How to Do It

I Have One Recurring Problem When I Hook Up With My Crush

It’s not fun for either of us.

woman with hands on hips and an illustration of a flashing broken bone
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 have been hooking up with a guy I’ve had a long-standing crush on. My mind is blown that it’s even happening. The issue here though is that I cannot successfully ride this guy! I am very wide-hipped and sort of a body builder. He is slender, and his body is narrow. When I am on top it’s not pleasurable for anyone. I feel awkward and literally just move him around on the bed, and there’s no actual motion where it needs to be. My hips end up hurting after only a few minutes. Also, he’s my first uncut guy. I feel like my old tried-and-true moves are not working, orally or sexually speaking! I have spent time this week researching on how to make sure he’s having a good time and I’m not hurting him. I just really want to wow this guy, and I am feeling inept.

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—Crushing the Crush

Dear Crushing,

You know when you’re in a public restroom and there’s pee all over the seat, and even though you wiped it, you still can’t bring yourself to put your butt cheeks down, so you hover? My first suggestion is to hover just over his pubic bone, with his penis inside you, and let him thrust with his pelvis. Another thing you can do is squeeze the sides of his thighs with your ankles while you’re on top, or put your hands on the middle of his chest, to brace him. Essentially you’re using one part of your body to hold him in place, while you move the other part. Think like you’re a jazz dancer performing isolations—separating your body into sections and moving them independently. In fact, taking a Zoom class or watching a few YouTube videos in basic jazz dance might help.

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You can also consider other positions. Both of you laying on your sides, facing each other. Both of you on your sides, facing the same direction. Upright reverse cowgirl—him sitting, you on top facing the same direction as him, with most of your weight being carried by the floor and the arms of the chair. And you can experiment with in-between arrangements—one of your legs in between his, one on the outside of them, with your torso more of a diagonal across his.

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As for his foreskin, direct communication is the way: “How do you like to be touched?” You might try grasping the middle of his cock, and then gently sliding the foreskin back and forth. Depending on how much of a foreskin he has, you might want to err on the side of closer to his head. Patience is important here, as pulling the skin back too early in the arousal process can cause some people pain. Orally speaking, you can take the whole cock into your mouth even when flaccid, baggy prepuce and all. That can be fun to poke your tongue around in. You can do the same rolling your tongue around the head, flicking the meatus, sucking the side of the shaft as you would with a circumcised penis. Deep throating works the same way. Don’t overthink it.

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Dear How to Do It,

I’m a 36-year-old recent divorcée, and I’ve spent the past six months exploring BDSM for the first time with a boyfriend who has a much longer history with it. Overall, the relationship has been warm and supportive and good, and the sex has been incredible—I am genuinely very into submitting to him—but I still occasionally wrestle with some negative feelings in the aftermath. I don’t think the problem is actually about the sex, which always feels good in the moment. I think it’s about the fact that I want more from him, in terms of the relationship, than he wants to give. (He’s an even more recent divorcé than I am, although who knows if that’s really the issue.) He’s honest about his emotional limitations, and I have decided to keep seeing him despite them, for now. But I sometimes get annoyed that he is getting everything he wants from our interactions and I’m not, and I think that feeling might be exacerbated by our Dom/sub roles. I’m not sure if I’m ashamed of myself (my behavior is basically opposite of “the rules” I was taught as a teenager: He is very much getting the milk for free) or disappointed with him or what. Any ideas on how to reframe, or where I should go from here?

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—Lovelorn Sub

Dear Lovelorn,

My gut says your needs aren’t being addressed. I wanted to check that feeling, so I reached out to friend of the column and BDSM writer Sinclair Sexsmith. They suspect what you are actually asking is:  How do I submit to someone in bed, in a BDSM context, and not feel used?

“Submission can be a tender, raw experience: a focus on the present moment, a slowing down of time, experiencing the deep now. Being in that state can be a revelation, a relief, a refuge,” they say. But Sexsmith notes that there is a dangerous stereotype about submissives that extends to women in general: “that they are doormats. That they are pushovers. That they allow themselves to be used, or even ask for it, or deserve it.” But, Sexsmith continues, submissives have “needs, boundaries, and guidelines for how they want to be in relationships. In fact, they must, in order to have healthy BDSM dynamics. You must.”

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Sexsmith notes that since you’ve already decided to keep seeing him for now, reframing might be helpful. They recommend Betty Martin’s work on the “wheel of consent” and her new book, The Art of Receiving and Giving. They also recommend The Pleasure’s All Mine, a memoir by professional submissive Joan Kelly that examines submissive community. Sexsmith also recommends exploring support groups and discussion groups for submissives, many of which are online during the pandemic. “If you can, make some submissive friends that you can talk this through with, deeply, who will get to know you and hear more of the nuance than I can,” Sexsmith says.

“Most importantly, get very clear on what it is you are getting out of this relationship. Have a serious check-in with yourself as to whether that is enough, or whether you are slowly, softly, building up resentment that he isn’t giving more,” they say. “You get to have needs, and boundaries. If it isn’t enough, that might be hard and sad, but it’s OK, and you will be deeply supporting your own self-trust, self-worth, and self-awareness if you can admit it and act from that place of unwavering strength.”

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Dear How to Do It,

I am a woman in my mid- to late-20s. I was put on hormonal birth control when I started my cycle because of medical issues, and I have been on it consistently until recently. I had assumed I was asexual in my teens and early 20s because I really didn’t think much about sex, and I thought that meant dating was off the table. However, now that I am no longer on the pill, I realize that is not the case. I have a newfound libido. As much as I would like to find a boyfriend, I have no experience. I wouldn’t even know how to bring up to someone my lack of experience. Where do you even meet someone without using apps? Is it possible to date responsibly during the pandemic? I moved right before the pandemic, and I don’t have any friends who can help me out. That being said, I’ve never had trouble making friends, and guys did ask me out on a regular basis before, so I’m not completely socially inept, just horribly inexperienced. I’m feeling pretty anxious and insecure, but I really would like to put myself out there. Do you have any advice?

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—Late to the Game

Dear Late,

We’ve heard in these pages from people much older than you who are just now embarking on exploration of sexuality. And we’ve heard from people who’ve been married for decades and are just now working on enjoying sex. You’re fashionably late, if not right on time.

Even if it weren’t for the pandemic, I think masturbation is the first step. Get to know your body so you can tell your future lovers what you like. While sex absolutely can happen without verbal communication, I’m of the opinion that it’s much better when we can talk about what we want and what makes us feel good. So gather some data, learn what you’re into, and figure out how to articulate it.

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Conveying your level of experience to potential dates can be delicate. You want to state the facts as neutrally as possible, something like “I’m starting to explore sexuality,” or “I’m newly curious about dating. It wasn’t a priority until recently.” Sharing your emotions can be risky, but it can also be rewarding: “I’m nervous about [whatever specific you feel comfortable sharing]” can open more doors than it may close.

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You specifically ask how to meet people without using apps, but I’d like you to reconsider them as a way to practice potentially romantic interactions while we wait for it to be reasonably safe to share air with lots of new people. And, who knows, you might meet someone interesting that way who you can establish trust with and then feel comfortable seeing in person with appropriate COVID mitigation or once COVID is under control. I imagine it’s currently just as hard to meet new friends in your new home as it is to meet potential mates.

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If you decide to go the apps route, be careful about the information you give out. You’ll want to keep interactions to the app until you know the person well enough to judge whether it’s a good idea to give them your phone number. Keep your last name, place of business, and specific neighborhood to yourself. And choose your app wisely—Tinder probably isn’t the place for you, but OkCupid, Hinge, or Feeld might be a good fit. Good luck.

Read how Danny M. Lavery responded to this letter writer in Dear Prudence.

Dear How to Do It,

I have a kind of stupid question. How do you know when you’ve had an orgasm? I’m a 20-year-old female in my first relationship (21 and nonbinary), and I’ve been experiencing something I think is an orgasm. It happens very specifically when we are grinding at a certain angle. It’s a rising pleasant feeling, and I lose focus on anything else. I wouldn’t describe it as necessarily having a peak, though, which is how everything I’ve read describes an orgasm. It’s something that feels like nothing I’ve ever experienced, grows, stays steady, and then fades. It doesn’t happen if I’m in the wrong head space or from anything other than this specific stimulation. For context, I’ve tried masturbating before but have never gotten anywhere close to this sensation. That’s an orgasm, right? Or am I just getting to the edge of one for some reason? Why am I not sure?

—I Think I Had My First Orgasm

Dear Orgasm,

Your question is not stupid, kind of stupid, or even a little stupid. A rising pleasant feeling, combined with a shift in focus, seems to fit Kinsey’s definition of orgasm. You don’t report the pelvic contractions I think of when I hear the word orgasm, but they’re more of a “usual” occurrence than “definitely.”

Whatever is happening to you, it sounds pretty awesome. And I think you should keep doing it.

In my experience, orgasms are less of a binary did/didn’t and more of a range—yes, for a single person, even during a single sexual act. Sometimes they’re very intense, with muscle contractions that shake the entire body. Sometimes fluid is expelled. Sometimes your toes actually curl. Sometimes they’re very mild, like the difference between a waterfall and a kitchen faucet.

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Keep doing what you’re doing, experiment to find even more ways to make your body feel good, and try focus on the enjoyment you’re having in the present. You might find that bringing yourself to that pleasant place more than once in a session changes or deepens the sensations you’re feeling. Good luck.

—Stoya

More How to Do It

In the past, I never really had anal sex, not because I was against it but because it seemed like something that took a lot of prep that I didn’t understand, and I was happy without it. Lately, I’ve taken it up in a concentrated way—I tend to be a little bit of a project manager when I try something new, sexually or otherwise—and I really like it. It’s been a revelation in a lot of ways. But what I hate is the prep work. Douching is, generally, a struggle: often a long process that, by the time I’m done, makes me want to stick nothing up there at all. I’ve learned that towels are my friends, and most guys are very understanding about it, but I find myself wondering if anal sex is just frequently messy and I should accept that or if I could be doing something better. Tell me the secrets.

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