Late Shift Service

I'm Robyn, thirty-four, an instructor at a startup accelerator, and that matters later, I promise. Also, names: Frank, forty-one, founder of some stealth-mode analytics thing that nobody was allowed to ask about.

The Thursday night I'm thinking of, I'd taught a hackathon workshop for nine hours straight. Nine hours of explaining API rate limits to founders who nodded without listening, then stayed after to argue with me about caching, then argued about the arguing. By ten p.m. the fifteenth-floor breakout lounge was empty except for me, my laptop, and the whiteboard covered in code nobody had bothered to erase. The city glow came through the glass walls, all orange and smudged, and the vending machines hummed like they were thinking about something.

I was shutting down my laptop when Frank appeared.

I knew of Frank. Everybody knew of Frank in the vague way you know the brooding founder who took a corner desk and never joined the lunchtime chatter. We'd exchanged maybe six words total since his cohort started. He stood there in the half-light holding two glasses of red wine, which is not a thing a person does casually at ten p.m. in an empty office.

"You looked like you could use one," he said, and offered me a glass.

Here's what you should know about me before I go on. I was lonely. Not tragic-lonely, just the ordinary kind, where you teach competence all day and go home to a quiet apartment and the last person who touched you was a fellow instructor three years ago, and that fling ended when he took a job in another city and neither of us pretended to be sad about it. I was good at my job and invisible outside it. That math does something to a person.

So I took the wine. We sat on beanbags near the window and talked about nothing for a while, and then Frank got weird, which I want to describe accurately because it mattered.

He said he'd watched me all week. Not in a creepy way, he clarified immediately, and then made it worse by clarifying more. He said he found my competence attractive, specifically, the way I handled the room, the way I didn't flinch when a founder pushed back. He said the word attractive and then went red and stared into his wine like it had text on the bottom of the glass.

And then he proposed the thing.

It took him three tries to get it out. He wanted an arrangement. Private, after hours, discreet, paid if I wanted, though I said right away no money, because the second money enters a thing I teach ethics workshops about, I'm out. The arrangement itself was that he would dress for me. Women's clothes. Lingerie, a dress he'd already bought and never shown anyone, and he would let me take the lead, and nobody would ever know.

He said all of it in a stammer, flushing darker with each sentence, and when he finished he looked as if he were waiting for a verdict.

I thought about it for exactly one sip of wine. Not because I wasn't nervous. I was. But here was a grown man, forty-one years old, CEO of a company with real funding, confessing something he'd carried for probably decades, to me, because he decided I was the person who wouldn't laugh. That did something to the invisibility. Somebody had looked at me all week and seen somebody worth risking humiliation for.

"Okay," I said. "Friday night. Same time."

He blinked like I'd spoken a language he only half remembered. Then he said thank you about four times and I told him to stop before it got embarrassing for both of us.

* * *

Friday night I came back up at ten and the lounge was exactly as empty as before, half-lit, humming, the whiteboard now wiped clean like he'd prepared the room. Frank was waiting by the window with a gym bag at his feet, and his face was already flushed, which told me he'd been standing there working up his nerve for a while.

"Hey," I said.

"Hey. Hi. You came!"

"You invited me, Frank."

"Yeah, I know, I just." He trailed off and gestured at the bag like it explained everything.

I told him to take his time. He picked up the bag and excused himself to the restroom down the hall, and I stood alone in the lounge for eleven minutes, which I know because I watched the clock on the microwave and did breathing exercises like a person about to give a talk. My nerves were real. I want to be accurate about that. I'd never done anything like this, and part of me kept whispering that I had no idea what I was doing.

Then he came back, and I stopped whispering to myself.

He wore a simple black silk slip, knee length, thin straps, and a pair of black heels he clearly hadn't practiced in, because he walked like a man crossing ice. No wig, no makeup, just Frank's face, forty-one and a little lined, burning red from his collar to his ears, above a garment that fit him better than I'd have guessed. He'd shaved his legs. That detail undid me a little, the preparation of it, the decision leading up to shaved legs and a slip folded in a gym bag.

He stopped a few feet away and stood there trembling, actually trembling, hands loose at his sides like he didn't trust them.

"Okay?" I asked, because the trembling worried me.

"Okay. Yes. Just." He exhaled. "Nobody's ever seen this. Not the dress, not any of it. Forty-one years and you're the first."

I crossed the room slowly and steered him to sit down on a beanbag by the window, and he went down into it awkwardly, knees together, heels awkward under him. I knelt beside him, took my time, and traced one finger along the lace edge at the hem of the slip, up near his knee, barely touching. He shivered under a touch that light.

"Is this okay?" I asked.

"Yes. God, yes."

"Are you okay, though? Honestly. Tell me if you want to stop."

He looked at me then, flushed and scared and somehow steadier. "I'm okay. I've thought about this for so long that I don't know what to do with my hands, but I'm okay."

"Leave the hands," I said. "I'll tell you where they go."

I kept tracing the lace, slow, back and forth along his thigh, feeling the silk shift over him, and he breathed like he was learning how lungs worked. I let the quiet stretch. The city glowed and the vending machines hummed and some part of me realized I wasn't invisible in this room at all, that this grown man had put on a dress because he wanted me to see him in it.

"You look good," I told him, and meant it. "The slip suits you. The heels need practice."

"I've been practicing in my apartment for two weeks." He laughed, shaky. "Fell twice."

"Take your time with those." I moved my hand up to the strap on his shoulder, followed it with a fingertip, and paused there. "Frank. Can I touch you more? Properly?"

"Please."

"Words, since we're being careful with each other."

"Yes. Please, Robyn. Touch me."

So I did, and that's where the night really started, but the start of it, the part I keep coming back to, was the lace under my fingertip and the sound he made, this small released breath, as if he were putting down something very heavy that he'd been carrying for years. I sat there on the floor of a borrowed lounge with a founder in a black silk slip, and I felt seen for the first time in three years. Funny how that works.

"Tell me what you've imagined," I said, and he did, and we had all night.

He talked for a while, actually. About dressing in his apartment at night with the curtains drawn, about ordering the slip and hiding the box under his bed like evidence, about the companion he'd paid who'd moved away a year ago, so he'd stopped. He'd never said any of it to someone he trusted before, he said, and you could tell, because the words came out stiff and over-rehearsed, like a pitch he'd drilled alone in the shower. I listened. I'm good at listening, it's most of my job, and it turned out that was its own kind of intimacy, sitting on a beanbag on the fifteenth floor while a founder confessed something he'd carried since before my workshop existed.

Then he reached over and touched my wrist, just my wrist, and asked if he could kiss me, and I said yes, and that was its own small victory for both of us, I think. He kissed carefully, like I might break or bolt, and when I made a noise into his mouth he pulled back to check on me, which was sweet and also slightly annoying, so I took his hand and put it on my waist to show him the wrist rule did not apply everywhere.

We moved slow after that. His hands found the small of my back and gripped there, deliberate, like he'd been given instructions in a dream and was following them from memory, and I whispered adjustments as they came to me. Higher. Softer. No, there, keep that. He was an astonishingly good student, which tracks, he's a founder, they're all desperate to be told they've done a thing correctly. I got his strap back off his shoulder and he shivered again, and I got my shirt over my head and he went quiet in a way that I decided to take as a compliment.

"You're staring," I said.

"Sorry."

"Don't be sorry. Stare."

He did. And what I didn't expect, what I keep turning over even now: being looked at like that, hungry and a little reverent, by a grown man in a silk slip, fixed something in me that three years of solo takeout and webinars had let rust over. He found me attractive. Not my slides. Not my workshop structure. Me.

We paused there for a while, both breathing, my hand flat on his chest, his heart beating fast and light under my palm. He smoothed the slip over his thighs and said, mostly to the window, "I bought a dress too. Green. It's still at my apartment because I chickened out about the bag."

"You should bring it next time," I said, and he turned to me so fast I almost laughed. Next time. Plural nights, a future tense, the arrangement actually existing. "If there is a next time," I added, because fair is fair, and he said there was, he absolutely hoped there was, and I said good, then, bring the green one.

Then I had him stand up and turn around, because I wanted to see the whole silhouette, the slip and the shaved legs and the heels he hadn't fallen in yet, and he did this slow careful rotation for me like the world's tallest, most nervous runway model. When his back was to me I told him to walk a few steps, just a few, and he did, and I watched his hips move. That's the phrase and I'm sticking with it, because there's no fancier way to say it. He had a walk he'd clearly built from nothing, a little stiff, a little self-conscious, hips shifting under the silk with each careful step, and I sat on the beanbag with my chin in my hand and enjoyed it more than I have enjoyed most things this year. He glanced back over his shoulder to check the grade and I told him to face forward, he wasn't done, and he faced forward.

Eventually the heels had to go, because he wobbled on the rug edge and grabbed a chair, and I decreed the demonstration over. He got down onto the floor in front of the window, onto the pile of beanbags actually, shifting onto his back among them, slip riding up his thighs, hair a mess against the dark fabric. I stripped the rest of the way off while he watched, then found the condom in my jeans pocket, because I'd come prepared and apparently so had he, there was a box in the gym bag, of course there was, the man prepared for contingencies.

"Can I?" I asked, kneeling over him.

"Please," he said, and then, "I might be bad at this."

"You'll be fine. Follow instructions. You're good at that."

I straddled him and took the lead, slow, my hands on his chest, guiding the pace with my knees and my weight while he held my hips like I was something he was afraid to squeeze. The slip was still on him, bunched up around his waist, silk against my thighs, and I rolled my hips and found a rhythm and told him not to speed up, which was the hardest instruction I gave all night, poor man. He kept his eyes on my face the whole time like I might disappear if he blinked. The city glowed orange through the glass behind his head and the vending machines hummed their idiot hum and I fucked a CEO on the floor of an incubator lounge, slow and steady, and felt extremely visible the entire time.

Somewhere in the middle he stopped being careful. His hands tightened on my hips, actually gripping now, and the pace built even though I hadn't ordered it, and I let it, because watching him lose the composure he'd been clutching all night was better than any instruction I could give. I leaned down and got a hand in his hair, held on, and he turned his face into my shoulder and gasped against it, muffled, these broken helpless sounds that I felt more than heard, vibrating right through my collarbone into my chest. I was close. He was closer. I told him so, plain words, and he made a sound against my neck and came apart under me, and the feeling of him going, the shudder of it through his whole body, took me over the edge right behind him.

We stayed there a while. He was heavy, and the beanbag pile was not designed for two adults, and I didn't care about either problem. His hand had found mine somewhere in there and our fingers were laced up beside his head, which neither of us had planned. Eventually I rolled off onto the neighboring beanbag and we lay side by side staring at the ceiling, cooling off, the city smearing orange behind us.

"That was," he started, and stopped.

"Yeah," I said. "It was."

He got up eventually, unsteady, and peeled the slip off carefully over his head, folding it like it was dry cleaning worth money. I watched him from the floor while he stepped back into his jeans, hopping a little, and something about the sight, this big serious founder tugging his jeans on over bare skin with his dress folded over a chair, made the whole night feel real in a way it hadn't yet.

"Frank," I said. "Does next Friday work?"

He looked up, one leg still in his jeans, and grinned, still a little breathless, cheeks pink. "Next Friday works. I'll bring the green one."

"I'll bring the instructions," I said, and he laughed, and I lay back on the beanbags and listened to him fold the slip into the gym bag like it was the most precious cargo in the building.