How to Do It

Yikes—I Just Realized How I Know the Hot Older Guy I Want to Meet for Sex

A muscled man next to a Tinder logo.
Photo illustration by Slate. Photo by Ranta Images/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 am 25, female, single, and horny as hell because I have taken quarantine very seriously, since I live with a roommate who is high-risk. However, my roommate has headed home and will remain with her parents for at least a month, maybe longer. In anticipation of this, I’ve gotten back on the apps hoping to find a regular hookup buddy during my window of freedom. I also changed up my match parameters in terms of age, because sex with an older man has long been a fantasy of mine, and I figure if I’m going to expand my boundaries a little bit, now is as good a time as any!

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Well, I matched with a 49-year-old guy who is hot, interesting, and great at flirting. He’s also single and takes COVID seriously, which are musts for me. But of course there’s a problem.

“James” is the father of a friend of mine from high school. Not just a friend, but a girl I briefly dated. (I was questioning a lot back then, as teens do but have ultimately settled on “straight but flexible”) Like, I have been naked with her. I only met him very briefly a couple of times back then and wouldn’t have recognized him because he’s gotten a lot fitter since he and her mom divorced. He also didn’t recognize me when we matched—we figured out the connection together, in conversation. And to his credit, he immediately said that if that made it too weird, he would understand.

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It doesn’t actually bother me, but two out of three friends I surveyed said it was a bad idea to hook up with him, one because “it just could get messy” and the other because she thinks he’s a creep for even considering hooking up with someone his daughter’s age. (The other friend said it was hot and I should go for it, but then made a joke about a threesome with the daughter, so—taking it with a grain of salt.)

So am I being stupid for considering this (because, again, SO HORNY)? He’s super hot, has been nothing but considerate (I had to beg him for a dick pic!), and we seem to have similar kinks. I don’t even think he realizes his daughter and I were ever more than friends (because our “relationship” was so brief). She and I aren’t close anymore other than occasionally liking each other’s posts on Facebook and Instagram, and I’m not planning on getting married to him or anything. I just want him to bone me! A lot! In my apartment, where I will finally have some privacy!

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—Bad Dad?

Dear BD,

I think a taste for older men is a simple and not uncommon sexual quirk, and at 25, I think you’re old enough to discern benign interest from creepy fetishization. People do have successful relationships with significant age gaps, and you aren’t even looking for that—you just want a hot hookup.

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Your nay-voting friend has a point, though—it could get messy. It’s worth thinking through the possible ramifications of hooking up with the father of an early romantic partner. You might cause her to feel really weird around her dad if she found out. The story could circulate and get back to her, or even your family, who also might feel strange about the situation. More immediately, he might feel odd, struggle to get it up, and be too busy being sad about it to go down on you. Spend some time imagining various outcomes and weighing whether you’re willing to accept the risk. A wilting willy is one thing, but other scenarios might not seem worth it. Or maybe it will all seem fine!

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There are plenty of other men in their 40s available on dating apps, so passing on this particular person doesn’t have much of a penalty. You’ll have to make your own choice, though.

Did you write this letter, or any other this year? We want to know what happened. Email us!

Dear How to Do It,

I’m an early-30s woman. I have difficulty orgasming—I’ve only ever been able to come with a fairly powerful vibrator, and sometimes that takes a very long time to the point I give up even though I’m very turned on. Over the course of my late teens to my late 20s, I suffered a number of orthopedic injuries to my pelvis, hips, and lower back, including a slightly herniated or slipped L5 vertebrae that is still out of alignment. Is it possible that my high pain threshold, spinal alignment, or buildup of scar tissue in the pelvic ring is also contributing to a loss of sensation or decreased sensitivity in the clitoris and vagina? I’ve read Come as You Are and had very enthusiastic partners willing to take whatever direction I give them, but I’ve still been unable to orgasm with a partner.

—Orgasm Injury

Dear Orgasm Injury,

Many women take a long time to orgasm, or require a very specific kind of stimulation—almost always clitoral—to achieve climax. Have you always had difficulty orgasming, or did that start at the same time as the injuries? Since you think this may be related to your spinal situation—and especially if there does seem to be a link—you’ll want examination by a specialist. If you have a treatment team you can reach out to, you should do that. If you don’t, your previous orthopedic doctors or primary care physician are probably good places to ask for a recommendation for who you should see.

In the meantime, you can gather more data. Does your experience change if you change positions (lying on your side, hips propped up on a pillow, lying on your stomach, knees up, legs straight), or if you change which area of your clitoris you’re stimulating? Experiment and keep track of anything that feels better or worse than usual.

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Remember that this may not necessarily be a medical issue. Try to have patience with your body, and focus on enjoyable sensations along the way as much as you can. Good luck.

Dear How to Do It,

My husband is interested in viewing ethically produced amateur porn (an ethical Pornhub). Where can he find it? He’s not a fan of the feminist porn I watch (e.g., Erica Lust).

—Decent Dollars

Dear DD,

I’m not sure what kind of porn your husband is a fan of, but I can make some guesses. Based on years of discussing pornography with fans of the medium in person and via internet chat, I’m assuming he’s turned off by the high production nature of Erica Lust’s work, and wants to see more “authentic”-feeling videos. Cindy Gallop’s MakeLoveNotPorn might be more his style. MLNP couples film themselves, edit themselves, have the ability to take their content down if they choose, and are paid a percentage of the purchase fee.

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I think the other best solution is direct-to-consumer outlets like OnlyFans (which I have a paid page on), Just for Fans, or ManyVids (which I’ve done work for in the past and have an inactive page on). Performers—established professionals and unknown amateurs—post their own work, usually self-shot or with a camera operator they’ve chosen and are comfortable with. Your husband can look around Reddit, Twitter, and other spaces where sex workers advertise their content online, find people who feel intriguing, and follow their pages. He can think of it as an adult Instagram feed—something he can curate himself.

Dear How to Do It,

I am a junior in college who has been with my amazing girlfriend for more than a year (I am also a woman). We are doing long distance for the next few months, and I keep running into a problem that I don’t really know how to solve. When the pandemic first began, we were already long distance. We would sext fairly regularly, something that was enjoyable for both of us. Over time, it became anxiety-producing for me. It turns out I have a lot of internalized guilt and shame around sex, and I have no idea where it comes from other than, you know, society. A passing joke my girlfriend made about me being the hornier one out of the two of us made me spiral for days, and talking about masturbation (something we used to discuss quite freely) has made me cry regularly.

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After a while, I decided that sexting was making me feel worse, and I told her I wanted to stop doing it. She was understanding and sympathetic, and we stopped. Around a month later, we got to see each other in person for a while, and things went back to normal. Most of these issues I had been having didn’t come up when we were in person together and actually having sex, and things were good. Now, we are long distance again, and I am back to spiraling into shame if we try to sext or even talk about certain things casually. I still masturbate, but I no longer talk to her about it and I always cry immediately after. Once again, she has said that she doesn’t want to make me uncomfortable and respects the fact that this stuff is hard for me right now. But I can’t stop worrying that I’m ruining our relationship by getting rid of the sexual element to it, or that I’m disappointing her and making long distance even harder. Beyond the fact that I worry about the effect this might have on her I also don’t WANT to be this ashamed of the fact that I have sexual desire and this anxious about admitting that to my own girlfriend. I feel like if I had no sex drive it would be one thing, but I do, I’m just afraid of it. Is there any way I can get over this, or do I just have to wait until we can see each other again and hope this hasn’t done irreversible damage to our relationship?

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—Shame Bell

Dear Shame Bell,

I think it’s worth listening to your shame for details. The next time it happens, maybe when you’re crying after masturbation, acknowledge it. Say “I am ashamed and I don’t know why.” Sit with that for a bit. Maybe there are other emotions in there, too. I imagine fear is a possibility, and strongly suspect you feel vulnerable in those moments.

You might be experiencing some self-judgment. Wherever sex-negative messages come from, it’s worth examining them and working through why we disagree with them. Especially when those messages are currently affecting our sexuality. Make a list as they come to you, and spend some time understanding why you disagree with them.

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You can also explore your emotions after the moment has passed. Journaling helps lots of people. Others think through things better in the shower, bath, or while walking. Whatever gets your mind moving.

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It also might help to write out what you feel sexuality is. For instance, sexuality to me is an array of physical and mental interactions that can occur between one person and themselves or between any number of partners. It’s a beautiful way of communicating with another human, and a wonderful expression of connection. It can foster intimacy and trigger the release of happy brain chemicals. In its most purely physical form, it’s a delightful sport. We all have the right to explore our bodies and give ourselves pleasure. A paragraph or so like this in your own words can be something to hold on to when you start to doubt.

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If working on this on your own doesn’t get results, a sex-positive therapist may be your best bet. And do continue to communicate with your girlfriend as you’re comfortable—let her know you’re working on it.

—Stoya

More How to Do It

I have been married for about 15 years to my husband, and we have two kids together. He is a kind and caring person, a good dad, and a thoughtful partner. We enjoy spending time together. The problem is I am 0 percent attracted to him and don’t have any desire for sex with him. He hasn’t changed very much physically in the time we have been together—it’s my response to him that has. I thought for a long time I was one of those people whose desire decreased as I got older (late 30s). A couple of years ago, I had an affair that lasted several months, and I learned I do still desire sex. A lot. Just not with my husband.

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