How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!
Like most sexually healthy couples, my boyfriend and I consume pornography. But I’m worried about the sorts of stuff my boyfriend likes. He prefers pornographic games to videos or pictures; he says they’re “more interactive.” I haven’t gone through his porn game folder or anything, but every time I glance over to him playing the stuff, it’s always the same basic setup. He plays some sort of male self-insert character who goes out and acquires a harem of sexually submissive female characters who are willing to gradually be corrupted into accepting a wide variety of sexual demands from his character.
This development worries me. I know that we’re supposed to separate our fantasy life from our in-the-flesh life, but this definitely seems telling. He seems to view women as sex objects, and disposable ones at that, or ones to be hoarded. When I bring it up with him, he gets really defensive and gives the same line about it just being a fantasy. I worry that he’s trying to manipulate me to cover up a deeper problem. Should I dump him for this?
— Game Over
Dear Game Over,
I wouldn’t. He’s being open and sharing his desires with you at the risk of your judgement and … you’re judging him. Your concerns are understandable and maybe even fair, but unless you are noticing him attempting to coerce you into an actual harem-slash-life of submission, you could really chalk this up to fantasy play, as he suggests. A defensive reaction to the confrontation you describe could mean that he has something to hide, but it could also mean that he feels unfairly criticized for what he sees as an innocent diversion. Look, I understand when people (especially women) are not willing to give men the benefit of the doubt, and you’re under no obligation to do so. But I’m not sure that your boyfriend sees all women as disposable sex objects to be hoarded—more likely is that he sees the characters in the game this way and, indeed, disposable sex objects is what they exist to be. My recommendation is to see how things play out: If, in his treatment of you, he gives you even a slight indication that his attitudes toward real-life sex are reflected in the gamified variety he enjoys, it’s probably time to reconsider the relationship. If this outlook remains siloed, it’s not enough cause to terminate the relationship—unless of course you just aren’t feeling it or otherwise want to.
You have every right to exit a relationship, even if your rationale is thin and your evidence scant.
Dear How to Do It,
I’m newly separated, soon to be divorced. So, this is my conundrum: When I get back into the dating scene and start sleeping with other men, what’s the best avoid being “pumped and dumped” or becoming a “one-night stand”? Of course, the usual piece of advice tends to be “don’t do it too soon,” but also “don’t hold it way too much either.” When I was dating, I usually went with the flow, and it turned out this was a very “hit or miss” thing. Waiting or not did not really make a difference in regards to how further the relationship progressed. However, my bigger worry is the following: Regarding overall sexual technique, what exactly does a man like to see from a woman the first time he has sex with her? Should I be more passive, more “aggressive”… what is preferred? Also, what positions do most men like when they’re with a new woman?
I haven’t done this in way over a decade, and I’m so lost. What’s the best course of action for this?
— Old Beginner
Dear Old Beginner,
Unfortunately, many of the old rules still apply. When you put yourself out there with the vulnerability that sex requires, you may end up unappreciated and used. More important than any hard and fast rules about the amount of dates you should go on before hopping in bed, I think, is building a strong connection with a potential partner. You’re less likely to be discarded if he sees you as a sensitive human being, as opposed to something to have sex with. This is not a foolproof strategy and indeed you may experience a rift after sex, but the best you can do is impress upon someone how bad that would make you feel and attempt to get to know him well enough to be able to discern whether he’s the kind of guy who’s just looking for sex or actually wants a partner.
On the positive side, apps provide more of an opportunity to negotiate all sorts of things before meeting someone, including the kind of sex you’re interested in having. What a man likes to see in a woman, what positions he’s interested in, and whether he’s dom or sub or some of both is entirely subjective—I can’t paint this advice with a broad brush, I can only encourage you to have these conversations ahead of time. (That said, if I’m your sub and you’re forcing guidance out of me, I’m telling you that a lot of men love submitting and that doggy style is as sure of a bet as it gets.)
Also, and maybe most importantly, please don’t let yourself get lost in the shuffle here. Accommodation is an extremely attractive trait in a partner, but remember that this sex is for you, too. What do you like to see from a man? What positions are you willing to try? Would aggression or passivity be more of an accurate expression of your sexuality? Many potential partners will want someone who, above all else, knows what she wants. Figure that out first and proceed from there. As you present it, all of this stuff may or may not be happening to you—your challenge is going to be understanding the agency you have and going after the pleasure that you want. Good luck!
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Dear How to Do It,
Bi guy here, currently in my first actual relationship with another (also bi) guy. I’ve been with my boyfriend for a couple years. We’re both mid-30ish. I’m in love with him, extremely attracted to him, the relationship is great. About six months into our relationship, my boyfriend surprised me for a special occasion by having on some sexy tiny briefs when I undressed him for sex. It was the first even mildly kinky thing he’d ever done, and I loved him wearing something sexy for me just as much as I used to when my girlfriends did it. It prompted me to start buying him sexy underwear as gifts.
For a while I’d only gotten him men’s underwear/styles. My boyfriend is a masculine-presenting guy in normal life, so I always assumed he wouldn’t like feminine stuff by default. But increasingly he became very submissive during sex. He typically prefers being gently dominated in bed. We’ve also kept to strict top/bottom roles by his choice. He has never shown any interest in dressing as a female in regular life, and I wouldn’t want him to. He’s hot as a dude. The combo of him being a very confident, masculine-presenting guy in regular life, but very submissive in bed, has become 1000 percent my jam.
I then started having a persistent fantasy. I’d imagine undressing him to find him wearing panties. After being unable to stop fantasizing about it for a while, I did end up buying him some women’s panties along with some men’s stuff. His reaction was hard to read when he opened it, but a few weeks later he was wearing them when I undressed him. It was a huge turn-on. Then I started fantasizing about taking him out somewhere, with him basically having on outside male clothing, but underneath silk panties, lacy stockings, a whole get-up. He bemusedly indulged me in that, too, when I got up the nerve to tell him about my fantasy. Yes, I know I am lucky.
I’m now wondering if this is the kind of thing that’s typically going to keep developing? I think I would not find this sort of partial cross-dressing appealing as a look on most guys, but with my boyfriend’s body type (lean-fit, leggy, naturally smooth) it’s hot. He mostly seems to find my obsession with having him wear female underthings funny, and clearly is amused at knowing how hot he can get me when he indulges my kinks. Honestly, there’s sometimes a fair amount of laughing at me when I’m undressing him, and he can tell I’m extra worked up. It’s fine. We aren’t doing some hardcore BDSM stuff or anything. I enjoy that we can laugh with each other during sex.
The weird thing is, I feel no desire to have him present feminine except in this very specific way (wearing female undergarments under outwardly male clothes). I don’t find the thought of him in full female dress appealing, and in fact I think that would be a turn-off. So what the heck do you think is going on with me? Is a partial cross-dressing kink a thing? Or do I just have a weird clothing kink, because I also just really enjoy undressing him, including from whatever masculine clothing he’s wearing? And the fiddlier the clothes are, the more I like it, honestly. I’ve lately even bought him clothes primarily for how much fun I think they will be to take them off …
— Panties Please
Dear Panties Please,
“Partial cross-dressing” is one way to put it. Another is that you’re into women’s underwear, which is something a lot of people across genders are into. Your kink is specifically yours, but you have quite a bit in common with a lot of people who dig underwear. That a kind of gender presentation mix-and-match is turning you on isn’t so surprising because you are bisexual, and open to all sorts of things in, apparently, a range of configurations. You are open to, and—would you look at that?—blessed with abundance. You know it, but I’ll repeat it: Lucky you.
If you were previously into sexy underwear on women, well, why shouldn’t you be into them on men? Besides, sometimes a feminine article of clothing can enhance masculinity because of the clear comfort in oneself (vis-a-vis societal expectations) required to wear such a thing. This is why my boyfriend, who has a thing for underwear, prefers thongs over jock straps. .
It is, in fact, the contrast between the societal idea of “what men wear” and what your man is wearing that could be stimulating your interest. Many people like their sex naughty, and I’ve seen people repeatedly describe erotic interests across fetishes (from a fart fetish to a crying one) as deriving from this breach in societal standards. “Maybe it’s not so much the underwear but it’s the idea that he’s doing something ‘forbidden,’ and what makes it so forbidden is that he’s presenting as masculine in women’s underwear,” my boyfriend said when I read him your question.
You say you don’t have a desire for him to present as feminine, so it seems like maybe you’ve found the thing you’re into and it won’t develop further. But I can’t predict the future, especially for people that I’ve only met in paragraphs, so I’d say what’s more important than what will happen is just staying open. As long as you and your boyfriend are having fun, why shouldn’t this go elsewhere? A shared sex life often needs some sense of forward motion or the people involved get bored. I hope that you are as open to scratching your boyfriend’s itch as he is yours, and I’d recommend checking in with him to make sure that you aren’t taxing him with your requests. It sounds great, but you don’t want to make your desires into some kind of burden by continually thrusting them to the forefront of your sex life at the expense of his. As for the undressing thing, so many people are into this that it rarely gets even labeled as kink—it’s just part of people’s ritual, even when the ensuing sex is vanilla. I see no issues here, only exploration and open communication. Nice job. You found a keeper.
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Dear How to Do It,
I’m pretty sure my 15-year-old is gay. I have seen (and said nothing about) skirts and a dildo hiding in his room, among other things. We live in southern redneck central. What do I do?
— Worried
Dear Worried,
You keep loving him like you did before you discovered these items, which, by the way, are not necessarily indicative of his sexuality, at least not to the degree of specificity that you suggest. Plenty of straight guys wear skirts and play with dildos—they may be more kinky or adventurous than many expect when they think of a straight guy’s sexuality, but their interests remain fixed on women. Of course, your son may be gay as you suspect (parents often have a sense of these things), but there is simply not enough evidence to say so definitively. I’d refrain from approaching your son with inferences blazing, but you may want to do some boning up on your own in the event that he does come out—PFLAG has a mountain of resources for allies (here’s a toolkit for supporting a loved one’s coming out, and here’s a list of suggested coming-out themed reading, for both allies and queer people).
It can be hard to support kids if they’re squeamish when it comes to discussing sex—you don’t want to come at him so hard that it scares him away. Instead, let him know that if there is anything he wants to talk about with you regarding sex or sexuality, you’re there for him (ideally after you’ve done some of the suggested reading/self-teaching). The South isn’t known for being particularly hospitable to queer people, but there is community out there, and there are certainly large online forums in which he could insinuate himself, if he hasn’t already. Let him lead, knowing that he has your support and ear. If your surrounding environment is inhospitable, it makes it that much more important that home is a place of love and affirmation. It’s your job as a parent to make this so, and that is well within your power as an adult. So do it.
— Rich
More How to Do It
I’m a heterosexual woman who’s been dating my first boyfriend for a few months now. I enjoy being physically intimate with him, but I’ve only ever been able to orgasm in his presence a couple of times—and those times were only because we brought in my vibrator. Penetrative intercourse and fingering feel nice, but never take me over the edge. He performs oral sex on me occasionally, and I’ve inched toward orgasm when he does that, but he tends not to do it for long or with regularity. Meanwhile, he manages to orgasm every time and doesn’t seem concerned if I don’t. And sex always ends for us whenever he finishes. I know this is an unfortunately common problem for heterosexual women, but I’d really like to figure out how to bridge the orgasm gap here and make every time 100 percent satisfying for both of us. How can I communicate this to my boyfriend and steer him in the right direction toward what actually satisfies me?
