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ashyyslashy · 3 months

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million dollar baby - kendall roy x f! reader

You go on a blind date with Kendall Roy circa his college graduation and learn the truth beneath his public front.

word count: 4.5k

warnings: language, drug use, sex while intoxicated, piv sex, discussions of infertility

You anxiously drummed your fingers on the back of the car seat in front of you. Bass music throbbed in your ears, barely drowning out the voice of your taxi driver blabbering to someone on the phone. You were used to overeager drivers pushing the speed limit, but this guy seemed to pride himself on going at least 5 under at all times. Worst of all, the heater in his car was broken, leaving you shivering within the fogged-up windows.

You kept glancing down at the “I’m outside” text on your BlackBerry, received a minute ago and counting. Unable to delay it any further, you typed out “I’m just a few blocks away”, and hit send. Several moments later, it buzzed with his response: “Don’t keep me waiting.”

As the taxi slowed towards the restaurant, you squinted out of the window to search for your date. Truth be told, you were wholly unsure what to expect of him. From what your friend Cecily had told you when she set the two of you up, Kendall Roy could either show up to a date wearing a tuxedo or a tracksuit.

You slipped the driver his fare and scrambled out of the backseat before the car had even fully stopped, hurriedly pulling your bunched-up dress down. You cautiously stepped onto the curb in your knee-high boots.

“I’m here,” you texted Kendall as you made your way towards the restaurant’s signage. A bustling crowd was gathered in front for dinner, obscuring your view of the entrance. Heat lamps burned outside with customers flocking around them as they warmed themselves.

You didn’t receive a reply. Your eyes scanning the area, you spied a lone figure standing away from the mass of bodies. He was dressed in a white shirt and black slacks. A cloud of smoke billowed around him, his fingers holding a cigarette to his lips.

He matched the description your friend had provided: average height and a head of coiffed dark hair. As you approached him, his features became more evident, resembling the photo you’d seen. Your gaze flicked from his dark chocolate eyes to his angular nose, his long face bearing an expression absent of any emotion.

“You’re Kendall, right?”

His eyes narrowed, the end of his cigarette crackling.

“Yeah. Hey. You finally showed up.” His voice was deep and distinctly authoritative, speaking to you with all the air of someone at a business meeting.

“Sorry, the taxi was really slow.”

He nodded, taking one last puff of his cigarette before dropping it on the slush-covered cement. He ground it down with the heel of his dress shoe, his movements effortless and fluid.

“Shall we?” he asked, striding towards the entrance of the restaurant without waiting for a response. You were compelled to fall in step behind him - you guessed that a lot of people fell prey to the magnetic force that seemed to orbit him and his family.

He deftly maneuvered his way through the crowd and walked up to the hostess. She didn’t notice him at first, leaning over her coworker in conversation. He cleared his throat abruptly. Her head jerked up, and she blinked a few times in succession as she took in the sight of him and the way he’d forcefully inserted himself into the space.

“Sorry, sir. How can I help you?” she asked, her tone cool.

“Reservation for Roy,” he said in a confident, clear voice, fixing her with an intense stare.

“Alright, let me check that out for you. For 8:30?”

“Yeah. I know we’re a bit late,” he said, placing a pointed emphasis on the last word, “but I know you guys have a grace period. So, I’m hoping we can get seated ASAP.”

A look of brief irritation flashed across the hostess’ face as she picked up two menus. “No problem. Follow me.”

“Ladies first,” he directed towards you, gesturing for you to go ahead of him. You walked behind the hostess, feeling vulnerable to his eyes through the exposed skin on your backless dress.

The hostess guided you to a secluded area at the far corner of the dining room - whether he’d requested the privacy or she had opted to spare herself from Kendall being in her eye line, you were unsure. You thanked her, taking your seat across from your date.

“Can we start off with two Smirnoffs on the rocks?” Kendall asked.

“Oh, I don’t drink. I’ll have an iced tea,” you said quickly.

“One Smirnoff and an iced tea then.” He cleared his throat uncomfortably as the hostess walked away.

“Have you, um, been here before?” you inquired, studying him over the top of your menu.

“Of course. I take all my dates here,” he replied in an indecipherable tone.

“Oh. Haha,” you deadpanned.

“No, seriously, I do.” He paused, before letting out a curt laugh at your disbelieving expression. “Come on. I’m fucking with you, you know that, right?”

“Hard to tell.” Your face burned.

“Yeah, I’ve been here a few times. Cool if I order for the both of us? I know which dishes are the best.”

“Yeah, sure.” You tried to hide the disbelief in your voice.

His eyes studied your face. “So, Cecily wasn't wrong. You’re very pretty.”

“Thank you,” you replied, your glossed lips curving into a hesitant smile.

“I hear you want to go into politics?”

“Yeah, I do.”

“You know, starting out as an ATN anchor wouldn't be so bad,” he said. “I’m sure we could work something out. You know who I am, right?”

“Yup,” you said, forcefully popping the “p”. “Cecily told me all about you.”

Clearly not enough.

“Cool. Now that I’m out of college, I’m ready to start becoming more involved in Waystar.”

He looked at you expectantly, waiting for the ego stroke.

You settled on: “Party days are finally behind you?”

“I wouldn’t say that.” He flashed you his first grin of the night.

“Pardon my reach.” A voice appeared at your shoulder, leaning over you to place the drinks on the table, ice clinking in the glasses.

“Alright. What can I get for you two?” The waiter plastered a smile onto their face and pulled out their notepad.

You slid the iced tea towards yourself and took a long sip, tuning out Kendall’s voice as he recited your joint order to the waiter.

He focused his eyes on you once they’d left, searching your face once again. You weren’t sure what he was trying to find. You got the impression that he was inept at reading people when so much was centered around himself.

“Food should be good,” he said simply.

“Mm.” You were about to excuse yourself to the bathroom when his phone rang.

He flipped open his Blackberry screen and squinted at the number. “Oh. I should take this. I’ll be right back.”

“No problem,” you said with a polite smile, trying to disguise your relief.

As soon as he was out of sight, you flipped out your own phone and furiously typed out a message.

“U didn’t tell me Kendall was the WORST. WTF?!?!”

Cecily’s reply came within the minute:

“No!!!! He is an acquired taste but I thought the 2 of u might click ):”

Your fingers raced to fire back: "He’s so entitled."

“Growing up rich will do that 2 u,” She wrote. “Seriously though, he has a good heart. Give him a chance, 4 me?”

“Ugh,” you murmured to yourself.

“Fine.”

You closed the phone in frustration and stuffed it into your purse, before noticing a pair of black loafers on the ground next to you.

You glanced up to meet Kendall’s eyes. He looked as if he didn't quite know how he’d gotten there. Suddenly so much smaller, his arms curled towards his chest and his phone hung limply from his hand. A lone figure amidst the clinking silverware and pleasant conversation.

“Um, hey..” He said, his voice shaky. His bottom lip was wavering almost imperceptibly. “I’m not really hungry anymore. Can, uh, can we just go back to my place?”

───── ⋆⋅☆⋅⋆ ─────

You shook the grease-soaked paper bag, the remainder of the fries rustling around inside. You balanced it on your lap as you sat gingerly on Kendall’s art deco sofa.

“Do you want any more?” you asked softly.

You were answered by the sound of snorting and sniffing from beside you. Then, a nasally: “Nah, I'm good.”

You tried to keep your eyes away from the lines of cocaine on his phone screen. The two of you had sat in silence on the car ride there, save for him asking your McDonald’s order. It had felt so strange to pull through the drive-thru in one of Logan Roy’s many limos, driven by a stuffy, well-dressed chauffeur.

Kendall still hadn’t spoken to you when you got to his apartment, descending upon bags of white powder he had stashed away. He’d wordlessly offered it to you, and when you vehemently shook your head no, he seemed to interpret that as an invitation to consume more for himself.

You chewed on the fries at the bottom of the bag, feeling like the eating noises were deafening. The apartment was eerily silent, punctuated only by snorting from Kendall’s end of the couch.

“Thanks, for, uh, being chill with this,” he said dumbly, pinching and wiping his nose. You felt relieved to see that all that was left on his phone was the white residue.

“With the… cocaine?”

“Just all of it, I guess. Sorry.” He turned his head to fix you with his penetrating gaze.

You guessed this was as close to an apology for his behavior as you were going to receive. Placing the bag on the table, you hesitantly scooted closer to him.

“Can I ask what happened on that phone call?”

His head snapped away from you again. “I don't really want to talk about that.”

“Okay. I’m sorry.”

“It’s fine.” He slumped back on the couch.

Your purse vibrated from a text. You dug through it for your phone, holding back a dazed laugh as you saw the text that flashed across the screen.

From Cecily: How’s it going??

You switched it to silent.

“Do you want to smoke a blunt?” Kendall blurted.

“Um, is that a good idea? After… You know.” You jerked your head towards the evidence on his phone.

“Yeah, why the fuck not?” He clapped his hands together. “Let’s do it.”

The next thing you knew, you were on his balcony, Kendall’s face illuminated by the skyscrapers and cars passing below. You shivered as the night air chilled you to the bone.

“Here,” he said, shrugging his jacket off and holding it out to you.

“Thanks.” Your joint crackling between your fingers, you moved it into the corner of your mouth. You draped Kendall’s jacket over your shoulders and were immediately greeted by the smell of Dior cologne and cigarette smoke.

“You smoke really sexy,” he said. “Like a James Bond love interest. Mysterious and hot.”

You burst into a mix between a laugh and cough, waving smoke out of your face. “You’re so high right now.”

“So? Doesn’t mean it’s not true.” He inhaled deeply, then blew out a smoke ring. “You do this a lot?”

“Go on dates or smoke weed?” you questioned.

“Um, both, I guess.”

“I’ve only smoked a couple times. With friends. And I go on dates every few weeks or so.”

“All first dates?” he asked.

“Yeah, pretty much.”

“Are most of them bad?”

“Kinda.”

He drew in a deep breath of smoke. “I hope ours doesn’t rank as the worst.” His eyes shined with the vulnerability you’d seen back at the restaurant. As if your opinion held significant weight to him, though you’d known him for less than an hour. As if he couldn't hear one more bad thing tonight.

“No, of course not. There was one guy who I think was, like, into eugenics?”

“What?” he laughed.

“Yeah. Like 20 minutes into the date, he said something like,” you deepen your voice, “Doctors say I have the best sperm they’ve ever seen. So I need a healthy wife who’s gonna bear me a shitload of children.”

He let out a curt laugh as a darkness suddenly settled over his expression. Bringing the joint to his mouth, he took another deep inhale.

“Is something wrong?” you asked, furrowing your eyebrows at his shift in demeanor.

“No, no. I just fucking hate guys like that, you know? The way they treat women, like they aren't equals.” The inexplicable passion didn't reach his eyes, as if he was reciting a script.

“Oh. Yeah, fuck him.” You wrapped Kendall’s jacket more tightly around yourself, an uncomfortable silence hanging in the air.

“Do you want kids?” he asked after a few moments.

“Uh, I don’t know. Not at this stage of life. But later on, with the right person… maybe,” you replied, your voice nearly drowned out by a gust of wind on the balcony. “What about you?”

“Same,”’ he said tersely. He looked like he wanted to say more, but the joint was in his mouth again before he could. The smoke drifted away in the increasing wind. “You wanna go back inside? Getting pretty cold out here.”

“Yeah. I’m sorry for taking your jacket.”

“Don’t be. It looks good on you.” He paused. “You should keep it.”

You laughed in disbelief, sliding it off of your shoulders. You caught a glance at the tag - Saint Laurent. “I’m not going to keep this, Kendall.”

You tried to toss it back to him, but he expertly moved out of the way. Your heart dropped as the jacket soared off the balcony and onto the street below. Scrambling to the railing, you watched helplessly as it was swallowed up by the headlights.

Your knuckles whitened around the railing and you could simultaneously feel the color draining out of your face. “Fuck. Kendall, I’m so sorry.”

He erupted into laughter behind you. “That was a pretty impressive throw.”

You swiveled around and stared at him in shock, your mouth slightly ajar as you imagined the thousands of dollars being flattened by cars below you. “Huh?”

“Hey,” he said, moving forward and placing his hands on your shoulders. “It’s cute how worried you are, but don't stress. I was going to give it to you anyway.”

“Oh,” was all you could manage.

“Come on, let’s just go inside.” He stubbed the blunt out on the railing and you copied his movements. His free hand found yours, cold and shaking, and steadied it as he interlocked your fingers.

You welcomed the warmth that greeted you upon stepping back inside his expansive apartment. You could feel a heady sensation wash over your body, a mix of the heat and marijuana putting you into a hazy state of relaxation. Like Kendall, you didn’t care about the jacket: you wanted to hold onto the comfort that he must come back to every night. You let go of his hand and flopped down onto his couch, flinging off your shoes and closing your eyes.

Cecily’s words appeared behind your eyelids: It’s not his fault he grew up rich.

You wondered if you’d be as much of an asshole as he’d been earlier tonight if you were used to being in a bubble where only your needs mattered. You’d probably laugh too if someone threw a $5,000 jacket over your balcony. His lifestyle was like a numbing agent, keeping him coddled and wanting for nothing. But it seemed like he was trying so hard to pretend that he was serious now that he’d come out of college, with his desire to become involved in Waystar - although you surmised he’d spent most of school in a cocaine-induced stupor.

Did it weigh on him that none of this was his? Or did it not matter where it came from, as long as it was his?

You opened your eyes and glanced over, his back facing you. Your eyes studied the curve of his spine through the fabric of his fitted white shirt. You registered the sound of a needle dropping onto a record, and the thump of hip-hop music filled the room.

“How vintage of you,” you teased.

“I took this player from my dad. He’d probably be pissed if he saw what I was listening to on it.” He turned to you, his eyes alight with supposed rebellion.

He moved closer until he was standing over you, his face a few inches above yours. You rolled over onto your side, looking at him through half-lidded eyes, and realized you wanted to know how his lips would feel against yours. Before you could change your mind, you reached out to cup his face and brought it towards you, brushing your mouth against his. His lips crashed against yours, his tongue exploring your mouth; he tasted unsurprisingly of cigarettes and vodka, the scent of his cologne again filling your nostrils.

He clambered on top of you, his pelvis digging into your hips. You smoothed your fingers over his shaggy hair, gelled strands falling into your face and lightly tickling your cheeks. The long, wavy locks felt so inherently boyish as you mussed them up, providing a stark contrast to his attire. You turned your attention to getting rid of that attire, working open the buttons on his pristine white shirt. His body was pale and lean, a light smattering of chest hair coarse underneath your fingertips.

You felt his fingers travel to the back of your dress, tugging on the zipper and sliding it off of your body. He murmured a compliment against your mouth as he ran his hands up your stomach to your breasts, gently squeezing the flesh.

“You want to move to the bedroom?” he asked softly.

“Mhmm.”

He hoisted you up, guiding your legs around his waist as he carried you to his room. Your lips were fixed to his neck the entire way there, leaving marks on the creamy, stubbled skin.

Kendall deposited you on his bed before going to undo his belt. You sunk into the plush mattress, intoxicated by his luxuries. Reveling in your high, you pulled your panties down, tracing circles on your clit as you watched him finish undressing. He studied you just as intently. Tugging his pants down revealed his hardening cock through the fabric of his Tom Ford boxers.

You dipped your fingers into your entrance in eager anticipation. He tossed his boxers to the side, allowing his cock to spring free, precum leaking from the tip.

“Come here,” you murmured, moving the decorative pillows out of the way with your free hand.

His arms were around you again, his tongue exploring your mouth, his hands traveling across your naked body. You were hopelessly under the spell of Kendall Roy, dying for him to be inside you.

“Please,” you whined.

“Please what?”

“Please, fuck me.”

He tossed one of the pillows at you. “Use that to show me how much you want it.”

You were too far-gone to be irritated at this obvious power trip.

“Okay,” you sighed, obediently straddling the throw. You rubbed your bare pussy against the blue velvet, undoubtedly leaving a trail of slick as you ground into it.

He laid on his side in an emulation of Kate Winslet, pumping his cock as he watched you.

“Are you enjoying the show?” you asked, your question punctuated by a soft moan.

“Very much so.” He smirked. “You can stop now.” You ignored him, continuing to roll your hips against the pillow. He reached across the bed and pulled it out from under you.

“You’re no fun,” you complained, mourning the loss of friction.

“Wouldn’t you prefer me to the pillow?” He put his arms on either side of your torso, boxing you in. You stared up at his face; his expression was hungering for you and for something inaccessible at the same time. If you were sober, you might have stopped, asked him if he was okay. But your drug-addled brain only had one urge: the ubiquitous urge shared by a frat guy hoping to score.

“Yes,” you admitted breathily.

He responded by lightly teasing his cock against your folds. You let out a noise that was a mixture between frustration and lust. He coaxed your legs into the air, putting you into a spread-eagle position. His eyes locking with yours, he slid inside you with agonizing slowness.

You wrapped your arms around his neck, trying to absorb as much of his body heat as possible as he thrusted into you. You were inches away from his dark, intense eyes, feeling so close to him yet so far away at the same time. You wanted to melt into one another so there was not even the tiniest amount of space between you - your flesh turning into jelly, mixing together with his dripping body into one inseparable mass. To share a hive mind, know the thoughts and emotions he was hiding beneath his well-groomed face, the desire behind each movement of his cock.

His thrusts were sloppy, wet, unfocused. His hands held your legs in place, allowing him to push into you ever deeper. You were intoxicated by the animalistic scent of his sweat as perspiration ran off his chest onto yours.

“I’m close,” he murmured, his thrusts increasing in speed.

“Wait, I’m not on birth control,” you protested, momentarily breaking out of your lustful daze. “Pull out first.”

“Don’t worry, I’m shooting blanks anyway.” He said it as casually as if he was telling you the weather, but he was unable to fully mask the fresh pain in his voice. Words faltered on your lips as shock washed over you.

“So can I just cum in you?” he pressed.

“Y-Yeah.”

He stilled, a grunt escaping his mouth as a feeling of sticky warmth filled you up. Cum dripped out of your pussy and onto his pristine sheets as he slid out. He flopped onto his side next to you, facing away.

You stood up and walked over to the room’s adjoining bathroom, locking the door behind you.

What the fuck? You mouthed at yourself in the mirror. You smoothed your hair and wiped away your smeared makeup, trying to remove all evidence of a tryst that had soured. You’d blame the weed and forget all your misplaced desperation and affection for a man who didn’t even have the decency to offer to help clean you up.

You sat down on his heated Toto toilet to empty everything out. When you stood up to flush, you found yourself at eye-level with Logan Roy. He wore a smile that didn’t quite reach the rest of his face, begrudgingly posing in a newspaper clipping from 1980 which marked the billionaire’s founding of Royco. A clipping that was, strangely, framed and affixed above the toilet in Kendall’s apartment.

You imagined Kendall standing in front of this toilet every day during his American Psycho morning routine, staring up at his father. Dad, am I good enough for you? Do I piss like a man? A slave to the judgment of his God. You didn’t know whether to laugh or cry.

You scanned the expensive products littered haphazardly across the bathroom counter before lathering your hands in his Aesop soap. You envied the suds and water washing down the drain of the stone vessel sink, wishing you could disappear as easily. Checking your appearance in the mirror one more time, you unlocked the door and cautiously ventured back into the bedroom.

Kendall’s back was still facing you, his limbs splayed out awkwardly across the bed. He almost appeared to be shaking despite the warmth of the apartment.

“Um, do you want me to stay?” you asked quietly, sitting down on the edge of the bed.

“Whatever you want,” he murmured into the pillow. His voice was thick with tears.

Damn it.

You didn't owe him anything, but you still couldn't bear to leave him like this. Tentatively, you laid beside him, reaching for his hand. He crossed his fingers through yours. You flinched at the sensation of his clammy palm.

“The call I took at dinner, it was the sperm bank telling me my sample wasn't viable,” he said, his voice muffled by the pillow.

Your stomach plummeted to the floor. It was as if all the blanks of the night had been suddenly filled in. Every strange reaction, forlorn look, shifty glance. “I'm so sorry.”

He rolled over to face the ceiling. He stared at it for several moments as if trying to decipher something in the creases of the paint. “It was a stupid dare by my friend to donate it. He thought it'd be funny if Logan Roy had some nobody heir out there somewhere and he never knew.” He sniffled. “Anarchy and all that shit, right? Well, now he won’t have an heir at all. At least not from me.”

“There are other ways, Kendall,” you comforted.

“I know my family. None of them will be the right way.”

You snuck a glance at his red-rimmed eyes, feeling your pull towards his lifestyle fade into obscurity. In his world of excess, there was a constant demand for more, and he was never quite enough. Just laying beside him felt stifling. The massive bedroom was closing in on you.

You waited for him to say something else, but all you heard coming from his side of the bed was soft, steady breathing. You weren’t going to wait for him to regain consciousness. You were going to take this chance to leave, doubting that he’d ever contact you again and feeling guilty about not contacting him first.

You threw one last look at his crumpled form before leaving to collect your purse from the living room. You were left still slightly buzzed, consumed by the odd combination of human emotions that you surmised kept zoos in business: pity for the caged animal mixed with a sick, guilty fascination at the spectacle of it all. As you boarded the elevator down to the ground floor, you pulled your phone out and stared blankly at your chat with Cecily, wondering what the fuck you were going to tell her. Your head buried in your Blackberry, you almost didn’t hear the voice calling out to you as you pushed out of the revolving doors.

“Miss. Miss!” You whirled around to see the chauffeur from earlier waiting patiently by the limo, parked out front. “I’ll take you home.”

“Oh- are you sure?” You wondered how long he'd been waiting there.

“Yes,” he said tersely.

“Okay, thank you so much.” You clambered into the car, reciting the area of New York City where you lived. You were unsure whether you appreciated this gesture or felt like you were being shuttled away like just another hook-up. But you were just another hook-up, you reminded yourself. You were a blip on Kendall’s radar, a chance encounter, a rando he’d told too much. All you could do now was forget.

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