How to Do It

I Finally Had Sex With My Crush, and It Was … Not What I Expected

He left me feeling like I was the problem.

Left, a neon eggplant emoji. Right, a woman grimacing.
Photo illustration by Slate. Photos by SIphotography/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 just got to have a sexual experience with a guy I’ve been desiring for a long time, and it was such a disappointment. He could not penetrate me. We tried all kinds of positions. We are both big but not obese, and he has a big “beer” belly. He kept telling me to relax, but I was relaxed. I wanted him. I was well-lubricated—my panties were soaked. I am in my early 50s and never had children. The few sexual partners I have had never had a problem like this. I have used dildos without problems. My overall impression was that he was “short,” but he left me feeling like I was the problem, that I was too tight. I have not been having a lot of sex but masturbate regularly and enjoy the “penetration” part of it. This is definitely a sexual relationship, and I don’t see it going on if the encounters continue in this manner. Is there something I could do to not be so tight?

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—Desperate Girl

Dear Desperate,

He left you feeling like you were the problem? That’s concerning, and I’m not sure you ought to pursue this liaison. Surely there are other people in the world who you find attractive—people who won’t blame you when things don’t go as expected. It can feel sad to learn that someone you’ve desired for a long time isn’t who you thought he was, but it’s always better to have that information sooner rather than later.

If you decide to persist with this partner, jessica drake has an explicit educational video on plus-size sex that might help you troubleshoot. You also can stretch out beforehand with a short, thick dildo. And you can experiment with positions that present your vulva with as little flesh preventing penetration as possible—knees up, on your side bent at the waist, and face down with a stack of pillows under your hips. But the best thing in this situation still might be to mourn this crush and move on.

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Dear How to Do It,

I’ve been with my wife for nearly 13 years now. Our sex life has been very meager and unsatisfying for me for the last six years or so. Sex never seems to be anywhere near my wife’s mind. About four years ago, after occasional arguments about this, we made an agreement that if I want sex, I have to directly tell her. She rarely turns me down, but she only makes her own requests for sex when I’m upset about something. I appreciate that she seems to be in this for my own satisfaction and nothing else, but it’s made me feel like sex is a chore to her, Thus, I don’t ask about it more often than once every 10 days or so (I would love for it to be far more often than that). It’s also kind of humiliating to ask your partner, “Do you want to have sex?” every single time.

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The sex itself is very vanilla, and any attempt I’ve made to add any variety to it is either turned down or she consents but I can tell she’s really not into it, and we never try that same thing again. I don’t have any specific fetishes that need to be explored, but I would love to be even a tiny bit adventurous (we were both virgins before we started dating).

All of this has led me to being very withdrawn about my sexual feelings. I’ve asked before about getting counseling or therapy, but her response was to entirely stop the conversation at that point, and I’m afraid to bring it up again. What can I do to address any of this? Do I have to just keep pushing for therapy/counseling?

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—Regretfully Horny

Dear Horny,

You don’t mention positive qualities your partner displays, nourishing aspects of the relationship, or children, and your silence on these details is noteworthy. Have you considered divorce? Your wife’s libido is consistently lower than yours, she isn’t as explorative as you, it’s not enjoyable when one partner treats sex as a chore, and the fact that she only initiates when you’re upset probably doesn’t help matters. You could absolutely dissolve the bond and go in search of partners who want the same things out of sex that you do.

However, your wife rarely turns you down, and you ask for sex every 10 days or so, which studies show lands you pretty near the center of “normal.” You also say you try new sexual activities but your wife isn’t into them. You should acknowledge the effort that she’s putting in to try these new things! Even if it’s only once, that’s one time she’s stretched outside her comfort zone.

If a separation seems too drastic, then one possibility could be to figure out how to ask for consent without making it feel humiliating. You might take a look at queer porn, such as Shine Louise Houston’s Crash Pad series or Tobi Hill-Meyer’s Doing It Online and Doing It Again series, for some models of how to communicate about sex and consent effectively and erotically. You can also get into masturbation. Your sexual relationship with yourself is valid and should be valued.

Finally, I do think you should revisit your desire to have a conversation about therapy with your wife. Pick a good time, when everyone is calm, not rushed, and in good spirits. (After 13 years I imagine you have some idea of when your wife is receptive to a challenging conversation.) If she tries to stop the conversation again, you could ask her about hesitancy to discuss this topic. Good luck.

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Dear How to Do It,

A guy I’ve been messing around with and sorta-boyfriend for a little over a year now proposed I (we) start camming as a way for me to make extra money while having fun doing it. I am a semi-exhibitionist in that I post nudes and semi-nudes of myself but never for money or acceptance of messengers asking to get to know me. I do it for more creative expression and in the name of art, and when I feel horny but can’t get any sex play from him or masturbating is not enough. I have seriously considered his proposition, but I am concerned about being recognized. Since I have a very visible and public daytime gig, this concern is real. He suggested wearing disguises. He is also planning on getting me a collection of toys of my choosing to use in the sessions when he isn’t available to be with me. We see each other one or two times a week when our schedules allow. Do you think this is a good idea? Any suggestions or reads to make this work?

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—Cami Wannabe

Dear Wannabe,

Your concern about being recognized is valid, as is the fear that recognition might jeopardize your main job. The mechanic who was fired over her OnlyFans account in mid-2020 comes to mind, as do a number of women who’ve lost their livelihoods over the years because of nude images surfacing from their early adulthoods. Yes, it’s sexist and unfair, but it’s worth thinking through whether this would be worth possibly losing your daytime gig over or whether you’d prefer to continue pursuing fulfillment via nudes and semi-nudes.

Disguises might work. You’ll want to cover any birthmarks, tattoos, or other identifying details. You’ll also want to choose your shooting locations wisely—decorative touches in the background can be just as recognizable as your mouth or eyebrows.

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You say your nudes are about creative expression, but I suspect he’s getting something sexual or emotional out of the idea, based on his desire to provide the toys you’ll be using. If camming sounds like a fun sex game, and you’re willing to take the reputational risk, go for it. But if you’re after something more artistic—more of a self-expression—I advise you to procure your own props and make your own choices about what you’re using, wearing, and doing. Another wise move: Control your own content. Hold onto copies of your ID, which you’ll upload to sell content. Get releases from any fellow performers or videographers. Make sure the accounts are in your name and use a unique, secure password. The more you can do to maintain ownership and control over the videos you make, the better.

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Dear How to Do It,

I’ve been in a hetero relationship with my partner for four years. Over the course of that four years, our sex life has been uneven. We used to have sex a few times a week, ranging from 10 minutes to nearly an hour. I loved it. It was hot and loose. But in the last couple years, I’ve been able to last longer, while my partner cannot. To be candid, I spend a lot of time and effort trying to help get them to cum, but when it comes to me, I feel like I need to take the lead to reach orgasm while they half-ass on their end, and I end up having to rush and miss out on the build that makes it more gratifying. I feel bad bringing it up to my partner because I don’t want to hurt their feelings, but I could go for so much longer, and I think I’d enjoy our sex more if they weren’t so easily worn out. Is there a way to bring this up without hurting their feelings or ways to make my partner enjoy having sex for longer periods of time?

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—Endurance Is a Problem

Dear Endurance,

For my own gratification, I’d love to know why you declare the hetero nature of your relationship but not who is which gender.

You might hurt your partner’s feeling. Ruffled feathers are a possibility. But absolutely nothing will change without a conversation. You could also hurt their feelings or ruffle their feathers by remaining silent. I recommend you approach them gently. Think through exactly what you want, and write out what you’re going to say, or rehearse it in a mirror, if you think you could use the  help. Read the room to the best of your ability. If they’re tensing up or becoming defensive, you’ll want to slow the conversation down. This doesn’t have to be addressed in one go, so take that pressure away now.

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You have options, depending on what’s happening here. Do they get worn out from orgasming repeatedly? If so, try to pace the paroxysms out. If they have low aerobic endurance, have a talk about them getting winded, mention the sexual connection, and offer your support, should they choose to take action. If they’re generally lethargic, especially more so than a few years ago, they should mention this at their next physical. If you suspect it’s something else, ask them what they think is behind the change.

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Are you sure you have to rush? Or do you feel like you’re trying to achieve orgasm before they get tired? If it’s the latter, you can take over stimulation yourself at times, alternating with your partner. You can stimulate yourself while they hold you or engage in some other kind of contact. As the more sexual person in the pair, you’ll do well to maximize your masturbation pleasure. But talking to them is the first step in trying to make this work for both of you.

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—Stoya

More How to Do It

My wife and I stopped having sex regularly after our kids were born. It dwindled from almost daily sex to maybe once a month. She hated her post-pregnancy body and felt like kids should be her focus. If we did have sex, it was often rushed, and she would ask if she could just give me a hand job instead. We even tried therapy, but sex ended up at the bottom of my wife’s priorities. She would get angry if I suggested sex and would say she found my sexual “neediness” unattractive. I love my wife and the last thing I wanted to do was push her, so I stopped trying and decided to take care of my needs through masturbation, but she caught me once and said she found it pathetic. About a year ago, I started to feel desperate. I tried to open up a discussion about our missing sexual life but was quickly shut down. “That part of my life is over” was my wife’s response. She’s 41.

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I was feeling deeply depressed. One day, I went to a massage parlor. I was wary, but there was something so healing about human touch. Since then, I’ve been to several. They vary wildly, and I’ve walked out of many of them, but I’ve found a few regular spots that are friendly and well-run with therapists who are well treated and decently paid. The women I see are thoughtful, funny, and empathetic about sex and men’s bodies’ needs. It’s a job for them, but they also see us at our most vulnerable, and perhaps I’m fooling myself, but it seems like a two-way relationship. I do feel ambivalence about myself for these physical needs, but I continue to go. While I still desire my wife, I don’t feel the need to press and annoy her, and I understand that part of her life might be over. (It’s been six years since we even kissed.) The thing I fear the most is that the image of my wife, of her body, is being replaced by the images of these other women, with these massage ladies fill a gaping hole in my life. Should I stop? I’m sure I risk Robert Kraft–style humiliation, but I’m not sure that living without regular sex is a healthy alternative either.

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