How to Do It

“I Hope This Doesn’t Make Me a Terrible Person”

Can I ask trans women I’m dating about their genitals?

A man whispering to a woman with a neon female symbol between them.
Photo illustration by Slate. Photos by Sigrid Olsson/PhotoAlto Agency RF Collections via Getty Images Plus and Ayo Akinsete/EyeEm via Getty Images Plus.

How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to Nothing’s too small (or big).

Every Thursday night, the crew responds to a bonus question in chat form.

Dear How to Do It,

I am recently reentering the dating pool. My last time in it was during a time and in a part of the country where I never encountered trans people. I’m on some dating sites now, and on some hookup sites, and there are some trans women I find myself interested in and attracted to.


That they’re trans isn’t (mostly) the issue for me. I really don’t want to be insensitive or indelicate toward them, but I have a hard line about what I’m into and what I’m not. I can be attracted to any woman who presents as such, in the bedroom. I tried one encounter with a woman who identified as a woman but was very much … can I say, pre-op? I’m really not interested in playing with a penis. For this one individual, we worked through the misunderstanding, had a good laugh, and parted company amicably.


In the future, though, I’d like to find an appropriate way to ask if someone who says she is a trans woman (I usually see “ts” somewhere in the online profile) is pre-op or post-op. I hope this doesn’t make me a terrible person.


Maybe there’s something about the vocabulary of online dating that I just don’t understand, or maybe I just need a catch-up course. If you could help me understand how to approach these women in a way that’s respectful, while also getting the information I’d like, I would appreciate it.

—Just Asking Questions

Stoya: To start, I reached out to a trans colleague who had some great things to say about what sex can be. Her name is Chelsea Poe, and she’s an adult performer.

“I think being specifically a trans woman who is pre op and doesn’t have her sexuality revolve around her cock, I can really speak to what cis people assume how trans bodies work,” she wrote to me. “Just because a woman has a cock doesn’t mean that she is going to use it in the same way a cis male would use the same body part.” She said that in her own life, she’s dating a “stone top lesbian,” and she would never dream of wanting her partner to fellate or bottom for her.


“There’s also some trans women, as there are cis women, who love to peg their male partners, and that’s OK too,” she added. “I think more than anything being forward [with] what you’re looking for sexually and realizing what genitalia someone has doesn’t define how they have sex. If you’re into a girl, be into her, and if you’re both into each other, I’m sure you’ll find some way to come.”

Rich: Many good points made there, particularly the last one. The writer says that he doesn’t want to play with a penis. But he doesn’t have to, even if one is present.

Stoya: Exactly. Sex can be so very many activities. Nobody’s penis has to be involved for everyone to have a great time.


Rich: Even if the presence of another penis is a hard boundary for the writer, I think the general consensus is that asking a trans person about their parts is rude. The best he can do is wait for them to tell him. Some people are upfront about what’s going on down there in hookup scenarios. While that may cause immediate rejection, it can also mitigate risk so that the person they’re hooking up with doesn’t accuse them of trickery, or even worse, lash out in a fit of trans panic.


Stoya: Asking people about their genitals is rude, period.

Rich: But you know, on the other side, there is a lot of talk about genitals on hookup apps, at least among gay men. People ask you how big your dick is, and they want to see pictures. Sometimes they do this instead of saying “hello.” From the writer’s description, he might well be on Grindr, where those kind of conversations take place—cis straight guys pick up trans women on there all the time.


Stoya: Ooooh, we’re having another perspective difference!

Rich: Yeah, I mean, the forum of the hookup app is sort of rude by definition. It’s a lot of “Whadda ya got? NOPE!!!”

Stoya: This sounds really brusque.

Rich: It can be very brusque! App culture leaves some people shellshocked, really questioning why they’re putting themselves through it. Putting whether people should be interacting in such a way aside, from a purely practical perspective, I think our writer will find that inquiring about the contents of prospective sex partners’ underwear will turn a lot of people off. He’d be doing it to filter certain people out, but I think he’d more often be filtering himself out for asking the question in the first place, especially by trans women so used to having their bodies scrutinized. I’m less hung up on fetishization and objectification as practices in a casual setting—one-time, virtually anonymous hookups often exist wholly in the realm of the superficial. (What else is there with someone you don’t know and may likely never know?) Fetishization is de rigueur. But that mindset could understandably be received differently by a population whose humanity has been historically, and continues to be, denied to them.


Stoya: I imagine being asked over and over again about bottom surgery, in myriad clumsy ways, would be wearing.

Rich: Oh yes. From this Daily Beast piece about online dating while trans: “It does get kind of awkward. People don’t know what to say or it turns into this Q&A about my identity that I don’t want to have—because people ask invasive questions and I’m like, ‘I just met you! I don’t want to tell you about my genitals. At least wait until the second or third date.’ ” I suspect if these questions were benign, they’d be regarded differently, but so often the answer yields rejection.

Stoya: I experience a somewhat less fraught version of this because of my porn career. I end up having to defend its existence.


Rich: I’m sure people approach you with all kinds of assumptions too.

Stoya: Mostly what sucks is wanting to be seen as an individual and having that not happen. Followed closely by the super misguided assumptions.

Rich: It’s terrible. When this kind of thing is happening on apps, some of the blame must go to the medium, which treats sex and dating like Seamless. It’s very me-centered. “I want this. Are you this? No, well, you aren’t useful to me. Ordering elsewhere.”


Stoya: I was wondering if our writer approaches dates as a sex hunt.

Rich: It seems like he might.

Stoya: He might want to consider giving dates as a way to meet people a try.


Rich: Yes. I do think it’s OK to hook up for sport, which some apps facilitate more than others, but it also imparts some not-great habits for interacting with people. But this is the cruising conundrum. I recently answered a similar question and talked to my friend Riley about whether he thinks someone who says they aren’t into trans guys is transphobic. (Riley is trans and gay.) He said not necessarily, but so much of the rejection he faces is coupled with blatant transphobia, so there often isn’t even another way to read it.

Stoya: A friend of mine mentioned this—if the writer is this hung up on genitals, is there underlying transphobia? Or homophobia in his line about not wanting to play with dick?


Rich: It’s really, I think, a crucial question. But the answer, somewhat unfortunately, is open. Desire is so complicated. Is it possible for someone who isn’t bigoted in any way to simply not want a penis that isn’t his in his bedroom? I feel like yes, that is possible. People are very specific in their desires and so infrequently can specify what the origin of those desires is that the best we can do is trust them. We’re not talking about logic here.


Stoya: What are your feelings on vulvas?

Rich: I think they’re great! When I watch straight porn, I’m often so impressed with how well they work. It’s all just so convenient compared to anal stuff. I’m not averse to them whatsoever, and it really irritates me when gay guys are like “ew.” Grow up.


Stoya: I’m having difficulty putting myself in to the shoes of a person who is so off put by genital configuration.

Rich: Look, I’m way more into dick. Maybe I need to work on that, but it feels OK to like what I like. I don’t fantasize about vulvas; I do dicks. It’s plausible that someone has a type formed by a bunch of factors that are specific and don’t make him a bad person. But it’s also not just possible but observable and prevalent to have “preferences” that dog-whistle bigotry. I think these things require a lot of self-interrogation.

Stoya: I’m curious about his feelings around disclosure. Like, what he’s touchy about sharing, or feels vulnerable about.


Rich: Good question. It’s somewhat surprising that the last time he was dating, trans people were less visible—so let’s say, at least 10 years ago?—and he seems to be progressive in his attitudes about dating trans people but for the genital hang-up. He’s, like, almost there? He gets it … just about. Is the phantom penis symbolic?


Stoya: Yes. He’s looking for a safe way to bring up the thing he should probably not bring up.

Rich: Right. And actually, if he talked to more trans people, he probably wouldn’t be asking that question to us. He wouldn’t need to, and he’d know the prevailing attitude about asking trans people about their parts.


Stoya: To be clear, everyone has a right to their preferences and—if they have them—rigid desires.

Rich: No one is under any obligation to have sex with anyone.

Stoya: But yes, I think if he went on dates or coffee catch-ups with trans people and listened to them as they opened up, he’d have a lot of room to grow.

Rich: It seems like the right move here. It’s unwise to just to jump into sex not tethered to humanity in this particular situation.

Stoya: I want to underscore how vulnerable this population can be, and just how much awful harassment many trans women deal with regularly.

Rich: It costs nothing to be sensitive to that, and it would also facilitate not just sex but good sex.

More How to Do It

I’m a 27-year-old straight woman. I recently dated a man for several months who was odd about sex—he frequently mentioned that he had a small penis (which he did) and that oral sex was what made him a good lover. We eventually broke up. I have moved on and am dating a lovely man, but yesterday my ex sent me an email saying that he was bottoming for men he met online the whole time we were dating. He said he felt he needed me to know and wanted me to accept him.