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 27-year-old woman married for two years, and from the beginning, we decided we would each be free to have other sex partners. Recently I have been involved with a neighbor, while right now my husband is not involved with anyone else. My husband suggested a threesome, which I declined. He then made the suggestion to my lover, who not only was enthusiastic but suggested they include his wife also. I’m not at all interested in his wife, but if I were, I would approach her myself and suggest a one-on-one encounter. I think sex is a personal, intimate experience, not a group activity. But they all are pressuring me and are angry that I won’t go along, which I don’t get because the three of them are free to have group sex if they want. In my mind, sexual freedom means not feeling bound by social conventions and making our own rules—but those rules should respect our partners’ boundaries. If I suggested a particular position or act or toy that my partner wasn’t into, I would accept that response and move on to one of the thousand other ways to enjoy sex. I think it was wrong for my husband to approach my lover after I said no, and it’s wrong of them all to be mad at me. I don’t really care about my relationship with my neighbors, but I don’t want to ruin my relationship with my husband. Is there any way to fix this without doing something I don’t want to do?
—Girl Next Door
Dear Girl Next Door,
I was immediately concerned by the fact that you’re having a sexual relationship with a neighbor. As convenient as that may be, if things get awkward, they’re awkward right outside your front door. I was very concerned that your partners and the neighbor’s wife are pressuring you to have sex under conditions you aren’t into, and I’m extremely worried that they’re angry with you for this preference.
Have a conversation with your husband, letting him know you’re not OK and that you need to talk to all three of them as a group. Set your boundaries, and set them hard. Prepare what you’ll say beforehand. Don’t leave room for argument. Make it very clear that sex is a two-person or solo activity for you, and you aren’t interested—nor are you likely to ever be interested—in a group interaction. Tell these three people it’s inappropriate to pressure you and that you’ll remove yourself from the situation or sever ties if you need to. Make sure you mean that last part. Then give them a chance to show you that they can treat you well and be upstanding sexual citizens. If they can’t, remove them from your life.
Hopefully your husband backs off, but if he doesn’t, your relationship might be strained. That won’t be your fault. Stick to your boundaries and think about leaving if he doubles down or escalates things.
Dear How to Do It,
I’m a lesbian who has been with my fiancée for 10 years. My partner wants to explore role-playing cucking with me. I am not comfortable bringing another person into the fold, but I am intrigued by cucking role-play. The thing is, I don’t know how to begin with this! It’s very new to me, but at the same time, it sounds really hot. I’m kind of coming up short in finding how I can actually achieve this, though, so I was wondering if you had any pointers as to how I could effectively role-play this scenario with my partner.
Dear Aspiring Cuck,
To the internet! Search for cuckolding videos, lifestyle blogs, and erotic stories. Pay attention to what gets your libido going and what feels interesting to you. Make a list. Share the list with your partner, and highlight a few things that seem like fun.
Now, to the bedroom! Or the couch. Or the kitchen counter. Wherever works for you two. Have fun with it.
Dear How to Do It,
I realize that this is a column for sex advice, but my question has more to do with how to not have sex (sort of). How do I tell people that I’m not looking for a casual relationship? I am a bisexual woman in my early 20s, and I’m on the asexuality spectrum. Because of this, I usually need to form an emotional connection to someone before I get sexually attracted to them. I can appreciate if someone is attractive, but I tend to feel emotional attraction to people, not sexual attraction. In the age of dating apps and casual flings, this has proven problematic because I don’t know how to specify that I am not looking for something casual but instead something with serious emotional connection.
I’ve used dating apps, and I’ve dated in real life, but with both, inevitably, the other person hasn’t been looking for something serious, only for a hookup or a sexual relationship. I’ve given both a try in the past, and the results have been … unsatisfying. Casual relationships leave me feeling dirty in my own body because I inevitably end up faking it and don’t yet feel attracted to the person I’m with. I’ve also tried asking out people with whom I have a preexisting emotional connection and whom I’m starting to feel a little attracted to, and the answer is inevitably, “I’d rather stay friends.” How do people do it? How do I find an emotional relationship in the time of internet dating and sexy profile pictures that I’m inevitably not attracted to? How should I specify that I’m looking for a soulful connection—something serious, not a fling? And how do I tell people whom I’m interested in that I can only do serious relationships and I don’t yet feel sexually attracted to them but emotional attraction instead?
—Get to Know Me
On the apps, you can absolutely specify what you’re looking for. People do it when they’re searching for hookups, and they do it when they’re looking for something long term—“someone to delete this app with”—and you can do it with something like “graysexual and looking for connection” in your profile or “I need to date for a couple of months before I feel sexual” in one of your first few messages.
Think about the sites you’re using, too. Go more for OKCupid than Tinder. Maybe even Match.com. Places where people are more focused on relationships. You also might start frequenting online spaces where other asexual people hang out, like message boards or forums, and forming platonic relationships there. Find out where your new friends have met people, and maybe find someone of romantic interest.
Once COVID clears up, you can also meet people out in the world. Go to places where people are mingling, enjoy hobbies with a social aspect, and take opportunities to meet friends of friends. Then take things at your own speed.
It might take you longer than you’d like to find a partner. That’s partially because of the specificity of what you’re looking for, but it’s also partially just dating. Try to keep that in mind—dating is a process of sorting through people, some of whom are great, until we find one who matches in a significant way.
Dear How to Do It,
My wife and I will be together 30 years, having married for 25. We met and started dating as teenagers. I’m 47 and she’s 48. We had great sex, several times a week, until I had a back injury. Many surgeries later left me with erectile dysfunction. I tried pills of every type and nothing worked. However, I knew she needed a release, so I used other ways of making love to her. Hands, fingers, mouth, kissing, hugging, cuddling, toys—you name it. As much as she needed it, I did my part, even though I could not get erect. I know she missed that penetration intimacy, but that’s something I couldn’t give her.
Fast forward a few years: My doctor put me on penis injections, and they have worked great. Hurts like hell, but it works. And it’s worth it. I’ve been able to become erect and have regular sex along with the other methods we perfected, and I always make sure she has as many orgasms as she wants before we finish. If she wants them. I, on the other hand, cannot orgasm at all through penetration. If I masturbate long enough and hard enough eventually I can orgasm, but I have one maybe one time a month if I’m lucky. She used to initiate sex often, but since my issues started, she does not. At all. When I ask she says she doesn’t because I take too long. I can stay erect and we have gone at it for two, sometimes three solid hours, and although we enjoy it, I cannot have an orgasm. But whenever I do, then we thoroughly enjoy being together. She says she just gets tired and wants to be done. She also says she doesn’t want to initiate because it’s not fair to me that she can have up to a dozen orgasms and I get nothing. But I’m good with it because we’re intimate and I feel making up for lost time.
I should mention we have been very happy together, and neither of us wants anyone else. We’ve ever had any marital issues at all. We are still very much in love with each other. So I guess my questions are: How do I get her to start initiating sex again? What can I do to have an orgasm again and shorten our sex? She’s even told me many times she misses the fact that we can no longer have a five-minute quickie like we used to. But much has changed. I’ve talked with my doctor and he has nothing to help with the orgasms. I hope this all makes sense and you can offer some help.
Dear Finish Line,
I’m immediately empathizing with your wife. There’s something really awesome about extracting semen from a pair of testicles through vigorous application of pleasure. It feels powerful. Delightful. Rewarding. Ask her if she’s had a similar experience. If so, you might try to find significant ways for your wife to help with your monthly ejaculation exclamation point. If not, don’t worry about it.
You might want to try another specialist, if you’re able, to consider medical options. At home, have you tried prostate massage? You’ll want to gently slide one well-lubricated-but-not-dripping finger into your butt and feel around, towards the root of your penis, for a more firm spot. Gentle pressure and small strokes should help you figure out what feels good. Might be something there for you.
As for quickies, can you make it a game of seeing how fast you can get her off and then moving on with your day? It isn’t the same as both of you coming together, but it could still be fun. Remind her how much pleasure you get from getting her off.
If you want her to initiate, that means giving her space to do so, even if it takes several weeks. She might feel worn out. She might be starting the process of menopause, which changes sexual appetite and response, and thus may be less interested in sex. Surely in 30 years of being together you’ve worked out how to have a productive conversation about something difficult. Put those skills to work and talk through what’s going on. Once you know the whys of the situation, you can start figuring out the what-to-dos.
More How to Do It
A man who took nude pictures of me without my consent in my home without my knowledge recently got married. He was convicted of multiple offenses related to my case. In the process of a plea deal, they dropped enough charges so he wouldn’t be on the sex offender registry. He is a bad person and probably has pictures of his wife too. Is there any way to let her know?