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,
So, my partner and I have been involved for about eight months and have been sexually active for a little under a month. The eight months were on and off, so we’re definitely still getting to know one another in many ways. The intimacy, mental stimulation, and foreplay are incredible. He’s also well-endowed, so I didn’t think anything would be an issue until I would get on top and it feels small… I mean I do pelvic exercises and I try to get into the right motion but it still seems like something is missing. In other positions or even oral it doesn’t feel that way but he likes it quite rough and I’m more of a sensual lover. It’s quite conflicting and I’d really like us both to be satisfied, some nights it’s ended with him not even ejaculating and I can’t help but think it’s because we’re just not on the same level in this area. It’s taking a huge shot at my ego as well because I’ve always held my own during sex.
—What Do I Do?
Dear What Do I Do,
I am confused about your situation. He’s well-endowed enough that you “didn’t think anything would be an issue,” but when you get on top his dick feels small and you feel like you’re missing something? Or he’s so well-endowed that once you’re on top your vagina feels small and the sex is rougher than your sensual self would prefer? I’ll answer both.
If you’re wanting more girth than he’s giving, you can use your physical awareness from those pelvic floor exercises to squeeze with your pussy, and also to squeeze with the inside of that space between your upper thighs and butt. Squeezing with your whole buttcheek, meaning including the area around your sciatic nerve on the outside of your flank, is futile in my experience but might work for you. If it’s a length issue, experiment with leaning forwards and backward. Everyone’s internal anatomy is different. For me, sitting completely upright and then tilting my pelvis forward while leaning backward—bending at the hip bones—usually gets their cock pretty close to what we call the A-spot. I’m not sure why we don’t just call it the upper sweet spot, but I do know that once I’ve got the head of their cock up in that spot, I don’t really care about length or girth or much of anything.
If the issue is that you’re less spacious than you want to be, get the idea of “holding your own” out of your head. Sex doesn’t need to be a competition or a battle. Ideally, you’re there to make each other feel good, to make yourselves feel good, and to be intimate—whether that looks like BDSM, slow thrusting, or sex acts that don’t involve penetration at all. You might enjoy yourself slowly on top—squeezing without bouncing up and down or him thrusting—and then move into another position, such as “spoon,” that allows for rougher thrusting without causing you pain.
Also—and I’m aware that this may sound deranged even to people who’ve had years of physical movement training—I’ve been able to get my body to accept more than I thought it could with some mental gymnastics. When I was in ballet, we used a laser as a metaphor. We’d say there’s a laser coming from your hip, through your knee, ankle, and foot, and then out of your big toe. The idea was to keep the leg straight and stacked on top of itself by imagining the laser and then not breaking that line. So, with that groundwork laid, think of your vagina as a cave. Remember that during arousal the cervix pulls up and the vaginal canal expands or “balloons”—imagine that ballooning. Imagine your anatomy making space for him. Breathe deeply and focus on the sensations of your body expanding as you inhale and exhale. To be clear, this does not always work for me, but when I am able to take a cock that’s a bit too big, that’s how I’ve been able to do it. The Ohnut might work better than my visualization tricks if your issue is length.
Do ask him to meet you in the middle, as you try to meet him there. If he won’t budge, he’s not the guy for you. If he will, and the two of you are too far of a stretch, there’s no shame in articulating that and separating.
Dear How to Do It,
My wife and I have been married for 21 years and have two kids age 7 and 9. We’ve only been with each other save for a one-time mutually agreed-upon incident when we were very young. My wife and I decided one night it would be hot to have sex in front of another woman while that woman masturbated while watching us. The rules and limits were obeyed and basically, we were allowed to touch her breasts but nothing else and no kissing.
That experience was…interesting in the fact that afterward, my wife mentioned she enjoyed it a little more than I did. At the time, I was insecure and worried that any further actions would cause problems so we agreed not to try again. Fast forward to now and we discovered the app Spicer and have been having fun answering sexual questions and finding our matches. This has led to a serious uptick in our sex life to pre-children levels. One thing that is interesting is she answered yes to having sex live while another couple watches and watching another couple have sex.
After what happened previously, swinging with any kind of swapping is out of the question. I told her I would like to attend a sex party to watch and maybe we fool around as well. She was hesitant about the idea. We have since role-played a full swap by surprising her with a life-like dildo and using our fleshlight. She seems turned on by the idea but also says she just wants me. I’m personally curious about what penetrative sex with another woman would be like I also have no intentions of doing anything that my wife wouldn’t approve of. I’d like to attempt same room same couple sex with no other interaction as a way of testing the waters. How do I approach her with this that I’m serious and not simply joking to be “hot”?
—Curosity Killed the Cat
Dear Curiosity Killed the Cat,
“Hey, I love you. This Spicer thing we’ve been doing has me thinking about exhibitionism and voyeurism again. Could we have a serious talk, about how we might explore some of that together a little more? It’s really important for me that we stay within your boundaries, and I’m aware that neither of us has enough experience to have a firm idea of what our boundaries are. But I’m serious, and the idea of doing this with you really turns me on.” Keep an eye on your own boundaries as well, take it slow, and I think the two of you will have a great time with whatever you end up getting up to.
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Dear How to Do It,
My fiancé (28<) and I (27F) have been together for nine years. We have a great relationship and are generally pretty communicative, and the sex is great. There are just two issues. One is that my fiancé has the same sex drive as when we were 18 and I just don’t. We work opposite shifts right now which is rough, and I’m in school on top of that. I’m exhausted. It hurts his feelings that I’m not constantly in the mood like he is every time I see him but if it were up to him all of our time would be spent doing it. We still have sex four days a week, usually more than once a day. I don’t know how to get him to understand that it’s not him, I’m just exhausted, and going at it nonstop is harder now!
The second issue is that it’s been nine years, and aside from group sex, we’ve done it all. We’ve been adventurous but I know what I like and what I don’t. He says we “never try anything new and it’s always the same” but seriously I can’t think of anything new to try! And I have to roll my eyes because you’d think from his perspective it’s missionary every night but I assure you, it’s not. We switch up positions, who’s on top, toys, and where we’re doing it. He’s not into group sex, I hate anal. Am I missing something? When you’ve gone through the Kama Sutra with someone, how do you continue to bring new things into the bedroom?
—Not 18 Anymore
Dear Not 18 Anymore,
Vanilla is a spice. Foreplay is often a lost art. Playboy once commissioned me to write an essay, which is now lost to the sands of time, about sexual exploration. Since I can’t link it, I’ll summarize myself here. Alongside the story, they featured an X and Y graph on the opposite page because my argument was that sex is not an escalator or a forward line through time. It’s a kind of geography. Wherever we are is the center of our world, where our perspective looks out from. Whatever we haven’t explored is new territory to us. So one thing you can do is make your own X and Y graph and look at what the two of you haven’t explored. My gut says maybe slowing way down and looking outside of genital engagement and orgasm might be fertile territory, but I’m guessing here.
That said, he’s bored and you’re tired. It is absolutely not your job to be the activities director on the cruise ship of his cock. If he leans into masturbation and starts finding new ideas, techniques, and sensations that are exciting for him, he’ll not only have an outlet for his sexual appetites, but he also might be able to bring fresh activities to the table himself.
You’ll know how to best pitch this from your near decade-long happy and healthy relationship. Start with how much you love him. Tell him how attracted you are to him, how much you value him, and how happy you are to be in each others’ lives. Then remind him what your schedule is. Do this concisely but clearly. Tell him what your energy level is and how you preserve the time you do have together. Mention that you’re looking forward to the day when you have less pressure on your schedule. Then suggest that he start exploring solo time in a profound way. I think you’ve got this.
Dear How to Do It,
I’m an early-40s, heterosexual woman who is not in a place in my life to be in a serious relationship for the foreseeable future (caring for a sick parent in another state and devastating breakup last year). I have a high sex drive, though, am horny basically 24/7, and miss shared orgasms and skin-to-skin contact. I want to have a friend with benefits, so I can spend time and have great sex with someone whose company I enjoy, but then not have to worry about or interact with them beyond basic caring about a friend’s well-being.
Based on what I’m seeing on the apps, there are plenty of men who would be open to such an arrangement. But, actually cultivating that seems much easier said than done. The couple of men I’ve met up with either have a lot of drama in their personal lives that they want to share (while I don’t), they’re poly and have low-to-no bandwidth because of their half-dozen other partners, or I don’t enjoy them sexually at all. I’ve tried looking for swingers groups, but the ones in my area are difficult to find or have shady reputations. I’ve even thought about hiring a sex worker, but that is not a long-term solution and I worry about the potential legal issues (i.e., it’s illegal where I live) and how to go about vetting such a person. I feel like the universe is telling me to abandon this pipe dream, but then I’m left feeling the gaping hole of lack of intimacy and that makes me sad and frustrated. Is there something I’m missing? A better way to meet or vet someone? An avenue I haven’t thought of? Is what I want just unrealistic?
—Missing Physical Intimacy and Maybe My Sanity
Dear Missing Physical intimacy,
Every time the concept of “friends with benefits” comes up, my mind returns to my interview with cosima bee concordia of the Drunk Church Podcast for a previous column. She reminded me that friends with benefits means actually being friends. I think of my best friend, who I’ve never had sex with and never will, and the ways we will drop absolutely everything for each other in a crisis. We’ve had simultaneous crises and gotten on the phone to commiserate, saying “Who goes first?” only to find that we’re processing our disasters together as we help each other. I think of Mitcz, who I was “friends with benefits” with over 15 years ago and remain friends with to this day. The idea of “basic caring about a friend’s well-being” with either of these people strikes me as the absolute bare minimum. What you want is a casual yet companionable serial hookup.
The hardest part probably will be finding a person who wants the same thing and knows that what they want isn’t “friends with benefits.” This is complicated by imprecise language and the fact that apps leave no space for paragraph-long explanations. I’d start with something like “looking for shared orgasms and skin-to-skin contact, and basic human decency with some [insert shared companionable activity here] but no bandwidth for emotional processing or deep friendship.” You also might ask friends whether they know anyone who fits the bill—you never know—but if you’re matched with someone, you’ll want to be extra cautious in making sure you and that person are on the same page before you proceed.
Do be prepared for the fact that life sometimes gives us what we need in ways we don’t expect. When you’re sharing a bed, snuggling, or having sex together with someone you respect and feel comfortable with, emotions have a way of happening. This doesn’t mean you’ll necessarily stumble into Big Romantic Love, but you might find yourself with a real friendship on your hands. You’ll know it’s real when you’re feeling more energized and supported after your interactions with them—regardless of the direction of care—instead of drained and exhausted.
—Stoya
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About 15 years ago when I was in my early 20s, I dated a woman who I’d known previously as an acquaintance. We were never that serious, but we did have sex multiple times over the course of a few months. Looking back on this, I am mostly embarrassed by my lack of ability to be a decent sexual partner.
