How to Do It

Women Think I’m the Typical “Nice Guy.” They Have No Idea.

I’ve done my research.

Man wearing a t-shirt with a whip floating next to him.
Photo illustration/animation 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 am a young college student looking ahead into my future and one thing has been giving me a lot of anxiety. I am a really big nerd, hopeless romantic, and stereotypical “nice guy.” In addition, with respect to both romantic and sexual relationships, I have very little experience. But through my own exploration and “research” I have found that I am very kinky and want to incorporate BDSM into my future sex life.

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I am very dominant and enjoy things beyond what the layperson might casually try. At least right now sexual compatibility seems like an important factor in any long-term future relationship I want to have. What my anxiety comes from is the fact that I do not publicly present as someone who enjoys these things (5 feet and 7 inches, skinnier build, bookish/nerdy look, etc.), and my personality doesn’t reflect a very dominant person. I am worried that the women I end up dating won’t be as enthusiastic about BDSM as I am. What advice would you have for dispelling this anxiety and or attracting/finding women with aligned interests?

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—Book Judged By Its Cover

Dear Book Judged By Its Cover,

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I’d like you to know what you’re invoking when you use the phrase “Stereotypical ‘Nice Guy’”; guys who feel entitled to sexual attention from a specific kind of woman and react with something ranging from whining to assault when denied what they think they deserve. If that’s you, by all means, keep describing yourself as a “nice guy.” If what you mean is that you’re kind, respectful, or gentle, use those words instead. They’re more precise and less loaded.

BDSM is play, with some notable extreme lifestyle exceptions, and many people who practice power exchange are dominant in the bedroom or club while remaining functional humans in the other parts  of their lives. Think more Clark Kent/Superman than Bruce Wayne/Batman. The people I’ve met within the BDSM community tend toward higher education or heavy recreational reading, appreciation of entertainment genres like horror or sci-fi, and frequently have a tendency to apply their natural nerdiness to the subject of sex.

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Healthy BDSM runs on consent and communication. Even a hookup should have boundaries, discussion of desires, and explicit agreement from all parties. Otherwise, you may be harming someone or sexually assaulting them. Be prepared to give more detail about your desires than simple “dominance,” and be prepared for several women to say “no” before you connect with people whose interests mesh well with yours. Not to mention the other things that need to be in place, like mutual attraction.

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As for where to find women who are interested in BDSM, I suggest FetLife, OKCupid, and Feeld. Each platform in that list attracts a kinkier than average user base and has a culture of putting sexual desires to the forefront of profiles. BDSM or kink events in your area are also a good place to meet potential lovers. Wherever you’re meeting people who might become partners, you’ll probably encounter some who reject you because of your height or build. That’s the dating process. The good news is that rejection helps you practice being turned down, which can take some of the power away from anxiety over the possibility of rejection. Remember that this isn’t a judgment of you as a person and move on. If you find yourself getting exhausted, take a break from dating. I think you’ve got this.

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Dear How to Do It,

I’m a straight man in a don’t-ask-don’t-tell open relationship. I’ve been thinking about visiting a sex worker while I’m on a trip, but the monkeypox outbreak has me wary. I certainly don’t want to give my primary partner an unwanted present that would prevent her from working for three weeks. What’s the risk level? Should I wait until vaccines are available?

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—Don’t Make a Monkey Out of Me

Dear Don’t Make a Monkey,

Much like the early days of COVID, the United States is struggling to connect people who need monkeypox tests with actual tests. So we can’t really say how prevalent monkeypox is in the general population.

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We do know that monkeypox primarily spreads through skin-to-skin contact.

We also know that men who have sex with men (MSM) currently make up the majority of known monkeypox infections in the U.S. Eric Toner, MD, who works at the Johns Hopkins Center for Health Security and is an expert in bioterrorism and emerging infectious diseases, pointed out that one of the reasons for this may be that MSM may be more likely to notice a rash than other populations, due to routine self-inspection for signs of diseases that spread through sexual contact, like syphilis.

Do you have these same qualms about sexual interaction with a healthcare worker? Without your tone of voice or more context, I’m left with the—potentially uncharitable—possibility that you might be thinking that sex workers of any gender are dirty and diseased. If that’s how you think, please, don’t subject a sex worker—a human doing their job—to your stigmatic beliefs. If a sex worker gets monkeypox, they are—much like your partner would be—out of work for several weeks. Direct providers of sexual services are motivated to visually screen clients for signs of illness. There’s a risk involved with physical contact with others, which includes sexual interaction. That’s yours to weigh. The Centers for Disease Control and Prevention (CDC) provides additional information you can read.

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But vaccination may never be in the cards for you. “It is very unlikely that we would do widespread vaccination. Even during the smallpox eradication program in the ’60s and ’70s, we rarely did mass vaccination. What we did was ring vaccination—that is, we vaccinated those people who had direct contact with a known case. That’s how smallpox was eradicated,” Dr. Toner said.

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Dear How to Do It,

My boyfriend and I got intimate extremely quickly in our relationship, but have always had very good communication between ourselves regarding not only our emotions but our sex life. From the beginning, he has always left me completely satisfied very quickly, occasionally getting me to orgasm three times in one sitting. The problem is I have never been able to make him cum.

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He claims that he doesn’t care as long as I am happy and satisfied, but he always brings up the fact he has never cum every time we collect ourselves afterward. I feel absolutely terrible. I have tried to give him blow jobs, but I have past trauma that prevents me from doing it for more than a couple of minutes, and he has been completely understanding once I told him. I’m also simply not good due to a lack of practice. I also have tried giving him handjobs, but he has a certain way he likes to do it (fast and hard) and I end up frustrated and flustered and we usually move to something else every time.

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I understand that for guys, ejaculation can be very intimate, and having a set way for a long time can make it hard for them to cum with someone other than their hand, but I want him to feel the same pleasure he makes me feel. Please help.

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—Confused

Dear Confused,

Ejaculation is very intimate for some men, not intimate at all for others, and somewhere in between for most. Anyone who masturbates the same way every time might habituate themselves to a very specific kind of stimulation and struggle to orgasm without that.

I think you should deal with this disconnect between what he says about not caring about his orgasm, and what he says about not having orgasmed, first. Spend some time reminiscing about times he’s said he doesn’t care, and times he’s acted like he does care. Make note of what you’re curious about and come up with some questions. I might ask a partner if they’ve noticed that they bring up the fact that they didn’t orgasm after every sexual interaction, and go from there based on their response. You’ll want to phrase things in your own words, and ask about the specific areas you want clarity in.

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Set yourself up for success by making sure you’ve got plenty of time to talk without interruption, choosing a time when both of you are as calm as possible and your biological needs are taken care of, and arranging the room to be reasonably comfortable. Listen to what he says, and ask follow up questions as appropriate.

If you’re comfortable with him ejaculating in your mouth, he can get himself close to orgasm with his hand and then you can lick the head of his penis until he comes. And you can work on your handjob stamina by doing exercises that strengthen your biceps, forearms, and hands, like push-ups or lifting a two-pound barbell with your wrist. Good luck.

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Dear How to Do It,

I do not fit inside my girlfriend. It’s giving her dysphoria and frustrating both of us. I’ve been fortunate to have larger than average parts, but it’s never been a problem before with other partners.

I (cis male) have been in a great relationship with a transgender woman for some time now. Communication and desiring each other are not the problem—I just don’t fit when we attempt penetrative anal sex (with precautions/preparation/plugs/etc). It’s giving her dysphoria and frustrating both of us. I’ve been fortunate to have larger than average parts, but it’s never been a problem before with other partners.

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She often wants penetrative sex when things get steamy and vocalizes that. We’ve tried ohnuts, plugs, and every lube to get the cargo into the container but every attempt leaves us both disappointed and triggers her dysphoria. She has told me about how frustrated she gets when it doesn’t fit and how much she wants penetrative sex in those moments. She’s also described how she’s brought it up in therapy and the feedback her therapist gave was “you need SRS badly.”

I’m used to only climaxing during penetrative sex and I have been trying to challenge my old sexual scripts about what sex “is” and review what my sexual needs are to adapt to the size constraints. We’ve explored a few other modalities together and while that has been wonderful, nothing has been scratching the same itch like penetrative sex has previously. It’s been a slowly building frustration for me and recently I have started to be tempted to cheat. I’d rather not replace sexual frustration with guilt.

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Despite our best efforts at communication and adaptation, I just don’t fit and it’s a problem. Is there something I’m not considering or overlooking?

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—Square Peg Round Hole

Dear Square,

Your girlfriend might prepare for anal sex by using increasingly large plugs to stretch herself out before the two of you begin sex, or you might incorporate stretching with plugs into your interaction. Find a size that she can comfortably accommodate without being turned on, start with that, and go slowly up in size as her anal area adjusts. It’s possible that she simply has a maximum limit on the dimensions she can accommodate, but I think it’s worth trying.

I worry that any discussion of opening up at this stage will feel like another proof of inadequacy on her part, and that’s counterproductive to any goal of preserving her feelings. If it’s possible to present this as a two-sided opportunity—you can penetrate people until you climax, she can be successfully penetrated, you might have some success. It’s a high risk move, though, and that’s your decision to make.

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You might simply not be a match. Sometimes we don’t match with people because our sexual interests don’t overlap enough, sometimes because our political or spiritual beliefs are at odds with each other, and other times because our parts literally don’t line up. It happens, it’s often tough to realize, and it doesn’t make either of you bad people or bad sexual partners. Whether the two of you want to stay in a relationship with a sexual mismatch of this sort is up to y’all, and making a decision might require some hard conversations. Lead with your care and regard, and be as kind as you can.

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—Stoya

More Advice From Slate

How common is amazing, long-lasting chemistry? I mean the kind where you smell his T-shirt and lose your mind. I know the standard answer is that it’s infatuation, wears off in a couple of months, etc. But my husband and I have this, and it’s been 30 years. Seriously, I bury my face in his chest, get a good whiff, and it’s ON. Now our kids are adults, we’re having serious conversations about long-term relationships, and I wonder: Should I tell them to hold out for this kind of chemistry?

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