How to Do It

I’ve Always Preferred Tall Men for Sex for a Simple Reason. Now I Have a Dilemma.

A woman looking down at a shorter man.
Photo illustration by Slate. Photos by Diane39/iStock/Getty Images Plus and PeopleImages/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 a woman in my late 30s, and I am taller than average for a woman (5’10 or so). I have always gravitated toward men as tall or taller than me. There are several elements at play here, one being that I enjoy the stereotypical masculine/feminine dynamic of being protected and sexually tossed around by a big strong guy. Second, I really struggle to figure out the physical mechanics of how it would work to have sex with someone a head or more shorter than me. How do I ride someone I outsize in weight and stature? How does a short guy ride me if his head doesn’t come higher than my chest? How can we do doggy style if he can’t reach me on his knees (I can’t help but imagine a chihuahua and great dane here)? I occasionally enjoy a good pounding and my limited imagination struggles with how a slight person can provide it.

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However: I am now being actively pursued by a very handsome and funny gentleman who is all of 5’3 and it has me really reconsidering my biases. Can you provide any advice for the sexual mechanics of a short guy and a tall girl?

—At His Level

Dear At His Level,

Let’s start with weight differences, since that’s the first thing you mention. Are you afraid of squishing your partner? Have a talk about it before you get too worried about this one. Some people like being squished. Relish it, even. In the event your potential partner does not like being squished, you can brace yourself on the mattress—one arm on either side of his head—or on the headboard or wall. If they do like being squished, you’re free to put your hands in the middle of their chest or on their shoulders. If you’re able to isolate your pelvis and lower back, you can also lean your chest onto theirs.

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As for him riding you, I don’t see much of a problem in missionary. If you’re into being kissed while you’re being pounded (an interesting juxtaposition) you’ll want to work on your own shoulder and upper back flexibility so you can curl upward towards his face and reach his mouth with yours. Bracing your elbows behind you on the bed will help support your upper torso. For doggy, you’ll need to get lower than you would with a taller guy. You might work on opening your hips. Yoga or simple stretching can help with that. Supported doggy, where your pelvis is on top of a couple of pillows, is another option. There’s a wide world of men under 5’10 out there, and also plenty of taller women who date them and make it work. I think you’ve got this.

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Dear How to Do It,

I am a divorced man in his late 30s. Navigating the dating sphere is horrible, and my marriage destroyed my confidence, particularly in the bedroom. As a young man, I was adventurous and up for and comfortable with anything, but after years of a sexless marriage with ever-shifting demands that ended in infidelity on her part, I feel like an emasculated husk. I just got out of a one-year post-divorce relationship that we ended in part because she was not attracted to my lack of confidence and felt I was not masculine enough. I am in therapy and working on codependency, but how do I get my confidence back? I feel like every woman I meet online wants to have some dominant, hyper-masculine dude. I am a well-endowed lover (based on the response when it is unveiled) with a zest for cunnilingus and a quick study who wants to please my partner; is this not enough? I’m not submissive, but rough sex feels performative and like being someone I’m not. I feel so emasculated by these last two relationships and therapy isn’t cutting it. What do I do? Having a big dick is great, but I feel like I no longer am qualified to use it.

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—Christian Grey Sucks

Dear Christian Grey Sucks,

A big dick, a “zest” for cunnlingus, and a desire to please your partners (when it’s the kind of pleasure you enjoy giving, anyway) is, it seems, not enough for the woman you’re meeting on dating sites. You might consider meeting women in different ways, instead of via a system where we order hookups like pizza delivery. Dating apps are great for some people, and you are clearly not one of them. If you do use them and sex is clearly going to happen, have a conversation—be clear that you’re vanilla, not particularly dominant, and like giving certain kinds of pleasure. Talk through compatibility. Put it on your profile, if it’s appropriate. Get ahead of the issue.

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But I’m not sure you should be dating or even hooking up right now. I know you’re hurting, but putting a woman you’re attracted to in the role of confidence-fixer, rather than working on your issues in therapy, is something men do with irritating frequency. Off the top of my head, I can think of three separate men who’ve literally asked me to fix them. Like we’re all walking around with, I don’t know, a consecrated chalice between our legs in addition to the whole structure of the clitoris and all the reproductive parts. This is for you to solve. Think back to what animated you when you were younger. Find ways other than women’s validation to feel masculine. And if therapy is, as you say, not cutting it, look for a different therapist.

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Dear How to Do It,

I am a bisexual woman who was raised in an environment where it was not an option to explore my sexuality. Think “lesbian is a bad word” and being excluded from attending health and sex-ed classes with a hefty dose of religious guilt. Fortunately, I have an amazing husband who accepts me and supports my exploration of my attraction to my women. I support exploring some of his fantasies too, and so to mutual benefit, we have recently been having threesomes with other women, and it’s been amazing, exciting, and freeing.

Here’s the problem. We’re trying to expand our circle of friends that are open and semi-open, as well as just surround ourselves with accepting and like-minded people, since both of us experienced religious shaming growing up. We download a few apps but the ones that cater to what we’re looking for seem to have fairly small/inactive user bases. Most recently, we tried visiting a couple of lifestyle clubs. Initially, we both felt welcomed and people were friendly, but as the night went on, we both started to feel out of place. Decompressing after the fact, I realized that what was bothering me was the utter lack of queerness (and honestly, racial diversity). I guess we realized that these clubs are really catering more toward partner swapping, which isn’t something either of us is open to at this point.

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Since we play together, I guess what we’re really looking for is a poly club. Do such things exist, and how do you find them? Being in a place that embraced only straight sexuality really put me in a regressed state of shame for a few days, and I want to avoid making the same mistake again.

—Clubbed

Dear Club,

That feeling when you think you’ve found your people and then it turns out you haven’t can be absolutely awful.

You might be in a bit of a tight spot. If you live in, say, New York City, there are clubs you can Google that attract oodles of queer, poly, and pansexual partygoers. One of my business partners, Sweetpea, runs a very diverse event called Kinky Friday in Minneapolis every month. I’m sure there are others in other cities. I’m also sure that the farther you get from the biggest cities in the bluest states, the harder it is to get enough people together to make a scene. So, assuming you don’t have easy access to the cutting edge, you’re likely left with swingers clubs (very heteronormative and usually very white) and queer parties (where people are likely to be suspicious of you and your husband looking all potentially heteronormative together).

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So what can you do? Find poly events that aren’t clubs. Join queer groups. Show up and treat people with kindness. Give them time to get to know you and your husband, and understand that they may be wary at first. Establish relationships, accept invitations to things, and start slowly building your own community. Good luck.

Dear How to Do It,

I’m a straight single gal in my 30s and I’m new to dating (so far I’ve only been in a couple long-term relationships). I’m realizing I might be bad at sex with a new partner. I’m shy and take awhile to fully open up to a new person, and with new sexual partners, I feel like I’m being too awkward and quiet. In established relationships I’ve enjoyed being a bit submissive and adventurous, with my partner taking the lead, but I don’t feel comfortable or confident communicating about sex to a new partner. How do I get past this hangup? Do I just suffer through it until I get more comfortable and we find our groove? Am I just being lazy?

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—Practice Makes Perfect?

Dear PMP,

You nailed it in your sign-off. You have to practice communication. It might be scary at first, or make you nervous, or otherwise uncomfortable. You’ll get better at it with time and experience. You will probably have to suffer through discomfort at first—that’s part of life, part of doing new things, and part of getting out of our comfort zone.

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Start small. What feels most comfortable to you? A moan of pleasure? A “please touch me here”? Maybe you practice these at home while you’re masturbating, or in a nonsexual context like looking in the mirror. How comfortable are you saying “slow down,” or even “stop” or “no”? If you struggle in those areas, focus there first, especially before you establish any dynamic of the other person taking the lead, or of you submitting.

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I do wonder if you’re holding yourself to expectations that are too high, especially when you ask if you’re being lazy at the end of your letter. Even if you’d been out there hooking up three times a week since puberty, you’d still encounter awkward moments, and you’d still be finding new skills to learn. You’re OK as you are, and as you practice communication, you’ll feel more comfortable navigating sex with new partners.

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I recently told a couple friends about a moment I had with my boyfriend, and they said I was “beyond ridiculous” and they would have gone nuclear on a significant other for what I did. I don’t think it was so bad! You tell me if I’m wrong.

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