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,
My boyfriend and I have been having anal sex for two months. This is my first sexually fulfilling relationship and we began doing anal for his birthday. Turns out, with a good lover and lots of lube I can easily get penetrated as deep as he likes. My question is, then what? What can I do to actually make it feel wonderful for him? He already gives me multiple orgasms, I just want to return the favor.
When I ask my boyfriend what he likes, he has a hard time telling me what motions or muscle flexing would feel great to him. His natural sex style is also very low on expression until he is cumming with almost no talking, verbalization, or body language changes that I can track. The most I have gotten out of him is that when he went through his “gay experimentation” phase his favorite bottom could do some sort of anal “grip and twist” move, which he describes as feeling amazing. When I try clenching and rotating, he typically just pops out.
I have gotten good at a lot of things, including blowjobs and vaginal sex by finding the right resource to read, but Googling seems to just turn up endless articles about needing lube and being relaxed, endless lists of the same few positions, or endless books that I cannot tell if they have any actual techniques in them. We have tried doing stuff from anal porn that we thought looked hot, like holding my ankles all the way up to my head, but he just liked the visuals. I even found the memorial Facebook page for his old bottom in a vain attempt to find the magic for my boyfriend’s favorite sex move.
I get a thrill out of how excited he gets and knowing that there is something better I could be trying for him gets in my head. So asking the experts, what anal techniques do you recommend to rock his world? What web pages or books would the best place to find stuff about how to make anal feel good? Do you have any idea what I need my body to do to grip and twist with the best of them?
—Anal Bookworm Bottom
Dear Anal Bookworm Bottom,
It’s generous of you to want to make sex as good as possible for your lover. But the thing about anal is that, generally speaking, we don’t need to do anything to make it feel good. It just does. That’s the point! The butt is typically tighter than the vagina. Combine that with the thrill of taboo/transgression and it explains why so many guys are borderline obsessed with it.
I think this is why you’re coming up short when searching for techniques. It’s hard enough for people to take dicks in their butt that advanced techniques seem relatively useless. Unless your boyfriend has specifically asked for some kind of change, the fact that you’re taking his dick deep is enough. He’s orgasming from these encounters, yes? You’re doing great, sweetie.
Just to make sure, I ran your question by Tristan Taormino, who wrote The Ultimate Guide to Anal Sex for Women and wrote “The Anal Advisor” advice column in Taboo from 1999 to 2014. She knows her butt stuff. She had never heard of a grip and twist technique, but offered: “Squeezing the penis with your muscles will produce a nice sensation for him.” Try the clenching without the rotation. If you do kegels, try doing them when he’s inside you. If you don’t do kegels, maybe start? Otherwise, you could always talk to other anal enjoyers and see if there’s something they know that Tristian, I, and most of the internet don’t.
Dear How to Do It,
My partner and I have been together for nearly three years. We have a great, active sex life, and while we have been mostly monogamous, we have experimented with threesomes, playing with other couples, and he has encouraged me to have solo play dates in hopes that through having these experiences I will become open to him dating other women—his ultimate desire. However, he has now slept with a “safe” friend of ours three times over the course of the past few months, and while she is married and does not feel like a threat, I have a physiological trauma response every time they are together. I get sick to my stomach for a couple of days and feel utterly devastated. We are at a point where either I have to find a way to change how I feel about it, he has to agree to not sleep with other women, or we need to end our relationship. Neither of us want to end the relationship—we are compatible in nearly every other way—but I can’t keep going through this cycle of pain. Do you think there is a way for me to actually change how I feel about him being with other people?
—Looking for a Compromise
Dear Looking for a Compromise,
There’s no easy way to change how you feel about him being with other people. There are things you could do to try, but it’s possible you’ll never change your mind about this being uncomfortable. And that’s completely OK. Coming from where you’re at, it’s a matter of whether you can get used to it or not. At this point, signs point to no—feelings of sickness and devastation have no place in a healthy relationship. I think so far, you’ve done everything you can to be OK with him having sex with other people. You’re open and experimenting. The process of opening up is one of trial and error, and you can’t really know how you’ll feel about certain arrangements until you’re actually in them. It seems like your limit is group play—you’re receiving very clear signs from your body and mind that anything beyond it is off the table.
I really don’t think that the next step is for you to just get over this. It’s for him to understand the pain this is causing and reel it in. A quote from one of the subjects of Tristan Taormino’s Opening Up (a fabulous book about ethical non-monogamy that I think everyone interested or involved in that life should read) is my credo here: “You play to the level of the least comfortable person, if you want to keep everybody happy.” Certainly that’s not happening now.
I don’t know the particulars of these negotiations, and I don’t want to come off as judgy, but your partner has had quite a lot of sex with this woman in a short amount of time. It’s clearly too much for you, and given the newness of your openness, it’s a lot, period. You may have encouraged him to go on and have his fun, despite your reaction, but he’s done this three times and it hasn’t gotten better. He should be taking it upon himself to reel it in (or seriously consider it) just given its effect on you. I think, at best, you need more time to get comfortable here. Continuing group play may be a way to do that, but you may never get to the point where you are truly OK with him playing with and even dating other women. The best way to foster it, though, is by making sure everyone feels safe and comfortable. You can’t guarantee how you’ll feel in the future, but you can at least set yourselves up for the best case scenario. If he can’t handle this, there may indeed be a fundamental mismatch afoot, unfortunately.
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Dear How to Do It,
My husband of five years had a major mental breakdown two years ago. Therapy and medication have gotten him to a better place, but his sex drive has completely tanked and hasn’t recovered. Realistically, I don’t think we’ll get back to daily intimacy. Twice a month just isn’t enough for me, though. We’ve had conversations about this off and on but haven’t been able to find a solution that works for both of us. How can we work through this?
—This Is Frustrating
Dear This Is Frustrating,
You’re not giving me a lot here, so I’m going to approach this broadly. The best place to start is probably going to talk this out with a therapist or counselor in the hopes that a disinterested third party can help you sort yourselves out. His prescribing doctor could add bupropion (Wellbutrin) to his cocktail to see if it helps increase his libido. You could talk about alternate ways of having sex (for example, exploring kinks and using toys) that may make things more stimulating. You can read books like Esther Perel’s Mating in Captivity and Emily Nagoski’s Come Together: The Science (and Art!) of Creating Lasting Sexual Connections, which may provide new ideas for eroticizing a long-term relationship. You can talk about opening things up to whatever degree—the most straightforward answer would be for you to be allowed to pursue the sex you want, alleviating his responsibility somewhat.
If none of these work, and you can’t agree on a solution, you must make your choice: A husband that you (presumably) love but don’t have sex with as often as you like, or a completely uncertain future without him, which may offer more sex but certainly doesn’t guarantee it. Working through it can be hard. Working through it can be hard, but only you can determine whether that’s worth doing.
Dear How to Do It,
My partner and I are polyamorous and have a few other serious partners each. We’ve been together for four years and have long operated on a set schedule (we see each other once a week, usually on Tuesdays, but occasionally on weekends, all set up on a recurring schedule that my partner created himself). I went along with this for years, the reliability was nice, and honestly, we had a bit of a chasing dynamic where I wanted more of him than he was willing to give, so I just took whatever he would give me. Over time though, a lot of aspects of the set schedule didn’t work for me. For example, I don’t schedule that way with anyone else, so it in effect gave this partner first dibs on my time as he wanted it. We also do not see eye to eye on how far in advance it is acceptable to cancel or reschedule a date if needed etc., so I often felt hurt when things were altered last minute. I had been dwelling on this idea for a long time, but finally brought him my decision to stop using this schedule. Instead, I would like to schedule as I do with everyone else: We discuss our availability, usually a week in advance but sometimes more, and find times that work. I made clear that I had no intention of seeing him less, once a week still sounded great, and I added in a lot of reassurance about how much he still means to me as a member of my chosen family, and I am not going anywhere.
However, in the fallout since I announced this decision, it has been made clear both from him and from one of our mutuals that he sees this as a pretty serious de-escalation in my commitment to the relationship. I am just not sure how to navigate this. I know I cannot make him see it my way of course, but I do not use a set schedule with anyone at all, and I am still very committed to all of my relationships. How do I navigate us having two different ideas of what constitutes serious commitment to the relationship?
—Don’t Set It and Forget It
Dear Don’t Set It and Forget It,
For whatever reason, your set Tuesdays were important to your partner. I am obviously not inside of his head, but I do wonder if having a set day to see you every week worked as a tangible symbol of your commitment. You’re both practicing polyamory, which means your lives lack many of the cultural hallmarks of commitment that we’re spoonfed. Operating completely outside of mononormativity is exciting and means you get to map out your own life, but it can be intimidating. I interpret his desire to keep a schedule as a small thing he favors for the sake of reassurance. As long as you two have Tuesdays, you have each other—or something like that.
Now, I don’t think you’re unreasonable for not wanting to stick to such a strict schedule. Stuff comes up from week to week. But look at your wording: “I don’t schedule that way with anyone else, so it in effect gave this partner first dibs on my time as he wanted it.” I think maybe part of the issue here is that he wants to have first dibs. I’m not sure where you are in terms of hierarchy, but you refer to him repeatedly as your partner. You may use the same word for other people you’re in relationships with, but if the guy you wrote in about is your primary or something like it, well, it makes sense that he’s bristling that you’re refusing to make the exception for him, as his status is supposed to be exceptional in your life.
If, however, you are nonhierarchical, well, isn’t it telling that he might want to be special anyway? The tables have turned, it would seem—you wanted more than he was willing to give previously, and now he’s asking more of you than you’re giving. Perhaps the shift in parity is what he finds galling, which would be awfully self-entitled of him.
This is largely speculation. Practically speaking, I think you should stick to your guns. See him on the schedule you prefer and set that schedule at your pace. Show him that it doesn’t mean you’re less committed to him, that you’re not de-escalating, but that you’re just trying to organize your life differently. This may just take some getting used to and once he realizes that the change is virtually cosmetic, he’ll stop complaining to you and others. If you’re so concerned about his feelings, think of other ways you can externalize your commitment–tickets to a show that you both may like, some kind of gift, cooking him dinner. Whatever. Go out of your way to prove to him that moving your schedule around isn’t personal. Or let him suffer a little bit and just deal with your decision. You have a bit of power as a result of this change, and you shouldn’t feel bad about that.
—Rich
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My wife recently came out as bisexual, and I’m so happy for her. It’s truly beautiful to witness the evolution of her sexuality, but there’s one thing that’s giving me pause: She wants me to have a threesome with her and another women. For a variety of reasons, I really do not want to do this. I want her to experiment with women on her own. In return, she says I’m “not a real man” because “real men” would jump at the opportunity to have a threesome with two women. It’s really getting to me. What should I do?