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 a 52-year-old woman with three adult children. During parenting, my ex-husband and I were open to answering all questions about sex honestly and age-appropriately. Sex was neither demonized or put on a pedestal. When the kids were teens, we discussed the very real health and economic reasons to consider delaying sex, and strongly preached the “two contraceptive methods” mantra while always keeping a box of condoms in the guest bathroom, replaced as needed with no questions asked.
I recently learned that my 22-year-old daughter has been engaging in sex work since she was about 20. She went to cosmetology school and has always worked in that field for low wages at a franchise low-cost haircut place. She is also a bit of a political firebrand and talks about “late-stage capitalism” and needing to make more money so that she will be able to survive future “resource conflicts.” I am a progressive with a tendency to prepare for an uncertain future, so some of her concern for the future comes from what she saw growing up.
Sex work has been her way to earn extra money to save for her future. She told me she has been assaulted twice while working but blamed herself for “not clarifying consent” or saying “I think he just didn’t understand consent.” (I told her to stop giving older wealthy men the benefit of the doubt on this point.) She now has a “sugar daddy” who is paying her more than $1,000 a week to provide companionship and occasional sexual services. I am horrified at how she minimizes her risk of assault and the trauma, not to mention the legal risks and the ability of wealthy men to crush her socially, physically, and or financially if she says “no” to the wrong person. Do you know of any resources, hot lines, or groups I could direct her toward for support and perhaps even dissuasion of this path that would not be judgmental regarding her choice of work and her left-of-center politics? I am terrified for my daughter’s safety.
I agree with you that giving older wealthy men the benefit of doubt when we’re talking about crossing boundaries of vulnerable people makes no sense. I’m not sure if this next part will put your mind at ease or stress you out further: Many people with no connection to sex work are assaulted. Many women with no connection to sex work are sexually assaulted. There are a few factors that make sex work more dangerous—the number of people we interact with, the stigma against sex work making us more of a target to predators, and that same stigma making it more difficult to reach out for help or justice afterward—but your daughter’s attitude toward this is worrisome no matter her job.
The most important thing is not to alienate your daughter. That may mean biting your tongue when she talks about the riskier aspects of her second job. But you’ll keep the lines of communication open, and she’ll be more likely to come to you if she gets into major trouble. Don’t let the stigma get in the way of you being a safe space to turn to.
Given your and your daughter’s lefty leanings, you might ask her directly if she’s in contact with any of the sex worker support groups in her area. If she’s a person of color, the BIPOC Collective is a nationwide organization she might join. If she were creating content, the Adult Performer Advocacy Committee would be a good place for her. If she needs to talk to someone who gets it, Pineapple Support might be a resource. There may be a local chapter of the Sex Workers Outreach Project. If none of these apply, here’s hoping there’s another local group she can get—or already is—involved with.
While there certainly are groups that attempt to get sex workers out of that line of business, they’re typically run by certain types of Christian and right-wing outfits with agendas, frequently in conjunction with a church. Not to mention the fact that dissuasion isn’t likely. She’s an adult, she’s made her choices, and she feels that this is what’s right for her. The best thing you can do is accept her as she is, love her, and be there when she needs to talk.
Dear How to Do It,
I (a woman) recently started dating someone new (a man), and it’s been amazing. We connected very hard and very fast on so many levels—and it’s been the best sex of my life. We really click, have a ton of fun, and I feel adventurous, safe, and loving with him.
I typically think of myself as pretty vanilla—the kinkiest I have gotten with past partners is asking for hair pulling and light choking—and I am also overall less experienced than he is, but it’s been really fun to explore new things with him (toys, positions, etc). Early on, he started talking about wanting to bottom with me. I thought the idea was very hot, but I’d never done anything like that, so we put it off for a while as I became more comfortable. One night, after he went down on me from behind, he asked me to return the favor, so I did—and I hated it. It tasted weird and I just didn’t like the sensation. Then, we revisited the pegging conversation, and I used a strap-on for the first time—and hated that, too. I thought it would feel really hot to have a dick and be dominant in that way, but instead I was unwieldy, clumsy, and afraid of hurting him the whole time. Then, when I pulled out and there was, uh, santorum on the end of the strap-on, I nearly gagged.
I don’t want to yuck anyone’s yum, and I REALLY don’t want him to feel any shame or embarrassment around this particular desire. I think it’s really exciting that he trusts me with this turn-on, because I know straight men get a lot of horrible messaging around ass play and bottoming. But … I also really don’t want to do these particular activities again. Is there any way to have that conversation in a loving and non-shaming way? Or is it something I should just get over and do because I love my partner? Or is there some middle ground where I can get better and more comfortable with these types of activities? I have never felt toward anyone the way I do toward this man, and I don’t want to lose him because I’m squeamish.
—Pass on Ass
Dear Ass Pass,
You have all the options.
You can have a conversation with your partner about how you’re happy to have tried his turn-on, but it isn’t for you. You might want to leave out the nearly gagging part, but not liking the taste of butthole is reasonable and fair to state. You get to have boundaries as much as he gets to have desires, and your boundaries may exclude anal play on him: “Thank you for letting me in on what you like. I’m so happy we tried analingus and strap-on sex. I’m pretty sure I don’t want to do it again, though.” Or, “I want to spend some time getting comfortable with the strap-on before we try this again.”
I’m averse to should, but I do think you can work around some of this. Dental dams are one possibility—he gets all the sensation of having his ass eaten, and you don’t actually touch your tongue to his ass—and there are some things you can do to get more comfortable with a strap-on. One is making sure you have the proper equipment. How’s your harness? I’m partial to Tomboi’s briefs, but anything that really keeps the base of the dong tight against your pubic bone will do. And the dong—is it too long? Shorter gives you more control, and most of the fun parts inside the anus of your guy are only a couple of inches in.
And lastly, if you do choose to try to do this again, you can always ask him to practice more thorough (but careful!) prep. In general, though, if you’re going to have butt sex, you may need to “just” get over your aversion to trace amounts of feces on your prosthetic dick. Exposure works wonders. No matter how comfortable you get, you’ll still want to exercise proper hygiene afterward.
Dear How to Do It,
I was listening to one of your latest podcast episodes and I was very struck by something Stoya said about disclosing to a partner the fact that she’s not really into dating. I’m a 29-year-old woman who recently ended a relationship of eight years. I’ve always loved sex, but dating makes me actively uncomfortable. I find that when out on a date, my typical confidence is replaced by either irrational anxiety over the performance of “being on a date” or sheer boredom thinking about the work I could be doing or the sex we could be having. Stoya, when did you accept this about yourself, and do you think there’s a way to work it into healthy, positive relationships? I worry sometimes that I feel this way because I’m more comfortable keeping people at a distance. Part of me feels like I should exposure-therapy myself and go on a date every day for a month, but honestly that sounds so terribly boring.
This is true. I once told a friend who’d admitted a crush that while they’re a pretty romantic person, I’m like an asexual but for romance. Turns out there’s a whole word some people use for that: aromantic. That’d also be the time I accepted this about myself, and was probably in 2016.
I’m happy to hang out with people I have sex with. And once I understood dates as a show of regard and an opportunity to get to know each other, I could appreciate them as useful. When you think about it, spending 90 to 120 minutes asking each other questions saves you finding out you’ve just boned a bozo once you get to the post-coital pillow talk. There’s an efficiency there.
I’m not sure exposure therapy is what you need at this stage, but I do think some time with a therapist might help you sort out how much of this is anxiety and how much is lack of interest in romance. And having a safe space to talk about these things is beneficial regardless. If therapy isn’t an option, you can ask yourself questions and write without stopping to think for at least 30 minutes: What does intimacy mean to me? Do I want intimacy? What do I dislike about dates? What do I want out of a relationship? As you go, other questions will likely occur to you. Write them down and address them next time. As for keeping people at a distance, are you that way with friends or only lovers? That’s another question worth thinking about.
Once you’ve got a better idea of what you want, be upfront and honest with people about it. For me, that means letting people know what my time constraints are and warning them that I really don’t want to be the recipient of flowers and will never remember to send them flowers no matter how much I want to avoid disappointing them. I’m sure you’ll find your own specifics. Good luck.
Dear How to Do It,
All of my friends are very sex positive and some of them (women) have had many sex partners. I don’t have any objections or moral judgments to it, but I’m just not into having a lot of partners. One of these friends recently introduced me to a guy, “Sam.” Sam is nice, sweet, hilarious, and really attractive. We seemed to hit it off and he asked me out. On our first date, I found out he is even more sexually open than my friends. He’s gone to a couple of orgies and had probably as many partners as all my friends combined. This really turned me off for one big reason: STDs. As a woman, I’m worried about getting HPV because there is no test for men, but a part of me is also worried about getting something like antibiotic resistant gonorrhea or, frankly, some STD that we just don’t know about. I know that last part is a little unrealistic, but my concerns about HPV aren’t. Plus, I just have issues trusting someone like him would be honest if he did actually test positive. I got the feel from our conversation that he hasn’t been tested in a while because he is concerned he might have an STD. Because of these reasons, I declined a second interview.
My friends were shocked because he seemed like my perfect match. I told them I wasn’t comfortable with his sexual kinks. One friend was suspicious and after a while, I blurted out everything I’ve written here. Now, half of my friends have taken offense to what I said and think I’m judging them morally. I’m not. I honestly don’t care how many STDs they get. My preferences for my partner’s sex history is simply a practical one: I don’t want to get an STD. I know that it is impossible to 100 percent protect myself against STDs, but I just don’t want to take huge risks in that area. Do you have any thoughts on what I can tell my friends?
Dear Germ Resistant,
According to CDC data, if you’ve had sex with more than three people, it’s stastically likely you’ve been exposed to HPV. Every time you have sex with a new American adult, there’s a roughly one-third chance that they’re carrying HPV. Condoms help somewhat, but are nowhere near as effective at preventing HPV transmission as they are at preventing HIV transmission. Since you’re super concerned, I think you should know how common HPV is. Regardless of how old you are, it’s worth asking your doctor about an HPV vaccine—or, if you had the original one, a revaccination with the newer type that protects against nine strains. (While there is no HPV test I know of for penises, there actually is an anal swab that can be done on men to assess whether they have HPV in their anus. However, the CDC probably wouldn’t recommend it in this case for several reasons.)
Your fear of antibiotic-resistant gonorrhea is reasonable. It’s a real thing that happens and can be really bad. Condoms (including for oral) can drastically reduce your chances of acquiring it, but fear is fear.
Your friends may be reacting to sentiments like “I just have issues trusting someone like him would be honest if he did actually test positive,” since this seems to imply that people with many sexual partners are less honest. Your best bet is to apologize for the offense you’ve caused and ask your friends to give you specific feedback on what offended them. From there, you can decide how to articulate your issues around sex with people who’ve had many partners moving forward. You might feel no desire to change your delivery, and that’s fine, but it would be better to understand what caused your friends to get upset and make a conscious decision. Regardless, don’t let their judgment of your perceived judgment push you into sexual interactions that you aren’t comfortable with.
More How to Do It
I have been reading your column for a while, and because of that, I have gradually come to the conclusion I never want to have sex with a feminist, for the following reasons.