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’m a straight woman in her mid-30s who recently reentered the dating scene after leaving a 12-year marriage that I (obviously) entered into quite young. I took some time off from sex and dating after my divorce before deciding I wanted to try to get back into the swing of things and just have some fun. My question has to do with the fact that at some point during the long period while I was “off the market,” I seem to have missed the thing where butt play and anal have become an expected part of heterosexual hookups.
With three separate guys—none of whom I met on apps, where I now understand some of this stuff gets negotiated in advance—one flipped me over to eat and finger my ass and busted out a plug, at which point I shut that down. One kept asking whether I wanted anal and sulked and finished quickly when I said no. And the third “accidentally” rammed his dick ALL the way up my ass—he did apologize, but I’ve never had that happen before, and have my doubts about how “accidental” it was.
Honestly, I kind of like being rimmed, but it’s not something I’m comfortable with if I don’t know my partner well. And while I can tolerate anal penetration for a time, I’ve never liked it—the most I’ve ever gotten out of it sexually is finding my partner’s excitement and pleasure hot. I hate the amount of prep it takes for me to feel clean, and at best, if it’s not actively painful, it’s just … really uncomfortable. For some reason anal also tends to leave me feeling vaguely extra objectified or bad about myself. I’m not sure why. Maybe just the vibe that my mouth and pussy aren’t “good enough.”
I’m definitely not trying to shame anybody for what they’re into in bed. And I recognize that I might just have had a consecutive string of bad luck on this front. But I admit to a high degree of, I guess, culture shock here—and it’s something my few single girlfriends have encountered as well, although not as consistently as I have. I’m literally three for three. So I guess my questions are: How and when did straight dudes start expecting this during an initial, casual encounter, if in fact they do? By being clear that I want to keep things casual, am I somehow signaling that I’m up for everything? And at what point can I address it tactfully going forward—before we even meet up? When it’s clear that we’re going to fuck? If and when a dude makes a move in that general direction while things are already underway?
Dating is a gantlet. Dating people with no connection to your social group is even more so. I think you’ve had a run of bad luck, and heterosexual men are generally more likely to make assumptions in bed rather than have a conversation. Not to mention the second guy’s sulking, which is real and really off-putting. As for the third guy, I share your doubt about the “accidental” nature of ramming an entire penis all the way up someone’s ass. And if it wasn’t actually accidental, it would be reasonable to deem it sexual assault.
You’ll have to sort out what your style is, and may want to use different tactics in different situations. With some men—the ones who seem particularly exuberant or impulsive—I’ll have a clear conversation during the first meeting about how I need them to ask first for any new specific act. This does not always work. One guy said he came from the kink scene, claimed that he absolutely understood and would adhere to my boundaries, and then slapped me out of nowhere early into the second date. I also tend to broach the subject of sexuality in the abstract early on—easy when you’re a semi-retired adult performer and a working sex-advice columnist—to see how well they can communicate. If a person can’t have a direct conversation about sex, it’s unlikely I’ll be having sex with them. This is also a great time to segue into discussion of likes and dislikes, and evaluate how they respond—are they pushy? Disinterested? Engaged? Sulky? Sharing their own tastes and boundaries? These are useful points of data. Some are green flags; others are red.
I have two heterosexual male partners—one fairly frequent, the other a comet—who like to lick and finger my ass. Sometimes it isn’t a good day for that, and I’ll bluntly say “nope!” at medium volume when they start to edge that way. Crucially, the “no” has to be loud enough for the other person to hear. Since “oh” and “no” can sound similar, I go with the full “nope.” They listen, and that’s why they’re invited back over and over again. My point here is that building a stable of sexual partners is a process, involving trial and some amount of error—which you’ve had a run of—but at some point you’ll find what you’re looking for. Along the way, remember you can absolutely take breaks. If your string of anal-obsessed hookups continues, it’s OK to stop dating for a bit. Because, really, it can be a gantlet.
Dear How to Do It,
I’m a 29-year-old woman who recently got a new partner, a 28-year-old man, who is into giant dildos—e.g., Mr Hankey’s. I’m excited to participate, but skeptical anything much bigger than he is will fit. Do you have any resources on safe ways to start stretching out to accommodate some large toys? We are both on board and will be patient with the process! Thanks for your advice.
—David vs. Goliath
Good on you for being up for this and accommodating of your partner’s sexual interest. Let’s talk about the general concept of safe. There is no such thing as “safe sex,” only safer, even in this context. The average circumference of a newborn baby’s head is a little over 13.5 inches. Some of Mr. Hankey’s 4XL dongs are upward of 15 inches around. Not all births involve perineal tearing, but it occurs often enough to be described as common. Sometimes objects are more easily inserted than removed. To be clear: What goes in easily might cause injury on the way out. One thing you can do to mitigate risk is choose straight or tapered toys over those with a bulge at the tip.
Before you engage in any high-risk play, you’ll want to evaluate, and possibly improve, your communication skills—with your own body and with your partner. I’m assuming that you have a vagina, and that that’s the orifice you intend to stretch. Spend some time focusing on the various parts—feel around between the folds of your labia, tighten and relax the muscles around the opening of your vagina, use your fingers (or your partner’s, or a toy) to press around the area where your cervix is, and the walls of your vaginal canal. Develop an awareness of how your genitals feel in their resting state, and what stimulation of each area feels like. Start practicing this awareness when you’re masturbating or engaged in partnered sex. You’re less likely to injure yourself when you’re aware of what you’re feeling. Once you’ve strengthened your ability to feel your body’s signals, you’re in a better place to start using large insertables on yourself. It’s also time to think about how you communicate during sex. If you say “slow down,” does your partner respond to that immediately? If you say “slowly pull out,” will he hear the important part about speed? If so, awesome. If not, sort that out before you have them drive the dong.
With wide insertables, it helps to visualize your groin opening. You might think of your genitals as a butterfly unfurling its wings, or you might familiarize yourself with an anatomy chart and use more direct imagery. Whatever you choose, think of your orifice as expanding. You’ll want to be in a position that allows you to fully relax—upright and riding the phallus can certainly be worked up to, but it probably isn’t the best for your first time out. Breathing deeply and exhaling fully helps as well. Lastly, stop and slowly disengage at the first sign of discomfort. What feels mildly annoying when you’re all worked up can be deeply painful the following day. Go slow and steady, and use lots of lube. Remember, you can always stop. Good luck.
Dear How to Do It,
I’m a straight woman in my late 20s who has only had sex with a few people. Now I’ve started carefully seeing someone new and, after confirming we were both COVID-free and not seeing anyone else for now given the pandemic, we started having sex. Mostly it’s been great. He is very kind and attractive, and is extremely generous and communicative in bed. But there’s one issue that I’m not sure how to address given my relative lack of experience: Whenever I’m having penis-in-vagina sex, I can never feel when a man orgasms, even though he is inside me. In the past, I’ve usually figured it out from other context clues—the man says something, his facial expression, he stops thrusting, etc.—but it’s often a bit of a guessing game, especially if I’m on top. It seems like men typically expect me to feel when they are having an orgasm, and because I don’t, this sometimes leaves me feeling awkward or like I’m not sure whether I’m responding appropriately. It hasn’t caused any major issues with the new guy yet, but this does make me anxious, especially because I am often thinking about this in the moment instead of just enjoying the sex. I can’t tell if I’m overthinking this or if I’m genuinely doing something wrong here. Should I be able to physically feel when a man orgasms during sex? And if so, how do I address that I can’t?
—All the Feels
Hey. You’re OK. Some penises convulse theatrically, but many don’t, and your sample size is pretty small. This might be a coincidence—a string of partners who don’t flex so vigorously when they ejaculate.
I’m curious about this “seems” thing. Have previous male partners expressed to you that they expect you to be able to feel their orgasm with your vagina? If that’s the case, they’re being unreasonable. If it isn’t the case, it’s worth evaluating where that idea came from.
You describe your new partner as communicative in bed. Verbal feedback is just as valid as physical, and physical input like facial expression is just as valid as feeling their dick spasm. Have a conversation—in the moment, or at a different time. If you go with the former, a simple “Did you come?” works. For the latter, you might express that you feel anxiety around not knowing when he’s finished, and that you’d appreciate some communication about that.
If you want to spend some time tuning further into your genitals and the sensations they experience, it’s worth reading my answer to David vs. Goliath above. Breathe all the way into your lower belly—your pelvic floor if you can—and start zeroing in on different areas of your parts. Remember to exhale, too, of course. I can’t guarantee that you’ll be able to feel every penis’s peak of pleasure, but it might help.
Dear How to Do It,
I’ve hit a stumbling block in my relationship, and I’d love to hear your advice. My boyfriend and I have a great sex life, but we are at a stalemate regarding one act: cunnilingus. He is not very confident in his oral abilities, which might be resolved with a bit of practice, but he doesn’t like doing it for me because of my pubic hair. The sensation of pubic hair in his mouth really squicks him out. We tried it a few times; he was clearly miserable, and I didn’t really enjoy it.
We’ve discussed the matter several times, and we have very different opinions about pubic hair. He shaves his regularly and believes that it is the polite thing to do when receiving oral. This opinion seems to be based primarily on his experience with his first girlfriend, who refused to go down on him unless he shaved, but now he genuinely prefers it that way for himself. I don’t mind the state of his pubic hair, however he decides to groom it. For me, body hair is a difficult topic. I’ve been shamed for my body hair ever since puberty, and I decided that I will no longer groom my body hair based on other people’s standards. I’ve explained this to my boyfriend and made it clear to him that shaving is not something I’m comfortable doing. He asked if I would consider trimming instead and promised that he’d give me tons of oral if I did, but that sounds a lot like a bribe for sex that I have so far not enjoyed very much. I don’t think that’s worth triggering my trauma about body hair.
On the flip side of things, he loves getting oral from me. He was the first person I’ve given to, and I had plenty of self-consciousness and discomfort of my own about having a penis in my mouth; I managed to get over it because I wanted to give him a good time. A part of me wishes he’d just push past his discomfort with oral like I did, but I would never ask that of him. I do think it’s unfair that only one of us gets to enjoy oral sex, so I suggested that we take it off the table unless we’re both receiving it, which upset him enough to go down on me again (it still wasn’t great). I really want to figure out a compromise that is fair to both of us. Most of his knowledge about sex is informed by previous girlfriends and porn, while mine is mostly informed by erotic fan fiction, so we could definitely benefit from your advice! I bought us dental dams and Lorals to try out, as well as the book She Comes First by Ian Kerner for us both to read. Is there any advice you can give to help us both have a good time with oral sex? Am I being unreasonable on this matter? Is he?
—Hairy’s Not Scary
Dental dams are a great solution—bravo for thinking of them and taking the step of acquisition. Hopefully that helps solve your impasse.
Your boyfriend has a belief about what is polite for oral sex, which gives me pause. Beliefs are frequently uninterrogated. Polite, particularly in the United States, has a connotation of not rocking the boat, and much like the concept of good sex or good porn is highly subjective. Different subcultures have different values. In this case, your subculture of two has two differing opinions about body hair. You might try to have a conversation with him about his belief, asking questions to help him think through whether those beliefs are what he wants to live his life according to.
Based on what you’ve written here—fair, unfair, off the table—and his response of asking you to trim when you said no to shaving, it seems like the two of you are negotiating. If that’s the way you want to approach this, great! That’s your choice. Figure out what your absolute nos are—your deal breakers—and ask him to do the same. Meet to discuss whether your wants and hard limits match up. Personally, I’m “fair”-averse in these situations, especially when we’re talking about single-subject equality: Equal treatment might feel like a nice, ethical way to move forward, but people aren’t the same. We don’t have the same boundaries, the same needs, or the same life experiences. Let’s look at open relationships, for instance: When a heterosexual couple opens up their relationship, there’s often an expectation that both people will be out having extra encounters at the same rate. The fact is, most women hold a higher value in the dating scene than most heterosexual men, and that affects their success rate. The point I’m making is that sometimes “fair” and “equal” in bed don’t really work out in practice. It may be that you could push past your discomfort with oral sex, but he can’t.
At the end of the day, you can’t make your dude enjoy pubic hair in his mouth. You don’t enjoy sexual activity that he’s clearly made miserable by. And you’d like to experience receiving oral sex. Usually I warn people that the thing they’re yearning for but haven’t yet experienced is probably built up in their minds to a level that reality can’t possibly be as good as, but in your case, I think you’ll enjoy it with a partner who actually wants to go down on you. It’s possible that he’ll come around eventually, or that you’ll become more comfortable with the idea of compromise and trimming. How long you want to wait around for that is up to you.
More How to Do It
I met a guy on a dating app in November 2019. We hit it off immediately and had a lot in common, and we were looking for something similar. We made several attempts to make plans that kept getting canceled because of busy schedules, and then COVID happened. We ended up meeting in person finally in May 2020 (masked up and safe) and continued to see each other throughout the summer and into the fall. About a week before he was supposed to start a new job out of state, he didn’t return any of my texts. We didn’t normally go more than a few days without texting, so I was worried. I knew he wasn’t on social media, but ended up searching for him on LinkedIn, and it turned out we had a shared connection. It also turns out that the name he gave me when we met (and on the dating app) wasn’t his actual name—he gave me a different first name. OK, now I was curious. So I Googled him. I’m gutted by what I discovered.