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’m a fiftysomething straight woman. Throughout my dating life, I’ve had men comment on the “tightness” of my vagina over and over. I know that women will tell men that they’re big or well-endowed as a compliment, but do men do the same with women? Tell them that the fit is tight or snug, even if it’s not? I’ve recently started seeing someone new, and he constantly remarks on my “tightness.” I can’t ask my girlfriends about this because who is going to say that they are loose? And what defines loose, anyway? And what defines tightness? When I first started having sex, it took several sessions before my boyfriend was able to achieve full entry. Sex has never been painful since then, and I’ve also given birth. My doctor has never noted anything out of the ordinary during routine exams. I do Kegels regularly if that makes a difference, and I’ve had various sizes of penises over the years that fit comfortably. I’ve only turned down one, and that one was way too big (he was OK with that). Obviously, it’s not something that one can brag about, but what do men mean when they say this? I guess it’s a compliment—but is it, really?
—Gripping
Dear Gripping,
Tight and loose, like big and small, are relative. This strange thing happens when people go into sex mode where the universe begins to revolve entirely around their subjective experience. Porn becomes good or bad based on whether it’s exactly how the viewer wants things. Vaginas become tight or loose depending on how large and turgid the penis in question is.
Now, let’s remember that the vagina is an elastic tube of muscle that can stretch to accommodate a human infant. It seems like either this part got left out of sex ed for a while or was presented but not well retained. Another example of vaginal accommodation is fisting, and I can tell you from experience that the vaginal canal bounces right back as long as plenty of time and lube are involved. Frankly, when babies and fists are on the list of things that can pass through a vagina, I don’t understand how men ever think of their penises as all that large.
I suspect that your sexual partners are more expressing enjoyment than attempting to compliment you, although that can be a very fine line. Communication during sex is great, and that frequently takes the form of describing our sensory experiences—so wet, so hot, so thick, so tight. It’s a bit like how every dog is the goodest dog.
I wouldn’t be surprised if your girlfriends have similar experiences. And while Kegel exercises are great, there’s a whole rest of your pelvic floor to keep toned, so keep walking, doing situps, and other activities that work your lower abdomen.
Dear How to Do It,
My boyfriend and I (both mid-to-late 20s) are now living with family due to COVID-related personal and financial difficulties. Sex at either of our homes is out of the question for many reasons, which leaves us with the options of getting it on in a car or hotel room. Hotels are not an option for now, both because we don’t trust the places in our price range to sanitize adequately for comfort in the time of COVID and because most are still out of our price range for regular use. That leaves us with car sex.
We are following the usual protocol of going to isolated places and keeping it quick, especially when there’s still daylight. It’s a rural town with little traffic/police, so getting caught isn’t super likely. My main issue is that the sex itself is almost always one-sided because of the location and time constraints—we move to the backseat, he sits with me on top facing him, we make out and I grind on him until I feel he’s hard, and then I give him a blow job. He loves making me come when we’ve been able to have sex in an actual bed, but neither of us know how that would work in a car—I love receiving oral more than anything, but it takes me a while to get off and neither of us knows how that would work in such a tight space. Fingering is hit or miss for me, so that’s pretty much out. He suggested that I start riding him instead of giving him a blow job, but I have only been able to take him inside me when I’m relaxed, have come once or more, and have plenty of lube. Going straight from clothes-on grinding to insertion is a little terrifying, to be honest, and I think the best I could hope for would be “not in much pain.” Is there a solution for our growing orgasm gap?
—View From the Backseat
Dear View From the Backseat,
I know you’re making the best of a terrible situation, and you say you’re not likely to be caught, but I do need to point out that you could experience legal complications if you’re caught having sex in your car. Look up the laws in your area and make sure you aren’t near any schools, even though they aren’t in session.
Have you ever tried vibrators? In the past several years a few that credibly mimic oral sex have appeared on the market, along with others that cover the glans of the clitoris in a delightfully effective way. An orgasm from a vibrator might prepare you for penetrative sex. You might find that fingering is more hit and less miss if you’re warmed up by an orgasm from a vibrator first, too.
You can also experiment in the car. Take an hour or so—with your clothes on—to work out the spatial possibilities. Maybe you can put the front passenger seat down, have him lie across it, and get your vulva close enough to his face that he can eat you out. I don’t know your car or your bodies, so I can’t be more specific here. If one or the other of you is a math wizard, you might take measurements instead and work out the angles later with pen and paper.
As you’re trying various physical arrangements, you might find areas of your body that could use some stretching. Take note. You don’t have to take up yoga—another expense—but you can absolutely stretch those parts in your spare time at home, and may be able to achieve positions that previously felt unsustainable.
A note about lube before you go: You might want to bring a towel and some wet wipes on your car adventures so you can use as much lube as you want without worrying about cleanup or returning home sticky.
Dear How to Do It,
How can I learn how to have great sex and make a man feel good without a partner? For context, I am a 30-year-old woman who isn’t a virgin but feels insecure about my performance because I haven’t had a lot of sex over the years. I’m recently divorced, and my ex didn’t want to have that much sex throughout our seven years together (I can count exactly how many times we did it). I had a couple of one-night stands prior to him, but I just don’t know if my technique is any good, especially since I would like to start dating again eventually. I’ve read some things online about how to give good oral, how to hold and stroke a penis, but how can I practice before meeting anyone? How do I know I’m doing a good job and making him happy?
I know communication with a partner is key to learning what they like, but I don’t want to dive into why I’m terrible or don’t know how to have good sex—won’t it come across as strange? Will it reveal I was spineless and pathetic for so many years? Don’t men want confidence in a partner? I want to be confident and pleasure someone, but I don’t want to share this insecurity because certainly this will be a turn-off. I don’t want to be charming and then sideswipe the guy with, “Oh, btw, I really don’t know how to give good oral or touch you right because I haven’t had a lot of sex. So you will have to walk me through this.” I would like to go into a relation confident and self-assured I can perform well. I have a great personality and career, I take care of myself, and I’m responsible—but I’m bland in between the sheets. I don’t even have the benefit of saying I’m a virgin, which would explain why I’m so novice. I guess I could watch porn, but I again don’t know how to grade if my technique is good. Are there ways to practice solo? Like if you practice oral on a banana and break it, you’re doing a bad job? This sounds pathetic, doesn’t it?
—Rookie
Dear Rookie,
You’re putting a whole lot of unnecessary pressure on yourself, and your implication that your situation is pathetic concerns me. You seem to feel that your low level of hands-on experience is a failing, and I don’t think that’s actually the case. I’m curious about how your former husband treated you and spoke to you about sex—presuming the two of you discussed it at all. And when you describe yourself as spineless, I wonder what you’re referring to. It’s possible that you didn’t speak up for yourself about your own pleasure and desire—something conspicuously missing from your message.
No matter how sexually experienced a person might be, and how many various tricks we might have up our sleeves, we all start from scratch with every new partner. One man’s “that’s great” is another’s “too soft” or even “ouch, too hard.” Some love to have their balls tickled, others like them squeezed, and still more don’t want you to touch their testicles at all. Some like teeth, others are very sensitive to them. I’ve had lovers who wanted their penises literally bitten, lovers who want their balls full-on yanked, and lovers who prefer the slight warmth of breath blown across their genitals. The way you find out what they’re into is by asking.
There’s no need to go into the history of your sexual experience, although that level of transparency can be good too. You can simply ask “How do you like to be touched?” and go from there. Many people with loads of sexual experience ask this question. And you should be prepared to communicate your own tastes, whatever they may be.
As for how to learn those tricks I mentioned earlier, Nina Hartley and Jessica Drake both have sexually explicit education series. Please don’t try to use mainstream entertainment-driven pornography as a how-to guide. You can also look through databases of fan fiction and other erotic stories to get an idea of how people fantasize, and a window into their inner experiences.
Dildos and bananas can be useful for demonstration, but you’ll really need a flesh-and-blood phallus to practice on. This can be as simple as saying “I’ve been reading and want to try out a couple of blow job techniques. Do you mind letting me practice on you?” Again, no need to bring up your history until you’re ready to talk about it. Good luck.
Dear How to Do It,
My wife and I have been married for four years. I like to think I’m a good lover. She almost always comes first (and usually second, third, and fourth). I listen. Try to tune in with her. I ask her about her wants and needs and desires. Outside of the bedroom, I talk with her about sex so that in the bedroom we can be present. When the focus shifts to me in the bedroom, one of two things happen: She tells me to hurry up—or she cries.
I’ve clarified with her both in the moment and also outside the bedroom to make sure I am not hurting her in any way. She says she just gets emotional being close to me. I’ve left room for her to speak about anything that is bothering her. She insists she’s just emotional. Both of these scenarios take away from my experience, and I would like to handle them better. I don’t always want to hurry up and finish. Usually I do that for her. But sometimes after I’ve spent 30 minutes or way more focused on her, I want to just enjoy it without having to hurry. I’ve asked her about sometimes letting me be the focus first so that she is not as tired or “done.” But she said there’s an orgasm gap, and I just need to learn to deal with it. In general, there surely is an orgasm gap, but in our bedroom, there isn’t an orgasm gap for her. I work hard to make sure of that. And in the other situation when she cries, I stay very focused on her—I wish I could just let go, but when my partner is crying tears, it doesn’t feel like the best time to just let everything go.
There’s isn’t any in-between—she either wants me done, or she cries. I love caring for her. I love caring for her through sex. It’s beautiful. Sometimes, though, I just wanna penetrate her and not be confronted with “hurry up” or an emotional experience. I think it boils down to in either scenario that happens I don’t feel like she’s with me. She’s either ready to be done. Or she’s lost in her emotion. How can I move past this?
—Waterworks
Dear Waterworks,
How’s your communication in other areas? Is there transparency? Is there anything happening in your wife’s world that might be causing her to feel more emotional around sex? Has this pattern been relationship-long? If it started after the relationship, was it sudden or gradual? Can you think of anything that might’ve changed around the same time? How’s her body doing? Is there some physical reason she might want to wrap sex up quickly after a certain point?
I can think of a few reasons a person might feel weird continuing to have sex with someone who is crying, but—taking at her word that she’s just emotional—you might frame her tears as an expression of her care toward you and dig into what’s happening inside her. You might ask her what these emotions she feels are, and what thoughts are in her mind while they’re happening. The most obvious time to have this discussion is in the moment when the crying begins. Make it clear that you aren’t looking for something “wrong,” and that you are looking to understand her experience better.
If she’s content to leave things the way they are—once you’ve made it crystal clear that this is unsustainable for you—you might ask her to consider a sex-positive couples therapist. Having a trained professional in the room who can ask follow-up questions is incredibly useful. And it sounds like you can use all the help you can get untangling what’s going on here.
This could be a sign that the two of you aren’t sexually compatible, in which case you’ll have to make some choices about whether you want to stay in the relationship.
—Stoya
More How to Do It
My boyfriend masturbates constantly. I knew prior to the pandemic that he was very uptight about masturbating and felt a lot of shame about it. He has issues reaching orgasm, so often masturbating can take a long time. I’ve tried to gently encourage him that he shouldn’t feel shame, everyone masturbates, and it’s a normal and healthy thing to do. But now that we’ve been quarantining together for eight weeks, his masturbating is driving me INSANE, and I feel super resentful about it. Every afternoon, five days a week, he goes upstairs and locks himself in the bedroom and masturbates for three hours on our bed. He’s supposed to be working, and I know he’s had disciplinary problems at work. He has such a history of shame around masturbation as well that I feel like I can’t go upstairs during that time, or else risk freaking him out. So here I am, downstairs, sitting at my desk, feeling utterly resentful that he’s upstairs masturbating yet again.
