How to Do It

The Ads on My Fiancé’s Computer Are Pointing to Something Sinister

I think I know what he was using them for.

Woman making a face of suspicion while looking over at a laptop.
Photo illustration by Slate. Photo by fizkes/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 met my now fiancé 12 years ago when I was in the process of a divorce. Sex was hot and frequent, but slowed down after the “honeymoon” stage. I have found myself relaxed and enjoying sex now more than ever, even though sex hasn’t been as frequent as our first year or so together. Recently, it seems that we make love most of the time when I go to bed before him. A couple of weeks ago, I noticed that he had ads for chatting online with women on his computer. I confronted him about the ads and told them I feel devalued knowing he was chatting with other women (which he denied, but now the ads are no longer popping up). I think he was using the chats to get him “in the mood” for sex as we haven’t made love since I confronted him. What should I do? I offered to watch porn with him so we can both get in the mood but he doesn’t want to.

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—Perplexed and Wishing for More

Dear Wishing for More,

While an algorithm that decides which ads to serve different people might absolutely choose to show a sexual chatting ad to someone who has engaged in, or searched for, sexual chatting recently, that algorithm will also display those ads to people who have never shown any direct indication of interest in such a website or app. Whether your fiancé has given you more concrete reasons to doubt his word over the years, or you’re simply suspicious of him or romantic partners in general, I think you should consider why you’re in a relationship with someone you don’t trust.

Dear How to Do It,

I am a fun, affectionate, beautiful trans woman. I did not come out and begin to transition until I was 36, and prior to transition, I was only attracted to cis women. About a year into hormone therapy, I noticed that I was now attracted to cis men, and now two years in, I am ONLY attracted to cis men. Learning to deal with men has been a struggle.

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I am a very sexual and asexually open person; I hated sex prior to transition, and now I love it. Sex is an enormous part of my identity and my spirit, and I love to share it. I am a solo-poly gal, meaning I only have casual sex with friends and share my boundless love and affection that way. I hate dating exclusively. Unfortunately for me, I have found in my dealings with men that even though an actual honest to god friends with benefits seems like a light ask, if not every guy’s dream come true, the “friends” portion of that seems to be too burdensome for many of them. Once I share my free-spirited philosophy on sex with men, all my humanity tends to get tossed immediately out the window as well, and suddenly I only get sexts or a constant barrage of insincere compliments trying to make sex happen faster, but no sincere interest in anything else about myself or my life or sharing theirs with me. If I try to change the subject, it will be continually steered back toward sex, or the conversation will just end.

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The obvious answer here is to hide my sexuality, but this is also my favorite part of myself—I don’t WANT to kill my own spirit in exchange for a connection. I spent 36 years hiding who I am and I just can’t abide hiding my true self. Worse still, here I run the risk of eventually growing to resent, then bury and lose, another piece of myself just as I was beginning to get to know her. I have the added wrinkle of being a fetish item for many, making me even more predisposed to being seen as a conquest and nothing more. I have the sneaking suspicion I am now experiencing what all women experience—a systematic reduction of one’s identity to a hole, until one’s spirit finally dies. I’d like that not to happen to me. How do I deal with men while being openly sexual AND a complete and lovable human being at the same time? Is it possible?

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—Trans in Turmoil

Dear Turmoil,

There are a lot of big concepts coming together in your letter, so I reached out to cosima bee concordia, co-host of the Drunk Church Podcast, for some help. Regarding the idea of experiences that are common to all women, she noted, “I do think all women experience misogyny on some level, but then the way that that experience, that misogyny is experienced, is very different. She seems very aware at the end that trans women are very much treated as fetish objects, right, like, we’re one of the biggest porn categories, everyone wants to fuck us, but then it’s a very common problem for trans women who date cismen that cismen don’t want to be seen in public with transwomen.” The particular kind of misogyny you’re describing is awful, and many women do experience it.

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There are also many other forms of misogyny, and you probably already have—and will continue—to encounter new and novel manifestations. One that I want to mention specifically is the phenomenon of emotional labor that is gravitating toward your lap. “If you’re in highly gendered relationships, there is a good chance […] that the emotional labor is going to be really one-sided,” cosima said. It is absolutely your decision how much work you’re willing to put in to help people broaden their understanding, or empathy, but do consider how much of yourself you’re hiding, and how much effort you’re investing, to be seen as more than an object by a particular person. We all have our own systems and metrics for weighing whether we’ll help with someone else’s work, which depend on an enormous amount of factors. If I could articulate my own, I’d lay it out for you, but I still don’t have a firm grasp on what goes into my decisions to engage deeply with a question that hurt significantly to hear, or walk away from an interaction because someone made a slightly misguided statement.

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It’s worth considering why your attractions are exclusively toward cisgender people. cosima mentioned an anthology called Transgender Marxism, which includes an essay about cisheteronormativy’s cultural dominance, by Xandra Metcalfe. And, if you’d prefer something more succinct, or less, well, lefty, her Instagram page might give your mind some things to think about. As cosima pointed out, while you don’t have to be attracted to any person, “there is no body part arrangement that you can assume for trans men over cis men,” and, if cocks are part of the appeal, those can be employed by anyone. Oh, the variety of dildos in the world! You can also consider what you found attractive about specific partners and look for themes, to get a more detailed understanding of your desire. You might notice some consistent similarities immediately, with more nuance becoming apparent later on.

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You don’t mention having discussions with your partners about what “friends with benefits” means to each of you. If you haven’t been having those talks, try doing so before you hook up. You will probably find that a significant amount of these conversations end with a decision not to hook up, but when you do proceed, you and your partner will both have a higher chance of getting what you both want out of the interaction.“You could certainly have an actual friend with benefits, that’s a friend who you are sleeping with, and have that sort of relationship, but if you’re just dating a bunch of people, and fucking them, obviously you’re not going to be friends with all of them,” cosima said. So do take some time to define what you mean by “friend,” along with your other nouns and adjectives, and communicate those details. With enough time, you’ll almost certainly find the people you fit well enough with to develop long-term relationships that work for everyone involved.

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Two years isn’t all that much time when we’re talking about any kind of major life change. When we’re talking about changes to the ways our identities are perceived by others—whether gender, a social role, or a career—life can be really heady for a while. Your feelings about sex have gone from hatred to love, which is another significant shift. Be prepared for your desires about the sex you’re having, and the relationships that sex is taking place within, to continue to change. And please do keep in mind the real risks involved with going into private spaces with people who throw your humanity out the window, or treat you like a fetish item. Make sure your decision to take those risks is intentional.

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Dear How to Do it,

How does someone have their clit played with while being penetrated? I can’t quite seem to get my preferred clitoral angles with my fingers while being penetrated by my partner. This is also, occasionally, a problem when he’s using a dildo on me if I am in certain positions. My partner is slightly above average, though I figure that the issue is a combination of the angles of penetration when we have sex, and my anatomy—despite long arms and hands. If I was able to finish from penetration alone, this wouldn’t be an issue, but, despite it feeling good, I do need clit attention in order to finish. We use vibrators, though I prefer to forego them during sex sometimes. He’s also not used to the coordination needed to polish a pearl while working pipes, which is something he’s learning to do. Any tips?

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—The Pearl in Question

Dear Pearl in Question,

I suspect that your issue is a combination of the angles of penetration, your particular anatomy, and that there’s something to do with penetration itself since this happens when your partner penetrates you and occasionally with dildos. I’m basing this on the stark differences in the kinds of clitoral sensations I experience when there’s zero penetration, or one finger, compared to the sensations I experience when I’m also being penetrated by an object with significant circumference. I’m guessing that you’ve been trying to make the kinds of stimulation that work best for you without penetration work during penetration. Start from square one instead. You might experiment alone with a dildo, or invite your partner and make this a group activity. Regardless, try several different kinds of sensations. Break this down into categories along the lines of types (rubbing or stroking, vibrating, tapping, and squeezing), speeds, and intensities of pressure. Then start trying stuff. Whether you’re more improvisational or systematic about this experiment is up to you.

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Do keep your focus on pleasure and fun. If you or your partner find yourselves feeling like a mutual orgasm during penetration must be achieved for sex to be good, do some introspection, have a conversation about it, or both. Absolutely do keep working toward finding the kinds of stimulation that work for you during penetration, and encourage your partner to keep building his, er, hand-cock coordination, but also keep an eye out for signs of sex starting to feel like work for either of you. To that end, just as you use vibrators sometimes and forgo them at other times, have some sexual encounters where you’re trying to orgasm during penetration and others where you have your orgasms before or after penis-in-vagina interaction.

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Dear How to Do It,

How do I respond to her suggestion of an open relationship without conflict? My girlfriend of three years recently asked if I want an open relationship. It came as a total surprise. We are 42 (me) and 39 (her). She is often very jealous of any of my female friends and finds it hard to trust. Early in the relationship we split for a few months. When we got back together she volunteered that she “cuddled” male friends but denied sex. I admitted to having sex with someone else during this “break,” for transparency and honesty. Aside from this “break” we’ve been monogamous.

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Two things happened recently. First, a friend of hers divorced and now has many sexual partners, including a BDSM relationship, which she shares a lot of detail about. Second, a guy I vaguely know announced he and four others had joint sex with my girlfriend years ago. I asked her and she confirmed it was true. She’s become much more open about her desires now.

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Out of the blue, she asked if I would like an open relationship. She said she thought we shouldn’t be possessive, that it would just be sex. I said I was worried I wouldn’t feel the same about her if she had sex with someone else. I know she wouldn’t cope well if I even flirted with another woman, so it all seemed out of character.

I want her to feel confident talking to me openly and need advice on how to put my concerns without causing an argument. Our relationship isn’t all that strong—she lies, is secretive, shows jealousy, and starts arguments. I suspect she’s recently cheated or has someone in mind. In principle, I could be open to swinging or us having sex together with others, but not yet. How can I address her lies and jealousy without making this conversation adversarial? How to approach my question about fidelity when I know she’ll become defensive?

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—Open Minded But Unready

Dear Open Minded

There’s no way to guarantee that voicing concerns about a renegotiation of the terms of your relationship won’t lead to conflict. And while conflict can often be neutral or even healthy, your use of other words like “argument” and, especially, “adversarial” leads me to believe you’re predicting an unhealthy conflict.

What you’re describing sounds like a vivid example of a relationship that is likely to be made more difficult by opening up. It sounds like you’re in a similar situation to our other letter writer “Perplexed and Wishing for More.” So, before you make any moves to open the relationship, you should ask yourself the same question: Why are you in a relationship with someone who you don’t trust?

—Stoya

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My boyfriend just asked me if he could send me snippets of porn he watches to show me what he wants me to do to him in bed. I feel slighted by this, because I already try to do things that I would otherwise not do already to keep him happy.

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