To celebrate Valentines Day, Them is diving deep into queer sex, love, and relationships all week long. Read more here.
When I open hookup apps like Scruff or Grindr, I often feel like I’m walking to school in my neighborhood growing up. I lived in the areas of Brooklyn and Queens that artists like Notorious B.I.G. and Nas wrote about, during the time when their classics were first released. I wasn’t into hip-hop back then, though; I was a punk, and it felt like everyone on the street commented on my style of dress either because it was so different from the prevailing culture, or because they didn’t understand why such a cute young woman would choose to dress so butch. Looking back, I get that it came from a heritage of oppression and scarcity. Othering me was a backwards way of guarding community integrity. In any event, all the street chatter eventually just became irrelevant stuff I learned to tune out.
Years later, I’m tuning out different chatter, and facing a similar mix of misconceptions, othering, and protectiveness, from guys on the apps. This is not another piece about how terrible the apps are. We know they’re chaotic. I do have good experiences off the apps, and I’m gonna talk about them, but after 18 years of medical transition, and so many iterations of myself, it does bear stating why and how messages like “so ur a woman?” or “I wanna fuck some pussy” feel basic, irrelevant, and draining.
Apps like Grindr squeeze us into “tribes” (e.g. trans, twink, bear). The unspoken characterization of queer trans men is a naïve, hairless, young, white twink bottom, post-operative above the waist, and non-op below. Most popular media around transmasc culture centers on medical transition itself, on the shifts involved in going from being perceived female to finally being perceived male, so it’s not surprising to me that we are often thought of within gay culture as perennial boys, as Man Lite™️. While some of us do fit that perception, stereotypes and gender essentialism contribute to well-meaning cis men relaying sweet but underhanded sentiments such as “I’m gay, but I love trans men,” or using phrases like ”gay men and trans men,” as though the only way to truly be a gay man is by either being or fucking a cis gay man.
I mention all of this because it’s the terrain that queer trans men and trans masculine people must navigate in order to attempt to connect within gay male culture. I first dealt with this by being a “pick-me” boy, back in my mid twenties. Starting testosterone had immensely boosted my need for sex, but I didn’t yet have the confidence to consistently ask for what I wanted. Bad or unfulfilling encounters were better, I thought, than no sex at all, although I did get what I wanted some of the time.
I feel lucky that my first online hookups were back before Craigslist NYC removed their personals section due to the passage of FOSTA-SESTA, restrictive federal legislation that has had disastrous consequences for LGBTQ+ people and sex workers. The listings back then were buck wild, and had a touch of the nonchalant, unpredictable spirit of in-person cruising, because people advertised what they wanted to do as opposed to who they are, as you do on the current apps. In that arena, even at the beginning of transition when I was most insecure, I still got to have exactly what I wanted sometimes.
One of my first gay hook-ups was a muscled, red-haired chef with a chonker of a Prince Albert piercing. We got together a few times at an hourly hotel in Chelsea. Having gay sex with him was like being cast in the mid-aughts porn DVDs I watched at the time, a fantasy I never anticipated coming true. Likewise, by advertising for specifically what I wanted on CL, I found a very hot bear who would give me spectacular head for hours at a time, and who I’m still in touch with after a decade or so. As a matter of fact, we’re overdue for a session.
With time, many, many, sexual partners, and heaps of rejection, I learned that trying to completely assimilate into cis gay culture, and prioritizing others’ expectations didn’t garner much lasting reward or get me closer to my wants. I eventually understood that my body is not something I need to “make up for.” My body is not a cis body and it never has to be. Eschewing assimilation, I gave myself permission to integrate into gay culture, while still honoring my experience and context. I eventually realized that even though I happen to enjoy the physical sensation of bottoming, the almost ubiquitous presumption that being a trans man automatically makes me a bottom feels emasculating. Furthermore, the all-too-common conflation of topping and dominance feels lazy and misogynistic. It’s all such a turn-off that these days I really can’t prioritize receiving penetration. The moment I started indicating things like “Seeking oral subs. Kink & head only. Keyholder. Fisting top” on my bios, I went from receiving a dozen or so messages a day from guys looking to fill my hole, to about one or two messages a day, mostly from kinky bros and submissives. I’m not mad about it.
While I’ve developed a love for cruising gay bars and sex parties over the years, I’ve never preferred geolocation as a way of finding sexual partners. Proximity counts, but I’m likely a lot more compatible with a guy I meet inside a leather bar than I am with a guy who just happens to live near one. It is very worth saying, however, that I’ve met some of my most beloved play partners and submissives off the apps. Just as I’ve met some guys more organically, I’ve also had some truly memorable interactions with trans and cis men from the apps, regardless of whether those times were ephemeral or longer term, or whether we even still know each other.
Compatibility is a numbers game, and if nothing else, gay hookup apps are a beacon letting every other app user in my vicinity know that I exist. I’m a Latino over 40, and a leather Dominant who most enjoys topping for oral, BDSM, and chastity play. Just as with the rest of life (especially as a trans person), the odds are high that most of what’s out there doesn’t apply to me, regardless of being part of a community.
My current outlook is to focus, pushing past the disappointing and irrelevant messages, to find the abundance that can come from the right connections, rather than lingering on the scarcity of them being so infrequent. That is a constant effort, though, which takes a lifetime’s worth of self-assurance, a monumental amount of curiosity, as well as the truly epic tenacity that I believe all trans people share.
Get the best of what’s queer. Sign up for Them’s weekly newsletter here.
