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’m a 40-year-old guy who’s been reading a lot about sex in the last year trying to become more sex positive and also improve my sex life. I’ve been married for 13 years to an amazing woman. I saw a phrase in a book this week and I had a huge “aha” moment: She’s a pillow princess. I say this with gentleness and affection, but it so totally describes her. Funny thing is, she has a higher sex drive than me and has no problem initiating sex, but once we start foreplay (which I enjoy), the focus really is on her. Pretty much exclusively. I like long sessions of lovemaking. I like long periods of foreplay and I’m wired to enjoy giving. However, she just … lays there. And then after she’s had an orgasm—or seven—she just lays there for me to finish.
I’ve become sort of numb to this and just accept this is how it is. I don’t mind this, and most of the time enjoy it. But as I’ve worked on myself and educating myself, I know that it’s OK and healthy for me to speak up. I just don’t know how. I’ve tried asking in the past for a night focused on me. It doesn’t happen. I’ve asked for a night when I get to come first (with toys handy for her and me to play with after!). Nope. I’ve asked to see what it’s like to have a blow job first and then a recovery period and then a round two. She hates blow jobs, so this is off the table. I’m trying to be confident and vulnerable about what I want. I also know just because I want something doesn’t mean I get it. Welcome to being vulnerable and intimate. So what I’m left with is a pillow princess who I love and enjoy loving on. I just want to have some sex I want to have some of the time. How can I make that happen?
—Pillow Prince
Dear Pillow Prince,
I think you should start with an intelligence-gathering conversation. Inquire into where your wife’s pillow princessdom is coming from. For instance, I hated being on top during sex from about 21 to 33 because I had undiagnosed, and therefore untreated, arthritis. And untreated tooth grinding prevented me from enjoying giving oral sex on men for the amount of time most require to orgasm. What I’m saying is that it’s possible your wife may be navigating a physical issue, and if that’s the case, it might be treatable. If not, well, at least we’ve ruled that out. Come from a place of curiosity when you have that conversation.
Since your wife isn’t into blow jobs, I’m wondering about other options. How are you with digital sex? As in with one’s digits. Can you orgasm from and enjoy a hand job? If so, you might investigate that option. If hand jobs don’t work for you, you might suggest trying a textured sleeve toy. The sleeve can be removed from any casing and squeezed with the hand for added stimulation.
I sense a little uncertainty in your letter. In two paragraphs, you say that you enjoy your wife simply lying there and also that you just want to have some sex you want to have. These statements are at odds with each other. I encourage you to think through what’s going on with your desires and do some introspection about this contradiction. You’ll be better able to communicate what you actually want if you have a better grasp on what that is. Do you crave variety? Do you want to be the center of attention sometimes? Do you want to feel active participation from your wife? Whatever it is, name it, sit with it for a few days, try to understand why, and get ready to communicate all of that.
You’ve been married for 13 years, so I assume you can tell when your wife is in a good place to handle a serious talk. Remember the basics—make sure everyone is calm, hasn’t missed a meal, has had enough sleep the night before, and has time to really dig into the subject.
Decide whether a broadening of the sex you two have is a requirement, and think about whether you’d want to divorce if things don’t change. If divorce is on the table, communicate that as gently as possible. If it isn’t, you may have to figure out a way to be happy with what your wife is willing to do.
Dear How to Do It,
I have been with my wonderful boyfriend for two years now. He is kind, gorgeous, smart, and fun—literally everything I’ve ever looked for, and I can’t imagine life without him. However, he was raised in an extremely conservative religious environment where sexual thoughts were completely off the table, and sexual expression has always felt a little unnatural between us. He has always attributed it to his upbringing and slowly started to open up, but he told me last week that he thinks it runs deeper. He doesn’t feel a sexual drive toward me at all, even though he loves me and wants to be with me forever. He had assumed attraction would grow over time, but he feels basically the same as he did when we started dating. I feel completely at a loss: I can’t imagine breaking up, but I also am not at all sure what a relationship looks like when attraction is one-way. He is still willing to do anything I want for my sake, but I feel so overanalytical now that I know the feelings aren’t reciprocal. Polyamory is not something either of us want. Are we doomed or could this work?
—Unorganized Religion
Dear Unorganized Religion,
I wish I knew what age bracket your boyfriend is in. If he’s in his 20s, I think it’s reasonable to give him some more time to sort through what’s going on and who he is outside of the extremely conservative religion. If he’s in his 30s, I think it’s reasonable to encourage him to see a professional therapist to talk through his past and how it might be affecting him today.
Either way, he may never feel a sexual desire toward you. You have to decide for yourself if you’re willing to be in a monogamous relationship where your desires are catered to at best. Think about how important sex is to you. Think about how often you like to have sex, whether that sex needs to be partnered, and what kinds of sex you enjoy most. Spend some time imagining life without sex.
If you have a very low sex drive, or are perfectly happy masturbating for the rest of your life, I can see this working. If you need partnered involvement to enjoy sex, and enthusiastic consent matters to you, I don’t see this working long term. You also might give it another year or so to see if your boyfriend develops more clarity about his relationship to sex. At the end of the day, it’s your choice, and you can always choose to leave the relationship later down the line.
Dear How to Do It,
My almost-18-year-old trans son and I have pretty good communication about sex. He takes an SSRI for anxiety and recently upped his dosage. He casually mentioned that he is noticing a dip in libido and that it takes “two hours” of masturbating to orgasm. I asked if he had told his psychiatrist, and he said no, because “it’s not that important.” He will go on T in a few months and probably that will up his libido, but I don’t know how it affects orgasm. I did buy him a small vibrator a few years ago, at his request, but I don’t know if he uses it. I have a magic wand and wonder if something that powerful would help—but I’m not going to lend him mine to try it. Also, sometimes I feel sore or numb after just using it for less than 10 minutes (granted, I’m post-menopausal), and if it really is taking him a super long time to get off, I don’t want him to injure himself. I will encourage him to talk to his psychiatrist, just so she knows what’s up, but not expecting any solutions since the increased dosage is helping a lot with his mental health. Should I ask if he wants a more powerful toy? Just let him figure it out or see if he asks? Any other helpful tips for a person on SSRIs? I want to keep communication open and not be intrusive, but it sounds pretty unpleasant to have so much difficulty with orgasm. Thanks.
—Boundaries
Dear Boundaries,
Your son is about to be 18. I think the most involvement that’s appropriate at this stage is for you to encourage him to tell his psychiatrist about any and all side effects, as you’ve done. That’s an important life thing—if the doctor doesn’t know what’s going on, she can’t help. And things that we patients think are unimportant sometimes turn out to be very relevant. There could be another medication worth trying, even if this one is working very well. Or cognitive behavioral therapy skills for anxiety management could be an option.
He might not care about sex at this stage. Sometimes big life stuff is more important than, well, other big life stuff. He might be focused more on his transition and his schoolwork, and that would be completely understandable. He may feel that the dampening of sexual response is worth the relief he feels from his anxiety.
Vibrators may not be the appropriate toy for your son, either. Buck Angel has a line of sex toys for trans men that might be worth looking into. And with enough imagination, the clit-sucking toys like the Womanizer can feel like you’re getting a tiny blow job. Again, at most, I’d print out a flyer and leave it on his desk or something. If he comes to you with a request, that’s an entirely different situation, and in that case, I’d encourage you to support his choice by having the conversation he wants to have, and buying the sexual implement he’s interested in.
You sound like an awesome, supportive mom, and I love that you’re cautious of being intrusive. Let him lead the discussion at his own speed, and good luck.
Dear How to Do It,
At 25, I find myself newly out of a four-year relationship with a genuinely wonderful guy (“David”). I’m very sad and I miss him, but I’m also starting to wonder about “getting back out there.” My problem is that I don’t know how to have casual sex—I’ve only slept with two guys, and haven’t been single for more than three months since I was 19. My first relationship was emotionally, verbally, and sexually abusive, leaving me with PTSD. David and I knew each other casually before we started seeing each other, and he was really understanding about my trauma and always made me comfortable. Now, I really don’t want to rush into another relationship, but I miss sex—I’m a very sex-positive (and kink-positive) person and have quite a high libido—but in reality the dating-app encounters that I love to live vicariously through my friends would be triggering for me. I feel like I can only hook up with someone I know and like enough to feel comfortable with, but then how do I avoid catching feelings and falling into another relationship? Am I doomed to be a serial monogamist?
—Heartbroken and Horny
Dear HH,
First, I’m sorry you lived through that first relationship. PTSD is terrible. I’m heartened to hear that you were able to connect with David, and pleased that you’re taking your emotional safety into account when you’re thinking about dating.
Having feelings, and letting our feelings dictate our behavior and life choices, are two different things. Feelings are going to happen. You can’t spend an extended period of time rolling around in bed with someone you like and respect and not have some kind of feelings toward them. Warmth, appreciation, and even love can happen. None of these feelings mean you have to be dating, much less monogamously committed to each other. If you have sex start feeling all gooey in the heart, you have a choice to make—you can absolutely ask your partner if they’d like to escalate the relationship, or you can take a breather and remind yourself that you don’t want to jump into another “relationship.” I use quotes because even an anonymous hookup is still some kind of relationship. You might also see more than one person at a time if that feels OK for you.
If the feelings you’re worried about are jealousy, when that begins, remind yourself that you don’t want to be paired off right now. Look at where the jealousy is coming from. Are you stuck in a script where two people who like each other must pair off and be exclusive? If so, interrogate that. If there’s a need to control, work on learning how to accept a little bit of chaos and uncertainty. And if you’re dealing with insecurity, do the work to overcome it.
Be transparent with your partners about what you want, and let them know if that changes. Give them the same respect and esteem you would give them if you were officially paired off in the traditional couple form. And communicate your feelings as you feel comfortable. One of my best friends started off as a friends-with-benefits situation, and another close friend is someone I monogamishly dated for a year. I’m glad I had feelings about these people, and I’m thrilled that we’ve been able to transition our relationships as needed. Good luck.
—Stoya
More How to Do It
I am a 30-year-old single man. My best friend since I was a young kid and his fiancée have been my two closest friends for the last decade. A little less than a year ago, after some drinks, the three of us had sex. They remain my best friends, but we now see each other several times a month and have a threesome about once a month. Despite my initial concerns, the relationship really hasn’t changed that much. Well, she’s now pregnant with their first child, about two months in, and I’m worried.
