How to Do It

My Boyfriend’s Job Makes It Impossible for Him to Do My Favorite Sex Act

I really miss it.

Woman looking at a neon hand.
Photo illustration by Slate. Photo by Darius Bashar on Unsplash.

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 woman in my early 30s, and I’ve been dating my early 30s boyfriend for about a year. Our sex life is generally great, except for one thing: fingering. Getting fingered is hands down (no pun intended) my favorite sex act, but my boyfriend is a carpenter with big hands who also bites his nails, resulting in super calloused and jacked-up hands and ragged nails. He generously gives lots of oral and other forms of foreplay, but his fingers are painful, so we don’t do it. He’s working on the nail-biting, but his career isn’t going to change, so he’ll always have calloused hands. Is there anything we can do to make fingering possible? He’s embarrassed about his hands, so I’m not sure how to broach this subject, but I really miss this!

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—Unhanded in Utah

Dear Unhanded,

This is where finger condoms may actually come in—are you ready for it?—handy. Non-latex gloves are also an option. Whichever barrier you end up going with, you’ll probably want to use lubrication to prevent chafing. Err on the side of too much to start with. And although it won’t help with nails, some creams for working hands, like this one, could provide a bit of relief too.

As for broaching the subject, I’d recommend bringing it up directly yet gently. You might start with some positive reinforcement on his oral skills—maybe he’s great at teasing, or maybe he knows exactly what spot to zero in on. Then acknowledge his effort: “I see you working to decrease your nail-biting.” Next, put forward your solution, something like “I think it might be worth trying barriers, like gloves, for fingering.” He might be a little embarrassed. That’s OK! It happens sometimes. In this case, I think you’ll both feel it’s worth a moment of discomfort for even a single session of pleasure.

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Dear How to Do It,

I am a 35-year-old woman who considers herself a very sexual person. I have always enjoyed sex and masturbation, and I don’t have shame around my sexuality or the pursuit of it. The problem is that I have not had an orgasm from a partner in more than 10 years. I have no issues when I am masturbating, and therein might lie the problem. I always watch porn when I masturbate, and I think maybe I’ve programmed my mind to need it? In my research I have found many “anti-fap” websites and things focused on men and how porn is desensitizing them, but I have found zero information about women having this issue (although I’m sure the same rules apply to us).

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I’m not entirely convinced that quitting masturbating is answer to my problems. Not to mention the thought of leaving my orgasms completely up to my regular partners puts more pressure on an already high-pressure situation. And it’s not that I am uncomfortable with the people whom I regularly sleep with. Nor is it that they are unwilling to put in the work or are unaware I have this problem (I stopped faking years ago). I have been having increasingly good and experimental sex as I’ve gotten older, but the orgasms still don’t come. I’ve always derived pleasure out of giving others pleasure, so when the pleasure is focused on me, I get inside my head. I start to become too aware of how long it’s taking for me to cum. I’ve never in my life had a orgasm from penetrative sex—only clitoral stimulation—and I don’t think I’m alone in that. I know bringing toys to into the situation could be a big help, but I’m afraid I’m going to further desensitize myself. And the worst part is I have never met or found another woman who has this problem. I feel alone and like there is something very wrong with me. What do you think I should do? Quit porn cold turkey? Set a timer during oral so I’m not paranoid that it’s been 45 minutes? See a therapist?

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—FOMOOO (Fear of Missing Out on Orgasms)

Dear FOMOOO,

First of all, I can assure you that you’re not alone. Many women—consistently, across various studies—report inability to orgasm reliably, or at all, without clitoral stimulation. Many women don’t orgasm at all regardless of stimulation, and some can orgasm when they’re solo but not with partners. I imagine the lack of women to commiserate with has an othering quality to it that I suspect is uncomfortable. This is one area where the gender binary causes trouble—your similarities with the “no fap” crowd are overpowered by the very real difference in the ways your genders are socialized. Seeing a therapist might help you sort through these feelings. You’ll want to look for a sex-positive professional and be upfront in your initial calls about wanting help for this particular issue. You might even ask how many sessions they think you’ll need to see progress.

Riffing off the porn thing, have you tried leaving the lights on and strategically using one or more mirrors? And could you replay clips in your memory? How about masturbating to memories of partnered sex instead of porn? The idea here is to figure out the boundaries of this, so you can better decide how to approach this. You can also eliminate porn use for a period of time, like a few months, and revisit the issue when you’ve had a chance to see if that changes anything.

The timer detail strikes me as very useful—especially if you and your partner go into it with the intention of giving you pleasure for that entire period of time, regardless of whether you orgasm, get close to orgasm, or experience one twitch of your left calf.

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As for toys, although you can absolutely habituate yourself to a certain sensation, I don’t think the vibrations inherently desensitize. And while you’re correct that quality sex toys can cost upward of $100, they tend to last for multiple years when treated well. If your plan is to incorporate vibrators into partnered sex, take care to choose something that’ll be easy to hold on to when slippery and is small enough to slot between your bodies comfortably.

Did you write this or another letter we answered this year? Tell us what happened at howtodoit@slate.com.

Dear How to Do It,

I’ve been with my partner for more than four years. I do love them and am very happy with almost everything. They like to have sex, and frankly I don’t. I’ve done it before early in the relationship, and I still do it because that’s what you do, but I’ve never been a fan. I don’t even like to masturbate, and porn makes me uncomfortable.  I don’t know if it’s because I’m fat and hate everything jiggling about, making me self-conscious, or because I lost my virginity late in life and am embarrassed, or I just genuinely don’t like it and am making up these excuses. Either way, I don’t know how to say, “I hate sex, but we can have an open relationship” because they’ve made it clear they doesn’t want it open, especially after their ex cheated and said that they thought the relationship was open. Am I stuck? Do I just suck it up and keep pretending to enjoy sex? Is something wrong with me for not liking sex?

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—Can’t Afford a Therapist but Maybe Asexual

Dear Maybe Asexual,

Some people like sex a lot. Some only like sex under specific circumstances. And others don’t like sex at all. Wherever you fall on the spectrum is perfectly fine. Keep in mind that sexuality is pretty fluid and may change over time, whether that’s you becoming more sexual or less sexual or identifying more as lesbian and then more as bisexual or queer.

I hear, in your chosen sign-off, that you can’t afford a therapist. There’s a book by Angela Chen called Ace: What Asexuality Reveals About Desire, Society, and the Meaning of Sex that you might find helpful. It contains personal sharing from a variety of people who identify as asexual, and may help you decide if that label feels right for you. Journaling also might give you a space to express and sort through your feelings around your body, sexual experiences, and sex in general. Anecdotally, writing does seem to work better than typing for people. You can always shred or burn the pages afterwards if you’re concerned about privacy.

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Regardless, please don’t keep sucking it up and pretending. I imagine that you feel pressure to fulfill the socially conditioned role of life, romantic, and sexual partner. You don’t have to be all of those things. You don’t have to be someone you aren’t.

An open relationship can be structured in a variety of ways, including open for your partner and closed for you, the person who isn’t interested in sex at all. I think it’s worth having a direct conversation with your partner about where you’re at on the subject of sex and asking them if they’d consider trying ethical non-monogamy with that arrangement. Regardless of whether you decide to float that option, your partner needs to know that your heart isn’t in the sex you’re having.

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Dear How to Do It,

I am a senior woman in a long-term marriage (50 years). I have stayed in this marriage for less-than-optimal reasons: We own property together and have no other assets. If I leave, my husband could not afford to keep the property and our two adult kids would basically be shit out of luck with any inheritance. I feel I owe them to stay here and “keep my claim,” so there is something to inherit. At the same time, I feel like my life is ending soon and I will spend my last years with a man who is selfish and self-centered and would probably hook up with the first woman who looked at him if I wasn’t around. There has not been any real understanding or attraction between us for many years. Can I really make a new start at my age? And just how much do I owe my beloved children?

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—Old, but Not Dead

Dear Not Dead,

I’m a sex columnist, so I’ll start with the parts of your letter that are topical to that.

You seem to be concerned about what your husband might get up to if you’re no longer in the picture. And it sounds like you resent him for past, present, and potential future behaviors. Without understanding or attraction, the relationship appears pretty hopeless. You have to decide for yourself how much you’re willing to tolerate. Are you OK with another year of this? Five more? A decade?

Plenty of seniors make new starts, whether that’s after a divorce or after the death of their partner. You can absolutely do the same. You’ll want to think about what you want—what you’re missing now can hold a lot of useful data—and look for people who exhibit qualities that make them likely to provide what you’re hoping for. It’s worth spending time thinking through, either on your own (journaling could help) or with a therapist. It might also be worthwhile to book a consultation with a divorce lawyer to talk through your options.

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Your children are adults. That implies to me that it’s possible to have a mature conversation with them about how much they value the property you refer to. You don’t have to disclose that you’re thinking about leaving your husband, but you can get an idea of whether they’re attached to it. You can also trust your children to take care of themselves financially and make good choices. An inheritance is nice, but certainly not something one should expect or count on.

—Stoya

More How to Do It

I’m a guy in a relationship with another guy. I’m late 20s; he’s pushing 40. It’s been about nine months. We get along well, and our sex life is totally normal from my perspective—maybe not off the charts, but loving and frequent. We’ve shared fantasies and desires, and I thought we were roughly on the same page. The other day, with his permission, I was working on his computer at his apartment while he was at work, and I noticed an image on his desktop that looked like porn (he has a machine where image icons display with previews). I clicked on it. It featured what looked to me like two preteen boys having sex. The lighting looked professional, so I’m wondering if it was a scene designed to simulate underage boys having sex that actually depicted adults, but I have no way to be sure. I’m very disturbed by this. The boys in the image looked very, very young. If he had that on his desktop, I can only imagine what I’d find if I looked further, which I haven’t. Should I ask him about it? If so, what should I look for in his response? I’m worried I discovered something very dark about my partner, and I don’t know how to proceed.

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