Our advice columnists have heard it all over the years—so we’re diving into the How to Do It archives to share classic letters with our readers. Have a question? Send it to Stoya and Rich here. (It’s anonymous!)

Dear How to Do It,

I’m a very, very masculine cis lesbian (been on hormones for years), and while I have a sex life with other women that I’m very happy with, I have this major problem.

I know this column has talked before about how unlikely it is to change one’s sexual fantasies, but what about when those fantasies are unwanted? A not-insignificant number of my masturbation fantasies revolve around a former (cis male) partner. Our relationship occurred before I was out or transitioned at all, and was generally unhappy for me. He was clingy, pushy about sex, was very bad at taking no for an answer, and generally made me feel bad about myself.

He was also the only person I ever dated with a penis. So whenever I fantasize about having sex involving a penis, there he is. In the moment this is fine, but afterwards I’m flooded with guilt and shame and stuck feeling just as bad about myself as when I was with him.

I think this wouldn’t happen as much if I had other sex involving penises, but all my current partners are cis and I’m not interested in casual hookups or new partners to get the experience. It also feels gross to seek out a partner with a penis just to diversify my fantasy life, especially given the fetishization trans women already face. How can I stop fantasizing about someone who I hated having sex with? Is it even possible to separate the person from the parts?

— Parts or People?

Dear Parts or People,

Rich: There’s a lot going on here.

Stoya: Yeah.

Rich: So the broadest, and I think the most important thing, in this question is involving changing fantasies, which we have talked about. And we’ve talked about changing fantasies that are unwanted, and the problem is that that’s really difficult as well. I’ve talked to Justin Lehmiller about this. He wrote Tell Me What You Want, a book about sexual fantasies, based on a very wide-reaching survey that he did.

I really think it’s like anything dealing with sexuality and what feels innate—consciously changing that is just going to be very, very difficult. I think it’s in the same kind of spectrum that conversion therapy is on—it just doesn’t work. That said, many of us do evolve as sexual beings over the course of our lives, and I think what contributes so much to that is exposure and open-mindedness, and willingness to explore. So the idea would be to open one’s repertoire to give other fantasies and interests the opportunity to take over. It’s just exposing yourself to that.

Stoya: They say that they’re not interested in casual hookups or new partners, so I think it may be about finding new fantasies.

Rich: Yeah, maybe through porn.

Stoya: Porn can absolutely work for that, or websites like OnlyFans. I’m thinking of one performer who goes by Ruckus, who made a video for Zero Spaces for me. Ruckus is a total sweetheart, has a great-looking dick, makes beautiful videos. But there are so many different creators on fansites where you can also get a little bit of a sense of who the person is, which can help to connect to them and eroticize them. I’m also thinking of Shine Louise Houston’s Heavenly Spire—it’s a gay porn series, 1970s cinema-style, and a queer take on all sorts of masculine desires.

Rich: That sounds cool.

Stoya: Yeah, so there’s some stuff out there, or maybe they don’t even need to get that complicated. Maybe they just need to go to a tube site and click around and find something they like.

But I think there are other images that they could focus on when their thoughts turn to this guy. So, I’m a physical person, and I didn’t get meditation for a long time, but one day, my therapist was like, “OK, let’s try a different kind of meditation.” So she stated describing unwanted thoughts, and “letting them fall like leaves from a tree into a stream and be carried away.”

Later, I’m talking to my boyfriend and bitching about the therapist about the leaf falling into the stream and coming back and he’s like, “Yeah. And you let it go again and you let it go again, and you let it go over and over and over. And then finally, you’ve practiced letting it go. So then you can pretty easily let things go in the moment.” I finally understood it. It took several years and I’m still not great at it, but it eventually made sense.

So, there isn’t a quick fix for changing the way that your brain works, for changing where it immediately goes, right? It takes a lot of effort. It can be very frustrating. The real work is continuing to do it over and over and over. So if our writer is jerking off to beautiful penis porn, and then all of a sudden horrible ex dude pops up in their head, that’s part of it. Just let it go.

Rich: As much as it can be difficult to consciously alter your sexuality, what you say is completely right. I’m a big believer in meditation and I’m consistently impressing myself with what I’m able to do with my mind. It feels like a growing process. It’s really hard to see the forest from the trees when you’re using the same eyes for both, but the more you practice, the more you’re able to pick things out and understand the layer of thought that is above all of those other thoughts, through which you can then get in there and do some work.

To address a few of the other points that she brings up: I think it’s very wise to tread lightly, to err on the side of caution, especially when it comes to trans bodies. If more people were more respectful of them, we would live in a kinder, gentler world. That said, if you want a penis and a trans person is willing to furnish you with that penis through a mutual exchange of pleasure, I don’t see anything wrong with that. I don’t see anything wrong with wanting a specific part and getting it. That is not an issue for me.

Stoya: I do want to mention trans women who have penises—those penises, in my experience, do not tend to behave the way that a cis male penis does. So, we know that in the womb, sex differentiation happens on one set of parts, and these parts that can become a penis or a clitoris. So you’ve got cis dude penis all the way over here and the more feminine a person is, the more the penis seems to act more like a clitoris and, crucially, may not get erect. So if you’re hoping to find a trans woman to plow you with her rock hard girl cock, that might not be in the cards, and it might be a very frustrating and emotionally damaging experience for everyone. So yes, tread carefully.

Rich: Definitely. As to the question: Is it even possible to separate the person from the parts? Absolutely. It reminds me of Amia Srinivasan and her book The Right to Sex. There are things here and there that I disagree with in it, but I think a lot of it is great and it’s nonetheless, wonderfully thought-provoking. But she asks at one point, “Is anyone innately attracted to penises or vaginas?” And the answer is yes, the answer is always yes. And I think the existence of glory holes proves that point exactly, that it can really be just about the dick. And maybe that is another area of porn to look into because it would completely disembody the dick from the man. That might be the solution.

Stoya: Useful objectification, I love it. Reduce that person whom you had a bad relationship with to nothing more than the part that was good about them for you, which is their dick. And then go look for floating disembodied dicks, that also might be great.

Rich: Yeah. And look, there’s a lot of talk about the hazards of doing so, but I think it could work in less fraught spaces, amongst less fraught populations, like gay men who don’t live under the threat of rape to the extent that women do. I think that people are able to play in those spaces a little bit more. So it certainly is possible.

Stoya: Can we riff a little about objectification?

Rich: Yeah, totally.

Stoya: Regardless of whether people recognize me from my former job or not, I’m just one of those women who walks down the street and men are like, “Your eyes, I couldn’t control myself. I just had to follow you down the street to try to get your phone number.”

I’ve been reading Camille Paglia’s Sexual Personae. And I just did an interview with Christine Emba, who wrote the book Rethinking Sex that’s about a need to move past binary yes-no consent and develop a real sexual ethic. There’s also Nancy Bowers’ How To Do Things With Pornography, where she prints Martha Nussbaum’s notions of objectification and talks a little bit about how objectification, when it’s consensual, can be good.

So I’m on this whole personal questioning journey, where I’m like, yeah, I was objectified professionally. I objectified myself professionally. I also don’t enjoy when I’m walking down the street and someone objectifies me, not because of that contained incident, but because of the concern of what that objectification could lead to, which can be a bad, scary, traumatic thing.

Rich: Of course.

Stoya: But all that said, being completely railed while I am face down on the bed and can barely suck air through the mattress is really hot when it’s with someone that you’re not afraid is going to hurt you. So objectification, also not necessarily bad. Right?

Rich: I think that many things are true at once, and that you can both honor and celebrate someone’s humanity, broadly speaking, while objectifying them and being objectified in the moment. I don’t think it works as a one-way street. I think it has to be two-way objectification. I think our brains work in a way that makes objectification just a natural process. What is it to find somebody hot? Sapiosexuals aside, isn’t it to look at what they have to offer and from there, derive certain impressions and inferences, and then that all mixes up in this erotic cocktail? I don’t think it’s an excuse to treat somebody like shit, unless they’re asking for that specifically, but I think that you can do everything at once really.

The image of sex without any sense of objectification is like…what are we doing here? Are we just here to hold each other and affirm each other and kiss lightly? I think what makes this so difficult to talk about is, at least, as far as my experience goes—and I’ve heard this said before—the ultimate in sex is to have all of this stuff, to just collapse into this goo of reality, experience this flow state that you’re in where you can’t quite separate things and time moves differently and you’re conscious, but not.

Stoya: Yeah.

Rich: And so I think it only makes sense for all this stuff to blend. And I think objectification certainly has its place, as long as it’s agreed upon and reinforced with respect. You certainly don’t want to objectify someone for something that they’re ultra-sensitive about, something that would actually take them out of that flow state. If somebody’s very sensitive about being objectified for their race or whatever, you’re going to kick them right out of it, and then the sex isn’t fun for them. I think it’s about really striking that balance between objectification and acknowledgement of somebody’s humanity.

Stoya: I’m glad we had this riff.

Rich: Me too. There’s always a good time to do it because I think the conversation, at least as it plays out on Twitter, becomes totally flattened. It becomes like, you can’t feel that way that you feel, and it becomes this kind of bastardization of the way that sex actually operates for people. And I’m not saying that just because it happens, it’s right, but I am saying that it happens a lot and it’s part of the process.

Stoya: I feel like there are maybe actually two–a binary!—categories of people here: Those that see sex as an incredible metaphysical, even spiritual experience, and those that treat it like McDonald’s. And when we’re dealing with people who are walking around treating sex as McDonald’s, like great, use a condom, ask for consent, come back when you want to think and feel more deeply about this, if that ever happens for you. And then the other kind of people, it’s like, yeah, let’s get sloppy and messy and weird together. And we might go a little too far, but then we’ll stop and talk about it or talk about it tomorrow and be like, what happened there?

Rich: Yeah.

Stoya: There’s this beautiful thing that you can grow into and learn how to access, that is gorgeous and one of the most incredible things about life to experience. But only yes means yes, and any kind of no means no.

Rich: I have long been what would be deemed “promiscuous,” but to me, that actually hasn’t calloused me or hardened me at all. It’s, in fact, made me appreciate the times where the humanity does shine through. And now it’s about the connectedness—even if it’s just a fleeting kind of connectedness. It doesn’t mean we have to be partners or have something on an ongoing basis.

It’s similar to the difference between having a bunch of small talk, and a really deep conversation. And you might be talking to somebody at a party and you might not ever see that person again, you might not exchange numbers, but you had that deep conversation. And to me, that is just a much better use of my time than talking about the weather for 20 minutes.

And so I feel like there’s that balance to strike as well. You can absolutely be aware of somebody’s humanity while having a completely casual fleeting experience. It’s not all or nothing. And again, it’s the complicated nature of what happens to our minds during sex that makes it virtually impossible to talk about in a completely accurate way, when it’s not happening. Unpacking those complications is what I’m always striving for with this column. I think the best we can do is like get right up against the complexity of it.

Stoya: It’s Plato’s dildo against the cave wall. Our writer’s ex is that shadow, and they can build in their minds their platonic ideal phallus.

—Rich Juzwiak and Jessica Stoya

From: I Once Had a Traumatizing Relationship. It Still Haunts Me in an Unexpected Way. (June 16th, 2022).

Dear How to Do It,

I’m a bi woman in my mid-30s and I feel like I’m living a stereotype in a way that makes me really uncomfortable and unhappy, and I’m not sure what to do.

I was previously in a serious long-term relationship with a man, and while it was great in many ways and I enjoyed our frequent and enthusiastic sex life, I missed having sex and closeness with women. Fast forward to the present, I’m in a serious relationship with a wonderful woman—and I miss sex with men.

I’ve never been very good at casual sex, and often found it emotionally uncomfortable, so I’m not sure that opening up my current relationship would solve this problem for me. In addition, I know from direct conversation that my girlfriend is uninterested in casual sex with others and feels most secure in a monogamous arrangement, so it would likely not be appealing to her. How do I learn to be satisfied with what I have (which is wonderful) and stop feeling so ashamed of the internalized biphobia I’ve somehow accumulated around this?

—Why Not Both

Dear Why Not Both,

A relationship with a second person of a gender different from your primary partner can be significant, committed, and long-term. I think it’s worth asking your partner what monogamy means to her, why that’s her preference, and how strong of a preference she has. It might be the case that she’s open to opening up under certain conditions, and that those conditions are functional for you and the men you might have sex with. Start with getting a better understanding of how she feels, and decide from there whether to broach the subject further.

You’re right that the inability to “pick a gender” is an accusation leveled at bisexual people, and inhabiting the stereotype is pretty uncomfortable. Know that many of us occasionally find ourselves checking off all the caricature boxes, and continue on to live whole lives that go off script. You aren’t setting bisexuality back by matching the cartoon in this moment. Nor are you doomed to embody all of the fears that society has about bisexual people.

No matter what, being human is uncomfortable sometimes. We long. We yearn. You can purposefully turn your thoughts back to what you do have when you find your longing problematic–—make a list in your phone, where it can easily add to it, or meditate, or whatever else works to refocus yourself somewhere positive. Take some deep breaths. If you don’t already have friends who are also bisexual, consider trying to make some. And if you want to really dig in, an LGBT-inclusive therapist can be a great ally. Good luck.

—J.S.

From: My Friend Is Dating Again. She Clearly Never Learned the First Rule of Sleeping With Men. (January 25th, 2022).

Dear How to Do It,

A while back, I was hooking up with this girl. She had some pretty extreme BDSM fantasies, and in general I was happy to play with her in that fashion. But she started getting into a fantasy where she played at being “raped” at knifepoint. I only tried it once. It was awful. Care always needs to be taken with BDSM, but when you have a bare Yawara involved, making sure I didn’t cut her in half occupied the overwhelming majority of my attention, which just made the whole experience an unpleasant task to get through. For me, anyway. She loved it. We argued about that, and wound up stop seeing each other sexually, although we still keep in contact as friends.

Well, I recently found out she’s in the hospital—for a knife wound on her throat. Two guesses as to how she got it. She said she doesn’t appear to have any permanent tracheal damage, which is good, but I really think she’s slipped off the edge into wanting a sort of sex that could actually and immediately kill her. I’m not much more than a casual acquaintance these days, and I’m wondering what I could be doing to warn her about the extreme risks of her lifestyle.

—Knives Out

Dear Knives Out,

Having just landed in the hospital with a sex wound, I suspect she’s quite aware of how risky her enactments of her desires are. And giving her a lecture is likely to drive her away. I’d check in on her general mental state. How’s she feeling about life? How are her social relationships? How is she handling this massive pandemic we’re all still navigating through? Is there any way you can support her self-care skills? Basically, how can you meet her where she is and help her feel good enough about life that it becomes more important than this one, deeply dangerous, sexual practice? There are probably limits to what you can do here, but starting there might help.

—J.S.

From: My New Boyfriend’s Penis Had a Big Surprise for Me. Please Advise. (December 8th, 2021).

More Sex Advice From Slate

One of my closest friends (both 40, straight ladies) got divorced two years ago. She slept around a bit after, and frankly, good for her. The problem is, she’s started looking for relationships with guys, but she sleeps with them on the first date. I’ve been married for a decade so I’m definitely out of the field, but guys … don’t usually take a woman seriously after sleeping with her this early, right? I don’t know how to characterize this without sounding like I’m slut-shaming. I don’t care if she wants to sleep with a meh guy because he’s kinda hot and she’s bored. But when she flirts for weeks with a guy who is close to her kids, and they sleep together on the first date, and he immediately backs off, she’s devastated. What can I say here? I feel like a character in a ’90s sitcom telling her the rules say not before the third date!

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