I'm Zachary Zane, a sex writer and ethical manwhore (a fancy way of saying I sleep with a lot of people, and I'm very, very open about it). Over the years, I've had my fair share of sexual experiences, dating and sleeping with hundreds of people of all genders and orientations. In doing so, I've learned a thing or two about navigating issues in the bedroom (and a bunch of other places, TBH). I'm here to answer your most pressing sex questions with thorough, actionable advice that isn't just "communicate with your partner," because you know that already. Ask me anything—literally, anything—and I will gladly Sexplain It.
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Dear Sexplain It,
I was dating a girl for like a year. She was my first sex partner. I failed on my first three attempts to have sex, so intercourse didn’t happen. From the fourth attempt on, we only did foreplay, and I was not enough to make her cum, but she said I was good, and if I just went a little bit longer, she would have cum. Recently, she broke up with me saying that I was bad at sex. She then told me that immediately after we broke up, she hooked up with a Bumble match. She called me to say she'd had great sex with him and that our sex was terrible.
I loved her so much and thought she would have my back and support me to get better at sex, but instead, she’s now calling to rub in my face that I was bad. She has killed my self-esteem, and I feel very bad and depressed. How can I overcome that?
—The Worst at Sex
Dear Worst at Sex,
First things first, your ex is being unnecessarily cruel. Her continued communication isn't improving your mental health or making you more confident sexually; all she's doing it pouring salt on your wounds. So block her. I'll wait.
All done? Great. Let's continue. I understand why your self-esteem is in the trash. Mine would be, too. I have no way of determining how "good" you are in bed, but what I can say with certainty is that your first sexual experiences doesn't have to dictate the rest of your sex life. In fact, most people's first times are generally shit. The first time I tried to have sex, I couldn't get hard, fled my girlfriend's house in disgrace, and proceeded to cry the entire car ride home. Look at me now! I'm a goddamn sex writer who's had satisfying sex with hundreds of people.
I want to reframe how you're thinking about this. Let's get EXCITED, because you're about to embark on the wonderful journey of honing your sex skills. By the way, some guys have too much pride to do any research on the topic, so you're already ahead of the game just by reading the rest of this column. Go you!
Start by educating yourself. There are many incredible resources about building self-confidence, speaking openly about sex, embracing your desires, and enhancing pleasure. (Might I suggest a book I co-authored, Men’s Health Best. Sex. Ever.: 200 Frank, Funny, & Friendly Answers About Getting It On?)
I also recommend some online courses, like the Mind Blowing Oral online course, which will teach you how to please your partner using your hands and mouth. Pleasure educator Luna Matatas offers a range of courses online, from Dominance and submission to confidence and dirty talk. (Please note that every link is to an article at Men’s Health we have written on the topic. Read those, too.)
Learn what feels good for you, too. The more you get used to experiencing pleasure in your own mind and body, the more likely you’ll be able to tune into the moment when eventually playing with a partner again. "When someone tells you you’re not good at something, it’s easy to get hung up on technique and performance, but you’ll likely be better off tuning into connection and pleasure instead of worrying about how you measure up," said Dr. Jessica O’Reilly, We-Vibe sex & relationship expert.
Dr. Jess recommends that you "spend some time getting to know your own sexual desires, response, and values. What feels good for you? How does your body respond to specific types of touch? How do you respond to visual and aural stimuli? Take note of your response, and don’t judge yourself.”
I recommend reading The Multi-orgasmic Man: Sexual Secrets Every Man Should Know. While, yes, the book's entire purpose is to help you become multi-orgasmic, the way to get there is through focusing on your body, your arousal patterns, and breathwork.
As for when you’re eventually with a new sex partner? Let them know you're feeling a little nervous. If you two were openly talking about sex, say, over drinks, that might be a good time to share. You can say something like, “I’ve had some negative sexual experiences with sex in the past, so I’m a little nervous to have sex again.” If there isn't an organic opportunity to bring up your nerves before you get to the bedroom, simply tell them once it becomes clear that you're going to have sex (i.e., when you're taking off you clothes). Then, let them know what they can say and do (or not say and not do) to put you at ease. You’ll know the answers to these questions because you'll have read up and spent the last few months focusing on your body and pleasure! Once you share, it'll tee them up to share what they're into—thus paving the way for you to please them.
Worst at Sex, you are not the worst at sex—simply by virtue of the fact that you want to get better at sex. And you can. As Dr. Jess said, “Know that good lovers are made—not born—so you can always improve!”