How to Do It

My Sexy “Bedtime Routine” Is Starting to Keep Me Up at Night

I think this might be getting out of hand.

A woman's legs poke out from under a duvet, next to a neon "stop" hand.
Photo illustration by Slate. Photo by Prostock-Studio/iStock/Getty Images Plus. 

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 was wondering if youve got any tips on masturbating less? (Sorry if this is TMI.) Im a cis woman in her early twenties, and I tend to masturbate manually each night to orgasm just before sleep, but Id like to cut back for a few reasons:

- Ive noticed that when I take a break of say, a week, my orgasms are more intense/arrive quicker (orgasms for me are pleasant but not earth-shaking, which I know is fine).

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- My clitoris sometimes feels irritated by it when I go so many days in a row.

- Ive been under a lot of stress exacerbated by a lack of sleep, and masturbating cuts into my sleep.

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- I have some intense fantasies (think rape, power-imbalance stuff) and they make me sort of uncomfortable, but they come out when I masturbate because theyre consistently what gets me aroused. If I take a break, I find it easier to get off to more vanilla-type stuff. Plus, I think Im developing a dependency on such fantasies to get off, which I dont want to do. (Adding to that: Ive never had any kind of partnered sex, but Id like to one day, so Im also afraid of these fantasies making it impossible to orgasm with a partner/mess with future partnered sex I guess?)

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Its not to a point where its very distressing, but I do find it difficult not to. I have some mild compulsive tendencies that are probably not helping, and after a long day, my resolution to take a break from masturbating kind of just breaks because I know itll give me nice brain chemicals, like when you put a treat in your shopping cart even though its not fiscally responsible because you deserve a little something.

I exercise semi-regularly, I dont watch porn (I do read erotica), I keep an ok social life for an introvert, and this isnt to the level of I need 12-step plan,” so the internet advice I can find on the subject feels a bit like slim pickings. Masturbation as a whole is embarrassingly new to me—II started a few months ago, thanks, evangelical Christian upbringing—and I feel stupid and out of my depth here. Any advice would be much appreciated.

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— Hands Off the Bean

Dear Hands Off,

It felt like everything had snapped into place when I got to this part of your letter: “Masturbation as a whole is embarrassingly new to me—I started a few months ago) (thanks, evangelical Christian upbringing.” I don’t know to what degree purity culture proper informed your upbringing, but it seems reasonable to assume that it played some role and is worth working through specifically. (You can check this previous column for tips from a sex educator who grew up religious in the South and who now works to oppose the grip purity culture has on many young people.) This means understanding that your masturbation is not shameful. You sent me a laundry list of why it’s bad. Why don’t you take some time to make a list for yourself to detail why it’s good? I think you’ll find that the process of unlearning the supposed inherent evil of sexual pleasure is a long one. Your defense against sex may wear down over time, especially when you share it with another person and realize how conducive it can be to bonding.

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There are a few practical matters in your letter that deserve addressing. Try using a little lube when you masturbate—it may help with the soreness of your clit. If masturbating is cutting into your sleep, start earlier. Once a night is by no informed measure overdoing it, but if you want to foster more intense sensation by building up for a few days, I recommend not going to bed until you’re so exhausted that you fall asleep when your head hits the pillow. Regarding your fantasies, I understand why they’re disturbing to you in the light of day, but you shouldn’t be hard on yourself over them. Many people’s disgust response lowers during sex so that what seems like kryptonite when we aren’t aroused turns into catnip when we are. Sex allows us to get close to certain taboo subjects and effectively manage them in our minds. You aren’t ruining yourself in advance of sex: You may find such fantasies are useful with a partner, but you may also find that they don’t even enter your mind when you really connect with someone and enter the flow state of sex. Think of your masturbating as self-exploration that will help you communicate when you do have a partner—you’re banking information about yourself that you can then impart to another to maximize everyone’s pleasure. You might be kinky! You may discover you enjoy BDSM. You’re going to do a lot better if you embrace who you are and what you’re into instead of trying to suppress those things.

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Dear How to Do It,

My partner and I are both single parents in our mid-forties. Weve been together for a little more than a year. When we met, she was coming out of a relationship shed had since her early twenties. So, understandably, she wanted to date around a bit and not get tied down. And I was pretty active on apps. The relationship has grown from this somewhat casual, take it day-by-day beginning to a very important part of both of our lives.

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We have unsynced parenting schedules, and we dont get to see each other too often: maybe once-a-week plus the occasional kid-free weekend. Because of these logistics, our skepticism of the relationship escalator,” and our mutual nonmonogamy at the start, weve both continued to date other people casually. We kind of grew into this dynamic. It was never as formalized as some of the other nonmonogamous relationships Ive read about in your column seem to be. It wasnt a Decision” with Rules.” It just kind of evolved over time.

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Issues occasionally come up around validation and security (mostly from me if Im being honest), but theyre manageable, and Im very much aware that no relationship is simply all good” or all bad.” Its been a great learning experience with a lot of safety and trust to sit with the hard stuff and gray areas. Our communication about sex and our relationship is open, respectful, and exploratory.

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Heres where were stuck: We dont have a good framework for discussing other dating experiences. Dont ask, dont tell” doesnt feel right because it feels strange to wall off that part of our lives. But we dont want or need to know every detail of what the other person is doing when were apart. Some conversations start with, Tell me what you want to know,” which feels one-sided and more about providing information” than truly communicating.

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I have an unarticulated sense that interactions with other partners, rather than just being allowed,” could be an entry point for deeper connection and understanding of needs, preferences, and desires. Im just not sure how to get there. Are there questions we can ask or other tips for starting this conversation in a meaningful way? Maybe Im expecting too much and I should just be happy that weve landed on a dynamic that seems to be working for us. But I cant shake the feeling that theres so much more for us to explore together.

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— Lets Talk

Dear Let’s Talk,

So, this is why people make “decisions” with “rules.” There’s no template to work off of, which can be as alternately exhilarating and terrifying as skydiving. You have a sky’s worth of space in which to mess up or understand what it is to fly.

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But since you sort of relaxed into this way of living and loving, why not stay relaxed? Come to a mutual understanding that sex with other people is like anything you experience out there on your own in daily life: Sometimes noteworthy, sometimes even relevant, but not necessarily bearing much on your specific dynamic. Talk about it as you would with a friend. Report when it seems germane, and ask questions about things that make you curious. It’s through this casual conversation that you’ll gain more of a sense of how actually useful this information is and what your comfort levels are going forward. Open relationships often require regular conversation if the involved parties are to stay feeling secure and in each other’s good graces. I think the thing to do is to stay focused on each other and how these experiences can enrich your dynamic—the stoking of jealousy, bragging, or needless oversharing are things to avoid. Question prompts can be as simple as: “How was it?,” or, “Have a good time?” That allows the person being asked the option of a one-word answer, as well as the freedom of several paragraphs of description.

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I think inherent to your question is some amount of idealizing the usefulness of extracurricular sex. But sometimes what we seek in an outside partner has nothing to do with what’s being provided at home (or is somehow entirely different as we create our own outlets for exploration). It’s OK to have your own things! I wouldn’t put too much stock in the potential yield of such conversations, but keep an open mind and you just may grow from them.

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Dear How to Do It,

How do I balance being forthright about what I want sexually without being coercive or pushy toward my partners?

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I am a very butch lesbian in my mid-thirties, and my dating/hookup history has turned out to be a long, nearly unbroken series of pillow princesses. They are happy to have me eat them out, finger them, use a strap on them, or even fist them, but somehow reciprocation has almost never entered the picture—suddenly it’s all stage fright or “oh I’m uncomfortable with vaginas” (from women proudly identifying as lesbians—I’ve never been pissed enough to call someone on that, but a hurting part of me wants to). I find myself at a loss for how to make it clear before sex happens that I expect to receive as good as I give—every possible script I’ve thought of sounds either overly demanding or meaninglessly weak. I’ve tried toys like the feeldoe that are supposed to provide stimulation for the wearer, but they don’t work well with my build, and my current partner wasn’t particularly impressed either. Plus, that doesn’t solve the problem of feeling like my partners past and current are turned off by my body and don’t want to touch me. I know there is some tendency in the lesbian community to equate extreme butchness with genital dysphoria, but that is not me—I want to get fucked sometimes, and to have sex feel good for me, too. How do I approach that?

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— Non-Stone Butch Blues

Dear Butch Blues,

I hate to perpetuate a cliché or hold my people up as some kind of model, because Laura Dern—sorry, I mean God—knows we have our issues, but what if you communicated like so many queer men do before sex and simply ask your potential partners, “What are you into?” Then that would give you the opportunity to say what you are into so at the very least said partners will understand the expectations upfront. These pre-sex conversations are, naturally, guidelines that aren’t set in stone. In the moment, sex sometimes deviates from the prewritten script (I’ve lost count of the number of guys that presented themselves as tops on apps but were very not that once in bed).

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I think you might be a little too in your head about what constitutes coercion or pushiness. You are allowed to and should ask for what you want. That’s not inherently coercive. Repeatedly asking to the point of badgering, refusing to take no for an answer, and trying to manipulate someone into doing what you want—these are all things to avoid, but it sounds like you’re nowhere near doing anything like that. It’s great that you’re so considerate, but politeness is a liability when it keeps you from reasonably asking for what you want. That said, keep not calling people out for their apparent hypocrisy during sex—no one wants to hear it and the probability of you actually changing their behavior is too low to make such a confrontation worth it.

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I also don’t know if “pillow princess” is a recurring trait of similarly presenting women, and it’s dicey to draw those conclusions for sure, but you also might want to diversify your pool of potential partners just in case. I’m not saying that this issue is your fault, but you are the common denominator and so if there’s any kind of frequenting of a type with similar results going on, consider expansion.

Did you write this or another letter we answered? Tell us what happened at howtodoit@slate.com.

Dear How to Do It,

Im a middle-aged, happily married man. My wife and I have been together 17 years and dont have sex much anymore just from I think a lot of the reasons people have—kids and their demands, we dont feel great about our bodies, when shes tired Im not and vice versa, and so on. So, to satisfy my libido Ive been masturbating more recently.
Since I had my first serious girlfriend when I was 18, self-pleasure was really utilitarian—just get it out of the way so I last longer in bed, be able to focus when I get to work, etc. But the past few years, Ive really gotten to enjoy masturbating for itself and have found myself in various chat rooms with other men—many happily married too—where we talk about porn and jerking off. Over time with some regulars weve started watching porn and anonymously (but for our usernames) chatting on mic. The regulars are straight—were married, about the same age and doing it for the same reasons—but were finding we’re enjoying watching porn scenes together, I mean REALLY enjoying. Its like cheering for a favorite sports team but where your team always has a very exciting victory at the end.

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I think part of the appeal is being able to openly discuss something that has always been a thing men dont talk about and realizing others are enjoying it as much as I am. Over time, Ive found one of my “mic buds” lives close to me. He wants to get together and masturbate in person to our favorite porn. We dont want to touch each other or anything (seriously, were straight), just have a good time, and he says itll be even more fun (having done it in person before). I suspect hes right; I continue mic-ing because it is amazing to orgasm to porn with others.

So, I have a dilemma. My wife surely knows I masturbate, but not with others. I love her and would never be unfaithful. To me, masturbating and porn are just kind of a guy thing and in-person with a bud doesnt seem like much of a step. I also think itd be nice to make a new friend—as weird as it may sound to build a friendship off of porn watching. Believe it or not, we end up discussing more than just the latest AVN starlet. Thoughts?

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—Single Handedly

Dear Single Handedly,

Sorry, I might have missed it, but: Are you straight? Kidding! I get it. But look: What you describe is extremely similar to the brotherly tone that can emerge when men have sex with men. I’m not saying this to question your identity or to mock you. If anything, I related to what you wrote as someone who is interested in doing way more with guys than jerking off (seriously, I’m gay). This kind of male bonding, regardless of the stated identities of the participants, is transcendent. It’s a way of getting extremely close to someone without emotional obligation.
Mutual ease with a guy you can sometimes pull your dick out in front of yields extreme social comfort—a spa day for your soul without the facial (or with, if you so choose). I’d be not just a hypocrite but actively doing you a disservice to dissuade you from forming such a bond, because I know how special it can be.

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But, of course, there’s the small matter of doing this all behind your wife’s back, which you should not do. There’s a reason why you haven’t told her about your mic jacking, right? There’s at least a chance that she wouldn’t approve, right? Bringing your masturbrotion into the realm of IRL is presumably an even bigger offense. You say you don’t want to be unfaithful, but some might argue that you already have been—including her. Obviously, this is a thing that grew over time, but I think you’re better off explaining to her what’s going on, much as you did in your letter to us. It makes sense that you found this outlet given your circumstances. It might not be an easy conversation to have, and it may take a few conversations to really convey what’s going on, but pleasure is so much better when enjoyed honestly. A good buddy that you can show a hidden part of yourself to is a great thing to have, but so is a life partner that you can be open with. I’d start there if I were you.

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Rich

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