How to date & hook up in a changing transmasc body.

You don't need wait, you don't have to pass -- your life begins now.

My first Grindr profile picture, circa May 2021. It got a lot of positive attention; the tits and my estrogenized skin were not a problem.

How should a newly transitioning person embark on dating, when their appearance and identity are still rapidly shifting and they’re not sure how they’re read by the people they want to get with?

Should a person wait to date until their identity feels more cemented, or dive forward, knowing that a ton about them is still going to change?

And can a trans guy really find acceptance among queer men if he doesn’t “pass” (and might not ever)?

These are the questions we are pondering in this week’s Sex Lib. I’ll let the anonymous question asker explain their dilemma:

Oh Anon, I am overjoyed that you’ve written in, because it gives me an opportunity to distill everything that I have learned in the past four years of slutty gay transgender life in one place, hopefully preventing you and others from delaying your new life the way that I once did.

(I recognize, of course, that I cannot actually keep you from making your own wonderful mistakes, and I wouldn’t want to deny you the lessons of them. I think sometimes those of us who came out as queer later into adulthood project our regrets onto younger and more newly-out people, thinking that if we can just spare them the pain we endured, we will heal. But I have also been on the receiving end of this kind of treatment when I was still an egg, so I know this impulse is badly-boundaried and pushy.

I will be encouraging you to take full grasp of your new life as soon as possible throughout this piece, but I will also be sharing some warnings and pointers. In the end, I hope this helps leave you feeling better prepared to venture out into gay dating than I was, and that you make better, more glorious mistakes than the ones I did.)

The first thing that I really want to emphasize to you, Anon, is that you do not need to wait to start expressing your desires ever again. Nobody arrives at such a dramatic change in their identity and orientation hastily; you have waited long enough, questioned yourself plenty, and made enough of those damning, practical little sacrifices that keep the life you want at bay. The days of waiting to become the type of person who leads the life you want can be behind you forever. The way we change who we are is by changing our surroundings and actions. Not by transforming our insides, or even how we look.

It is understandable that a newly-out trans person believes they should wait until they have their presentation and self-conception on lock before they risk romantic rejection from others, even if it is kind of self-defeating to hold back. For a long while you’ll be party to all kinds of trippy physical changes, from the (likely) widening of your feet, to the spreading of your shoulder muscles, to the thinning of the hair at your scalp. While all of this happening, you’ll probably be experimenting with a significantly different wardrobe and new ways of thinking about yourself, testing out vocal affects, mannerisms, and names, losing old friends, adopting new hobbies, and going through psychologically ravaging phases of anger and grief.

Amidst all this uncertainty, it can be tempting to hang back on the threshold of your new life, waiting until you have a firmer sense of who you are and how you are perceived by others before you start dating. But to be frank with you, the average transition is destabilizing for multiple years, it kinda has to be, and so you might as well find some damn pleasure and companionship as you ride the waves.

The biological part of a gender transition is ongoing for life; your voice will still continue to settle for three to four years, on average, if not longer, your height and musculature and the number of hair follicles on your back and face will continually change until you die. To get comfortable with a transitioning body is to make peace with aging, and the impermanence of all things.

Physically transitioning is also a meditation on abandoning control. Some people take T injections for years and simply never start passing, due to some quirk of their genetics. Other people become bears way sooner than they ever anticipated, or discover they’re interested in a completely new sexual role than they used to be. You can’t ever really know how your transition will settle on you; the way that we figure out who we are is by doing things, and building relationships with people. And it is never too soon (or too late!) to start exploring that.

Of course, that is only the existential side of the matter. You’re also worried about far more pragmatic issues: that because you do not yet pass as male, queer men won’t accept you or find you attractive. In this area, I can offer you a ton of straightforward assurance:

It will be so, so fucking easy to get queer men to fuck you, dude. No matter how you look, no matter how you identify, men in general are a population that it is very easy to get the sexual and romantic attention of in plentiful quantities. The reason for this isn’t that dick is abundant and low value, as many a liberal feminist sex writer has put it, but because men have societal power that makes them more confident expressing their desire.

Unlike women, who typically fear that their sexual desires either do not matter to other people or are in some way wrong and “creepy” (and are rarely afforded the freedom to practice expressing what they want), men are societally expected to initiate with potential partners and pursue them, and that makes them refreshingly easy to negotiate a hookup or date with. In my experience, this is just as true of queer men as it is of straight ones; in fact, because the power differential between two men an isn’t so stark, it tends to be even easier for them to negotiate sex with one another than it would be for a straight man and a woman.

Until now you have been dating in the lesbian world, where both parties frequently harbor a lot of shame over their feelings and have been conditioned to not voice their attraction — so you’re gonna be shocked at just how simple securing a date (or a bang) with a guy really is. You will be drowning in options from the moment that you set up a Grindr/Scruff/Tinder/Feeld/Sniffies/Recon/etc profile, and fielding all those requests for your attention will be a great opportunity to develop self-advocacy skills for you.

At the top of this piece there is a photo of me from 2021, standing in ratty gym shorts with my shirt pulled up, revealing my still estrogen-softened tummy and obvious underboob. At that point in time I had just finished going through a months-long detransition freakout, and I looked physically quite feminine, with a round face, curvy hips, and D-cup-ish boobs. This did not stop my phone from immediately overheating and shutting down from the sheer volume of Grindr notifications I got when I created my profile and set that pic as my main photo.

There were men less than three hundred feet away in my massive apartment building pinging me that fateful evening, trying to hook up, alongside dozens of interested men and trans people from throughout the city’s north, south, west, and suburban sides. I became rapidly overwhelmed with keeping track of and responding to all of these messages (a rookie mistake, more on this later) and had to shut the app off. Once I went out into the saunas and cruisy gay bars, I was met with the same encouraging reaction: there were men staring me up and down, chatting me up, and running their hands all over my legs trying to get my attention.

Dysphoria will tell you that if your body betrays even one hint of stereotypical femininity, queer men won’t want to have anything to do with you — but your dysphoria is a liar. As a lesbian, you have probably witnessed the huge diversity of women’s sexual and romantic tastes. Give your queer brothers a little credit, too: what any random gay/bi/pan man finds appealing will differ vastly from what turns on the dude right next to him, and how each of them defines maleness and male-male attraction is incredibly idiosyncratic.

What some men find most attractive about other men are hard, pulsating cocks. You’ll be hard-pressed to get much attention from a dude like that. This is fine; you’re not going to want to get with every Daddy’s-boy and piss freak you stumble up against either. If some guy on Grindr tells you that you’re “not his thing” because you’re not 6’2’’ and covered in muscles, well, that just makes you like any other guy who sometimes gets rejected and has insecurities about his ability to live up to cartoonish standards of masculinity. Talk to your fellow queer men for a second and you’ll realize you’re all in the same spot.

Some men are attracted to masculine energy in particular, and can find it in any type of person, regardless of their physical embodiment. Lots of guys go for the boyishness of early-transition trans guys (and this can be a problem if you get into a relationship with one and your transition progresses beyond it; more on this later, too). Plenty of queer men are ardent converts to the worship of bonus hole. I can’t tell you how many bi and pansexual men I’ve met who want nothing more than to get with a lesbian-adjacent person.

And then there’s lots of men whose sexuality is more complicated that simple gender labels or stereotypes, who would have liked you under any identity and will be happy to see you grow and change on testosterone, too. These ones are real keepers. There’s also the ability to date other trans and nonbinary people that you meet in queer male spaces, too. Whenever I think that I’m the only trans guy in a gay space, or the most clockable one, I slow down, scan the bodies around me, and then I see all the top surgery scars, unbinded breasts, and trans symbol tattoos that I’ve missed. Sometimes we get so consumed in our self-consciousness that we don’t really see the people around us.

Now I can already hear the dysphoric monologues inside some of you reading this: what happened to Devon won’t happen to me. He lives in a city. He’s white and thin and passes. He doesn’t know how difficult real people actually have it. Yes, I am aware I have significant privilege within a dating market that skews fatphobic and white supremacist.

But I speak to you based on the experiences of dozens of trans masculine people that I am close with, many of them non-passing, plus-sized, darker-skinned people who do have to deal with tons of prejudice in dating…and they are also absolutely drowning in requests for attention from men. I have seen who gets play at the puppy moshes and in the darkened backrooms, and it’s trans men of every conceivable stripe. Yes, this includes people who live in rural areas and suburbs. Yes, this includes obligate tops. There are so many people who want a wide-hipped, large-chested, non-passing trans man and his pussy and/or strap dude, trust me. You are attractive. Lots of people already feel this way about you. Lots of those people are queer men.

The options are bountiful! Not all of them are good, mind you, but you sure can get a ton of experience hitting on people, turning down bad offers, and figuring out what it is that you want from putting yourself out and among them. You can begin doing so right this fucking moment! I promise!

I have already written a highly detailed guide to cruising and exploring the apps, so I will not rehash everything here, but for the newly-transitioning person in particular I have some tips:

• Be specific about what you want. Do you enjoy bottoming/topping/versing? Are you curious to try any kinks? Are you a dinner-and-drinks-for-a-first-date type of person, or do you want to throw your clothes off and leap onto the bed right now? If you haven’t been a queer man for long, you probably aren’t used to just spelling out what you are looking for. Just name some specific activities you would like to give a try. It’s okay if you are curious but uncertain. Just spell that out. Keeping your negotiations behaviorally focused works a whole lot better than trying to vaguely describe yourself or what you’re seeking long-term.

• Be direct. There is really no degree of bluntness that is “too much” on queer male apps, or in the bars. You can tell someone immediately that you think they’re hot, you like their smile, you want to get coffee with them, you want their number, you’re fantasizing about eating their asshole, or that you’re newly divorced and just want to cuddle and see where things go. Every guy is looking for something a little different, and most of them won’t be shy about saying what that is. You can do the same.

• Reject people. A lot. Because queer men are not too hesitant to shoot their shot, you will be inundated with more messages and approaches than you could ever possibly field. Do not make the rookie mistake of thinking you have to entertain any attention that is polite or validating. You can turn someone down for any reason, including temporarily while you figure out how you feel. Just say “no thank you,” or “not tonight,” and move on without apology. It shows the other guy respect and saves you both some time.

• Accept rejection with grace. I have said this before and I will say it again: being rejected does not mean that you have failed or done anything wrong. A rejection is a successful consent negotiation. That’s something to be proud of. You expressed an interest, the other person was not available for it; now you know. It is always better to have tried to make a connection happen than not, especially when you’re from a group that has been trained never to speak up, only to respond.

• Learn the etiquette & social tools of the space. I discuss this more and provide examples in my cruising guide. In a cruisy bar or sauna, it can be expected that an interested man might put his hand on you. Be prepared to handle this, and know you can rebuff him by taking his hand off your body or just walking away. On the cruising apps, a lack of reply is not “rude” nor is it “ghosting,”; it just means the other person is busy or not interested right now, and you’re free to hit them up again pretty much as often as you like to see if anything clicks. A block just means you’re incompatible, and the other person doesn’t want to waste anyone’s time with you appearing on their feed. Do some research, observe others, and understand that these social rules are just tools you can use, like mechanics in a video game, to get what you need.

It may take a moment to get used to the social norms of queer male dating if you’ve used to high-context, interpersonally rich lesbian dating in all its sensitivity and emotiveness. But generally speaking, the biggest mindfuck will be just how obvious everything is. If a guy is not into you, he will pointedly look away from you; if he is really feeling you, he will pursue you and not hide it behind compliments about your outfit. And when you hit on a guy yourself (which you absolutely should do), he’s generally not gonna waste too much time on being polite.

You’re also likely to find that men will absolutely melt over your listening skills and emotional intelligence. Though some queer men are comfortable with a tiny bit of femininity in their dress or voice, a lot of them still aren’t used to exchanging very much real tenderness, so you might find that what feel like basic dating courtesies from you can make a guy go completely head-over-heels with love. You’re not failing to pass or being “female socialized”; you’re just the nicest possible guy friend, and it makes dating you an absolute prize.

If you have even remotely developed social or relational skills, you may actually find you have the upper hand in dating queer men. Enjoy this soft form of power if you have it, and use it to your advantage! Any partner worth your time will be grateful for your communication abilities and processing skills.

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A post shared by @devinglass_

Now, there are some pitfalls specific to being a newly-transitioning guy entering gay male spaces. One of them that I would like to highlight is the risk of falling in with the Opportunistic T-Boy Chaser.

The Opportunity T-Boy Chaser is a man who finds newly-out trans boys (as he invariably calls them) attractive because he perceives them as feminine, youthful, horny, and sexually available, who will not remain interested once the trans boy becomes confident enough to integrate himself into queer male communities or transitions into visible manhood.

Guys like this prey on the insecure and socially isolate them; in a relationship, they will guilt, pressure, mope, and manipulate their partners into lowering their testosterone doses, delaying surgeries, and remaining hairless “femboys” forever. Dating the Opportunistic T-Boy Chaser promises a life of slow recloseting and mounting dysphoria. Here are some warning signs:

Red Flags for the Opportunistic T-Boy Chaser:

• He doesn’t have a lot of gay or queer male friends.

• He mostly dated cisgender women until he “discovered” t-boys.

• He predominately dates t-boys significantly younger and/or less socially powerful than him.

• He’s insecure about being emasculated.

• He is afraid of being seen as gay or queer by other people.

• He is obsessed with talking about the trans boy’s changing body in a fetishistic, infantilizing way, but finds actual masculinity unattractive.

To be clear, there is nothing wrong with a guy being attracted to visibly transitioning or androgynous people. And it can be a lot of fun to hook up with someone for whom you are the ideal physical type. What’s most troubling here is the overall pattern of seeing young trans men as a sexual resource that’s easier to access than cisgender women. The Opportunistic T-Boy Chaser is not some bisexual guy who happens to like guys who are short, or a pansexual who doesn’t care about a partner’s identity; he’s typically a straight man who sees a transmasculine person as a woman he does not have to buy dinner for. If a guy is proudly, comfortably in community with lots of queer individuals, and he has dated widely, he is not that type of guy.

There’s also the matter of dating chasers more generally. I consider myself chaser-neutral; they’re an inevitable part of the dating market that can be pleasant or unpleasant to deal with depending on how informed and considerate they are. Some chasers put their preferences out in the open, saying that they’re looking for women, femmes, and transes right on their profiles.

I actually do not have any problem with this. As an effeminate trans guy who wears his submissiveness on his sleeve I’m a proud member of the faggot subaltern, and it doesn’t surprise me that the types of people who are attracted to me are looking for both feminine men and women. If you’re not selling what these guys are shopping for, you probably do not want to date them, but that doesn’t make them a universally bad fit.

There are trans-chasers out there who view us as less than human, and who revile us and the attraction that they feel toward us, and that attitude manifests in sexual exploitation and violence (most often directed at Black trans femmes). But there are also just people who find something about trans people captivating for no reason they can pinpoint, and some of them put a ton of work into learning correct terminology and sexual techniques, and will fawn over us like we’re living angels.

I’ve been on a few dates with guys of the latter sort; they’ve looked at me all dreamy-eyed, picked up the tab, and held my hand while whispering they couldn’t believe someone like me was real. Some might find it othering to receive such heightened attention, but what can I say, I like to be special. If you’re proud of your transness, then another person being attracted to trans people won’t always register as a suspicious thing. But it’s okay if you want to guard yourself. There’s a lot of bad behavior and abuse of power out there.

I think the discussion about chasers naturally invites a discussion about the practicalities of navigating sex and dating while your own relationship to your body shifts. How you look right now is probably not how you will look two or three years on T; ten years from now you will be a completely different person in all kinds of ways, many of them completely unrelated to being trans. There are not simple tips for coping with this; I think it all relies upon self-knowledge, communication, and a capacity to be surprised.

Check in with your body a lot. Observe what actually feels good to you in the moment, doing your best to abandon previous expectations or narratives. Prospective partners will make the wrong assumptions about you, often based on transphobia and misogyny, but sometimes you’ll also apply stereotypes unfairly to yourself.

It can be maddening to work for years to figure out what give you pleasure, only to find out later that it has changed. But this is a common part of the queer life cycle. You can transform from a pleasure top to a stone bottom over the course of your transition, move in time from otter to popper pig to bear. Who knows why these things happen; they’re not just a byproduct of hormones, but also influenced by cultural movement, experience, and age. Keep an open mind with yourself but firm boundaries with everyone else. Let yourself be pleasantly surprised by the man that you become.

Most of the remaining advice that I have to give pertains to dating men for the first time in general: keep yourself as safe as you can. Give your date’s number and address to a friend before you go out; take PrEP (to prevent HIV) and Doxy PEP (to prevent gonorrhea and chlamydia), get your HPV shots, get tested regularly, and don’t beat yourself up when a virus does happen, as they sometimes do.

Inform yourself of the dangers of sexual and kinky activities, and only agree to do things you’d be happy to incur some risk for. If you feel on the fence about a dude, or an activity, that probably means it’s a no (or at least a no for now). If you keep arguing with yourself about why you should stop being so judgmental and just give a guy a chance, it’s a no. Letting the other guy host the hookup is generally safer. They can’t rob your house or stalk you if they don’t know where you live, and very few people are willing to leave the evidence of a violent crime all over their own homes.

Public hookups are safer than private ones, contrary to popular belief (and heterosexual fear-mongering). Bring a buddy with you to the sauna or the cruising spot the first time, and say hello to the staff. These spaces are precious to a great many people, and they will step up if someone is threatening to ruin them.

Two Black men embracing. Photo by Lloyd Jr. on Unsplash.

Beyond that, just remember that queer men are just like you — haunted by repression and trauma, dogged by the fear they are not doing manhood correctly, horny and confused and scared and desperate to be loved. As you progress in your transition, you will find a growing commonality with queer men that transcends any sexual or romantic connection; getting close to them will help you better understand the kind of man that you are, and growth into your own transmasculinity will help them better accept who they are, too.

Have fun!

You can submit questions or suggest future entries in the series via my Tumblr ask box, or you can email questions to askdevonprice at gmail.