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’m a 45-year-old straight male in a 10-plus year (gently) open relationship with a 35-year-old straight female. When I was a teen, anal play (object insertion) was an occasional part of my masturbation repertoire. As an adult with a “good, game, and giving” primary partner (and occasional others), there has been much less time and need for self-gratification. Butt play went by the wayside long ago. At the beginning of COVID, I was at home alone for several weeks. One horny night, old habits kicked in, I went shopping through our toy box, and I lubed up and put in a pink pop plug. I got hard faster than I have in years (things rise a little slower now that I’m in my 40s). Anyway, I liked it. And our toys have now taken a staring roll in my infrequent self-pleasuring sessions.
But now I’m fantasizing about involving a partner. Here is the problem. I’m definitely straight. And my BDSM play has always skewed toward domming. My primary partner definitely leans submissive. Maybe seven or eight years ago she made a casual comment about not being interested in pegging men. This is in line with her sexual preferences, which tend to be simply being fucked. I worry that outside of gay bottoms and submissive straight men, receiving anal pleasure and toys is extremely uncommon, and seen as unmanly. I, of course, don’t know what my few casual play partners will think if I were to ask, but worry that not only will I get a “no way,” but it would damage any of those relationships, as they would no longer see me as the masculine, straight, dom-like partner that they are happy with. How common is this interest for straight men? How common is it for women to enjoy pegging? Do I keep this sexual activity to myself? Or find a new partner into this before I risk my old relationships? Or is this not a real risk, and all in my head?
—Afraid to Try
Dear Afraid to Try,
Archetypes are great until they become sort of “boundaries of persona in a box.” Identifying as a “masculine, straight, dom-like partner” seems to come with some ideas about what is masculine, straight, and dom-like, which might not serve you. Think about where the limit is of what might undermine your Top-Manness. Where does that limit come from? What you’re assuming others might perceive of you? Some internalized concepts? How accurate do you think those assumptions and concepts are? Would you apply them to other men?
Your primary partner, whose preference is to simply be fucked, probably isn’t going to jump at the chance to peg you. Pegging is a very active activity, even when done from a submissive position. Even if all you’re doing is being a base for the strap, there’s still more energy and exertion involved, and often a certain amount of unfamiliarity to overcome with having that sort of appendage. A finger in the ass during a blowjob might be a different story, though. And you inserting a plug for the passive stimulation might not be something she feels requires any engagement from her at all.
Beyond this, you also never know what activity, with which person, in a specific context might turn out to be incredibly hot. Sometimes we surprise ourselves; our lovers surprise us; and in an effort to be, as you borrowed from Dan Savage, “good, giving, and game,” sometimes our lovers surprise themselves. With search rates for pegging videos on the rise—and the way that content producers often tailor their production and advertising to current trends—you might find that one or more of your lovers is already curious. I say go for it, with the understanding that there is a small but real risk of receiving an “Ew, gross.”
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Dear How to Do It,
I’m a 40-something woman in a long-term marriage that has had its ups and downs, but we are committed to one another. Despite occasional troubles, my husband and I have strong libidos and even after 20 years together, we still have sex nearly every day because it is when we seem to be most compatible.
About two years ago I met someone online through a friend group. We had a lot in common and he started sending me dozens of DMs. They were flirtatious and witty, occasionally suggestive. He would say things in the group that suggested he was creeping on me online. I’ll admit I liked the attention—I work hard to stay in shape and be attractive, and I became very attracted to him. We interacted on group FaceTime chats but on every occasion when I was 1:1 with him, he was cold and indifferent or turned off his camera. So I took the hint that he was not really interested in me, and I did not pursue it. However, I still developed an insane crush on him. I couldn’t stop thinking about him. So, six months ago, I muted him and stopped interacting with him entirely. He reached out once, and I told him why I pulled away. He said he understood.
The problem? it’s been six months, and I’m still thinking about him all the time, particularly when I’m having sex with my husband. I’ve tried all the tricks—imagining gross things about him, distracting myself with other activities writing an affirmation why I should stop thinking about him for many good reasons—but I can’t get him off my mind. Do you have any more tips on how to get over a relationship that never actually happened?
—Can’t Quit Him
Dear Can’t Quit Him,
You don’t mention any specific relationship boundaries in your marriage, so I’m assuming that you’re monogamous. I think considering the reasons your attention strayed from your husband is the way forward. (Rich and I offered some more thoughts on a similar subject in a column a few months back that can be a starting point.) You say you liked the attention you received from this person you met online. How much attention are you getting from your husband outside of sex? What’s up with you having sex nearly every day “because” that’s when you “seem [..] most compatible”? If you sort that out, you’ll probably find yourself more attracted to your husband, and you’ll likely have an easier time focusing on him over this crush.
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Dear How to Do It,
I am 60, am told I look younger, active and social, and enjoy my life. My husband died two years ago. It was my first marriage and we were married for 11-plus years. Our sex life had declined over the years because of his illness, and in the last couple of years before he died it was down to once or twice a year and it was pretty vanilla. It has been five years since I’ve had sex.
Over the past several months, I connected with a man about my age who was interested in working with me on a project. He lives in another city and over the course of our phone calls, we began flirting, which led to phone sex and exploring fantasies. It’s been extremely exciting because I thought that part of me and that part of my life was over. I’ll be traveling to his city next month for a completely separate work project and we have talked about hooking up. He now wants to have a threesome. But I am panicking about my body. Over the course of the last 25 years or so, I’ve lost about 100 pounds. That weight loss, along with being 60, has left my body loose and flabby. (I’m scheduled for a tummy tuck and breast lift next month, completely separate from this situation.) Through therapy and a 12-step program for eating disorders, I have become much more comfortable in my skin. UNTIL I think about being naked again with someone, especially this guy who is intensely sexual and very buff.
Intellectually, I can tell myself all sorts of people have all sorts of sex, but I start to panic when I think of myself getting to do this. I’ve told the guy about my weight loss and my shyness about my body, and described myself as Rubenesque. He’s been unfazed and emphasized that we’re just going to have fun, that a lot of men like a woman with meat on her bones, etc. I know from social media he’s really buff but I start getting all up in my head about I’m supposed to be smaller than him. The more I think about it, the more lumpen and gelatinous I start feeling, and all the fat shaming and Catholic upbringing about sex in the first place comes full bore. How do I change my thinking that only beautiful people with nice bodies get to have sex? How do I own this opportunity? How do I get out of my own way? How do I leap and know the net will appear?
—How Do I Get Out of My Own Way?
Dear Get Out of My Own Way,
We don’t know if the net will appear! Every time I disclose something about myself to a new partner, or allow them to see some physical aspect that is less than idealized, I’m taking a risk. Sometimes people reject me, and sometimes they’re kind of cruel about it. The more experience you gain being rejected, the easier it tends to get. That said, most people do their best to follow their understanding of kindness.
What you can do is build your own net. Make sure that you’ve got a friend lined up in case the guy is mean, who can be on standby to listen to you vent on the phone, or take you for a drink, a walk, or a sundae. Know how, if you do need to bail, you’ll extricate yourself from the situation. This means planning details like having your own transportation or a rideshare app on your phone and knowing where your purse and important clothes are. I’m a fan of keeping panties in the purse, or pants pocket, as applicable.
If the idea of leaping into a self-built net, while knowing that the risks are real, is too much, you might reach out to a counselor (How was your relationship with the one you’ve already worked with?) to get some expert support as you work through how you feel about your body now and your anxieties.
Dear How to Do It,
I’m a cis woman in my 30s, so this might seem like a naive question, but is it possible to come without, like, feeling it? For the past few months, my usual method of masturbation has gotten me to the precipice without fail, but as I’m reaching what feels like the point of no return…nothing. The pressure just goes away with no sense of release, much less pleasure. I try to keep going (I’m capable of multiple orgasms, with some effort), but the same problem continues, and finally, I give up when I get too tired and in my head about it. Masturbation is my only sexual outlet right now, which isn’t a problem, except I used to be pretty good at it and now I’m not. I miss my old orgasms!
—Frustrated
Dear Frustrated,
To directly answer your question: maybe. I mean, the definition of orgasm usually involves some combination of muscle tension, contractions, and release. But you’re describing an absence of sensations—of release and pleasure. If you’ve gone on antidepressants or other medication known to have sexual side effects, these recent occurrences are worth talking to your doctor about. Otherwise, I’d give it another couple of months and then consider trying to find some answers with either your primary care physician, a gynecologist, or a psychologist—depending on how your healthcare coverage is set up and which of these kinds of professionals you already have a good relationship with. I would want someone I trust to get all the details and give an opinion on whether it’s worth running any tests if this issue approached a year.
In the meantime, take the pressure off of orgasming and either try to enjoy the journey or engage in other activities. When you do feel strongly aroused, try methods of masturbation that are different from any tried-and-true techniques you might be using. You might start with Epiphora’s sex toy blog, or Barbara Carrellas’ Urban Tantra. Sometimes our bodies, and sexual responses, suddenly change and we have to do some experimentation to catch up.
—Stoya
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I have a situation I’m very confused about. My husband and I were married for 31 years. We didn’t have sex for the last 15 years. I shopped and overate to compensate. He was sick for the past five years and very, very sick in the last year. He recently passed away. I started having sexual feelings some time last year. In the past year, we had four caregivers for my husband.
