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How to Do It is Slate’s sex advice column. Have a question? Send it to Jessica and Rich here. It’s anonymous!

Dear How to Do It,

I have been seeing a new guy for about three months now. We’re having pretty good sex and he’s fairly adventurous from what I can tell. There is something I enjoy doing in bed that hasn’t naturally come up and I’m not really sure how to pose it to him. I’d like to peg him if he’s into it. It’s something I tried out in my last relationship and we both had a lot of fun with it. It ended up being a real high point for the both of us. But I’ve never done it with anyone else, hence the nervousness about figuring out a way to bring this up. What’s a way to tactfully mention it without getting his defenses up? I feel like most men won’t take it well because of the obvious societal reasons and I don’t want to screw up the good thing we have going.

—It Could Be Fun

Dear It Could Be Fun,

I agree with you—this is potentially perilous territory. The straight(/-ish) guy psyche is such a delicate thing that such a proposition could trigger a crisis as easily as it could trigger a boner. I think the main thing to do here is not to indicate or imply that there is something that you saw or felt in him that led you to this interest. So instead of proposing it by saying, “Do you want to get your butt played with?,” you might lead with yourself: “I love to play with guys’ butts. Is that something you’d be interested in?” As you may know as an experienced butt-player, it’s best to ease into a guy’s hole. I wouldn’t jump to pegging right away, as that could also scare him off. If he says he is interested after you ask, you can then probe exactly what he’s down for. Fingering, rimming, playing with toys, and, yes, pegging can all be floated as options. Let him guide your pace. Maybe you start with fingering and he likes it so much that he wants more.

I think if he’s down, and you start moving slowly but he’s obviously loving it but things aren’t quite progressing, then you can bring up your pegging past and how much you loved it in your last relationship. That may help him along. Remember to approach him as you would his butt: with lots of patience and lube.

Please keep questions short (<150 words), and don‘t submit the same question to multiple columns. We are unable to edit or remove questions after publication. Use pseudonyms to maintain anonymity. Your submission may be used in other Slate advice columns and may be edited for publication.

Dear How to Do It,

I’m a 31-year-old bisexual trans man. My transition began at age 15 and I am now stealth, live as and am seen as a man in every way. I have been saving up for phalloplasty but it will still be many years before that will be a reality. I absolutely do not want anyone outside of my immediate family and an extremely close handful of friends to ever find out that I have “female anatomy.” It doesn’t matter how accepting they are or if they’re trans as well, other people knowing about it at all gives me horrible dysphoria.

The only sex I’ve had was as a teenager, when I was unable to be stealth and allowed boyfriends to do things that I really hated because of my dysphoria, I was afraid of disappointing them by setting boundaries. I have tried dating asexual people, but found that dating at all just makes me more aware of what I can’t have.

Lately I’ve been more and more tempted by the idea of trying to find casual sex partners, be that a fuckbuddy or hookups, who would be interested in me getting them off with my hands and/or mouth but wouldn’t mind me keeping all my clothes on. Someone sitting on my face or fucking my mouth seems like pretty much the only sex that I could actually have without outing myself and being miserable. Lesbians seem to have it pretty easy with this situation where being “stone” is a normal thing for someone to be, but for a man it seems to be pretty much unheard of.

Even if I present myself as exclusively orally fixated, will potential partners suspect something if I don’t get a noticeable erection from giving head? Would you be suspicious, in a potential receiving partner’s shoes? I have a normal packer, but should I try and find one that gives the impression of a semi, maybe? I know that using a glory hole would solve this problem but that’s a lot less sexy to me. Do you have any advice on how I can have any kind of sex life without feeling like I have a giant blinking neon EUNUCH sign over my head?

(Please don’t suggest therapy to “accept” more people knowing that I’m trans. I spent plenty of time being out and everyone, even other trans men, still seems to think having a vagina is in some way a reflection on who you are, casually expects you to enjoy or not mind talking about it or even using it, or they act like we’re some kind of “men lite.” I suspect that once I’ve had bottom surgery, I won’t mind more people knowing that I was assigned female at birth, but right now all that does is remind me how much I hate my body.)

—Frustrated and Emasculated

Dear Frustrated and Emasculated,

In my subjective experience/understanding, if I brokered no-recip oral sex that was going to be performed on me, I wouldn’t be particularly moved if that which is in my partner’s pants remained immobile. In this kind of sex scenario, my pleasure is his. It’s not about his dick, it’s about mine. That’s the understanding. I would not bat an eye, because I know there are plenty of guys out there who identify as cocksuckers and that their dick is off the table entirely. I don’t know how you’d fare with a woman. I’m sure you could find some that are understanding but vaginal penetration is so common that the lack of an erection could arouse suspicions that it wouldn’t in a seasoned queer guy. I think nonetheless if you state upfront that your mouth is going to be used and your dick will not be involved, most who take you up on this offer will continue accepting that. They may ask why you don’t want reciprocation or why your dick won’t be involved, but as long as you have an explanation for them (“Not my thing,” is something vague but true that could be your go-to), many will accept this if they’re into what you’re offering. There are a lot of people out there who love receiving oral sex, so I don’t think you’d be particularly hard up, especially if you advertise your services on a kink-friendly app like Feeld or FetLife.

I think this would be a good path for you. It is very common these days to state your interests upfront and to be openly particular. Again, this often comes via stated kinks but having certain limits baked into the experience is something with which most people who hook up are familiar. Minds are more open than ever. People know that you like what you like. Contentious lovers will not challenge this, though horniness does drive people to test certain limits at times. That’s to say that there is no way to absolutely ensure that you won’t be clocked or questioned. It’s a risk that you will be taking every time you hook up. You have gone without for so long in order to protect yourself. Branching out does seem like the right move, but if the potential questioning is too excruciating to make experimenting worth it, waiting until your phalloplasty is probably the safest bet.

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Dear How to Do It,

My girlfriend and I have been talking more seriously recently about finally making a threesome happen. We’ve talked about it for years but usually as a shared fantasy that we weren’t going to make happen. But we’ve started talking about it more and have thought about whether we should just do it. How do we figure out which fantasies are better left between us and which to make happen? Complicating this I think is that there will be another person involved and we’re both wanting to respect this other person’s feelings and experience too. Is there a way to test run it before doing the full thing? We really don’t want to get caught in drama of our own making just because we were a little bored and unprepared. But we could also seriously be overthinking as we both tend to do.

—Discovery Phase

Dear Discovery Phase,

Opening up, even in a limited, we-only-play-together capacity, requires consideration and communication. “Overthinking” here, then, would amount to talking yourselves out of a good time or a threeway all together. Up until that point, no amount of thinking is too much thinking.

You’ll probably have to experience this stuff via trial and error. You won’t know you’ve gone too far until you’re there, but the good news is that it’s generally easy enough to scale back at any time. It helps to think of yourselves as a team—if one feels scared or just bad about stuff, the other should be able to course correct, soothe, and reassure. If one wants to shut down the threesome, the other should be amenable, no matter how much fun they are having.


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Ahead of time, discuss your fantasies. Write them down in a list and then review it. What seems doable/not overly intimidating from this vantage point? Start there. Maybe you keep things really light—kissing, manual, oral at most. Maybe that wouldn’t quite satisfy you so you consider vaginal/anal penetration. In any case, don’t expect things to go too close to plan—there are three people involved here, so things may go off script in a way you didn’t expect, which is OK. Be flexible, expect the unexpected, and don’t get too caught up in how things “should” go.

To help orient you, it may be useful to discuss with your potential third what they’re into/interested in doing with you both. This would be your test run: Meeting up before sex to check the vibe and see how much chemistry exists between the three of you before your clothes come off. It should be a low-pressure hang that is designated as such. No promises that it leads to anything else, but if it goes well, it just might end with the three of you in bed. Definitely do not bring any drama in front of your potential third. There’s no better way to kill the chances of a good time or a threesome happening at all, for that matter.

—Rich

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Last night, I went on a date last night with a great, interesting, funny guy that I got along very well with. After dinner, he told me that he has a medical condition that causes incredibly painful erections and, because of this, has had difficulty with intercourse (and subsequently, online dating). Later on, when his pants came off, I found that his penis was bent upwards in a U shape with his head pointing back towards his stomach. Am I a total dick if this is a deal-breaker for me?

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