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from-the-clouds · 2 years

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Thinking of a Place (Part IV) - Kendall Roy x Reader

gif that makes me sweat by @televisionchronicles

Part One | Part Two | Part Three | Fic Playlist | Masterlist

Summary: Back working for Kendall, you struggle to fulfill the commitments you've made to yourself. And you join the mile high club 😈

Words: 6.9k.

Warnings: Contains SMUT (minors dni) unprotected sex. Slight potential dubcon (if you squint). Angst. Drug/alcohol use. References to narcissistic parents. Kendall Roy existing and being a deeply sad man. Spoilers for seasons 1-3 of Succession.

A/N: All flashbacks are in italics. In this chapter we explore a bit of the reader character's backstory. I know typically in x reader fics the reader character is left as more of a blank slate for imaginative purposes, but I love writing in-depth and well-rounded characters with unique backstories and histories. So I took some liberties with this character and will continue to do so. I figure we are already writing about an imaginary world, so why not have fun with it?

I think I have this fic all planned out and it will go on for 3-4 more parts. Hopefully ya'll are excited to read! It's a pretty exciting arc, I think. As always, please message, DM, comment, reblog, send asks, let me know what you think of this part!

Lastly, if you have sent me and ask/request the last few weeks, I apologize for the delay. I've had some craziness in my personal life, and have been a lot busier than I was expecting to be. I'm sort of writing what I feel inspired about (mostly headcanons because they are lower pressure) and when I have the energy to. So just know I'm not ignoring you!

Kendall had woken up in many different foreign apartments in his life. He’d spent plenty of mornings after a bender quietly collecting his clothes off the floor under the cover of the faint sunrise, sneaking out without saying goodbye. There was a deep shame he felt each time, whoever he had spent the evening with was just a stranger he thought he’d connected with under the spell of a cocktail of drugs he’d taken. He was always quick to leave, to wash away a night of regrets at his place and curl up in his bed alone.

But when he realized it was you he was wrapped around, snug, comfortable -- he didn’t feel that impulse. The two of you were a tangled mess of limbs, your face buried in the crook of his neck, lips parted but pressed against his skin lightly. You were so soft, so warm. He didn't want to leave you, something about it felt right.

Apparently, you felt differently.

A week had passed since that night at your place. You didn’t change your mind. The next morning, over coffee and scrambled eggs, you explained your decision to Kendall. You simply couldn’t be sleeping together and working together at the same time. It just seemed destined to go awry. He’d reacted pretty poorly, somewhat like a petulant child, but it wasn’t as bad as you had expected. After exchanging some terse words, Kendall stormed out, leaving you alone at your kitchen table, after slamming the door behind him.

Every interaction since then had been strained. Similar to how they had been when Logan first hired you to look after him. Luckily, during the meetings with the shareholders, you’d both been able to put on an act, and appear as a unified front. That was easy, falling into an old habit. But when each meeting was over the walls would come back up, and Kendall would shut himself off again.

When you used to argue, you never cared enough to get hung up on it. But things had changed…you had gotten too involved with him to feel okay about it. You’d let yourself fall in love with him, although you’d never tell him that. Especially now. It was like he was a different person, and it made you ache. If he couldn’t have you the way he wanted, in his eyes, it seemed you didn’t deserve civility.

What motivated you was the absurd idea that someday, if you saw this through as his employee, and helped him get what he wanted, you could resign, and both of you could move forward together. You could know Kendall the way you wanted to. No guilt. No scandal. Deep down, you knew it would never happen. But it was the only thing that you could cling to without being heartbroken.

The hotel you’d stayed in in Los Angeles was elegant, expensive. The suite that had been booked for you and Kendall had multiple bedrooms and a shared living space. You wondered if Kendall had booked the place because he thought you might still be fucking at the time, or just to spite you. If it was to spite you, it was working.

Due to his cold nature you’d spent what little free time you had in your room, avoiding him. You wished you hadn’t spent the week feeling so isolated.

The night before you were set to head back to New York, Kendall left you alone in the suite in the early evening, without saying a word. You knew better than to ask questions. Earlier that day you’d had a shareholder meeting that Kendall didn’t feel good about, getting into a tiff with some millionaire investor while pitching to him in his Malibu mansion. By the end of the meeting, though, Kendall had pulled it together, and all but convinced him the Gojo deal was no good. When he had his moments, you always admired his ability to persuade others with his charisma. Often, Kendall didn’t even recognize how capable he really was.

With Kendall gone, you snuck out to the main living space of the suite, and onto the balcony. After work, you’d gone to a dispensary, and if you were going to be alone all night in California, you were going to get violently high, watch the sunset and listen to Fleetwood Mac.

Your assumption was that he had gone out clubbing and would be gone all night. It was a likely way he might want to drown his sorrows after his perceived ‘failure’ earlier. It didn’t really matter what he was doing, even if it was self-destructive, it wasn’t any of your business. The idea of him snorting coke off the ass of some model-type was still an unpleasant image. You wrapped your arms around yourself in a tight hug, closing your eyes.

The sun had just set, and the lights of the sprawling city lay beneath you. If you tilted your head just right, the six lane highway below you was far enough away to sound somewhat like white noise, or the crash of ocean waves. Wind rustled through palm trees below, the warm air coasting across the loose fabric of the black silk nightgown you were wearing.

The farther you got into the joint, you felt the less you knew about where Kendall was, the better. The less you even cared. Maybe it was time to call Ron again when you got back to New York. Ultimately, you knew that would just be filling a void, but there was something nice about being with someone who required nothing from you, while you expected nothing in return.

You were significantly stoned and growing tired when you heard the door to the suite open. The sun was gone now, a faint bit of orange still lying low on the horizon. It wasn’t even that late, and Kendall was back. But at this point, rather than bother greeting him, you slunk down lower on the patio chair you sat on. If you were lucky, he wouldn’t notice you out here and would go right to his room. Plus, you wanted to finish this playlist in peace, melting into the chair, listening to Stevie Nicks sing.

Would you stay if she promised you heaven? Will you ever win?

“What is this? What are you doing?” You hadn’t heard the sliding glass door open, and now Kendall was standing in front of you on the balcony, hands on his hips.

You crossed your legs, shrugging, letting the black lace hem of the nightgown shift farther up your thighs. Normally, you might have felt a little exposed wearing it in this context. But for some reason, you felt powerful…and maybe a little petty. Let him look. Let him see you. “What does it look like?” you asked, meeting his eyes and taking a pull from the joint.

Kendall crossed his arms over his chest, took a few steps towards the edge of the balcony and draped over the railing, looking at the skyline. He sighed.

“What’s wrong now?” you asked him, fed up with the melodrama.

“I think I fucked it,” he said, shaking his head, pausing. “That meeting earlier.”

You were slightly disappointed, but more than anything, taken aback. This was the most normal he’d spoken to you over the past few days, and no one was watching. You shook your head. “I could tell you thought so. But that’s not how it read to me.”

Kendall looked at you over his shoulder. “No?”

“Yeah,” you nodded. “I thought you were good. Really good, actually. I’d tell you if I thought otherwise.”

“Yeah, I know.”

“No uh,” you coughed, clearing your throat, sitting up a little straighter. “Yeah, maybe you shouldn’t have come on so strong, but once you reassessed, he seemed really receptive. I was actually, uh….” You paused. It was unfortunate, you really didn’t have it in you to be mean right now. And this reminded you of the old days – before you’d both made things complicated – the little debriefs you had after meetings, where you’d give notes on each other's performances. “I was actually really impressed by you. I don’t think I would’ve been able to save myself like that. You did really good.”

Kendall turned away from the view to look at you, as you spoke, and with each sentence, his steely gaze softened slightly. “Uh-huh.”

You nodded, lifting the joint to your lips.

“You should be careful. That shit ruins your ambition.”

You scoffed, rolling your eyes. Of all people, Kendall was not qualified to give lectures on controlled substances. “Okay, dad.”

Kendall gave a warm-sounding chuckle, stepping forward and plucking the joint from between your fingertips before taking a drag. He raked his gaze over your body brazenly, eyes locking with yours as his exhaled a puff of smoke. Swallowing hard, you squeezed your legs together. It was probably in your best interest to get away from him soon, before the horny stage of your high kicked in. Cause he looked undeniable, slightly unshaven, wearing a blazer with a t-shirt underneath. It did look like an outfit he’d wear to the club, even if it was early in the evening.

“So, what, are we talking again?” You asked, eyeing him wearily.

Kendall shrugged, dismissive. “Have we not been talking?”

You tilted your head and stared at him, frowning. “Don’t give me that face,” he sneered. “Isn’t this, fucking, exactly what you wanted?”

“You being awkward and mean?” You shook your head. “I just wanted things to go back to the way they were.”

“Uh-huh,” he looked at you, patronizing. “I think it’s a little fucking late for that.”

You took in a sharp inhale. The fucking bleeding, awful sadness was bubbling up from deep inside where it was buried inside you. Why couldn’t he just be nice to you? After all, he wanted this. Wanted you by his side, to help him do the one fucking thing he’d been dreaming of forever. If you were going to do it, it had to be done right, no messiness. If you were really honest with him, you would cry. So you had to protect yourself. “Well then, you should leave.”

“What?”

“Go inside,” you said flatly, looking over at the door.

Kendall rolled his eyes, until his face grew serious, and you glared at him with fire in your eyes. “Right, okay. Fine.” He stood from where he’d perched on the patio table.

“Close the door, too,” you commanded, kicking your feet back up where he’d been sitting. He muttered something under his breath that could have been ‘bitch’ but you truly didn’t have the energy to do more than narrow your eyes further, watching him retreat to his bedroom through the windows.

The rational side of your brain was taunting you now. None of this was a good idea after, and now you were facing the consequences of your actions. You should’ve known better.

—————

You couldn’t remember the last time you’d been this drunk. Even as you were standing still, situated against the wall, it felt like you were swaying side to side. It didn't feel like you’d drank that much, either. But then again, you hadn’t eaten much that day, between the hustle and bustle of work and then scrambling home to get ready for this stupid gala that you didn’t want to be at in the first place.

You were only there because Kendall wanted to lightly approach some small online newspaper, DailyLancer, about an acquisition. The two of you had been buttering them up, all while one of the owners kept buying you drinks. For the sake of the deal, you felt like you couldn’t refuse. But you weren’t much of a drinker, and now you were pretty far gone.

The event was winding down. You’d stepped away to pee, only to have the heel on one of the cheap stilettos you were wearing snap on your way. Now, standing outside the bathroom, in some dim hallway and all alone, you were leaning forward, cheek pressed to the cool marble wall, a desperate attempt to sober up and keep yourself from toppling over.

Peering around the corner, watching people file out, you pretended to be waiting for someone, when in reality, you were at a loss of what to do. You couldn’t pathetically hobble back to your table in this state, broken heel or not.

But you snapped to attention when you saw a familiar face walking by, slipping behind the corner and out of sight just a tad too late.

“Hey,” Kendall called your name, you heard his footsteps fast approaching.

Fuck. This wasn’t good.

The sight of your boss was like a shot of adrenaline, a cold shower. Despite what you were feeling, you had to pull it together, or at least pretend, in his presence. It didn’t seem like a good idea to let on that you had been overserved. Which was ironic considering the first few years working for him he was consistently under the influence. But things had changed.

“What are you…uh, fucking hiding from me back here?” Kendall asked, ear to his phone, ending whatever call he’d been on and pocketing the device. ”I was looking all over for you.”

You shook your head no, pursing your lips. But Kendall didn’t seem pissed at all, actually. He was wound up, you could see it, pinched between his shoulders. Rigid as usual, but taut with energy. “But uh, fucking awesome news, they’re gonna sell.”

“Oh, really?” you raised your eyebrows.

“Yeah, they’re coming in on Monday to sign the papers. You should, uh, get in touch with the firm to draw up a contract.”

“Of course,” You nodded, smiling, the buzz of the alcohol making it easy. “Wow, that’s great, so much for a soft pitch.”

“Uh-huh, I know, they fucking ate it right up.” Kendall was actually in a good mood. Though it was hard to tell sometimes, because his accomplishments were rarely celebrated. There was always just tentative acceptance on his end. Like at any moment, it could go slipping right back through his fingers. “But uh, I’m gonna head out.”

“Yeah, cool, me too,” you took one step forward, forgetting about your shoe predicament, and it gave out beneath you, sending you tumbling forward. You reached out to catch yourself somewhere, but the only thing available was him, so you ended up breaking your fall with a hand clutching desperately at his bicep. It was distractingly firm. “Fuck, I’m so sorry,”

“That’s fine,” he said. You straightened up, releasing him, but still a little shaken, finding it hard to keep your composure the longer he spent talking to you. Sooner or later, you’d expose yourself. “You okay?” he asked.

You frowned, shaking your head, looking down and gesturing at your shoes.“My heel-,” you wobbled, staring down at the offending piece of footwear. “It fucking broke, like, are you kidding? Just my fucking luck...they were so cheap, I should’ve known better.”

The facade was already shaky enough to begin with, and now it was crumbling fast. Kendall eyed you wearily, listening to the slight slur in your words, the excess profanity that you rarely used. Hiding out by the bathrooms, leaning against the wall, breaking a heel, tripping and falling. You did a good job of hiding it.

“Uh-huh, I see that,” Kendall agreed. “How are you getting home?”

“Uhhhh, I took the subway here,” you said. For some reason, you were having trouble remembering. “I think.”

“Uh-huh.”

“Maaaybe….I should Uber though. I think I can’t walk in these anymore.”

“No, you shouldn’t do that. How about you ride with me?” Kendall said. “You’re along the way.”

“Oh no, Ken, I think I’m not, though.” you mumbled. You couldn’t remember where he was living right now, but it couldn’t be close to you.

“It doesn’t matter. You shouldn’t, uh, be walking home alone like this.”

The area he’d found you, the hallway outside the bathrooms, was conveniently close to the service entrance of the venue, two unassuming double doors that staffers shuffled in and out of. At first you’d appreciated it, a chance to ground yourself in the chill. At some point, it started to feel unpleasant. Cold air was wrapping you up each time someone entered or exited, your teeth chattered lightly before you answered him. “Like what?”

Kendall pressed his lips together, and didn't say anything. “Just come on, it’s not a big deal. Do you need to get your coat?”

“No, fucking….” You looked around as if one would magically appear. “I didn’t uh, I didn’t bring one.”

“It’s fucking freezing out, what do you mean?”

“I just…I didn’t want to deal with a coat. They ruin outfits.” You corrected yourself, shifting your weight, and then teetering again to the side.

Kendall’s hand shot out to catch you, holding you by the elbow firmly. “Uh-huh, yeah,” with his free hand, he pulled out his phone and pressed it to his ear. “I’ll have the driver pull around back okay? You’ll get hurt trying to walk in those.”

“I know and I already fucking have weak ankles, did you know that?” you asked, studying him. “That’s a fun fact.”

Kendall chuckled, a rare smile flashing across his features as he held his phone to his ear. “Uh-huh, yeah, it is fun.” Then he was on the phone with the driver, giving orders.

“Okay, he’s pulling around back, you think you can make it?”

“No, you really don’t have to. Are you sure?” You look up at him, eyes all wide and innocent, pupils blown out. He couldn’t say no to you right now, even if he wanted to. And he didn’t want to.

“It’s fine,” he said. “Come on, let’s get out of here.”

“Okay, I’m so sorry,” you said. “Thank you so much.”

You hobbled forward. Kendall grasped onto your upper arm, rather firmly. It shouldn’t have turned you on to be lightly manhandled by him, but unfortunately, it did. You were drunk and cold and his hand on your arm was warm, steady.

You were leaning into him, lightly, though you weren’t even aware of it, while you waited by the curb for the car. Kendall had never offered to drive you home. There were times when he’d called you a car after staying far too late at work, but that was the extent of it. This was new. At some point, his arm had ventured around your back, resting between your shoulderblades.

The car pulled up and he opened the door, gesturing for you to enter first.

“Thanks so much Kenny, I’m so sorry.”

“Stop apologizing, it’s okay,” he assured you.

“Oof, sorry,” Were the next words out of your mouth as you stumbled into the backseat of the black SUV.

“Careful,” he muttered.

Kendall closed the door behind him, the noise of the city dulled inside the back of the vehicle as you righted yourself. The car began to move and you watched as his eyes darted towards you, a smirk quirking at the corner of his mouth briefly before he grew serious.

“What?” you asked.

“Nothing,” he shook his head, but his smile grew a little more.

“What?” you implored again. Kendall finally looked over at you.

“How much have you had to drink tonight?’

You shook your head. “That’s actually a great question, Kendall. So thoughtful, really. And uhm-”

“Oh, what are you, fucking, uh…filibustering your answer right now?”

“Shhh,” you cut him off, holding your finger out towards him. “I’m getting there, okay? Jason kept fucking bringing me drinks. And I was being a really good employee drinking them because I wanted to help you land the deal. But uh, to answer your question, I kind of lost track.”

“Uh-huh.”

“Don’t get mad at me, okay? This was for you, really, in a sense. And clearly it worked, because, we landed the deal.”

“Right, right.” Kendall nodded. “So, by your logic, you getting drunk at this event is the reason we landed the deal?”

“Well no,” you thought about it. “But like, if you want to frame it that way, then yes, kind of.”

“Wow,” Kendall said. He had turned to face you now, one of his arms over the back of his seat. “What did I do to deserve such a dedicated, loyal employee?”

“That’s a good question, I ask myself that everyday,” you paused, pointing at him. “You should give me a raise.”

Kendall bobbed his head once, and then shifted towards you slightly, his already deep voice lowering. “Maybe I should.”

You were suddenly aware of your teeth chattering, still shivering in the spaghetti-strapped dress you’d worn. Kendall reached forward, messing with the dials on the center console, cranking up the heat.

As the first burst of warm air hit you, you shivered at the comfort it provided. “Thanks so much for letting me ride with you, Ken, you’re so sweet,” you said, unable to stop the words from tumbling out. Obviously, they came from a place of sincerity, but you were usually far too buttoned up to say something so candid.

“Well uh, after the fucking shit I pulled when you started working at Waystar it’s probably time I pay it forward,” he joked. “And I am unfortunately very sober tonight, so at least I can live vicariously through you.”

“But that’s good, you know?” you said. “For you.”

“I know.”

“So good…You’re so good.”

“Wow, strong words” he laughed, avoiding your eyes. “You’re farther gone than I thought.”

“You’re being dramatic,” you giggled. “I am not that bad. I’m just having a good time.”

“Uh-huh,” he nodded, smiling at you fully. You’d never seen him smile this much before, such a rare display of happiness. You would have done almost anything to keep him laughing, even if it was at your expense. “Well, uh, hopefully you won’t remember I said this, but uh…it’s actually pretty fucking cute.”

You saw the sparkle in his eye, the warmth in his gaze. It was clear what was happening. And yes, he was handsome, you’d been attracted to him from the start, but it was hitting you hard. You were crushing on your fucking boss. You were into him. Tilting your head to the side, you narrowed your eyes.

“Oh yeah?” you asked. “You’re cute.”

“Am I?” Kendall cocked his head.

“Oh, don’t fucking pretend like you don’t know it.”

“So it’s obvious?”

“Stop that,” you scolded.

“Stop what?”

“Flirting with me.”

“You’re the one who called me cute.”

“Oh my god,” you rolled your eyes in mock annoyance. “You said it first,” you swatted at his shoulder playfully, and he caught your hand, holding it in place.

“Uh-huh.”

Somewhere during the drive you’d managed to get closer to him, and now you were halfway across the center seat. And because Kendall was already angled towards you, your faces were only inches apart. Far too close to be appropriate. But for some reason, you didn’t pull away.

In fact, you stayed there, studying him, having never been this close. His eyes, fuck, his fucking eyes. They were so beautiful. How’d you never notice that before? About a hundred different shades of green and brown and gold. And they were so wide and expressive, focused entirely on you.

The smell of laundry detergent lingered on his impeccable, dry-cleaned suit, along with expensive cologne, which you’d smelled before on him, but it smelled different then the kind he wore to work. His hand was working up your arm tentatively, giving you the impression that this wasn’t just some one-sided attraction.

You were lucky that your responsible brain had such resilience. Because the answer to the question ‘Why can’t I kiss my boss?’ was obvious enough from the question alone, yet the consequences weren’t registering. But thankfully your brain offered some other alternative reasons as to why not - he was significantly older than you, was still technically married – though, barely. Also this job paid you well, you ran the risk of losing it if you were going to be stupid.

But the universe was really the one who saved your ass ultimately, as the car jolted to a stop and the driver announced your address. As if you both realized where you were, his hand dropped, and you pulled away.

“Uh, are you gonna, uh… be okay getting up there?” Kendall asked, hesitant.

“Yeah, I should be fine,” You nodded, making sure you had all your stuff. “Thanks again, Ken, so much,” you patted his hand, and he looked away bashfully.

“Of course.”

“I’ll see you tomorrow,” you assured him.

“See you tomorrow.”

—————

“What are you reading?”

Thirty minutes into the flight back to New York, and you had fully planned to sit in silence and stew in the tension between you. Of course, as his legal counsel, you’d been forced to be somewhat cordial while walking Kendall through some important documents. But after passing the papers over to him, it had been quiet. Now, the both of you were forced to stick together in the same room, essentially, for five hours. It was Kendall who broke first.

The question was some kind of olive branch, unassuming, an invitation to get to know you better. It was something he might have asked you a month ago, before you both ended up in each other’s beds.

You sighed, flipping over to the cover. “Pretty boring, uh…it’s a self-help book for daughters of narcissistic mothers.”

“Oh,” the slight spark in Kendall’s eye diminished almost immediately. “That doesn’t sound fun. I mean, the book but also…uh, the mom.”

Shrugging, you flipped the book closed. You’d met Caroline Collingwood. There was a chance Kendall himself might benefit from the book you were reading. “No, it wasn’t but…I don’t talk to her anymore.”

“Really? Not at all?”

It was a question you got from everyone. You shook your head. “Basically, not at all.” Besides the very strained phone call that seemed to happen about once a year, usually around the holidays.

“Wow, fucking…” Kendall trailed off. “I mean, my family definitely has it’s shit but that seems a little harsh.”

You were not about to let this man, of all people, give you familial relationship advice.

“It felt that way at first,” you said. nonchalant. “But uh, it just wasn’t really good for me. So yeah, I cut her off completely.” It’d been awhile since you had to talk about this, you felt your chest begin to tighten. And of all people, you weren’t sure why it was Kendall you were opening up to.

Memories flooded back. Your poor, sweet father had always been the peacemaker between the two of you, but his attempts were likened to putting a bandaid on a stab wound. He, himself wasn’t aware that he was a victim, too, years of manipulation had changed who he was to his core, despite your desperate attempts to show him the light. Only for his sake had you entertained making the relationship work, until he passed away shortly after you graduated college. After that, the decision had been easy.

“It was really that bad? That you walked away?”

You frowned, nodding, wondering why Kendall was pressing the issue like this. Going in depth on this topic right now, when you were already feeling very lonely in your life, dredged up all the doubts that you usually knew how to work through easily. But it had been awhile, and you just weren’t feeling equipped to deal with all the feelings. “I wouldn’t be any stronger or smarter for continuing to go into a situation where I know I’m gonna get hurt. It was harder, really, for me to walk away.”

“Uh-huh,” he appeared lost in thought, slinging an arm over the back of the couch he sat on, paperwork scattered around him. You looked back down at your book. “Some of the things you say,” he spoke after a pause. “You’re fucking smart, you know that?”

“Yeah, whatever you say, Kendall.” You snorted, rolled your eyes, about to focus back on your book until you met his eyes, and realized he was being earnest. “I mean, thanks.”

The silence that came between you was a bit more comfortable after that, but you weren’t interested in trying to figure out what he was doing by prying into your personal life. And after that conversation, you were starting to think just a little too much about how lonely you’d been the past few years. Waystar had taken up so much of your time and life, only for you to realize how fragile the perceived home you’d built there was. Unconsciously, you wrapped your arms around your shoulders.

“Hey,” Kendall spoke suddenly, and you looked up. He had his reading glasses on, focused down on the document in front of him that you’d passed off at the beginning of the flight. “What does this mean?” he pointed to a line.

“What’s it say?”

“What do you want me to, uh, fucking read it out loud like this is English class?” he asked, gesturing towards you. “Come over here.”

Normally you wouldn’t have thought twice, but you hesitated. Sitting next to him would close the very purposeful amount of space you had put between the both of you. Any closer and you weren’t able to trust yourself.

“Come on,” Kendall said, but he seemed so engrossed in what he was looking at that it felt…kind of like a normal interaction. Before the mess. Maybe he had actually listened too, and cared about what you had said to him the night before.

So you sat next to him. Pointing to a paragraph in the document, you skimmed it over and explained to him what it meant in layman's terms. You could’ve been having deja vu, but you were pretty sure you’d already explained to him this part of the contract earlier. Listening intently, he leaned towards you, shoulder brushing yours, letting you inhale the scent of his cologne. A memory of your lips on his neck, the taste of his skin salty with sweat under your tongue taunted you, and you allowed yourself once glance at his profile, reading glasses perched on his nose.

He looked so good today, too, slightly tanned from a few days in the California sun, donned in a perfectly tailored suit. It was time to move away.

But as you stood to go back to your chair, he stopped you again. “Hey, hold on. Stay here a second.”

“What?” you asked, crossing your arms.

“Come on, sit down,” he patted the spot next to him and you stared blankly.

“Kendall, what is it?”

A smug look graced his features when he noticed how rigidly you were standing, hands clasped into fists at your sides. “What’s the matter?” He asked, looking up at you over the rim of his glasses. “Are you scared of me?”

Scared of him? You almost laughed. But the comment made you obey him, partly out of spite, as you sank back down next to him.

“What?” you asked him again.

Kendall put one hand over the back of the couch you were on, so it was nearly brushing your shoulder, boxing you in. “I have another question for you…”

He moved in closer, you smelled the mint of his mouthwash. “Have you ever had sex on a private jet before?”

The question was like match, lit in your brain and falling straight to the pit of your stomach, igniting something. But you kept your tone even when you replied. “Kendall,” you said his name calmly, and tilted your head. “What the fuck?”

“What?” He pulled his glasses off the bridge of his nose, folding them with one hand and tucking them in the front pocket of his suit jacket. He was being such a fucking whore. You could tell he knew exactly what he was doing. “Didn’t you, uh, fucking want us to talk more?”

“You think I want to talk to you about this?” you asked.

“Uh-huh, yeah,” he smirked. “Are you gonna fucking answer the question or not?”

“No, Kendall, I haven’t,” you snipped, honestly. “Is that what you want to hear?”

Kendall pursed his lips, shrugged. “Not necessarily. It’s a shame, don’t you think?”

“I can cope,” you said sternly, wanting to retreat, but for some reason, you felt glued to your seat. You were still drawn to him despite all the reasons you shouldn’t be. That couldn’t mean nothing, could it?

“Uh-huh. But uh, aren’t you a little curious?” he asked, just barely a whisper, so soft you were almost straining to hear. But the next sentence came out very clearly. “Don’t you want to know what it’s like?”

“Kendall,” you warned, weakly. “We talked about this.”

“Come on, I can help you, baby,” his voice was so low, all dark and raspy in your ear. He still hadn’t touched you - which was shocking considering how every nerve in your body seemed to be buzzing with adrenaline.

He whispered your name, a silver-tongued serpent in your ear. “We’re all alone. It’ll be our little secret…”

“I think….that you might be the worst person I’ve ever met,” you finally built up the strength to look into his eyes, knowing it’d be your undoing. But at least you were able to follow through with the rest of your sentence, even if you couldn’t stop a sly smile from surfacing along with it. “And that I hate you.”

“Uh-huh, well, maybe I am the worst person you know,” he chuckled. Reaching out, one of his hands rested gently on your knee, radiating impossible warmth. He was closer now, tongue sliding against his lower lip, the part of his face your eyes had been inexplicably pulled towards. “But you don’t hate me.”

You didn’t object. In fact, you did nothing at all, head still angled towards him as he pulled back slightly, one of his hands rising to cradle your jaw, eyes desperately searching yours for some kind of approval, some kind of assurance. Despite all his confidence, they were still tinged with that infinite anguish, so easy to spot once you knew what to look for.

He was right. You were lying.

You shouldn’t have been the one to close the gap and kiss him. You knew so much better than what you were doing. Knew how bad he was for you, right now. Only you couldn’t seem to convince yourself to care. You’d always been drawn to it, that profound sadness. Maybe because you’d always felt it too. Very few people understood. It’d feel better not to carry it alone.

What began as chaste became the opposite rather quickly, he pulled you closer, swept his tongue through your mouth, claiming you swiftly. Catching his lower lip between your teeth, Kendall groaned into you, deepening the kiss.

After some time spent like this, you pulled away to catch your breath. During the makeout session, he’d pulled your legs so they rested across his thighs. And one of his hands, warm and reassuring, had woven in between them.

Kendall didn’t say a word to you, as your foreheads fell together. You watched him slide the whole of his palm up your inner thigh, under your skirt, disappearing from view while you inhaled shakily.

Then, he tugged your tights down just so, pushing your thong to the side, fingers brushing you gently, but not giving you the contact you craved, the contact you realized you needed. You were panting now, slick of your arousal coating the skin between your legs, making you ache for him. “Kendall, please-” you whined.

“You need to tell me if you want this or not.”

“You’re not-” you squeezed your eyes shut. “Not exactly giving me a choice.”

“I can stop,” the lazy drag of his fingertips came to a halt.

“No, don’t do that,” You shook your head quickly. You didn’t want him to stop. “Just…just touch me, please.”

His eyes locked with yours, sealing in the confirmation, and you gave him a short nod. When one of his fingers sunk into you hastily, you stuttered out a sigh of relief. Sucking in a sharp breath, fingers gripping the back of the leather couch you were on, you whimpered as he began to fuck you slowly with the digit.

“That’s it,” he said, responding to the moan you let out. “There’s my good girl.”

He knew you well enough now to really know what got you going. The first time you had had sex was good, but the more you fucked the more he learned about you, almost like he was fucking evolving. He knew just how to touch you, just what to say, knew how to build up a rhythm that easily brought you to the edge within minutes.

His lips locked with yours as a second finger was added alongside the first, opening you up for him at an unhurried pace. After several strokes, his thumb pressed firmly to your clit, giving it some much needed attention. You squirmed, simpered, pressed your hips up and arched your back because you wanted more, so much more of him.

Dragging your mouth away from his slightly, because your lips had locked again at some point, you spoke. “Feels so good, Ken,” you sighed, content.

He inhaled feebly at your words, smiled against the skin of your cheek and kissed down your neck. And then he was off you altogether, pulling away just to tug your tights further down your legs.

“Who even fucking wears these anymore?” he asked, clearly joking, but still irritated. He wasn’t a man who liked to be inconvenienced.

Chuckling, you wriggled back slightly to help him out, as he began to nip and suck at all the skin newly exposed to him, frantic.

Then, the sound of fabric ripping cut through the air, right before he tossed the pantyhose over his shoulder.

Snapping to attention from the bliss of his mouth all over you, you sat up slightly, to find him kneeling on the floor, head between your knees. “Kendall,” you scolded. “I really liked those tights, they were the only ones I had that never snagged.”

“I’ll buy you as many new pairs as you want,” he answered back, annoyed, words muffled into your thigh.

Well, fine. You weren’t going to linger on the issue, especially not when you heard his belt jingling. You couldn’t even lift your head to watch him before he was pouncing on you, hips nestled between your thighs. He stroked himself a few times before teasing you with the tip of his cock, lining up with your entrance. He took great pride in knowing it was him who made you this way, all wet and warm and waiting, writhing underneath him and begging him to take you.

“I want you so bad, Kendall,” you keened, hand on the side of his face, looking up at him.

“You can have me,” he answered, hand cupping your jaw, jerking his hips forward to take you all at once.

You cried out, cut off by his hand clasping over your mouth. “Shhhh,” he warned. “You don't want them to hear, do you?”

Swallowing hard, you nodded. It was easy to forget where you were, miles above any solid ground. You hadn't seen any of the staff since the beginning of the flight, but things could end badly if someone walked in on you like this, speared on his cock, sweating and desperate for him, completely at his mercy.

Nodding, his eyes locked with yours as he began to move his hips slowly, achingly so, fucking you into the seat of the couch, hovering over you. You gazed at him, slack-jawed, as he flashed a wicked smile, one you could tell was real based on how it went all the way up to his eyes. One of his fingers slid into your mouth, and you sucked on it obediently while he watched, groaning as you clenched around him.

Kendall kept you that way for awhile, grinding into you steadily, working you up to the precipice of orgasm, something he knew the feeling of well at this point, after the few nights you’d spent together. He could tell when you were teetering on the edge, your fists balled into the front of his dress shirt, wrinkling it considerably. But neither of you were going to have nice clothes after this. Oh well.

Right as you squeezed your eyes shut, certain the next rut of his hips would be your undoing, Kendall withdrew suddenly. You were about to protest, impossibly frustrated, but his mind was already made up. He pulled you to the floor, leaving you on your knees in front of him, back to his chest, and pressed your head down, bending you over the seat of the couch.

Sinking in gradually this time, he inched forward until his hips were suddenly pressed against your ass, burying himself impossibly deep.

When he spoke, he sounded strained, pinched. He was holding back, tension pinched in every muscle on his body. “How am I supposed to be without you, huh?” he asked, unmoving, tone darkened with lust. “You feel how fucking perfect you are on me?”

“Ken, please,” You groaned, rolling your hips backwards towards him as his hand snaked around your waist, pulling your torso off the couch and back against his chest. He was making you do the bad thing, well, you both were doing the bad thing. But in your current state, you didn’t want to think about that or the fact that you could, theoretically stop it. You didn’t want to stop it. “Not now.”

This angle was perfect, he always seemed to know what positions would get you off, and his cock was hitting that spot deep within you as he drove himself home over and over. You were gonna have rugburn on your knees from being fucked on the carpet. But god, it was so perfect you didn’t care.

“Like that,” you gasped, head falling back against his shoulder when his fingers found your clit and applied the perfect amount of pressure. Your own hand was clasping around the back of his neck, gripping at the collar of his suit. “Please, Kendall, please,” You were begging, for what, you weren’t sure. He was giving you everything you needed. “You’re so – fuck – you’re so good.”

Your words, along with the feeling of your sudden release, throbbing around him as you whimpered his name, sent him over the edge far sooner than he was expecting. Something about the way you were struggling to tell him how good he was must have gotten him over excited, but it didn’t really matter. Kendall came inside you, panting against the back of your neck, praising you all the way.

Kendall clung to you carefully in the aftermath, gently unwinding his arms from around your waist and withdrawing. You squeezed your thighs together as he pressed his lips to the side of your neck, giving you a tender hug and pushing your hair off the back of your neck.

“So good,” he whispered, sighing your name, before standing, the both of you tugging clothing back on and into place. “Can I get you anything?”

Shaking your head, you didn’t answer, the immediate guilt hitting you. A feeling of dread replaced the warmth in the pit of your stomach. You’d done it again, a fucking idiot.

Kendall on the other hand enjoyed being with you like this. But that wasn’t even the part he liked the most. The part he liked the most, you couldn’t give to him, wouldn’t give to him. He watched you adjust your clothing, discard your ruined tights and smooth your hair back into place.

It was only when you returned to your seat across from him, arms crossed to maintain some sort of semblance of dignity, that you said anything at all. “That was a mistake,” you said flatly, no inflection. Empty, barren.

For one moment it looked like you’d kicked him, forlorn look crossing over his features as his eyes widened and tried desperately to connect. But you avoided his gaze. To him, it was clear you meant every word.

Part V

#kendall roy #kendall roy x reader #succession writing #succession #succession hbo #kendall x reader alliance please rise #kendall roy x you #succession fanfic #kendall roy imagine #kendall roy fanfic #i know that reader is kind of dumb for all this #but like #who amongst us wouldnt be putty in ken's hands????#i know i would be #kendall roy smut

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