How to Do It

I’ve Had Sex With Many, Many Women—and I Suspect Everyone Is Wrong About One Thing in Particular

A man and woman in bed
Photo illustration by Slate. Photo by dima_sidelnikov/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 have read several times (most recently in L.V. Anderson’s article on Dan Savage) that most women are unable to have an orgasm via intercourse alone. I’m no sex expert, but I have had intercourse with lots of women, and this statement is so radically at odds with my experience that I have to ask myself whether: 1) most of my lovers have faked their orgasms (in which case they’ve been pretty good fakers); 2) I have been very lucky in finding women who orgasm from intercourse; or 3) the reporting I have read has been imprecise about what the studies say and whether the real point is simply that most women need clitoral stimulation to achieve orgasm. Any fool should know that unassisted doggie style is unlikely to get the job done. But cowgirl and missionary both offer good opportunities for clitoral stimulation (my wife calls it “grinding”), and it’s pretty simple if you just pay attention (focus on your pubis, boys, not so much on your penis!). While it has been many years since I have made love to a woman other than my wife, can women’s orgasms really have changed that much since I was single? What do the studies actually say on this issue?
—Want to Believe

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Dear Want,

You are correct. Many women and people with vulvas require stimulation of their clitoral glans to experience orgasm, and clitorial glans stimulation is not precluded by vaginal penetration. This is a small semantic snag regarding “intercourse” and “penetration”—colloquially, intercourse tends to get used to mean penis-in-vagina penetration, and penetration usually involves insertion of objects or a body part into another, but “intercourse” itself can mean all kinds of things. For what it’s worth, the studies are varied, but they largely confirm what you’ve figured out on increasing the likelihood of orgasms through “intercourse,” even if many are not clear on their definitions, either.

In the same way that I must translate “vagina” as “unknown, possibly referring to the entire set of sexual organs, possibly referring specifically to the vaginal canal,” you’ll do well to translate “intercourse” as “unknown, possibly referring to the whole set of sexual acts, possibly meaning only penetration.”

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Dear How to Do It,

My partner (a man) and I (a woman) have recently begun to look for others to engage in communicative, safe group sex with. We met one couple through an app and, after extensive texting, feel we’re a great match in every respect! Here’s my one hangup: We haven’t been able to meet up due to some schedule incompatibilities, but they text us a LOT. I’m talking multiple times a day, every day. This was fine at first, since we were still getting to know each other. Now, several weeks have passed, and I could really do without the “good morning” and “I’m thinking of you” texts from people I’m only interested in having a foursome with. (They are sweet, genuine, attractive people, but I don’t think we’re compatible as friends.) I have tried setting clear boundaries with them along the lines of, “I’m not sure I’m interested in developing a close relationship outside of sex,” which they responded kindly to. Still, their texting habits haven’t relented. Can you advise me on how to broach the topic of “Hi, I still want to sleep with you, but can we stop talking regularly until that actually happens?” I don’t want to come across as disinterested or harsh.

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—Good Morning

Dear GM,

Lead with the positive, emphasize what you are happy to text about, and set your boundary firmly. “I’m very much looking forward to a foursome with y’all, and am happy to communicate about potential scheduling. I’m also overwhelmed by the amount of messages you send.” Give them space to respond. They might apologize, they might express hurt, or they might get upset. Prepare yourself for multiple outcomes.

I’m curious whether this is foreplay for them, or whether they need more romantic sorts of interaction than you do, or if this is something they think they need to do to keep you interested. The most important question, though, is whether they continue to text you throughout the day after being told in no uncertain terms that it isn’t welcome. If a boundary feels like disinterest to them, that’s a sign they aren’t a good match.

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Dear How to Do It, 

I really like sexting and sending nudes, but I feel like I can’t trust people to receive them. For years, I’ve taken photographs of myself in various sexy poses and stored them in a secret album on my phone, and the thought of sending them to someone during the work day just really turns me on. But I’ve never even sent one. For most of my 20s, I’ve only dated casually—had lots of hot flings and only two short-term relationships (both with pretty possessive partners)—and I’ve only sent “disappearing” pics once using a privacy-oriented app. The entire time, I was so paranoid the other party was taking screenshots. Now, I’m chatting online with a really hot and sexy man that I’d totally love to bang. I think he feels the same,  but before we could meet, I had to fly across the country for the next few months for personal reasons. So I want to suggest sexting to Hot Guy, but I’m worried I can’t trust him to receive any pictures, even if they’re the disappearing type. I worry anybody that receives my nudes will try to share them with friends or save them to look at later (which I’m not OK with), even if we both establish our rules of sexting. I would feel horrible knowing any pics circulated. Sometimes I even feel guilty for not being in a longer-term relationship where I could fully trust my partner, and also feel safe to feel sexy. How do I establish trust to send my nudes, especially with a casual fling I haven’t even met in person? What are my options, besides hiding all my features and Snapchat?

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—Good Nudes

Dear Good,

First, you say you really like sending nudes, then you say you’ve never sent one, then you say you’re sent one once. So I’m not entirely sure what’s going on, but I’ll try to help.

You mention both of your relationships being with partners who you found possessive, and guilt surrounding not matching your ideal relationship situation. I think working on that is a higher priority than navigating the dodgy waters of sending saucy photos. Does a longer-term relationship mean you can give full trust? Is there a certain amount of time after which that person won’t go back on their word? I don’t think so, and I encourage you to consider these things. Also, where’s the guilt coming from? Do you believe that a long-term relationship is the ideal? Why do you believe that? Do you feel deficient for not being in one? Why do you want that? I’m not trying to imply that your desires are wrong in any way, but I do want you to think through them and gain a better understanding of yourself in this area by writing for 30 minutes or longer about these subjects, thinking on a walk or in the shower, or talking to a friend who you trust are all ways that people process their emotions and beliefs. Therapy is another option.

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There’s a whole range of ways to live life, from extremely defensive—never sending a nude, never telling a taxi driver your name, never letting your neighbors into your apartment—to extremely trusting. Balance is the key here, and finding yours will take time. Along the way, you’ll probably make mistakes. Since you seem very private about photos of your body, I’d wait until you’ve established enough in-person rapport that you feel safe.

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In case you do decide to proceed, you can set your camera app’s location tracking to fully off, and yes, you can absolutely hide your face and any identifying marks on your body. Disappearing apps do make it easier to prevent photos being saved or shared, but as you mention, they aren’t foolproof. Good luck.

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Dear How to Do It, 

I recently hooked up with a friend of my roommates who I was interested in, and knew was interested in me too, after we took MDMA together. I was too rough when doing it. I choked her, pinned her arms, and was overly aggressive in general, but I didn’t realize it at the time. I’ve only had sex with three other people and they all wanted me to be rough with them. I shouldn’t have, but I defaulted to what I knew because I was scared that I wouldn’t please or impress her. I didn’t realize that she was uncomfortable or in pain until she asked if we could stop. I immediately stopped when she said that, but the damage had been done, and she just rolled over and cried. I feel awful. I didn’t mean to hurt her, but I know I did and I’m not sure what I can do now. I’ve moved out of where I was living and left the social circles she’s involved in because I don’t want to make her healing process any harder, or make her have to relive that experience. I know this is unforgivable, and I can already confidently say I will never do anything like that ever again. I’ve never wanted to hurt her or anyone, but I don’t know what to do now that I have.

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—I Messed Up

Dear IMU,

I’m not sure that this is unforgivable. A real apology—what you did, the harm you caused, and what you’re going to do to repair the situation and make sure you don’t do it again—can go a long way. Especially when that apology omits excuses, avoids dwelling on intent, and does not minimize what happened. Apologizing is also vulnerable, in a way that people tend to be wary of in this situation—I suspect because a proper apology involves admitting guilt and the carceral justice system is rightly something that frightens people.

If you want to make an apology, you might ask your former roommate if they have a sense of whether their friend would be open to hearing one from you. If your former roommate thinks that’s a possibility, ask the woman you assaulted whether she is willing to speak with you. Center her consent—ask a direct question and then give her the chance to say yes or no—and, if she’s willing to talk, ask her how she wants to have this conversation. Ask her what she wants. She might prefer text message, a phone call, or a public place of her choosing. To be clear, if your former roommate says the woman you assaulted doesn’t want to hear from you, do not contact her.

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If you are allowed the chance to apologize, leave out the part about how previous lovers wanted rough sex and leave out the intent portion—”I didn’t mean to hurt.” Write out what you’re going to say beforehand. And be open to the possibility that she doesn’t forgive you, expresses anger, or otherwise shows you the ramifications of your actions.

Crucial, though, are the ways you’re going to make sure you never do this or anything similar again. When you say “I can already confidently say I will never do anything like that ever again,” I struggle to believe you. You’re not telling me how. Are you going to avoid sex while under the influence of drugs or alcohol? Are you going to ask people first before engaging in various sexual acts, and pay closer attention to your partner’s engagement? Will you look for nos and less-than-enthusiastic “going along with it”s? Are you going to find a course in unlearning rape culture and go through it in earnest? Read Jaclyn Friedman and Jessica Valenti’s Yes Means Yes? Start journaling? Get into therapy?  All of the above would be useful, and you can absolutely do more than one and come up with other actions yourself. If you aren’t on board with this part, any attempt at apologizing is empty.

More How to Do It

My wife and I, a man and woman in our 30s, have been married for almost two years. We live in a condo, and last month, my best friend, Max, got a new job in our expensive city across the country and came to stay with us while he looks for his own place. This arrangement has been nice because we have had no social lives for the past year-plus, thanks to COVID. But it’s also a little frustrating at times because he’s always around, and my wife and I have no alone time. I thought everything was fine—until what I caught my wife doing the other day.

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