earnest shitposter

I’ve had it since I was a man (pictured above) and it became a staple of my wardrobe for many social events. I wore it the night of my 21st birthday to a gay bar in Seattle with my friend Monty. He’d later become my best friend, but at this point we’d only met once before. The night of my birthday we parked and did a shot of vodka in his car before going inside (to save on drinks). Monty had been seeing this guy AJ for a while and I thought they were both very cute so I said “before I get inebriated, I just want you to know that if this night ends with a three-way between you, me and AJ I’m totally fine with that” he agreed, we toasted with another shot, and entered the club.

My first night as an out and proud adult in a gay bar was formative for me. I saw some incredibly fierce drag queens perform, I made out with lots of men (and one woman) on the dance floor, and I got absolutely wasted for the first time in public. It was magnificent. It’s a shame that bar isn’t there any more.

After we’d danced the night away, we went back to AJ’s apartment and started getting frisky in the boudoir. We’re all going hot and heavy, making out when Monty falls asleep. AJ and I looked at each other and rolled him over and carried on right next to his unconscious body.

Fast forward a few years.

That story has become a defining moment of our friendship since we reconnected a few years later. While we were reminiscing about it the other day I found some pictures from that night and said “oh my god! I still have that romper too!” Monty was thrilled, he said I had to wear it to his birthday party. The theme was “The Eras Party” dress as yourself from your fiercest era— past, present, or future. I’d been thinking of a suitable outfit for weeks with no ideas. Yeah, I had this romper in my back pocket, but I no longer felt like it represented my fiercest era. It felt like one so far gone I hardly recognized.

I tend to get very insecure about how I’m perceived in my own community. It all seemed so much easier when I “was” a “gay man.” The more feminine my presence becomes, the more it feels like the gay men I’ve loved for so long are losing interest. And can I blame them? Their whole lives they’ve been fighting for right to love the *men* they’re attracted to, and at what point does that no longer include me? I could never imagine myself pursuing a straight man, nor could I imagine one pursuing me. I constantly feel too feminine for the gay boys and too masculine for the straight ones. It’s an alienating feeling. At what point do I cross the threshold from gay man to trans woman? Short answer: the threshold doesn’t exist. Or maybe it could if I wanted it too. If I asked for a feminine name and pronouns tomorrow, I think people would have a much easier time understanding that! But that’s not what I want. I want to be feminine, sure, but it isn’t so clean cut as “gay man” OR “trans woman.” This must be why I prefer “queer” and “faggot” over any other identity labels. My white-whale romantic partner is someone who’s not only okay with, but actively celebrates my queerness in all its shapes.

Then it hit me. The party. I could add a new twist to a classic Miles outfit! Keep the romper, but add the orange crop that shows off my small but growing tits!! Drop the shoulder, and add feminine accessories!!! Style my hair in a fun side-pony!!!! Now we have a flirty look that takes the best qualities of my past and points them toward the future. It’s a little cheesy, and a lot of fuss to make over an outfit for a single party, but this is a meaningful moment for me as my ever-fluid gender expression continues to change.

I sometimes grieve the loss of the handsome man in that picture. I wonder if I should have tried harder to find happiness as I was instead of changing. Moments like this remind me I am not losing any part of myself to pursue happiness. I don’t have to give up the things that made me happy before. I can still be the gay man I’ve always been, and then some.