Chapter 1: Swipe Right on a Softball Star
The wind coming off the Chicago River carried a damp chill, but up on the rooftop bar, Henry felt nothing but the smooth warmth of the Macallan 25 in his hand. He leaned against the cool wrought-iron railing, watching the colored lights of the architectural tour boats paint the dark water. Below, the wail of a siren cut through the steady hum of the Loop, a familiar soundtrack.
He checked his Rolex. She was five minutes late.
When he saw her emerge from the glass elevator, his grip on the crystal glass tightened just a fraction. Kailani. She was scanning the space, her long black hair swept over one shoulder. The white sundress was simple, but it did exactly what it was supposed to do—it clung to every curve of her compact, powerful frame, the hem brushing high on her muscular thighs. He could see the definition in her calves, the strength in her shoulders. A softball player. An athlete. Perfect.
He lifted a hand, and her eyes found him. A shy, tentative smile touched her lips before she walked over, the confidence in her stride betraying the smile.
“Henry?” she said, her voice softer than he’d imagined from her photos.
“Kailani. Have a seat.” He pulled out the barstool next to him. “You found the place okay?”
“The elevator gave me a heart attack,” she admitted, sliding onto the stool. “All that glass. I could see the whole city dropping away.”
“Gets easier,” he said, signaling the bartender. “What are you drinking?”
She glanced at the menu, flustered. “I don’t know. Something sweet?”
“Two Portofino Sours,” Henry told the bartender without looking away from her. “Trust me.”
He watched her take in the view, the sheer drop, the glittering expanse of the city. He liked watching people see it for the first time from his world. “You play shortstop?” he asked.
Her eyes snapped back to him, alert. “Second base. How’d you know I played?”
“You walk like you’re ready to field a grounder. Balanced. Low center of gravity.” He took a sip of his scotch. “I pitched. Northwestern. A few years ago.”
The drinks arrived, frothy and pale. She took a cautious sip, then a deeper one. “This is amazing.”
“So, DePaul,” he said, leaning back. “Tuition’s a bitch, I hear.”
She nodded, swirling her straw. “Yeah. My scholarship covers most, but not all. And my parents… they’re back in Hilo. They do their best, but it’s tight.” She met his gaze then, and he saw the calculation in her dark eyes, the brave front. “Your profile didn't say what you do these days.”
“Investment banking. M&A mostly,” Henry said, keeping it simple. He swirled the amber liquid in his glass. “It’s a lot of numbers and ego, but it pays for the view.”
Kailani laughed, a genuine, warm sound that cut through the rooftop’s cool ambiance. “I’ll bet. This drink probably costs more than my textbook for Sociology 101.”
“Probably,” he agreed with a grin. “But it tastes better.”
They talked through the first drink, and by the time the second arrived—something with gin and lavender that she sipped with wide, appreciative eyes—the initial stiffness had melted. He made her laugh telling her about a disastrous client dinner where a man tried to impress him by eating a gold-leaf steak and nearly choked. She told him about the time she slid into home plate so hard she ripped her entire uniform pants.
“You’re kidding,” Henry chuckled.
“Swear to god. Had to borrow my teammate’s sweats to drive home. My coach called me ‘Slider’ for a month.”
The easy banter flowed, a comfortable back-and-forth that more like a real date than a hoo. Henry watched her shoulders relax, saw the assessing look in her eyes soften into something closer to interest. He waited for a lull, then leaned in slightly.
“Look, Kailani. I like you and you're damn sexy in that dress. I suggest we leave here and do what we both are looking for. No pressure. We can finish these drinks, you can take a cab home, and I’ll wish you the best.” He paused, letting the city’s murmur fill the space. “Or, you can come back to my place. Have another drink and see where the night goes.”
Kailani looked into her glass, then back at him. The city lights reflected in her dark eyes. She took a final, decisive sip and set the glass down on the polished granite bar with a soft click. “Okay,” she said. “Let’s go see your place.”
He paid the tab with a black card, and she slipped her hand into his as they walked to the elevator. Her palm was slightly rough, calloused from grip tape and batting practice, and the solid warmth of it sent a jolt of anticipation straight through him.
A black Lincoln Navigator was idling at the curb, the driver standing ready. Henry nodded, and he opened the door for them. Kailani slid in, her eyes wide. “You have a car just… waiting?”
“It’s easier,” Henry said, settling beside her. The door closed, sealing them in quiet, leather-scented darkness as the city slid by the tinted windows.
The ride was short. The elevator in his building was all brushed steel and silent, gravity-defying speed. When the doors opened directly into his foyer, Kailani stopped dead.
“Holy shit,” she breathed.
The entire west wall was floor-to-ceiling glass, a panoramic sweep of the skyline and the fading scarlet and gold streak of sunset over the river. The space was vast, with high ceilings, polished concrete floors warmed by deep, charcoal-colored rugs. The furniture was minimalist and outrageously comfortable-looking—a long, low sofa in navy velvet, a statement chair in oxblood leather, sleek shelves lined with books and curated art objects. It smelled of sandalwood and clean linen.
“This is… this is an apartment?” she asked, walking slowly into the living room as if afraid to touch anything. Her fingers trailed over the back of the sofa. “This is a museum. This couch probably costs more than my car.”
“It might,” Henry admitted, smiling. He watched her explore, her shyness replaced by pure wonder. She peered at an abstract sculpture, gazed out at the view, her expression open and stunned. This was the part he never tired of—the moment the scale of his world truly hit them.
“Can I… get you that drink?” he asked.
“Please. Yes.”
He went to the kitchen, a galley of marble and matte black appliances, and pulled a bottle of Dom Pérignon from the fridge. He brought it and two slender flutes out to the private rooftop patio accessible through a sliding glass door.
Out here, the city sounds were a distant symphony. The patio was furnished with a deep sectional sofa piled with wool throws, a fire pit flickering with blue flame, and planters overflowing with hardy grasses. The last sliver of sun was a molten coin on the horizon.
Kailani accepted the glass, her eyes on the sky. “This is insane.”
“It’s better at night,” he said, joining her by the railing. “When everything’s lit up. Makes you feel like you own it all.”
She turned to him, her face soft in the twilight. “Do you feel like you own it?”
“Sometimes,” he admitted. “Tonight, I just like the view right here.”
He guided her back inside to the deep sectional couch on the patio. They sat side by side, the cushions swallowing them. He draped a soft wool throw over their legs. The sun was a dying ember now, smearing the sky in deep violets and bruised oranges. The city began its nightly transformation, windows lighting up like scattered diamonds.
Kailani tucked her feet under her, leaning her head against his shoulder. “This is the part where I’m supposed to be nervous, right?”
“Are you?”
“A little. Mostly I’m just… warm. This champagne is really good.”
Henry laughed, a low, comfortable sound. He let his arm settle around her shoulders, his fingers brushing the bare skin of her arm. He could feel the dense, lean muscle there, so different from the softness of the girls he usually entertained. “So, second base. You ever get hit by a pitch?”
She snorted. “Are you kidding? All the time. I crowd the plate. Got a mean bruise on my thigh right now from a wild inside pitch.” She paused. “What about you? As a pitcher, did you ever… you know, nail someone on purpose?”
“Only once,” Henry said, his voice taking on a nostalgic edge. “Guy was showboating, pointing to the fences after a homer. Next time he came up, I put one in his ribs. Not my proudest moment.”
“Did it work?”
“Oh, he stopped pointing.”
They both laughed, the sound easy and mingling with the distant traffic. Kailani turned her face toward him, her expression playful. “You think you could still throw a fastball?”
“I think my arm would fall off. But in my head, I’m still throwing ninety-five.” He squeezed her shoulder. Henry moved his hand, cupping her jaw. Her skin was so soft. He ran his thumb over the fullness of her lower lip. She didn’t pull away. Her breath hitched, a tiny, sharp sound lost in the vastness of the sky.
He closed the distance.
The first kiss was exploratory, a gentle pressure. Her lips were sweet from the champagne, and they yielded under his, then pressed back with surprising force. He angled his head, and the kiss deepened. Her hand came up to his chest, fingers curling into the fine cotton of his shirt. She made a small, hungry noise in the back of her throat that went straight to his gut.
He pulled her closer, the throw falling away. She shifted, swinging a leg over to straddle his lap, her short dress riding up high on her thick thighs. The position put them eye-to-eye. Her weight settled on him, solid and real.
“Fuck,” he breathed against her mouth.
She kissed him harder, her tongue sweeping into his mouth. There was no more shyness. This was the athlete emerging—direct, determined, focused on a goal. Her hips rocked instinctively against the growing hardness in his slacks, and he groaned, his hands sliding down to grip the powerful curves of her ass through the thin dress.
“Henry,” she whispered, breaking the kiss to trail her lips down his jaw to his neck. She nipped at the skin there, then soothed it with her tongue. “I want to make you feel good. Tell me what you like.”
Her words, so blatant and eager, sent a jolt of pure electricity through him. “Just like this,” he managed, grinding up against her. “You feel incredible.”
But Kailani had a plan. She pushed back, kneeling over him, her eyes dark and serious. “No. I want this to be the best you’ve ever had.” Her hands went to the hem of her white dress. In one fluid, muscular motion, she pulled it up and over her head, tossing it aside onto the concrete.
She was naked underneath. Her body was a masterpiece of functional strength. Her breasts were full and high, tipped with dark nipples already pebbled tight from the cool air and anticipation. The lines of her abdomen were defined, a stark topography of muscle layered over a slim waist. Her thighs, powerful from squats and sprints, framed the neat, dark triangle of hair between them.
“Jesus Christ,” Henry exhaled, his hands instinctively reaching for her. He palmed her breasts, his thumbs circling her nipples. She arched into his touch, a shudder running through her.
She leaned forward, kissing him again as her hands worked at his belt. The buckle clinked, the zipper hissed. She pushed his slacks and boxer briefs down just enough to free him. Her small, calloused hand wrapped around his length, and he jerked in her grip, already slick at the tip.
“You’re so fucking big,” she murmured, not with fear, but with a kind of thrilled appreciation. She stroked him, her grip firm and knowing. Then, without breaking eye contact, she positioned herself over him. She used her hand to guide him, notching his head at her entrance.
She was dripping wet. The heat of her was dizzying.
Slowly, with a control that made his vision blur, she sank down onto him. An inch, then two, her body stretching to accommodate him. Her lips parted in a silent gasp, her eyes fluttering shut. He watched, mesmerized, as she took all of him, until she was fully seated in his lap, her ass pressed against his thighs. She was impossibly tight, a hot, velvet fist clenching around him.
“Oh, god,” she moaned, her head falling back. Her black hair cascaded down her back. She began to move, a slow, grinding roll of her hips that was pure torture. Her inner muscles clenched rhythmically, milking him. “You feel… even better than I thought.”
Her rhythm built, each downward plunge more urgent than the last. She braced her hands on his shoulders, her nails biting through his shirt. The athleticism was breathtaking. She rode him with the same powerful, piston-like drive she must use stealing a base—all coiled strength and explosive release. Her breasts bounced with the force of her movements, and he leaned forward, taking one into his mouth, sucking hard.
She cried out, her hips stuttering. “Yes! Right there, Henry. Fuck.”
He let go, giving himself over to her pace. He gripped her waist, his fingers digging into the dense muscle, helping her slam down onto him. The slap of skin on skin, her ragged pants, his own guttural groans—it was a raw, primal symphony against the backdrop of the silent, watching city.
“Look at me,” he commanded, his voice rough.
Her eyes flew open, glazed with pleasure. She held his gaze as she fucked him, her expression one of intense, singular concentration. She was working, striving, making good on her promise. Sweat gleamed on her collarbone. A vein throbbed in her neck.
“I’m gonna come,” she gasped, her rhythm becoming erratic, desperate. “Don’t stop. Please, don’t stop.”
He thrust up to meet her, driving deeper. “Come on, then. Show me.”
With a choked scream, she shattered. Her body clamped down on him in a series of violent, rhythmic spasms. The force of her orgasm tipped him over the edge. He pulled her down hard onto him as he erupted, a hot, endless pulse of release that left him seeing stars, his own shout muffled against her shoulder.
For a long minute, the only sounds were their ragged breaths and the faint pop of the gas fire pit. She collapsed against his chest, her sweat-slick skin sticking to his shirt. He was still buried deep inside her, both of them utterly spent.
She nuzzled into his neck. “Okay,” she whispered, her voice hoarse. “So, was that… was it good?”
Henry laughed, a breathless, utterly disarmed sound. He held her tightly, his hands smoothing over the incredible planes of her back. “Kailani,” he said. “The best I've ever hard.”