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 50s man who has repressed most aspects of his sexuality for most of his life. I enjoy women, but I am very bi-curious. I have a lot of unexplored kinks. I never revealed any of this when I was dating in my 20s, and while I did reveal some interests to my wife, she was very vanilla and had no interest in exploring these with me, or in allowing me to explore on my own. We divorced four years ago (for many reasons having nothing to do with our sexual incompatibility, though that didn’t help!), and I quickly met another woman who is a good and kind partner, and much more enthusiastic about sex and more open-minded than my ex. However, I find I am still afraid to share all aspects of my desires with her, for fear of being rejected. She knows nothing about my desire to explore sex with men, and I have shared only a little of some of my other desires. Some things she has said make me feel pretty certain she would not be open to some of the things I want to try.
So, I have two questions for you: First, how does one share non-typical sexual desires with a partner? How do you get up the nerve to reveal deeply personal information that may result in rejection, or worse, being viewed as a creepy person? And second, where can I go to meet people with similar interests? For instance, one of my kinks is CFNM (clothed female, naked male), but I have no idea where to meet women who I could enjoy this with.
—Kinky and Confused
Before I get into your actual questions, are you sure you want to be with another woman who you’re sexually incompatible with? You say you met her quickly, and while I’m sure she’s as great and open-minded as you say, your sexuality is important to you—and you also say you’re pretty sure she won’t be into what you are. I think it’s good—certainly more efficient—to get the big potential mismatches out of the way early. For me, that’s “Sometimes I touch people’s genitals on video.” For you, that’s “I’m very curious about bisexuality and want to explore it in practice.”
“Typical” and “sexuality” get interesting when you put them together. Unlike a blood test, quantifying our inner worlds is self-reported. We must know ourselves well to disclose accurate information. Widespread access to free pornography online has given us an interesting picture of what people seek out and watch for pleasure, and the words they use to search for it. I don’t produce many custom videos, but I’ve heard some wild stories and received requests for some interesting and detailed fantasies. Mostly what I’ve learned is that human sexuality is even more complex, specific, and varied than we’d thought. Clothed female, nude male may be a manifestation of a more umbrella kink like exhibitionism or humiliation, a division of a big category into an increasingly narrow and precise one.
Speaking of CFNM, and not wanting to be viewed as a creep, let’s work on your wording. Can you describe what gets you off about it? Would clothed male, nude male work just as well as long as you’re the naked one? Is it about power? You can start the conversation with something like “I’m curious to learn more about what you’re into sexually, and I would like to share some of my own interests. Will you let me know if you want to have that talk at some point?” Expressing interest and leaving an invitation is a tip I picked up from sex educator Vonka Romanov. Or you can wait for an opportunity for it to come up naturally and gently move the conversation further in that direction. Be prepared to share the psychology of it. Be prepared for questions you might not have the answers to at this time. Do your best to let your partner in on the specifics of what you like and what about it you like.
You may get rejected. This rejection may be gentle or harsh. If that happens, to meet people who may share your interests, you can try the forums of various websites, dating apps like Feeld and OKCupid that tend to attract more kinky people, and—when it’s safe to do so—you can go to munches or sex and fetish parties. Your people are out there, whether or not it’s this good and kind new partner.
Dear How to Do It,
My girlfriend and I (both women in our early 20s) have been together for a few years now. We’ve talked about exploring non-monogamy in the past, but it’s never actually come to much before now. My girlfriend and I are both working for the same company this summer, and we’ve both developed a crush on our coworker, Peter. This was a surprise to me especially—I haven’t had feelings for a man in years. All three of us are good friends at work, we’ve both been flirting with him (my girlfriend more directly than me), and I think he’s flirting back a bit, but it hasn’t developed beyond that yet.
I had kind of expected that, when my girlfriend wanted to actually act on her feelings for someone else, I would feel jealous of the other person and insecure about our relationship. Instead, this has so far been GREAT for our relationship—our sex life has improved in both quality and quantity as we’re both buzzing with the thrill of a new crush. But I’m surprised by how jealous and insecure I feel that Peter might have feelings for my girlfriend and not for me.
I’ve never really thought much about having a threesome or what it would be like to have a third person in our relationship before now. But to me that’s what makes the most sense with our current dynamic with our coworker. I would be hurt if my girlfriend and my crush had a hot summer fling without me. My girlfriend, on the other hand, had mostly been fantasizing about hooking up with Peter on her own, and says the idea of a threesome is more intimidating than exciting to her.
Since we’re new to non-monogamy and this isn’t a scenario we could have anticipated, I guess I’m wondering: What are our options? Do my girlfriend and I have incompatible dreams here? How do we get on the same page? And then, how do we (or just my girlfriend?) bring this up with Peter to see if he’s even interested?
So you and your girlfriend would be opening up your relationship after a few years of monogamy, for the first time, with a co-worker.
Please don’t do this.
It’s too many variables with a high combustion risk all layered on top of each other. It’s an explosive lasagna. Sure, it might be delicious, but it’s dangerous.
You and your girlfriend would be well served by a serious conversation about what feels like it might be OK and what feels like it might not before the two of you, or one of you on their own, find another interesting potential partner. But please not this guy. My concern is that if it blows up, and you put this company down on your resume or LinkedIn, the reference after a dramatic workplace threesome could be damaging to your career.
When we answered this question on the Slate Live chat, Rich mentioned that he prefers to defer to the more conservative partner in open arrangements—the person with qualms—and I think that’s wonderful advice.
Dear How to Do It,
I’m a middle-aged man married for 10 years to a woman the same age. We’re financially stable, and we don’t have kids. Our marriage is great, and we rarely argue. We don’t have health issues or stressful jobs. We have great conversation, and she’s my best friend. However, there’s one problem: we never have sex. Like most couples, we started with higher frequency, but over the last few years, it has become almost nonexistent. We’ve gone as long as eight months without. I gently bring up the issue every few months, and she always agrees that we can do better. We usually have sex once or twice after these conversations, then it’s back to nothing.
I’ve suggested things we could do to keep each other excited, but she doesn’t seem interested. When we do have sex, we always follow the same routine. We make out for a while, I get her off with my fingers, then missionary PIV until I finish. That’s it. I surprised her last year with a basic vibrator in hopes of sparking something. We tried it once, and despite enjoying it, she never mentioned it again. She has also told me in the past that she doesn’t masturbate. I’m not sure she ever has.
I’m not sure what to do here. She says she loves me and is still attracted to me, so I don’t understand what’s going on. She’s not a prude, and is very progressive in all other areas. Is there hope of fixing us, or am I doomed to a life of masturbating when she’s not home for the rest of our days?
—No Kids, No Stress, No Sex
Your wife may not be very sexual. She might be shy about sexuality for any number of reasons. She might have the kind of sexual response that needs a particular kind of foreplay. (For more on that, see Emily Nagoski’s Come As You Are.) Neither of us can figure that out without some further information from her, so you’ll have to bring it up. And you’ll need to try something different, because the way these conversations have been happening isn’t solving anything long-term.
Draw on the skills that help you maintain a great marriage. Pick a discussion time where everyone is sober, adequately fed, alert, and comfortable. Think about what you’ll say beforehand, with care taken to phrase things in ways she’ll be able to easily hear, and that express your position fully. Something like “I think we might have different libido levels, and I’d like to talk about it with you.” If she agrees, you might pull out some knowledge from the Nagoski book and ask her if she’d be interested in trying some of her tips. If she disagrees, you’ll want to ask whether she feels comfortable expressing her sexuality to you. If she doesn’t, maybe therapy is worth a try. If she does, it is completely reasonable to ask her to help you figure out where the miscommunication is happening, because there’s a big one.
If your wife isn’t as into sex as you are, her progressiveness may extend to opening up the marriage. So that’s worth bringing up, too, if it gets there. Good luck.
Dear How to Do It,
My partner and I are both trans and (to give a little context in the form of imperfect and ephemeral labels), they’re a former stone butch who now identifies more as a switch in the bedroom, and I’m a past pillow princess who’s also essentially a switch nowadays. It feels like we’re very good about being on the same page in terms of preferences for the most part, and are great at communication before, during, and after. We’re both former sex educators and HIV counselors, so feelings, sex, logistics, annual check-ups—we’ve got that part down.
They like to use a strap-on now and then, and I have minimal experience with it personally. They’re the first person I’ve used one with, which came after many long conversations, and they did find a set of equipment I generally like and seems well-suited to what we’re both looking for. The issue is in practice: I tense up with them when it comes to penetration, and it’s hard to make it comfortable. We’ve tried a lot of positions, making sure lubrication is not the issue, lots and lots of foreplay, the usual troubleshooting. I masturbate easily with dildos of this size on my own time and with my partner. This is part of a pattern on my end—I’m a trauma survivor, my vulnerability with partners doesn’t come easily in general, and honestly, sometimes I worry I’ll get dysphoric about being penetrated this way (kind of like getting anxious about getting anxious, if you know that feeling), which makes me more in my head. That dysphoria has happened a couple times when we’ve had sex, mostly at the beginning of our relationship, but my partner is extremely affirming of my gender and is great at reading signals and backing off immediately if it seems like it’s happening. I know getting frustrated over this will just make it worse, but I do think we’re set up for success and yet, it’s still a struggle and has been for almost a year now.
I just put in an order for a slightly smaller dildo (a half inch smaller in diameter than the other one) to try and work our way up, but do you have any other particular suggestions? I do fantasize about riding it with abandon, and I know my partner would like it more in the rotation. With the COVID-19 keeping us in the house, now we try about two or three times a month, and we can find a position that isn’t actively painful for me maybe half of those times (this is a major improvement compared to a few months ago). A magic hack would be beautiful, but just an outside opinion is very welcome at this point.
—Would-Be Power Bottom
Dear Would-Be Power Bottom,
I am fresh out of magic hacks.
Strap-ons, external genitalia, and dildos all look like an obelisk, but they can be very different experiences. So I don’t think it’s strange that you have to find your angles all over again with your partner’s protrusion.
But your dysphoria worry seems key here. Ask yourself: What’s the worst thing that can happen? Seriously—I want a list of 25 things that could spiral out of control, and then I want a plan for each of them. These plans should be multi-part, because not only are you thinking about what you want done in the worst-case scenario, you should be thinking about various points along the way where you could head disaster off at the pass. Maybe that’s acknowledging that you probably will experience dysphoria again and deciding that you’ll signal for a stop at the first hint. You can learn cognitive behavioral therapy techniques to help you reduce anxiety and return yourself to the present moment. Sharp sensations like biting a lemon or holding ice can be useful, as can distractions that make your brain work. You’re best off in the hands of a qualified therapist for this part. You also might consider reading Staci Haines’s Healing Sex.
Once you’re able to manage those fears, I hope you’ll be riding with abandon—but give yourself time and be gentle.
More How to Do It
My friends and I are close and very candid about our sexual experiences. I generally don’t have sex with my friends, but they don’t believe in those restrictions. We were talking recently about planning a weekend where a group of us would go away and possibly have an orgy. I’m really excited about the idea—except for one qualm.
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