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 32-year-old woman who grew up in a very conservative, non-sex-positive environment. I’m also not conventionally attractive and have never received much interest from men. At 27, I was still a virgin and was convinced romance would never happen for me. I just accepted it and focused on enjoying masturbation. I went on that way until a friend I’ve always had a crush on asked me out. When we first started dating, he was incredible about working with me through my inexperience and insecurities when it came to sex. Fast forward five years and we are married and share an adventurous and fulfilling sex life. I have no doubts that he loves me.
What is the problem then? My husband is very hot. When we meet anyone new, they always do a double-take that screams “Wait, you’re married to her?” He’s also had far more sexual experiences than me. He tells me, repeatedly, that sex with me is the most satisfying sexual experience he’s had. I believe him because my husband isn’t given to lying or false flattery. But there is this constant voice in my head that keeps saying this can’t possibly be true. I can’t seem to get over my old insecurities or resentment at myself for not being more experienced. I feel like we’ll never be on an equal standing, even though, logically, I know this isn’t a competition, and I have no desire to sleep with anyone else. I also cannot change the past nor would I really want to because it led to where we are now. So, how do I get that little voice in my head to shut up?
Dear Plain Jane,
Given the abundance of evidence contrary to that self-sabotaging little voice, it’s reasonable to label your negative thinking as a cognitive distortion, which can be a sign of depression. I suspect that these specific feelings of unworthiness are part of your self-esteem’s bigger picture, and I would wager a guess that said picture is somewhat out of focus. If you haven’t spoken with a therapist about this issue and/or other feelings potentially related to depression, I encourage you to do so. This seems like a situation where cognitive behavioral therapy could be useful, so consider pursuing that avenue.
I don’t feel like I can tell you anything you don’t already know—the key here is to resolve this intellectual/emotional disconnect, as you are well aware. I think this process will involve a journey to self-acceptance. Perhaps you can also come to see things not in terms of how they should or should not be, but what they are. I have no doubt that your husband’s compassionate, attentive love is a direct result of your good character; he loves you because you are lovable. At the same time, you cannot overlook the role of luck in good fortune—right place, right time, right words exchanged, etc. You are worthy of your relationship, and at the same time, forces having nothing to do with fairness or righteousness have helped facilitate it. Think of it as a condition—luck smiled on you for whatever reason, and the best way that you can honor it is to be mindful and not take it for granted. Accept this wonderful partner, who is gracing you irrespective of your past, your self-perception, or the way you thought things were going. No matter how you got here, here you are.
Dear How to Do It,
I’m a 40-ish married guy with a few kids, house in the burbs, etc. I grew up in a sexually repressed evangelical environment, had no penetrative sex until I was a junior in college, and have very limited sexual experience in general. (Outside of what I relate above, I’ve only had sex with four women, all of them in fairly long-term relationships.) I grew up scared of sex, scared of girls, and generally never experimented … until about 10 years ago. On a work trip with colleagues, we went to a strip club, and my experience was mind-blowing. I’d been to clubs before in my 20s, but I was shy and poor and didn’t get much out of it. Now I was a sexually frustrated married guy with money, and the dancers loved me. I understand that they loved my money, but that’s OK by me. In addition to lap dances (simulated sex), I’ve had blow jobs, penetrative sex, and I’ve discovered that I enjoy being pinched, slapped, and generally dominated. I’ve gone to enough clubs at this point that I can often identify the women most likely to be dominating and those are the ones I choose—that is more my drive to go than anything else, even in clubs where “extras” are readily offered.
Until COVID, this was an OK solution for me. I would occasionally (four to six times per year) go to a club while on travel, have an experience (sometimes fantastic, oftentimes just fine, occasionally bad). My sex life at home is not going to change (we have very vanilla sex a few times per year, and my partner has a similar background to me and is not interested in anything other than missionary—she will not even let me go down on her).
My question, really, is how can I explore this new sexual liberation and desire to experiment in a safer and more reliable environment than a strip club? I feel like I’m too old to keep going to clubs, and it’s low odds that I find someone who syncs with what I want to do. Dancers often give me their numbers for OTC (outside the club) get-togethers, but I’ve not done that. I know about mistresses and dungeons somewhat, but I don’t know if that’s what I want as so far what I’ve done seems very basic (slapping, pinching, light biting during lap dances). I don’t want to separate from my wife—other than sex, our relationship works OK and I want stability for my kids—but I do feel like I figured out in my late 30s what great, hot sex really was for me, and I don’t quite know how to get that given this.
Dear Late Bloomer,
Your letter is lacking background that would allow me to do my job in good conscience: What does your wife think of your extracurricular fun? Because closed, monogamous relationships are the norm in Western culture, I have to assume that if you were in an open relationship, you would have stated it. Thus, I have a hunch that what you’re asking me to do is help you cheat better. I will not do that for obvious reasons (cheating sucks) and also because I believe that such a large-scale moral transgression can only be accomplished with a high level of cunning. Like any skill, deception is something you must practice. Use it or lose it. To help you here might also facilitate atrophy, and so I would be doing your admittedly craven endeavor a disservice.
This is a highfalutin way of me advising you not to cheat on your wife.
My Boyfriend’s Shocking Past With His Mom Is Ruining Our Sex Life
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Dear How to Do It,
I come from a very large, very close family. I have lots of cousins that I grew up with over the years and still spend time with at frequent family get-togethers. My problem is this: I have one cousin a few years older that I have had steamy dreams about on a pretty regular basis over the last few years (stepcousin actually, the lack of a blood relation makes me feel slightly less icked-out, I guess, despite being raised together since elementary school). I can’t understand why: I find nothing about them attractive, they’re really the opposite of my usual type. How can I make this stop? Why can’t my brain give me some dreams about Chris Hemsworth or something? Help!
Dear Sweet Dreams,
It’s important to keep in mind that your recurring incest-adjacent dream may mean absolutely nothing. I suspect that if indeed you have no attraction to this cousin, even on an unconscious level, that you are in fact stuck in the kind of thought loop a person can find themselves in when they try not to think about something and end up thinking about it more. Guy Leschziner gives a rather evenhanded assessment of the significance of dreams (and lack thereof) in his 2019 book The Nocturnal Brain: Nightmares, Neuroscience, and the Secret World of Sleep:
Some of our dreams may reflect the experiences of the day before, while others may bear no such meaningful relationship. They are the summation of our life to date. It is also unsurprising, therefore, that some dreams or nightmares may recur, in an effort to understand the meaning of our daytime experiences. But these dreams are a function of the brain. “The brain creates the mind and the mind creates the brain,” Hobson says. The brain and the mind are one and the same.
This may be something that passes, but in the meantime, you can get proactive if you’re so inclined. In this Lifehacker piece, professor/sleep researcher Antonio Zadra recommends something called image rehearsal therapy, which involves taking mental (or written) note after waking up from a disturbing dream (and I think it’s fair to classify these stepcousin dreams as nightmares given how unwanted they are) and thinking of an element you’d like to change. Reimagine the sex dream you just had with Hemsworth in your cousin’s stead. This, I imagine, will require some practice, but it seems worth a shot. You may also want to look into lucid dreaming, in which you consciously control your dreams. It’s another long process that often requires note-taking, keeping a dream journal, and practice, practice, practice. It’s a lot of work and the results aren’t guaranteed, but at least you’ll feel like you’re doing something as opposed to sitting back and letting your mind defile you with images of cousin sex.
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Dear How to Do It,
My partner (36F) and myself (36M) have been in a committed relationship for eight years. We’ve known each other twice that and were best friends when we had different partners in the past. Recently, we’ve really opened up about exploring sexuality and kinks, and so far it’s been great. She has the desire to perform penetrative sex on me, and I’m fully on board. On our most recent anniversary, we picked up some new toys to help ease into the things we’d like to explore. One gift to me was a prostate massager, so I can experience greater sensations of pleasure and she can dip a toe into penetrating me with it. We’ve had some intimate sessions playing with this toy to great effect, and I’ve also enjoyed using it solo when penetrative sex is off the table (either due to menstruating or when not feeling up to it). We’ve probably used it four times to date, two as a couple and the rest as solo performances.
I also currently have my MIL staying with us, so sex time has been limited in our small home (especially the kind we usually have … if her mother heard it, I think it would break her very evangelical mind to pieces). We’ve both been horny and grabbing at each other for days, waiting anxiously for MIL to stay with her sister for a while, so we could have some alone time. The time finally came, and I was ready all day. She slipped in the massager, and we started performing oral sex. That part went great, until it was my turn. I just couldn’t maintain an erection. I’d get hard and then go soft during the act. Over and over. We took the prostate massager out, had some water, cuddled, and tried again. Still no luck. I’ve never really had a problem in this department before, and as far as our relationship goes, it’s been pretty good, but the sex has always been “KING OF NEW YORK! A #1” (read: amazing).
This is only our third bout together using this toy. I’m wondering if there’s such a thing as overstimulation of the prostate, or if something else is going on physically or mentally. Physically, I feel no pain. Mentally, I want to have sex and have it with her. I just couldn’t do it. I’m processing a lot as this inability to perform (outside of sickness, migraines, or surgery, etc.) has never occurred before. I feel like I’m a bit young for ED given my age and aggressive libido. I have been suffering from long-term COVID symptoms for the past year (especially inflammation and headaches), but being unable to get hard has never been a symptom thus far. Am I just overloading my body with Assgasms? Or is something else possibly going on? Is this something I should take to my general physician or a sex therapist? Or is it just a normal thing that sometimes just happens?
—Limp and Lost
Dear Limp and Lost,
Please try to relax. I feel like you’re this close to spiraling off the page. Try some deep breathing—like the kind you might do when being penetrated from behind. (I trust you know what I mean.) You are likely fine, and anxiety being the boner-killer that it is, continued worrying may interfere with future performance. And then you really will be spiraling into the most vicious of circles.
I think it helps to acknowledge the context of your deflated encounter. All of that buildup could have given you a feeling of pressure to perform—“It’s now or never” thinking can be just as galvanizing as inhibiting. It can be intimidating. Such intense lead-up to sex sets people up for disappointment.
The reason I’m not willing to accept your hypothesis about anal stimulation resulting in ED is 1) I’ve seen a lot of buttholes virtually destroyed with little effect on the dick around the corner, and 2) prostate massage has long been used as a method for treating ED. That doesn’t mean it always works, or that it would have that effect on you, but it just seems unlikely that stimulating your prostate five times would leave your dick out of commission.
I ran your letter by my go-to urology source, Charles Welliver, director of men’s health at Albany Medical College, and he wasn’t concerned about your one-time performance being indicative of a larger issue. “Seems like this is a one-off misfire for him,” he wrote in an email. “He just had a bad day. It happens. I wouldn’t read too much into the massager-ED thing.” He suggested seeing a doctor if this persists, but predicted that by the time this column is published, you’d be functioning as you were before.
More How to Do It
I might be the first woman in recorded history to say this, but I hate being called ‘“sexy.” It’s about 10 percent because it’s not a word I’d ever think of using to describe myself, thanks to some old, now mostly well-controlled body image issues, but 90 percent because I just have a squick about that word! I don’t like the way it sounds or even the way it looks written on the page. My (wonderful) boyfriend of four years will occasionally use it during sex, and it totally throws me off every time. I don’t know how to respond and usually just ignore it or mumble “thanks” and try to get back into the mood. On the flip side, apart from this he doesn’t often compliment my appearance—I could probably count the number of times he’s called me “cute,” “pretty,” or “beautiful” on one hand. I know it’s shallow, but it would mean a lot to me to hear that from him more often, although getting rid of “sexy” is probably more of a priority. Do I just learn to live with it? Say something? What would I say?