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,
My boyfriend has told me on multiple occasions he is pretty “vanilla” when it comes to sex. I am not. However, I don’t consider myself too kinky. Even still, sex between us is pleasurable. Recently, he and I were discussing another couple we know that has been using erection-enhancing pills and a male “stroker” toy to enhance their sex life. My boyfriend said they were “doing too much,” all that is not necessary, and joked about the guy not being able to get it up.
Fast forward a week or so, I’m staying at his place and notice he’s got cock rings/ ball stretchers, urethral-sounding wands, a stroker, and erection pills. All of which he’s obviously using, and not with me. I do suspect he takes the pills when we are together sexually. I’m not upset about him pleasuring himself, but I am upset that he was not honest with me and pretends to be “vanilla” when he’s not. “Vanilla” has honestly left me feeling unsatisfied with our sex life. Also, I don’t think some of these practices (urethral play) are healthy and I’m not willing to participate. It’s too much for me. He also has a hard time reaching orgasm sometimes. Could this be because regular sex isn’t as exciting as his kinky self acts?
Now I feel like he is a liar and untrustworthy. For me, it’s hurting our connection and our sex life. How do I approach him to discuss this matter? Keep in mind I was poking around without permission when I saw a couple of the items.
—Unsure and Unsatisfied
Dear Unsure,
It’s understandable that you feel like you’ve been lied to after making your discovery. You could just pack it up right there, and decide that there’s no room for a liar in your future. But, if you want to proceed, which it seems like you do at least discursively, you could come equipped with compassion. It seems pretty obvious to me that your boyfriend was trying to deflect his own shame when he shamed that other couple’s use of a stroker and boner pills. Not all lies are constructed with the same structural integrity, and it sounds like he has issues regarding the acceptance of his own proclivities and what he might regard as a shortcoming (by that I’m referring to his lack of erections on demand, without chemical assistance). Yes, it would have been ideal if he hadn’t made other people out to be somehow aberrant for enjoying the same things that he does, but unfortunately, the road to self-acceptance can be long and winding. That people perceived as male from a young age are typically socialized to withhold emotional expression only makes for more needless roundabouts and dead ends.
There’s also a semantic element to your qualm—I think most of what you found in his stash still exists within the reasonable boundaries of “vanilla” for most, by and large. The only element that strikes me as perhaps constituting kink is the sounding wands, which you want no part of anyway. The other stuff I think qualifies as enhancers, and if what is being enhanced is vanilla sex, they aren’t necessarily elements of kink. Again, one could argue differently (I’m always here for a challenging opinion), but what I mean to illustrate here is that because definitions in this realm are nebulous and range from person to person, he hasn’t necessarily given you a fraudulent identification. This is all subjective—perhaps he doesn’t consider what occurs during solo sex as qualifying for kink. I understand your wariness of his claims after he misrepresented himself, but nonetheless, he may feel in his heart of hearts that he’s vanilla. (Also, while sounding does come with health risks, it can be performed safely—that he’s using wands made for sounding and not, like, miniature-golf pencils, is a good sign.)
All of that said, it is understandable that you now feel a fissure. Being on the same page about this stuff is the goal. If you want to get there, though, given the signs of shame he’s exhibiting, you must tread lightly or not at all. If you bring this up, he may feel that you’ve violated his privacy and, consequently, shut down emotionally. A pure statement of fact here may be too much for him, and even a good-faith inquiry could torpedo things. If I wanted to rebuild in your situation, I’d invert the discussion—don’t accuse him, but say that you’re interested in adding some of those enhancements. Show him that you already accept what he’s into without letting on that you know what he’s into. Tell him you’re curious about what it would be like if he wore a cock ring or ball stretcher. Refer back to your conversation about the other couple and say, “That talk got me really curious about boner pills. Why don’t you pop one and we’ll see how it goes?” The idea here is to mitigate his shame by showing him that you already accept him. After all, you do accept him, right?
Dear How to Do It,
I’m a straight, cis woman. I hang out in a lot of circles that, for whatever reason, have skewed queer, and have thus thought long and hard about whether I am attracted to other women. The answer is that I don’t find myself sexually or romantically aroused by them, though they are often quite aesthetically pleasing. I am, on the other hand, very attracted to men. I am in my mid-late 20s and have never had sex. I’d like to get it over with at this point, however, I’m quite nervous about the mechanics of intimacy; I have never even kissed another person. I very much do not want to be a poor sexual partner. Since hiring a professional is illegal here, I thought it might be a good idea to get into casual dating/hook-ups to see if I could find someone(s) to fool around with to get some practice without worrying as much.
My dilemma is this: I feel like I would be a lot more comfortable trying this with women rather than men. I don’t know a lot of men and am nervous around them. I do know a lot of women and feel more comfortable around them. I also know the parts of a cis woman a lot better than those of a cis man. I am a tactile person, so regardless of attraction, I think it might be fun to squish some boobs or feel someone up. I don’t want anyone to feel devalued, but my scheme to get experience is experimental in nature and likely to insult, right? I’m also not exactly sure how I would advertise myself on dating apps. Is there any way to proceed ethically here, or should I just drop it?
—Unethical Non-slut
Dear Non-slut,
Just drop it and…then what? Not have sex? Just brick up that door so you have something nice and hard to hit your head up against when you’re really horny? Please. You’ve come to the wrong place if that’s what you want to hear.
I can’t fault your logic for wanting to play with a woman, but keep in mind that initiating with someone that you aren’t attracted to is a good way to have bad sex. It might be less intimidating to start with a woman, but then there’s the small matter of continuing the sex you just initiated. There’s more to sex than starting sex.
I have to wonder if you’re more attracted to women than you’re comfortable letting on or even realize at this point. We can define “attraction” in many ways; one of them is whom we’re comfortable around enough to have sex. But if the premise of your letter is in fact concordant with what’s actually going on with you, I don’t see anything wrong with experimentation as long as you’re upfront about it. There will be people who may refrain because they find the very premise offensive, but there will likely be others who think showing you the ropes is hot. I think you have to just explain yourself thoroughly and prepare yourself for rejection. It’s part of life and should be no big deal. Anyone who makes it a big deal by carrying on and acting so wounded because of your request is not really worth holding onto anyway. Let them filter themselves out. On apps, you can label yourself as inexperienced but eager. That will allow those who find that notion distasteful to move on, and those who are turned on by it to state so upfront. You’ll be better off pairing up with partners who communicate clearly, signal that they understand where you are with sex and what you’re interested in trying, and explicitly allow you to set the pace. You’ve waited this long, you can wait a little longer until it’s right.
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Dear How to Do It,
I’m a (mostly?) straight cis guy who is just getting into bottoming and being submissive, and I’m honestly overwhelmed with all the possibilities. Part of me feels like a virgin all over again. What advice do you have for a complete newcomer (pun intended)?
If the context is helpful, I’ve been fingered and had a vibrator used down there and it felt amazing, but I can only manage anything going in there when I’m super relaxed, which I can usually ensure by taking CBD. I also often have gastrointestinal issues, but I usually have sufficient warning and wouldn’t let anyone near there during such episodes.
What toys are good for the ass? What toys are bad? How do I work my way up to being pegged? Will I be able to have multiple orgasms? What positions are helpful for novices? How do I ensure this is relatively safe (in terms of infection, damage to my anus, and anything else)? I have a really hairy ass, is that a problem? What am I not even thinking about but need to be?
—Started at the Top and Now We’re Here
Dear Started at the Top,
First, the very basics: Go slow, use lots of lube, and start small. I’ve heard anecdotally about people who can take massive dicks on the first go, but they seem more like anatomical marvels than models of anal possibility. You already understand the most important principle of bottoming: relaxation. Sometimes it’s necessary to do so consciously, which may sound contradictory, but I think it’s about mindfulness—really focusing on letting go. If you push out (without straining) upon getting penetrated, you may find things go in more easily. There’s also the “butt clock” technique (coined by Dr. Carlton), which can assist in pre-play loosening (basically, a finger is inserted and held for a few seconds at the 12, 3, 6, and 9 o’clock positions, if you imagine your hole as a clock).
The best toys for your ass are whatever will work for you—anatomy ranges, so this will involve some trial and error. Since you enjoy having your prostate stimulated, you can look into prostate massagers. They tend to be smaller and angled to specifically hit your P-spot. Butt plugs are an option, as are dildos and vibrators. You may find it easier to work with an array, getting used to a smaller size and then working your way up. You may find that you don’t need much to get you going—for as many dicks as I’ve taken, fingers still do the trick for me.
I have no idea whether you’ll have multiple orgasms or not from anal. Again: trial and error. Do not stress yourself out if you don’t climax from anal stimulation alone. The combination of anal and penile stimulation is amazing as it is. A nation of bear bottoms will tell you that a hairy ass is not an issue, but you can look into hole hair removal if you’re so inclined. If it doesn’t bother you, it’s not a problem. But your partner may have other ideas, in which case you can make it your problem or not, at your discretion.
If you plan on going beyond toys and having sex with an actual penis, you should also look into getting screened by a doctor who specializes in colon and rectal care. HPV is everywhere and it can cause cancer, so an annual pap smear (as well as an internal examination for warts and other irregular cell activity) is a good idea.
It took me more than 10 years or so to reliably enjoy bottoming. It can be a slow process, so have patience with yourself. I’m extremely glad I didn’t give up. Believe in your hole.
Dear How to Do It,
I am a cis woman (40), married for 12 years. I grew up in a tumultuous and unhappy home, and therefore my happy, stable marriage to a man who I love and am attracted to is of enormous importance in my life. We are very open with each other and have shared with each other when we’ve had small crushes outside the marriage. Three years ago, a discussion of a crush led to me giving him permission to explore further, which he did, but I will be honest, I had a response that was big and hurt. There was a lot about my childhood that was triggered, and it came as a big surprise to me. We worked with a therapist together, and it was rough for a little while, but we got through it, and unfortunately, in the process, the exploration of that crush didn’t go any further.
Now, we have a new friend in our lives and I am the one with a crush, and my husband is offering permission to explore this. And I have two questions: 1) What are the steps we can take to try to crisis-proof this process and make sure we don’t hit the same kind of potholes we hit last time, now on the other side? Exploring this crush is nowhere near as important to me as keeping my relationship with my husband strong and healthy. 2) I haven’t been single in nearly two decades! And even when I was in my 20s, I was terrible at flirting. How do I do this? My impression is that there is flirtation and interest on both sides, but again, I was really bad at this back when I was actually in practice. I feel like any communication of our openness to ethical non-monogamy is in the end a form of an invitation, and I don’t want to make someone uncomfortable by broadcasting interest that might not be mutual. Can I have a script?
—How Do I Do This Again?
Dear Do This Again,
You have firsthand evidence of why it is impossible to make this situation crisis-proof: You don’t know how it will feel until you’re in the thick of it. What can mitigate the overwhelming feelings that come with ethical nonmonogamy, though, is a sense of connectedness with your partner through frequent and open communication. In my experience, the most useful rule is: All rules are subject to change. Guidelines that make sense in theory, may cease doing so in practice. If your partner doesn’t end up liking what he sees, you should be willing to hear him out (and likely, modify or at least compromise) for the continued well-being of your relationship. If you don’t bend, your bond can break. Sometimes it’s worth throwing it all away for the new bond you forge, but you explicitly state that’s not something you want.
The second part of your question is in some ways more difficult to solve than the first. I guess what you should primarily accept is that you might make someone uncomfortable by broadcasting interest that might not be mutual. This is the risk you take when expressing your interest. But it’s a worthy risk given the alternative, which is nothing happening because you didn’t act on your curiosity. Luckily, for most reasonable people, the minor discomfort that comes from being on the receiving end of an unrequited crush isn’t a big deal. They acknowledge it and move on, perhaps even deriving an ego boost from it. Simple. (Keep in mind, though that repeated broadcasting of explicit interest with no reciprocation constitutes badgering, or worse: attempted coercion. If you make things clear once, maybe twice, and don’t get any bites, consider yourself rejected and move on.)
Rather than a script, which I think would be too precise to cover all the potential ways this could go, I’ll offer a suggestion, which is to naturally work into conversation 1) sex, 2) your open-ish relationship with your husband, and 3) your interest in women. Set the scene by talking about what’s going on with you, and see if you can sow some interest. Compliments on your friend’s physical appearance—both in the innate and adornment realms—will also telegraph where your head is at. You can build from there if you find her reciprocating within your conversations, or if you sense any intrigue coming from your friend. The idea is to basically show her what’s possible and see if she’s interested in exploring those possibilities. Personally, I have found that nothing beats the direct approach—“You’re so hot, I would love to play with you”—but your situation, as well as you, are probably a little too sensitive for that at this point.
—Rich
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