How to Do It

I Keep Having Amazing Sex. Until the Second Date.

What am I doing wrong here?

Two men looking worried with eye animations around them.
Animation by Lisa Larson-Walker. Photos by Getty Images.

Our advice columnists have heard it all over the years. We dove into the How to Do It archives to share a selection of classic letters with our readers. Have a question? Send it to Stoya and Rich here. It’s anonymous!

Dear How to Do It,

My husband of four years and I have an open marriage, which is going well. We have had quite a few threesomes or more-somes together, which have been awesome, but mostly we see other guys separately, usually from hookup apps. We live in a big coastal city, so there are lots of other gay men around online. When I meet up with other guys, it’s usually after a lot of chatting online, establishing trust and generating a rapport. These are just hookups, no date beforehand, and while they’re all friendly, fun hookups, there’s no emotion involved. I’ve met something like 20–30 guys this way.

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The issue is that the first time I meet up with a guy, sometimes the sex is absolutely amazing. Dizzying. The bed is wrecked, the neighbors scandalized, etc. However, if I meet up with these guys again, the sex is never anywhere near as good the second time. I don’t know if it’s about expectations being too high, or natural variability and reversion to the mean, or what … but it’s really disappointing. The second time is a dud more often than not, and there usually isn’t a third time (and when there is, that’s often less disappointing but still nowhere near as good as the first time). What am I doing wrong here? The sex I’m having with my husband is just as great as it ever was. Am I just addicted to the thrill of a new body? I don’t want to keep seeing these other guys for a sustained relationship outside my marriage, and there are always more guys to meet, but it would be nice to experience more than one decent night from each guy!

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—One and Done

Dear One and Done,

You are so lucky that I suspect what you are experiencing is not luck at all but some sort of advanced witchcraft. It sounds like you have managed to avoid two major pitfalls of sex apps. The first is the immediate disappointment of reality versus the fantasies crafted in one’s head during a chat. The story that I’ve heard and experienced much more often goes something like: When I meet up with other guys, it’s usually after a lot of chatting online, establishing trust and generating a rapport … and then we get together and it doesn’t work at all. The second common gripe is the inability to score a second date/hookup after the first one went swimmingly. That I just tend to interpret as relative immaturity and compulsive next-best-thing-ism.

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I’ll tell you again, my concupiscent compadre: You are lucky. You’re conjuring and having good sex and then landing follow-up fun. Add to that what sounds like a jealousy-free open relationship with a partner that you’re still having great sex with, and it sounds like you aren’t just having your cake and eating it too but doing it while living in a Hostess factory with the metabolism of a small bird. That the sex is tapering off with these random guys could be a blessing in disguise: If it remained intense, they might want to stick around and ultimately get in the way of your committed-swinging lifestyle.

You should be happy with what you have, because it rarely gets better. Given that you have a sort of scientific control in your consistently good sex with your husband, I’d guess your ostensible problem with underwhelming repeat sex is a psychological issue, not a physiological one—maybe you’re on a first-time-hookup high, then reality sets in and it’s only after a second session that you realize this random guy isn’t all that incredible. (It’s also hard to precisely evaluate this because you aren’t clear on what’s making the sex bad. Are you guys able to maintain erections? Are you coming? Is there just a decreased intensity the second time? Is it possible to put your finger on it at all?) If you really, really want more, and I know it’s human nature to do so, try a slightly slower approach. Get to know the guys a little bit. Meet up and chat before your first or second sex encounter, foster an association that helps you see each other as something more than body parts with which to help each other orgasm. Believe me, I know the fun in living life like a great white shark and needing to take a bite out of every dude to even understand what’s in front of you, but if you’re trying to cultivate buddies, why not try a friendly approach?

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—Rich

From: “My Husband Hasn’t Touched Me in Six Years” (July 29, 2019)

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Dear How to Do It,

I have a good friend who has a habit of, nearly every time we get drunk alone together, coming home with me. It’s been escalating—last time we definitely did reciprocal oral, and we may have briefly had sex. (Neither one of us is sure because we were so drunk, which is ridiculous.) The problem is that when he’s sober, he doesn’t want us to hook up. After each time, he says this is a bad idea, that we shouldn’t do this again, etc. (It’s never I wish we hadn’t done this, only we shouldn’t do this again. My view: It is a bad idea, but that ship has kinda sailed.) When he’s sober, absolutely nothing happens. After the second time a couple months ago, I broached the idea that we should just hook up, but he said he didn’t want to complicate things because he enjoys hanging out with me. When I’m drunk, I’m pretty slutty; I’m extremely unlikely to say no in most cases, especially since I can’t help thinking we should just have sex. He’s the one who doesn’t want to while sober, but when he gets drunk, he can’t seem to not come in. At this point, this to me is getting a little ridiculous, but I’m not entirely sure what I can or should be doing here. For context, neither of us is interested in a dating or a relationship of any kind—I have other friends with benefits. At the same time, we live in a very small town, and going out to bars with him is an important part of my social life. Thoughts?

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—Drinking Buddy

Dear Drinking Buddy,

Take away the substances and your picture could be printed next to unrequited in the dictionary. You want it more than he does—“it” certainly being the sex, it seemingly being an ongoing play-buddy arrangement, and it quite possibly being a full-on relationship, though you say otherwise. If he’s not budging, you’re going to have to maintain your appetite for the scraps he’s having you feast on. You prepared for that?

Personally, if someone only wanted to get naked with me when he was drunk, I’d feel pretty insulted. Is the circumstantial implication that he’s viewing you through beer goggles? Does he harbor some sort of shame about having sex with you and/or sex in general? Regardless, are you sure you should have sex with someone usually reluctant when you’re both drinking heavily? Is all of this way too fraught for a casual arrangement? I can answer that final question from here: yes. Yes, it is. Exercise some self-control and keep things platonic. Keep your drinking buddy, and find a new guy to fumble around with drunkenly—one who’s keen to play sober, as well.

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—Rich

From: “It Crushes Me That Well-Endowed Guys Can Do Something I Never Will” (Sept. 4, 2019)

Dear How to Do It,
Last year, my husband of two years—together six—and I were out to drinks with his childhood friend and the friend’s fiancée. (We’re both straight couples.) When we were several in, we were talking about losing our virginities, and his friend’s fiancée made a comment along the lines of “well, you know what they used to do.” I did not know what they used to do! It turns out they masturbated together as teenagers, which included “giving each other a hand.” I was taken aback by this, but they all seemed to think it was hilarious, and my husband was embarrassed, so I shrugged it off. Teenagers do things. We didn’t talk about it again.

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Recently, I was out with the fiancée for her bachelorette party. My husband was at the bachelor party the same night. Someone joked about them getting too friendly with strippers, and the fiancée said they were more likely to get too friendly with each other. She then started telling the group that she knew my husband, her fiancée, and at least one other guy from their friend group masturbated together into college and their 20s (we’re all around 30). She said she suspected they still do it now sometimes, but she doesn’t care because it’s “just jerking off.” I’m now kind of paranoid about this! I did some Googling that suggested this is a fetish for some guys who are with women. Um, is it? Is there a way I can bring this up with my husband without accusing him of cheating? If he’s hiding a major part of his sexuality, I kind of worry about what else he could be hiding.

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—Five-Knuckle Shuffle

Dear Five-Knuckle Shuffle,

It does seem like more straight-identified guys are getting into mutual masturbation with other so-called straight guys these days. Or maybe connectivity has made this phenomenon more accessible and easier to gauge and discuss? Ya never know with these things. A recent GQ trend piece explored the phenomenon of “straight” masturbation clubs, and I’ve seen online ads for such clubs that specifically target “straight” guys and more or less rebuke gay ones. I put “straight” in quotes because, sitting around, dicks out, perhaps polishing a penis that does not belong to you, sounds pretty far left of strictly hetero to me, but it’s also increasingly clear that there’s infinite space in the gray area between a Kinsey 0 and a 6. It is therefore conceivable that there are guys out there who mostly have sex with women but enjoy the male bonding that comes with sitting around and busting some nuts with other men. As you may have noticed, spending time with naked men is fun.

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So, perhaps this is not a major part of your husband’s sexuality but a minor one. The way I’m personally inclined to think about this goes something like: He could be sitting around with his buddies playing poker and holding cigars, or they could be sitting around watching porn and holding their dicks. It’s all time-passing leisure. If he’s not depleting himself of a sex drive from whacking it too much, or having his dick stripped raw by his buddies’ calloused workout hands, what’s the difference? You, naturally, are under no obligation to take such a laid-back stance. (After all, he’s your husband.) I think before you determine a method of bringing this up without accusing your husband of cheating, you should figure out if you consider this to be cheating. Many would! If you’re in a monogamous arrangement, it’s perfectly reasonable to expect your husband to keep his hands on his own controller and not be playing another guy’s joystick. You can bring this up quite easily by referencing the previous conversation on this topic that you were both present for. Request more detail and clarity. He might be embarrassed, but he owes you the full story. For maximum extraction potential, work from love and compassion, not shame.
The fiancée of your husband’s potential jerk buddy, though, is a real piece of work, isn’t she? She’s probably making things more difficult by being so loose-lipped about your husband’s potential predilection, something you have every right to feel sensitive about and not want blabbed. I think you’re in the right to tell her to cram it, if you’re so inclined. You needn’t be delicate with her.

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—Rich

From: “I Think My Husband Masturbates With His Best Friend” (May 13, 2019)

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Dear How to Do It,

I’m a hetero woman in her early 30s. I started seeing a new guy after a bad breakup. I expected it to be a fling, but I’m starting to get real feelings for him. The best thing about this is also my problem: The sex is incredible. Specifically, he is incredible at sex. I very rarely come from oral sex with new guys but I did with him the first time, in minutes. He knows exactly how to touch me and where, he is very responsive to my body—he’s just really skilled. So much so that I almost feel shy having sex with him! I am pretty experienced and confident in my body, but when we have sex I feel lazy, like I’m doing less than he’s doing. (He comes from a Christian background and didn’t have sex until he was 25, and he also has a smaller than average endowment, so I think he accepted the card he was dealt and stepped up his game.) He’s a good guy and I like him a lot, but I feel a weird pressure to up my game with him because he’s so good, and that in turn makes me wary of sex sometimes. I wish I could take this as a challenge, but instead it’s making me feel inadequate, probably for no good reason. How do I get over this?

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—Unicorn

Dear Unicorn,

In the worst-case scenario, you are being lazy, but guess what? He doesn’t seem to mind! Sometimes it happens with sexual partnerships that there’s someone who does the bulk of the work—they even have a name for it, the “active” partner (also known as a top, though this designation is obviously more popular in same-sex pairings). In this scenario, your mere presence is enough to turn him on and get him to work—it’s like being a celebrity (or even a vaguely known influencer) in a bar and getting free drinks. You think Gigi Hadid is turning those down?

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It sounds to me that your dynamic with this guy has been determined by chemistry. It’s how the cards fell, and if you’re both happy, there is really no need to change anything by looking for a problem. The only challenge at hand is enjoying yourself, so relax. Unless he tells you that you’re “inadequate,” assume that you are not—his gusto is great proof that you’re doing everything right, even if you aren’t doing very much at all. Some guys are givers, and regardless of how he is hung, this one sounds like a gift horse. Please don’t look him in the mouth (unless he wants you to).

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Do check in and make sure he’s enjoying himself. If he says he is, believe him and lean in … to his face. You’re coming in minutes. Why fight it?

—Rich

From: “My New Boyfriend Is So Good at Sex It Makes Me Feel Bad” (March 17, 2019)

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This morning, I found my partner’s porn. Initially, I did not intend to snoop—I wanted to check the weather on his computer (which I don’t think he would mind, as he uses my computer without asking sometimes) and I found his porn browser open with furry bondage porn open. After I saw this, I snooped. Some of his “favorite” pages on the browser really upset and disturbed me.

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