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,
Eight months ago, I started dating my now ex-teacher. I’m 26 and he’s 43. At first it wasn’t serious (for many obvious reasons, I had a hard time imagining myself getting emotionally involved with an older man who was also my teacher), while he showed much more interest in me. Things turned sour during summer when I had a brief fling with someone else and told him about it. We had a trip already organized and we decided to go anyway. After our return, I asked him if he was interested in getting more serious, and he agreed.
It’s now been three months, and since then everything in our relationship is complicated. I’m always the one initiating conversations about how I feel. I’m falling in love with him, but the relationship doesn’t feel serious at all—he never proposed to introduce me to his friends or colleagues. His parents live abroad, and they’re coming for a week next month, but he hasn’t talked about introducing me either. When I talk to him about it, he says he would be happy to, but my instinct tells me he’s uncomfortable. He and I stayed friends with a group of other students from his class, and we hide our relationship.
I had another conversation with him over the weekend and told him I wasn’t satisfied with the way things were, and that if he wasn’t ready or capable of giving me what I need—a real relationship—then I needed to know so I could move on. He said he has feelings for me, doesn’t want to stop seeing me, that he wants to make me happy, and that he doesn’t want to lose me. Is it me, or is that not a real commitment? It doesn’t really mean anything, does it? I want to respect his boundaries, but he was in a decadelong relationship that ended two years ago and left him heartbroken. Also, the teacher/student status could possibly lead him into trouble, and the age gap is probably something difficult for him to assume. But I’m hurt and tired of feeling like a mistress/someone he’s ashamed to be seen with. I know he cares for me and I’m the first person he’s seen regularly since his breakup. Are things ever going to change? What should I do now? We’ve had so many conversations about this already. We’ve been seeing each other for a while, and I wonder if the fact that he hasn’t fallen in love with me yet means it’ll never happen. I care about him a lot and really want to make things work.
Dear Still Learning,
Well, my hackles are up. He’s 17 years older, he was your teacher, and he’s keeping you separate from the rest of his life. He doesn’t initiate conversations about your feelings or the relationship, and it does sound like he’s pretty noncommittal.
Why do you want to make this work? I mean this in the most curious way possible. I want to know what’s great about him, why you’re still here when he isn’t changing his behavior, and why you’re willing to tolerate the way he treats you.
Make a list. Ask yourself if any of these qualities are unique to him. Make another list of what you think you need to feel happy and secure in a relationship. Ask yourself if he’s meeting those needs. Weigh your responses to the two lists against each other.
You have to decide what kind of treatment you’re OK with, what you’ll tolerate, and when you’ll walk away. So take a long, hard look at yourself, your relationship, and him. I think you’ll find your answer.
Dear How to Do It,
My husband and I are in our mid-40s and have been happily together for over 20 years now, including the production of two young children. Sex has ebbed and flowed over the years, and I want to work on maximizing my current “flow” stage and spice things up. When we have sex (not as frequent as I’d like), it’s very good, and he’s very attentive to “all” the needs that I have. Recently, he’s expressed interest in some butt stuff on his end (we’ve gone full anal for me for a few years with high satisfaction). I’ve done rimming and fingering, but what’s next? He wants me to “surprise him” with my “creativity.” What does that mean? Is pegging the next step? How do I do that? Please advise!
Dear Going In,
You’re going to have to talk about it.
It’s a really nice fantasy to imagine that your partner will just know what you want and do it perfectly. Especially when we’re talking about exploring a kink, and especially when we’re talking about being a bottom or recipient. As wonderful and delicious as that fantasy is, it isn’t best safer sex practices.
You might start with something like “I want to penetrate your ass” and see how he responds. You might ask him directly what he wants next, with “what kind of anal play would you like to do in the future?” You might ask him to pull porn clips or erotic story snippets that demonstrate the kind of anal he’d like to receive.
Once you know exactly what he wants—and yes, I agree that it’s probably pegging—you can start figuring out how to make it happen.
You’ll want a good strap-on that fits you well and sits sturdily just above your pubic bone. If the dong is on the pubic bone it might cause pain during penetration. If the strap-on harness doesn’t fit well, it may wobble around and be more difficult to control. I recommend Tomboi’s SpareParts line. They come in a decent size range and have a number of different models.
You might wear your harness and dong around the house to get used to it, or lie on your back and stroke your dick. Even though you don’t have nerve endings—especially because you don’t have nerve endings—you’ll want to accustom yourself to your new protrusion.
When you’re doing the penetration, grab the base of your strap-on to direct it. Especially when inserting. Remember to give your husband a reach around, or instruct him to stroke his own genitals—whatever fits the mood. Go slow, and remember that the prostate is only a couple of inches away from the anal opening. Use plenty of lube.
While you’re actually having sex, continue to communicate. Ask him how he’s feeling, whether he likes what you’re doing, if you’re going too deep or hard, and how intense he wants the sex to be.
Lastly, do a blameless postmortem once the afterglow has worn off. Talk about what worked well, what felt awkward, and what you’d each like to have more of going forward.
Dear How to Do It,
I’m a cis pansexual woman in my late 20s who grew up in a religious home with the whole “no sex before marriage” deal. As I grew up and figured myself and my sexuality out, I realized that I was fine with being sexual, but kept any kind of genital penetrative sex as something to wait for until marriage. Obviously, this would only truly apply if I married someone with a penis, but that’s my (admittedly weird) boundary. My ultimate reasons for my boundary are twofold: 1) how I have personally reflected on my religious beliefs; and 2) I’m legit so tight down there. I’ve never successfully put a tampon or menstrual cup inside myself!
I met a wonderful genderfluid person about two years ago. While dating, I explained my boundary where other sexual acts (digital and oral) were fine, but I was waiting to do any PIV penetrative sex with the person I married. They were very fine with it, and our sex life is satisfying. And, well, they just recently proposed, so marriage is in the works!
So back to my issue of being too tight. My OB-GYN told me when I was a teenager that I might have a muscle layer hanging too low? I did a Pap smear for the very first time last year, and I screamed during the process. When my fiancé and I fool around, they rarely finger me, but I’m told they can successfully get in about two-thirds of their middle finger. (They’re over 6 feet tall with long fingers, if that helps—I’m tiny and barely 5 foot.)
I know we need to do some prep work to even attempt for me to fit their 7 inches (!). But I need some hope and answers on what to do. While I’ve considered that I might have vaginismus, the fact that it’s constantly a problem makes me think it’s an anatomy issue, which I’m not sure is good news.
I should be clear that what I already do: I’m not expecting PIV sex to be somehow better or more magical. I just want it to be an option with the person I’m marrying! Do you have any advice for us? Or is this a hilariously depressing match up of bodies?
—Too Tight to Tango
Dear Too Tight to Tango,
This isn’t a sex and relationship advice columnist question. This is a qualified medical professional after a thorough physical exam and medical history interview question.
See a doctor. Specifically a gynecologist. Work the relationship angle—introduce the fact of your partner, emphasize that you intend to marry them, and ask for help in the marital bed department. If they don’t take you seriously, find another gyno. You might have to go through a few.
In the meantime, you can do some research. You can do this solo or enlist the help of your partner. Make sure the hands that will be doing the experimenting are clean and the nails have been trimmed and smoothed. Do some breathing—all the way past your belly and into your pelvic floor—and focus on your body. Ask your body how it’s feeling. Relax. When you’re ready, slide one finger in to the first knuckle. Feel around. Does anything hurt? Now to the second knuckle—again, does anything hurt? Try two fingers up to the first knuckle. Does trying to insert them hurt? Keep meticulous notes so you can show them to the doctor when you find one who wants to help you solve your problem.
Dear How to Do It,
I’m a hetero woman in my early 40s who has always been squeamish. I don’t like the idea of bodily fluids or germs. Also, the idea of a strange smell or a weird taste fills me with anxiety. Suffice it to say, I’m not into oral sex (giving or receiving). I want to get over my squeamishness, I just don’t know how. I want to be intimate with my husband in this way but cannot overcome the hurdle of my anxiety around this (not just anxiety for myself but for my partner). When I orgasm, my vagina sometimes has a strong smell (I think of BO), even when it’s clean, so that doesn’t help matters. I’m very tired of myself around this. But I’ve been married for five years—and can’t imagine how bummed my husband feels about it. WTF can I do to improve our sex life? Help!
—Over the Anxiety
Dear Over the Anxiety,
Exposure therapy! To borrow from various medical and recreational marijuana companies, start low and go slow.
The next time you have an orgasm, stay where you are and inhale deeply. Notice the smells in the room. Try to stay in that moment for as long as you can. Ask your husband what he smells and how he feels about those scents. Sit with this sensory input for as long as you can, and then go ahead and get up to shower and air the room out.
Reverse it. Smell your husband’s dick. (Now Riskay’s “Smell Yo Dick”—featuring Aviance and Real—is stuck in my head. I’ll be humming it for the next week. You might find some levity in it yourself.)
You don’t have to get too close. Just enough to smell something. Inhale, hold, and breathe out. Observe your olfactory sense. Remember, you can always back away when you need to. Get used to the smell so it doesn’t feel so weird. Work up to being mere inches away, and then within tonguing distance. Eventually, when you feel ready, give the tip a tentative lick.
Go at your own pace, and stop and/or retreat whenever you feel like you need to. The point here is to increase your distress tolerance and become accustomed to sex smells, with an eye toward eventually trying oral sex. Be gentle with yourself and take as much time as you need. Tell your husband that Stoya says to be cautious and let you lead the exposures. You’re in charge. It’s your boundary expansion. As for germs, if the two of you are monogamous, you can get that worry out of your head with a simple full-panel STI screening for both of you.
If you don’t see a change in your comfort level, or you’re feeling less comfortable, I think a trip to a psychiatrist might be worth a shot. Sometimes you need a one-on-one session with an expert to figure out what’s going on.
You can also mask the taste of penis with something like honey. Just make sure to wash any sugar-containing substances off before any PIV or PIA sex.
More How to Do It
I’m a man who’s been in a relationship with a man for about two years. We have a healthy sex life on our own, but I have a greater desire for variety, so he’s OK to let me have things on the side when I want. I usually have a few other partners a month. He does not, but we communicate about this. My trouble is that lately, I feel gross when I see other people. I think it might be because I’m falling more for my guy, which is a good thing. I worry, though, that this is rooted in feeling like monogamy would be the true “seal” of our relationship. What do you think is going on?