How to Do It

It Crushes Me That Well-Endowed Guys Can Do Something I Never Will

A man pulls out his waistband to look down, while a small eggplant glowing nearby.
Photo illustration by Slate. Photo by grinvalds/iStock/Getty Images Plus.

How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to Nothing’s too small (or big).

Dear How to Do It,

I spent the first eight years of my sexually active life as more of a top (cis gay dude here). Bottoming was … fine in terms of feeling intimate with someone I loved, but other than that, I could take it or leave it. Then, in a span of two weeks, I discovered poppers (and that I’m just very tight) and met an absurdly hung dominant top who knew what he was doing. The sex was literally life-changing, and I started leaning into my bottom truth ever since.

That was about five years ago, and after several years of predominantly bottoming, I’ve recently found myself wishing my pendulum could swing back toward being more solidly versatile. My problem is I am averagely hung—the literal actual definition of average. And I now know from experience that there are just some spots a guy like me can’t hit, and it kills me. While the many dudes on Grindr who immediately block you upon seeing a picture of an average dick certainly haven’t helped my self-esteem here, I did get great feedback in my topping days. I got great feedback from exes who moved to meccas of gay sex, screwed their way through those fields of joy, and still would later hit me up saying I was memorably good.

The point is, even with a pretty strong loop of positive feedback, I’m still so self-conscious I can barely get hard to top any more. Every time I’m close to thinking I could make a guy happy as a top again, some absurdly hung guy breezes into my life and plows me so deep I feel both hollowed out for the next 24 hours and like I could never please a man again. I know this is all in my head from experience. I obviously do like sex with well-endowed guys, but most of my regular doms where I live are comparable to me, and I still love getting it from them. Any thoughts on what I can do to get over this and get my, er, head back in the game?

—Sizing Up

Dear Sizing Up,

Make like your road-tested butt and relax. This really does not have to be fraught or complicated. Find a willing guy, maybe use a cock ring and/or an ED med just for the peace of mind that results from the assurance of a rock-hard dick, and go to work. While I appreciate your golden-rule method of bottoming—aim to hit the spots of others as you would like your spots to be hit—ehhhh, that’s not where a lot of guys’ heads are at, so you should be fine in most cases. You have collected data yourself that points to this very idea, in fact. Trust your life experience.

You’re probably going to be better off starting with a bottom who isn’t pushy—I recommend another vers dude or even someone who calls himself a top on most references. Guys who generally top, I find, are so hungry for dick that they come fast and your performance amounts to little more than showing up. I bet that once you successfully satisfy a guy with your dick, it’ll effectively get you over the hump and facilitate even more humping. But if that doesn’t happen, even if you’re effectively sentenced to a life of bottoming, I know you’ll be OK. You make your sex life sound like a traipse through a cornfield, except instead of ears of corn, there are giant dicks everywhere and they’re coming just for you. Don’t take this abundant harvest for granted. Sink your teeth in and enjoy.

Dear How to Do It,

I’m a woman in her late 20s in a relationship with a man in his 30s. While we started off in the same location, we are currently long-distance and will be for the next two years. Although we will be able to meet up in the middle sometimes, this feels like a really long time to go without regular sex with the person I love. To that end, I’d like to give sexting, and maybe phone sex, a try. I’ve never done either, but it seems like they could be fun.

When I brought up the idea before we moved, he seemed game, but now I’m not sure how to actually do it. I worry that I’m going to sound ridiculous, or crass in a not-fun way, when I ask for it in the moment, because I can’t rely on physical chemistry to smooth over any awkwardness. I’ve tried testing the waters with statements that are sexy-flirty, but I don’t get much of a response beyond things like “I love you too” or “I miss holding you.” Those things are true, and I appreciate them, but I also want to get off when I talk to him. When we are physically in the same space, he tends to be a lot less verbally expressive during sex; I, on the other hand, love to hear a partner talk about how good X or Y feels. I read and write erotica regularly. I just don’t know how to start doing those things in our relationship, but I’d like to find some ways of maintaining our sexual connection as well as the emotional one while we’re apart. And it may be that this is just straight-up not a thing he’s comfortable with, which is perfectly fine—I’ll just need to buy a lot more batteries, fast. So, what are your best tips for initiating phone or text sex? If your partner isn’t into those things, are there other methods you’ve found for maintaining a connected sex life in a long-distance relationship?

—Pillow Talk

Dear Pillow Talk,

I don’t want to worry you, but your letter worries me slightly. Could your man’s reluctance to engage signal some sort of broader relationship issue? It might be a good idea to check in and just make sure he’s still on board. (Long-distance arrangements are, after all, major efforts.) After you get his reassurance, ask him if he’s interested in having any semblance of sexual contact when you’re apart and if so, what he’d like to try out. You may have to set your rhythm to his.

From there, keep it real. For real: Don’t pussyfoot with “sexy-flirty texts” that he could interpret as merely friendly or affectionate; tell him you’re horny and thinking about him. Tell him what you’d do if he were with you. Talk about sexual encounters that you’ve had with him. Trust your muscle—the writing one, that is—and don’t worry too much about sounding ridiculous. Horniness has a way of helping people tolerate things that might sound silly in other contexts, so if he’s into it, your verbiage won’t matter too much as long as it’s not outlandish.

If he’s still not receptive, remind him that you’re doing this for the two of you, but do listen to him. It’s reassuring that you’re at peace if this kind of talk just isn’t his thing. In bed, people are like parrots, in that some of them talk, and some not so much. If he’s reticent but still into the idea of long-distance contact, I suggest trying video. My friend in a long-distance relationship told me that just jerking off with his boyfriend via FaceTime makes their time apart much easier.

Dear How to Do It,

I have a good friend who has a habit of, nearly every time we get drunk alone together, coming home with me. It’s been escalating—last time we definitely did reciprocal oral, and we may have briefly had sex. (Neither one of us is sure because we were so drunk, which is ridiculous.) The problem is that when he’s sober, he doesn’t want us to hook up. After each time, he says this is a bad idea, that we shouldn’t do this again, etc. (It’s never I wish we hadn’t done this, only we shouldn’t do this again. My view: It is a bad idea, but that ship has kinda sailed.) When he’s sober, absolutely nothing happens. After the second time a couple months ago, I broached the idea that we should just hook up, but he said he didn’t want to complicate things because he enjoys hanging out with me. When I’m drunk, I’m pretty slutty; I’m extremely unlikely to say no in most cases, especially since I can’t help thinking we should just have sex. He’s the one who doesn’t want to while sober, but when he gets drunk, he can’t seem to not come in. At this point, this to me is getting a little ridiculous, but I’m not entirely sure what I can or should be doing here. For context, neither of us is interested in a dating or a relationship of any kind—I have other friends with benefits. At the same time, we live in a very small town, and going out to bars with him is an important part of my social life. Thoughts?

—Drinking Buddy

Dear Drinking Buddy,

Take away the substances and your picture could be printed next to unrequited in the dictionary. You want it more than he does—“it” certainly being the sex, it seemingly being an ongoing play-buddy arrangement, and it quite possibly being a full-on relationship, though you say otherwise. If he’s not budging, you’re going to have to maintain your appetite for the scraps he’s having you feast on. You prepared for that?

Personally, if someone only wanted to get naked with me when he was drunk, I’d feel pretty insulted. Is the circumstantial implication that he’s viewing you through beer goggles? Does he harbor some sort of shame about having sex with you and/or sex in general? Regardless, are you sure you should have sex with someone usually reluctant when you’re both drinking heavily? Is all of this way too fraught for a casual arrangement? I can answer that final question from here: yes. Yes, it is. Exercise some self-control and keep things platonic. Keep your drinking buddy, and find a new guy to fumble around with drunkenly—one who’s keen to play sober, as well.

Dear How to Do It,

I’ve been raped twice in my life: once at 16, and once more than 12 years later. This second occurrence was less than a year ago. I took a period of about six months solidly off dating and sex. I went to therapy, and emerging back into the scene now, my intention is to approach everything differently, valuing my boundaries and my safety. This has been life-changing for me.

I met a man this summer whom I chose to have sex with. It was scary, but also wonderful, and he has been extremely supportive of me and willing to lend an ear. Here’s my dilemma: I’ve always been an outgoing, charming, sexual woman. Men ask me out all the time. I don’t have any interest in being in a polyamorous relationship, but I also don’t feel ready to commit to this man, even though I know that he wants me to. I think that his feeling of safety in a relationship depends upon being monogamous. I’m not ready to take that step of commitment with him, and because it felt so good to flirt and connect and have sex with this man who respected me, I want to do that MORE with other men (and women!). I am concerned about balancing his need for safety and trust along with mine. I’m also wondering: If I go out and date all these other people and keep telling my rape story over and over again seeking validation and comfort, maybe it will be too much. Am I taking what this man is offering me too much for granted? If I am valuing my safety above all else, does that mean I have to let some of my desires fall out of the equation?

—Safety Zone

Dear Safety Zone,

Bravo for being so proactive in healing. Given the violence and ensuing trauma in your past, I think you’re entitled to be a little selfish right now and really go for what you know you need. This guy sounds great, but it’s not like it took you eons to find him—it was just a few months. There’s a mismatch of sorts happening here, and I don’t really think you should squeeze yourself into his box.

As for “valuing your safety above all else,” I don’t want you to think that what happened to you could have been avoided if only you had done something other than what you did. You didn’t deserve it, ask for it, or invite it. It could have happened regardless of the specifics that were under your control. You can’t live in fear, and it seems that you have already resolved not to. Emotional safety may be another matter—you may find that an active sex life with many partners is exhausting or intense, in which case pumping the breaks will serve you well. You just have to feel it out and stay in touch with yourself.

There’s a big “but” I need to insert here: It sounds like you are thriving, but I think you can do even better by not actively seeking validation from others. Yes, outside attention and affection can be validating, but when you make that kind of validation a priority, its absence can be devastating. The only lasting validation—from telling your story, from dating, from sex—can come from within. Make yourself, your well-being, and your pleasure the priority.


More How to Do It

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