How to Do It

I’m a Female Virgin, and I’m Looking for a … Very Specific Quality in My First Lover

A young woman next to a peach emoji.
Photo illustration by Slate. Photo bycurtoicurto/iStock/Getty Images Plus.

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 female virgin in my late 20s. I’ve always had a strong aversion to the idea of sex, but I definitely am not asexual, and I enjoyed kissing, etc., as a teenager. But I haven’t dated as an adult because of worries about expected sexual relationships. My aversion extends to any type of penetration—I’ve never been able to use a tampon or insert a finger into my own vagina. (I get myself off by rubbing my clit through my clothes.) I assume there’s a hole there because the blood’s certainly coming from somewhere, but I couldn’t tell you how to find it. Recently, I’ve started to wonder if I’m actually sex-averse, or just averse to being penetrated. Sucking dick or eating someone out seems a little gross, but I don’t have the same visceral negative reaction that I do to the idea of vaginal sex. What has been really intriguing to me is the prospect of actually being the penetrative partner myself—presumably with a strap-on, because sticking a finger in someone is almost as unappealing to me as having one stuck in me. I’m wondering whether this is a common thing—cis women who want exclusively to penetrate—and how on earth I go about finding people who would be, ah, receptive. I’m not interested in casual sex, and it feels like a very personal thing to disclose upfront, but it also seems troubling to get several months into a relationship and then be like “so by the way, I’m only up for pegging.” Or am I overthinking this whole thing, and I should just try dating and cross the sex bridge when or if I come to it?

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—No Admittance

Dear NA,

Right now, you’re looking for a very specific person to fit boundaries and interests that are untested. You—and your partners—should adhere to your boundaries, and your interest should dictate what you do. You might find that certain people inspire desires for acts other than pegging, or that over time you become curious about penetrating a person with your fingers. Whether you do or not, your sexuality is beautiful.

There are absolutely cis women who only want to penetrate, not be penetrated. You don’t mention what sorts of people you find attractive, but you do use the word pegging, suggesting that you want to penetrate cis men, which realistically may be a little tough to find a partner for exclusively.

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Do you fantasize about any particular context for this pegging? Can you see any details about how pegging intrigues you? Is there a power dynamic in one direction or the other? Do you think you’d enjoy seeing your partner experience pleasure? Being able to clearly articulate what you’re hoping for will help you describe what you want to potential partners in a way that feels less limited than “only up for pegging you.”

Is it possible that you might feel comfortable disclosing your sexual desires somewhere between “upfront” and “several months in”? Like, several weeks? That seems like a happy medium to me—long enough that you will have time to get to know the person and feel whether you want any sexual interaction with them, but not so long that they’re likely to feel they’ve been led on. You might consider starting with your interest in exploring your sexuality, emphasizing the fact that you’re beginning this process in a grand sense. Enjoy your journey.

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Dear How to Do It,

I’m a 30-year-old woman who has always been interested in kink, and I have been very lucky to start dating a younger man who I find immensely attractive, is bisexual like me, and is a switch in the bedroom. However, he recently confessed to me that his biggest kink is ABDL—adult baby/diaper lovers—and he’d like me to occasionally take a “mommy” role in the bedroom. I never thought of myself as judgmental when it comes to kink, but I’ve found myself wondering how I can become OK with the idea of seeing the man I love in diapers and bibs. It definitely doesn’t arouse me in any sense of the word. I don’t think everything partners do in sex needs to be equally gratifying for both, and I want to be the person he comes to for satisfaction in this regard. Is there anything I can do to Pavlov my brain into finding this at least appealing?

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—Mommy Dearest

Dear MD,

Let’s think about your desire to be the person your partner comes to for his ABDL fulfillment. Why do you want this? Is there some sense of empowerment you feel you’ll derive from the role of “mommy”? Or joy from successfully catering to your partner’s carnal cravings? It’s worth spending some time examining your feelings and motives here, and you’ll probably find a mix of emotions. I’m hoping that one of the reasons you want to satisfy your partner’s sexual longing can help you figure out your path to accessing the “scene.” And you may find that once you’re engaged in the play you find facets that are arousing for you.

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Another thing you can do is get more information from your partner. What does he yearn for? Is it a safe person to fully unleash his inner child around? Does he want an element of domination? Are there themes of punishment, or solely of care? Is it the sensations of the diaper and bib? Does it simply turn him on and he isn’t sure why? As with your reasons to want to engage, there will probably be a mix of pleasures and goals on his end. And I’m hoping that more detailed information from your partner will show you a path to enjoyment.

Once you find some facet that appeals to you, take your time. If you enjoy having your breasts stimulated, that’s a likely good place to start. If you enjoy being dominant, and he wants that from you, there’s another good starting point. And once you start, you may find that your partner’s pleasure brings you enough to begin the Pavlov process.

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Dear How to Do It,

I am an early-60s woman in a two-year relationship with an early-70s man. We are youthful and keep very fit, and we share a very beautiful, sensual, and loving relationship. He is the most wonderful and attentive, romantic lover I’ve ever been involved with. We are very sex positive, very sexually compatible with great chemistry and great communication.

He has never had an issue getting hard—the problem is that he has never orgasmed once with me. He had been in a very long-term marriage, of which the last 20 years were sexless. During that time, he used porn and masturbation as a release. Now that we are together, he still masturbates to porn. He was very upfront and honest with me when we met that he probably couldn’t orgasm during sex. I know that orgasm isn’t the end-all-be-all, I get that. We occasionally discuss it, but I don’t bring it up too often because I don’t want him to feel pressure. I do believe him when he tells me he loves our sex life. I just can’t help but feel a little bad because I want to be able to give him that pleasure. We have talked about him laying off the porn for a while to see if that helps, but at this point, I’m pretty sure he’s addicted. We even tried to have him watch porn and masturbate with me, but it didn’t work. Should I just leave it be, or is there another way to have him orgasm with me?

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—Too Mature?

Dear Mature,

Has he tried edging? Edging is a masturbatory process where the person brings themselves to the brink of orgasm, pauses to let the build-up fade, and brings themselves to the brink again repeatedly. I’m wondering if a few days of him teasing himself with his typical porn use might get him to the point where he’s wound up enough to orgasm with you.

You’ve already thought of the other two things I would have suggested—ceasing porn use and incorporating porn into sex. (You can read about porn “addiction” here, by the way, and some strategies to help stop if he wants to try again.) It’s possible that he can only orgasm with himself at this stage. If that’s the case, you may be best off letting it be.

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We’ve all internalized messages about the value of orgasm, and even if we know with our minds that it isn’t the goal, we can still feel disappointed or somehow less-than when we aren’t able to help our partner have one. And that disconnect between what we know and what our emotions are doing can be upsetting in its own way. You might ask your partner what he gets out of sex with you. Make a list to refer to later. Does he enjoy giving you pleasure? Does he experience pleasure from having a whole part of his body—his penis—buried inside of you? Is there some connection and sense of intimacy that he derives from your sexual interactions? When you’re feeling down about the orgasm issue, you can refer back to that list of the ways in which you do give your partner pleasure. What you have sounds lovely.

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Dear How to Do It,

So lately, I’ve noticed that after I orgasm from masturbating, I feel pretty sad. It was not always this way, and I’m not sure what to do about it. In my previous relationship (I’m a straight woman), my ex and I never had sex. This was not what I wanted, but he had a health issue where he could not get hard, so I was patient and masturbated to deal with my desires. Eventually things fell apart for other reasons, and I essentially had not had sex for almost two years. I’m now in the best relationship of my life (only six months in), and my boyfriend and I have the best sex of my life. I feel like I’m a virgin all over again. But now when I masturbate to try and enjoy solo time, I feel sad! I was starting to feel sad prior to this relationship when my sex life had been reduced to me and my toys. Now, though, I’m sad after I orgasm because it makes me miss my current boyfriend. I want to be able to pleasure myself without this happening. Any ideas?

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—Mastur-hatin’

Dear Mastur-hatin’,

Let’s dig into the sadness. Next time you masturbate, when you get that sad feeling, sit with it and try to understand the more granular emotion—in your case, it sounds like loneliness. Let yourself experience the emotion and see if any clues as to why come up. Try masturbating with your boyfriend, too. Have him watch or hold you—if both sound acceptable, do each—and see what you feel like after you orgasm. Is there sadness then? If so, listen for more information.

It’s possible that after a few years of solo-only, you’re craving connection and interaction. You might find that you’re happier engaging only in partnered sex for a while. It’s also possible that you’ve got some beliefs about what sex should be and are feeling negatively about your solo time because you’ve got someone you could be having partnered sex with. That’s worth examining and untangling. It’s also possible that you’re high on happy-new-relationship chemicals and are wanting snuggles afterward. If that’s the case, you might curl up in a ball of blanket after you orgasm to get a similar enclosed-by-warmth feeling.

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If you’re having difficulty hearing your feelings, you might try journaling, taking a quiet walk, or getting in the shower. Of course, if you have other ways of sorting through your emotions, you’ll want to make use of those. You’ve got this.

—Stoya

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