When I first moved to Chicago, I didn’t really expect much except for crazy rent and endless winters. I found a shared apartment in Lakeview on a last-minute Craigslist post—a girl named Sarah needed a roommate fast. I remember the first day we met to look at the place: she was standing at the kitchen counter, messy auburn hair in a bun, faded jeans, and a baggy T-shirt. There was a quick, half-smile and a handshake. “I’m the world’s most boring roommate,” she said. “You’ll barely notice me.” Something about her made me think that couldn’t be further from the truth.
The first few weeks were standard roommate protocol—dividing up the fridge, coordinating trash duty, ignoring each other as we moved around the apartment. We’d exchange a few words here and there. I worked at a marketing agency, she was finishing grad school. Sometimes I’d come home late to find her sprawled on the couch reading, toes peeking out from under a blanket, glasses slipping down her nose. I’d make a quick mental note to not get involved with my roommate. Too messy. Dangerous. But then she’d laugh at something on TV, biting her lip, and I’d catch myself staring.
I kept telling myself: nothing’s going to happen. I’d been screwed over by “roommate situations” before, and besides, Sarah was all kinds of out of my league—cute, whip-smart, and apparently committed to maintaining our non-intersecting lives. But as the days crept by—late night kitchen runs, shared complaints about the radiator, one too many glasses of cheap wine on the couch—I started to feel the tension simmer under the surface.
One night, after a particularly long Friday at work, Sarah emerged from her room with two beers. “You look like you need this,” she said, plopping down next to me. I could smell her shampoo, something citrusy. Normally, I would’ve made some dumb joke to keep things light. But instead, we ended up talking for hours—about exes, family, why she hated winter. The TV played in the background. At some point, I realized our knees were touching. My pulse thudded.
She looked at me, a bemused challenge in her eyes. “Don’t you think it’s weird, how you can live with someone for a month and not actually know them?”
I cleared my throat, grinning. “Guess we’re fixing that, huh?”
Sarah rolled her eyes in mock annoyance. But when I stood up to head to bed, she caught my arm. “Hey. You want to keep hanging out? Just for a bit.” The way her fingers curled around my wrist sent a jolt through me. Suddenly, the space between us felt very small.
For the next week, everything changed in tiny, electric ways. Cleaning the living room became a team sport. Her hand would brush mine passing the remote. She started texting me from her room at night: “You up?” and “What are you listening to?” The kind of little things that don’t mean anything if you’re not looking for them—except now, I was.
Friday night came again. This time, it was my turn to bring wine. We ordered takeout, sat on the floor surrounded by cartons. She was wearing black leggings and a worn college hoodie, hair down, face scrubbed clean. She caught me looking too long.
“You okay?” she asked, smirking a little. “You’re staring.”
I hesitated, heat crawling up my neck. “I was just thinking…” My voice trailed off. I’d been here before, emotionally. You get too close, you tip the balance, someone gets hurt. I wanted it—her—but held myself back.
Sarah leaned in, voice low. “Thinking about what?” There was a wicked gleam in her eye that shot right to my groin.
I blurted, “If this is, you know… crossing lines.”
She didn’t look away. “And if it is?”
For a long second, I sat frozen, heart pounding. “Then maybe I don’t care.”
Sarah’s smile turned slow and lazy, lips barely parted. She slid closer until our faces were inches apart. “Neither do I,” she whispered.
She kissed me—tentative at first, warm and soft. My hand came up to tangle in her hair, her thigh pressed against mine. I felt every nerve ending light up. We broke apart, both of us breathing a little harder.
She laughed quietly. “Well… we just fucked up the roommate dynamic, didn’t we?”
I grinned, feeling reckless and stupidly happy. “Guess so.”
For a moment, though, I hesitated. New territory. Part of me wanted to press on—rip each other’s clothes off right there on the living room floor. The other part screamed caution: this was not just a hookup, not some Tinder fling. This was my home, my roommate, the one person I saw every day.
Sarah must have seen the panic cross my face. She paused, finger tracing my jaw. “Hey. I’m not going to make this weird. Only if you want this.” Her voice was gentle, surprisingly earnest.
I swallowed, heart jackhammering. “Yeah. I want this.” And in that moment, the decision was made.
We tumbled to the floor, bodies pressed tight. She pushed my T-shirt up and scratched her nails down my chest, and I groaned. I slipped my hand up her hoodie, over her bare waist, fingertips tracing the edge of her panties. Her skin was hot and smooth. We kissed again, deeper—unguided, desperate.
She pulled her hoodie off, tossing it aside. My hands cupped her breasts, thumbing her nipples through the thin cotton. She arched into my touch, gasping softly.
“Fuck, you feel good,” I said, voice ragged.
She laughed, low and dirty, then bit my earlobe. “You’re not bad yourself.”
Her hands found the waistband of my sweats, tugging hard. I helped her, groaning when she wrapped her fist around me. She stroked me slowly, thumb circling the tip as pre-cum smeared her palm. I shuddered under her touch, desperate for more.
“God, I’ve wanted this,” she whispered, straddling me, hair brushing my cheek. She yanked her leggings down, wriggling out of her panties. When she slid over me, wet and tight, I nearly lost it.
She rode me slow, hips rolling, mouth on mine. Every grind sent lightning up my spine. I grabbed her ass, pulling her down harder, until her breath hitched and her nails dug into my shoulders.
“Don’t stop,” she gasped, voice strained.
I sped up, thrusting into her—rough, desperate, hungry. The intensity caught us both off guard, bodies slamming together on the living room floor. I watched her face change as she came—head thrown back, hair wild, mouth open. The sight alone almost pushed me over the edge.
“Sarah—fuck, I’m gonna—” I managed, burying my face in her neck as I came, hips jerking, lost in the heat and rush.
We collapsed together, limbs tangled. For a moment, neither of us spoke—just panting, sweat sticky between us. I thought maybe things would feel awkward, tense. But she just laughed, rolling onto her back and kicking me gently.
“That was… a really good terrible idea,” she said, grinning.
I laughed, relief and something like joy flooding my chest.
“So… still want me as your roommate?” I joked, breathless.
Sarah rolled her eyes. “Hell yes. Maybe with some serious benefits.” She rolled on top of me, lips finding mine. And just like that, everything messy and complicated felt worth it.