The wedding had been a blur of soft jazz, clinking glasses, and too many names I didn’t remember. I wasn’t supposed to feel anything tonight. Not really. Just show up for the bride, smile through the photos, maybe flirt a little if the champagne worked its magic. But now it was after midnight, and I was barefoot on the rooftop of the Montrose Hotel, tipsy and hot, with the Chicago skyline teasing me like it knew something I didn’t.
I should’ve gone to bed. Instead, I was sipping my second glass of Prosecco and leaning into the breeze when I heard him.
“You look like trouble.” I turned back to see one of the most good looking men I’ve ever seen. I had seen him during the ceremony, toward the front on the groom’s side of the aisle. He must have been a close friend or family member. I caught myself glancing at him throughout.
The voice slid down my spine—low, confident, unapologetic. I turned, and there he was. Shirt half open, hair tousled like he'd just stepped out of someone else’s bed, and a smirk that made my thighs clench without warning. Every instinct told me to walk away. Instead, I smiled into my glass. “Funny. I was just thinking the same about you.”
He stepped closer. I could smell him—cedarwood and something darker, something I couldn’t name but wanted to inhale again. I tried to play it cool. Deflect. But every time he opened his mouth, my body betrayed me just a little more. And then he said it.
“Room 604. Big bed. City view. Champagne.”
I laughed, but my pulse was pounding. I should’ve said goodnight and meant it. But instead, I walked away from him, barefoot through the rooftop bar, into the elevator. I didn’t look back. Not once. But my hands were trembling.
I told myself I was just curious. That I’d press the button, see what the hallway looked like, maybe walk past his door and let it be nothing but a near-miss.
Instead, I got off on the sixth floor, and there he was. Waiting.
His shirt was still open, and he looked like sin with the patience of a saint..
“You took your time,” he said. “I almost didn’t come,” I whispered, voice thinner than I wanted it to be. He stepped aside. “You came. That’s what matters.”
I walked past him. Slowly. Feeling the heat of his gaze trail over my skin as I moved toward the window past his bed. The city glowed outside, but I wasn’t focused on the view.
I was focused on him. His stillness. His restraint. The way he didn’t touch me. He had such a stoic face, impossible to read.
“Really?” I asked, without turning around. “You’re not going to make a move?” “Not until you ask me to.”
I turned then, and something shifted. He opened a bottle with one hand—effortless, like everything else about him. And then he asked me a question that made my breath hitch.
“How would you like to play a game?” “What, like truth or dare”, I teased. “Yes, actually.”, he said casually. “Fine, ask me first then.”, I said all too confidently. “Truth or dare?” he said.
“Dare.”, said not me, but the prosecco. I immediately thought about how I should have asked for a truth question.
Take off your dress. The world narrowed to the sound of my heartbeat.
I didn’t speak. Didn’t think. Just set down my glass on the bedside table and reached behind me. My fingers found the zipper of the tight dress I had picked out just a day before arriving in Chicago, and slowly, I pulled.
The silk slipped down my body like a secret I’d been dying to tell. And then I was standing there in just my black lace slip that came with the dress, flushed, exposed, every inch of me trembling and alive. He didn’t touch me. Didn’t move. He just looked at me like he was starving. I felt powerful.
“I think it’s my turn to ask,” I said softly.
Leo stood. His eyes dark, lips parted like he was about to taste something rare and forbidden. And I knew. I wasn’t leaving that room with my dress on. And I didn’t want to.
Leo stood. “No more questions.”, he said sternly. Not a fair game as far as I can tell, but I’m not sure I care.
The tension between us was molten now. His gaze dragged down my body, pausing at my chest, which was outlined by the lace slip. He didn’t say a word. Just stepped in, cupped my jaw, and kissed me like he’d been holding back all night.
And I kissed him back like I was done pretending I hadn’t wanted this from the second he opened his mouth. We didn’t fumble.
His hands were sure, tugging at the lace on my chest, freeing my breasts, thumbs circling my nipples until I was gasping into his mouth. I stood to meet his body and pressed against him, our mouths still engulfed while he explored me with those big hands. He slides the slip down my body. The fabric is smooth as it circles at my heels. Then lower—fingers sliding from my jaw, all the way down to the wetness between my thighs.
“Fuck,” he murmured, eyes locked on mine. “You’re dripping.”
I didn’t even try to answer. Just kicked the slip away and pulled us both down together onto the bed.
He stripped fast—belt, pants, boxers—gone. And when I saw him, thick and ready, I reached for him without thinking, stroking once, twice, slow, watching his jaw tighten.
“You keep doing that,” he growled, “and I’m not gonna last long enough to ruin you the way I want.” I spread my thighs. “Then shut up and fuck me.” He didn’t hesitate.
One deep, perfect thrust and I cried out, my back arching as he filled me. He was so thick that it hurt, but I had never felt such a rush of pain and pleasure simultaneously. He cursed under his breath and held there, buried inside me, his forehead resting against mine.
“Jesus, Clara,” he groaned. “You feel…”
“Move,” I begged. He did.
Hard. Deep. Each thrust hit something devastating. My nails raked down his back, hips meeting him greedily, chasing every wave of pleasure like it owed me something. When his fingers found my clit, it was over. He was circling it with his thumb while his mouth was on my chest, licking and softly biting my nipples.
I came fast—sharp and sudden, crying out his name as I clenched around him. Every muscle in my body tensed and I had the most intense orgasm I’ve ever experienced. His moaning in my ear tells me that he can feel how tightly my inner walls are clenched around him as I cum. He followed seconds later, teeth sinking into my shoulder as he groaned into my skin, hips grinding against mine in one final, desperate push.
Then silence.
Just breath and sweat and heat between us. His voice was rough against my neck. “Still think I’m trouble?” I laughed, dazed and wrecked. “You’ve got no idea.”
And I already knew— I wasn’t sleeping alone tonight.