered to help her look into binders, she has said it makes her feel weird, and she doesn’t want to discuss it. So I’ve dropped it, and tried to stop making comments or touching her chest when we cuddle.
When it comes to sex, though, I’m not sure what to do. Nipple play has always been part of our encounters, and I know that she enjoys it, but only past a certain threshold of arousal. She never explicitly states that she doesn’t want me to touch her there, but if I do it at too low a state of arousal, I can tell that she doesn’t enjoy it, and I awkwardly stop after a few seconds. She knows about my own boobpreciation, so whatever I do—touch, don’t touch—is conspicuous. All this feels like it could lead to bigger issues in the long run. I’m especially worried that this is one instance of her experiencing gender dysphoria, and I don’t want her to think she can’t be open with me just because she knows I like boobs.
I don’t want to force her into a conversation that I know she doesn’t want to have, or presume to know what she does or doesn’t want in bed. But I also don’t want to make her uncomfortable during sex, especially as we’re supposed to be learning more about what works for each other. She goes to therapy for a variety of reasons, but her sessions are extremely limited, and I’m not sure I feel comfortable asking her to bring up things I think are important in that time. What’s my best course of action here?
—Conflicted Boob Gal
Dear Conflicted Boob Gal,
I think you should try again and directly ask your partner if you can have a serious conversation about nipples and breasts. Pick a good time—low-stress, no pressing appointments, everyone sober—and start with something like: “I know this is a difficult topic, but I want to know where your boundaries are around your breasts and nipples so I can carefully respect them, and I’m feeling like I need guidance here. Are you comfortable talking about this with me?”
Be prepared for her to say no, or attempt to have the conversation and find it difficult. Of course, it is also possible that she’ll be able to calmly fill you in on her thoughts and inner world. Brace for all possible outcomes.
I know these conversations can be scary, but I don’t see another course here. You will almost certainly make mistakes, and you’ll probably learn from them. You’ll probably learn how to be a better partner to your current love, and you may learn how to be a better partner in general if you go on to date other people.
Your partner may very well be experiencing gender dysphoria, or she might simply find stimulation unpleasant until she’s at a certain level of arousal. Maybe both. You won’t know until you talk about it. I do think you’re within your rights to inquire whether your girlfriend has broached the subject of her breasts with her therapist, but leave it as a simple question and back off immediately if she’s uncomfortable discussing her therapy sessions. Good luck.
Dear How to Do It,
I am a 60-year-old woman, and I never had an orgasm with another person, male or female, in my whole life. I could with a strong vibrator in private, so I don’t think there was a physical problem. For the last 20 years, I have been on a variety of strong antidepressants, so I know that can really make it difficult to have an orgasm, but my problem is some kind of mental issue, I think. Sex and being naked are very embarrassing to me: I always had to be drunk and in the dark to do it. Been too embarrassed to talk to my psychiatrist about it. Besides fear of looking or acting stupid, I think there may be a fear of loss of control. It’s like I think if someone makes me have an orgasm then they will think they have power over me or something? By now, I’m used to not having sex anymore, but I sure would like to know before I die why I wasn’t able to relax and enjoy it like everybody else. Any theories?
Dear Last Call,
Fear of loss of control during orgasm is so very real. You are far from the only woman to report this. I’ve experienced it myself during hookups where red flags pop up—wondering if it’s safe to let an orgasm wash over me and be incredibly vulnerable in that moment. And some partners do act as though expediting an orgasm for their partner gives them some power, control, or the right to an orgasm themselves.
Mid-orgasm expressions aren’t particularly glamorous. You might check out a project like Beautiful Agony (NSFW) for examples of just how silly we all look when we’re scrunching our faces in the throes of pleasure. There’s a different kind of beauty in that, but it may take some getting used to—an acquired taste, if you will.
I want to spend some time on the idea of “relax and enjoy it like everybody else.” You can read through the archives here at How to Do It, or really any advice column, and find examples of other people who struggle to relax and enjoy sex. Sometimes it’s internalized shame from a religious upbringing. Sometimes it’s internalized slut-shaming. Regardless of the whys, you are not alone.
If you want to attempt partnered sex again, I suggest you start slowly. Spend time alone, nude, in the dark. When that feels OK, turn the lights on and look at yourself in the mirror. Imagine another person in the room with you. Listen for worries and qualms. Unpack them, and see what you can work through.
You also might try writing about your fears with pen and paper. You can immediately shred or burn the pages, or consider bringing them to your psychiatrist as a way of broaching the subject without having the discomfort of speaking out loud about it in their office.
More Advice From Slate
My 14-year-old son recently came across some Polaroid pictures of me that his father took of me back when we were 14—we have been together for a long time and got married when I was pregnant with my son. The problem is that the pictures are nude shots! You can’t really tell that the pictures are of me, as my appearance has changed pretty dramatically since I was 14—hair color change, weight difference, boobs, etc. My son came to me really worried with the concern that his father was potentially hoarding teenage porn. I didn’t directly tell him that the pictures were of me, but assured him that his father didn’t look at or keep teenage porn and that I would speak to him about it. But should I be more direct? Which is worse, thinking your father has kiddie porn or knowing that you just saw a 14-year-old version of your mother naked?