The Playboy Advisor

Q: I’m a 33-year-old straight man, and my problem goes all the way back to when I lost my virginity at 14. I’m sure I wasn’t the only high school freshman who climaxed the second a girl touched his dick, but premature ejaculation has hounded me ever since. I’ve had three long-term girlfriends, and with each of them I’ve gradually been able to last longer than 30 seconds—but even then my entire sexual ride consists of worrying the big O is coming too fast. After my last relationship ended, I got on the apps for a while but promptly gave up; the embarrassment was too much. It didn’t seem to matter whether I’d been drinking or not, whether it was morning, day or night or whether I was mildly or extremely attracted to the woman. At this point I’m ready to ditch sex altogether and stick to masturbating; at least then no one else will know how quick it’s over. What’s wrong with me?—M.R., Lexington, Kentucky

A: Above all, know that you’re not alone. Premature ejaculation, or PE, affects at least 30 percent of men. In my clinical experience, guys with PE are no different from guys who don’t have it in terms of masturbation style, porn use, family background, sexual history or mental health, meaning PE is something you were likely born with. But that doesn’t take away from the embarrassment you feel. Here are a few suggestions (including one you can try as soon as you finish this article) that will help you have longer and less-fraught sexual experiences.

The first is a masturbation exercise. Edging, also known as the male multiple-orgasm technique, can bridge the gap between masturbation and intercourse. The idea is to identify your point of ejaculatory inevitability—that first contraction of an orgasm—and interrupt it before you go over the edge. When you feel an orgasm coming on, stop! This releases blood from the penis, which in turn cycles the process back a bit, giving you a longer pre-orgasm interval. Try doing this with the help of some new, extra-hot porn. By approximating the intensity of a one-on-one sexual encounter, you’re more likely to be ready for your next partner.

When you’re with that next partner, shift the emphasis away from your penis. Even without PE, there’s a big orgasm gap between men and women due to factors such as their arousal times, and there’s no way a man with untreated PE can get a woman all the way there. Become an expert at oral sex and manual stimulation. Incorporate sex toys. Use your words. Create fantasies. Do whatever you can either to make your partner orgasm first or to get her right to the edge so you can climax together. (Another tip: Numbing sprays like Promescent can delay orgasm by desensitizing the penis. They’re not a total solution but worth a shot.)

The next line of intervention is an SSRI, a common class of anti-anxiety medication with the side effect of delayed ejaculation. It might make sense to talk to your doctor about a low dose, particularly if your anxiety and depression around PE are intense. It’s not a panacea, but it can be part of the solution—and there should be no stigma attached to SSRI use.

Dealing with PE is complicated, and managing it takes real effort. The good news is that with a little work you’ll likely see a big payoff. So don’t give up till you’ve experimented with multiple approaches. And when you’re back in the game, remember that lasting longer doesn’t mean your partner will inevitably go straight to pleasure town. Instead of thinking about how long you last, ask yourself, How do I become an arousal-generating person?

Q: I’m an 18-year-old straight woman who has been seeing the same guy for months—but I’ve never finished when we have sex. When we use toys I become self-conscious and can’t climax even though I use the same things when I’m by myself. At this point I feel pressure to achieve orgasm just because it’s been so long. How can I overcome my stage fright?—J.A., Arlington, Virginia

A: Orgasms between partners can be inconsistent or even nonexistent in ways that aren’t true of self-stimulation. What do you think it is about sex with your boyfriend that makes it so difficult? Could it be a lack of clitoral stimulation? Not enough foreplay? Something about the environment that makes it difficult to relax? Certainly worrying about your orgasm doesn’t help, as any form of anxiety during sex is a major arousal inhibitor.

If you’re not already talking about this with your boyfriend, you should be. He should know that orgasm doesn’t have to be the destination during sex; there are lots of other parts of the journey, and you should be getting the most out of them. I would also ask you to think about the parts of sex you really enjoy. Is it the kissing, the touching, maybe giving him pleasure? For the time being, see if you can create a sex menu that doesn’t include orgasm but allows you to enjoy other dishes that may be just as delicious.

I would also encourage you to add some psychological stimulation. By this I mean fantasizing together, watching couples porn, listening to an erotic podcast. The brain is our most powerful sex organ, and it has the ability to turn us on and off. Right now the anxiety is turning you off, so I want you to fill your head with stimulation that turns you on.

Q: I’m an 18-year-old male who’s never had sex because I’m afraid of getting an STI. How can I get over my fear?—W.R., Lafayette, Indiana

A: Fear is the key word here. It’s impossible to have totally safe sex, but you can consistently have safer sex—and a little bit of that fear of yours, balanced with your passion and enthusiasm, can make you a great lover.

With an appropriate amount of fear, you’ll be motivated to always use a condom when having intercourse. A little fear can also inspire you to avoid making sexual decisions while under the influence of drugs or alcohol, which of course can lead to reckless choices. And your fear will, I hope, inspire you to read up on STIs. I recommend Columbia University’s Go Ask Alice website and that of the American Sexual Health Association.

If you’ve ever had oral sex you should get tested just to know you have a clean slate. If you haven’t gotten an HPV vaccine yet, you can do both at the same time. Some STIs are symptomless; when you’ve been tested yourself it’s easier to ask a potential partner if they’ve been tested. If you’re serious about someone and think you may want to see them again, you can start with less-risky behaviors, such as kissing and manual stimulation of the genitals, and wait until your partner has been tested to move to riskier behaviors such as oral sex and intercourse. There’s nothing wrong with taking the slow route: It allows more time for passion to percolate. Believe it or not, safe sex can be hot sex.

Q: My boyfriend has a lower libido than I do. I want him to pursue me—I rarely enjoy being the aggressor—but he’s happy to have sex once a week or less. How do we reconcile our differences?—G.P., Newark, New Jersey

A: Low desire is common in both women and men, but sometimes men have to live with the pressure of feeling they should be walking hard-ons. It’s also possible your boyfriend experiences anxiety around the discrepancy in your libidos.

All of which is totally natural. Maybe you’re able to have what’s known as “spontaneous desire,” in that you can experience a sexual cue and get turned on quickly, and maybe your boyfriend has “responsive desire,” meaning he has to build on sexual cues to experience desire. Desire isn’t the first thing he experiences; it occurs once he’s somewhat aroused. If that’s the case, you may have to change how you think about sex. Your spontaneous desire may have to be the kindling to get him fired up, and his sense of passion or aggression or whatever it is that you crave may have to come a bit later.

See if you can create erotic sparks outside the bedroom and decouple those sparks from any pressure or invitation to have sex. If you usually have sex on the weekend, make a rule that Monday through Friday is an erotic-spark zone where you can engage in small bursts of sexual and erotic connection without feeling they have to lead to sex. Whatever you do, remember that desire, like the stock market, goes up and down and that countless variables can affect libido: stress, mood, lifestyle, health, medications, body image—you name it. Go easy on yourself and your boyfriend as you seek that sweet spot.

Q: I recently got out of a toxic relationship that was on and off for about three years. For the first time in what feels like forever I’m happy and at peace. That said, I’m finding it hard to put myself out there again. This is made extremely difficult by how horny I am! Considering sex is pretty much all I think about now, do you have any tips on how a straight woman in her early 20s can get back to dating—and banging?—H.G., Los Angeles, California

A: Congratulations on getting out of an unhealthy relationship. Now you can focus on living a healthy life—which, yes, includes sex. Of course a difficult relationship will chip away at your self-esteem, and getting back into the swing of sex and relationships can be nerve-racking. So give yourself some time to get the lay of the land.

I hear that you’re horny, but what kind of sex are you looking to have? Some fun, no-strings-attached sex, something more relational or something in between, like a friend with benefits? I think it’s important to get in touch with your sexual self before rushing into the actual deed. Start noticing who and what turns you on, what makes you feel sexy and alive.

From there, let the world know you’re seeking and that you spent too much time with your gaze focused on the relationship. Connect with people who make you feel good about yourself, and know that you’re in charge. You can go out on a date, you can flirt, you can fool around—and you can say no at any point. The sexual brain has two systems that operate at once: a sexual excitation system and a sexual inhibition system. It’s called the dual-control system, and my colleague Emily Nagoski, author of the terrific book Come As You Are, compares it to a car: Your sexual accelerator needs to rev up, but you also have a brake you can step on at any time. So get out there and take a joyride.

And because you’re so horny, I hope you’re masturbating. The past three years have been a golden age in vibrator design, so start giving yourself the pleasure you crave and deserve.

Q: I’m a bi woman in her early 20s. My 35-year-old partner of six years told me in an argument that we don’t have sex anymore because he’s no longer attracted to me since I gained weight. He has apologized several times and tells me how beautiful I am daily, but I have a hard time believing him. We’ve started having sex again, but it’s awkward. I don’t want him to see my body, and he’s afraid he’ll somehow hurt my (admittedly sensitive) feelings again. This makes our sex passive and cautious. How do we work through it?—E.W., Camden, New Jersey

A: People say shitty things to each other when they argue and tend to focus on faults. It’s great that he apologized, but I understand you still feel hurt by his comments: Sexual self-esteem can be hard to hold on to. The reality is that we all age, our bodies change, our weight goes up and down, and somehow we have to keep navigating a world that celebrates youth, thinness and unrealistic ideals of perfection.

I know he’s repeatedly told you he’s sorry and thinks you’re beautiful, but have you been able to have a conversation that goes beyond apologies and reassurances? Have you been able to say that you want to believe him and move on but that part of you feels hurt and rejected, or part of you is scared he might not be attracted to you anymore? Maybe you need more opportunities to come to him with your vulnerability—and he needs more opportunities to be empathetic and soothing.

Also, try having a few good experiences of real-world sex together and put this behind you. You’ve been together for six years, so try adding new elements that will bring out some excitement and passion in both of you and get you to that aroused place where you can’t keep your hands off each other.

Bottom line: You had an argument, and you need to repair. And when you have an argument that touches on sex, sometimes the repair is in the sex itself.

Q: I’ve been with my boyfriend for a year now, and for about half that time we’ve been in a long-distance relationship. I’m very forward and sexual, but he saves his affection for when we’re in the bedroom—or, in our case, when we’re in the same town. I think sexting is an important part of any relationship, long distance or not, but he won’t get onboard. It’s truly frustrating. My argument is that since he’s never done anything like that, he shouldn’t reject it just because he feels uncomfortable. How do I make him feel more at ease in the sexting realm?—T.C., Buffalo, New York

A: How cool that you’re so open to keeping things sexy and alive when you’re apart. I think you’re totally on the right track, and there’s so much you can do—from sexting to Skype sex to remote-controlled sex toys—to stimulate each other long distance. But those options may take you to deeper waters; in that case, he has to start by dipping his toes in the shallow end.

I like that you’re able to “mentalize” what he might be experiencing: mainly lack of comfort and experience. Have you tried having a conversation with him in which you appeal to these vulnerabilities—something like “Hey, I know sexting may be out of your comfort zone, and I’m sorry if I’m pressuring you. It’s just that I’m really into you and it’s hard to be apart. And when you shut me down, it makes me feel rejected.” In that statement, you’re trying to do a few things: You’re giving yourself a way to open up the conversation and acknowledge his vulnerabilities while expressing yours. He may get defensive at first, but don’t let him escalate. Just keep coming back to the vulnerability.

Ideally, getting off the main floor of life, as I like to say, and going down to the basement, where all those vulnerable emotions are safely stored, will set the stage for experimentation and sexual connection. Finally, whether you envision sexting as words, photos or both, you can start the process by sending him simple questions to which he can respond yes or no, such as “I’m having a sexy daydream about doing [fill in the blank] when I get my hands/mouth on you. Is that something you’d like?”