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 am an 18-year-old female high school senior living with my mother and stepfather. I am a serious student, get excellent grades, participate in school activities and have friends. My biggest problem is boys. I can’t seem to connect with one. I think that I intimidate the good ones. The few who have asked me out are too lame for me and rather than spend a boring evening with them I send them away. Most of my friends have or have had boyfriends, but I am still a virgin. I’ve been told that I am cute and sexy so it can’t be that. I worry that if I do find someone I like, I won’t know the first thing about what to do. I’ll come off like some amateur and they will lose patience and interest in me.
I got an idea that I know will sound totally crazy, which was to have my stepfather teach me. He is supportive and understanding, and provides well for my mother and me. When I first brought it up with him, he was adamant he would not even consider it. I pestered him and I guess he thought it over because he finally agreed, but only with strict conditions. We would not go all the way. Instead, we would go step by step. Either one of us could call a halt at any time with no pressure. I set the pace. And we would never, ever tell anyone else about it.
We started about a year ago when he taught me how to kiss. I had kissed boys before, little quick ones, but never like that. I wanted to keep going, but he hit pause. Since then, I have gotten more comfortable with our arrangement and have wanted to speed things up. He always tells me to be patient and take the time to think it over. But by now we have done just about everything except have actual intercourse.
I worry that taking this last step will change things in a permanent way. I can’t deny that I find my stepdad attractive, but I don’t lust after him. He and my mom have a loving, affectionate relationship which I am not jealous of. But if we have sex and it is awesome, maybe I will start to want him. And he has told me things about how boys and men think about women. (All the boys imagine me naked and in bed with them? ALL of them?) I don’t want to lose him as a trusted source of intelligence from the other side.
If we stop now and if, God forbid, we are ever found out, at least we could say that we never had real sex. I would die if Dad ever got in trouble because of me. But we have done so much already, would it really matter if we did just one more thing? Also, I have become something of an expert on things that not even my girlfriends have done. Suppose some future boyfriend wants to know where I learned how to do all this stuff. I will have to lie about it. I’m going to school next year where I have been assured that there are smart, interesting men. Maybe I should quit while I am ahead.
I’m just so conflicted. I have no regrets so far, and I’m really tired of being the only girl in the Virgin Club. But there’s something about actually having sex with my stepfather that I don’t think anyone else would ever understand. I’m starting to think that this whole thing was a major, major mistake. Am I going to hell?
—At Cliff’s Edge
Dear At Cliff’s Edge,
Taking your incest-adjacent issues to an advice column for sorting out is like taking your Gulfstream G150 jet down to the local Grease Monkey for servicing. Some things, like a therapeutic process and determining who goes to hell, are just beyond my job description. And I want to be upfront with my suspicions regarding the veracity of this letter—it reads like incest erotica, and it seems designed to make outright condemnation difficult. However, I am nonetheless willing to take this on as a thought exercise, if nothing else.
Beyond the tangle of ethical issues—including the framing of this as all your idea that has been met with protests and a seeming lack of overt coercion on the part of your stepfather—there are some glaring moral infractions that no amount of humanizing detail can rectify. This is a sexual relationship with a very clear-cut disparity in power. He is more than a mere father figure; you call him “Dad.” You’ve already demonstrated the effect this is having on your burgeoning sexual psyche, as he has told you things about men that are, at most charitable, distortions. He is at this point a biased source and cannot be fairly trusted regarding how sex works. You describe the premise of this arrangement as educational, but gestalt of a stepfather-stepdaughter relationship is so outside the realm of typical sexual development as to present you with a warped and impractical understanding of sexual dynamics. This is especially troubling for someone who, while legally of age, has yet to fully develop mentally and emotionally. It’s your parent’s job to know this; he has failed. Further, this is a tremendous betrayal of your mother.
So much damage has potentially been done already that it seems useless to fret about what might happen if intercourse takes place. That is an arbitrary designation when Pandora’s box is the centerpiece on the mantel in your family room. Now, one might argue that the taboo at the heart of this question is also arbitrary in a vacuum, or at least so socially constructed that it’s foolish to accept without interrogation. “If gay sex is OK, how can incest be wrong?,” William Saletan rhetorically asked in a 2010 piece for this very site. He was responding to the news that a Columbia professor had been charged with incest for having a sexual relationship with his of-age daughter (he later pleaded guilty to misdemeanor incest). Saletan reasoned that the presence of consent and lack of reproductive intent required an explanation of what separates the taboo of familial sex from other forms of supposedly deviant sexual contact that are acceptable to an enlightened liberal mindset.
Saletan ultimately resolved that incest is a cancer on family. Not “the family” as it exists in the abstract to the right, which has consistently characterized it as being under attack as means of social control, but one’s own family unit in which said incest is taking place. Here’s where he brought it all home, as it were:
By definition, [incest] occurs within an already existing family. So it offers no benefit in terms of family formation. On the contrary, it injects a notoriously incendiary dynamic—sexual tension—into the mix. Think of all the opposite-sex friendships you and your friends have cumulatively destroyed by “crossing the line.” Now imagine doing that to your family. That’s what incest does. Don’t take my word for it. Read The Kiss. Or the sad threads on pro-incest message boards. Or what Woody Allen’s son says about his dad: “He’s my father married to my sister. That makes me his son and his brother-in-law. That is such a moral transgression. I cannot see him. I cannot have a relationship with my father … ”
I don’t think it’s right for me to impose a diagnosis here, particularly when it has not been solicited, and more generally because you know more about your emotional state than I do. I do think that many professionals would characterize your sexual relationship with your stepfather as abusive, and I’m certain none would endorse its continuation. If you really are a person out there in this situation and not someone who needs to seek out a better creative outlet, find a therapist and start listening carefully.
Dear How to Do It,
I’m a 30-year-old lesbian trans woman, and I am THIRSTY. I haven’t had a relationship in almost a decade, long before I even considered transitioning. At this point, after half a decade of hormones, I’m happy with my body, but I’ve had trouble finding relationships. One factor I feel really guilty about is most of the attention I get on dating apps is from other trans women whom I just don’t find attractive. In general, I really prefer to date people who are assigned female at birth, because cunnilingus is the main thing I’m interested in performing sexually. But at the same time, I feel like a piece of shit for that preference, like I’m perpetuating the same kind of transphobia that’s limiting my dating options in the first place. On the one hand, I feel like I should try to be more open-minded and try to explore the full spectrum of sexual experience that’s available to me. On the other hand, I don’t really feel like I’m really interested in the experiences that are available to me, and I’m not sure how to express my preference in a non-hurtful way. This is a tough area for me to talk about since there’s obviously a lot of ugly opinions out there about trans genitalia, so this is understandably an area of conversation where it’s easy to stumble on different rhetorical landmines. I’m not really going to stand for bullshit heteronormativity inside my subconscious, but on the other hand, it feels very much unqueer to start dating people I’m not attracted to just because that’s how I think I should feel.
Dear Confused Queer,
It’s not just unqueer to start dating people you aren’t attracted to, it’s inhumane. You have no obligation to do anything you aren’t comfortable with, and you, in fact, do yourself a disservice when you enter that realm of self-imposed discomfort. (Not to mention your partners, who likely want the person they’re having sex with to want to have sex with them.) The pursuit of happiness is a human right. However, negotiating our own interests with the greater world and determining whether we’re contributing or taking away is the very foundation of social consciousness. This is not something one can achieve by ticking a few boxes. It’s a process.
There is no consensus on how sexuality is formed (I believe it owes to a number of potential biological and cultural factors that are inextricable and received differently by different bodies), which makes the prospect of intentionally altering it dicey if not altogether doomed (see the failures of conversion therapy). For some, sexuality does seem to evolve, though when it does, the question remains whether that evolution amounts to actual change in desire or the uncovering of something long dormant. So the best you can do is to keep an open heart and mind while remaining true to yourself. I know I just stacked platitudes on platitudes, but those are the language of broad concepts.
The reason why this stuff is hard to talk about is because sexuality is not rhetorical or necessarily rational. Willing your sexual interests into presentations approved by social media and other cultural forces is an absurd undertaking and a losing game. Sexual and verbal communication can operate as two entirely different languages, and there is often something lost in translation, hence the “rhetorical landmines” you reference. But participation in this discourse is not mandatory. You can give yourself time to sort out seeming contradictions before explaining them, if you elect to share them at all. In other words: You don’t have to let this hold you back from dating.
Don’t feel bad about your strong urge for cunnilingus. Do continue to interrogate your desires as they relate to the status quo. Expressing your preference in a nonhurtful way is the trickiest facet of your question—as you recognize, this can be a sensitive topic, and some sexual rejection may feel like discrimination, and some rejection is discrimination, objectively speaking. (It seems clear that what some people—especially on apps—call “preferences” are actually just bias, though intent and deeply held beliefs are often impossible to discern and in many cases come down to one person’s word against another’s suspicions.) Approach those to whom you are attracted, and don’t engage with those whom you aren’t. Exercising the latter can run the gamut from polite but telling terseness, to slow responses that telegraph the conversation is not going anywhere, to not saying anything at all when contacted. A not-quite-golden but ever-present rule of dating apps is that no answer is an answer.
Dear How to Do It,
I’m a straight man in my mid-20s, and I have never had a problem getting or maintaining an erection either by myself or with a partner. Recently I have begun seeing a girl, and things are going really well. I have no problem getting an erection or ejaculating when I’m sleeping with her.
However, I am struggling to get one when I’m NOT with her physically. Because of COVID and me being busy at work recently we aren’t able to see each other all that much, and even within that finding the time to be intimate is a struggle. We try to keep our sex life alive through more long-distance means, like Skype. However, recently even with that I am only really able to become semi-erect. My fear is this will bleed into our actual sex life, and I will struggle to get an erection when with her. Our sex life is so limited at the moment, that would be a huge blow.
—Reverse ED Guy
Dear RED Guy,
You won’t know that you have a problem getting an erection with this woman until it happens, so try to relax and focus on the fact that you do not yet have an issue here. Anxiety can contribute to erectile dysfunction, so anything you can do to assuage it will help. Our bodies don’t always exhibit a logic that makes sense to our minds, but there is a wide range of potential responses to sexual stimuli. Screen sex might not be your thing, and if that’s the case, your lack of sexual response is no comment on your relationship or partner, but a resistance to the medium through which you’ve attempted contact. That’s not a problem; it’s just something to cross off a list.
But the wording of your letter made me wonder if you’re having a hard time achieving an erection by yourself when not in a screen-sex scenario. This, too, is not yet worth worrying about if you’re functioning typically in other contexts. Nothing is lost when you don’t masturbate out of a lack of interest, and in fact there is something gained: time. If you want to be safe, bring along some cock rings or ED meds to your next in-person session.
Dear How to Do It,
I’m a young trans man who recently started testosterone, and I have a couple questions. Before I start, I want to state that I’m dating an ace person I love dearly, that they prefer that we be monogamous, and that I prioritize my relationship with them over my issues here, so I’d prefer to solve these without any recommendations for partnered sex.
That said: I’m confused that my body doesn’t seem to process pleasure normally. I read a lot of erotica, especially by other trans men. Touching myself anywhere ranges from vaguely uncomfortable to sort of gross, even when it’s not being affected by dysphoria. Even fondling my bottom growth feels more like rubbing a healing wound than anything I’d classify as nice. This is an ongoing problem since before I started T, but I kind of hoped that it might help, based on the testimonials I read from others about libido increase. My libido has increased, but this problem has not gotten any better. I do get aroused, though, hence the frequent reading of erotica. That does feel good. But when I try to do anything about it physically, it gets unpleasant fast. The sexy feelings that I read about translate into just feelings of pressure and sometimes scraping, unpleasant tingles and squelches. And before you ask, yeah, I’m sure I’m not ace myself. I feel sexual attraction and arousal, and I definitely have a libido too; this seems to be a physical thing. It makes me unhappy. At this point, I’m considering that when I go into my Planned Parenthood for my next round of testosterone bloodwork that I ask them about it. But that isn’t for a month, and, please forgive my language, but I’m getting fucking tired of this. Any advice? Even just that I’m on the right track?
—Trans and Tired
Your curiosity and experimentation suggest that you are indeed on the right track. For help with this question, I reached out to Gaines Blasdel, a New York–based trans community worker who runs the resource website Healthy Trans. Blasdel told me by phone that what you’re experiencing is common, particularly at this point in your transition. “It’s super common for people right after they start testosterone to have clitoral growth or genital hypertrophy, which can translate to pain and discomfort as the tissue is mechanically stretching,” he said.
Your issue here predates your going on T, but testosterone is not a cure-all. It’s a series of shots, not a magic bullet. Blasdel explained that the body’s response to testosterone ranges: “Sometimes hormones help people feel more comfortable in their body, but not everyone.” Blasdel told me that for months after starting T, he found himself unable to reach orgasm. “Trans people say their orgasms change after they start hormones, so it can take time to click with what your new orgasm feels like,” he said.
That you’re checking out erotica by trans men is good, but Blasdel warned against comparing your response to that which you’re reading about—masturbation that works for one trans man may leave another cold. Time and patience are key here. Definitely talk to your hormone prescriber, though, about your issues—especially your pain, as Blasdel reminded us: “Any genital pain should be evaluated by a primary care provider.” That’s true for everyone, regardless of gender identity. Good luck!
More How to Do It
I’m worried my friend actually believes she has been having sex with a ghost in quarantine. I’m quarantining with my partner; she’s quarantining alone. We’ve always been close, but we’ve talked especially frequently during this time, because she lives far away from family and doesn’t have a lot of close friends. In a conversation in April or May, she mentioned to me that she’d been masturbating while thinking of a man who lived in her apartment in the 1920s. I assumed she meant it as a fantasy, and we had a good laugh. But in subsequent conversations, she named the man John, and she’s begun referring to him when I mention things my partner has been doing, like her stories are complementary: John said this, John did this, John is having a bad day. She mentioned possibly seeing an old sex partner again, but said she’s worried John might get jealous. I can’t tell if this is harmless or if I should have a more direct conversation with her about it. What do you think?