I Had Sex With a New Guy. What He Did Afterward Was a First for Me—And Not a Good One.

How to Do It Things immediately took a turn. Photo illustration by Slate. Photo by azndc/Getty Images Plus. Sign up for the Slatest to get the most insightful analysis, criticism, and advice out there, delivered to your inbox daily. How to Do It is Slate’s sex advice column. Have a question? Send it to Jessica and Rich here. It’s anonymous! Dear How to Do It, I’m a 45-year-old single, gay man in a smallish Midwest city. I just got back from a hookup where I had fun, but it took a weird turn at the end. I’m generally not into anal, so I list myself as a side on the apps. Tonight, a hot guy struck up a conversation with me, said he’d love to find a friends-with-benefits situation (which I am down for and is in my profile), and asked if I was up for receiving oral. I said I was, and I went over to his place. I had to repeat to him several times during the encounter that I wasn’t going to do anal today when he asked me to top him. (I didn’t say never—it’s something I’ll do sometimes in a longer term relationship, but definitely not on a first meeting—but I also didn’t say that I would in the future, just that I would not this time). That was mildly annoying, but it seems to happen often enough that I’ve gotten used to dealing with it. I also didn’t end up ejaculating when I orgasmed, which is pretty obvious when it’s oral sex. This happens about half the time with a new guy (and I’d told him that too, so this shouldn’t have been a complete surprise), but it also happens about a quarter of the time even when I’m just masturbating. I did make sure the other guy got off. But the vibe soured pretty soon after he did; we got him cleaned up, he made it clear he wanted me to leave right away, and then he pretty much ignored me while I got dressed. I half expected him to block me by the time I got home. While it’s not the first time a guy’s been upset that my saying that I wasn’t up for anal wasn’t me playing coy, nor the first time I didn’t cum with a new guy, it’s the first time I’ve had someone appear so disinterested once he finished. Now I’m wondering if there’s a better way to handle or communicate my limits. Previous boyfriends and naturally developed FWBs haven’t seemed to have a problem with any of these things, but they obviously knew me better than tonight’s hookup. Short of just avoiding all casual hookups entirely and only going there after either real dates or from previous, nonsexual friendships, is there a good way to make clear that I actually did mean the things I said? —Meant What I Said Please keep questions short (<150 words), and don‘t submit the same question to multiple columns. We are unable to edit or remove questions after publication. Use pseudonyms to maintain anonymity. Your submission may be used in other Slate advice columns and may be edited for publication. Rich Juzwiak: I think that in the post-nut clarity section of this encounter, there’s a lot of suggestion and inference that I’m not sure is the fact of the matter. He assumes this has something to do with his refusal to have anal sex, which was very clearly written in his profile and talked about before he went over. He assumes it has something to do with ejaculation or the lack thereof, but it seems like there was very little communication after the orgasms were had. So, you don’t really know what this other guy was thinking, which is the case when dealing with other people in general, and with strangers you meet for sex in particular. Jessica Stoya: I wondered throughout the letter how much this guy has done as far as really casual hookups because it’s a little unclear. I feel pretty justified in assuming that the amount of casual experience is low, but I’m not certain. Partners, people we’re dating, actual friends that we begin having sex with, even people we meet through social groups—that’s one kind of thing. And when it comes to casual hookups, it’s not to say be callous, and it’s definitely not to say expect or give unreasonable treatment, but you have to consider: What is this person to you? What does his reason for immediately shifting to a weird vibe and wanting you to leave and not interacting while you were getting dressed matter? Rich: Right. It’s all in the other guy’s head. It could have something to do with everything that happened. But whenever anybody is really adamant that you have to leave immediately after sex, to me, that reads more like a shame response. So, then it’s like, is he “straight” and hooking up with guys, and now the post-nut clarity is making him upset about that? Does he have a partner that he’s cheating on, and now that he’s come, he’s realizing the gravity of what he did? That person has a whole other world that you are not privy to at this point. Jessica: Did he have a boyfriend for three years who meant a lot to him, who would not have orgasms and then psychologically abuse him about it, and he’s just trying to keep himself together until the writer gets out of the door, because he knows that he’s having a big emotional reaction that has nothing to do with the letter writer? The speed at which I proceeded to increasingly unlikely reasons that this has nothing to do with the writer is because, with clients who have a hard time with rejection in the sense that they make assumptions and really believe it’s because of something about them, I make them do something I call “five reasons this has absolutely nothing to do with me.” So you just, on your way home, or while you’re taking a breath after being turned down, whatever it is, you come up with five. And when people are first starting to do this, by the time they get to five, it’s like outlandish scenarios to be able to meet the quota. But every single time that there is a rejection that is anything other than a direct, “I am not interested in this with you, specifically you, for this reason that has to do with you,” other than that, you just sit there and squeeze out five whole reasons that this could be something on their end, happenstance, or if you really have to go there for one or two reasons, things where the two of you are neutrally not a match (but you’re getting a B-plus). When people do this regularly and make it a habit, it often helps a bit. But if you just do it once or twice, it’s not going to work. Rich: Also, I mean, the simplest answer is that the guy that he hooked up with is kind of a jerk. He has transactional sex, and he doesn’t treat his sex partners like they’re actual people. I don’t think people should be impolite to somebody who just aided in their orgasm, but certainly people are—men, I would say in particular, and I’ve seen it happen with a lot of gay men, so that could be it too. The greater point is that the letter comes to us saying, “Now I feel like I should alter myself because this one guy was kind of brusque with me.” If your approach is working for you and you’ve had one encounter where this has happened, maybe don’t change it at all. Just keep doing you and hope that the next roll of the dice leads to a friendlier goodbye. Jessica: And it’s the context of it not being the first time that guys have been upset that he didn’t want to do anal. It’s not the first time that he has not ejaculated with a new partner. So if he’s run into a fairly uninterrupted string of guys failing to internalize the first, “I’m a side; I am not giving or receiving anal tonight,” I can see how that would maybe bring him to a point where he’s like, “This is a running theme, and I have to do something.” But the thing to do there is: The second or third time they ask you for an act that you have explicitly and directly said is not on the table, put your clothes on, and leave. Rich: Exactly. Also, another thing that stood out to me: He did have an orgasm; he just didn’t ejaculate, so it was a dry orgasm or a retrograde ejaculation, which is an interesting part of this. Generally, this happens when the semen goes into the bladder instead of coming out the urethra. It could be nothing. It could also be caused by conditions like diabetes, hypogonadism, and multiple sclerosis—so it’s something to definitely talk to a doctor about if you haven’t talked to a doctor about it before. I’ve never heard of it being selective, especially when he says this happens about half the time with a new guy, and it also happens a quarter of the time when he masturbates. That’s a kind of odd detail in the letter that I haven’t read about previously. Jessica: It is an odd detail. I’m glad you caught it. I have known several men over the years who, at times but not at other times, will have all of the nice feelings of an orgasm and all of the contractions without ejaculating, and it comes and goes, and vice versa, where they’ll ejaculate but not actually get the orgasm. It’s possible that this is a completely non-dangerous phenomenon, but please, please, please go get checked out because, as Rich was describing the possible causes of retrograde ejaculation, I was scrolling back in time feeling horror for sexual partners and friends, where I’m like, Oh, maybe I should have told them to tell their doctor. I wish I’d known. So, better to mention it at your next primary care visit or urologist visit and see what’s going on. Rich: Yes, check it. At 45, it’s time to be asking those questions. Jessica: But to directly answer the question: If you’re saying the things you mean, directly in understandable English, and they’re showing you that they don’t think you mean it, or they think that if they ask enough times, you’ll change your approach, you should leave. Rich: Yes. Besides taking himself out of the situation, I think what he did was the right thing. He didn’t end up doing what he didn’t want to do. So, mission accomplished. More Advice From Slate My partner has recently come out as nonbinary and bisexual. They have discovered this about themselves (or perhaps just been more open about it) the last year or so. I’m glad they are finding their truth, and I have tried to be supportive of them, helping them learn to do makeup, buying them nice heels and helping them pick out clothing, defending them to a few members of our families and other bigots. What’s really frustrating me, is lately, or the last year or so, they’ve made comments about lack of sex to our mutual friends and even around our families… Advice Sex