Chapter 2: The Pre-Game Strategy Session
The whiskey in Ashlee’s glass tasted like ash. She swirled it, watching the ice cubes fracture the dim, amber light of the bar. Across the scarred mahogany table, Hopey adjusted the hem of her little black dress for the tenth time in three minutes.
“It’s too short, Ash. I feel naked.”
“You look expensive,” Ashlee said, her voice a calm she didn’t feel. “Which is the point. Kevin’s used to expensive.”
Hopey, a sweet-faced brunette from the accounting department, chewed her lip. “I just don’t get why you’re setting me up with your best friend if you’re not into him. It’s weird.”
Because I’m a masochist. Because I need to see if he can look at anyone else the way he looked at me that morning. Because I need to burn this feeling out of me with a magnifying glass.
“It’s not weird,” Ashlee lied, smiling. “He’s my brother. I want him happy. And you’re great. You’re normal. You won’t… confuse him.” She took a long pull of whiskey, the burn a welcome punishment.
“Okay,” Hopey said, unconvinced. “So, what’s he like? What does he… like?”
Ashlee leaned forward, the cold table pressing against her forearms. The low hum of the bar faded into a muffled roar in her ears. She could still taste him. It had been four days. She’d brushed her teeth a thousand times.
“He’s direct. He appreciates confidence.” She kept her eyes locked on Hopey’s. “He’s also used to getting what he wants. So don’t play too hard to get. It’s tedious.”
Hopey nodded, taking mental notes.
Ashlee’s pulse thrummed in her throat. A cruel, jagged idea lodged in her brain. A test. For him. For her. For this fragile thing between them that was now a live wire.
“There is one thing,” Ashlee said, her voice dropping to a conspiratorial whisper. She picked up the thin black straw from Hopey’s abandoned cocktail. “A practical tip. About the… end of the night.”
Hopey’s eyes widened slightly, a flush creeping up her neck. “Oh. I mean, we might not even… it’s a first date.”
“But if you do,” Ashlee pressed, the words like glass in her mouth. “If you want to stand out. To be unforgettable.” She held the straw like a pencil. “He’s… gifted. Proportionally. A lot of women panic. Gag. Make it a whole thing.”
She demonstrated on the straw, her lips forming a loose ‘O’ before tightening. “The trick is the throat, not the mouth. You have to relax your jaw completely.” She mimed tilting her head back, opening her throat. “It’s a mental thing. You decide to take it. All of it. You let him feel that surrender. When he hits the back, you swallow. Actually swallow. It opens everything up.”
Hopey’s face was incandescent with embarrassment. “Ashlee, Jesus.”
“What? You asked what he likes.” Ashlee’s smile felt like a crack in porcelain. “He likes… depth.
“He likes… depth.”
Hopey stared, the cocktail straw demonstration seared into her mind. She swallowed, her throat dry. “Right. Okay. Thanks, I guess.”
Ashlee leaned back, the wooden chair creaking. The damage was done. The image was planted. She watched Hopey fidget, a perverse satisfaction curdling alongside the sharp vinegar of her regret. She paid the tab with cash, the bills slapped down too hard.
“He’ll be here in five. Be confident.” Ashlee stood, grabbing her coat. “Or don’t. It’s your life.” She left Hopey sitting there, adjusting that damn dress in the shadowy booth.
Kevin arrived exactly on time, a blast of cool night air preceding him. He slid into the booth opposite Hopey, his easy smile not quite reaching his tired eyes. “Hopey, right? Ashlee’s friend. Sorry I’m late.”
“You’re not,” she blurted. “Late, I mean. You’re exactly on time.”
He ordered a neat bourbon, his gaze appraising but polite. The conversation stumbled through work, the city, safe topics. Hopey felt the ghost of Ashlee’s instructions between them, a vulgar phantom. Her own nervousness made her bold.
“So, Ashlee says you’re a health nut,” Hopey said, swirling her fresh drink.
Kevin’s brow furrowed slightly. “Does she? I work out. I try to eat clean.”
Hopey leaned in, ignoring Ashlee’s graphic tutorial entirely. Her own plan, sweet and simple, felt more her speed. “You should drink a lot of pineapple juice.” She said it with a deliberate, sunny smile.
Kevin chuckled, taking a sip of bourbon. “Yeah? Why’s that?”
“Makes things taste better,” she said, her face flushing but her voice steady. “Sweeter. I’m a big fan of… sweet.” She let the implication hang, watching his reaction. “I’d want your cum to be extra sweet. For later. When I drink it. Hopefully in your bed together.”
The air between them crackled. Kevin’s glass halted halfway to his lips. He studied her, the polite mask slipping into something more intrigued, more direct. A slow smile spread across his face, one Ashlee had never seen. It was all hunger, no brotherly fondness.
“Is that right?” he said, his voice a low rumble. “That’s a very specific dietary request.”
“I’m a very specific kind of girl.”
The rest of the date blurred. The talk turned darker, more intimate, charged with a promise that had been explicitly named. An hour later, they were in the back of his town car, his hand already high up her thigh, his mouth hot on her neck. The short dress was practically a formality.
In his penthouse bedroom, under the same dim lamp, on the same crisp white linens, it was nothing like Ashlee’s nervous morning. It was deliberate. Hopey, empowered by her own bluntness, was surprisingly commanding. “Show me,” she said, pushing him onto the bed. “Let me see this gift Ashlee mentioned.”
Kevin obeyed, a dark amusement in his eyes. He was fully hard, his erection thick and curving upward. Hopey whistled low, her earlier bravado mixing with genuine awe. “Yeah. Okay.”
She didn’t try the hollowed-cheek technique Ashlee had mimed. She was all enthusiastic, wet pressure. She used her hands, twisting at the base, while her mouth concentrated on the head, lapping at the slit with a focused greed. She remembered her own advice.
“Taste sweet yet?” she mumbled, pulling off for a second.
Kevin let out a rough laugh, his fingers tangling in her hair. “Working on it. Keep going.”
She did, until his hips began to piston upward, a rough, uncoordinated rhythm. “I’m gonna come,” he grunted, a warning.
Hopey just hummed in response, taking him deeper, letting him hit the back of her throat. She swallowed convulsively, and he cursed, his entire body seizing. The hot, salty bursts flooded her mouth. She drew it out, milking him with her lips and tongue until he shuddered and pushed her head away.
She sat back on her heels, looking up at him. She swallowed dramatically, a clean, final motion. A sly smile played on her lips. “Hmm.” She licked them. “Needs more pineapple.”
Kevin stared at her, chest heaving, a look of utterly disarmed shock on his face. He started to laugh, a real, full-bodied sound that echoed in the sleek room. He pulled her up by her arms, flipping her onto her back with a new, possessive roughness.
“You’re a fucking menace,” he said, his mouth descending on hers, letting her taste herself on him.
Downstairs, in the lobby security office, Ashlee watched the blurred, silent feed from the hallway camera outside Kevin’s door. She saw them stumble inside, saw Hopey’s hands already pulling at his shirt. She watched the heavy door close. She sat there long after the screen showed nothing but an empty, expensive hallway, the phantom taste of whiskey and regret on her tongue.