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’ve had somewhere around 15 to 20 sexual partners during my life and the sex has ranged from very disappointing to quite good and very satisfying. But a decade ago, I spent a month having the most electric, mind-blowing, hot sex of my life with a guy. The chemistry I felt with him was off the charts. There wasn’t something different about the type of sex, the moves were all the same tried and true sex positions. So the difference must have been the guy. He wasn’t classic Hollywood hot, but then years later I can still picture his face perfectly and find him so so attractive. We weren’t compatible for a romantic relationship, so it ended, but I have been hung up on that sex since then.
About once a month since then, I’ve had a vivid sex dream about this guy to the point that it wakes me up. During sex with other people, I’ll close my eyes and fantasize that whoever I’m with is this guy to make it hotter. Every once in a while I think about tracking him down to take another ride. Even though I do have good sex, I often find myself comparing it to that guy and it doesn’t hold a candle to that experience. Has he literally ruined all other men for me? Am I ever going to get a second encounter like this? Do we all get one once-in-a-lifetime sexual connection that I should look back on this fondly but be content with the good sex I have with other people? Are the odds in my favor that if I sleep with another 20 men, one might have that spark?
—Seeking Best Sex Ever
Dear Seeking,
There’s no simple answer here. It’s possible that this lover from 10 years ago was the best sex you’ll ever have. It might have been his energy, or how you were feeling at the time about your life and self. It might have been something about the exact dimensions of his cock, or that his face is the most attractive in the world to you. His pheromones. Your hormones. The way the planets were aligned for that blissful month.
But you’re reducing your chances for success by closing your eyes and remembering this ghost. Hot sex comes from connection. Connection requires being present. You may be missing opportunities to build a rapport that could be just as wonderful as this month-long fling. What I’m saying here is that sometimes, earth-shattering eroticism is something that grows over time, and you have to nurture intimacy to get there.
That said, instant, wildly intense connections do happen. And, yes, you might find another overpowering attraction if you got out there and met another two, 20, or 200 people. If you decide to go searching, keep your eyes open so you can spot the sparks.
Dear How to Do It,
My husband and I (early 30s woman) recently opened our marriage a bit to include swinging and friends with benefits. Things are going well for the most part—I’ve found people I jive with and feel comfortable with, but I’ve run into a very embarrassing problem.
When I am with said people, we are both fully enjoying ourselves, but it is impossible for me to climax. At first, I thought maybe it was just nerves or my partner didn’t have a technique that matched my desires (not a problem, that’s where communication comes in!), but even after we part, neither my husband nor I can get me to climax. I don’t mean to brag, but he and I are both very skilled at that, but it’s like I’m a car going 60 mph but my wheels aren’t touching the ground and that climax is NOT HAPPENING.
Could it be possible that I find my partners just too damn fine and I am just overstimulated and overexcited to a point that I can’t climax? How would I even approach fixing that? I don’t want them to think I am not having a great time.
—Stuck in the Plateau
Dear Stuck,
It’s absolutely possible that you’re overstimulated by how hot your swinging encounters are, and unable to climax because of that. Sometimes a similar thing happens to me, after several orgasms, and I’ve found having my vulva slapped hard—think sharp pain, right on the clitoris—can be the right kind of stimulation to get me over the precipice again. If this isn’t already a part of your sexual repetoir, I think it’s worth a try. Keep in mind that the same pain sensation can feel very different at different levels of being turned on, so you’ll want to give it a shot when you’re at the peak of your arousal.
It’s also possible that you’re reluctant to let go entirely with people you don’t know very well, even though you’ve established some rapport and feel comfortable with them. You might try, using your car metaphor, to slow down to about 25 mph and see if you can get some information from your body and thoughts. Are you holding tension somewhere? Is there something in your mind that you’re distracted by? If you can catch some clues, you know what directions to reflect on later.
Mostly, though, you know that orgasm isn’t the whole point of sex. And your partners probably do, too. If it’s causing you anxiety, it’s worth a conversation to let them know that you’re having an absolute blast with them regardless of climax.
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Dear How to Do It,
I’m in a long-distance relationship with my boyfriend who I met online. When we first started dating (completely online), we sexted quite a bit and occasionally did phone or video sex. We eventually met up in real life and did have great sex in person as well! But now when we’re apart, our sex life seems to have gone a bit dead.
Now, my boyfriend finds visualizing scenarios to sext about and typing them up less exciting and more tiring. Phone and video sex are pretty much off the table because he is hardly ever home alone nowadays and his walls are super thin. He likes exchanging pictures sometimes, but I need more than that to get off. We even got a toy that can be controlled via an app, but it seems odd to use it while not talking to each other in some way. I guess it’s just the honeymoon phase wearing off, and he’s tried to accommodate me, but I clearly have more of a need/desire for this than he does.
We’ve talked a lot about ways to try to reignite his interest in sexting or do it differently to make it less stressful somehow, but I just miss the eagerness and excitement from the beginning of our relationship. I would rather be together in person again, but as it is, we’re having the same LDR as at the beginning, but with none of the sex. We still love each other like crazy and are planning to be together in the long term, but the waiting is hard. Any suggestions of how we can still have sex together while apart?
—Geographically Challenged
Dear Geographically Challenged,
When you say that your boyfriend finds visualizing scenarios to sext about and typing them up less exciting and more tiring, I’m wondering if he’s been doing the bulk of the labor here. Think back—who contributes most of the creativity? Scroll through those messages: Are there big blocks of text from one of you and single lines from the other? If he’s been putting forth most of the effort, you might tell him that you’ve realized how much work he’s been doing to keep your sexual connection going and say that you’d like to try swapping roles with you taking the lead.
Thin walls and cohabitation seems like an impasse for phone and video sex. If he’s shy, or there are other reasons to keep the sexual volume down when others might hear, that’s the way things are.
Could you build your own fantasies based on the pictures he sends you? Can you find a way to get sexual enjoyment out of sending pictures to him, since he likes that? And is there a way to make use of your memories of the hot sex—and sexting—that you’ve had previously while using the remote controlled toy?
It also may simply be that having sex together, in the same room, alleviated some of the tension the two of you had built and took some of the shine off of sexting. Lean on your masturbation skills while you’re waiting to have physical contact again, and try not to worry about the honeymoon phase wearing off until you’ve seen how you interact in person now.
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Dear How to Do It,
I am not graceful in any way, but also not sexually inhibited and I need help. An endless string of googling has given me many tips for how to enjoy being on top with a man (which I already know, thanks), but very little information about how to gracefully get INTO this position, especially with a new partner. I’m 50, short and apple-shaped, with short arms and decent flexibility. With a few men I’ve found it easier just based on their physical attributes, but a lot of the time I feel like a total klutz and am afraid I’ll kill the mood, no matter how much I want to not be in my head about it, which is decidedly NOT sexy. As a former musician, I have a tendency to want to practice things to get better at them. I’ve got a Liberator Pulse and have tried to work on this technique, but it doesn’t seem to help in reality. Psychoanalysis aside about being in my head, I need some practical tips on how to do this.
—Sexy Klutz
Dear Sexy Klutz,
The more practice you have with a variety of bodies, the more quickly you’ll be able to adapt to new spatial specifics—how wide they spread their thighs, and what the angle of their erection is. You can set yourself up for success by taking your time. You don’t need to do this like a gymnast.
There are several ways to get into cowgirl. You can lay on your side, with the front of your torso pressed against their side, wrap your top leg over them, and roll onto their body. You can place your hands on the middle of their chest (between the pectoral muscles, not on the tender area just under the spot where both sides of the ribcage meet) and mount like you’re getting on a horse. You can stand above them and squat down. Each way of getting into the position will result in a slightly different experience of cowgirl.
You’ll still probably have clumsy moments. We all do. You don’t often see awkwardness in film, romance novels, or pornography because of editing. These mediums are in the business of entertainment, not sex education, so they edit for smoothness and flow. While you can’t guarantee you’ll never do something klutzy during sex, you can practice laughing it off and moving on. Think of it as a kind of libido resilience. Apologize if you’ve hurt them, have a giggle if you’re able to find it funny, and take a deep breath and get back into the moment. Good luck.
—Stoya
More Advice
I have a really thorny ethical question I can’t quite wrap my mind around. I was seeing a guy earlier this year. The relationship was long-distance, which is why it took me way longer than it should have to realize I was his dirty little secret: He had a live-in girlfriend, despite pressuring me to commit to monogamy. As soon as I found out, I cut off all contact with him. Since we broke up, I’ve been dating around, and I recently had a Pap smear that came back abnormal because of HPV. I have follow-up testing due this week and have alerted my current partners about what’s going on, and have spoken with everyone else I’ve slept with in the last couple years—except him.
