For anonymity I have obviously changed his name.
On David
Thursday, August 22nd
10:36 AM
I talked to David yesterday for the first time in two weeks. He hadn’t reached out after agreeing to FaceTime one morning while I was in Norway and he was in San Francisco. We finally FaceTimed last night. I held my emotions in and basked in the instantaneous rekindling of our chemistry. Sometimes I feel guilty for feeling emotional. We agreed to think less and just enjoy each other.
At the end of the call, with only a minute to spare, I confessed that I missed him—a lot. He didn’t say it back. Instead, he offered to “maybe get dinner sometime” when I’m back. Struggling to hold back, I fumbled my words and said goodbye.
First Date
Wednesday, June 12th
8:00 PM | Drinks at The Narrows
From his profile, I could tell he had great taste. The way his photos captured him holding wine at a wedding in Italy, the cut of his trousers, and the color schemes of his outfits—all validated by a review from a friend in his bio that read, “He’s got great pants.”
I constantly joke about how hard it is to date men with style, let alone meet a man with aesthetic sensibilities who doesn’t weaponize it. So you can imagine how nervous I was to make a fashionable first impression. Clothes are strewn everywhere as I FaceTime several friends in an attempt to curate an outfit that conveys my personality while adhering to the tragedy of participating in heteronormative society as a woman. There’s a nuanced balance to looking hot but still respectable but not too respectable then he wont want to fuck you or you don’t look respectable enough because then he will only fuck you. Sometimes serving cunt isn’t the answer. My gays didn’t get it, but my girls did.
I arrive on time, and he’s roughly 10 minutes late (punctuality in New York is dead). We exchange our first hug. He smells amazing. Neither of us has eaten dinner, but we play the coy game of not committing to a meal. Unfortunately, we skip the Tuesday night patty melt special as he opts for four drinks throughout the evening while I—without even noticing—nurse an IPA for the entire three hours.
Somewhere in between the classic from New York, “Where’d you go to high school?” and the mutually masturbatory, “Oh, I was also just in Paris…” I asked him if he’d ever been with a trans person before. His casual, “Nope." leads me to my follow up, “Have you ever thought about it?” met with another nonchalant, “Nope”. He tells me it wasn’t till after we matched he read that I am transgender. He said it didn’t really matter to him. He just thought I was pretty.
Now both pleasantly buzzed and booked with morning obligations, we call it. While I’m waiting outside for my Uber, we share a cigarette and as I’m about to get into the car, he grabs my lower back and pulls me into a deep and confident kiss. You know the kinda smooch you have when sparks fly on a first date.
I was left with three main takeaways from our successful first date:
After a six-year relationship and two years out of it, he is finally ready and yearning to be in a relationship again. If you’re dating in New York right now, you know how rare it is to find a man who’s emotionally available, let alone one who wants to cultivate a relationship—shockingly enough a monogamous one.
I’m not ready to meet the man I want to marry. I’m only now two years into my transition. I’m still evolving. I’m still getting hotter.
He has three credentials that he looks for in a partner:
A mutual desire to spend time with one another.
A mutual desire to fuck one another.
Someone who knows what he’s talking about.
The last one I’ve been chewing on for months.
There came a point in my marathon sprint of heteronormative dating when I accepted that men do not understand women, especially queer women. I have felt like a spectacle, an anomaly, or a novelty to the men I’ve dated. Many have been terrified of what they perceive my reality to be, horrified that participating in my world might lead to social ridicule or shame—for what? Being straight? They’re not even sure, but the perceived dangers illustrated by our digital cultural divide are too great to risk.
Second Date
Thursday, June 20th
6:45 PM | Night Picnic at McGolrick Park
This is a date I have had in my back pocket for ages. If you’ve ever been to McGorlick Park at night, it’s a dream. The warm lampposts, the trees consumed by the night, and the glow from the surrounding houses bordering the park make it feel magically vast. It feels like you’ve entered a completely new environment, distant and almost untouched by the electricity of the city. I’ve tried dangling an evening wine picnic in front of a few situationships, but the pressure of developing any sort of intimacy is just too overwhelming and unfortunately perceived as inappropriate or cringe to even suggest. Of course, David doesn’t hesitate.
We planned to meet a few hours before sundown. My hair’s got perfect beach waves after spending the day at Jacob Riis, I’m hopped up on the 60 cal berry flavored Yerba Mate, and my tote bag is packed with supplies to set the mood. Two CB2 wine glasses from my apartment, tea lights in red glass holders, a speaker to play my go-to “sultry jazz” playlist, my roommate’s woven picnic blanket, and a bottle of natural orange wine. Setting a mood is imperative. I love the fantasia.
Of course, as soon as I plop down on a bench, exhausted after a crazed marathon to get ready for the date, pick up a bottle of wine, and maintain an effortless chill-girl aura (lmao), I accidentally sit on a wine glass, and it shatters in the bag. My fault, honestly, for throwing a wine glass casually into my roommate’s Muji tote bag (Allison left it when she moved to El Paso—lemme know if you want it back). I grab plastic cups frantically from the grocery store by the grace of his tardiness, and we find a grassy spot to post up.
Even before we polish off the bottle, our rapport is effortless. We both express that we’re doing our best not to overthink and just sink into how much we enjoy each other. Night falls, the bottle is polished off, and we’re chain-smoking Marlboro reds to what is now the well ran through playlist into a jazz radio. The vibe I have curated is now at the whim of my Spotify algorithm. Luckily, we’re completely unfazed by the occasional ambient boner killer spurting from my speaker. We went from Lester Young and Stan Getz to a bastardized sort of lo-fi hip hop beats to study to.
Reach over, change the playlist, and I decide it’s time to saddle up. My legs wrapped around his torso as he lifts me onto his lap. His hands discover the small of my back, the nape of my neck, and, of course, delicate slap on my ass. In the heat of it I feel his excitement. Suddenly self conscious, I angle myself to make sure he can’t feel my excitement. With the sudden awareness of my body and our mutual agreement to return to decorum, I dismount.
Sitting up on my elbows with my legs still tangled in his, he feels the shift in the air. I tell him about how I’m nervous he will be repulsed by my body—that no matter how slow we go, he will be uncomfortable with my genitals. Without skipping a beat, he jumps in to assuage my anxiety. He convinces me that he’s not afraid of me. In an attempt to prove it, he explains he’s seen another penis in a group sex setting. He’s never touched one, and the idea of it doesn’t arouse him, but it doesn’t scare him. He assures me he finds me desirable and that he wants me. He wants to learn for me.
We end our five-and-a-half-hour wine picnic with a few more passionate kisses, smoke one more cigarette, and he walks me home. On the walk home, we plan our third date, and he kisses me goodbye at my door. Another classic goodbye smooch.
Third Date
Monday, July 1st
6:00 PM | Watch the Sunset in Sunset Park
By now, I was crushing.
I’m on my way to meet him for dinner and to watch the sunset in his neighborhood. We barely text (he redefines bad texter), and that only fuels my yearning. I want to see him bad.
I’m waiting outside the Japanese market in Sunset Park, pretending to smoke a cigarette. I don’t like using my phone to look busy or kill time. I have my umbrella in one hand and Marlboro Gold in the other, but in my mind, my hands are pressed together and praying to God the humidity doesn’t make my hair too frizzy. The relief I feel when I see David sauntering over from down the street frustrates me. I hate having a crush. I hate feeling powerless.
During dinner he eagerly shows me the fits he has for his friend’s wedding in August. He prefaces it with, “People love it or hate it... wait for it…” I tell him how I love when people say they wanna show you something on their phone and you’re waiting begrudgingly for them to pull it up. My rule is if you can’t find it in 15 seconds you have to show me later. He then turns the phone to me and says, “Shorts.” The image is him in an all-black suit with what looks like formal shorts. He swipes to the next image, and it’s basically the exact same suit but in a chocolate linen brown. I know I’m biased because I like him so much, but I really do think he’s selling it. It kinda really does look chic.
This leads to an invigorating conversation bitching about how New York has changed. We both resent the downtown “scene” where we have overlap. There’s a tension in the city now. People seem to be fantasizing about having fun more than actually having it. Authenticity is both the hottest trend and the hardest thing to find. It’s uninspiring. Theater is dead.
We finish dinner, and he takes me to the literal Sunset Park, where at the top of the grassy hill you can see one of the best sunsets in New York. The rain has just subsided and all the benches are freshly wet. He wipes the bench with his jacket for me. There’s a group of elderly people doing tai chi behind us, a pregnant woman and her husband playing frisbee with their son, and a few other couples on scattered benches.
He tells me about a friend of a friend who has the worst luck with dating in New York. Apparently, she went on a third date with this wonderful guy, and after he put her in a cab home, he ghosted her. For two weeks, she agonized in confusion. Turns out, right after he put her in the cab, he had a psychotic break and woke up naked in Jersey a few days later. He’d been in recovery since.
I told him the view of the East River with the spire of the church in focus reminded me of Venice. We now call the East River “The Lagoon.”
Post sunset make out, we begin the walk back to his apartment. He points out all his local spots. We hit a bodega to grab some beer, and I offer to pay. I’m a firm believer in men paying for the dates (desire is expensive) but occasionally to prove my appreciation, every now and then I’ll offer to get the coffee or, in this case, the six-pack. They think it’s cute. I can tell he’s become buddy’s with the owner. Lost somewhere in their banter I misunderstood the cashier. I thought he was giving me a discount cause they’re buddies but when he said he only gives discounts for “the boys.” I didn’t realize he literally rescanned the beer and made me pay full price. Honestly, got my ass good.
I told David I have a vivid image of what I think his apartment looks like. I tell him it’s minimal but has soulful. I guess he has some sort of elevated Matin Lamp with a well-designed calendar. I knew I was right on the money when his eyes widened with surprise after I guessed his books were on the floor.
We make it back to his place. He just got a bookshelf to pick his books up off the floor the day before, and he has a literal blue Matin lamp on his desk with various well-designed posters. I’m surprised to see various signs that he’s a weeb (manga and such). Humanizing, in my opinion.
Our first heavy public make out on the second date proved to be a restrained prelude for the sexual chemistry we discovered in private. It gave him my non-verbal consent to throw me around the room like his little rag doll.
There’s something about the look in his eyes when he breaks away from a kiss. How he looms on top of me, holding my throat while scanning my face and body with this almost smug little smirk. Like he’s proud of himself. Drives me absolutely crazy.
Finally released from his grip, I sit him on the edge of the bed. Being on my knees is more comfortable. I like to enjoy myself. To be brutally honest, sucking his dick evoked the same rush I felt in 2019 when I hooked up with my ex in my painting studio at Carnegie Mellon. To spare you, we both basically blacked out while he played around in my throat for roughly 45 minutes to an hour. We only came to when I suddenly realized my jaw was in incredible pain and the sheets were soaked with my throat slime.
Dislodging his cock from my throat, he steps back and slips backward. The hardwood floor by his bed has a massive slick puddle from my throat. I want to be clear—this isn’t a brag; my mouth just does this. Like Pavlov’s tranny, my mouth salivates when the bell rings. However, the volume and viscosity was so destructive he had to immediately change his sheets and wipe up the floor. He politely asked if next time I could not make such a mess. “I have to spit it out or I will drown!”
We proceed to sit on his fire escape to have a cigarette. I felt uneasy. Our first sexual act was extremely intense. It’s not that it was rough. Losing ourselves in each other at such an early stage of our relationship can me intimidating. Especially when neither of us came. I didn’t know how I felt. I wasn’t ready for that level of vulnerability. Hell, I had to take off my clip-on bangs—that’s not something I do around men I like!
He held me on the fire escape. He was very tender toward my insecurities. We spent the next few hours talking while he chain smoked. I don’t think I’ve met a pack a day smoker since I was twelve.
Usually, when I share a bed with a man for the first time, I get night terrors about him, so I decided to go home. He called me an Uber from Sunset Park back to East Williamsburg. I bumped into his roommate on my way out. I’m sure my smeared makeup, swollen lips, and matted wet disaster of hair pathetically contained in a claw clip made a great first impression.