I know it’s a cliché, but sometimes the most unexpected moments happen where you least expect them. It started innocently, as these stories always do, and I’m pretty sure Emily and I were both surprised where a few weeks of office flirtation could lead. Looking back, I can’t tell if it was pure luck or a slow build-up of desire that tipped me over. But it’s hard to hide chemistry—especially when you work late, side by side, with barely anyone else on the 24th floor to see or hear you.
I work in a downtown Chicago marketing agency, one of those open-plan nightmare offices where everyone hunches over their laptops and tries to tune out the constant buzz. Emily joined the team around spring—slim, tall, brown hair cut short in a practical bob, always wearing those tight black pants that made her look like she could belong on the cover of a fashion magazine if she actually cared about that sort of thing. She was sarcastic in meetings and brilliant at her job, and she had this nervous habit of chewing her pen that I found weirdly sexy.
At first, I hardly noticed her more than anyone else. I have a girlfriend—well, had at the time, I should probably say, though things were already rocky between us. Emily didn’t seem especially interested in me. We were just coworkers: swapped a few jokes, rolled our eyes during client calls, stayed late sometimes. She’d order extra fries and push half my way. There was easy, constant banter between us, never crossing any real line, but I remember being surprised at how much I missed her whenever she had a day off.
It wasn’t until late May, during the week from hell before a big campaign launch, that something shifted. We were at our desks after 9 p.m., everyone else gone, this hazy quality settling over the fluorescent lights. I could tell Emily was exhausted—her jacket was off, sleeves pushed up, feet kicked out under her chair. She was quietly humming to herself, her sandal tapping out some rhythm on the carpet, when she caught me staring. Instead of looking away or making a joke, she smiled, slow and sly.
“You’re still here?” She raised her eyebrow. “Getting your overtime’s worth?”
“I think I forgot what home looks like,” I shot back. She snorted.
“Could be worse, you could be doing this alone.” She tossed me a look, the kind that lingers for a split second longer than you expect. My throat felt dry.
I told myself it didn’t mean anything. Probably, she was just tired, maybe feeling friendly because stress does that to people. But when she slid over a coffee she had made for me from the disgusting office Keurig, and her leg lightly brushed mine under the table, I felt something low in my stomach twist with anticipation.
I didn’t act on it, not at first. I tried to keep things cool: kept the banter funny but distant, didn’t let our knees touch again the next night, went home on time even when she lingered behind. Part of me felt crazy for reading into things—maybe I just wanted something to distract me from my failing relationship. Plus, aren’t office hookups always a bad idea? And Emily, despite her effortless sex appeal, never said or did anything openly direct.
But I saw the way she’d bite her lip when I cracked a joke, I noticed her glancing up at me over her glasses, and there was a definite shift—almost like we were playing chicken with our own attraction.
It wasn’t just me who noticed, either. Our friend Alex from HR once cornered me by the printer.
“You and Emily seem close,” he smirked. “She’s cool.”
I shrugged it off. “Everyone likes Emily,” I said.
He chuckled. “Yeah, but you actually watch her when she leaves a room—don’t think I haven’t seen you, dude.”
The next time Emily and I worked late, I caught her watching me too. I accidentally brushed against her arm reaching for the mouse and neither of us moved away. It was a buzz, an electric charge humming through me, and suddenly the old risk didn’t seem as strong as the excitement pushing me forward.
That Friday, our campaign went live. End-of-week drinks spilled over into 1 a.m. karaoke. Half the team stumbled off to cabs by then, but Emily and I split an Uber back to the office to pick up our bags. We were giggling like teenagers as we went up the elevator. She was tipsy, glasses askew, laughing at a joke I don’t remember telling. I could feel every inch of my skin tingling with nervous energy.
“Dare you to do a cartwheel in the lobby,” she grinned.
I tried, failed miserably, and she burst out laughing. She leaned against the glass door, hair falling into her eyes, and let out a soft hum. Her gaze flicked down my body—quick, but absolutely unmistakable.
“Okay, that was hot,” she said.
I wasn’t sure I heard her right.
“What?” I tried to sound casual but my pulse was thrumming.
She stepped closer, definitely invading my personal space. There was something different about her—like she was finally letting her guard down, her voice lower and warmer.
“Don’t pretend you haven’t noticed,” she whispered, standing close enough for me to smell the faint vanilla of her perfume. “You watch me.”
I could hardly breathe. “And if I do?”
She smiled, then closed the space between us. Her lips brushed mine—tentative, testing, then firmer, hotter. My whole mind blanked except for the rush of heat that coursed through me.
“I shouldn’t…” I started, but I couldn’t stop kissing her; tasting the tang of whiskey and sugar on her tongue, running my hands unconsciously up her sides. It had been so long since someone actually wanted me like this, and the way she pressed her body against mine, rolling her hips into me, made it impossible for me to think of anything except how much I wanted her.
Emily’s hands slid under my shirt, her nails tracing along my stomach. I groaned as she pushed me against the cool glass, her mouth trailing to my ear.
“I know it’s late, but I’m too wired for sleep,” she whispered. “Come upstairs with me?”
There was no one else in the building, only cleaners three floors down. The idea of getting caught made it ten times hotter, and suddenly all my hesitation melted away. I nodded, probably too eagerly, and she took my hand, pulling me along into the elevator and up to our floor.
In the dim light, she turned and pressed me against the wall, her hands working at my belt. Her mouth was on my neck, biting and kissing, her breaths coming faster. I raised her shirt, fingertips tracing along the bare skin of her back, feeling her shiver. The air was thick with the scent of arousal—I could smell her, taste her kiss, feel the insistent hardness between us. Her body was slighter than I expected but fierce, all curves and heat.
Emily slid her pants off, standing in nothing but black lace underwear, her eyes boldly daring me to say or do anything to break the moment. My mouth went dry as I knelt, kissing along her thighs, feeling her tremble under my hands.
She gasped my name, soft at first, then louder when my tongue found her—slick, wet, desperate. She pulled me up, pushed her hips into mine, unbuttoned my jeans with nimble fingers. Everything after that was a blur of skin and heat and raw, hungry movement. She wrapped her legs around me—office desk digging into my lower back, her teeth at my jaw, her breaths becoming panting moans.
“Fuck, that’s good,” she choked out as I thrust into her, hard and deep. I gripped her hips and moved faster, both of us teetering on the brink. The desperate, breathless sounds she made set me off, and I felt her tighten around me, her hands digging into my shoulders.
We came together, stifled moans echoing off glass and steel, collapsing in a tangled heap of sweat and laughter.
After, we just lay there: naked, backs sticky against the cold desk surface, hearts racing out of control. Emily kissed me—slow and tender this time, all the urgency gone. I brushed a strand of hair out of her eyes and tried to catch my breath.
“So, you want to do overtime again next Friday?” she grinned, sharp and beautiful.
I laughed. “Only if you promise to help me with my workload.”
She bit my lip gently. “Oh, I think you’ll find I’m always willing to put in the extra hours.”
We dressed quietly, exchanging one last lingering kiss before parting downstairs. As I walked out into the cool midnight air, all I could think was: Sometimes, the best things really do happen when you’re willing to take a risk. Even if it’s with a coworker, after hours, when no one’s watching. And when I saw Emily’s sly smile in the elevator reflection, I knew I’d want so much more than just overtime.