Photo illustration by Slate. Photos by Getty Images Plus.
How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to howtodoit@slate.com. Nothing’s too small (or big).
Dear How to Do It,
I am a 43-year-old man, and my wife is 41. We married when I was 31 and my wife was 29. She never had sex before we got together, not even masturbation, because of her conservative upbringing. On my part, I started masturbation in seventh grade, and I first had sex while I was 16. We enjoyed ourselves the first few years. After that, she seemed to lose interest. I think she had a few real orgasms, but mainly faked them.
Now, I always suspected this was because I am not very big—I’m about 3.5 inches erect, and I tend to ejaculate quickly. I told her about bigger men, since she really had no idea, and said she could try another man, since I had 13 to 15 sex partners before we were married and she had none. I wavered on this a few times as I got insecure and jealous, but in one of my more permissive times, she met a man and liked him. I tried to call it off, but she wants to go forward. Should I let this happen? I’m afraid he will be much bigger and she’ll enjoy him better, and I don’t want to lose her, as I love her. She says she will keep him on the side just for the physical thing. And she will not leave our kids and me, as that guy also has kids and a wife. I’m not sure what to do.
—Outsize
Dear Outsize,
An open relationship can be a perpetual process of trial and error.
I sympathize with both sides here. You introduced the idea of your wife sleeping with someone else, she liked it, and now she wants to make it real. It’s pretty hard to delete someone’s desire, and it’s borderline shitty to try to do that to desire you helped cultivate. Don’t dangle carrots at your wife; she’s not a rabbit. Consistency is very useful in relationships, which necessarily involve synchronizing two or more lives that wouldn’t necessarily tend toward the same path when left to their own devices.
But you are allowed to change your mind. An open relationship is a large concept that isn’t always immediately graspable; it can be a perpetual process of trial and error. It’s not a good sign if you have misgivings about your wife sleeping with another man before it’s even happened. If it’s vexing you in the abstract, it may positively haunt you if it actually happens. As it stands, I do not think it’s a good idea for her to go through with this at this immediate moment, but I also think that you need to pick a side—if you keep flip-flopping about something so important, your wife could feel like you are messing with her head, and that’s not going to be good for your relationship either.
If you do go ahead, rest assured that the other guy may be bigger and that she may even enjoy him better, but that doesn’t mean she will leave you. Plenty of people find it easy to keep sex buddies without love entering the picture and interfering with their primary relationship. It’s awfully self-assured of a woman who has thus far had sex with one person, the literal love of her life, to assume that is exactly how things will play out, but I admire the chutzpah. You definitely need to talk about this more and figure out a way for you to both be satisfied—would you be amenable to a three-way or some other scenario in which you are present for her extracurricular banging?—but even the worst-case scenario could turn out to be not so bad for your relationship.
Dear How to Do It,
I’m the stepmom to a sweet 15-year-old boy who is with us full time. (His mother lives abroad but does visit often.) He’s a good-looking kid and has had “girlfriends” for a few years now, but the relationships seemed innocent to me. My husband did have a basic sex talk with him, and he confided that he is still a virgin. Yesterday, I came home early because of a work holiday, and he was in his bedroom with a soccer teammate, with the door ajar. I can’t be certain of what I saw, but it looked to me like they were watching pornography on their computer, and I think they may have been masturbating. I’m not sure, because they clearly hadn’t heard me come in, and I immediately went back out. From searching online, it seems this isn’t very uncommon at his age and doesn’t necessarily imply anything about his sexuality. (I think that would be difficult for his father, but of course we’d support him either way.) But we are definitely not OK with him having sexual interactions with other teenagers in our home. I’m struggling with what do to now. Do I tell his father about this? He would definitely take the lead on a conversation like this normally. And if not, do I mention it to my stepson? Or do I just let this go, especially since I am not certain what I saw?
—Helping Hand
Dear Helping Hand,
Try your best to avoid being a cop in all situations, but specifically here, because you don’t really have much standing. You shouldn’t say anything because you don’t know what you saw. At the very most, you could ask your stepson if you saw what you saw; brace yourself for a denial, an immediate end to the conversation, and regret on your part that you brought it up in the first place. “Yes, my buddy and I were totally jerking off to porn together—what a weight off my shoulders, thank you for asking,” said no 15-year-old ever.
Let’s briefly consider what the proper course of action would be if you were certain that you saw this kid masturbating with his friend. I know the party line is that teenagers should not be sexually active, chiefly because they are irresponsible and ill-equipped to deal with consequences like STIs and pregnancy. All that matters precisely not at all to the majority of teens, at least in the U.S.—the CDC estimates that about 55 percent of people have intercourse by age 18. Teenage sex is an inevitability akin to the weather; hormones rage like storms. I know it’s parents’ jobs to promote ideals that their kids might fall short of, but being so hard-line about sexual contact is an exercise in futility and a recipe for resentment. Even worse, it approaches something like sex negativity and helps cultivate shame. I say this as someone who doesn’t have kids, doesn’t want kids, and is thrilled to never have to deal with these issues in my own life, just in hypotheses based on the lives of strangers. I can almost empathize about the general discomfort of being a caretaker of a young masturbator; I had a cat that was supposedly neutered but humped my fleece blankets all the time. I did not want him doing that, not in my house! We existed at odds for this and several other reasons until his untimely death at age 3½.
On another note, yes, plenty of self-identified straight guys have jerked off with pals, but there is a chance this kid might be some kind of queer, and I’m not particularly confident that you and your husband are equipped to handle that. It’s in your husband’s best interest to get over or at the very least not display how “hard” it would be to learn that his son is who he is. Support with caveats and drama often doesn’t read like support at all.
It’s your house. If you absolutely cannot contain yourself and simply must broach this subject with your stepson, I would recommend dissuading him from jerking off with his friend again in your house in the most gentle way possible. Maybe it’s just “no friends over when we’re not home,” and doors open. But think hard before doing so. Remember that this particular method of exploration will almost certainly not lead to him being infected with anything or able to apply for a spot on 16 and Pregnant. There’s a bright side or two to look on here.
Dear How to Do it,
My husband of 15-plus years told me about his cuck/hot-wife fantasy a few years ago. I was into it. Our sex life has always been great and full of experimentation. So after we talked about it a lot, I started flirting around on some apps. (I of course was always upfront about being married.) I almost went on an IRL date, but canceled just prior when my potential date revealed he’d voted for Trump and I just couldn’t deal with that. My husband was super turned on this whole time whenever I was messaging with men, telling him about our conversations, etc. Things went on this way for a while, and I found that while I really enjoyed getting attention online—it helped with my self-confidence—I was sure that actually having sex with anyone other than my husband wasn’t going to happen. I spoke with him about this. I told him I felt I would never actually fulfill this fantasy for him because I just don’t see me having casual sex. He was fine with keeping this a fantasy and with me just playing online.
I continued to drop in and out of apps for some time and then I met H. I instantly clicked with him. He was just so many of the same things that made me fall for my husband, and I so enjoyed talking to him. I was excited to tell my husband I’d met someone I really like. But he reacted differently than he ever had. He tried to seem happy about it at first, but it was often clear he was not into it this time. I was a little bummed that it didn’t seem to rev him up like before. I was also a little offended because it used to be about him being turned on by me dating, but now he says he wanted me to get to sleep around casually because I never had the chance when I was younger. But I don’t think of this as something that needs to somehow be rectified.
After H and I had been talking for a few months and were planning to meet IRL, my husband told me it “felt separate” this time. And that he was feeling insecure because his sister’s marriage was falling apart. I of course understood and said I would stop talking to H. The decision felt so simple at the time. But now, I really miss him. And I feel it’s unfair. I thought I followed the rules. Then as soon as I fid someone, he cancels everything? At the same time, I am truly and deeply in love with my husband. I will always choose him and put him first and I never want to hurt him.
H and I have texted a couple of times in the months since. Which I know is wrong and I do feel guilty about it. I tell myself it’s not as bad because we are not flirting at all, but I know I still shouldn’t be talking to him. He is respectful of my boundaries and, like me, would be fine with just being friends and never meeting. We just really do help each other, and it’s so hard to lose someone who lifts you up. Am I wrong to feel that my husband’s flip-flop on me dating as soon as I meet someone I like is unfair? Can I approach him with my desire to maintain a friendship with H? Or would that risk hurting him too much?
—Sidepiece
Dear Sidepiece,
The difference between H and the other guys you talked to is so obvious. Look at how you’re pining for him and none of the other strangers. Your husband clearly knows you well and picked up on H’s exceptionalism—you really liked him partly because he exhibited traits that made you fall for your husband. Of course that made your husband insecure. With a new potential partner, you were able to relive an important part of your life previously shared with your husband.
It seems to me that your husband’s flip-flop occurred as a result of your connection with H and is not necessarily a complete rebuke of the cuck fantasy you’d discussed. He may very well be fine with you looking around and even dating as long as you don’t really like the guys you’re doing it with. It’s a line many people in open arrangements draw. You could reasonably argue that’s unfair. After all, you can’t predict your feelings when exploring unknown realms. But one of a partner’s jobs is to step in when you start to go overboard. It seems like your husband essentially vetoed H. Not everyone in nonmonogamous relationships believes in vetoes; some feel one’s primary partner has no right to make any impositions and that you are with that person not because of rules but because you want to be there. I do happen to believe in vetoes. They help people feel secure, honoring your partner’s fears and needs shows respect, and the point of setting and upholding vetoes is to exercise the intricate communication that harmonious open arrangements require. All of this makes sense to me.
I hear you when you say you think your husband is being unfair by changing his mind, but that’s just something people do. You’re one of those people! Notice how you say that you would never want to hurt your husband but then reveal in the very next sentence that you’re still talking with H after you told your husband that you would stop. It only took a line break for your own mind to swerve.
You can push back on principle, but the reality is your husband doesn’t want you seeing this guy. I think you need to reevaluate what you want from your dating. It seems like your husband is cheering on sex, while what you’re interested in is more along the lines of relationships. He’s taking a swinger approach; you’re viewing this through a more poly kind of lens. If the objectives aren’t aligned, this will only be a frustrating, if not devastating, process for both of you.
If you want to stay in good standing with the man you claim to be madly in love with, drop the pen pal you’ve “known” for a few months. I’m sorry. You like him, and liking people is fun, but it’s just too risky, and you already gave your word. Be the consistency you want to see in your relationship. Moving forward, cruise for dudes alongside your husband. But do keep avoiding Trump supporters. That’s one thing you’re doing right.
Dear How to Do It,
I’m a gay man in my early 30s who lives in a city that’s big enough to contain what feels like an endless supply of potential sex partners. I don’t have as exciting of a sex life as my orgy-frequenting friends, but I am generally up for a good time and oftentimes find myself having one, if you know what I mean, with one-time randoms and regulars alike. I’m mostly having fun and staying safe—I’ve had one STD in the past three years. There’s a thing some guys do, I’ve noticed, that has been bothering me and I’m wondering if you could help shed light on why they do this or whether I should put up with it without complaint. The thing they do goes like this: After we meet and have a hookup that from what I can tell is mutually satisfying, they go cold. I’m not trying to marry any of these men, but I can barely get more than a word back in response when I send a follow-up text. I’ll sometimes see them out soon after hooking up, and it’s like they’re looking past me. But then I’ll run into them a few months later, well after I’ve given up ever thinking we’ll ever get naked together again, and they’ll be all over me. Totally into it. What’s up with this, and am I a chump if I sleep with them again after they ignored me and made me feel kind of bad about myself in the process?
—Iced Out
Dear Iced Out,
Ah, you’ve touched on a phenomenon I have observed firsthand quite a few times: the long lap. I haven’t quite figured out why some guys boomerang so slowly, but it probably has something to do with the hunting mindset against the backdrop of a city teeming with prey that will arrive at your door already on its back, legs up in the air. People are busy! I think that some guys are motivated by quantity, so much so that it becomes their quality. If they never swung back around for more sex, you could chalk up their apparent disinterest to several factors: no detected match, their own issues with sex and/or commitment, your smell, their experience diverging considerably from the mutually pleasurable sex you thought you were having, etc. There are so many (valid, albeit not necessarily nice to hear) reasons that someone may not want to have sex with another person again, and when a lot of sex is being had, a lot of those reasons will manifest.
But when they do show up again, enthusiastically, I think it mostly shows that a lot of guys don’t know what they want. In New York, people say everyone’s always looking for the next best thing. If you don’t immediately check all their boxes while making them come hard and then serving eggs à la française the next morning, well, maybe the guy standing next to you at the bar will. Worth a try, at any rate. I think, too, that when people are having as much sex as the men who have sex with men in urban areas can have access to, there inevitably forms a large gradient of connection levels. There are one-timers, regulars, semiregulars, every-six-monthers, etc. It could be nothing but coincidence that you happen to find yourself connecting with guys who are only willing to keep connecting sporadically. Or maybe it means that for whatever reason, these connections that you’re making are relatively weak. A huge factor here is that this kind of sex-frequent lifestyle, while it necessarily involves contact with (many) others, nonetheless fosters greed that makes some people act like selfish pricks without consideration for those who are making their active sex lives possible.
Regardless, the indifference you detect is not that big of a deal, and I hope you can find a way to chalk up to it being a product of the other guys’ issues, not a reflection of your worth. You say you have an endless supply of sex partners at your disposal, so don’t worry about the ones you don’t hit it off with or otherwise make you feel shunned. Focus on the guys who make you feel good. But also, don’t feel bad if a long-lapper comes back around and you give in to weakness. Turning down good sex with a hot guy on principle, because he’s somewhat distant—that would be the chump move.
—Rich
I’m a woman in my early 30s. I sometimes enjoy not wearing a bra in public. I like the possibility of somebody seeing my nipples through my shirt. Recently, on a solo road trip, I had the desire to pull my shirt up and expose my breasts while driving on the highway. I liked that somebody might see me. Even though it was thrilling, I feel conflicted because I know if someone saw it could make them feel uncomfortable or violated. I’ve only done it the one time, but is this something I need to retire?