How to Do It

I Don’t Know How to Tell Men About My Sexual “Surprise”

A woman in front of a vulvic spiral.
Photo illustration by Slate. Photo by Ralf Nau/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!

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

Dear How to Do It,

I read your recent column about a guy with a micropenis and would love some advice for the other end of the spectrum: I’m a woman who had cancer 11 years ago that left me with vaginal stenosis. I’m 49 and I’ve been single for four years, so the stenosis is pretty bad (if you have regular sex, it’s often not a huge issue). If I meet someone, it would likely be a long time before we could have vaginal sex—it would motivate me to use my dilators, but it could take surgery. However, I’m a very sexual person and I am sure we would both be satisfied in other ways. So my question is: How do I convey this issue to someone I’m dating? I’m comfortable with saying it in the moment, but I’d hate to really be into someone and have them leave at that point.


—Sex With Stenosis

Rich: Before we answer, I have a question. If she’s referring to the column I think she is, I answered it and I suggested to the woman looking for men of a certain length that she behave more like men who have sex with men on apps and do all of this negotiation upfront, potentially in one’s profile. Like, it’s not uncommon to see on Grindr someone looking for “8+ inches” or to do certain acts only. Do heterosexuals ever negotiate like that (outside of the realm of kink, that is)? Is it ever socially acceptable to be upfront about your sexual interests in (vanilla-ish) spaces that connect men and women?

Stoya: She might be referring to the question I answered about micropenises a couple of weeks ago, too.


Rich: Ahhh shit. We are swimming in micropenises.

Stoya: I think we need to dig into the divide between heterosexuality and queerdom here. On one side, all things sexual are sex; on the other, only penis in vagina or anus is sex. And I really think heteronormative people would be happier if they got a little queer. You don’t need to put anything inside anywhere!

Rich: Right, I think in some ways these conversations about “WHAT I’M INTO” are easier to engage among queer people, who are used to “deviating” anyway. Once you’ve deshackled from societal expectations, you can really revel in your individuality and the ensuing freedom.

Stoya: This is a context in which I consider myself pretty queer. And yeah, we just assume we’re all going to have different boundaries and comfort zones and triggers. And talking through all of that usually functions as a kind of foreplay.


Rich: Right. Even if it isn’t by way of greeting, the pre-sex conversation about what you’re comfortable with is fairly standard, or at least it should be?

Stoya: I agree wholeheartedly.

Rich: Our writer should feel free to initiate that conversation early. You know, there are people who project a certain identity based on their proclivities. The archetypical cocksucker, for example. There are guys who just want to suck dick, so much so that it’s practically their sexual position (along the lines of how a top/bottom/vers might identify himself).


Stoya: And people regularly really lead with these things.

Rich: Right. Like, before, “Hello,” if there even is a hello.

Stoya: Like, literally.

Rich: By putting yourself out there early, you risk rejection, of course. But you also leave the opportunity for a strong connection. If I say, “I really want to suck dick,” someone responding to that is likely really going to want to get their dick sucked. And it’s way more fun sucking the dick of someone who really likes it, rather than someone who’s kind of lukewarm on blow jobs.


Stoya: And as a person who has specifics that are … divisive … getting them out of the way upfront is super efficient. Most of the time, I tell people about this column in the first half-hour or 1,000 words of conversation. And the fact of my porn career isn’t far behind. So I find being upfront efficient and useful as well.


Rich: I’d rather be judged swiftly than waste my time. And you know, not everyone, regardless of age, is going to be jumping into PIV sex immediately, and someone who goes around expecting that is setting himself up for disappointment. Our writer has very specific reasons for not having intercourse immediately, but there are many reasons for this, and some relationships take time to build to that. So I don’t think wanting to keep things oral for a period, for example, is going to come off as ridiculous or prohibitive. Not to everyone, at least.


Stoya: If it alienates them, you’re probably better off.

Rich: That’s my general philosophy in most aspects of life.

Stoya: And the earlier you state the potential flag-raiser, the less attached you are when one comes up red.

More How to Do It

For as long as I have known her, my wife has been interested in “incest” role play. While it isn’t my cup of tea exactly, I have been willing and happy to support her in her exploration of this kind of fantasy and role play. Often, she will have me dress up as her father, wear his cologne, etc., while she will wear her “high school” clothes. Recently, though, things have started to move in an uncomfortable direction for me. My wife is very close with her older brother, who is also bi, and with whom we often speak very openly about sex and sexuality. A few nights ago, and after a few drinks, my wife got to talking fairly explicitly about some of the “family” role-playing that she and I are into, and her brother—who I thought would be kinda horrified—was not only entirely supportive, but vaguely expressed interest in exploring this kink with us. When we got home, I expected my wife to make it clear that her brother ever joining us in the bedroom was entirely off the table, but instead she seemed to think it was a really good idea.