How to Do It

My Wife’s Surprising New Sexual Talent Has Me Concerned

Where’d she learn to do this?

A peach emoji next to a man looking suspicious.
Photo illustration by Slate. Photos by Getty Images Plus.

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,

This is weird. I’ve been married for 22 years to my wife; everything is mostly okay in the bedroom, just the usual problems 22-year-old marriages have. So, a few months ago we were going at it pretty intensely, and in the middle of lovemaking, I essentially asked permission for anal for the first time and she quickly said yes. Well, it was awesome and all that (first time for me) but here’s my question: I’m not “small” or anything, but I was able to slide right in there with no problem at all, and she seemed to handle it like an old pro. Is that a common thing for women who haven’t done that for 22 years or should I be worried she’s been getting side anal action for a while?

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—Turned On but Concerned

Dear Turned On,

If your wife were getting “side anal action for a while,” I would think she’d be a little more timid about opening up and revealing that. (Incidentally, Side Anal Action for a While will be the name of my queercore punk side project, should I ever found one.) If she’s going out of her way to deceive you already, she’d likely suspect that her ability to take you all in one gulp the first time might be suspicious, so she’d at least feign discomfort. Just a theory. On the other hand, she might just be chaotic. More likely, she has been practicing with toys, or she has mastered the ability to concentrate on relaxing that anal tends to call for. Or, for whatever reason, she’s just built that way. I don’t think it’s common, per se, for someone to be able to take a dick up their butt with no training or practice, and yet I’ve met guys who were able to bottom on the first try and loved it. I think more than being suspicious, you should be grateful that you found a partner that’s into what you’re into and, as a result, that you can have awesome sex with. It wouldn’t hurt to ask how she did what she did, but I’d frame it as admiration so that she talks and doesn’t immediately shut down.

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Dear How to Do It,

My 28-year-old boyfriend is very well endowed. The problem is, he doesn’t regularly get all the way hard, and he can orgasm this way, but having sex when it’s like this is nearly impossible, especially because I get really wet and he slips out. I know that this is mostly anxiety related. Getting him to see a urologist or sex therapist has been a struggle: He’ll agree and then change his mind. First thing in the morning he’s rock-solid, but any time after that it’s really a struggle. We’ve tried cock rings with limited success. Besides not putting too much pressure on him, what else can I do to help him?

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— Not Hard Enough

Dear Not Hard Enough,

The key is the “not putting too much pressure on him” that you mention, because I think the situation calls for a little bit of pressure. This very well could be a manageable issue, requiring the mere popping of a pill, which could help with his blood flow and mitigate his anxiety. I think he owes it to you to try, though you owe it to him to listen to any legitimate reasons he voices for not wanting to try. Make sure it’s clear how important this is to you, and how easy the fix could be. There are a ton of startups like Hims that prescribe and distribute ED drugs remotely and with minimal third-party communication. He could also just ask his GP, if he sees one with any regularity. While ED could indicate other more serious issues, your sense that his derives from anxiety is likely correct. Ideally, he would see a specialist about this, but life is rarely ideal. Still, ignoring your requests for him to take care of something that is easily taken care of may amount to a kind of laziness, and one that I have little sympathy for. Approach this with firmness—it’s a way of picking up the slack for his lack of it.

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Dear How to Do It,

I’m a 65-year-old divorced guy who has had a miserable sex life. I didn’t lose my virginity until I was about 32. I’ve had maybe four partners, including my ex-wife. They all wanted plain vanilla sex. I have some embarrassing limitations (built very small, have something the urologist called venal leakage which means it’s difficult to maintain an erection). I don’t feel like I ever got that good at sex, and I’m not confident at all in my skills. I haven’t had sex in as almost three years. Since we’re all expected to be pretty damn good at sex by now, how do I get these skills without being dumped for being bad in bed? Women have said I’m incredible at oral sex. I always make sure that my partner is satisfied at least with getting an orgasm through oral. What exactly is meant by being bad in bed?

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— Feeling Like a Virgin

Dear Like a Virgin,

While I appreciate the thought exercise, and I do really feel for you, asking, “What exactly is meant by being bad in bed?,” is like asking, “What exactly is meant by, ‘This food is good?’” It’s going to range! One could assess the culture and say, “Stamina,” but over the years, people have written into this column expressing affinity for fast-cummers. (I’m in that appreciation camp—I will take a partner’s quick nut as a compliment every time.)

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Maybe the most reliable feature associated with sexual aptitude is consideration for one’s partner. Connection and an investment in the pleasure of another person are going to be useful across the board, no matter that specific sexual taste (unless that taste is for specifically not connecting and being effectively used, which some people are into). If you’re making sure your partner is orgasming through oral every time, you have the right mindset. (Do beware, though, that some people don’t come from oral and so you may hit a snag with your strategy.) I would lead with that, internally and externally: You’re a giver. Let that be your source of confidence, and try to limit the effects your intercourse shortcomings have on it. That confidence may go a long way in terms of your attractiveness as a partner. There will be women who want to get railed by a big dick, but what can you do? You can’t will yourself hung. You can only be the best version of what you are, and work well with what you’ve got. Cultivate that.

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Dear How to Do It,

I’ve recently started going to sex parties and usually have a great time, but I have one issue I don’t know how to deal with. Sometimes when I get with people with penises (I’m a cis woman) they can have a bit of what I am assuming is situational/performance anxiety-related ED. Which is understandable. However, despite enthusiastic attempts from both of us, sometimes the dick won’t get/stay hard enough to play. I’m OK with having non-penetrative fun, but sometimes I feel like the other person makes it a mission for me to have an orgasm. That sounds nice, but it feels like it’s less about wanting me to feel good and more about proving they can do it. Because of this it doesn’t always feel good and I try to adjust their hands or mouths or give directions but none of them really seem to take it. It’s like tunnel vision. If this was just a one-on-one scenario and we were somewhere private, I would try to end the meeting and not care if I didn’t see them again. But because it’s a group thing and many of these people are frequent flyers I know that I will, not only see this person again that evening, I may see them at the next meetup. I don’t want to ruin someone’s confidence for the evening, but I also don’t want to feel like I’m wasting my time with something that isn’t going to happen for either of us. What can I say to end these trysts without being mean?

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— (Sex) Party in the USA

Dear Sex Party,

The question of graceful rejection is one I’ve pondered in my limited experience with public sex parties, especially when groups (within the group) form and I’m attracted to some but not all members. It seems a little messed up to say, “You and you, stay—you, go,” as valid and as necessary as it may be at times. Mostly I hope that people take the hint when they realize I’m not paying attention to them.

But men often don’t, and I know this can be the case especially when women are putting out these signs. So I checked in with my friend Melissa Vitale, who told me she’s attended over 500 play parties. (She’s also a publicist who’s represented play parties and swingers’ events, and her company, MAVPR focuses in part on intimate wellness.) “I’m always happy to keep women safe at sex parties and [help them have] amazing sex because that’s what parties are for, not horrible feelings,” she told me during a phone call.

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Vitale said that pre-play conversations with potential partners can help minimize the flaccid awkwardness you’re coming up against—something to the effect of, “I’m really interested in penetrative sex,” or “Listen, my thing that gets me hot is I like to be pounded,” or even, “I like to feel a hard dick inside me.” This will at least theoretically start to separate those who can hang from those who can’t. But since wood is unpredictable, Vitale also gave a suggestion for tapping out to move on: “One of the phrases I like to use when someone is not pleasing me is, ‘You know what? I’m good. Why don’t you sit this one out?’”

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Vitale brought up an important point that may help you frame these pitfalls of this kind of super casual sex: “No female should feel guilty if their partner failed to please them.” She said that if you are made to feel guilty by a partner you’ve rejected, you can and should report that to management.

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“As women, we’re taught to be very nurturing and apologize for taking up space,” she said. “And we’re supposed to think of other people’s feelings. But when you look at the reverse of how men behave in this space, some men don’t even feel apologetic, even when they intentionally cause harm.” She clarified she was speaking mostly of cishet men, but I’ve definitely seen some boorish behavior from gay guys, too.

In terms of moving forward after rejecting someone, Vitale suggested to take each case as it comes. If you had a good conversational chemistry with someone but it wasn’t banging in the sex department, you can continue being friendly while drawing boundaries as needed. But you have no obligation to give anyone your time. The kind of interacting that goes down at these parties is intense and it might call for a rather explicit telegraphing of your interests and intentions. You might actually have to say, “I’m not interested in doing anything other than talking with you.” I know it can be uncomfortable, but so many options in one space means rejection is part of the process—anyone who can’t handle that shouldn’t be attending, and anyone who lashes out as a result of it, again, should be reported. A responsible promoter will be keeping a list of people who don’t know how to behave themselves and banning them.

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But if this is all too much for you, Vitale has a scaled-down solution: Throw your own highly curated, smaller-scale party. All you need is some lighting, music, and snacks, and you can host your own orgy in the comfort of your own home, making sure the guest list is filled with people that you actually want to have sex with. Worth a try!

Rich

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