I never planned to find myself lusting over my office colleague, let alone confessing it to anyone—not even myself. But there’s something about late nights, shared stress, and that thrill of the forbidden that changes how you see someone. My name’s Megan, I’m 28, and this is how things unfolded between me and Jake, the guy I never thought I’d cross professional boundaries with.
Jake started at the company about eight months ago. He’s tall, dark brown hair always kind of messy, and has this easy grin that makes people relax. We work in one of those open-space ad agencies in downtown Chicago, where “creativity” means you’re up at 2 a.m. with a deadline and still expected to look sharp the next day. Honestly, our team mostly survives on caffeine, stress, and sarcasm.
I’d noticed Jake before, of course. He was funny in meetings, good at handling clients, always willing to pick up extra work. But I was sure he belonged to that breed of ‘perpetually single, playboy’ types—lots of hookup stories at Friday drinks, zero real relationships. I wasn’t looking to get involved, especially with someone at work.
But, as fate would have it, we were assigned to manage the Rolland account together—a campaign with impossible demands and a brutal deadline that meant a lot of overtime. For weeks, it was just the two of us left in the office at night, eating takeout, sharing playlists, swapping stories, and volleying ideas back and forth over glowing laptop screens.
I should mention: my own love life had been stagnant. One or two forgettable Tinder dates. A handful of boring, self-absorbed men. Nothing that made my heart pound. But Jake? He was different in those quiet moments when the rest of the world faded away.
Sometimes, when we both reached for the same mug in the staff kitchen, our hands brushed and he’d laugh. Our knees would graze under the table and neither of us seemed to mind. I felt it building—a tension thick and electric—but I kept shoving it down, telling myself I couldn’t risk my job or my dignity for a quick office fling.
One night, it was pouring rain, and we were the only two people left, fussing over layouts for a client presentation. Jake came back from the kitchen, two steaming mugs in hand, and sat right next to me, way closer than necessary. I could feel his thigh pressed against mine.
“You look exhausted,” he said softly.
I huffed, forcing a laugh. “Speak for yourself, Mr. Five O’clock Shadow.”
He smiled, dipping his head so his eyes locked on mine. “You ever feel like you’re just… stuck? Like your life is on repeat?”
I was surprised—Jake rarely talked about anything deep. But that night, the city lights bouncing off the rain-spattered windows, something changed. We both let our guards down, maybe just for a second longer than we should have.
“Yeah,” I admitted. “Sometimes I think about just… shaking everything up, doing something reckless.”
Our eyes met, and there was a silence that seemed heavy with promise. I wanted him, badly, and I saw it in his face that he wanted me too. My heart beat so hard I was sure he could hear it.
But right then, I panicked. I stood up, making some lame comment about my taxi app glitching and fled the office as fast as I could without looking back.
The next day, I was jumpy as hell. I couldn’t focus. I was mortified at how obvious my attraction must have been. Jake just acted normal, but every look, every joke held an undercurrent—something private passed between us.
For the next week, I avoided him after hours, pretending to be too busy to stay late. But our campaign was due, and eventually I had no excuse. Thursday night rolled around, and I found myself back at my desk at 9 p.m., alone until Jake appeared, dropping his bag onto the nearby chair.
I tried to make small talk, but he cut through it, his tone low. “Are we going to talk about the other night, or are you just pretending it didn’t happen?”
My cheeks burned. “I don’t know, Jake. I don’t want things to get complicated.”
He moved closer. “Maybe that’s exactly what we need. Complicated.” His eyes darkened, and he looked me over, lips parted. “I want you, Megan. I haven’t wanted someone this bad in years.”
My resolve weakened. “This is insane. What if someone finds out?”
Jake grinned. “Then we’ll just have to be careful.”
Something snapped inside me. I pushed my chair back, meeting his eyes full-on. “Prove it.”
He stood up, slow and deliberate, and in two steps he was behind me, his hands sliding over my shoulders, massaging away stress. I shivered, feeling excitement coiling low in my stomach. His hands drifted down, brushing my collarbones, fingers lingering at the edge of my blouse.
He bent low, lips brushing my ear. “Tell me to stop if you want.”
Instead, I leaned into him, letting my head fall back, my lips parted. “Don’t.”
Jake turned my chair, tangling his hand in my hair to pull me up, his mouth crashing against mine, hot and insistent. I kissed him back, hungry, years of boring dates and pent-up wanting flooding into that moment. Our tongues tangled, his hands gripping my waist as I clung to him, desperate and breathless.
He unbuttoned my blouse, lips following his fingers down my neck, across my collarbone, teasing over my bra. His breath hitched, eyes brimming with lust. “You’re so fucking sexy, Megan.”
I tugged at his shirt, pulling it over his head, running my hands over the muscles in his chest and shoulders. Every inch of him pressed against me felt like fire—I couldn’t get enough.
He spun me around, bending me forward over the edge of my desk. My skirt bunched up as he cupped my hips, grinding into me, making me gasp.
“You sure you want this?” he growled, voice rough.
“Yes,” I rasped, barely above a whisper. “I need it.”
He yanked my panties down, fingers slick with my arousal as he teased me, drawing slow, torturous circles. I moaned, biting my lip, knuckles white as I gripped the wood.
He thrust into me, hard and deep, filling me so perfectly I almost sobbed. His pace was relentless, each stroke making my whole body tremble. I matched him, pushing back, breath ragged, the clatter of the desk and our panting the only sounds echoing through the empty office. His hand snaked around, fingers finding my clit, rubbing in fast, tight circles that sent me spiraling.
“Fuck, Jake—” I cried, coming undone, waves crashing through me. He followed, groaning my name, body shuddering against mine.
We collapsed onto the floor, still tangled together, laughing breathlessly. For a moment, nothing existed except us, sticky and satisfied, surrounded by half-finished layouts and cold coffee.
Afterwards, we dressed quickly, trading kisses, smiles, and promises to keep this just between us. I knew nothing would be the same again, but I didn’t care. For once, I felt alive, reckless, and wanted.
I told you—I never meant for this to happen, but my god, I don’t regret a thing.