How Do I Feel Confident and Desired While Dating As A Trans Man?

Estimated reading time: 17 minutes

Hey Doc!


Know my experiences aren’t ones you have, but I think it’d be good to get advice from somebody outside of them.

The background: I’m a bisexual trans guy in my early 30s. I’m not done with transition (I want to have bottom surgery, but with the way my country’s medical system works it’s looking like ~5 years in the future), but it’s been a good while and I’m relatively settled where I am (I came out at 18, next month is my 11 years on hormones, and September will be 8 years post top surgery, to give perspective).

Since my mid-twenties I’ve pretty much exclusively hooked up with and dated other trans people. I enjoy it and I think I’ll continue to primarily do that, but following a series of back-to-back crushes on my DMs, I’ve realised that ‘nerdy bisexual cis guys with beards’ is a type I have, and I want to try exploring that a bit more.

The things I’d like advice on specifically are: how do I work on feelings around desirability, and how do I practice saying ‘no’?

Some context: I am exclusively interested in topping, and I find vaginal sex with me bottoming dysphoria inducing to the point it makes me physically nauseous (and even depictions of similar kinds of sex can make me feel repulsed). The way this flows into the latter point is that the sexual experiences I have had with cis men in the past have also pretty much always involved an assumption I will bottom and/or some level of coercion around this, no matter how clear I had been around only wanting to top. I have some level of worry that if the same kind of dynamic happens again, I will ‘fawn’ in response. If you have any recommendations on exercises to practice saying ’no’, I would love to hear them.

The way it flows into the former is that, I won’t lie, I have absolutely been able to punch above my weight in the trans4trans hookup scene by virtue of how few tops there are. I do genuinely really like myself — I have a really fun sense of personal style, lots of hobbies (including ones that involve making clothing/accessories, which is great as an ice breaker), am very sociable generally, have a career that’s interesting + does social good + is important to me, am very financially stable, have a good circle of friends, and am exercising more regularly than I have at any other point in my life (while also genuinely being alright with the fact I’m still fat – I spent a lot of my teens hospitalised for an eating disorder, so that’s a big achievement).

However, I’m realistic and I know that not only does the fact I’m trans take me out of the dating pool for the vast majority of cis people, even when it doesn’t it often comes with that earlier mentioned assumption. Bluntly, I have never seen a cis man ever express a desire to be topped by a trans guy (and believe me I’ve *looked*). As a result, I really struggle to think of (in the trans4cis context) being a top being something that an audience could actually want rather than something I should apologise for. I’m not sure how to navigate going from being relatively in demand to being an extremely niche taste.

Obviously, this is not something you have direct experience with, but I reckon “how do I stop feeling like this aspect of me is unwanted/needs apologising for” feels like it’s gotta be something men from a bunch of different backgrounds can relate to.

Any/all advice welcome – thanks in advance!

Mr. Good Bar

Like you said, MGB, I’m a straight cis dude, so my experiences are not going to be the same and just as importantly, my risk factors aren’t going to be the same. So while I have my thoughts, I also want to invite my transmasc readers to share their thoughts and opinions on the matter.

Now, I think one of the things to consider when it comes to your worries is that while I know that practicing saying “no” and enforcing your boundaries is going to be important, especially in the moment when clothes may be coming off and you’re in that liminal, vulnerable state full of possibility and terror… I think you also need to feel like you have the unequivocal right to say “no”. That you deserve to say “no”, if you’re not feeling it, rather than just going along because someone thinks their idea of you trumps your knowledge of yourself.

So I think this is one of those times where “Lord give me the confidence of a mediocre straight guy” is, in fact, a valid practice.  

I’m sure you’re well familiar with the phrase “Big Dick Energy”, MGB. The term is one that gets tossed around a lot by folks who’ll argue to the death about what it means, what it looks like, whether you can have it without the attendant junk of unusual size, or whether it’s even a desirable trait in the first place… but it’s something that I think will be useful for you. The two things you mention being worried about – how to feel more desirable as you venture outside your usual dating pool and how to avoid dysphoria and the pressure to bottom with cis guys – are the sorts of things that cultivating a little BDE can help take care of.

And as a bonus, cultivating this will tap into something you already have… just not quite in the way you might think.

Now this is going to sound like a digression for a second, so forgive me but I’d like to talk about Sam Rockwell as Owen in the 2013 movie The Way Way Back.

(Surprise, it’s a stealth Learn From This! Gotcha!)

Owen is an almost prototypical failure-to-launch dirtbag, who runs a semi-run-down waterpark in New England. But despite being a 30-something with a dead-end job, utter lack of work ethic or ability to take anything seriously, he’s a shockingly charismatic, even compelling character. A big part of his charisma is just how comfortable he is in his skin and how few fucks he has to give. A lot of what makes him so watchable is that he seems almost preternaturally self-assured, no matter what else is going on around him. He maintains an air of “yup, it’s under control, I’ve got this,” at pretty much all times, even when “I’ve got this” is really just him ignoring his responsibilities. There’s not really a question as to whether he’s ever doubted himself; he clearly hasn’t. He’s incredibly comfortable and realistic about himself – for good and for ill –  and that sense of self-knowledge is part of what makes him magnetic. It’s part of what makes him seem almost unshakable, which in and of itself is pretty magnetic.

But part of what’s important – and relevant for your situation is that same sense of control and assurance even applies when things are getting tense or threatening. While he’s not an aggressive guy, he’s perfectly willing to step up and step between someone getting aggro and the dude he’s bullying. Owen doesn’t square up, get belligerent or show that he’s ready to throw a punch; he just gets between them, creates a barrier and makes it clear that to get to the kid, you gotta go through him.

It’s these qualities that – despite the fact that he’s unquestionably kind of a fuck-up and a bit of a man-child – that make him fascinating to watch but also a figure who’s unquestionably masculine without being show-off-y, full of bullshit or bluster. It’s confidence and assurance and just a hint of cockiness, mixed with irreverent sense of humor that makes it all go down easier.

This – to my mind – is a great example of Big Dick Energy that you’d want to cultivate for yourself. You don’t need to be a macho bro, you don’t need to be the sexiest thing on the block or the most butch of the butch. Instead, what you want is that bone deep sense of “I know exactly who and what I am and I don’t give a fuck if you disagree”, mixed with the feeling of “Yeah, I can handle this. I may not WANT to, but I can.”

Now remember what I said before about you’ve already experienced some of this? Well, it’s precisely as you said: you’re a hot commodity in the T4T dating scene. You know damn good and well that people like what you got and they want more of it. That, I’m sure, gives you a certain amount of swagger and pep in your step. You’re confident, you’re assertive and you know both what you’re worth and how to go out and get it.

Taking that feeling to cis dating is going to be a big part of how you both embrace your desirability and feeling like you aren’t going to buckle because someone thinks you “should” be bottoming and/or pushes for it. It’s a reminder that there’s no reason why you should accept or give in to what other people expect, simply because you already know you don’t have to and shouldn’t have to.

It sounds to me like a part of the issue is that you have a feeling that while people in the T4T scene accept you, you’re going to have to fight for acceptance and recognition with cis men. And, society being what it is and the way it treats trans and queer people the way it does, there’s a lot of acculturation that can suggest that cis acceptance is more ‘valid’ than in the trans scene. Intellectually, you may know it’s all bullshit and a social construct at best, but a lifetime of messaging about cis cultural supremacy is a motherfucker to shake.

But part of the BDE I mentioned is that you don’t need their recognition or confirmation. You know who you are; if they don’t agree, that’s their problem and they’ve self-selected to no longer be your problem. If they don’t accept you, fuck ‘em. Or don’t fuck ‘em, rather; they’re people you shouldn’t be letting into your head or your bed.

Now, again, ­I’ll be the first to admit that it’s easy for me to say this, simply because I’m a cis guy who doesn’t have the same risk factors you do. I don’t have transphobic assbutts trying to deny my civil rights and right to exist, nor threatening my physical safety because I exist. But at the same time, you know precisely who you are. You have the right to your identity, to define yourself, and they don’t get to challenge that, regardless of what is or isn’t in anyone’s pants. Or on their shelf or set of drawers.

That sense of “I know precisely who and what I am and I don’t need your approval nor your permission to be me” is going to go a long way towards warding off people who aren’t going to rock with you or the fact that you’re a top. It also will help immensely if you run into someone who thinks that they know better than you. Not only do you not have to accept their “reality”, but you reject it and replace it with your own. You don’t require their sign off to be who you are just because you’ might want to bang, nor do you need it to get down how you get down. If they aren’t cool with it, they can hop the Nope train to Fuck This Shitville and find someone who’s more in line with what they want.

I do understand the worry that you’re going from a pool where you know you’re a hot commodity to one where you might be more of a niche taste. I get how that can put a bit of a whammy on you. It may make you feel like you have to bend a little because, what if you don’t have as many options as in the T4T? What if your options among the beardy cis bi guys are slim at best? Wouldn’t that mean that the pressure to bend or to give – or to trigger your fawn response, for that matter – could be too much to hold out against?

Well, here’s the thing: that implies that being a niche taste is a bad thing. Your dating pool among the cis may not be as deep as in the T4T, but that’s ok; numbers aren’t nearly as important as the strength of the appreciation. This is part of why I talk about being someone’s shot of whiskey instead of their cup of tea. Your appeal may (and I stress may) not be as broad, but the people who you want are people who crave you, not people who think you’re ok or pretty good. And let’s be real, when it comes to boning, you want people who are looking for someone like you, people who want to be bent over by you like a champ, not folks whose interest in you come with caveats and provisos.

So, my suggestion is that you put yourself out there without apology or equivocation or shame – that BDE we’ve been talking about – and make it clear that you’re looking for bottoms, not switches or verse dudes. That’s not your thing and there’s no need to apologize for it. You’re looking for your type, and you want the guys who want guys like you. That’s not something you should feel weird or ashamed about; you know what you’re about and you know what you’re worth, so go and get what you’re worth. You deserve folks who want you because you’re you, not because of who they think you’re “supposed” to be. If they don’t like you or don’t want to rock with you, that’s fine. That just means they’re not right for you.

Yeah, it may mean fewer messages and matches on the apps. That’s fine; as I said, you want the right people, not any and all comers. They are out there. And while it may sting, keep in mind that you’re also the one who gets to say “nah” and also “well… bye.” And that includes when you’re looking at the apps and deciding who – if anyone – you’re going to swipe on.

And if you’re running into dudes who wait until the zero hour to reveal that think they think they know you better than you do? That’s nice… they can think it while collecting their pants and walking to the door.

Good luck.

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Hi Dr. NerdLove,

Long time reader, occasional commenter, first time writer. More looking for your opinion or insights than concrete advice.

What counts as an emotional affair?

Or, put another way: can boundaries limiting your partner’s emotional / romantic intimacy with others ever be healthy, if both people agree to it? I tend to think setting boundaries on a partner’s non-sexual relationships (or, limiting their emotional intimacy or platonic physical affection in friendships) causes more problems than it solves.

Personally speaking, I’m wary of the concept of emotional affairs out of, among other things, personal experience. Basically? I’m glad I ignored a friend’s suggestion my spouse “might be having an emotional affair” when they were being strange and seeming to hide something from me 2 years ago.

It turned out his workplace was highly toxic (IMO abusive), and making him feel ashamed while not feeling like he could quit. He didn’t want to talk to me because he thought I would also be mad at him (or disappointed in him) for not “succeeding” at his [again: abusive!] job. Thanks capitalism! /s

Fortunately, after talking about it, we worked together so he could quit, recover, and get a better job somewhere else. His new workplace is much, much healthier!

Ultimately, yes, he was unusually close to his coworker—because they were both trying to survive a truly toxic environment and not coping well. Yes, he was secretive about their conversations and how work was that day—because they were commiserating about the toxic environment, and he was ashamed about not succeeding there.

Given how it turned out, I’m really glad I didn’t jump to, “are you having an emotional affair? Stop being friends with your coworker!”

Yet, I know I’m Wrong About Stuff. What am I missing? I definitely feel like my perspective is missing something.

There are plenty of people I care about, who believe the opposite of me on this subject. They believe 100% in guarding against emotional affairs. I generally respect these people’s judgements! I don’t think they are necessarily off kilter or overzealous in other ways.

Likewise, I know many people are deeply harmed, even psychologically harmed by their partner emotionally cheating on them. I don’t really think they’re lying or exaggerating about that.

So…what’s the missing piece?

Are there types of relationships or choices that count as “real” emotional affairs? Which boundaries are wise, and which ones are controlling?

Looking forward to hearing your perspective.

Sincerely,

Platonic Love Polyamorist

OK, I’m going to be real with you, PLP: I think that there’s way too many people who keep trying to broaden the definition of “cheating” while also making the definition of “monogamy” so restrictive and so limited that they end up creating a no-win scenario. The more you define perfectly goddamn normal behavior as “cheating”, the more you’re going to find cheaters and oh look, more relationships that wither and die that didn’t need to. Especially if “cheating” of any sort keeps getting held up as the worst thing you can do in a relationship.

Now, I will say that I think it’s possible for someone to be giving so much of their time and energy and attention to a person – a person outside of their romantic and sexual relationship – that it becomes a problem. I think people can have relationships where the emotional intimacy that they would normally be sharing with their partner is being shared with other people, and this can create problems in the relationship.

But I think that most of the time, what people are defining as “emotional affairs” are just friendships. Close friendships, or friendships where the romantic partner may feel excluded, but friendships none the less. I think a lot of the agita around the concept of “emotional affairs” springs from the same place as the idea that men and women “can’t” be friends because of sex and that emotional intimacy is equivalent to romantic intimacy.

Similarly, I think it ties into the idea that romantic relationships are inherently superior or sit at the top of a hierarchy, and that friendships couldn’t or “shouldn’t” be given the same level of import, deference or status in a person’s life if they have a romantic partner. Or that people don’t have a right to privacy or emotional autonomy when they’re in a relationship. And I think this ties directly into a hell of a lot of stressed-out relationships, where one’s romantic partner is supposed to be all things to the other, with the attendant strain that puts on an individual.

And then people talk about the male loneliness epidemic and wonder why guys have fewer friends that they can share their feelings and troubles with or turn to for support.

I think it’s good for people to have friends and a life outside of the relationship, even aspects to it that their partner doesn’t know about or isn’t intimately familiar with. Not only does this distribute the weight of a person’s needs for connection, affection and support, but it also helps strengthen the romantic relationship. One of the killers of a romantic connection is familiarity and boredom. Part of what makes the early days of a new love so heady is the novelty of it all; you’re both learning about one another and finding new and different things. But not only are humans endlessly hedonically adaptive, but when you’re with someone for long enough… there’re precious few surprises left. There’s very little novelty when you’re with someone you’ve seen wracked with food poisoning or covered in sweat and dirt and stinking to high heaven after a long day working in the yard or garden. Having those outside connections and outside experiences gives more room for growth, novelty and discovery – for both partners.

And to be perfectly frank, sometimes there’re reasons why a person might want to share one aspect of their life with someone besides their romantic partner. It may be a fear of shame, a desire not to burden their partner with knowledge they could do nothing with, or even simply that their partner isn’t going to have the ability to understand – not the same way that someone else might. Your spouse trying to deal with a toxic work environment is a prime example; their friend and co-worker was in the same boat and having the same problem. It’s entirelyunderstandable and reasonable that the two of them were going to lean on one another for support. They knew exactly what was going on and what it was like. It made perfect sense that they’d turn to someone else who’s also going through the shit, like a pair of veterans in the same foxhole. You may have been willing to offer what support you could, but that’s not going to be the same as someone who’s dead bang in the middle of it too.

I do think “emotional affairs” can happen; I just think that it’s far more about other people making a lot of noise around mistaken ideas about male and female relationships and unreasonable expectations regarding the concept of romance and monogamy. I think that friendships, even emotionally tight and intimate ones, are good and important; it’s when they’re actively taking away from another relationship that they cross the line into “emotional affairs”. But what most people describe as “signs” aren’t indications that they’re actually losing out or having something taken from them, just the fear that something might be. And frankly, I think a lot of the discourse around the concept of emotional affairs comes from the perverse incentives to focus on fear and uncertainty, not from actual risks.

Good luck.