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Stick Around (and watch me fall apart)

Summary:

“But if this is gonna work, I need you to do something for me."

“Sure, yeah, of course. Anything,” he answers immediately, and she can’t help but chuckle. He's so eager to please, it's kind of adorably pathetic, or maybe pathetically adorable.

“I need you to forget about your dad,” she says, quiet but firm. "And your brothers, your sister, the company - everyone outside this room. None of them matter, okay? All that matters is you and me." She takes his hand, holding eye contact as she interlaces their fingers together. "Can you do that? Can you be good for me?”

“Yes, yeah, I can - I can do that. Be - be good." Kendall swallows, a noticeable flush on his face as he says the words. "For you.”

Okay, Naomi can definitely work with this.

Notes:

getting way too deep in my feelings about sad rich assholes wasn't on my 2023 bingo card but here we are I guess.

In my new occupation as a Kendall Roy Apologist™️ I lowkey thought these two were cute so I wanted to explore the relationship a bit more? idk exactly what this is but I had fun and maybe you will too.

Thanks for stopping by and I would love to hear your thoughts! 💜

(See the end of the work for more notes.)

Work Text:

Naomi Pierce is fully prepared to despise Kendall Roy. 

Logan Roy built his empire on twisting and perverting her family's most private and painful moments into cheap entertainment for the masses, so it’s hard to imagine any of his offspring having much more of a moral compass. She's met more than enough Kendall Roys to know the script: he’s the bland, obedient puppet, speaking in pre-rehearsed (and probably pre-daddy-approved) soundbites and buzzwords. Naomi just has to smile and look interested enough not to sever any potential future value in their acquaintance until she can ditch him. 

Except, somehow, they end up going off-script.

Kendall manages to be a surprisingly tolerable conversational partner - not that he has a ton of competition, next to Roman's aggressive obnoxiousness, or Shiv’s calculated calm that fails to mask her metaphorical stench of smugness. But there's something disarmingly earnest about him, even when the things he's saying are blatant bullshit. Something about the way he leans in that makes her feel like they're the only two people in the room, while he spouts off about synergy and the temperature, peppered with slang that’s at least two years out of date and half a decade too young for him. It clicks that he doesn’t just want the deal; he doesn’t just want to fuck her; he wants her to like him. To think he’s cool, which is…more endearing than it probably should be. 

(That or he’s just desperate to get fucked up and/or away from his family, which Naomi can equally appreciate.)

So they sneak away, snickering like naughty schoolchildren, and she has a revelation: Kendall Roy might actually be fun, when the spark behind his eyes of anything resembling a personality isn’t immediately snuffed out by his dad’s disapproving glare. He might even be kind of charming, a few lines in when he stumbles over his words like his mouth can’t catch up with his brain, telling her about how he’s going to shake up Waystar and revolutionise the tech industry and a secret upcoming project that he makes her promise to keep on the DL because it’s on a strictly need-to-know basis, but let’s just say he’s pretty sure he's gonna blow some fucking minds.

Making out in the helicopter after almost taking an impromptu night flight feels like a natural ending; something to look back on and cringe-laugh, after the deal goes down in flames along with any prospect of an uneasy family alliance.

But Kendall - to her mild, but not unwelcome surprise - sticks around. He texts, he calls, he sends her flowers. The guy's kind of intense, but honestly, Naomi doesn't hate that. It's been a while since anyone lavished this much attention on her, like she's special, not just another interchangeable old money socialite.

And maybe even more surprising - she likes him too, the more she gets to glimpse under all the layers of self-conscious posturing. She likes the Kendall Roy who has to ask for her preferred angle of dick pics, whose non-fake smile is lopsided and goofy like a robot learning how to process emotions, but lights up his face as if she’s the centre of his universe. 

She likes it a little less when he switches from all to nothing, silent for days - sometimes weeks - after being sucked back into the black hole of patented family bullshit. But she gets it: they're in the midst of a potentially company-destroying scandal, a bullet Pierce just barely dodged.

If Naomi cared about the optics half as much as most of her family, she'd have cut Kendall off by now, before their fun starts to get too messy and complicated, even compromising. Definitely before tagging along on his dad’s yacht to bear witness to whichever poor sucker ends up being the sacrificial lamb - but she's pretty sure even Nan wouldn't begrudge her the schadenfreude of how much her presence probably pisses Logan off, reminding him of the one time he couldn't get what he wanted by throwing enough money at it.

Unlike everyone else present, though, she's not here because of Logan Roy. Kendall practically pounces on her the moment she boards, whisking her away to his room before she's in danger of having to exchange tense pleasantries with any of the Waystar team. 

"So, you saw it, right?" he asks, a hopeful gleam in his eye like a kid asking if she was watching his totally sick cannonball. "The hearing?" 

“Hmm, did I see it, probably the most important moment of your career to date that possibly the whole country was watching? Yeah, I might've caught some of that.” She grins, taking his hands in both of hers and giving them a reassuring squeeze. "You killed it. Thank god they saved the best for last.”

"Well, I wasn't gonna say it, but - fuck it, yeah, I think maybe I did?" Kendall laughs, practically glowing from the compliments. If he had a tail, it'd be wagging. "I think it's all gonna be good, Nay. As soon as we…" he hesitates, glancing towards the door as if his dad might barge in at any moment, "figure this out, we can go away, just fucking - disappear somewhere, just you and me. We can hire an island - buy an island - go totally off-grid, anywhere you want."

It's hard not to get caught up in his excitement, swept along in this wave of optimism as he slides his arms around her waist, pulling her back onto the bed with him. They sink into a kiss that's sweet yet fierce, needy, hungry. 

“You did so good, babe,” she tells him in between kisses. “I’m so proud of you."

“Yeah. Yeah." Kendall makes a rough, pleased noise - that might be a new one, interesting - and pulls her tighter against him, covering her neck with hot kisses. "It's all good, gonna be so good. I got this, I can do this, Dad -"

Naomi freezes.

Kendall freezes.

The world around them seems to freeze as their eyes lock in a moment of stunned silence.

What did you say?”

"I, uh, what? I don’t - I didn't…" He laughs, shakily, so completely failing to conceal his expression of oh shit that it's almost funny. Almost. “It’s nothing, c’mon, can’t we just -"

“No, we can’t just,” Naomi snaps, slapping his hand away when he reaches for her again. But the revulsion and frustration that twists in her stomach isn't as much at him as herself - because it's not like she didn't know what she was getting into, dating the fucking poster boy for daddy issues. Maybe she’s the idiot for letting it get this far, for starting to think that they could ever be more than another drug-fuelled poor decision.

“You know, I probably shouldn't have come here." She stands up, smooths down her dress. "This is your family shit, I can't be part of it. You need to focus on figuring this out - maybe call me, when your dad decides…"

“No, no, Nay, wait, don't - you can't go -" Kendall flounders - both verbally and physically - scrambling to catch hold of her wrist before she can make it to the door. "It's not, I really want - I fucking need you here, okay?"

Naomi tugs herself free instinctively, but when she turns she's hit by the naked vulnerability in his eyes - it's almost too much to look at, like staring directly into the sun. An open admission of weakness that’s anathema in the world they've both grown up in, where emotions are either concealed at all costs or deployed strategically as weapons. But the way Kendall looks at her now doesn't feel fake or manipulative - it feels real, and raw, and like something that might blow up in her face if she doesn't handle it with care.

She sighs, sitting back down on the bed as she turns to face him. 

“Ken. Babe.” She places a hand on his cheek, her expression softening. “If you’re thinking about your dad when we’re about to fuck, I can't -" 

“I’m not! I’m not thinking about - it's not like that, I swear." He grabs her wrist again, turning his head to kiss her palm. "Everything is just…kind of a huge fucking mess right now, you know? And - and maybe, I guess it's also just been a while since I received that kind of, uh…" he hesitates, choosing his words carefully like he's delivering a business pitch, "positive feedback?”

Naomi nods slowly, arching an eyebrow. She doesn't need her Roy-to-English translator to figure this one out.

"Okay. Feedback, huh?” Maybe she can work with this, she thinks, lingering on the word as her lips curve into a knowing smile. "If that's what you want, why didn't you say so?”

She leans in, their faces drawing closer - but just before their lips touch, she pulls back.

“But if this is gonna work, I need you to do something for me." 

“Sure, yeah, of course. Anything,” he answers immediately, and she can’t help but chuckle. He's so eager to please, it's kind of adorably pathetic, or maybe pathetically adorable. 

“I need you to forget about your dad,” she says, quiet but firm. "And your brothers, your sister, the company - everyone outside this room. None of them matter, okay? All that matters is you and me." She takes his hand, holding eye contact as she interlaces their fingers together. "Can you do that? Can you be good for me?”

“Yes, yeah, I can - I can do that. Be - be good." Kendall swallows, a noticeable flush on his face as he says the words. "For you.” 

Okay, Naomi can definitely work with this. 

“Yeah? Good." She smiles, before finally closing the gap between them to reward him with a kiss. It's just a fleeting brush of lips, before trailing more light, teasing kisses across his his face, his cheeks, the bridge of his nose.

“You’re so good, Ken," she murmurs, her breath teasing the tender spot just below his ear. "You’re fucking beautiful, did you know that?”

“I - uh…”

“You're not supposed to answer, babe.” She nips playfully at his earlobe, feeling him shudder as she pushes him back so that she's half on top of him, straddling his lap. “Just…trust me, okay?”

She leans back, drinking in every detail of his face. He gazes up at her with a kind of awe; not just desire, but need. It stirs something in her, a sense of power that both excites and scares her a little. Like she has the ability to save him - or to shatter him.

"And you know what else? You're better than all of them. All of this bullshit." She kisses her way down his neck to his chest, deftly unbuttoning his shirt. He smells good, salt and sea air mixed with some expensive cologne, maybe a splash too much, but it's for her. Right here, right now, Kendall Roy is all for her. 

“Nay, I - fuck - " He jolts, letting out a low moan when she flicks her tongue against his nipple. She laughs softly, warm breath teasing the tender skin.

“Seriously,” she says, lifting her head to meet his gaze again. "I know you think you have to be like your - the whole macho alpha male bullshit. I know you try so hard - but you're not that guy. You're sweet. You're sensitive." She runs her hands slowly down the newly exposed skin, feeling the unsteady rise and fall of his breath. "And that's who I want. I want you to feel. I wanna feel you. I want you to feel me."

“I, uh - I want that, too. I feel,” He tenses under her hands as she caresses his chest and stomach, glancing down like he can't bring himself to meet her eyes. "God, I feel so fucking much, Nay. But I don't know if it's - that I should…" 

He kisses her instead of finishing the sentence, cupping her face in his hands as if she might slip through his fingers at any moment.

“You should, Ken," she murmurs against his lips, breath intermingling, foreheads pressed together. It feels intimate, almost chaste…if she couldn't feel how hard he is already, just from this, from her words. She wants to make him come apart, with nothing but sweet words and gentle touches. "Let it out. I can take it." 

She rolls her hips, teasing him through the thin layers of fabric and earning a louder moan. His hands grip her hips, trying to get more friction, but she keeps the pace deliberately slow, rocking against him just enough to draw out deliciously needy noises.

“Wait, wait - let me…” Kendall squirms underneath her, fumbling at the hem of her dress while trying simultaneously to tug down his pants, and not really succeeding at either. Naomi catches his hand before it makes it between her legs. 

“Not yet,” she says. "Let's just…go slow. This is good." 

Maybe there's a part of her that enjoys keeping him on the edge a little too much, curious how long it’ll take for him to break and beg for more - but it's not pure sadism. Perhaps ironically, not letting him fuck her feels somehow more intimate, closer than they've ever been. More aware of everywhere they're touching, the duelling desire and frustration in every shift and sigh and moan. She can take her time taking him apart with the softness he so desperately needs but doesn't know how to handle.

"O-okay. Yeah, I can…" Kendall's breath hitches as she rubs up against him. "So you want me to - is this…?" He drops his gaze again, flushing with the humiliation of having to ask for permission to hump her leg like a horny teenager. 

Fortunately, Naomi takes pity on him. 

“You can do anything.” She kisses his forehead and he pulls her to him, pressing his face into the crook of her neck. His breath is hot on her neck, half-muffled moans and gasps in her ear as lust overtakes shame and he starts to move faster, grinding his still clothed cock against her thigh. 

“Fuck, Nay - you feel so -”

“Let's go,” she interrupts, breathlessly, recklessly. “Today. Now. Leave with me and let's go somewhere good. You don't have to play their bullshit game.” 

Kendall's head jerks up as she says it, his eyes huge, and for a moment he looks like he's about to burst into tears. Like a dam struggling to hold back so many conflicting emotions - desire, guilt, ecstasy, shame - that if it breaks, might drown them both.

“Yeah, yeah - okay, fuck ‘em,” he pants, nodding frantically. "I wanna go, I do, I just - fuck, what if I -”

She takes his face in her hands, forcing him to look at her before he can turn away again.

"He doesn't deserve you." The words are quiet, but they come with such fierce sincerity it surprises Naomi herself. Like if she tries hard enough she might somehow be able to burn through almost 40 years of denial and conditioning. Set him free by staring deeply into his eyes while shamelessly grinding against his cock. "You know that, Ken. He wants you trapped in his shadow - they'll never see you, all the amazing things I know you can do. Come with me and be -” 

Be different, she might have finished. Be better. Maybe even be loved.

But before she can get that far, Kendall breaks. His body jerks against Naomi’s as he cries out, muffling the sound by biting down on her shoulder. She winces, but not hard enough to pull away as he clings to her, pressing messy kisses to the mark he left, her neck, her face, whatever part of her he can reach as he rides out his climax. 

“Fuck,” he sighs, the word sounding like a simultaneous curse and a prayer as he falls back against the bed. He glances down at the very conspicuous stain on his very expensive pants with an expression like his own dick just voted against him at a board meeting.

“I didn’t, uh - I wanted to…”

Naomi just bites back a giggle. 

“Sssh, hey, shut up. You did great." She rolls off of his lap and kisses the side of his head, stretching out her legs on the bed. Kendall leans his head on her shoulder and they stay like that for a moment, quiet but for the faint sounds of the waves lapping against the yacht (and the fainter, less tranquil sounds of Tom and Shiv bickering a few rooms away).

A wave of emotions washes over her: this tenderness, even protectiveness, but with a lingering bittersweet aftertaste she's not quite sure how to process. Like she wants to hold onto this moment - hold onto him - while feeling it slip away, sinking under the sense that this, whatever they have, might be too fragile to survive out there. 

Naomi knows, and Kendall knows, even if neither of them will say it - he won't leave with her. Not with the sharks circling outside that door, deadlier than anything in the ocean. 

Kendall huffs out an odd noise, and she can't tell if it's a chuckle or a sob until he shifts so he's the one leaning over her, the playful spark back in his eye. 

“Whoa, wait a second - who said I was done with you?”

So she lets him flip them over, landing on her back with a giggle before he claims her mouth, intent on covering every inch of her with kisses like he's got something to prove. She lets him push her legs apart and eat her out like she's his last meal, hungry for her moans and gasps, her hands tugging at his hair and her fuck yes right there don't stop it's so good, he's so good, so good for her. 

Naomi can’t hate Kendall Roy, and she doesn't know if she can love him, and she's pretty sure she can't save him. 

But in the moment, she can almost believe that they can stay afloat - maybe even long enough to make it back to shore.

Notes:

thank you so much for reading! comments and kudos are always very much appreciated 💜