How to Do It

My Careful Plan to Please My Partner Just Went Horribly Wrong

This seemed like the solution to everything.

A male and female couple seem to be in an argument with a neon X between them.
Photo illustration by Slate. Photo by Alexis84/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 am a 32-year-old cisgender woman on the autism spectrum. I am also asexual. I’m living with an allosexual cisgender man, and I quite like him. However, sexual intercourse between us gets awkward, for lack of a better term. I’m happy to put out to please him, but something is lacking in our sex life, and he seems frustrated by his inability to bring me to orgasm.

Advertisement

I decided to open up our relationship, and after looking through his porn history to establish his physical preferences, went looking for a local woman who might be interested in a hookup with him. It took some time, but I eventually found “Stella” who seemed interested in the idea, especially if I could watch her.

Advertisement
Advertisement
Advertisement

We came home to my boyfriend last evening, and he was very agitated and unwilling to have sex with her, even with our joint urging. The evening ended badly, and Stella was quite upset with me for leading her on. I’m not sure what went wrong or how to do better next time. Can you help?

— Hopelessly Confused

Dear Hopelessly Confused,

It seems clear to me that your heart is in the right place, and that you just wanted to do something nice for your partner, but all of this stuff should have been done with his full consent. The main problem here is that you coordinated sex for him without consulting him first. Then, you sprung it on him in front of a stranger, and he may have felt embarrassed or some performance anxiety. Or maybe, despite your ostensible understanding of his type, he just wasn’t into Stella—I mean, even professional matchmakers don’t bat a thousand. Educated guesswork is still guesswork. Finding a third is a job best done together, unless the surprise element has been previously negotiated (in another scenario, what you did might be a turn-on). He should have a say in choosing his partner.

Advertisement
Advertisement
Advertisement

What you did was a lower stakes version of buying someone a puppy without asking first if they even wanted one or have the bandwidth to take care of one. Sometimes the reality of your gesture outweighs the kindness behind it, and you create a burden out of the goodness of your heart. I have a less rosy view of you rifling through his porn history, which also sounds like you may have done without consulting him first. People feel very private about these sorts of things, and they, too, require conversations ahead of time.

As for his frustration, you shouldn’t worry about him so much–how he feels about not being able to assist in your orgasms matters far less than how you feel about it. For now, focus on the fact that any change in the relationship needs to be taken on together.

Advertisement
Advertisement
Advertisement

Dear How to Do It,

I am a transmasculine person who began hormone replacement therapy around six months ago. Almost everything about being on testosterone has been great. As predicted, my sex drive has increased quite a bit, which has mostly been fine. I live with my two partners, and I feel sexually fulfilled by our relationship (and to my knowledge they both feel the same way). The problem is, with the combination of my sex drive and logistics, I simply cannot find the time to masturbate enough to satisfy myself!

Advertisement
Advertisement

Since there are three of us and I work the most hours, I rarely have time alone in our room.
And when I do have time alone, I feel like I have to spend all of my time masturbating, when there are many other activities that I would love to do alone if I had the time. I have a really hard time coming in any position other than laying down straight on my stomach or back, so I pretty much have to be in bed if I want to get off. Ill occasionally try to get myself off when one of my partners is home and doing something else in another room, but more often than not, I just rile myself up and cant actually get off in time, and thats worse than not masturbating at all. At night I sleep between my two partners, so its not like I can roll over and masturbate once they fall asleep. We have other folks living in the house as well, and every room besides our bedroom is a common area, so I cant go into another room to masturbate. I enjoy the sex I have with my partners, but even if we had the time, I dont think having more partnered sex would fix my problem. I think if I had partnered sex every day, I would still want to masturbate in addition to that.

Advertisement
Advertisement
Advertisement
Advertisement

Before testosterone, I identified as a stone butch. I rarely masturbated and almost never received touch during sex. Because of this history, I find it really hard to communicate with my partners about my sex drive. I have worked up to being more comfortable being touched during sex, but talking about masturbation feels like a whole different ballgame. Im not necessarily lying to them about it—Ive insinuated a few times that I have been exploring what kind of touch feels good on my body, etc. But at the same time, I dont think my partners know how often I would like to masturbate or that I do it every chance I get. I know the solution is to ask for more space, but it makes me feel SO weird and dysphoric to think of asking for space specifically to touch myself. It makes my skin crawl to think that my partners would ever think about me masturbating. At the same time, I know something needs to change, because its killing me! Im as horny as a teenage boy but have no space to relieve the tension.
What should I do?

Advertisement

—Time to Myself

Dear Time to Myself,

Advertisement
Advertisement

What I’m about to advise jumped out as obvious to me, which means you probably have considered it, but since you didn’t mention it and part of my job is to think for you, here you go: Try the bathtub, if you have one. It may give you enough uninterrupted time, and it wouldn’t upset the precarious balance you’re striking. But I would think of this strategy as a stopgap as you work up the nerve to have more direct (and needed) conversations. Life is much easier when you don’t have to sneak around to jerk off, which can reaffirm the shame people already have about masturbating. Being able to rub one out on your terms is part of growing up.

Advertisement
Advertisement
Advertisement

You can ask for alone time in your room without specifying why—the need for this kind of space is common, and your request shouldn’t come off as outlandish. Let your partners work it out for themselves why you want it. If you’re asked point blank, you can dodge the question, or maybe you’ll find the conversation is easier to have when someone else starts it. It seems very clear that in addition to your bodily transition, your sexuality is going through a metamorphosis as well. You’re more comfortable now touching yourself and having others touch you. Think back to when you broke through in those areas—you probably had similar anxiety about doing so, but somehow you found it in yourself to push out of your comfort zone and ultimately expand it. I think you’ll find there’s a similar process happening here. This stuff is going to be daunting and stir up feelings of shame as you approach it, but once you do, in all likelihood you’ll be glad.
Becoming more communicative with your partners is only going to be a good thing for everyone in the long run. The reason you have arrived at this current challenge is because you and your body are ready to overcome it. You can do it.

Advertisement

Help us keep giving the advice you crave every week. Sign up for Slate Plus now.

Dear How to Do It,

I’m a dominant with a very deep voice and an extremely overpowering vibe. I’ve scared submissives stiff while standing still after barely saying a word, repeatedly. How do I make my subs more comfortable engaging with me IRL? I don’t get why this is happening. I’m not massively muscular or anything (though I am constantly told that I look like Clark Kent/Superman).

Advertisement

— Simultaneously Very Successful and Very Frustrated

Dear Frustrated,

Lighten up. Smile more. Soften your X-ray gaze. Be friendly. Give answers that are longer than one word. You can neutralize your intimidating appearance by being approachable and personable in your affect. This may fly in the face of how you think you should carry yourself as a dom, but making your subs comfortable is an effective way to retain control, thereby ensuring that everyone gets what they want. If you continue to project stoicism, you’ll have fewer options. You can hold onto your social profile, or stop scaring people, but it seems clear that you can’t have both.

Advertisement

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

Advertisement
Advertisement

Dear How to Do It,

My partner and I have been discussing opening our relationship of eight years. We were briefly nonmonogomous for a short period early in our relationship, and about a year ago, we started having conversations about exploring this again. While we haven’t pursued anyone in that time, we’ve worked on establishing our boundaries and how to do this in a way that works for us. The conversation is ongoing and the door is open should either one of us begin to develop feelings for someone. Enter my friend, “Becca.”

Around the same time these conversations with my partner began, Becca and I met through work and hit it off (in a platonic way) almost immediately. We have become close and have built a solid friendship outside of our jobs. I really value this friendship, and could see it lasting a long time. Becca and her long-distance partner have also recently decided to explore nonmonogamy. This is new to them both and has been on the table for a while, but they have yet to pursue outside hookups. She and I have been the occasional sounding board for one another as we’ve each started navigating these new waters. We and our partners have all spent time together and get along well. Maybe you see where I’m going with this.

Advertisement
Advertisement
Advertisement

Becca has a flirtatious personality, and is very physically and verbally affectionate with the people in her life. She’s said several times she has a “crush” on me, but in a playful / jokey / almost child-like way that for some reason feels more platonic to me than sexual or romantic. I think I’ve gotten the inkling of *vibes* a few times, and I’ve tried to casually drop a couple of hints, but I’ve been in a monogamous heterosexual relationship for so long that I have no idea if I’m going about this the right way. I’m definitely attracted to her, and the idea of easing into nonmonogamy with a trusted friend who has a primary partner and is also just starting to explore is appealing. I’ve been honest with my partner about these feelings; he’s supportive and letting me take the lead (if there’s anywhere to lead this, that is).

Advertisement

So. Do I bring this up with her? Is it even a good idea to pursue someone I’m close with, who is also so new to this? Do I just wait it out and if it fizzles, it fizzles? Since I started having these thoughts, I’ve chosen to let things play out naturally, but I guess at some point I need to either say something or decide to let this go. As her friend, I do not want to make her uncomfortable, especially because we work together often. I’m nervous about my feelings being reciprocated. I don’t want to make assumptions or romanticize this just because she is incredibly charismatic and her relationship is open. However, I sometimes struggle with vulnerability, and there is a part of me that feels like maybe I’m letting my insecurities get to me so I can avoid the risk of being rejected.

Advertisement
Advertisement
Advertisement
Advertisement

Am I psyching myself out before I’ve begun? Help!

—Chronic Overthinker

Dear Chronic Overthinker,

To answer your last question: You might be. Becca told you she has a crush on you. Despite the vibes, you’ve decided to interpret that as feeling “more platonic to me than sexual or romantic.” That’s coming from you and it’s telling that you can’t even put your finger on why. What’s coming from her is that she’s saying she has a crush on you! Try operating by taking that at face value and see where things go. Next time she says it, tell her that the feeling is mutual. See what happens. If she doesn’t end up saying it within the next few times you hang out, figure out a way to match her overtness. You could literally just tell her you have a crush on her, referencing the past few times she’s mentioned it.

Advertisement

I usually warn people away from hooking up with coworkers, though clearly it’s a common occurrence that owes as much to proximity as anything. This case, I think, doesn’t call for the typical caution, since you work together “often” but not always. Plus, it’s just all too perfect. How could you not seize this opportunity and experiment with someone who’s going through practically the same thing? Fear of rejection is always going to be there, but if you let it control you, you’re basically choosing the path of rejection. Why aren’t you shaking in your boots from that?

Advertisement

This will get a lot easier as you accrue experience. You’re going to have to take the leap sometime, and Becca seems like the perfect person to be holding hands with when you do. Make this happen.

Advertisement
Advertisement

Rich

More Advice From Slate

I grew up in a home open-minded about sex, as opposed to my husband, who grew up very Christian and conservative. I was his first and only sexual experience until recently. I gave him a “hall pass” so he could experience human sexuality without the cloud of shame he was brought up with. He’s had a few really good experiences and recently not so great ones. Basically, he’s experiencing the highs and lows everyone goes through in their teens and 20s, but in his mid-40s. Then I asked to venture out myself because … hey, it’s fun! He flipped out on me.

Advertisement