I Had an Unexpectedly Great Sexual Experience. Now I’ve Got to Figure Out How to Recreate It.

How to Do It Photo illustration by Slate. Photo by curtoicurto/iStock/Getty Images Plus. Our advice columnists have heard it all over the years—so we’re diving into the How to Do It archives to share classic letters with our readers. Have a question? Send it to Stoya and Rich here. (It’s anonymous!) Dear How to Do It, I’m a healthy 42-year-old male, currently single, and open and adventurous sexually. For the first time in a decade probably, I was caught masturbating by a neighbor who let herself into my discreet side yard looking for a missing cat. I won’t go into all the details, but she saw everything, including me cumming all over myself. She’s funny and sexy and was clearly not distressed by the sight. It was an incredible orgasm for me, noticing her staring at me with a wry grin just as I was about to finish. I’ve never been particularly ashamed about masturbating and have long enjoyed showing off for partners. I was a little surprised by how much I loved being startled so unexpectedly, though.The long and short of it is, I would love to safely explore getting off under such circumstances further, but I am not sure how to. I’m not interested in hurting anyone or getting in any trouble or doing any damage to my good career or name. Can you offer any suggestions for exploring this kink safely? — Eager to Share Dear Eager to Share, I’m tempted to deprive you like you deprived me: What happened after she caught you? We fade out on you coming on yourself, which is I guess cinematic but too vague an image for my taste. I wish you would have shared your interaction after immediately after, since being covered in cum has a way of affecting the dynamic. My desire for this information is not entirely about wanting narrative resolution—I wish I had some indication how she behaved after she caught you, and whether she’d felt skeeved out. I’m not saying she should have been. Among the first rules of benign trespassing is when you go digging around other people’s property, you might just find them jerking off. I just want the full picture of what, exactly, you’re idealizing. It does seem that the implied enjoyment in her staring and wry grin is what rang your bell, so perhaps a masturbation club/party would be for you. It’s going to be a lot easier for you to find a party of this sort that caters to men who want to do this with other men, but there are so called “Jack and Jill” parties for a mixed-gender clientele. You might find such events, or at least the opportunity to show off your dick-polishing talents, in a space for swingers (though navigating a swingers club as a single man might be tough). Of course, if being startled is part of the point, you’re not going to be able to coordinate that in its pure form, as being unsuspecting in this context is an impossible thing to cultivate. Roleplay with a game partner—perhaps even this neighbor, if she really did enjoy her discovery so much—is about as close as you’re going to get to that ethically. Just something to keep in mind as you pursue this. —Rich Juzwiak From: My Neighbor Caught Me in … a Very Compromising Position. I Can’t Believe How I Reacted. (July 17th, 2022). 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. Dear How to Do It, I’m in a happy, stable, loving, open marriage. We’ve been together two decades and have two children. A few months ago, we went to a sex party and he met a nice young lady. She said she was a lesbian just starting to experiment with men. Subsequently, we were both texting/flirting with her and finally had her over. During the threesome she was WAY into his dick (which, to be fair, is great), and I felt sidelined/ignored by both of them. It was the least pleasant threesome I’ve had—not a disaster, but not something I want to repeat. Since then, he has continued to see her. They are having hot sex and he’s thrilled. The issue? She is 21. We are in our 40s. When we first met, I assumed she was in her mid-20s and did not clarify—although I still had misgivings and felt that was too young for me! She’s smart and seems relatively sane, lives independently, has a job and a college degree, and seems to be close to her parents as well. Up to now, my baseline assumption would be that any man who sleeps with someone less than half their age is a predatory creep. I feel like this reflects poorly on him and bodes ill for the future. But I’ve talked to some poly friends who shrug and say if she’s legal, it’s fine. I have never exercised a veto before, and I don’t want to do so now, especially since part of me feels like I’m just hung up from being rejected. I am really in my feelings about this and it’s hard for me to sort it out. What do you think? — Dirty Old Woman Dear Dirty Old Woman, Many things can be true at once! Your feelings of rejection may have increased your sensitivity to the situation, which is an eyebrow-raiser, even from my completely uninvolved perspective. If you felt accepted and super into her, you might be willing to overlook the stark age difference along with your husband. I’m not convinced that your bias and jealousy are clouding your judgement—more likely, distance is affording you clarity. People in their early 20s are generally inexperienced and more likely to take risks/overlook (or simply not be aware of) the repercussions of their behavior. I mean, your husband has a dickmatized 21-year-old lesbian on his hands—how much experience could she possibly have in this specific arena? How could she even have a concept of how things might go, and any resulting emotional collateral? I think your side-eye is in order. That said, I tend to agree with your poly friends that in purely sexual terms, this much of an age difference doesn’t have to be an issue. Young, horny people are going to find a way to have sex, and with a certain mindset, it won’t matter if the good dick they’re getting has been on this earth for as long as they have or twice the amount. But I also think knowledge and experience afford a certain amount of power, especially when the knowledgeable and experienced party happens to be a guy and both parties happen to live in a patriarchal society. And so, it’s really important for that guy to be careful with the younger person’s feelings and to be clear about the parameters of the relationship, with regular conversations. You can assume that as an adult she will be able to handle and advocate for herself, but you also shouldn’t be surprised if she turns out to be deficient in those areas. I think your challenge is to test your assumptions. Take stock, observe your husband insofar as you are capable, and ask yourself if you were right: Is he a predatory creep? Sweeping generalizations are like 21-year-olds: capable of being right on, but prone to falling apart before your eyes. For the sake of keeping the peace, I think it’s best if you watch closely and speak up only when you can raise concerns that he doesn’t seem to be considering. It’s your job as a partner to draw attention to oversight. You’re his backup eyes. But I think that’s about as big of a role you can play here unless you really want to revise the terms of your agreement. Unless you actually do want to introduce vetoing, it’s going to be hard to put the 21-year-old back into the bottle without major drama. —R.J. From: My Husband and I Had a Bad Threesome, and Now I’m Questioning His Character. (February 6th, 2022). Dear How to Do It, I’m pretty sure my husband is obsessed with all things anal. He refuses to admit it, but I’ve seen open tabs of hardcore anal, dildos, plugs, and more on porn sites left open by mistake. When I ask him what kind of porn he likes, he never mentions “anal.” The thing is, mostly on nights where I’ve had several drinks, he insists on trying anal. I have tried for him many times in the past to enjoy this kind of sex, but the general consensus is that I’m not a huge fan and probably will never initiate it. He says it’s not a big deal in the moment, but I feel like I am not meeting his sexual needs, as shown by him keeping his porn viewing a private thing that I just happen to stumble upon. Any advice? —Butt Out Dear BO, You’re not into anal, but your husband insists on engaging in it, mostly when you’ve had several drinks? This sounds like it might be coercive on his part, and that would cross the line—on top of the fact that if you’re inebriated, you may not feel pain signals soon enough to prevent harm to your delicate rectum. If you’re willing to be anally penetrated to meet your husband’s desires, that’s your choice, but if you’re a maybe before you start drinking and a yes after a couple, your decision-making and consent is blurred. While you don’t say how many times you’ve seen your husband’s tabs open, I imagine it hasn’t happened very often. Is it possible that what he’s fixated on is your specific anus and he was coincidentally looking at anal porn the couple of times you’ve glanced? Or is it possible that this is something he feels shame about and wants to hide from you, or generally? It doesn’t seem like your communication around sex is very deep, and that’s something to consider working on. My hope is that if the two of you can build more comfort talking about your sexualities you’ll get to a point where he can be more open about his porn-viewing preferences. And if you don’t already have specific activities you engage in for your enjoyment during sexual interaction, suggesting a couple that sound fun for you seems like a great place to start. —Jessica Stoya From: My Husband Has a Secret Desire He Doesn’t Know I’ve Seen in His Browsing History. (January 26th, 2022). More Sex Advice From Slate I am a compulsive masturbator. I love to go at it when there is some risk involved. I have an unrelenting desire to be watched/caught masturbating by a stranger. I’ve masturbated in my car, in various stores while shopping, and various public settings. The more taboo and risky, the more I enjoy the rush of endorphins. I am constantly daydreaming of a female stranger discovering me and happily wanting to enjoy the show. I have also been married for two decades. Never miss new Slate Advice columns Get the latest from Prudie and our columnists in your inbox each weekday, plus special bonus letters on Saturdays. Advice Dating and Relationships Sex