How to Do It

I Slept With a Guy for the First Time. I Have a Dark Suspicion About What He Did When I Wasn’t Looking.

A couple having sex.
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,

I’m a 33-year-old woman just getting back into the dating scene after a decade of being married. I met a guy on Tinder and we hit it off immediately—we both agreed that we weren’t looking for commitment or monogamy, but that we’d enjoy something ongoing and with a level of companionship beyond typical friends with benefits. We ended up texting all day, every day for several days before meeting up at a bar near his house. Having skirted sexy-chatting during the week, we both knew what was likely to happen and had talked about protection earlier—I mentioned that I was on birth control but that I prefer to still use condoms with new partners. He was OK with that, and on the day of our date, he even text asking if I had a brand preference.

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The date went great and, unsurprisingly, we ended up back at his place, both a little tipsy. As we were fooling around he grabbed the box of condoms, lamenting that he hadn’t thought to open the shrink wrap before the heat of the moment, and proceeded to open one. At that point I wasn’t paying much attention to the process and just figured he’d put it on. He made a comment that it had been a long time since he’d worn condoms, but he’d also said it had been a long time since he’d had a partner, so I didn’t think much of it.

Later, we changed positions and when he laid on his back, I realized he wasn’t wearing a condom. It was in the blankets and I laughed that it had managed to come off and he didn’t correct my assumption. At that point—and yes, I know this is irresponsible and not advisable, but—I shrugged and told him it was fine and that I didn’t feel like stopping to put a new one on. Neither of us had any recent sexual activity, and to be honest, we had such a great connection and I had kind of already been considering offering to not use condoms together as long as we used them with any other partners. So in the moment, I just kind of thought, “well, I wanted us to be able to be spontaneous in the future anyway so screw it.”

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This morning, though, it occurred to me that when I saw the condom in the bed, it actually did not look like it had been unrolled and just “come off” … it kind of looked like it had just been taken out of the wrapped and tossed aside. This really, really bothers me.

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I really like this guy a lot—we’re already planning on seeing each other again, communication has been great, and he seems to adore me—but I’m really off put but the lingering thought that he never put a condom on but wanted me to think that he had. I feel weird bringing it up because I eventually did consent to condom-free sex that same romp, but it’s very different if he knew I wanted to use condoms and just pretended to wear one. But I don’t even know if that’s what happened! He ended up passed out at the end of the night so I think he may have gotten a little more drunk at the bar than he wanted to admit, and we did have wine back at his place too. I don’t want to ruin a good thing by fighting over it as we did end up deciding not to use one in the long run, but I just feel like this might be a red flag I’m ignoring in the flush of a new romance. Literally everything else about this guy seems like a great match for me otherwise. What would you do here?

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—Unwrapped

Dear Unwrapped,

I think you absolutely need to bring this up, and see what he has to say about what happened. It’s possible it fell off. It’s possible that he did merely pretend to wear the condom in the first place. It’s possible that he won’t be honest about what happened. You’ll have to listen to your gut on this one. How he reacts to your broaching this subject will likely tell you a lot.

You may be right that the choice you did make mid-sex to continue without a condom was not ideal. Frequently during sex, we’re so focused on pleasure that our critical thinking can fall by the wayside. Making serious decisions, like dramatically increasing our risk, should happen before or after that altered mental state. But you were clear with him about this boundary beforehand, and he made it clear he understood. If he admits he “stealthed” you—or if you strongly suspect he did after speaking to him—I think you already know this man isn’t a good partner, casual or not. In at least one state, that’s now legally considered sexual battery. 

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Dear How to Do It,

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I am a 40-year-old woman who is newly single. Recently, I was working alongside a-19 year-old, and he and I kept flirting back and forth. I thought I was making too much of it and that I was crazy for thinking he’d be interested. I also thought I was crossing a line with such an age difference. We were working together alone a few days later, and as he continued to flirt, I teased him that I’m not in his age bracket. He said to me he doesn’t see women in an age bracket and that he REALLY wants to see me outside of work. Am I going too far with this young man? I hate the saying, but I am the same age as his mother.

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—Bad Mamma

Dear Mamma,

I’m less worried about the age gap itself than I am the fact that the two of you work together. You, as the more mature party, should communicate the inappropriateness of flirtation in the workplace and apologize for your part in it. If you were both in your 40s, not reporting to each other, and working in different departments, I’d be more relaxed. But you do seem to be working together directly, and the age difference is an inherent power imbalance at work so deep it’s unlikely other factors even it out. I’m sure there are plenty of attractive people of all ages who you don’t work with out there. Take some time to find them.

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Dear How to Do It, 

What are my ethical obligations when it comes to creating a place on the Internet to express fan appreciation for a porn performer? Back when the internet was new, anybody could stand up a webpage for almost any purpose and nobody would question it. But today, after GDPR and DMCA and the #MeToo movement, it doesn’t feel right for a private individual to use images and information about another private individual in this way anymore. And I’m aware that unlike in other media, performers are hardly ever entitled to royalties and likely won’t gain from any ongoing sales of their existing performances. That’s further complicated by the fact that many popular names from the business are retired from porn and might rather that other people not continue to revisit that part of their lives. So it seems like a fan site has a lot of potential to hurt a performer with no gain in exchange for that risk.

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I want to make it clear that awareness of these boundaries is important to me, so it’s not as if I’m looking for an excuse to have any sort of communication or other contact with a performer to figure this out. Is it even possible to have a space for this type of fandom that doesn’t approach exploitation or abuse? If I’m not a journalist creating a record or a publicist serving the performer, can I do this in a way that is respectful and also doesn’t harm that person?

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—Trying Not to Be a Creep

Dear TNtBa Creep,

As you reference, one large potential for harm I see is if this performer, let’s call them Pat, has moved on to a different profession where being recognized could cause problems. I personally know one nude model who lost her job because she was outed, and I have seen several news stories during the pandemic of people being fired when their OnlyFans account was discovered. In a follow-up when I reached out to you, you said that the performer’s legal name and nationality are fairly well known, but you don’t say how recognizable they are after retiring. Do they have active social media channels, and what kind of content do those channels post? Another factor is family: Pat’s partner probably knows about their previous employment, but they may have children who don’t. Think through whether success with your project could bring up their past in a way that significantly disrupts their home or job. This is a real risk.

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You also said that you don’t intend to post about this person’s current life or private matters. I think that’s important. If all you’re doing is collecting links to legal sources of this performer’s work, I think you’re fine. But you still might want to ask.

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Consider actress Brandy Ledford. She modeled nude, including as Penthouse Pet of the Year, before her big break, and kept her nude work secret for years. She’s now comfortable speaking about it publicly, but sees a consent issue in your letter. “You know I never gave consent for any of my photos to be on the internet, because I modeled in a day before the internet, and so it is always jolting and it seems disrespectful when someone posts a [nude] photo of me on their account,” she said.

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I’m not sure when image and performance releases began using phrases like “across the universe” and “in any and all media (whether now known or hereafter devised)” in their standard text, but before the internet, it was pretty difficult to conceive of a media distribution network like what we now have, which makes consent a complicated concept.

For Ledford, “it comes down to getting permission. Especially in the day and age of consent and how important it is.” That’s what she would want, she said.  “If someone reached out and asked me if they could use a photo of me, I would respect that a lot more than if they used it and didn’t ask.”

Dear How to Do It,

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I’m a late-20s nonbinary person (assigned female at birth) who’s a complete virgin. A lot of that is due to anxieties and self-esteem issues that I’ve been working through, but the biggest obstacle to me having the sex life I want is my dysphoria. I generally get off with clitoral vibrators and can barely touch myself without getting upset. Any sort of penetration is terrifying to me, to the point where even thinking about just using a tampon sends me spiralling into a breakdown or makes me actually pass out. It’s honestly barely related to my gender—I just have always hated having a vagina.

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Of course, plenty of people don’t enjoy penetration, but the problem is my biggest fantasies all involve … getting screwed silly. Do you have any suggestions for easing into this (alone, since I don’t have a partner and wouldn’t feel comfortable with a casual hookup)? Should I just try anal and get over using my vagina? Is this the kind of thing I could even talk about with a therapist? I feel so lost, like I just can’t get my fantasies and reality to line up.

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—Want to Get Railed

Dear Railed,

This is absolutely the kind of thing you can talk about with a therapist. The Kink Aware Professionals Network can refer you to a sex-positive therapist. Your local queer organization can probably refer you to a therapist who is sex positive and aware of LGBTQ-specific needs. And apps like BetterHelp can connect you with a therapist who is likely to be a good fit digitally, for sessions via telemedicine from the comfort of your own space. If the first therapist isn’t a good fit, move on to the next one. You also might have a short call before scheduling to ask them what their experience is with concerns like yours.

What I’m hearing is that penetration is terrifying to you, but it’s the thing you want. This isn’t as atypical as it might feel, and conflicting emotions are deeply human. You might spend some time thinking about the details of your fantasies, or asking yourself for more details when you’re having one. What’s the difference between getting screwed silly and inserting a tampon? I can come up with a number of possibilities. See if you can spot any in yourself, and use that knowledge to decide how to approach practicing penetration on your own.

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I do think it’s best for you to try penetration alone before doing it with a partner. If you’re the person doing the action, you can stop immediately, without the process of verbalizing, being heard, and being responded to. Your asshole is definitely an orifice worth exploring, and if you’re comfortable trying, your fronthole is too. A dildo might be useful, since you say that touching yourself is upsetting. Set your goals low—just seeing what happens for a minute is enough to start with—and don’t try to do everything in a single session. Growth isn’t always visible at first. Be gentle with yourself. I think you’ve got this.

More How to Do It

I’m a single father in my late 30s interested in getting back into the dating game following a two-year hiatus. As someone who spent most of his 20s involved in making pornographic movies, I’ve spent my 30s normalizing sex and relationships. As an extremely well-endowed man, I also came to accept that I’m cursed with a “gift” that can only mean one thing.

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