It wasn’t even supposed to happen. My next trip to New York wasn’t booked until February, and that seemed eons away. When the cute nerd from New York slid into my DMs after some back-and-forth flirty tweets and asked if I’d ever want to “meet a Twitter admirer in person over coffee or something,” I thought it’d either happen months from then or not at all. But it was a nice fantasy, for a moment. “Eee, a Twitter dude is flirting with me,” I texted my best friend, and I kind of thought that’d be the end of it.
But then pieces fell into place – it’s a long story involving a sugar daddy, a plane ticket, and an unexpected break-up – and I found myself going to New York in mid-December instead. By that time I had almost forgotten about the cute boy in my DMs, until one night when I pondered the trip ahead and made an impulsive decision. “Hi! I’m gonna be in NY from Tuesday to Friday next week,” I tapped out. “My schedule’s a little packed and it’s kind of a last-minute trip, so I’m not sure if I’ll be able to squeeze in coffee with you, but I’d like to if we can make it work!”
“Hi! I’d like that too,” he wrote back, and we picked a time and place.
The day came. I wasn’t thinking about our date much. I wasn’t even sure it was a date. I had plans for later that day to get on a train to Long Island and go do a pre-negotiated knifeplay scene with a beau, so this coffee with my “Twitter admirer” was just a fun diversion to fill the remaining time until then. My only expectations were good espresso and maybe good conversation. That’s how you should go into every date, really: expecting nothing, so if anything the slightest bit lovely happens, it’ll be an unforeseen treat.
I walked into Culture Espresso on 38th at the appointed time and spotted him immediately: this blue-eyed boy in a blue button-down in front of blue floral wallpaper. He was a vision from the first. I wasn’t expecting that, somehow, even though his big blue eyes in his Twitter avatar were half the reason I’d tweet-flirted with him in the first place. He was cute in the way that usually makes me write someone off, like: There’s no way he’d be interested in me. But he was. He’d asked me out. I didn’t know what to make of that.
“Hi! Can I buy you a coffee?” he asked, bright and extroverted. I declined, wanting to buy my own drink, because paying my own way on a date makes me feel strong and independent and like I don’t owe anyone anything. He told me later this threw him for a loop, made him wonder if I was indeed viewing this as a date – but he recovered well.
I sat down with my latte and we asked each other about our work, our non-monogamy situations, our favorite musicals. (His was Sweeney Todd. I was immediately more interested in him. And I was already pretty interested in him.) I told him about a story I was working on at the time, about unrealistic sexual expectations; when I said “Lots of guys think they can make a woman come from PIV alone,” he rolled his eyes exaggeratedly and that was the first moment I thought, Yeah, I’d like to fuck this person.
“Do people ever make false assumptions about you because you’re poly?” I asked at some point, fascinated. He’d been non-monogamous for years longer than I had, so I went into journalist mode, probing him for wisdom. He pondered that and said, “Totally. People often assume I’m not serious about the people I date. But I’m very serious about the people I date.” A shiver went through me, a quiet premonition that maybe he could be serious like that about me someday. It wasn’t a “chill” thing to say on a first date, but I’m the least chill person I know, so I wasn’t put off – just intrigued.
At one point, he asked me, “Do you think kink is an orientation?” and I brightened even further at the sex-nerdiness of the question. “I think it is for some people. I think it is for me,” I told him. “I’m a submissively oriented person, and I tend to be attracted to dominant, masculine folks, regardless of gender.” His face remained carefully neutral. I wondered if his ears had perked up, somewhere in there, but I wasn’t sure.
We made each other laugh. We shared a chocolate chip cookie. We traded phones to look at each other’s podcasts. He stared into my eyes with such intensity and depth that sometimes I lost my train of thought completely and could only spout excuses: “I’m sorry, you’re just really, really cute.” He smiled opaquely, politely; I couldn’t tell how he was feeling, only knew how I was feeling. I was feeling a lot.
After about an hour, he asked, “Have you eaten? Do you want to go somewhere else?”
I looked out the window at the bitter wintry urban landscape and mused, “If it were summer, I’d say we should go make out in an alley, but it’s pretty cold out there, so.” I have no idea what possessed me to say this. This is the type of line I might bust out if I was 110% certain someone wanted to kiss me, but in this case I wasn’t. I wanted to gauge his interest, and didn’t have much to lose – we didn’t even live in the same city, after all.
This dare of sorts worked as well as I could’ve hoped, however. “That’s a solvable problem,” he said, without missing a beat, and pulled out his phone.
There is an app called Breather, where you can rent nearby office spaces by the hour for meetings, presentations, and work sessions. Not for makeouts, you understand. That is explicitly against the terms of service. But we are rebels.
As he explained his plan to me, he scrolled through the available spaces, picked one, and showed it to me. He titled our reservation “Important Meeting” and leaned across the table and into my personal space to show me the briefcase emoji he had included. I wanted to kiss him right there, but knew it would be better to wait.
We trekked out into the cold and he led me down blustery city streets toward our “meeting” space. “Your shoes are so shiny,” I commented mindlessly, having no idea I was foreshadowing sext-a-thons about shining and licking his boots that would come weeks later. “Thanks,” he replied with a roguish smile. I wanted him to take my hand and lead me where we were going. I was vaguely aware I was following a near-stranger through the streets of a city I barely knew, and that maybe this was ill-advised, but I wanted the warm kisses I was pretty sure awaited me at the end of this chilly journey.
When we got to the building, he greeted the receptionist with more charismatic confidence than I have ever had in my life. As we rode the elevator to the 10th floor, I asked him, “They 100% know what we’re doing here, right?” and he said, “Oh yeah, totally.” I wanted him to push me against the elevator wall and kiss me hard. I wanted some tangible sign he wanted me as much as I wanted him in that moment. I would have to wait.
We were slightly early for our booked timeslot, and someone else was still using the room, so we waited outside. I leaned against the wall and focused on his beautiful face, to the exclusion of all else. “I’m trying to figure out what celebrity you remind me of,” I murmured. He smiled and stared into my soul with those deep blue eyes. Later I would realize it was Cillian Murphy he reminded me of. Um, the boy is very fucking good-looking. Have I mentioned?
When the room freed up, we walked in and took a look around. Ample natural light flowed in the windows. We plugged in our phones. I took some pictures. We busied ourselves with these things for the minute it took us to gather our courage to do what we had come there to do.
I was mid-sentence the first time he kissed me. Neither of us remember what I was saying. He just walked up to me in the middle of that minimalist room, put his hands on my waist, and pulled me toward him. It knocked the words out of me. Our faces were still cold from the winter wind and our noses were running a little and I wanted more of him, more, more, more.
So I told him to sit on the plush grey couch on the far wall, and I straddled him. I like this position for enthusiastic makeouts because, as per Gala Darling, “this way they are [consensually] TRAPPED and can’t escape until my lips are satisfied! I am sneaky like that.”
I leaned into him for long, hot kisses, feeling his body pinned beneath me and his big warm hands traversing my hips and my thighs and my ass. It occurred to me suddenly that I was tugging on his hair without having asked first, and that might be a problem for when he headed back into work after our date; I leaned back and said, “I’m messing up your hair; is that okay?” and he shot back, with a wry smirk, “As long as you put it back after.” We kissed some more and I felt his tongue slide against mine as his stubble scraped my chin.
In a sudden shift of power, he grabbed my wrists and grasped them together behind my back, so I was writhing above him but in a much more submissive manner than I had been a moment before. “Are you a little dommy?” I asked, tentatively, having theretofore assumed he was on the vanilla side of the spectrum. “I’m a switch,” he responded, with the well-worn ease of an actual kinkster, and excitement sparked inside me even further. “I think I want you on top of me,” I breathed.
We shifted; I laid on my back on that beautifully-lit sofa and he climbed on top of me, staking out a spot between my legs with no tact or pretense whatsoever, just pushing my thighs apart with his slim hips. He ground into me through our layers of clothing and kissed me roughly, animalistically, all-consumingly. “You can bite me, if you want,” I offered, shyly, and showed him where. He bit me hard until I moaned, and made me take it. “Good girl,” he purred against my mouth, and I laughed and said, “You’ve done your research!” He flashed me that disarming grin and said, “Maybe,” before giving me his lips again.
Suddenly, we heard what sounded like urgent knocking at the door. He bolted and, in a moment, was sitting on the opposite side of the couch, smoothing his hair and attempting to regulate his breathing, like a dishevelled businessman whose boss just walked in on him with his secretary. After all, making out in a Breather is against the terms of service. A few moments’ hard listening sufficiently convinced us it was just some construction workers hammering across the hall. When he crawled back over to me and took my face in his hands again, I managed to mumble between kisses, “It makes sense, because you make my heart… hammer.” He laughed. I was so, so happy that he laughed.
He wrapped his arms around me and dipped me in a deep kiss, and for a terrifying moment, I thought I was going to fall. “Don’t drop me!” I squeaked, and he held me firmly and said, “I won’t. I promise. I’ve got you.” It felt good to hear that then; it felt even better to hear it weeks later, when, on difficult days, he would text me things like, “Remember our first date when I told you ‘I’ve got you’? I meant it then. I mean it now.”
His hand kept grazing my ass like he wanted to hit me, but he bit his lip and looked past me at the paper-thin walls through which spankings could probably be heard. “I wish we could be louder right now,” he growled ruefully, and I said, “You know what’s quieter than slapping? Punching…” And that is how I ended up stretched over his lap with my ass in the air.
He pounded his fist against my ass, over and over, making me mewl and moan into the arm of the sofa. I writhed against his hard cock, both of us still fully clothed, deliciously so. He volleyed a steady stream of affirming dirty-talk about what a good girl I was, how well I was taking the pain, how much he liked the noises I was making. “You’re so hot like this,” he said, and I still couldn’t believe he really thought so.
“Is this okay?” he asked at some point, and I melted even further and made happy, positive noises. “So then I guess this is probably okay too?” he added, as his fingertips dipped between my thighs and found my clit through my leggings and underwear. As he circled it and made me moan, he commented on how wet and hot I was, and it seemed ridiculous he could feel that through all those layers – and yet I believed it. This boy had rendered me a puddle of arousal and submission, seemingly without even trying.
We didn’t go any further than that. I’d wondered if we might, but somewhere amid all those blurry kisses, he told me he had to get back to work. People would be wondering where he’d gone. It’s not often someone just disappears on their lunch break. And I had to be getting to my train.
We gathered our things, walked down the hall, and got back into the elevator. This time, he did kiss me. He pressed me into the wall and I could feel every contour of that warm, lanky body I longed to see more of. As he snaked a thigh between mine, I worried I’d get his jeans wet. I was that unraveled, that shocked into my body.
The elevator stopped and some strangers got on, some well-to-do businessmen talking about taxes or sports or god knows what, and we jumped apart and stood silently side-by-side, our hearts thumping, our molecules mingling. We reached the ground floor and stumbled out into the harsh winter sunshine together, dazzled, disoriented. “Will you walk me to where I’m going?” I asked. Google Maps could’ve helped me, but I wanted more of this boy. Just a few minutes more. Or whatever I could get.
He said yes. We weaved through city streets together looking for the store where my best friend Bex works; he was going to drop me off there so Bex could walk me to my train. “I feel weird,” I commented, all light-headed and foggy, and I realized as we talked that I was in subspace. It’s unusual for me to lapse into that space from such a short and, frankly, non-naked interaction – but he had made me so submissive and turned on that it made sense. He didn’t hold my hand as we walked, but he told me later that he wished he had; he was just shaken up and worried about me and worried about how long he’d been gone from work.
We got to the store and paused outside. “I’ll let you know when I’m coming back in February and maybe we can hang out,” I said, trying too hard to seem chill and unaffected.
“Yeah! Totally,” he replied, internally breathless but externally calm. We kissed goodbye, smiled at each other, and I went into the store, wanting to watch him stride off into his city but worried that’d seem uncool of me.
I didn’t think I’d see him again, honestly. I didn’t think he liked me enough to stay in touch. I didn’t think he wanted more from me than just that one weird almost-hookup in a Breather. But I’m chronically insecure about such things; he was showing interest, I just didn’t see it, didn’t believe it.
That afternoon he texted me a screenshot of the Breather receipt, captioned “for your records.” The following morning, I texted him, “Still thinking about those extremely good kisses,” and he replied, a mere eleven seconds later, “I was literally just thinking the same thing.” The next night, we sexted for the first time, while I was curled up on Bex’s living room sofa. The morning after that, he sent me a blisteringly hot selfie while I was waiting in a TSA line at the airport. The next day, when I was back in Toronto, he told me, “I’m really enjoying playing with you and getting to know you. I hope you know that.” I still didn’t quite believe he wanted me.
We’ve been dating for three months now and I still don’t quite believe it. But I’m happy about it nonetheless. I’m happy I answered that DM, happy I went on that coffee date, happy I kissed that boy in that Breather. I’m happy about it every day.
