Do I have to be masculine to be a top?

Unpacking some feelings of gender in and around sex and sex acts.

Johannes T. Evans
11 min readMar 13, 2023

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Photo by Anete Lusina via Pexels.

Another blog post coming from an anonymous ask on Tumblr!

Anonymous asked:

Okay so similarly to last anon about topping as a trans guy/trans masc, how do you build the confidence within yourself to top someone with a penis? Cause my partner is super kind and willing to let me learn but I struggle with my own mental barrier of lime not being “manly” enough or confident enough for topping. I know a lot of it is internalized transphobia but I just wasn’t sure if you had any past experiences that helped you over come that or other fears surrounding newness and such.

That sounds like a tough set of feelings that are all mixed up together!

I’m gonna unpack some gender stuff and ungendering things first, and then specifically get onto feelings of masculinity, because I think those are two separate mental processes that are (understandably) tangled up.

Before I go on, though, there’s a lot of thoughts and exercises I’m going through in this essay, and I just want to say that more valuable than anything I’m about to say re: your sexual relationship with your partner, is to talk to them.

]Everything below is ontological gender thoughts and then feelings about your own confidence and masculinity, but given that the important thing here is your sexual chemistry and dynamic and relationship while the two of you fuck, their feelings and thoughts might well be super valuable here!

Even if you just say, “Hey, I asked this pretty writer fag for advice because I’ve been feeling these feelings and it’s been tough for me, would you also like to read what he said?”, that might be very helpful and valuable!

All these big feelings and big problems often feel less big when we share them with those we love and are intimate with. A problem shared is a problem halved — an insecurity shared with a trusted someone is one that can be soothed and be specifically treated with gentle gloves. If your partner doesn’t know about it, they can’t do that!

Anyway, on to me talking too much:

Me and my boyfriend were at a kink event yesterday that was very straight-dominated, and one thing that sort of occurred to us that we don’t tend to think about, because we’re not really in community with cishets and their sexual culture, is that for a lot of cishets, “pegging” — a cis man being penetrated with a strap-on, by a woman or by someone else without a cock, is in itself considered a kink.

And Lewis was like, “And that’s ridiculous because it’s just like… It’s the woman topping. It’s not special or important because it’s just two people in a relationship and she’s the one topping, but because they’re straight, it becomes about him being humiliated and her dominating him when it’s literally just normal.”

And he’s obviously right, like…

People often assume that in a sexual dynamic:

the top = the dominant partner = the more masculine partner

the bottom = the submissive partner = the more feminine partner

But the act of topping or bottoming (which I’m using in this context to refer to someone being the penetrating or penetrated partner, although “top” and “bottom” are often used to refer to a partner acting versus a partner acted upon, which is explored and discussed a lot in this glorious piece, Top or Bottom: How do we desire? from The New Inquiry a few years ago) is not in itself an act of domination or submission.

You mention not being confident enough to top, and link that confidence with your masculinity — do you think of topping as an inherently more confident act than bottoming? Is there a certain security you associate with topping, or a certain certainty of thought or intention, that you might not ascribe to bottoming, because you think of bottoming as passive and topping as active?

To be penetrated is not to be subjugated, nor is penetration in itself an act of subjugation, or emasculation, or even domination.

But while we still think of penetration as domination, we automatically association that act of domination with masculinity, with butchness, with being (as in the essay) the brute, with being the actor upon the acted, with being the “active” (as opposed to passive) partner, etc, because in cishetero ideals of sex, sex is something done by the man to the woman.

But you know trans girls that top, do you not? Whether that’s them fucking boys or girls or other people entirely, there are trans woman who top. They are not less feminine for doing so, they’re certainly not less womanly.

And you know cis men that bottom, yes? And not just twinky, effete, fairy boys who are fruity with lisps and grabbable hips and pretty eyes — there are big, hypermasculine butch men with glistening muscles and thatches of thick hair on their tits who just stepped out of a Tom of Finland poster who love to be fucked. It might well be those ethereal fairy boys who are doing the fucking.

Perhaps they like to be bent over and fucked — perhaps they like to lie back and cup the faces of their partner and coax them into fucking him, smiling sweetly, saying, “That’s it, come into me, you’re doing so well, yes,” and treating it as an act of love and tenderness, but also, one in which he is still undeniably in control and the dominant party, but not by way of typical masculine, patriarchal performance. It can be anything it wants to be, depending on what the parties involved are intending, what they’re thinking, feeling.

What the fucking signifies and what it means is in the eye of the fucker.

Is a cis woman topping her cis man boyfriend masculine? Is she actually taking away his masculinity, or is she having any for her own? Is she less or more feminine because she uses a strap-on? Is it more or less so if it’s matched to the colour of her flesh?

What if it’s pink?

And all of what I’ve just said really assumes a binary of tenders, of the transfeminine and transmasculine as extensions of the cisfeminine and cismasculine, as parallels of their gender thinking that in themselves are, you know, constructed by the dominant culture — white Western imperial culture, where that binary was constructed and where those boxes exist to oppress and to control, through a flimsy defence of “biology” and also through constructed social roles.

How much do you believe in that stuff?

Play it out as a mental exercise — make a list (you don’t have to write it down, you can just think about it in your head) of the sex acts you and your current partner do together, and the sex acts you’ve done with other partners, and other sex acts that you’ve dreamed about or fantasised about, and ask yourself…

Do I think of this sex act as more masculine or feminine or is it gender-neutral, or do I think it’s genderfucky in some way? If it’s genderfucky, in what ways is it genderfucky?

Is it genderfucky because it particularly adheres to or particularly subverts certain gender roles in or outside of the bedroom? Is it genderfucky because it exists in some way outside of the gender binary for you, whether that makes it genderless or genderful, or abstracts it to some entirely different kinds of gender?

For example, if a cisgender man is penetrated by someone else’s homegrown cock, how does that feel, genderwise? What if it’s someone else’s cock as a strap-on? Does the colour or consistency or size of that cock matter in the equation? What if the person penetrating him is an android, and their cock is part of their body, but it’s metal or silicon or otherwise matched to their robotic body? What if the person penetrating him is someone who’s had a phalloplasty, and their penis was made via surgery and a cool skin graft from their arm? What if it’s a fantasy universe where the person did have a clitoris, but they drank a potion and it turned into an average or more-sized typical cock? What if the person penetrating the man is a tentacle monster or some other kind of alien creature, and they do not conform with the bipedal constraint of the human form?

What if all of that is the same, but the cisgender man being penetrated is now a transgender man? What if all this happens to a transgender woman? What if all this happens to a cisgender woman? What if all that happens to a nonbinary person?

If that nonbinary person was assigned female at birth, or if they were assigned male at birth, does that change your feelngs or your assumptions? Why? If that person has had different surgeries of their own — phalloplasties or vaginoplasties, penectomies or mastectomies, metoidioplasties, or any other kind of genital reconstructive surgeries? Does that change anything?

And that’s just the act of penetration, but you can think of any other kind of act that you do during sex or as a lead up to sex — kissing, massage, biting, frotting, using a vibrator, nipple play, spanking, dressing up, etc etc. How does gender play into it? What are you gendering, and what are you not gendering? What about the language you use? Say, calling a cis man’s chest his tits or boobies or breasts or his mommy milkers, but calling a cis woman’s chest her pecs or her chest, or even her man boobs?

What acts do you see as adhered to specific gender identities or presentations or ideas of gender, and which acts are more flexible or unattached? Why are they different? What makes them different?

So that’s part one of this, yes?

And all of that is. A lot of thinking and a lot of ruminating, and by no means am I saying you have to sit down and get it all done tonight like it’s homework due tomorrow — that’s more a set of thoughts and ideas that you can start unpacking as they come to you? As you think of new things, you can play with those thoughts and unpack them, and compare them and contrast them to each other, and see how much actively thinking about and deconstructing them in your head changes your feelings about them — and how much your feelings stay the same.

No matter what thoughts come up as you go through this, no matter what biases you find you have, or thoughts you find that you don’t agree with once you start examining them, that is okay. There is nothing wrong or bad about how you think or feel.

None of the above is intended to lecture you, none of the above is intended to make you feel bad or insecure or like you’ve done wrong by having different thoughts or feelings about the different genders of things.

You have not transgressed by holding a bias, or by thinking of a sex act as masc or fem rather than neutral, or anything similar.

You have not transgressed. You have not sinned. You have thought thought bad thoughts, and subsequently are a bad person, or a bad queer, or a bad trans person.

This business of unpacking and untangling gender and sexuality from specific sex acts, of ungendering things or adjusting our lenses of gender, is hard and difficult and complicated work. Many thousands of essays have been written on this subject by other queer people, by BIPOC, by disabled people, by trans people, by intersex people, by everyone who has not been written into the constructed white imperial gender binary and its associated ideals of sex (which themselves have been escalated and fine-tuned and commercialised because of capitalism and other forms of white cultural supremacy), because it is hard and difficult to do. Because these are things we all have to unlearn, which is difficult!

A lot of these feelings, when we start unpacking them, cause us pain and make us feel discomfort, nausea, dysphoria, shame, uncertainty, fear.

They make us feel that way because by our existence, we are transgressing — because we exist in the way that we do, outside of this constructed binary (and unwilling or unable to conform to it, or at least feign / perform conformity), we disrupt it and we break its rules and we twist it and we bend it. Simply by being, we do those things.

And then when we start to look inward and really start doing that work, it can feel insurmountable and impossible and agonising, because how are we to unpick a framework which we’ve been sewn into our whole lives? How can we unpick our threads from a tapestry when we’re sewn into it with surgical thread?

It’s not our fault. It’s not your fault or my fault, it is not our partners’ faults, it’s not even our parents’ fault or our teachers’ fault or any individuals’ fault.

But it’s a process.

So. Coming away from the broader thought exercises and zeroing in on your personal feelings about your own body, your own gender, your own role during sex.

How do you feel more manly? How do you feel more confident? How do you get past that barrier and feel “ready” to top?

If you want to top while feeling in control…

Does your partner normally top you? What positions do they usually top you in? Are there any positions they top you in that make you feel more vulnerable in some way, more controlled by them, in a way that you enjoy? Do you think that using those positions, you would then feel more like you’re in control?

Would you feel more confident, for example, topping doggy style rather than in missionary?

Have you considered fingering your partner first and penetrating them not while fucking them, but during some other activity? So, blowing them while also fingering them, or using toys on them? Using a vibrator or a dildo on them while giving them a handjob? Even watching them fuck themselves on a vibrator or dildo while you give instructions — so not touching them or moving them down on it, but they only move as instructed by you?

All of those are playing with you being in control and dominating while they’re also being penetrated, but is not necessarily topping them while fucking them with your own cock — you can use them to ease yourself more into the mental role or more of the confidence of what you want, rather than plunging directly in (pun intended).

There’s roleplay, where you could play out a specific fantasy or wear a particular costume or outfit or something similar, that lets you feel more or at your most manly and confident, so that it’s easy to really lean into a butch persona if that doesn’t normally come naturally to you?

If you think you’d be more confident topping while ceding some control, have you thought about different positions for that? For example, you lying back and your partner riding you, and easing themselves down onto you?

Or you topping them while they instruct you exactly how to move, or you’re being guided by them, acting more in the service top area?

Another option is double-ended dildos! I’m not sure how comfortable you are bottoming or being penetrated, but if you do enjoy such things, a double-ended dildo means neither of you are topping, but you’re both bottoming, and that can be somewhere interesting to start that’s focused on the sensation and experience together.

All of the above you can then use to transition into topping your partner more the way you first envisioned, or first fantasied about.

Sorry that’s a lot to chew on, Anon, but I hope it helps and I wish you love and luck! Like I said to the other guy that asked about topping, so much of this is like…

Because it’s new and because you haven’t done it before, it can feel like it’s a huge and impossible thing, and then once you do do it, a lot of that mystique and that sense of infinity (infinite things that can go right, infinite things that can go wrong, infinite emotions one way or the other) fades away a bit!

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Johannes T. Evans

Gay trans man writing fantasy fiction, romance, and erotica. Big on LGBTQ and disability themes, plus occasional essays and analysis. He/him.