How to Do It

I Accidentally Recorded Myself Having a One-Night Stand—and Sent the Tape to a New Lover

A car has noise coming out of it.
Photo illustration by Slate. Photo by kloromanam/iStock/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,

I’m a straight woman who recently matched with a guy on Tinder, “Joe,” and through sexting—which is all we’ve done so far—we’ve discovered that Joe really likes hearing stories of my past sexual experiences. I was happy to oblige and share details of hookups I’ve had in the past. As part of one story, I sent Joe a screenshot of a brief text exchange I had with a paramour (with his name cut out). With another past hookup, we had sex in the back of his car, and I later discovered that my phone made a voice memo recording. I edited it and sent it to Joe, in which you can hear thrusting, as well as my panting. The voice of the guy is not in the excerpt, and there is no identifying information for either of these men. Both of these were one-time encounters, though I have had sporadic contact with the second guy since our hookup.

I am questioning whether I did something wrong, in terms of sharing these things without asking the consent of my past partners. (I also never mentioned the accidental recording to the second man; I wasn’t intentionally hiding it, but it didn’t occur to me to bring it up.) Telling stories is one thing, but I’m worried I may have crossed an ethical line. What do you think?

—Kiss and Told

Dear Kiss and Told,

I think that you did technically cross an ethical line, but you crossed it by a fingernail. If we, for the sake of metaphor, consider sharing revenge porn to be on par with grand larceny, your behavior amounts to stealing a pack of gum. It’s hard to imagine a scenario in which, upon hearing that you’ve shared brief, anonymized excerpts from chats and sex, your former partners express great distress, but it’s certainly possible, and they’d have every right to do so. Those moments that you shared with a stranger with them belong to them, too. You could tell them what you did to clear the air, but regardless, don’t make sharing such interactions a habit and stick to storytelling.

Dear How to Do It,

Hypothetically, how would a homely 50-year-old obese straight woman find and hire an escort? Let’s say this woman recently divorced after 20 years of marriage, her husband’s infidelity occurring over many of those years. And this woman understands and accepts that because of her age and appearance the likelihood of finding a sexual partner interested in sex with her is low to nonexistent, and rather than put herself through inevitable repeated rejection, would rather pay someone to pretend she’s attractive. This imaginary woman lives in a large metropolitan area in the middle of the country, but online has found only men available for other men, and none for women. She has for the first time in her life discovered toys, and enjoys pleasuring herself and becoming reacquainted with the sexual side of herself. But the profound sadness believing she will never again know the thrill of someone telling her she is everything, that she drives someone wild and he can’t stop thinking about her … I think if I could have what I knew going in was “the last time,” I could have closure that that part of my life is over. Any suggestions you might have that I could pass along to this hypothetical woman would be appreciated.

—Seeking Arrangement

Dear Seeking Arrangement,

It wouldn’t be right for me to recommend that you (even in your hypothetical form) do anything illegal, so I’ll recommend you do something that is totally legal: Google “escorts for straight women.” Be careful.

Your resignation to be rejected and remain loveless in scenarios that don’t involve sex work bums me out. Hope is good for mental health. Hope facilitates results. But as a fellow pragmatist, I hear you and admire your willingness to cut the hand-wringing and get to rammin’. If your sadness is profound, I don’t think casual sex is going to ultimately cure you of your malaise. Even the best transient dick tends to amount to just a temporary distraction (especially when the terms of securing said dick ensure that the arrangement has virtually no chance of develeoping into anything beyond a patron-client dynamic). Get laid and have fun, but consider working on yourself, too, perhaps with the help of a therapist.

Dear How to Do It,

My friend and I have always been just friends, but I know he’s sexually attracted to me. We’ve been friends for years, and even though it’s been platonic in terms of my emotions, he’s seen my sex tape, nudes, and knows about my sex life extensively. For context, his career involves him seeing lots of beautiful naked women all the time, so I really didn’t think much of it either. I’m a queer woman and generally open, and he’s not the first who’s seen my stuff. He told me he’s masturbated to my stuff before, and I was like, OK. The thing is, I was always fine with it because he respected my boundaries. I told him that I like that we are just friends, and he said he totally understands, and for years it was fine. We’d hang out all the time and never once did anything happen. The other night, we were both drunk. We were having an amazing time, laughing and chatting and all that. We ended up fooling around—no sex, not even kissing, just us masturbating next to each other and fooling around.

I was most certainly drunker than him, but it felt really good, and I enjoyed it. I came. I was curious about being sexual with him, and in the moment, I liked that it happened. In the morning, however, I felt violated. And I wasn’t sure if it was because I was mad at myself for letting this boundary disintegrate because now the nature of our relationship is changed, or if it was because I felt actually violated. I’ve been clear about us just being friends, right? Alcohol has been the cause of many mornings where I wake up and, although enjoyed the night before, regret it. Or worse, when I was in the throes of my past alcoholism, I was raped. Last night, there was definitely some boundary-pushing, but I don’t believe it was completely nonconsensual. The nature of our relationship has always been clearly platonic by the firm lines I drew, but he definitely, openly fantasized about me. I really don’t think he was being malicious, but that depends on how much the alcohol played a role, which I can’t gauge.

I’m not sure where to go from here, and I’m not sure what to think about him. Recently, I’ve been thinking that our friendship is beginning to run its natural course. Our interests are starting to move further and further away from each other, and our lifestyles as well. If a guy is drunk and a little bit obsessed with me, and I’m partially undressed in his bed and he knows I’ve been horny all day, even if I laid down those firm boundaries, I understand how awfully tempting that is to want to at least fool around, and then I’m extremely enjoying it, and here we are. I want some guidance to find out whether my friend violated my boundaries and if I should be concerned, or if there is some mutual responsibility for this happening and I’ll have to see if I want to continue our relationship (as friends who fooled around one time).

—About Last Night

Dear ALN,

I think you’re clearheaded about the gray area that you’ve found yourself in, which is kind of like turning on your high beams in fog—not much help, but it’s something. Going into this encounter, the guy showed a propensity for being creepy: Telling someone with whom you have a platonic relationship that you’ve masturbated to them is already crossing a mutually acknowledged line. You don’t think he was being malicious when you ended up jerking off together, and it’s conceivable that he wasn’t: Some friendships make the passage into sexual relationships and even romances and that transition requires direct action, which is the consensual dissolution of previous boundaries. Perhaps his thinking was something along the lines of, “Finally, this is moving in the direction that I’d hoped.” Your outward enthusiasm, which even in the fog you define with clarity (“It felt really good and I extremely enjoyed it”; “I liked that it happened”), could have seemed like confirmation.

I thought this sentence maturely approached accountability while leaving space for the validity of your own feelings: “I wasn’t sure if it was because I was mad at myself for letting this boundary disintegrate because now the nature of our relationship is changed, or if it was because I felt actually violated.” The thing is, both could be somewhat true. Maybe you were swept up in the moment with someone who was opportunistic to the point of being predatory. You were drunker than he was, and there are certainly people who believe that consent is impossible when alcohol is involved, though from an official standpoint, things are less cut and dried. As the Rape, Abuse & Incest National Network points out on its website: “Different states have different definitions of intoxication, and in some states it matters whether you voluntarily or involuntarily became intoxicated.” Again, more nebulousness. If you were incapacitated and blacking out, I’d definitely be taking a harder line here, but it seems that you remember the night pretty completely. (If you are concerned about your drinking—you mention “past alcoholism”—I hope you have or can find a support network to address that as well.)

I urge you to trust your read on the situation, understanding that this gray-area sex is extremely complicated and that there’s not always a good name for what happened. You say you think this friendship may have run its course, and I think you say that because you know it’s true. This is probably someone you’re better off not knowing. Maybe the friend that you need is someone who would maintain the boundaries you’ve set even when you yourself seem drunkenly eager to tear them down. If you need firm closure in order to move on, one thing you could consider is restorative justice, which could help provide mediation between the two of you via a third party (and without going through the legal system, which tends to fail survivors). You asked if you should be concerned, but I think you already are, and validly so.

Dear How to Do It,

I’m a bi woman married to a straight man. My sex drive and sense of adventure are both much stronger than his. He will mostly only have sex at night in bed, two possible positions, once a week or so. I’ve tried talking to him about what I like and what he might like, getting strategies from my therapist, initiating with different times and places and scenarios and acts, but he really can’t get into anything other than our current basics. I love him and he’s a great partner, but this leaves me sexually frustrated. I’m wondering about outlets that are not cheating but that might give me some of what I’m missing. I read in your column about men masturbating together online and am curious about trying this with women when I have some time to myself. However, I don’t know where I’d even start to seek this out. Any tips?

—Helping Hand

Dear Helping Hand,

With your partner’s blessing and once lockdown is over, you could look into a sex club that caters to women. Even in a city like New York, where public sex technically violates the sanitary code, there are plenty of play parties specifically for women (the ones I’ve heard of tend to be inclusive to trans, queer, and nonbinary clientele). From what I understand anecdotally, you’re not likely to walk into a gym’s sauna attached to the women’s locker room and find yourself in the company of someone who’s interested in rubbing one out—this is, at least, much less common than what you can find in the men’s room. There seems to be a pretty steep gender divide there, and I don’t know that you’re going to just happen upon a jerk-off buddy. You also have the option of attending a masturbation/orgasm workshop along the lines of that which legendary sex educator Betty Dodson hosts, but beware that her Bodysex workshop books up fast and costs (via “suggested” donation) at least $1,000 for nonstudents. Plus, it’s in the service of learning, not orgying. Killing Kittens, which made a name for itself via IRL bacchanals, has transitioned to social distancing–friendly screen-based events, and some of those are women-only. Perhaps they’re worth checking out as well.

You could, of course, look for a buddy via apps, as many men do, but again, I urge you to do this ethically with your partner’s knowledge and not behind his back when you find yourself with extra time on your hands.


More How to Do It

Recently, I went on a few dates with a man who repeatedly said he finds me gorgeous and is very impressed with my career. I thought he was a great guy himself. I gave him head, and he said it was “maybe the best head of his life.” Dude never texts me after that night. I didn’t text him either because I had initiated our last date. I’m being sexually rejected all the time and I am a very, very attractive woman. I have an hourglass body, exercise all the time, and have a career in mechanical engineering. When I look at who swiped on me on dating apps, the feed is practically infinite. When I walk down the street, I turn heads. Yet I have a really hard time being pursued. I will meet a guy, and things fizzle quickly. Dudes who know I’m single and horny have my number and don’t initiate plans with me, or cancel if I initiate. I am OK with casually dating and friends with benefits because I’m busy. I worry I am becoming desperate. Can they smell the desperation? Is 2020 the year I masturbate myself into oblivion and take a break? Or am I just an arrogant asshole because I’m hot?