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,
This last year I’ve been single for the first time in my adulthood essentially (I’m a 30-year-old mostly straight/kind of bi woman). I’m back on dating apps and seem to have luck connecting with people. Although I have barely any experience casually dating, it’s something I want to experience. The thing is, I have what feels like a real problem concerning hookups: I don’t come easily. I can almost never “get there” with partners—even with long-term ones. Masturbation works for me but even that takes a while. I’ve tried toys, I’ve read books, and researched the sexuality spectrum. I don’t feel like the categories of asexual or demisexual really apply to me. (I fantasize about sex a lot and have hooked up with people I don’t have feelings for, to name a few.) I need to have a genuine sense of safety and connection to get off.
Lastly, I don’t feel like I’ve had a partner (they’ve all been male) who’s been truly invested in helping me orgasm. Some don’t really try or care. Some have tried, but ultimately it ends up with them exhausted and me frustrated and embarrassed. Even when I do come, the vulnerability along with the effort just makes me feel ashamed. I don’t want to burden a partner (especially a new one) with my emotional issues around sex. It would be easy to say this is a scenario illustrating that men aren’t invested in women’s pleasure, which is partially true here, but I don’t think that’s the full story. Don’t get me wrong—I want to come, especially when I’m having hot sex with someone, but I’m anxious to ask a partner to try harder, which in turn makes it harder for me to get off. You might see how this turns into an endless feedback loop.
So first off, what can I do to come more? And secondly, how do I bring up the fact that orgasming is hard for me to new partners, without feeling embarrassed, or without them taking me for granted (the “she doesn’t come so I don’t have to try” mentality)? I just want a fulfilling sex life where connection and security are present, without having to be in a monogamous long-term relationship.
—It’s Been a Rollercoaster and I Want to Get Off Now
Let’s separate monogamy from long-term relationships, as they don’t necessarily require each other. More importantly, time is what connection and security need to flourish, and it very much sounds like you need both of those to have the kind of sex you enjoy. You can have ongoing hookups. You can have friends who you also have sex with. You can have all sorts of different types of relationships that aren’t monogamous, and aren’t committed in the ways that we typically associate with romance.
As for bringing up the fact that you need specific conditions to come, you might feel embarrassed at first. But practice will help with that. And someone might take you for granted—with the mentality you describe or in several other ways. If that happens, move along to the next one. Ultimately, you can set yourself up for success by trying on a few different phrases in the mirror. Something like “My orgasms are a challenge,” or “I need to feel safe and secure to get off.” Whatever you feel most accurately and succinctly describes your situation, practice saying those words out loud. Type them in the app’s chat box. Get used to divulging that information.
Practice will also help you feel more confident telling your partners to try harder, and in the ways you need them to be putting in more effort. That’s what you’re going to need to do if you want to come more—communicate your needs to your partners.
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Dear How to Do It,
I recently reopened a long-distance, non-monogamous, relationship with someone I lived with 30 years ago. The sex is incredible. I’m finding that with age, I’ve lost many of the hang-ups that I held when I was younger and our familiarity and trust really pushes the enjoyment of our sex to a new level for me. We play around with BDSM-lite, including hand/ankle cuffs, blindfolds, hair pulling, nipple clips, and gentle throat holding, and I love it. Can you give me recommendations of where to turn for more creative sexual play in this genre? I’d like to surprise him by initiating more ways for us to connect on this level as it has brought us much closer already.
—Naughty and Nice
Dear Naughty and Nice,
The world is your oyster, but you’ll want to proceed carefully when it comes to surprises. During sex, surprises can go sideways very rapidly, so you’ll want to be very cautious—it’d be a shame to harm that trust the two of you have built. You might invest in some gear (lingerie, or a costume) that fits with the types of interactions you’ve been having. You might try an exceptionally light slap on his face or butt cheek if you’re topping—the merest suggestion of the idea of a slap, really. If you’re more on the bottoming side, you might request something you’re curious about. And, most usefully, consider having a conversation about what each of you is enjoying and what you’d like to explore. You can use one of many kink checklists out there, read or watch some erotic material together, or simply talk, face to face, about what you’re having a good time with and want more of. You’ve got this.
Dear How to Do It,
I (28F) want to surprise my boyfriend with a special, sexy night for his upcoming birthday. Honestly, we’re pretty routine when it comes to our sex life so we’ve never actually done anything like this! I’m not really sure where to start. Should I get some lacy undergarments, a sex game, ask him for his deep dark wishes prior to, or some combination of all of the above? Also, I feel pretty shy about sex in general but want to feel confident when doing this instead of completely embarrassed. How can I get more comfortable ahead of time?
Dear Birthday Wish,
Set yourself up for success by staying near, or even within, your comfort zone. And, as I said to the other writer, surprises can be combustible, so I’m happy to hear you are considering asking your boyfriend for his deepest wishes beforehand. That’s a good idea to run with. I do think a sex game or some lingerie is tame enough to be low-risk, though.
Think about what you’re most comfortable with. Imagine yourself in the lingerie, presenting the sex game, or whatever else you’re considering. What feels less embarrassment-inducing and what feels more stressful? Let that guide you to your decision.
I just got to have a sexual experience with a guy I’ve been desiring for a long time, and it was such a disappointment. He could not penetrate me. We tried all kinds of positions.