How to Do It is Slate’s sex advice column. Have a question? Send it to Jessica and Rich here. It’s anonymous!
Dear How to Do It,
This is more a question on how to get other people NOT to do it, but here goes. I have a lot of very close friends who are still single and I love this for them. I’m constantly a person they can come to for venting and a listening ear about their dating struggles, etc. I myself have been in a long-term relationship for many years now—but I’ve always worked to make sure that hasn’t affected how much time and bandwidth I have for the dear friends in my life. We hang out several times a week, and often will go out dancing or to the bars at least once a month.
The struggle is on these nights out: A lot of my girlfriends do not hesitate to find a hookup on these nights out and head out with them early and kind of leave me hanging. And even on the nights where they don’t find anyone, I can feel their attention going into preening and scouting for an eligible bachelor. We used to do this a lot when we were younger and single, and it was great fun. We’d chat about the guys we found hot and schemed ways to talk to them. And I don’t mind being a wing woman every once in a while. But sometimes I wish we could just enjoy each other’s company, without having to prioritize finding their next sex partner amongst the crowd. Why can’t we just dance!
Anyway, this is probably something I should’ve said to them a long time ago but now I feel like it’s a frustration that’s been bubbling and I can’t figure out how to bring it up. How do I talk to them about this without blowing it up into a huge deal? Should I go there or am I being a selfish coupled person?
—Dance Dance
Dear Dance Dance,
I feel for you. It’s tough to face change in life, especially when it seems like the way things before the change are still within our reach. The issue here is that you’re the one who changed. You are no longer single and doing single things, but you’re still hanging out with people who are. That’s fine, but you should understand that they aren’t obligated to change their lives for you. They’re still going out, like you used to, to get laid. You’re going out to bond with your friends. That’s not quite as misguided as using Grindr for networking, or visiting a slaughterhouse to pick up some asparagus, but you’re setting yourself up for disappointment all the same.
The cost of hanging with your friends at a club is that they might leave you hanging … alone. This is not them being bad friends—this is them being people who are in a club. Some amount of acceptance of this fact will be key to continuing harmony within your friend group. If your relationship were only about going to the club, and you were constantly being left dancing on your own, I’d say a more varied approach to sharing time was in order. But you say that you hang out with these people several times a week and do clubs once a month. That’s really not so bad–it seems like you’re getting in plenty of quality hang time that isn’t interrupted by dick distraction. Your best bet is to bring along another married or coupled friend so that you know you’ll have at least one buddy, or expand your club-going to include venues/nights that you can enjoy with your husband.
If these really aren’t an option then maybe you can draw up some kind of negotiation along the lines of: Every so often, the goal of the night will be to stay in a unified group, and not go off. To be completely fair, these you-style hangs should be sporadic—if there are six of you in the group, for every five club nights their way, you get one (so then two a year). This is an option, but it may not be a satisfying one for all involved—you’re basically asking them to not do their thing for your sake. What if on one of these chaste outings, a friend encounters the hottest guy she’s ever seen? She should be able to go after that, right? So even within a stricter plan, I encourage you to be flexible and understanding. Let your friends get the dick they desire.
Anyway, that’s at least a sketch of a proposal that you can have in your pocket if and when you broach the subject. I would bring this up agnostically—just tell your friends about your experience and ask them if there’s anything that could be done to remedy the typical outcome of you being left while they go off. Solutions offered by them will be theoretically easier for them to abide by. You can bring up the sporadic stay-united plan I mentioned in the paragraph above and see what they think. But I think you should also prepare yourself for no change at all—part of being friends with people is letting them do their thing, accepting it, and remaining loyal anyway. This is not me telling you to endure mistreatment, but to urge you to empathize and accept your friends where they are. I think everyone will be happier in the long run, and then when they’re married one day, you may find they are more your speed. Play the long game and keep important people in your life.
Dear How to Do It,
This may not be the weirdest problem I’ve had in my life, but it’s up there. I love my girlfriend, we’ve been together two years, and we’re talking seriously about moving in together and getting married. Our sex life is really good and our dynamic tends to revolve around a lot of non-penetrative (multi-orgasmic) foreplay for her followed by penetration. This has worked out great!
Except, about a month ago I was super turned on and came really quickly inside of her, two-pump-and-dump style. That seems to have unlocked something inside of her because she also came multiple times after that (usually she’s one and done after penetration.) The next time we fooled around she turned on the jets, so to speak, after penetration started and I came quickly and the same thing happened. I was actually apologetic and very self-conscious at the time and she told me not to worry about it and that she felt flattered. Except, the next time I lasted longer, and after she realized it wasn’t happening quickly, she got almost frustrated and we couldn’t get her off. But the next time it happened quickly she was just as turned on as the first time.
I’ve tried to talk to her a little about it but she gets shy, I think it’s partially her having difficulty articulating her desire and partially her trying to protect my ego (which is appreciated). But I’d like to feed this if I can.
So, all of this is to get to my question: Is there a concrete way to achieve orgasm more quickly? Right now the only things that have worked have been mental headspace stuff, which is nice but not something I can consistently set up, and I’d like to find a way to do this more physically.
—Looking to Get It Done
Dear Looking to Get It Done,
Try going without masturbating a few days before sex (or entirely). You may be so excited once you do get some relief that you respond very quickly. Another thing that might be useful is edging between sex sessions—that is, masturbating up to the point of no return and then backing off. You can do this once or a few times, just don’t come. It can prime you for a quick shot when you finally allow yourself full stimulation. It’s not a guaranteed method for quick orgasm, but it may work for you and is at least worth a try.
You should be aware that premature ejaculation as a fetish/kink may go against conventional wisdom (that is: the more stamina the better), but it is not unheard of. I remember during the early days of this column, someone said to me, “It’s amazing how many people out there like when guys come quickly,” because we answered quite a few questions like this. There’s, in fact, a subreddit devoted to the subject with, at the time of this writing, 82k members: r/prematurefetish (NSFW). You should poke around there—sometimes members offer tips for a faster shot (like here and here). Those techniques are for more long-term recalibration, and they are predicated on anecdotal evidence, so take them with a grain of salt.
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Dear How to Do It,
I’m a trans guy who’s been on testosterone for a year and a half-ish. One way my gender dysphoria manifested when I was younger was that I didn’t like acknowledging the existence of my genitalia. The only way I felt I could comfortably masturbate was by humping the bed. Now that I’ve had some clitoral growth from the T, I feel a little more comfortable touching down there, but now I don’t know what I’m doing (like I ever really did, three cheers for US sex ed).
Though I’m more comfortable with the idea now, sticking my fingers inside my vagina isn’t really an option (I hate the smell and feeling from the vaginal liquid on my hands, and a side effect of T is that I get a lot less wet, so insertion isn’t easy). I want to (read: probably should) change the way I masturbate, because I have reason to believe the position I favored for my previous method (facedown on a pillow with my head turned to the side) is/was putting pressure on my teeth/jaw and straining my neck in a way that won’t be good in the long run.
Should I try some toys? Where should I look for those? Do I just start stroking my dick that’s literally the size of a newborn baby’s and hope for the best? It feels like I’m at a halfway point between male and female genitalia, but my body’s doing neither correctly.
—World’s Tiniest Dysfunctional Richard
Dear World’s Tiniest Dysfunctional Richard,
You want to-slash-believe you probably should change your masturbation position, but it’s working for you, so why reinvent the wheel? You may be able to keep it with a slight tweak: a massage table headrest or rolled up towel placed at your forehead to allow you to keep your head straight without straining your neck. It’s worth trying out.
But you did express a desire to venture out beyond your current technique, so to help answer your question, I reached out to Dr. Damon Constantinides, a queer and trans sex therapist and coach, who runs virtual sexual pleasure groups for trans and queer folks, including the eight-week Trans Masc Sexual Pleasure program. (His Instagram is here and his TikTok is here.) A few orienting words might be useful here. Constantinides felt that the disparagement of your body in your letter was effectively “talking about dysphoria without naming that language—the experience of dysphoria.” He continued: “This idea that it’s a halfway point between male and female genitalia: I’m like, but does it matter?”
In contrast to your current mindset, Constantinides encourages you to pursue what he calls “gender euphoria.” He explained: “A lot of times when people define gender euphoria, it’s like some magical, amazing experience, but really, it’s just the experience of feeling normal. And when you have dysphoria, you didn’t feel normal, right? So this doesn’t have to be like some magical thing.” Finding your normal (and you can sub in any word here if you don’t like “normal”—like “equilibrium” or “rightness”) is going to take experimentation. You should be looking for what feels right—not as defined by external forces, but to you as you are right now. “Experimentation is data,” said Constantinides.
Masturbation is a highly individualized practice—no one besides you can tell you how to do it. But, Constantinides did have some suggestions to push you in a satisfying direction. “A lot of the trans men that I talk with really like their dicks touched the same way that cis men do, which was not how they did it before for a lot of them,” he said. “So think about going up and down on the shaft,” as opposed to in circles, as many people do when stimulating a clitoris. You can try vibrators (“They can also be something that men use, and that can be a feeling that can feel really good”), sleeves (like these sold at GenderCat), or an air-pulse toy like the kind that Satisfyer makes. That last one Constantinides says he learned about specifically from people in his Trans Masc Sexual Pleasure groups. Other outlets to shop for trans-friendly toys include Transthetics and Banana Prosthetics. You may also want to look into a lube to keep things slick–for my money, Swiss Navy silicone lube has never steered me wrong.
Keep in mind that early on in your testosterone journey, you may have experienced (or still be experiencing) extreme sensitivity—know that this can change and thus your masturbation technique may need to adjust. The key is to be flexible and curious. You can also glean inspiration from ethical trans porn. A Google search should get you on your way. “My whole thing is we don’t really have a lot of mirrors,” said Constantinides. “Since we don’t have a lot of sexual role models, or erotic role models, then we get to do it for each other. And then we get to really support each other in connecting with sex in the way that feels best for each person, which is going to be different for each person.” Good luck!
Dear How To Do It,
I know people experience sexual attraction and romantic attraction distinctly, and someone can experience one without the other. I also know that, for many people, sexual desire is akin to a need, and you can fulfill this need in many different ways (in a monogamous relationship, polyamory, casual sex, professional sex workers, porn, etc.).
My question is: are there similar options for people who want to fulfill romantic desires, and feel them strongly (as a need), outside of a mainstream committed romantic relationship?
Like, is there a group or app for people seeking “casual romance”? Romantic dates, but no expectation of increasing commitment, exclusivity, or sex? Are there romance professionals who write love letters, have intimate phone calls into the night, and hold your hand on evening walks on the beach—but don’t have sex? Is it possible to open up a relationship to romance outside the marriage or LTR, but not to sex, because you’re happy with your sex life and partnership overall, but your partner is no longer able to give you romantic love or romantic affection?
If a person chooses to spend alone time with interactive romantic fiction, using an AI boyfriend/ girlfriend app, or fantasizing or writing fanfiction about romance, is that about the same as masturbating to porn? Or is that more like cheating (if partnered) or maladaptive (if single)?
—Hopeful Romantic
Dear Hopeful Romantic,
There are romance professionals that do the kind of work you seek—specifically Japan’s “sheep boys” who will cuddle you, cook you dinner, and sleep at your place for an hourly rate (Karley Sciortino reported on them and guys who do similar hourly companion type work for Vice a few years ago). It’s probably fair to assume that you’re not writing in from Japan, but boyfriend/girlfriend experiences are common in the U.S., as well—you just may have to search for options in your area. There’s, of course, the sex-worker cliche of, “What people really want, more than sex, is attention/a listening ear,” so it does seem possible to contact someone who is offering some services but not advertising the ones you’re seeking, and asking if they’d be down.
In terms of apps, I don’t think one has been developed for romance without sex specifically, though there are asexual apps out there like Taimi. You could also investigate something like Feeld, which tends to cater to very specific taste (without being fetish-centered). You might also have some luck looking in asexual spaces like r/asexualdating. I don’t know how you identify and please feel free to reject any and all labels, but it sounds like you may be an alloromantic asexual (or at the very least, that shorthand might be useful in your pursuit of connections).
While your letter is philosophically probing in nature, I feel that your last paragraph takes a turn. You’re making me think about AI now? NYC Pride was just days ago—I don’t know if I’ve worked back the mental capacity to do this justice. But OK, I’ll try: I don’t think it’s bad to pursue anything that doesn’t hurt others but satisfies something within yourself. Even if the stakes were lower and this were not about a romantic outlet, per se, but a way to spend time (a hobby, if you will), I would support it. I think given your interests, what you describe in that last paragraph is probably on par with masturbation. It could only be considered cheating if your partner specifically asked you not to do it, and you agreed and then reneged. As with everything, you’ll ideally want to practice moderation and strike a balance between your AI time and non-AI time, but otherwise, I see no reason why you should feel bad about doing something that you quite enjoy.
—Rich
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I’m in a casual, but monogamous, dating relationship of 3-to-4 months. In a recent discussion about sex, I briefly disclosed that in my past I was in a brief sexually abusive relationship. I received help and have healed, and he seemed supportive and caring about my past and recovery, however the sex we’re having now is way more “cautious” than before. Before I told him, we were very compatible sexually, but now I feel like he’s hyperfocused on not sexually abusing me due to my history, even though that’s not been an issue for us AT ALL. How do I take him off this overly cautious course?