How to Do It

My Boyfriend Keeps “Pushing It” With Me in the Most Frustrating Way

I’d really like this little game to stop.

A man looks surprised next to an illustrated door with movement lines.
Photo illustration by Slate. Photo by AaronAmat/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’m in a (sort of) newly open relationship. My partner came into this with some bad habits around mildly pushing my boundaries in ways that can be a breach of trust. In the most egregious cases, he did things like unexpectedly bringing one of his other partners along on our date or signing me up for a threesome without first finding out if I was down, leaving me in a super awkward position. We’ve talked about those things and he doesn’t do stuff that bad anymore, but he still doesn’t always respect my request to be told before he makes plans to sleep with someone else. He’ll still tell me before it happens, but the plan will already be in place and usually, he’s just about to walk out the door, so it still catches me off guard.

Advertisement
Advertisement
Advertisement
Advertisement

Practically, this isn’t a super important detail—I wouldn’t want to veto, I just want that extra sense of feeling prioritized before he makes his plans. I don’t think he gets that this is a big deal to me. My question is, now that this is a recurring problem where he’s disregarded my request more than once (albeit apologized after), how do I make it clear that this really needs to stop? I feel like I’ve read so much contradictory ethical nonmonogamy advice that I don’t trust my instincts at all and am worried it would be manipulative to act on them (like, if I were to veto his plans whenever he does that—which I’ve heard is super toxic to do). I’m not even sure my request was a reasonable one in the first place, but I don’t feel like rewarding him for disregarding it by removing it. How can I get across what I need here, and make it clear this is actually really important for me?

Advertisement
Advertisement

— Stop Pushing It

Dear Stop Pushing It,

Boundaries are what make otherwise untenable situations tenable. Your request to be given a heads-up with lead time is reasonable because it is what you feel you need. We aren’t in the realm of objective facts here—every open relationship forms as it goes. It’s a continual process of checking in with yourself and each other. It breaks my heart that you’re questioning yourself so ardently. Your needs aren’t the problem here; your partner’s refusal to honor them is.

Advertisement

I believe that apologies are worth very little when they aren’t backed by effort to avoid the same situation again. Your partner has already shown you in many ways that he has a selfish and disrespectful streak. His refusal to give you a heads-up with sufficient lead time is causing you unnecessary grief. If he wants to be in an open relationship with you, he has to respect this or there will be hurt feelings and possible conflict. Can you cast things in these terms for him? Something like: “Either we respect each other’s boundaries, or we can’t have an open relationship/relationship at all.” Generally speaking, I’d think your impulse to roll with the punches and forgive is a good strategy. If it happened once or twice that he set up a hook-up with a really tight turnaround, that would probably be worth forgiving and forgetting. Right now, he’s continuing a long-running pattern of disregarding your requests and boundaries. I have to wonder if transgressing is part of the fun for him. If it is, he’s exploiting your sensitivities. At minimum, you can expect more grief. Without an acknowledgement from him that he’s in the wrong and a protracted effort to do better, that grief may come to define your relationship. Don’t let it get to that.

Advertisement
Advertisement
Advertisement
Advertisement

Dear How to Do It, 

My boyfriend and I have been long-distance dating for almost a year. Im in my mid-30s, and for all of my 20s, I was almost exclusively a bottom. Over the past two years, Ive loved exploring my top side and would now identify as primarily top: I now prefer to bottom only in cases where I feel a genuine romantic connection with someone.

He is primarily a bottom, and we are open. While I think Im doing pretty good at managing being open, theres one part thats sticking in my mind a bit weird: He occasionally (about once every month or two, by my estimation) tops other people, but has yet to top me. A few months ago, I made it known that Id like to bottom for him sometime soon, as I feel the connection I want with him. Hes never explicitly said hell never top me, he’s said I have a cute butt (for what that’s worth), and hes described to me the guys he likes to top and I feel like I fit the bill. But Ive brought it up about 3-to-4 times now, and theres always a yes, we’ll get to it” usually followed by some hesitance. Hell say Im really not even a good top,” or hell say that he likes his tops to be ultra-masculine, implying that he may not ever want to see me bottom.

Advertisement
Advertisement
Advertisement

Im trying to give him the benefit of the doubt: Maybe hes genuinely insecure about topping and nervous about being good for me, and maybe I should just trust his cautious affirmations and itll happen when the time is right. The fact remains, however, that hes topped other people since Ive brought it up. I dont want to apply too much pressure to something that seems like touchy territory, but I havent bottomed since before I met him, so Im getting horny for someone to top me and would much prefer he be the one to pop that cherry. As my partner, I feel like he should be chomping at the bit to do it!

Advertisement
Advertisement
Advertisement

I have no issue continuing to primarily top him because our sex is great and we have it constantly when we visit each other (about once a month). But I dont think I could be in a relationship with someone who topped other people and not me. Managing being open has been challenging enough; every passing month makes me more uncomfortable that other people have access to my boyfriend that I dont. Is there something else I should be considering here, or another way to broach the conversation?

Advertisement
Advertisement

— Top Needing to Bottom

Dear Top Needing to Bottom,

Let me help you give your boyfriend the benefit of the doubt: Chemistry, which can be hard to verbalize and is more along the lines of something you feel and understand implicitly, often steers the ship. As someone who is extremely vers, I can tell you that there are guys I want to top, guys I want to bottom for, and guys I want to flip with. I don’t know if I can always explain why. It’s something about what we both bring to the table and how it intermingles. Because of the way men are socialized to not express themselves kids, verbalizing something so ephemeral is that much more challenging. Shame one feels at not being able to express an answer his partner needs can compound the communication rift further.

Advertisement

I think that (or something like it) could explain why the communication on this topic has been so unsatisfying. I suspect his stock in a rather normative definition of masculinity may be the greatest contributing factor here, but it may not be the only explanation. That’s a shame, but what can you do? If you’re having great sex; enjoy that and take solace in the fact that you’re nonmonogamous and can get some outside help for your railing needs. I understand you’d prefer to only bottom in the event of romantic connection, but at least you have the option of exploring should your itch become so pronounced that it needs a scratch. If you can’t have exactly what you want, options are good consolation prizes.

Advertisement
Advertisement
Advertisement

It’s important to drop the notions of what a partner should want to do if you want to stay in this relationship. Stop focusing on ideals and start focusing on reality. Signs point to your partner not wanting to top you, and that may not change. At best, after chipping away via compassionate discussion, you may get a fully articulated reason as to why he’s total-bottoming for you, but I wouldn’t even hold my breath there either. Say this is just the way it is: Do you want to be in this relationship? If not, it’s OK, just make sure you pursue a power vers next time around.

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

Advertisement

Dear How to Do It, 

I’m an uncircumcised man with a really sensitive glans. Like, one time I decided to jerk off the way I assume circumcised men do it, with the foreskin pulled back and moving my hand up and down the head. (I did use lube—some of the free promotional stuff they give out on college campuses.) It hurt so bad, that by the time I finished, I felt like vomiting. (It was a weird pain, similar to being hit in the balls.) I’ve since stuck solely to the shaft and foreskin and avoided directly touching the head.

Advertisement
Advertisement

I’ve never had any penetrative sex, and the thought of it fills me with dread since I worry it’ll be painful. (The sensitivity means that even just putting on and wearing a condom is uncomfortable.) I don’t have any particular desire to touch myself there, and when I do, experimentally, I don’t interpret the sensation as pleasurable. But I know the head gets more calloused with use—should I be “toughening” myself up? Any ideas on how to go about doing so? Especially that’s, you know, fun?

Advertisement
Advertisement
Advertisement

— The Vulnerable Head

Dear Vulnerable Head,

You should get looked at by a doctor, just to make sure there aren’t underlying issues making you more sensitive. The kind of sensitivity you describe is sometimes associated with phimosis, but you don’t report any difficulty in retracting your foreskin, so phimosis apparently is not your issue. A doctor could help assess whether things are moving as smoothly as they should, as well as detect an issue like balanitis, which is inflammation of the glans that happens most frequently on uncircumcised penises.

That said, this could merely be a matter of what you indicated in your letter: a lack of exposure. “If his glans skin is never seeing the light of day then that skin will not be particularly ready for contact,” wrote Dr. Charles Welliver, director of men’s health at Albany Medical College, via email, in response to your letter. “Same as when you skin your knee or elbow, the exposed deeper layers of skin aren’t good at dealing with all of the things are skin deals with on a daily basis and it hurts like a mother. Eventually the epithelium (layer of the skin on the outside) repopulates the injured area and it doesn’t hurt.”

Advertisement

Welliver suggested letting it toughen up a little bit at a time—exposure via water in the shower, for example, may be all you need. Avoid a redo of your jerk-off session; take things slower. I know that isn’t “fun” per se, but it may foster some fun in the long run. That’s not nothing!

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

Dear How to Do It, 

I love being fisted. I have two partners, one of whom has hands slightly smaller than the other, and when I’m very turned on they can basically slide their lubed-up full fist into my cunt with little to no resistance (note: I’m trans and cunt is my preferred word for that hole). So what’s the problem?

Advertisement
Advertisement

I am writing this on my third day of painful GI issues and am wondering if they’re connected to fisting and what, if anything, I can do to avoid this going forward. This week, I had sex with my larger-handed partner on Sunday and then with my smaller-handed on Tuesday. Both times included fisting or something close to it that had novel elements for us (my larger-handed partner had five fingers rocking an njoy wand on my G spot; my smaller-handed partner used more of a rocking up and down motion rather than simply in and out). About five hours after the sex on Tuesday, I started having diarrhea, cramping, and uncomfortable “bubble gut” sensations that have now lasted more than 48 hours. I have been in so much discomfort that I can barely eat.

Advertisement
Advertisement
Advertisement

Not long after my symptoms started, I received some highly stressful news. I have C-PTSD and am easily affected by stress, though it doesn’t usually result in such intense GI issues, but it’s hard to imagine that’s not playing a role here. This was also the first time being fisted twice in one week. Do you think the fisting could have caused my GI issues? Is there anything we can do moving forward to avoid this outcome? I joke about how much I love having my guts rearranged, but this is really shitty!

— Gutted

Dear Gutted,

Yes, Gutted, the fisting could be the cause of your GI issues. Dr. Carlton Thomas, a gastroenterologist known on social media as @DoctorCarlton (his TikTok and Instagram accounts are popular), told me by phone that the pain and inability to eat could be a sign of GI issues caused by a fisting-related tear or injury (the introduction of a bacterial infection via fisting is also possible but less likely unless the fister’s hands were dirty). Thomas recommended a CT scan, as a perforation in that area can be life threatening. So, uh, get on that, pronto.

Advertisement
Advertisement

Moving forward, Carlton has some tips that he gleaned from an international survey he did of about 50 fisters and fistees last year (his sample included fisting tops/bottoms/versatiles). These aren’t in any strict order, necessarily. Tip No. 1: Don’t fist/get fisted while high. It could make injury less detectable. Carlton explained that long-term consequences from fisting tend to come from injuries. Less of a concern is becoming permanently stretched out because of the anus’s “incredible snapback.”

Advertisement

Tip No. 2: Don’t use numbing lube, for the same injury-detection purposes. Tip No. 3: Only play with an experienced fister so they can guide you if you’re inexperienced. Tip No. 4: Go really slow, use lots of lube, and don’t force it. “The first six to eight inches after your butthole is your rectum and it’s kind of a nice straight shot, but then there’s a giant curve that happens, a hairpin turn called the rectosigmoid junction,” explained Thomas. “A lot of fisters term that the ‘second hole.’ Because of the sharpness of the turn, if you just jam something up your ass like a dildo or even a first really fast, that sharp turn if it doesn’t have the chance to relax can be the source of a tear.”

Advertisement

Thomas’s biggest takeaway from his research was how connected an experience fisting can be—in the event that connection should fade during a section, discontinue fisting. That, too, could be the cause of injury.

— Rich

More How to Do It

I’m a woman who has recently started seeing a guy who is obese and has a hidden penis. I’ve found tons of advice online about how he can still please me, but absolutely none about how to please him. I’m unable to push the fat away from the penis and pleasure him how I normally would. I feel like I’m just manhandling him when I do give him a hand job. Also I’m unsure how to safely give him head since I can’t use a condom. I’d really like to give him the same pleasure he has given me, but I’m just stumped on how to do it.

Advertisement