The St. Regis Send-Off

When my phone lit up at 1:17 a.m. on a Friday, I wasn’t surprised. The name on the screen was “Chloe C.” I’d just gotten back from a developer mixer, still in my slacks and a button-down, sipping a neat bourbon and going over a contract. I swiped answer.

“Ian?” Her voice was a slurry mess, a mix of tears and way too many sugary cocktails. The background noise was pure chaos—girls shrieking, bass-thumping music, the sound of a city street. A classic bachelorette party finale.

“Chloe? You okay? You sound a little… off-market.” I kept my tone light, professional, even. It’s how you handle a volatile situation.

A wet sniffle. “They left me, Ian. My fucking friends. They just… put me in a cab and told the driver an address. I don’t… I don’t wanna go home alone. Not tonight.”

I took a slow sip of bourbon, the pieces clicking into place. Chloe. My cousin. Thirty-five years old and finally tying the knot with a seventy-year-old finance guy from Connecticut. The pre-nup was probably thicker than the phone book. The guy had more money than God but let’s be real, he wasn’t keeping up with a woman like Chloe in the bedroom. She was all curves and fire, and he was… well, he was a retirement portfolio with legs.

“Where are you now, sweetheart?” I asked, my voice a low, calm counterpoint to her chaos.

“The… the St. Regis. Lobby. The concierge is looking at me like I’m a vagrant.” She let out a hiccup that was half a sob. “Ian… please. Can you… can you just come? I need… I don’t know what I need.”

I knew exactly what she needed. She needed to feel something real before she signed her life away to be a trophy wife in a gilded cage. She needed a reminder of what a real man feels like. It was practically a civic duty.

“Stay right there, Chloe. Don’t move. I’ll be there in twenty minutes. I’ll handle the concierge.” I was already grabbing my blazer and keys. This was a much more interesting negotiation than any property deal.

I found her slumped in a plush armchair in the grand lobby, a vision of disheveled beauty. Her dark hair was escaping a complicated up-do, her makeup was smudged, and her little black dress was riding up her thighs in a way that was absolutely indecent. She looked lost, vulnerable, and utterly fuckable. The concierge gave me a grateful nod as I approached, the clear-headed relative here to manage the situation. Little did he know.

“Hey, trouble,” I said, offering her my hand. She looked up at me with those big, glassy eyes, and a fresh wave of tears welled up.

“I’m such a mess,” she whispered.

“We’ll get it sorted. Come on.” I pulled her up, my arm slipping around her waist to steady her. She felt incredible against me, soft and warm and pliant. I guided her towards the elevators, my demeanor all business, a property manager assisting a client. Once the elevator doors slid shut, the dynamic shifted. She leaned into me, her head on my shoulder, her breath hot against my neck.

“He’s so old, Ian,” she mumbled into my shirt. “His hands are… cold.”

“Shhh,” I murmured, my hand stroking her back. “Don’t think about that tonight.”

I got her into the room—a suite, nice, good bones—and sat her on the edge of the king-sized bed. I poured her a glass of water from the minibar and made her drink it. She was watching me now, the alcohol haze clearing slightly, replaced by a raw, nervous energy.

“Why did you come?” she asked, her voice small.

I knelt in front of her, putting us at eye level. “Because you asked me to, Chloe. And because I know what you really need.” I let my hand rest on her knee, my thumb making slow circles on her inner thigh. Her breath hitched. She didn’t pull away.

“I shouldn’t…”

“You called me for a reason,” I said, my voice dropping to that persuasive, closing-the-deal register I use on hesitant buyers. “You didn’t want a babysitter. You wanted a send-off. A real one.”

That was all the permission she needed—or that I needed. I leaned in and kissed her. It wasn’t gentle. It was hungry, possessive, a claiming. She melted into it instantly, a moan vibrating in her throat as her hands came up to clutch at my shoulders. She tasted like champagne and desperation.

After that, it was a blur of discarded clothing. Her dress hit the floor, then my shirt. I laid her back on the bed, her body a pale, stunning contrast against the dark duvet. She was all woman—full breasts, a narrow waist flaring into generous hips. I took my time exploring every inch, with my hands, my mouth, my tongue. I was teaching her, reminding her what a real connection felt like. She was responsive, arching under my touch, her little cries and whimpers the best kind of feedback. When I finally slid into her, she was so wet and ready she cried out, her eyes wide, her nails digging into my back.

“Oh, God, Ian…”

“That’s it, sweetheart,” I grunted, setting a deep, relentless pace. “This is what you needed. This is real.”

I fucked her thoroughly, first on her back, then with her on her hands and knees. I pulled her hair, I spanked her ass until it was pink, I made her say my name. She came over and over, each orgasm hitting her like a tidal wave, leaving her trembling and begging for more. She was an eager student, and I was more than happy to provide the lesson plan.

Then, as she was gasping and sweaty beneath me, I leaned close to her ear. “You think we’re done?” I whispered, my voice rough. “We’re not done. I’m gonna take that pretty little ass now. Your wedding present from me.”

She froze for a second, a flicker of fear in her eyes, but it was quickly swallowed by a wave of pure, unadulterated lust. She just nodded, biting her lip, and buried her face in the pillow.

I was slow, I was careful, I used half the minibar’s lotion, but I was relentless. And when I finally pushed all the way inside her, her scream was muffled by the pillow, a sound of pain, shock, and the most intense pleasure she’d ever felt. She came again, violently, her body clamping down on me like a vise.

I followed soon after, emptying myself into her with a groan that felt like it came from the bottom of my soul. I collapsed next to her, both of us spent, slick with sweat, the room smelling of sex and expensive hotel air conditioning.

We didn’t speak. There was nothing to say. The negotiation was complete. The deal was closed. She rolled over, curled against me, and was asleep in minutes. I lay there, staring at the ceiling, a satisfied smile on my face…