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 work in social services. I’ve taught seminars on healthy relationships and consent. I ran my high school GSA for years and did peer sex education work. And I’m still a virgin well into my 20s. I know, I know, you probably get a lot of these messages, and 25 is hardly 40. But I can’t help but feel like I’ve backed myself into a corner here. I lost my high school years to mental illness and COVID hit when I was in university—and I’m high risk so that’s still a factor even now. I just don’t know where to start at this point, and I’m all wrapped up in the thought of it for reasons I can’t put my finger on.
I feel like there’s an expectation that I, being the hot leftist butch with her life moderately together that I am, will be at least somewhat sexually experienced at this age, and I’m not. The thing is that I’m not worried I’ll be bad at sex. I’m a good listener, I’m adaptable, and I’m a lesbian, so I obviously know my way around at least one vulva. And besides, even if I end up being only vaguely alright in bed, it’s not like I’m gonna beat myself up over it. But I feel like I’ve got a complex about my virginity that I can’t get over, and I have no clue why. My family isn’t religious or conservative (my mom’s literally got a shelf for all her books on sexuality with The Ethical Slut front and center). I’m obviously not anxious or awkward about the concept of sex and I don’t have a problem talking about it—I’ve supported friends and clients who have been in the exact same boat! But it feels so different when it’s me we’re discussing.
Any advice on how to shake this? (Oh, and what are the ethics on not telling potential partners you’re a virgin? I’m happy to vaguely say I don’t have much experience, but the reasons I don’t have any aren’t something I really want to discuss with a hookup.)
—Overqualified and Underexperienced
We do get a lot of these messages, including from people older than 40. One way to approach this is to step in slowly. Whatever your current sexual experiences are, how far outside of them are you comfortable thinking about? Rather than aim to dive directly into the thing that overwhelms you, look for the zone that is unknown but feels manageable. Know your boundaries, and lead with what you do want to engage in at this time.
Another angle you might start from is reaching out to someone with similar experiences and letting them know that you’re wanting some counseling of your own. Talking about a potential experience in detail can be a kind of dress rehearsal. You also might sign up for a couple of apps and look for people who list sexting in their interests. Finding someone who might be interested in sexual engagement through messages, gives you the opportunity to interact sexually with the single input of written words. You can see what develops from there.
Experience confers two main benefits—data, and confidence. You’ve got a lot of data on anatomy, and you probably know several methods of communicating about desires, boundaries, and what feels good. Even the most experienced of us have to start from scratch when trying to understand what works for a new partner. Confidence will come with practice.
Regardless of whether you use the V word—loaded as it is with the weight of heteronormativity and sexism—or go with a vague statement that you have little experience, you should expect follow-up questions. I’m guessing your mental health is a significant aspect of what you don’t want to get into discussing with hookups. Think in advance about how you’ll express your boundary around going into details regarding why you lack some experience. Do be prepared to share a basic sketch of what you have and haven’t engaged in. For instance, if you’ve never been penetrated, including with your own fingers or a toy, that’s relevant information for a partner to know before you ask them to engage in it. Your high-risk status with regard to COVID is also important to communicate, for your own safety. You’ve got this—it’s going to get easier.
Dear How to Do It,
I have a toddler and am now five months pregnant and single. I’m in the midst of grieving that relationship and overwhelmed with my life responsibilities, but managing and moving forward as we all do. My dilemma: I’ve operated as a heterosexual for my entire sexual life (15 years) but have had recurring lesbian sexual dreams for the same amount of time and I’ve only ever watched lesbian porn. In real life, I’ve never done more than kiss a woman. But as of late, I’ve been particularly attracted to women.
The type of woman I’m attracted to is lipstick femme. I am not the pursuing type, ever. I’ve been on the receiving end of many compliments from women but I’ve never taken any further action besides a polite “thank you.” My dreams have become more incessant and I’m finding it hard to accept going six to 12 months (during and post-pregnancy) without exploring this. Where do I even begin? I have no interest in investing more time and money in a therapist than I already have. But I can’t imagine walking into a gay bar pregnant. My other concern is: How do I not freeze up during a first encounter? Do I accept my state and remain in fantasy land for another year or longer or give myself a bit of delusional hope that a lesbian I’m attracted to would also be attracted to me right now?
—Beached Whale at the Gay Bar
Dear Gay Bar,
Between the emotions related to ending a relationship and the responsibilities that are overwhelming you right now, it’s worth considering how much chaos—which is often part of hooking up or dating—you want to invite into your life. Your least volatile course of action would be to continue fantasizing about sex with the kind of women who turn you on and put all that erotic energy into masturbation.
Another part of sexual relationships is putting ourselves out there in some way and navigating a range of interactions from wonderful to painful. Walking into a gay bar while visibly pregnant is one of the most extreme examples of this that I can think of. You absolutely might experience reactions that are uncomfortable. But you also might encounter the lipstick femme of your dreams, who prefers to take the lead in flirtation, is specifically interested in you, and is actively aroused by pregnancy or some closely associated concept. More likely is that your experience would be somewhere in between.
I get the sense from what you’ve written that your interest is purely physical and sexual at this stage. Presuming I’m correct, a dating app—or a few—is worth considering. Most allow you to set your preferences so you are only shown to profiles of certain genders, and vice versa. Almost every app, though, will require you to take some initiative by swiping yes on profiles of people who you find interesting. There is a chance you’ll spend a year swiping. Photos aren’t required, but they do tend to be effective and should show you as you currently look. The more upfront and direct you are in your profile, the easier it’ll be for people to decide whether they’re interested in you at this time. Be clear about the boundaries of what you’re looking for. Whether you list this on your profile or not, do let potential partners know what your experience level with women is. And once you’re engaging in sexual contact, go as slowly as you need to go—and as they need to go—and remember that you can stop at any time.
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Dear How to Do It,
Due to significant sexual abuse as a child, I cannot have sex at all. I could maybe just manage kissing but otherwise, it’s just cuddling (I think I may be demisexual/biromantic regardless but it’s so intertwined with the trauma that it’s hard to know). I would still very much love to have partners (I’m poly) and children but I have no idea how to go about explaining the above or whether anyone would want me, especially because all forms of kink are also triggering.
—Scared to Explain
Dear Scared to Explain,
You don’t mention whether you’ve used therapy to work through the abuse you’ve experienced. If you haven’t, and are in a position to do so now, it’s worth looking for a therapist who is either already ace-aware or willing to do some research. The identity labels you eventually choose are your decision. Those labels might shift as your understanding of yourself deepens, as you grow and change, and as language evolves. And our identities are multifaceted, sometimes overlapping and sometimes influencing each other. So, try not to worry too much about neat categorization.
Sex educator Aubri Lancaster, who focuses on asexuality and aromanticism, says the answer to your question of whether anyone would want you on your terms is a “resounding YES! There are so many people out there of all genders who do not center sex in their relationships. It might be harder to find them, but being Polyam means they already embrace the idea that they don’t have to be everything for their partners and they can center the emotional, sensual, intellectual, and other forms of non-sexual intimacy in future relationships.”
“Partners” leaves a lot of room for interpretation. Are you looking for people to raise children with? Do you have a sense of whether you’d prefer that parenting take place between a pair of biological parents, in a polycule, or as a largely single-parent endeavor? What sorts of emotional support and caring do you want to give to and receive from your partners? Would you like to cook together? Watch shows or theater? Engage in sports or tabletop games? Go on classic dinner dates? Spend some time thinking about what you’d like your romantic relationships to include.
You should also consider non-sexual touch and what it might look like with future partners. Would you like to cuddle on the couch? Spoon in bed? Hold hands? And what’s your interest in activities like a massage? The more you can describe what you are interested in, the easier time you’ll have communicating those desires.
As for how to explain yourself, decide how much detail you’re comfortable giving about which subjects and go from there. You might start with “I’m into romance and somewhere in the range of asexual identities,” and have a conversation. As you gain experience discussing your desires and boundaries, you’ll likely feel more at ease having these talks. Be prepared for negative reactions, and stay open to the people who are interested in learning about you and seeing how you fit into each other’s lives.
Dear How to Do It,
My wife and I have been together for nearly 10 years, married for four (in our mid-30s). Our sex life has gone through what seems like normal ups and downs but recently has been on a big up. With a now 18-month-old, pregnancy, and post-pregnancy we basically had no sex, but now we’re having sex almost every other day, more than we ever had, even when we first started dating. The sex is great and seems to be the best we’ve ever had. However, I get hung up on one thing. I always finish, however my wife never has. Never in her life. She doesn’t masturbate and claims she has no desire to. During foreplay on her, generally fingering, sometimes oral, she gets really into it, but before it gets too far, she always just wants me in her. We bought a vibrator to play with, but she will only incorporate it into our foreplay if I insist and recently admitted when we use it she feels like she’s getting a medical procedure and doesn’t get turned on by it. She says the sex is great and there’s no reason for me to be concerned about her not finishing but I never feel like
I can get it out of my head. Any advice for me and/or her?
—She Doesn’t Cum
Dear She Doesn’t Cum,
Your wife says the sex is great as it is, yet you’re hung up on what you describe as “finishing.” Orgasms, enjoyable as they are for many of us, aren’t something everyone wants. Nor, despite the template most mainstream hetero porn adheres to, do they have to be the punctuation at the end of the sentence of sex. You can have sex without orgasm. You can orgasm and continue to have sex. You also say she “claims” to have no desire to masturbate—a word that often carries a connotation of doubt or suspicion. Whatever the disconnect is that’s preventing you from believing your wife, about her sexual desires and level of satisfaction, that’s where you should focus your effort.
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I am a 55-year-old single straight man. I have a partner of several years (same age), but we live in different homes, I have kids, she doesn’t—we are in different bubbles. We do walks and talk in person, but no physical contact. She is not into online sex between us, and I am OK with that. I discovered online live adult entertainment on a cam site. It is fun, but expensive. Mostly I watch and chat, but it got kind of hot and heavy with one particular person online. Let’s say that what took place on either end, while pretty vanilla, would not be fare for PBS. There was also one private session. I should add that my partner is not aware of these recent online activities, and would probably be really pissed if she found out. To get to the point: A couple of days ago, I got an attempted extortion letter.