#kendall x reader alliance please rise!!!!

[from-the-clouds]

lost in the fire - kendall roy x f!reader

| masterlist | succession sideblog: @kendollroyco | my kendall playlist

chapter summary: your boyfriend works too much. a oneshot, but if we're being real, i was thinking about kendall and the reader from thinking of a place, because i miss them. pairing: kendall roy x f!reader words: 4.6k warnings: SMUT (18+ only). soft dom Kendall. Somewhat unhealthy/jealous/co-dependent relationship but this is a Succession fic so like…what do we expect? Alcohol consumption - I don't know what Kendall's definition of sobriety is but he drinks a cocktail in this. a/n: i'll get back to tlou but i've had this partially written for like a year at this point. It started out as more of a manic Ken on a power trip type of fic but then it got really soft and fluffy because I am feeling touch-deprived lately so I’m sorry if I didn’t deliver enough evil ken for ya’ll. :/ OOPS!

**ALSO! I got rid of my taglist. Please follow @ftcwriting and turn on notifs if you would like to be notified when I update my works :) **

"We're like the Lewis and Clark of fucking." - Kendall Roy

Teetering down the hallway, you attempt to quell the outrageously loud click, click, click of your stilettos against the marble floor by shifting most of your weight into the ball of your feet and shuffling forward. It only makes it harder for you to balance while you attempt to put on the flashy gold hoop earrings your friend had insisted you’d wear. Of course, being quiet didn’t really matter, because you were the only person inhabiting the Hudson Yards penthouse. 

As usual, you are running late. Famously, you always underestimate how long it will take to get ready for social events – your friends could attest to that. It is a bad habit that, despite years of trying to correct, you can never quite shake. 

Beelining for the double doors of the multi-million dollar home, you are interrupted by your name being called out in a sing-songy voice. There is a blur of movement out of the corner of your eye, and you turn towards the familiar sound to find your boyfriend rounding the corner, a drink in hand.

The sight of him at home is rare these days, that for a second, you aren’t even sure if it’s really him. Maybe the place is being  haunted by an eerily similar lookalike, or it could be some new ridiculous billionaire technology that he’d invested in– holographic messaging, or something similarly dystopian that you’d roll your eyes at when he tries to explain it to you. It’s fuckin’ next level, I’m telling you. I’m a fucking tech pioneer. You can practically hear him trying to sell you on it despite your distaste.

“Ken?” you cling to the clutch under your arm, unable to stop the shit-eating grin that works its way onto your face. “Hey. When did you get home?”

“Hey yourself,” he answers, poorly hiding a bemused smirk behind Baccarat crystal. “I just got in.”

That much was clear, even though his briefcase and coat had already been cleared away from the table in the entranceway, and his suit jacket draped over the back of a barstool. “Are you going out?” He lowers the tumbler and leans against the counter, but still keeps it close, one finger sliding along the rim. 

“Yeah,” you approach Kendall cautiously. “...did you get my text? I thought I’d get ready here, we’re going to that place around the corner.”

He’d given you a key to his flat, even though the relationship was still pretty new – but decidedly not that new, given your history. Things were still moving quickly though, if you compare him to your past flings.

Kendall’s eyes close briefly in recognition, his brows pulling together as though he is scolding himself. “Oh, uh-huh, yeah….right.” It’s then, and in closing the space between you, that his haggard appearance becomes clear. You’re one of few who would probably even notice it. To the untrained eye his white dress shirt is impeccable, crisp and stark as usual – save for the lack of cufflinks, which you notice he’s discarded on the counter alongside his drink. His tie is still fastened tightly around his neck in a perfect half-Windsor. But salt and pepper stubble is sprinkled across his jawline, faint red hazy in the whites of his amber eyes. 

Work has consumed him in the last few weeks. It’s been nonstop. And he is still home earlier than you have expected, even though the sun had gone down long ago.

Kendall’s hand wraps around your waist and you lean against him, accepting his affectionate peck on the cheek. “Hey, honey.” The cedar notes of his cologne, the acidity of the vodka on his breath, and the weight of his arm around you makes your stomach flip, even as he draws back, releasing you so he can sit on a barstool. It’s probably for the better, as the impulse to throw yourself into his arms and abandon your plans will become impossible to resist if you don’t leave soon.

It would be a lie to say his career hasn’t put a strain on things lately. Business trips, dinner meetings, weekend conventions all seem determined to keep him away from you. For the past few weeks, you’ve been deprived of him, forced to accept only minutes of his time – mostly sweet nothings and apologies whispered as falls into bed beside you, then presses of his lips on your cheek, still half-asleep in the early hours of the morning as he leaves the next day. You have been forced to savor those moments, even though they are hardly substantial. But you know yourself, you aren’t better off with someone else. He has always been what you wanted.

Still, lately you have been thinking about all his failed past relationships. There is certainly a…pattern. You’ve seen enough, and sometimes it feels like you are purposely ignoring the signs – Watch Your Step!, before falling into a pit of daggers. 

He needed a break or he’d burn out, but you’ve learned when to bite your tongue and save those suggestions for when you are sure they won’t erupt. And you both aren’t always good at keeping arguments good-natured. 

Kendall shifts in his chair so he can look you up and down – this time up close. “Is this what you’re wearing out?”

“Uhhhh, yeah,” you answer hesitantly, feeling your face heat up. 

“Turn around,” his resting facial expression is already kind of indignant, but you can tell right now that he’s definitely frowning. 

“Excuse me?”

“You heard me,” he says. “I want to see.”

You shrug, but obey, unable to hide the way your lips quirk when you are back facing him again, hands on your hips. All you have to do is read the look on Kendall’s face to know that he doesn’t approve. And even though there is no way in hell you are going to change, the slight blaze in his narrowed eyes makes you think this is about to become a controversy. 

“Do you have a problem?” you ask, feigning innocence, glancing down at the getup. The red dress barely covers your ass – is far more revealing than anything you’d normally wear, accompanied by stiletto heels that lace up your calves. Sure, it’s a lot, but you look good, and you’re going out. 

“You’ll definitely be getting a lot of attention,” he conveniently doesn’t answer your question.

If you weren’t wearing lipstick, you would’ve bit your lower lip to keep your composure. Instead, you tilt your head and give him a coy smile. “You should come with me.” 

Kendall glances down at the countertop and shakes his head, the comment causing him to drop the subject of your attire entirely. “I can’t. I’ve got a meeting first thing.” To be fair, he avoids the club scene most of the time, so it’s not a well-thought-out offer. Too much temptation. “But you look good,” he concedes. 

“A work meeting on a Saturday?” you ask, ignoring the compliment. “Fuck,” you reach to take a sip from his tumbler. The vodka he keeps here is always chilled to perfection, so smooth it tastes like it’s melting off a glacier. “It’s that bad?”

He takes the beverage from your hand when you return it, shrugging before throwing the rest back, then standing to pour another. “Just the usual, la-dee-fuckin-dah….corporate bullshit.”

You frown and stare at your shoes, flexing your foot and inspecting its soles.

“Those heels don’t look very comfortable,” he remarks as he passes you.

“They aren’t.”

“Well then I’ll guess I’ll have to take you shopping to replace them.”

You feel yourself flush. “Let me know when you can fit me in your schedule.” 

“Uh-huh,” Kendall ignores your jab, changes the subject. “How’s your job?”

“Same as yours. La-dee-fuckin’-dah corporate bullshit,” you repeat his words from earlier, lowering your voice slightly to mimic his cadence of speaking. 

The sound of his warm chuckle makes your stomach flip again. “You want me to, uh, pour you one?”

“No, I should probably get going.” You sigh, pulling out your phone to text your friends that you are running behind, and you hear the clink of ice against crystal.

Then, his voice, deep and husky, directly against your ear. “Who’re you texting?”

You jolt in surprise at his sudden proximity.  “Fuck! Sorry,” you clear your throat. “Uh….the group chat.”

Kendall’s arm reaches past you to place his drink on the counter, and you feel his fingertips brush the hair away from the nape of your neck. Then, his lips follow, pressing there gently, his thumb trailing down your arm and then back up again. You shiver at the contact, and it dawns on you how touch-deprived you are.

“Pretty girl,” he murmurs against sensitive skin. His hands land on your shoulders and begin to knead at the taut muscles there. You try to keep yourself tense, even as you feel your phone slipping out of your hands, the drafted text all-but forgotten.

But instinctually, you shift backwards to feel the weight of his chest pressed against you.“You’re all wound up,” Almost chastising. Every part of your body below your bellybutton clenches. It’s those hands, his hands. Hands that used to wrap around your throat, thread into your hair, hold your wrists in place. Pin you down, spread you open…. While you think about them, you let him work at the tension that he is partially responsible for, nodding and letting out a long exhale.

“Just a little.”

“When are you gonna quit that job?” he asks you.

You first, you want to say, but let the retort die before it could leave your mouth. “Hmmmmm,” you pretend to mull it over, but you’re only half-aware of things he’s saying to you. “I don’t know.” 

“What kind of uh, feminist would I be if I let a girl as hot as fucking you have to worry about a job?”

You can’t help but snort, turning your head so his forehead bumps against your own. “Is that how feminism works?” 

“Uh-huh,” he chides, breath tickling the shell of your ear. “Fucking whatever. I wish you’d just let me look after you.”

You are unable to find your voice to answer, because you remember through your needy haze that you are running late, and when he says things like that, it certainly doesn’t help you regain composure. It’s only after you straighten, trying to pull yourself out of the trance he’s worked you into, that you discover how close he has pinned you to the countertop.

“Ken-” you try to protest, but the way it comes out sounds more like you’re pleading.

“What is it?” Kendall asks, returning his lips once more to your neck, beginning to work them tenderly up the column of your throat, which makes it impossible for you to finish the rest of the objection. “I’ve missed you so much,” he pulls you back against him by your waist.

“Me too,” you sigh. “But I-,” you’re cut off when he grinds against you, already half-hard, and your pelvis hits the granite lip of the countertop. It hurts, just for a second, but the pain is quickly replaced by warmth. Kendall pulls his hands away and you’re only held in place by his hips, the metal of his belt buckle cool against your sacrum. The dress you’re wearing is so thin it feels like there’s nothing separating him from your bare skin. 

“You what?” he prompts when you remain silent. You know him well enough to hear the self-satisfied smirk on his face, and his nails rake up and down your arms.

It’s a little petty, but you are hesitant to give yourself over so easily to him. To abandon your evening, just because he’s finally decided to see you at a reasonable hour. Of course, if your friends knew you were late because you were with him, they wouldn’t care. Kendall had been a well-kept secret until it was impossible to deny his existence in your life. But they were all a little too supportive of the relationship, since it meant they suddenly had guaranteed access to any club VIP section - and you perpetually pick up the bill. Not to mention the first-class, luxury accommodations they get on girls trips. 

There was more to it than just being late, though. You had always been willing to do anything for him, even before you were dating. He told you to jump, you asked how far? He gave you one pleading look from underneath those thick lashes – and you folded. And Kendall is very aware that he’s your weakness. So you constantly try to convince him otherwise, lest he get too comfortable. And really, after his neglectful behavior, did he really deserve you without any opposition?

“Kendall,” you manage to turn slightly. “I’m going to be late.” Wriggling some more in his grip, but it’s only enough to bring you face-to-face, looking up into his stormy eyes. 

He studies you carefully, like he might let you leave if he senses enough conviction. “I don’t care.”

You might’ve laughed, if it weren’t for how stern he sounds. It almost scares you. Almost. Hoping to soften him, you fit your thumb into the dimpled fabric of his tie, and use it to drag him forward, offering a tender kiss on his cheek. Returning the embrace, his stubble scratches your face as he smiles against you. He reaches behind you for another sip of his drink and his unoccupied hand slides down your back, squeezing your ass through the silky fabric. 

You are burning, fire licking up your arms, your neck, your face. It’s too much, to have him so close and not be able to have him. All the tension building with nowhere for it to go. When he pulls back, you lean forward.

It’s a little rough at first, because you are so desperate, tasting the vodka, drawing his bottom lip between your teeth. Kendall is the one who softens you, cradles your jaw to draw you closer, opens his mouth and deepens the kiss, so deliberate and practiced that you’re unable to speak when he pulls away. 

“Tell me something,” full lips so close to yours that they brush your own when he speaks, your eyes fluttering shut. His touch coasts up your sides, up your arms, landing on your shoulders. “Who are you showing off for in this?” Kendall hooks his pointed finger around a spaghetti strap of your dress, and lets the elastic snap back against your skin. You savor the sting it leaves behind.

Admittedly, there’s a third reason why you’re being so withholding. He’s so spoiled, so used to getting what he wants, whenever he wants it. Not just from you. And when he doesn’t get it, he becomes petulant, fiery. You’ve learned that if you piss him off just enough, you don’t have to ask him to fuck you within an inch of your life. He just does. 

So, you decide to poke the sleeping bear, shrugging and crossing your arms like it’s nothing, giving him a demure smile. “You wouldn’t know him.”

Kendall’s nostrils flare as his hand rises to grip your jaw – tightly. “Uh-huh.” Even if you’re only joking, the very idea of you dressing up at all – let alone like that –  for anyone except himself, pisses him off.  “Fuck you.”

“You’d like to, wouldn’t you?” you try to keep your voice even, but it sort of loses the steadiness you were hoping for when he hooks a finger behind your knee, dragging it up across the expensive, soft wool of his slacks to peg around his hip.

The bruising kiss that answers is clearly intended to erase the smug look on your face, and it works – your breath hitching, the hand on his tie tugging him closer. Kendall seems to speak without saying anything at all, grabbing your opposite thigh and lifting until you are perched on the edge of the countertop.

It’s getting real, but you still haven’t decided if you are actually going to stick around. The way he looks right now, however, swings the pendulum farther into the side of staying in – red lipstick left behind on his cheek, shirt wrinkled, tie hanging loosely around his neck. You wanted to make him look even more wrecked. 

Kissing him again, his hands begin to roam, tugging the dress off your shoulders and freeing your tits. “Shit,” He dips his head to sloppily mouthing at the newly exposed skin. “Knew you weren’t wearing a fuckin’ bra.”

“Ken,” you squirm when he latches onto one of your nipples, pinching the other between two fingers. “I really need to get going.”

“Not yet,” he hums, the vibration of his voice against your skin makes the space between your legs ache. “If you’re going to go out in this fucking dress,  I don’t want you to forget who you belong to.”

You squirm in his grip – not because you want to get away from him – but because you want to see if he’ll pin you in place, be even rougher. He does. He is. “Stop that. This isn’t a fucking negotiation.”

Well, okay.

He kneads into your thighs now, one of his hands dipping beneath the skirt of your dress that’s already so short he’s only an inch or so away from your already-soaked panties. 

“Fuck,” You tilt your head back to look at the ceiling, like you might find some self-control there, some will to resist him, but it’s about as cold and uninspiring as the rest of the apartment. “Please.”

Kendall lets out a dark chuckle,  pushing aside your thong and brushing his knuckles against your damp cunt. He loves to tease, and right now is no exception. His touch isn’t enough to satisfy, so you press yourself forward to seek it out yourself. You don’t dare meet his eyes, which you can feel are watching you intently, admiring how you keen and arch and whimper in frustration. Still, you aren’t quite ready to beg. 

Thankfully, you don’t have to. Without warning, he pushes two fingers inside you, groaning as he does, his thumb finding your clit.

“Yes, Kendall, that’s–” you don’t finish the thought because you aren’t entirely sure what you actually have to say. His digits curl, attentive, practiced – tuned in to  exactly what you like, what you need.  You grip at the fabric of his shirt that’s bunched around his elbows. Despite how intense meeting his gaze right now will be, you turn to look at him anyway, surprised by the affection and warmth you find in his eyes. 

“You try so hard not to be,” he says while he continues to stare you down. “But you’re always so fucking good for me.”

Your stomach flips, partly in shame, partly because of how good it’s always felt to be seen by him. Throbbing around him, feeling your pleasure build, but he withdraws his fingers from you before it can crest. An embarrassing noise leaves you, squeezing your eyes shut. 

The clink of his belt unbuckling immediately snaps you back to reality, and you hike your dress further up your hips, shimmying out of your thong. It’s pitiful, the way you don’t want to delay any longer the feeling of him inside you. 

He strokes himself in his hand, lines his cock up, and pushes a piece of hair off your face. 

“You want me?” he asks, and you bob your head enthusiastically. “Tell me, then.”

“I want you, Kendall. Please, I want you so bad.” 

“Yeah you do,” he mutters, and wastes no time jerking forward to enter you. 

Though you’d had him plenty of times you never could quite get used to the feeling – he’s big, of course, and it’s always electric, the blood in your veins buzzing, your hands tightening on his shoulders. 

“Relax, honey,” Kendall says, feeling the way your body tenses at the intrusion, placing a hand on your sacrum, one between your shoulder blades to steady you.

He presses his hips forward until they are flush against your own, bottoming out inside you, pausing. It’s welcome at first, a chance to catch your breath, to let out a shuddery exhale - temporarily appeased by the way your cunt stretches to accommodate him, and he’s so close to you after so much time spent away. You’re embarrassed at how badly you’ve needed this, how reliant on him you’ve become, but he always feels so good. 

Kendall stays still for long enough that you grow frustrated, and you use his tie to pull him closer, loosening the knot and rutting against him until he presses his thumb into the crease of your hip and thigh so hard you are forced to stop. Once you do, he starts to move, thrusts slow but deep, lips pressing hastily between panting breaths. 

“Fuck, it’s been too long,” he laments.

Despite everything, you can’t help but talk back. “You don’t say?”

Kendall doesn’t like that at all, his hips snapping at a punishing pace, which seems more like a reward than anything else, his hand clasping your jaw roughly, forcing you to look at him. 

“Don’t speak to me like that,’ he warns.

An involuntary, low moan leaves you. It’s overwhelming – always is. You aren’t used to sex with someone you feel so connected to, or with a lover who is so attentive to your needs, who effortlessly strikes a perfect balance between rough, passionate, and tender. 

You wrap your legs around his waist, fingers fumbling with the buttons on his shirt, anxious to run your hands through the smattering of hair on his chest, feel the warmth of his skin under your palms. Even if it’s not possible, you want to be closer to him. Needy. So needy. You’ve heard it from him before, and would probably hear it again. He is right, and in moments like this, you can never bring yourself to care. You like it.

He’s watching you so intently, and the rest of the city might as well be too. He basically lives in a fishbowl, you’re surrounded by windows that offer panoramic views of the glittering lights of the city. The only reason you have any privacy at all is because of just how high up you are, no one else can actually see you right now. Even if they did, what could possibly happen? Kendall loves to take advantage of this – he’s taken you up against the cold glass windows, has let you sink to your knees in front of him out on his balcony. 

“What are you gonna tell your friends when they ask why you were so late tonight?” he asks. “Gonna tell them you were letting me spread you open on the fucking counter?”

“God,” you stutter out, always shocked by the things that come out of his mouth when takes you like this, voice deep and firm, enunciating each syllable like he’s giving a speech – frustratingly collected. It makes you ache that much more. “I missed you,” you whimper, pulling his shirt off his shoulders. As much as you want it fully off, not just hanging loose around his elbows, you don’t want him to release you from the bruising hold he’s got you in. This would have to do. 

“Uh-huh,” Kendall answers by fucking into you even harder, his pelvic bone kissing your clit with every thrust, and your nails etching crescents into his biceps. “I know. I’m sorry.” 

His head falls to your shoulder in a brief moment of humility, lips working on your neck, and you feel your release fast approaching. In moments like these, you don’t doubt how he really feels. He gives it all away, tries his best to make it up to you, and it’s so easy to forgive him.  Kendall’s fist wraps around one of the stiletto heels of your shoes, lifting your leg to hook over his shoulder and drive his cock deeper into you. He’s perfect, feels perfect, there’s no one else who makes you feel the way he does. When his thumb begins to rub delicate circles around your clit, you’re gone.

Your body tenses up for so long, you actually think you might’ve psyched yourself out. And then everything releases. Kendall coaxes you through your orgasm, deep voice muttering things that are either unintelligible or that you wouldn’t dare to repeat out loud, and you cling to him while your cunt pulses in waves. It lasts for a long time, or at least it feels like it does, he slows just to fuck you through it, so you can both savor how good it feels. That’s it. That’s my good fucking girl. When he tries to kiss you, you oblige, but it’s open-mouthed and sloppy since you’re struggling to breathe and can’t stop whispering his name. 

“Ken, you’re so good, it’s so good–”

You know he likes to be praised just as much as you do. He cuts you off with a deep kiss, moaning into your mouth and vibrating every nerve in your body as he follows you over the edge, spurred on by your own release. He buries his cock inside you as deep as he can, you feel warm and full and complete. 

For what feels like a few minutes, you remain tangled with one another, his face buried in the crook of your neck. You can feel the soft puffs of his breathing against your skin, which is now damp.

Eventually, he draws back, kisses your cheek and tucks himself back into his underwear. You pull the straps of your dress back into place and when you push yourself off the counter, realize your legs are trembling and you wobble.

Kendall reaches to steady you. “Go sit down,” he squeezes your arm and you barely manage to stumble to his couch before you’re slumping against the cushions and struggling to unlace the strappy heels you’ve still got on. 

He joins you a moment later, placing a glass of cold water on the coffee table and kneeling to help you out of your shoes. You can only imagine what you must look like, because he looks disheveled, shirt still hanging open, pants unbuttoned, your lipstick still smudged on his cheek. Exhausted as you are, it makes you want him all over again. 

He settles next to you, pulls you to his chest, and you wrap your arms around his waist, leaning up to whisper softly in his ear. “Ken,” he turns his head slightly, cheek pressed against your forehead. “I love you.” 

From this angle you can only see the corner of his eyes, the way they crinkle as he looks down bashfully, eyelashes nearly touching his cheeks at your admission, words he so rarely has heard before. Words you have vowed to repeat until he believes you – because sometimes you think he doesn’t. Still, he answers. “I love you, too.” You close your eyes a moment, your heart rate returning to normal, and take in one final deep breath. Content. 

“I don’t want to keep you from your friends,” Kendall says eventually, hands in your hair, tugging gently so you’ll look up at him. 

“Right,” you nod. “Honestly, I don’t know if I even want to go out anymore.”

“But you got all dressed up,” he smirks.

“Look where it got me.”

He laughs. “Uh-huh. You knew what you were doing what you fucking put that shit on.”

You don’t deny it, feeling your cheeks grow warm. It’d be too easy to stay with him, to slide across his lap and kiss him until he takes you again. But your phone dings on the counter, and you know you can’t abandon your friends entirely. You sigh, pulling away from Kendall and looking him in the eyes. 

“Don’t worry,” he encourages. “I’ll wait up for you.”

[from-the-clouds]

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

gif by @televisionchronicles

Part One | Part Two | Part Three | Part Four | Part Five | Part Six | Part Seven | Fic Playlist | Masterlist

Summary: The final chapter.

Words: 5.1k

Warnings: Angst, alcohol consumption, brief mentions/discussions of sex.

A/N: When I tell you that I rewrote this chapter 3 different times, rewrote those rewrites, and then left literally thousands of words on the cutting room floor, I’m not dramatizing. I don’t know why I fought so much with this last part, perhaps because I have invested so much into this story and it's sort of sad to see it come to an end. Also because I couldn't seem to be satisfied with any ending that I wrote -- even this one I'm not fully in love with! But I’ve kept everyone waiting long enough. I really appreciate all the love I've received on this story, I've written for so many other fandoms and despite how small I feel like we are on here, the Succession fandom has by far been the most kind and supportive. I hope you all enjoy this, and who knows, this might not even be the last you see of these two. :)

Of all the places to be angry, this was not one of them. You knew that, looking out the windows at the end of the bar, at the palm trees swaying in the breeze and the waves creeping up along the white sand. An old Eagles song played lowly over the speakers, weaving underneath the chatter of the bar's patrons. The whole environment was manufactured happiness. But it didn’t matter. You were still angry. 

It had been a series of unfortunate events that led up to that moment. To you, slumped over a bar at one of the most expensive resorts in Hawaii, wrought with frustration. Continuing to mull it over, to wallow, wasn’t doing you any good – and you knew it.

As you finished off another round of well tequila on the rocks – a drink you were punishing yourself with – a new beverage was placed down in front of you, one you hadn’t even ordered. 

“Thanks,” you smiled weakly at the bartender. At least he understood to keep them coming. 

“Actually, I’m supposed to tell you that this one’s on the gentleman sitting over there,” he jerked his head towards the other end of the bar. 

Eyes nearly rolling back into your head, you refused to look right away. The last thing you wanted was to entertain conversation with some silver-tongued suitor who couldn’t read a room. Wasn’t it obvious to all the other patrons you were upset, that you wanted to be left alone? You’d assumed your sour mood would be deterrent enough on its own, let alone that after a nine hour flight and a tearful argument with the front desk staff you were looking rather haggard.

“Great,” you said sarcastically, but you weren’t in any position to say no to a free drink, taking a swig and welcoming the sting of the liquor. Funnily enough, it never came. Whatever had been ordered for you was an upgrade from whatever cheap brand you’d settled for when you sat down.

The nagging feeling of being watched didn’t let you hold out very long. You would have to give some type of acknowledgement or it wouldn’t go away. Preparing your best bitchy glare, you hoped whoever sent the drink would get the hint that you weren’t in the mood. Maybe it was ungrateful to snub the stranger who bought it for you, but you couldn’t be bothered to feign flirtatiousness at a time like this. 

But the glare didn’t make it very far at all, because when you saw the stranger across the bar, you realized he was no stranger at all. Hands clasped together as he leaned over the counter, aviators tucked into the collar of his linen button down, sat Kendall. His mouth was curved into a coy smile, eyes sparkling, and a person at the booth behind him was not-so-subtly trying to take his photo. You wondered if it was because they were simply shocked to see Kendall Roy fratnerizing at a hotel bar, or if it was because he looked so fucking good. Disgustingly good, seemingly better than the last time you’d seen him in person, salt-and-pepper stubble across his jawline, sunkissed along his cheekbones. 

Warmth flooded your cheeks at the sight of him, a reaction so automatic that you weren’t even able to save face by feigning annoyance. Not to mention the fact that you knew you looked like shit. Slowly, he rose from his spot and approached you. 

“Drowning your sorrows?” he asked, leaning against the bar, and while you badly wanted to play coy, you felt so ashamed of your current state all you could do was shrug bashfully, looking down at the rocks in the bottom of your glass.

“I guess you could say that.” 

“Want company?” 

You gave a small nod, and tilted your head towards the seat next to you. Kendall sat, taking a sip of what looked to be soda water and lime.

“How are you? It’s been awhile.” 

“It has.” He was right, two months had passed since last you’d spoken.

It hadn’t been for nothing, though. Because from the beginning of your fragile reconciliation, you’d been expecting Kendall to fuck you over. It would be a textbook. Grieving the loss of his dad would run its course. In the meantime, you were easy to cling to, something familiar, but disposable – he’d made that much clear time and time again. Eventually he’d find something– someone– better, and you would be left brokenhearted…again.

But after the night of his fathers funeral, Kendall didn’t reach out to you for emotional support like you were expecting. He did still reach out to you though. A handful of times, you’d met up with him for coffee or lunch. The absence of Logan’s malevolent presence in his life seemed a positive change, though that came as no surprise. He divulged to you he’d been seeing a therapist and he was working through the steps of a recovery program – actual healthy outlets for all his trauma.

Not to mention that Kendall’s whole demeanor had changed. It was like he was a different man – you couldn’t help but notice how he stood a little straighter, walked with a little more confidence, smiled more easily. Of course, he still had plenty of demons, and you still saw them slipping in and out of hazel eyes. Even then, it was probably the happiest you’d ever seen him.

Your instinct was still to keep your distance. All your meetups had been civil. Calculated. You didn’t talk about much else besides work, or what you’d been up to lately. And maybe sometimes, you’d reminisce about your days together at Waystar – conveniently avoiding any discussion of all the fighting and feelings. So it was very careful. Kendall was courteous, respectful of your personal space, of your boundaries and your time. After the time you’d spent apart, too, it was clear he moved on. With all the progress he’d made, you didn’t know why that last part was so disappointing. You’d moved on, too. It was for the better, after all.

“How’s Con?”

“Oh, just over the moon,” Kendall said. “His bachelor party is tomorrow. Roman’s planned it.”

“Oh god,” you raised your eyebrows, and snorted despite yourself. You couldn’t imagine what a bachelor party planned by Roman would entail. “Good luck with that.”

Kendall chuckled. “Yeah, I still have no idea what he’s getting us into.”

You’d been shocked to have snagged an invite to Connor and Willa’s wedding. Of the Roy siblings, Connor was the least familiar to you. In fact, of the couple, you were probably closer with Willa than anyone else – you’d spent many a Roy family gathering with her, shivering on a balcony, sharing a joint, and watching the circus from outside through floor to ceiling windows. 

“You’re here early,” Kendall observed. “The wedding’s not until the weekend.”

“Yeah,” you answered. “I was hoping to get out of town, take a break for a couple days, work’s been pretty crazy.”

“I seem to recall the last time we were together, you were bragging about how chill it was,” Kendall smirked. His whole body had turned to face you, knees slotted between your own as he rested his elbow on the countertop, fingers tracing the rim of his glass. You had to make a conscious effort not to stare at his hands. “Don’t tell me there’s trouble in paradise.”

“Ha-ha,” you said sarcastically. “It was. We’re just growing and understaffed. Good problems to have, I suppose.”

“Well, it can’t be as bad as the shitshow at Waystar, right?”

You felt a smile tug along the corners of your lips, feeling suddenly nostalgic. “No, it’s not that bad.”

Kendall grinned along with you. “Do you remember that time when I had to give that presentation, to…oh fuck, I can’t even remember the client’s name…..And in the middle of the presentation my dad called and made us put him on speakerphone so he could tell them to fuck off?”

“Oh god, yeah. That was fucking embarassing,” you said, straightening up, leaning in. “But he had some beef with the CEO, right?”

“Maybe,” Kendall’s face fell slightly. “That was probably just an excuse to fuck me over.”

The clear hurt in his expression nagged at your gut.  In the beginning, you’d been so naive when it came to Logan’s abuse. “I think I didn’t sleep for like 48 hours preparing for that pitch. And then it was all for nothing.”

“I didn’t know that.”

“Oh, I was so fucking pissed,” you raised your eyebrows. “Shit like that was always happening.”

“Uh-huh,” he turned away, and now he was looking at his feet. You took another drink. “Yeah….I still don’t know why you stuck around for so long.”

“Why do you think, Kendall?” scoffing, you looked over at him, knowingly. “I loved you.” 

The words slipped out before you could really process what they meant, the truth revealing itself so easily under the spell of alcohol. His head popped up quickly, his eyes were on yours, doing that thing they always did, searching, yearning, trying to find some sort of validation. But you weren’t going to give it to him. Couldn’t. You cleared your throat and spoke again. “Working with you, I mean. I loved working with you. It wasn’t all bad.”

It was a poor recovery, and Kendall nodded like he understood. In the awkward silence that followed, you scolded yourself for the slip-up. Good god, what the fuck is wrong with you? Get a fucking grip, how many things can you fuck up in one day?

“So, work, then? Is that what’s going on?” Kendall looked pointedly towards your half-finished drink and the empties alongside it.

For a moment, you’d forgotten why you were getting drunk at a hotel bar alone. And you couldn’t believe that it was Kendall who had a front row seat to the shitshow. Why did he always seem to show up at the most inconvenient times? And even worse, right now he seemed determined to get an honest answer. Coming into this trip, you had known you were probably going to bump into him, but you imagined that it’d be in much different circumstances. 

You hadn’t thought about it much, but maybe it’d be at the wedding, after a few days of decompression from work. You’d be wearing the expensive, new dress you’d bought for the occasion, the one that fit you just right. Okay, actually, you’d apparently been thinking about it alot, but no one needed to know that. You’d be put together, competent, he’d be able to see for himself. Look! I’m fine! Look! I have every beautiful thing anyone could want! Look! What you did hasn’t affected me at all! 

It was pointless, fabricated bullshit. And none of it would happen, anyways, because in reality he was here while you were unkempt, dejected, and halfway to blacked out before the bar had stopped serving their brunch menu. Oh, and apparently letting your tongue slip enough to confess old feelings you’d hardly ever acknowledged, not even to yourself. 

When Kendall said your name, you realized you’d never even answered his question.

“Uh, yeah,” you shrugged. It wasn’t a lie…well, it kind of was. If you were someone who considered omitting information a lie. 

“What is it?” you made the mistake of glancing at him, and his gaze was fixated on you again. Not so brooding, but wide, intent. And pretty….no. That was not helpful. 

“Nothing, it’s stupid.”

“What’s going on?” he asked, leaning a little closer, voice soft. 

“You’re going to laugh,” you said, shaking your head. 

“I’m not going to laugh.” 

There was no use in going back and forth all day. You gestured towards the bartender to bring you another round, finishing off the last in your glass before sighing in defeat.

“I uh….I forgot to book a room,” you said flatly. “I mean, I did, or at least, I thought I did. I wanted to come out early and have a few days to myself because work has been so crazy. But apparently it’s been so crazy that it must have slipped my mind. I get here, and the hotel is all booked up, as are all the fucking hotels around here. Now, I’m on one of the most remote islands in the world, and don’t have a place to stay. I’m probably going to have to sleep in the lobby tonight, that is, if they don’t kick me out. So I came here.”

To punctuate the ending of your story, the bartender set your next round down in front of you, and as you reached for it, Kendall caught your hand. “Hey,” he said. “Maybe you should slow down.”

The last thing you were expecting was to have Kendall of all people reprimanding you about substance use. You were in worse shape than you thought. Everything was going to shit. Somewhere, in the back of your mind, you entertained the possibility that you were being melodramatic. It was too late to turn back now, though. The anger you’d been feeling shifted to something else entirely, embarrassment surging to the forefront, so strongly that heat was rising up your neck. No, no, no, no, no, don’t cry. Don’t you dare fucking cry. 

Because you were now thinking just a little too hard, you were realizing. Maybe this wasn’t melodrama. Maybe this wasn’t about the hotel room, or your wedding date that had ghosted you last minute and showed up Instagram engaged the next day, or the crying baby that had kept you from sleeping a wink on your flight here. It could’ve been a little, but it wasn’t everything. There was more. You’d spent over a year now at a new job, creating a new life for yourself, determined to find happiness after everything you’d known was destroyed, through some fault of your own. You’d worked so hard to build it all, to convince yourself that it was the right path. But you had no other option at that moment than to face the truth. The truth being that after everything you’d worked for, you couldn’t help but feel like something was missing. 

“Don’t tell me what to do,” your voice cracked, despite the venom you’d attempted to lace through it. Kendall didn’t miss it, even though he loosened his grip and you reached towards the drink.

“Hey.” his voice was stern, a tone you hadn’t heard from him since your days at Waystar. He wasn’t your boss anymore, but muscle memory kicked in, and you paused, just long enough to look him in the eye. “Trust me, I don’t think this is the solution to your problem.” Voice soft, his thumb ran over the back of your hand. You shivered.

“I’ve, uh, I’ve got a whole villa to myself…and the kids aren’t flying in for a few days. Why don’t you stay in one of the guest bedrooms? The hotel might have some openings in a few days.”

You shook your head. “Ken, I can’t put you out like-”

“It’s fine. It’s nothing. How many fucking times have I put you out? I uh…probably owe you one.”

You snorted. He was right. “You probably do.” 

“Uh-huh,” he nodded. “Then don’t argue.”

“.....Okay,” you agreed hesitantly. This was definitely a bad idea, the worst case scenario you didn’t even consider when it came to options. But you had nothing else. You’d keep your head down, keep to yourself. It’d be fine. 

“Okay,” Kendall said. “Let me get the tab, we’ll get you out of here.” 

Considerably drunk, you stood, wavering slightly, and Kendall steadied you with an arm around your waist. You couldn’t help but lean into him, and you could’ve sworn on your walk to his suite he was etching soft circles into your hip with his fingers. 

The villa was huge. You didn’t know why all that space was necessary for one person. Four bedrooms, four bathrooms, multiple balconies, and a giant back patio with a private pool and spa that overlooked the ocean. 

“Feel free to make yourself at home,” Kendall said, hands tucked into his pockets as he leaned against the doorway to what was now your room, seemingly scared to cross the threshold while you put your luggage in the closet and snooped around. You turned to him, away from the floor to ceiling window with an ocean view. “I won’t be around much this afternoon, I told Shiv and Roman I’d meet them for lunch and it sounds like we have to help out Con with some last minute stuff.” 

You nodded. “Okay, sounds good.”

“And do me a favor…” 

“What?”

“Drink some water.” 

“Okay, dad.” 

Kendall’s laugh sounded a little pinched, but he stepped away, footsteps retreating down the hallway. Your shoulders sagged in relief once you were finally alone.

After a long nap that lasted a few hours, you woke up somewhere between still tipsy and hungover. Exhausted from the travel, the time change, and the tequila, you gulped down some water, and beelined for the shower, hoping that hot water and the two Advil you popped before getting in would quell the throb between your temples, and your turning stomach.

It was late afternoon now, and the sun would be setting soon. It felt somehow sinful that you hadn’t even stepped on the beach yet, and there was a good chance that a walk with your toes in the sand would clear your mind. After scoring a snack from the fully-stocked fridge, you donned a sundress and sunglasses, and set out.

The water was warm, crystal clear, and you waded ankle deep as you made your way down the secluded shoreline, focusing on nothing but the sound of the waves, the heat of the sun on your exposed skin. It didn’t take long for the problems that earlier had you slumped over a bar to shift into perspective, the tension and stress slinking off your body with each turn of the tide. It wasn’t until the sun began to dip below the horizon you decided to head back.

“Hey.”

You were slinking past the pool on your way to the bedroom when his voice started you. Kendall sat on an oversized lounger that had an impossibly picaresque view of the ocean, and the sunset, thumbing the pages of a book on his lap.

“Hey, sorry, I didn’t see you,” you said, sheepishly. 

“That’s okay,” he answered. “Are you uh…are you feeling better?”

“Yeah,” you offered a stiff smile, laughing it off. “I’m sorry about all that. Guess that’s what nine hours on Spirit Airlines can do to your psyche.”

“Spirit Airlines?” Kendall cocked his head. “Can’t say I’ve heard of it.”

“Of course not,” you couldn’t help but giggle at his joke.

“It’s uh, it’s okay, though. To be honest, it was kind of refreshing to not be the one breaking down for once,” he grinned.

“Well, in that case I’m glad I could be of service.”

Kendall laughed, fully this time. “Want to sit?” 

“Only if you promise to change the subject,” you weren’t interested in dwelling on what had happened earlier. 

“Deal.”

Normally you’d say no, but after your walk, you were convinced that it was a little irrational to be so afraid of him, of spending time with him. Things didn’t feel nearly as natural as they once had, but had they ever been that natural to begin with? You still derived a strange amount of comfort from his presence, even if the anxious part in your brain found that displeasing.

Kendall’s shirt lay open, unbuttoned, most of his torso bare, and a few water droplets clung to his exposed skin, probably from a recent dip in the pool. He looked a fair bit more muscular than you remembered him to be, not that you’d had any issue with how he had looked before. In fact, the issue now was that he seemed to be looking better and better every time you were together. You weren’t sure how long you spent checking him out, but you were thankful for your sunglasses when you finally snapped out of it. 

If he noticed, he didn’t say anything, seemingly content, one of his arms slung over the back of the couch. You wished you could feel that, too. With the exception of the odd fling here and there, it’d been awhile since anyone offered you any affection. After the stress of the day, you wondered what it might feel like to rest your head on his lap, to have his fingers running through your hair absentmindedly. Even during your brief time together, you hadn’t really been allowed that sort of domesticity. 

“What are you reading?” you asked. He closed the book and shifted over so you could sit next to him, and he showed you the cover.

“Something my NA sponsor recommended. So far, it’s not great.”

“That’s the worst,” you sympathized. “How’s that going, anyways?”

“What, sobriety?”

You nodded. 

“Honestly, it uh….it fucking sucks,” Kendall said, then shook his head, offering a short exhale a weak laugh. “I’m kidding…uh, you know…it’s not so bad. Better than where I was before.” 

You nodded, leaning against the back of the couch and tucking your legs underneath you. “So when you were at the bar today, it was only to pick up women?” you teased. 

Kendall tilted his head, warmth glowing in his eyes. “Just one.”

Your stomach flipped, and you tried to play it off. “Uh-huh.”

Thankfully, Kendall moved on. “So, are you here alone, then?” he asked. “For the wedding?”

“Yeah,” you said. Your on-again, off-again fuck buddy and go-to wedding date, Ron, had bailed on you last minute. Then, right before boarding your flight, your friend had sent you a photo of him cuddled up with a perfect, blonde model, who was proudly displaying a diamond ring to the camera. It was part-hilarious, part humiliating, since the last time you were over at his apartment, he’d made a big show of gifting you a bottle of your favorite Rye ‘to keep on hand’ for whenever you came over. There had always been an expiration date, you weren’t disappointed it was over, but realizing you were the other woman was unsettling, you felt dirty somehow. “Why?” 

Kendall shrugged. “Well, you know….you were at uh, my dad’s funeral with Stewy.” 

You frowned. “....And?” 

“I don’t know, you just….you seemed….close.” He paused. “I thought maybe….”

It clicked for you. “Oh my god. You’re joking.”

“Uh-huh, look, I uh, I just got a vibe.” 

“Oh, you ‘got a vibe’? What kind of ‘vibe’?” 

“Forget it. I’m just saying,” Kendall raised his hands. “I’ve known him for awhile, we used to party together in college, and he’s not exactly the most loyal-”

“Oh my god, stop, I already booked the wedding venue, what am I gonna do?” It was laughable. Stewy had texted you after the funeral to apologize for dipping out, and that was the last time you’d heard from him. 

“Fuck off,” Kendall’s voice sounded pinched, even though his shoulders had relaxed slightly. “I just had to say it.” 

“I appreciate the warning.” Was he….jealous? There was no way. Gerri had already told you a little while back that Kendall had been linked to some former anchor at ATN, and things seemed pretty serious. You had been a little puzzled as to why she thought you should know, and found yourself wishing she would’ve kept it to herself. But this was probably just his guilt talking, some cheap attempt to prove that he actually cared about your well-being, you rationalized. 

You had to bite your tongue to keep from pointing out that between himself and Stewy, only one of them had ever broken your heart, and it wasn’t Stewy. But you figured it best to stay quiet. “What about you?” you asked. “I assume you’re here alone?”

Kendall nodded.

“Finding a wedding date,” you mused. “It's way harder than you’d think. I mean, the date part is easy, but actually having a good time with the date is always what gets me.”

“Uh-huh, is that right?”

“Yeah,” you continued. “You’re not only a guest at a party, you’re also playing host for someone. You gotta make sure the date is having a good time with all these people they don’t know. It’s so much effort.” 

“You know,” Kendall cocked his head. “You’re making a really good case for us to just go together.” 

“Very funny.”

“What? I’m serious,” he said. “It might not be such a bad idea. And uh…lately, I think that you and I, we’ve been really good. Fucking nice and professional. Haven’t we? ” 

“Mmm, I guess.” 

“I think we’d have fun.”

“Mmmmmmmm,” you wrinkled your nose. “Would we?”

“Come on,” he said your name. “At the very least, we know there’s chemistry.” 

“Oh, is there?”

Kendall leaned forward, slightly, and the lounger seemed a lot smaller than it originally had, his face was only inches from yours. “Do you need a reminder? We used to-”

“Yeah, I know,” you cut him off. 

“I think about it all the time. Don’t you?” One of his hands settled on your knee. Your skin burned where he touched you.  

You bit your lower lip, squirming in your seat, thinking about a few days prior when you’d spent the evening writhing in bed, imagining his head between your thighs. Or the week before, when you’d zoned out during a business meeting, because the only thing ping-ponging around in your brain had been the sound of his voice, low and sultry. Good girl, you look so pretty with your mouth full. 

If for nothing else other than spite, you were determined to keep your wits about you. “Maybe, sometimes….” Even if it was difficult to maintain your composure, you closed the space between you even further, your hand on the armrest by his side, across his body. Kendall smelt of sun, of saltwater and cigars, and the cologne he wore that you’d never been able to place, maybe because he wore something different for every occasion, always equally intoxicating. And you were reminded how easy it was to flirt with him, to render him speechless with his breath caught in his throat. His eyes were half closed in anticipation, until you spoke again. “And then I remember that you’re bad news.” 

Being cruel hadn’t been your intention. You had only wanted to beat him at his own game. But when you pulled away, the ornery sparkle had left his eyes, and they were vacant. Actually, you might as well have slapped him. He tried to save face, swallowing hard, the fake smile he forced looked more like a grimace, and he shifted away from you and brought his legs closer to his chest, resting his elbows on his knees. “You’re probably right, I was uh…just kidding.”

You pulled away too, a little ashamed of yourself. But you decided to pretend you didn’t notice his reaction, for his sake and your own. So you changed the subject. “How was your lunch?”

“It was….good,” Kendall answered, but avoided your gaze. “Shiv and Roman are good. Connor is so happy….which is good, too, I guess.

“I would hope so.”

He didn’t answer, just turned to look at the ocean, and you followed his gaze, the last evidence of the sunset just a fading orange glow on the horizon. After a moment of silence, he laughed to himself, bitterly. “Yeah, fuck, I’m uh….I’m trying to think about the last time I was that excited about someone.”

“Oh yeah? Rava?”

“No.”

You knew what he was saying without him even having to say it, when he pivoted back towards you. The attraction you felt towards him – had always felt towards him, was impossible to deny, especially now, with his features basked in waning sunlight. He really was so handsome, you didn’t want to admit how good it felt to have all of his attention, to know what he was saying without having him say it. 

You gave him a weak grin. “I know the feeling.” However short-lived it had been, you just couldn’t bring yourself to lie.

“You’re right, you know?” he answered. “I’m bad. I really fucked it up. I’m sorry.” 

“Kendall, don’t-You’ve already apologized. It’s in the past now.”

At that sentence, he looked back at you, sitting up straight, though the forlorn gaze you were used to seeing had returned to his eyes. It was the most tortured you’d seen him since Logan died. “I loved you, too, you know that? I still-” he began, but paused, shook his head. “I hope you know I’d do anything for you, whether you want me or not.” 

“It’s okay, Ken.” You frowned, wrapping your arms around yourself in a tight hug. “You don’t have to worry about me, anymore.”

“I want to,” he said your name, and reached up to push a loose piece of hair off your face, thumb lingering on your cheek.

He was so close, getting closer, and you were so aware of the proximity between you both. Warmth bloomed in the pit of your stomach, rose like smoke up your neck and settled in your cheeks. And worse, it was prickling at the corners of your eyes.

Almost as if to demonstrate, Kendall’s palm left your face, and he took your hands gingerly, moving them away from your chest so he could pull you closer to him, an arm around your waist. You couldn’t resist the embrace, letting him tuck your head beneath his chin, body pressed against the sun-kissed skin of his torso.

You stayed like that a moment, listening to the steady thump of his heart, his fingertips grazing up and down your arms, skin tingling in their wake. It wasn’t enough. Pulling away slightly, you spoke. “You’ve always had me,” you said softly.

His mouth curved slightly, and he leaned in, his mouth finally connected with your own. Years worth of pining, of fighting, of misunderstanding and miscommunication all seemed to dissipate in that single press of his lips. It was soft, gentle, and he pulled away slightly at one point, to let his forehead rest against your own, his thumb swiping along your bottom lip, his free hand drawing your body somehow closer.

You’d remember the night for the rest of your life, even just if it was in snippets, his mouth on the inside of your thighs, how full, complete you felt when he finally gave himself over to you, the sweet nothings he whispered when you came undone beneath him. And you’d always remember afterward, as you laid in his arms, mapping out constellations in the sky stretched above you, how it felt like everything had finally clicked into place.

[from-the-clouds]

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

[from-the-clouds]

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

Part One | Masterlist | Fic Playlist | Gif credit

Summary: You check on Kendall after he returns from Italy. Takes place after Succession 3x09 ‘All The Bells Say’

Words: 7k

Warnings: Contains SMUT (minors dni) unprotected sex. Alcohol/drug use and abuse. Depression. Mentions of attempted suicide. Kendall Roy existing and being a deeply sad man. Spoilers for seasons 1-3 of Succession.

A/N: Happy new year!!! This might be the horniest thing I’ve ever written so either 1) i’m sorry or 2) you’re welcome, I’ll let you decide. Please let me know what you think! Also, if you’ve sent me a request, I am working on those, please don’t think I’m ignoring you! I try to do them in the order they come in.

"Come inside, Mr. Roy should be home any minute."

You nodded, as Sasha, one of Kendall's staff, stepped aside, allowing you to follow her into the penthouse apartment. Kendall had moved here somewhat recently, after he separated from Rava, and you'd only been a handful of times.

Sasha led you into the great room of the luxurious home. "Can I get you anything?" You shook your head. The real reprieve was the air conditioning – you'd worked up quite the sweat getting over here, even in your lightweight summer dress.

"No thank you."

She disappeared down a hallway, and you were left alone. Every time you'd been here before had been for work, but brief, to drop off documents or strategize quickly before meetings. Though you were frequently surrounded by wealth and extravagance, right now, standing alone in Hudson Yards penthouse nearly knocked the wind out of your system.

You already felt on edge considering the circumstances, and this setting wasn't helping.

The stark white decor, with the occasional black accent, made it feel more like a museum and less like a home. It was almost laughable how over-the-top it was, floor to ceiling windows, multiple lounge areas. It had something like six bedrooms – you didn't know for sure, because you'd never seen them, but that seemed particularly egregious considering that Kendall's kids were rarely over and he didn't keep any company besides his various flings. So much of the excessive square footage likely went to waste. But this was how the super wealthy lived, you'd learned.

About a year ago, you'd finally been able to move out of the tiny, shitty apartment you'd shared with a roommate, and now you lived alone in a one bedroom place. That felt like a luxury to you, but you were realizing it looked like a shack compared to this, and it wasn't cheap by any means.

All the exterior walls were made up of windows, and you walked straight towards them to peer out over the city, letting your forehead fall against the glass to look down. From this height, 90 floors up, you were too far up to even make out the shapes of people walking below. There was, however, something mesmerizing about towering over the city like this – a city that often made you insignificant and replaceable. Right now, you felt neither of those things.

Standing there, watching life pass by, you lost track of time, until you heard the clack of dress shoes against the wooden floors, and a familiar, deep voice approaching.

Perking up, you stepped away from the window, smoothing the hem of your dress out of habit. Kendall rounded the corner and didn't register you right away, but you noticed every detail of his appearance. Phone to his ear, suit jacket slung over his free arm, his aviators were still perched on the bridge of his nose. Looking much more rugged than usual, stubble covered his jawline, and at some point between now and the last time you'd seen him, he'd shaved his head. Behind him, the woman who'd let you inside snuck his suitcases around the corner and likely into the master suite.

"Uh-huh, yeah," Kendall murmured into his phone, all business, but when he saw you, he hesitated. "Hey listen, I gotta go - let's talk tomorrow."

Kendall removed his sunglasses and squinted at you, pocketing his phone as he halted on the opposite side of the room.

"Uhh…what's going on?" he asked. He had a bit of a tan from the trip, but he still looked haggard, dark circles under his eyes, which were glazed over. The sleeves of his dress shirt had been rolled up to his elbows, likely in response to the heat in the city today.

"Hey," you answered, shifting your weight between two feet as he approached you hesitantly.

"What are you doing here?" he asked, and his tone was hard to read.

"Sasha let me in," you answered. "Uhm, sorry I didn't give you a heads up before," Kendall eyed you skeptically. "I heard you were back in town and I thought I'd stop by and uh…check in."

It had been Greg that texted you, letting you know that he was back in the city. It was a Friday night, you had one foot out the door on your way to a date, but had dropped everything to come here. You figured if Greg was back in town, then so was Kendall. You were right.

"Uh-huh," Kendall answered. "That's all? Not 'cause you're worried you're going to lose your job?"

Your stomach flipped. The last time you'd been alone with Kendall was the night of his birthday. He'd snuck out quickly in the morning. Since then, you'd only seen each at work, with other people around, and you'd both kept it professional. You weren't really sure where you stood with him, and after everything that you'd heard had happened in Italy, you couldn't handle the radio silence.

"No," you swallowed. "I heard about Italy, I just…I wanted to see how you were." Sure, maybe your job was a lingering concern in the back of your mind, but it would've never occurred to you to show up to Kendall's place and talk to him about something so trivial when you knew everything.

"What do you know?" he asked, tone stern and cold, and you knew to some extent he was only protecting himself.

"I know about Gojo and….the uh, the swimming pool…thing," you managed.

"Uh-huh. Who told you about that?"

"I uh…Greg."

Kendall laughed bitterly. "You shouldn't talk to him anymore, he's not a friend of ours."

All of the sudden it felt like there was a draft passing through the room. The A/C was far too cold, and Kendall's steely demeanor wasn't helping. Maybe this was a mistake. Maybe you misread things, maybe the night you spent with him didn't mean as much as you thought it had. You felt like an idiot for thinking otherwise.

"I know," you answered. "I know that, I just…." you swallowed hard, your face growing hot under his frigid stare. "I was just hoping to see you, Kendall. "

Kendall put his hand on his hip for a minute, studying you carefully as if he didn't believe you. There couldn't possibly be a reason you were there without some sort of ulterior motive. After a moment his face dropped, the emotionless, 'fuck you' facade he presented to the world slipped away, leaving behind the forlorn expression he'd gotten so good at hiding.

"Come here," he murmured, and you let him pull you into his arms. It was a catalyst, the tears that you'd been trying to smother since you'd heard the news of his accident came rushing forward, sliding down your cheeks. When you sniffed, his hand rose to cradle the back of your head, letting you nuzzle into his shoulder, holding you tightly. It was nice to have someone need him this way, for once.

"I'm sorry," you managed, hearing your voice break but continuing anyway. "I was so worried about you, I just needed to see you're okay."

"I'm okay," he soothed. "I'm okay."

"That's what you said before you left," you whimpered. You didn't want to talk too explicitly about what happened in Italy. You hadn't gone, Kendall had even given you the few days off. "What happened?"

"I promise you, I'm doing better," he dismissed your question. When he pulled away, he still clung to your shoulders, leaning down to look in your eyes. "Trust me, okay?"

You nodded wearily, his thumb grazed your cheek to wipe away a stray tear, eyes lingering, locked on yours, face mere inches away for too long to be appropriate. Not that it mattered to you. He had a way of making you feel like a fucking teenager again, all lightheaded and dizzy at the mere thought of kissing him. And then he pulled away, removing his hands from you.

"For the record," you swiped quickly under your eyes, clearing your throat. "I am still worried I'm gonna lose my job." You couldn't handle the tension in the room, you hoped your weak attempt at a joke would clear it up.

Kendall chuckled, and you didn't miss his quick once over as he stepped backwards. "You're all dressed up, you headed somewhere?"

You shrugged. "Not exactly."

"Have you eaten?"

"No."

"Uh-huh, well…I feel fucking gross, I need a shower, why don't you hang tight for like 20 minutes?" he asked. "We can grab a bite somewhere, talk some more."

"Uh, yeah," you said. "That's fine."

"Great." He retrieved his jacket from the couch. "Make yourself at home," he stepped away, disappearing down a hallway.

While he was gone you wandered to the dining room, finding a bar area with a sink and a mirror you used to touch up your makeup. You'd never been a believer in waterproof mascara, but you might have to convert based on the way these past few weeks had been going.

Kendall returned in a slightly more casual look, khaki-colored slacks and a blue button-down, the sleeves rolled up, typing on his phone. "You ready?" he asked. "The driver's downstairs."

He snuck you both out of a back entrance, avoiding the reporters that were now cluttered at the front of the building since news of his arrival back in New York had spread. At this point, the Waystar acquisition was no secret, even if the deal wasn't finalized.

The restaurant he'd chosen was nice, much nicer than you'd expected, much nicer than a place you'd describe as somewhere you could 'grab a bite to eat' as he had. Kendall's hand grazed against your lower back as the hostess led you to a secluded table.

"Can I start you off with some drinks?"

"I'll have a club soda, she'll have a Manhattan," Kendall answered quickly, ordering you your favorite cocktail.

The hostess left before you could say a word, and you frowned at Kendall. You were relieved, at least, to hear he wasn't drinking.

"Don't look at me like that," he glanced at you from over the menu. "I didn't want you to do that thing people do."

"What thing?" you asked, settling across from him.

"You know, when they find out I'm not drinking and then they don't drink because they feel weird about it and then it makes me feel like a fucking wet towel," he said. "It's Friday night, have a drink."

"Well, I know you're not a wet towel, that's for sure." you teased, and he rolled his eyes.

"You didn't have plans tonight?" He changed the subject.

"Uhhhh, well, kinda," you shrugged.

Kendall raised his eyebrows at you from over the menu.

"I don't know. It was like a date….maybe, I think."

"A date?" Kendall asked. "With that guy you're seeing?"

"You mean Ron?" You smirked, crossing your legs under the table and putting down the menu you'd been browsing. "You're so into him, aren't you? This is like….the third time you've brought him up."

Kendall frowned. "I just find it interesting…the way you talk about it. So fucking…like, cagey."

"How's Naomi?" you shot back.

Kendall grunted. "We're uh….you know. Whatever."

"See? I don't like talking about my personal life either."

"It's different," Kendall said. "You're such an enigma."

Raising an eyebrow, you resisted the urge to quip back something unfriendly. Even though you knew pretty much everything there was to know about him, all the ins and outs of his personal and professional lives, Kendall had never really made much of an effort to get to know you in return, beyond general pleasantries. Not that you cared, as the arms length approach seemed to work better, at least at first. Things were slowly changing, but it was still a one-sided relationship.

"Things aren't great," Kendall said after a pause, leaning forward. "With Naomi. Feels like things are…fizzling out."

Before you could respond, the waiter came by with your drinks, and to take your order. By the time you were gone, you felt like the moment had passed to ask him to elaborate.

"So are you going to tell me about this Gojo stuff or…?" you asked.

Kendall sighed. "Well, short and sweet, they're gonna buy us out. Mattson will be the new CEO, and then he gets to decide how to cut the fat. I don't know that he'll see Shiv, Roman or I as essential to the company, so we'll probably get fired."

Kendall didn't really seem as emotional as you were expecting him to be. For the past few years his goal of becoming Waystar's CEO had driven nearly every decision he'd made, and seeing it all crumble, seeing it all be for nothing, had to be eating him up. "And you're okay with this?"

"Shiv and Roman are pissed, and I am too, but…." Kendall shook his head. "I feel more relieved than anything else."

"What do you mean?"

"I took your advice. I tried to get out," he said. "My dad….he wouldn't let me. But if this deal goes through, if he's no longer in power, I'll be able to. It won't be everything I want but, maybe it's time. I mean, hell, it'd probably be a relief to Mattson, since I'm useless anyways."

"That's not true."

"You don't have to lie to me," he said. "I am. And it's okay. Whether I'm CEO or not, none of it changes. I'm still fucked. Forever."

Despite the fact that he seemed somewhat measured about the whole situation, your concern was in his words. "You don't have to be," you reached out, fingers grazing over his hand. "You can get help."

"Uh-huh," he smiled bitterly, looking down. "Because that's worked out so fucking well for me in the past."

You swallowed hard. "Listen," Kendall said, flipping his palm over to clutch your hands. "I'm really okay. You have to believe me."

The room you were dining in was dim and private. There was no one else around. It might be risky to poke the bear, but at least it was safe.

"And did you feel this way before or after you ended up in the pool?" you asked him, and maybe it sounded harsh but you couldn't ignore the elephant in the room. "I mean Kendall, really, you can't say all these things to me like that never happened. I mean, did you even talk to anybody?"

"That was an accident," he growled, and despite the ice clipping the edge of his voice, you knew he knew you weren't convinced. But you didn't have to say anything before he continued. "This was all after," he quipped. "I talked to Shiv, Roman, and Conner. At least I have my siblings back."

That was somewhat of a relief, but you'd never really trusted his siblings, as they were quick to betray him to get into Logan's good graces. Who knew how long this truce would last. "Kendall, you need to talk to a professional."

"Uh-huh, look, I didn't bring you here to get fucking lectured, okay?" he said curtly. When you tried to pull your hand away in response, he clasped it tighter, holding you there. "I'm sorry," he breathed, softening. "I just can't get into all this now. It's too much."

He was right, though, you weren't being fair. Now was not the time. "I know, I just hate seeing you so…" you trailed off and took a sip of your cocktail.

Broken. It's what you wanted to say. But you couldn't, the word lay dead on your tongue. That profound sadness that always consumed him. You could feel it in the pulse point on his wrist, connected with your own. You wondered if something stronger could ever subdue it.

"Uh-huh," Kendall answered, and he released your hand gently from his iron grip. You always found it interesting how he responded when you admitted you were wrong, like he'd never encountered emotional control before. He probably hadn't.

"So…I probably will get fired then," you said, changing the subject. "When all is said and done."

He shrugged. "Not necessarily. You're smart. Mattson will probably find a place for you."

"I don't know," you said. "It might be time for a change."

The waiter arrived with your food, and you ordered another drink, watching him take a few bites of his meal. It occurred to you that if Waystar was really being sold, not only would you be out of a job, but you would also be of no use to Kendall.

"It'll be weird…" you said. "I'm so used to being at Waystar, working for you."

"Sounds like that would be a relief" he looked up at you, lips quivering into a rare smile. He looked so handsome when he smiled, the way the corners of his eyes wrinkled, the way his gaze shifted downwards, almost bashfully. You finished off the last of your drink. "But we'd still be friends."

"Mmmm," you tilted your head and pursed your lips. "But are we even friends now? Being friends would involve us talking about something other than work 24/7."

"Touche," he answered.

After dinner, you ended up back at his place. You weren't really sure why. You should have left to go home from the resturaunt, right to your apartment. It didn't make sense, but both of you seemed to have the same, unspoken agreement - that you weren't ready to end the evening yet. For you, it was the paranoia something bad might happen if you let him out of his sight. You weren't sure what his reasoning was, but you didn't really care.

"Thanks for dinner," you said, as Kendall followed you out of the elevator. "I can Venmo you, if you want," you elbowed him playfully.

"Yeah, go ahead, I'm gonna need the fifty bucks soon, help me pay the rent here," his hands were in his pockets.

"Speaking of," you gestured towards the great room of the penthouse. "This is place is fucking insane, I mean, really."

"Uh-huh, thanks," he said, following you to the wall of windows in front of you. It was dark now, and the city was lit up, squares of yellow lights covering the buildings, portals into another world.

"Do you ever stand here and just enjoy this view?" you asked.

"Not really," Kendall chuckled, standing beside you. His presence was both comforting and unnerving.

"I'd never get anything done," you glanced over at him, and he was looking at you, not at the view. When you caught his stare, though, he indulged you, and turned back towards the window.

"I guess it's pretty sick."

You shifted your weight in the boots you'd worn. They had been comfortable at first - practical, as you knew sandals just weren't a possibility in the city. Stepping away from the window, you sat on the couch to pull them off. "Okay, these are hurting me."

Kendall turned on the fireplace in front of the couch you'd sat on before joining you. Light danced over his face, you leaned back against the back of the couch and closed your eyes.

"It was nice," Kendall's voice echoed, and your eyes fluttered open as you turned to find him looking at you. "...to see you when I came home."

"I needed to see you," you answered. His pointer finger slid lazily over your hand resting between you, gauging your reaction. Your eyes didn't leave his.

His lips were full, perfect, pink. You wanted to know what they'd feel like on your own, on your neck, on your- no. You stopped yourself.

"You know I'll always take care of you, right?" Kendall asked. His pointer finger locked with yours, linking them together like this was some sort of promise. "If you need money, you need a place to stay, whatever."

You shook your head no. "I'm going to be fine, I don't expect that from you."

"That's why I want to. No one else I know is like you."

His sweet nature was oozing through his carefully curated facade, a bit of the sadness along with it but the sudden tenderness was overpowering. The side of him you'd believed many times that his father had beaten out of him. For the world? I'm sorry. You're not made for it. Any ounce of compassion Kendall had was always seen as a weakness, but those small glimpses of who he really was were what had kept you around.

"Thank you," you answered.

"You said we aren't friends," he said. "Maybe that's true. But…I want to know you."

"Okay," you whispered, shifting your weight so you were on your side, facing him directly.

His free hand rested between you, the one that wasn't clasped with yours, lifted to ghost over your knee. Kendall was testing you, seeing what you'd allow, seeing what touch went too far. He'd been in your arms, you'd been in his, but this was one boundary you'd never really crossed. He wanted to know. Watching your every move, each hitch in your breath, each microexpression, where were you going to draw the line?

Kendall felt he had been patient for too many years. Now you were here, laying across from him, the skirt of your dress riding up your thighs, letting him see more of you than you ever had. Had you been expecting to see him tonight when you put on that outfit? Or had this been for another man?

More broken now than he'd ever been, it felt like you were the only thing holding him together. How much of himself could he give away, in the hopes that you could fix it? He knew it wasn't right, technically, to look for answers in your arms, but he'd run out of ways to cope. Would it feel any better just to have you?

"I know you want to kiss me," you said, voice low. It was just like you to know. The only person who saw him, all of him, even the ugliest parts, and still chose to be loyal. There were only a handful of things he could give to you as a reward for your honesty, and the things he'd already tried didn't seem like enough. You deserved more.

Kendall moved, shifting his weight so he was above you, looking down, moving closer. "Do I?"

"I can feel it," you looked up at him, squeezed his hand. He moved a piece of hair from your face, trailing his touch along your jaw before angling your chin upwards. There was no resistance on your end, you were so open, so pliant beneath him.

Kendall slotted his lips against yours. He had approached you so painstakingly slow that you knew it hadn't been a mistake, or merely a decision made in the heat of the moment. It was purposeful.

He was gentle at first, chaste almost. Goosebumps pricked up your arms, your heart rate increasing. A million sweet nothings filtered through your mind of things you could say to him, but you couldn't find one that felt right, so you channeled all your energy into the kiss, which he deepened, tongue sliding to part your lips as he pulled your face closer.

You answered in kind, gripping his shoulder and jaw, the once-innocent gesture becoming more and more passionate. An involuntary whimper left you, and Kendall smiled against your mouth.

His opposite hand trailed down your body, grazing over your breast, waist, over your hip, pausing just above your knee, where your skin was bared to him, and he pushed apart your legs, which had been crossed. It was instant, the shock of arousal to your center, the sharp intake of breath in response, as if his lips on yours hadn't already awakened the deep-seated desire. You'd barely just begun to kiss him, and yet, you already knew what you needed.

Kendall eyed you when you pulled away, slightly, admiring you as your chest rose and fell, lips swollen and hair mussed. "Do you want this?" he asked.

"I do," you breathed. "I want it so bad, Kendall."

His lips connected with yours again, his cool hand slipping farther under the skirt of your dress, up the inside of your thigh, stopping just short of your panties. You moaned, then, into his mouth, so desperate, so needy. As much as you wanted to only keep kissing him, you couldn't resist exploring more.

"I want you in my room," he said. "Properly."

You only made it a few steps down the hallway before Kendall spun you around and nearly slammed you against the wall, lifting your knee to hook around his waist, cupping your ass with his free hand and grinding his hips against yours. He was already hard. You expected him to take you there against the wall, would be satisfied with that, as your fingers fumbled with the buttons of his dress shirt, managing to unbutton two, but he pulled away, the loss of contact making you huff in frustration.

"Come on," he said, a devilish look in his eyes.

You could hardly walk straight, the ache between your thighs was so intense it was painful, desperate for relief. It was annoying, how big his apartment was, the walk to the master bedroom took years, and it didn't help that he seemed unfazed by it all. You thought of all the other women who had walked down this hallway with him and then pushed the image out of your mind.

His bedroom was huge, low-lit, the lights of the city glimmering outside. It would've been nice to take a moment to appreciate the view, but there were other pressing matters at hand.

Kendall backed you into the bed, stepping between your legs and sliding a hand up your back to catch the hair at the nape of your neck. He kissed you again, your hands cradling his face as the desperation in his actions became more and more apparent, and you were becoming less and less patient.

His large hands returned to your thighs, massaging them as you let your legs fall open, his thumbs kneading into the soft flesh, working up close to your panties again. One of his knuckles grazed over the skin there, and you sighed, pressing your hips forward to seek more contact. Instead, his fingers hooked over the waistband and pulled them down around your ankles swiftly. You kicked them off eagerly and Kendall was quick to push your dress up over your hips.

Feeling suddenly exposed, you sat up, legs instinctively moving together, and Kendall paused, leaning forward to press his lips to your temple. "Is this okay?" he asked, voice a low whisper into your ear. "Want to make you feel good."

His words erased any self-consciousness you felt, as you knew he was exactly what you needed right now. "Mhm," you answered, raising a leg and pressing your heel into his back so his body was closer to yours.

Kendall chuckled, a sweet and warm noise that made your stomach flutter. Your lips met briefly again, a sloppy mess of teeth and tongues, before he backed away from you to kneel between your parted legs.

He waited far too long to touch you again, leaving you wanton and panting, watching him, waiting for his next move, until his hands wove around your thighs and pulled you to the edge of the bed, holding you in place. You were throbbing, aching, you could feel yourself growing wetter as he buried his face between your legs and kissed you everywhere except the place you needed him most, nipping and sucking at the skin newly exposed to him.

"Kendall, please," you begged for it, the plea slipping out before you could stop it, the urge for contact overriding all logic.

"God, I knew you'd be just like this," he groaned into your thigh, the vibration of his deep voice radiating straight towards your core. "So fucking wet for me, so ready."

There was no time for a response before Kendall gave in, warm tongue sliding to part you. He was right. You were so wet, it was sinful, and your head fell back at much-needed contact, the relief to finally have him where you wanted. He was eager, lapping greedily at your cunt, and you gripped at his shoulders to find purchase. The heat consuming your body was overwhelming, and only intensified when his mouth latched onto your clit, drawing a long moan from you.

"Sweet girl," he chuckled. "I could come from just the taste of you."

Heat flashed through your abdomen. You had no idea how to respond to his absolute filth, besides whimpering and grinding your hips harder against his face, which he seemed to like, his hands squeezing and grasping at you over your dress.

"I want you…to…" you managed. "Inside me."

"Be patient," he cooed. "Want you to come on my face first."

God, fuck, he was depraved. And you couldn't answer because you wanted to, too.

"That dress you wore," he mumbled, tongue circling your clit. "On my birthday." His hand traveled up your inner thigh. "I thought about fucking you in it all night."

"Mmm," was all you could offer, fearing the noises that would come out of your mouth if you opened it.

"I thought about being on my knees," his knuckle parted your folds. In between each phrase he'd attach his mouth back to you, sucking violently. "Your leg over my shoulder," he drove a finger into you, and you gasped. "Riding my face in some dark corner."

"Fuck, Kendall," you sobbed at the image, and the current position he had you in.

"You ever think about me?" he asked, eyes flicking upwards to lock with yours – you hoped you could brand the image into your mind forever – and you nodded.

"Tell me," he commanded, slowly pumping his finger in and out.

"I thought about you…" you took in a haggard breath. "...bending me over the desk in your office - fuck!" he drove another digit into you, you felt yourself opening up even more to him. "...eating me out…on your couch…." you panted, Kendall hummed in response, mouth occupied. "...Sucking your dick… under the conference table."

"Oh, you fucking dirty girl," His fingers curled and found the spot that seemed to quell the ache inside you momentarily, you moaned loudly at the relief and, seeming satisfied with your reaction, he began to repeat the motion again and again. Abandoning his line of questioning, he became quiet, diligently focused on making you come and it was working, a little too well. You'd never been one for dirty talk but you realized suddenly just how close you were, how much it had turned you on to tell your boss all the disgusting fantasies you'd had about him. He was unrelenting.

"Kendall, I'm-" you began, but couldn't even finish before it happened, your body betraying you as you came, hands grasping at the duvet, eyes squeezing shut, shuddering and gasping for air.

"That's it, good girl," he whispered, fucking you through it, not stopping until it was over. Just as you blinked your eyes open, he pressed one final open-mouthed kiss in between your legs before climbing on top of you, smoothing your hair behind your ear and latching his lips to your own once more. You could taste yourself on his tongue. "You're perfect," he said, pulling away, breathless.

"So are you, Kendall," you answered him, hands on his face, and he slowed his movements down slightly to look at you, your fingers fumbling with the buttons on his dress shirt. You were still coming down from your orgasm, lightheaded and a little dizzy, melting against him when he kissed you again. He didn't need to speak, you could hear everything he was thinking, the appreciation, the affection bleeding through his fingertips.

Pushing the dress shirt off his shoulders, you ran your hands down his torso through the smattering of chest hair, grasping at the outline of his cock through his pants. He grunted, pitching forward, his head falling to your shoulder, the weight of his body against you. "Fuck," he swore under his breath.

You didn't want to tease him, you'd already been teasing each other for years. The metal buckle of his belt jingled as you undid it quickly, after he'd already made you come once, you were able to think a little more clearly, but you still hadn't had enough of him.

Pushing him off you, you moved off the bed and sunk to your knees in front of him, before Kendall put a hand on your shoulder.

"I want you," he said stiffly, stopping you from continuing, voice pinched.

"Just for a little," you begged, fingers hooked in the waistband of his slacks. "Please?" you lowered your voice, waiting for him to answer. "I want to suck your cock, Kendall, please?"

Kendall couldn't resist the request, one of his hands sliding into your hair as you tugged away the fabric between you. "Well, since you asked nicely."

He was big, which didn't surprise you, your mouth watering at the sight of him. Truth be told, you'd never been dying to give any of your lovers a blowjob like this, but it felt like a fucking primal instinct now. Kendall watched you intently, big brown eyes, pupils blown wide as you wrapped your lips around his cock, taking him so deep you gagged. His head fell back, the moan he let out echoing off the high ceilings.

His hips rutted forward, involuntarily, forcing you to take him deeper, "Fuckin' so good," he praised. You raised your hand to work the part of him your mouth couldn't reach. At some point, Kendall had unzipped your dress and now he was tugging the fabric off your shoulders along with your bra straps, baring more of you to him.

You'd barely begun to work up a rhythm when he tugged your head backwards, forcing you to release him from your mouth with a pop. "That's enough," Kendall said sternly. "Get back on the bed."

He was more assertive than you'd imagined, but you weren't sure what else you were expecting. It was exactly what you needed.

Your dress was pulled away from you as you obeyed him, your bra unclipped by deft hands, and Kendall settled on his knees between your thighs, hovering over you, two fingers working into your soaked cunt, watching your face as you gasped and whined. A noise of protest left you when he pulled away, but not for long, as his fingers were replaced by the silky tip of his cock, which he slid up and down without giving into you fully.

Kendall ran a hand down the side of your body, letting it settle in the curve of your waist. Perhaps some part of you should've felt ashamed, or self-conscious under his voyeuristic stare but you were so lost in the moment, the heat between your legs crying out for him, you found the compromising position even more of a turn on.

"Please," you pleaded with him, and watched the smirk flit across his face.

He gave himself over in one swift stroke, the air ripped from your lungs as you were forced to adjust to all of him all at once. You clawed at his chest and he pitched forward, shifting his weight inside of you as your lips connected. "You okay?" he asked, tone surprisingly soft, one of his thumbs drawing along your cheek.

"Mhm," you nodded, letting him draw back out of you slowly.

"You tell me if I'm hurting you, okay?"

"I promis-Oh god," you cried out as he slammed back into you.

"You're so fucking wet, baby," he said. His voice sounded deeper than usual, if that was possible, all husky and filled with lust.

After taking him a few times, he worked you open enough to adjust to his size, and you relaxed a little. "Feels so good-"

"I know, baby, I know."

He fucked into you slowly, almost annoyingly so, making sure you took the length of him in full with each thrust, each one punctuated by an extra press forward of his hips so you could feel him deep in the pit of your belly. The sensation was too much, and not enough. Tears leaked from the corners of your eyes, and you were past the point of noises, only able to take long, shaky breaths as his eyes bore into yours, one of his hands gripping your ass to steady your hips, the other on the side of your face. You couldn't hide from him like this. It was the most intimate fucking you'd ever had, equal parts tender and lewd.

"Good girl," He sighed. "You take my cock so, so well, don't you?"

You nodded. "Kendall I-" you fought to find some words to answer his own with, the only thing left on your tongue was love you, which you knew to be true but it wasn't the time to say it.

"I've wanted…" he began to move a little faster, and you panted. "This for….so…." his fingers found your clit, applying just the right pressure. "So long," you let your nails rake down his back and you kissed again, a mess of tongues and teeth, far too lost in the moment to focus on form.

"Me too," he bent down, his teeth sunk into the spot just between your neck and collarbone.

You cried out in both pain and pleasure, the endorphins swirling through your body had you too intoxicated to have any idea that he was all-but marking you as his own.

Kendall watched the woman below him who he'd grown so fond of over the years, half in disbelief, half in a haze of arousal that was quickly coming to its peak. This was wrong. You deserved better than him, he was ruining you, and you both knew it. But he couldn't bring himself to care right now.

He was dying to make you come again, to feel you pulsing around his cock, and he could tell you were close, in the way your cunt grew tighter, the shake in your legs, how you clung to him desperately. He'd only dreamt of this for years, and his own imagination hadn't done any of it justice.

"You're so close, aren't you, sweet girl?" he asked.

You let out a shaky, breathless moan in response, nodding. He liked how needy you were for him, how you could barely string a sentence together when he was fucking you.

This wouldn't be enough, you decided. If you didn't spend the rest of the night letting him fuck you in every position, on every surface in his house even, it still wouldn't be enough. You needed him now, to have all the time. The seal had been broken and every sick, twisted bottled up desire you'd had needed to be satiated. You hoped that he felt the same, though if he didn't, you at least had this.

"Come on, let me feel you."

It was the dirty talk, again, that got you, his honeyed words pooling into the pit of your stomach before you came for the second time that night. You could almost hear the relief in Kendall's voice when he praised you again, fucking you through it, relentless. The rut of his hips became vicious, maybe even painful if it weren't for your post orgasmic high. In fact, you weren't even aware of the fact you were begging him to come inside you until he did, triggered by your own release as he twitched and throbbed and filled you up.

Kendall's teeth nipped at the already-sensitive spot on your neck, you bared the brunt of his weight, your fingers dancing across the skin at the nape of his neck, soothing him in the aftermath. After a moment, he moved out of you, his lips grazing your forehead.

Lying next to you briefly, letting his breathing return to normal, he soon retreated from the room without a word. You curled up in a ball, feeling suddenly lonely, the real consequences of your actions clear in the wake of the rush of hormones and adrenaline. The spot on your shoulder was aching now. There was no coming back from this.

Just as you were regretting every word and action from the entire night, a voice cut through your thoughts.

"Here," you hadn't heard Kendall reenter the room, and you blinked your eyes open just as he was pressing a cold glass of water into your hands. You drank from it graciously, scooting over slightly to allow him to sit on the edge of the bed. He ran a damp, warm cloth in between your legs, then tugged back the duvet, inviting you both to slide under the covers. He wrapped an arm around your waist and pulled you back against him, his energy protective, reverent.

"You okay?" he murmured into your ear. "Was I too rough?"

"No," you chuckled, rolling over to face him, and his brows drew together as he ran his thumb over the welt forming on your shoulder.

"Don't worry," you shrugged him off. "I liked it."

He nodded, and you splayed your hand across his bare chest, letting your eyes flutter closed as your head all but melted into the expensive down pillows on his bed.

"Will you stay?" his voice cut through the silence again, you focused back on him, rather than your daydreams. "You don't have to, it might be nice, I just…I really don't want to be alone right now."

"Of course," you assured him, and he smiled, pulled you close so he could kiss you again, deeply. This was lazy, more explorative, and lacked the desperation from before. But it was nice, gentle, and you appreciated his tenderness after everything that had gone down. "As long as you'll have me," you mumbled against his mouth.

"You'll be here awhile, then," he answered, you could taste the smile on his lips.

This was a bandaid. You knew you weren't the cure, that you couldn't help him really, couldn't erase all his problems. But for now, it was enough.

Part III

[from-the-clouds]

Thinking of a Place - Kendall Roy x Reader

gif by @fleursial​

Masterlist 

Summary:  Of course, your relationship had definitely crossed the boundaries of professionalism on more than one occasion. Part of it was the nature of the job, following him to parties and events, and the amount of time you were forced to spend together in general. Lines got blurred, you both knew too much about each other, and you were more sweet on him than maybe you should be, even though you knew it was wrong, even though you knew he was wrong. 

You would follow him anywhere, even if it was only to stop him from crashing and burning. 

In other words, reader is an advisor to Kendall. Inspired by this song by The War On Drugs

Words: 7.8k

Warnings: Contains spoilers for seasons 1-3 of Succession. Alcohol/drug use and abuse. Depression. Mentions of death/drowning. Kendall Roy existing and being a deeply sad man.

A/N: I've been working on this for quite some time because there's next to no fics about Kendall, and honestly, his whole story breaks my heart and I feel like he needs some love.

I think I might post a part 2, if you'd like. I wanted this to end with them getting together in some way, but as I was writing it, it just didn't seem right in the moment, and was getting too long to keep going. So let me know what you think!

The dim light in the kitchen was a beacon guiding you towards the end of the long, dark, and unfamiliar hallway you crept down. Everyone was asleep, you figured, but you'd been tossing and turning for the past two hours, and finally gave up to make some tea and maybe find a book to read in the hopes one of the two might trick your body into finally going to sleep.

But when you turned the corner into the low lit room, a dark figure slumped over the kitchen table knocked the breath from your lungs and startled you.

"Shit, sorry, you scared me," lifting a shaky hand to your forehead, blush creeping onto your cheeks from adrenaline, embarrassment, or maybe some combination of the two.

Kendall's eyes met yours briefly before returning to stare at some fixed point on the table in front of him. "It's okay," he answered.

Giving him a curt nod, you turned to the cupboards to search for peppermint tea or chamomile or something that might help soothe you. For the past few months, your relationship with your boss – if that was even the right title to call him him, you weren't so sure what he was to you anymore – was on the rocks. Kendall was usually cool and distant, which was normal, depending on how much he was trying to emulate Logan, but the past few days his attitude had even rivaled that of his infamous father, the owner of the company that had employed you for the past few years.

Unfortunately, the veil didn't work quite as well on you as it did on everyone else. Behind the harsh exterior something was rotting, some unhealed sore that would likely be swept under the rug during his next power trip.

"Can't sleep?" Kendall's voice cut through the silence and started you again. It was unclear what was making you so jumpy; perhaps the tension in the room, the source of which seemed to be him. On the other hand, you'd never been to his mother's house before, and you hoped you'd never have to again. There was something eerie about it, filled with expensive furniture but still cold and empty, much like the woman who inhabited it.

Grabbing a container of tea you found, you turned around and shrugged sheepishly. "Yeah, I'm exhausted but…not really having much luck. Jetlag, I guess." Unlike his family, you weren't accustomed to jetsetting around the world and running on little-to-no energy or food like they were.

Turning on the stovetop, you filled a teapot with water and placed it on the burner.

"How was the thing…with your dad?" you asked, turning around and leaning back against the countertop. Kendalls eyes were on you now, flickering up and down your form inconspicuously, but you didn't miss it. It dawned on you then that you were in your pajamas, a loose pair of shorts and a ratty old t-shirt. Realizing how exposed you were and feeling suddenly vulnerable, you crossed your arms over your chest.

"It was fine," he said quickly, and you hummed in response. "Pretty fucking depressing actually," he finished.

"Yeah, well, I can't imagine what that family is going through, losing a son…" you shook your head. Your own family had plenty of tragedies, you knew exactly what it felt like.

Kendall's face twisted, one of his hands closing into a fist. He was clearly upset.

"Is that why you're up?" you asked gently, softening your tone.

He cleared his throat, shrugged. "Sure, I'm a little jetlagged too, I guess."

You nodded. "Makes sense."

"You can sit, if you want," he offered, gesturing to the chair in front of him.

You did.

When you'd first been hired at Waystar, your job had been 'PR Associate', which you soon realized was a more decorative title for what the job really was, a glorified babysitter for the man in front of you. So, after many years of practice, you knew Kendall well enough to tell when he was sober, drunk, high, along with pretty much every emotion he was capable of. It had been your job to recognize those things and act accordingly, and you could still see through them, even now.

"I'm sorry. That must have been hard today."

He had an empty beer bottle in front of him, but he didn't seem drunk. He didn't seem high either, but you almost would've preferred the latter, as the despair pooling in his eyes and practically seeping out of his pores was starting to bleed into your own mood.

"You have no idea."

It became clear that this wasn't just an attitude, or another bender. Something was going on, and it seemed like he was trying to connect, in his own way. "Hey," Reaching out, you let your thumb graze across the back of his hand. "Are you okay, Kendall?"

His eyes met with yours, you could feel them searching, yearning, deciding whether or not to answer honestly. But he seemed to reach an agreement with himself. "I'm fine, thanks. Just same old…bullshit, you know?"

"I know, I'm just…I'm worried about you. Did something happen today?" you pressed, one more time, just to see if he would bite. Even if he wanted to, his pride wouldn't always allow him to be vulnerable. Sometimes, you had to give him more than one chance.

"I, uh-"

The wail of the teakettle cut him off, and seemed to snap him out of it, too. As you darted to turn it off, you offered to make him a cup, which he accepted.

Pouring two mugs of peppermint tea, you set one of them in front of him, clearing the beer bottle away and discarding it in the trash. Returning to your seat at the table, you sipped your tea, letting the mug radiate warmth through your hands.

A comfortable silence settled between the two of you. The truth was, you had a sweet spot for Kendall. Of course, his father, his family, the tabloids had quite a bit of shit to spew about him, and he'd been called every derogatory name in the book. It wasn't all lies, sometimes he was a douchebag and an asshole – two of the media's favorite slights – but you'd seen enough of who he really was to reach your own conclusion.

"Do you think- uh, do you think we could talk, actually?" he asked suddenly.

"Oh, yeah, sure," you answered. "But I need to get my phone or laptop-"

"This isn't about work," he cut you off. "Is that okay?"

"Yeah, of course."

Kendall stood suddenly, chair screeching across the floor. "And we shouldn't be in here, either."

The door clicked shut as Kendall followed you into his bedroom, gesturing towards a seating area in front of one of the windows. You had to admit you were kind of nervous. Kendall wasn't exactly the most stable person you know. For all you knew, you were about to lose your job.

Sitting side by side on an antique couch, you waited for him to speak first, until he didn't.

"So what's going on?"

He shook his head. "Just give me a second, okay? I'm trying to figure out how I want to tell you this."

Your stomach flipped. None of this bode well, and your heart began to beat faster, your chest feeling tight.

Kendall must have picked up on your apprehension, because he seemed to answer the millions of questions spinning through your mind. "It's not, you're not in trouble or anything just….it's about me, something I've done, that I don't feel great about, and it's…it's fucking horrible, okay?"

"But I can't keep-" He choked on his words, gasping for air and then putting his head in his hands. It didn't take him long to regain his composure, clearing his throat. "I just feel like…if you're gonna keep working for me…you need to know."

And so he told you everything about the night of Shiv's wedding. About the boy. About the accident. About his agreement with Logan.

"Holy shit, Kendall."

It wasn't the best response, if you were trying to make him feel better. Which you weren't, not necessarily. But you were pretty sure he wasn't just telling you so you could turn around and make him feel even worse. He looked ill. Pale, exhausted, aching, hurting. Like a wounded animal, eyes red-rimmed.

Of course, you knew of worse things that had happened in the company, but this wasn't nothing. It was pretty fucking terrible, actually.

"I'm a piece of shit, I know."

"Hold on, it's just a lot to process,"

"I know, I don't deserve to-"

"Shhh," you cut him off, shaking your head. "Enough of that." You studied the wood grain of the table in front of you as your brain began to put the puzzle pieces together. "I…so wow, I guess everything makes a lot more sense now. Fuck."

You weren't sure how long you both sat there in silence, you avoiding his eyes and staring into space while everything that had happened over the past year suddenly became clearer, burying your face in your hands. But after a while you turned to face Kendall, who was gazing at you expectantly, eyes dark and full of misery, as if your response could somehow make or break him.

"But Kendall," you began. "You didn't kill him. It wasn't your fault. The circumstances are damning but…you're not a murderer."

You had a lot of questions. A lot. It was clear, though, that Kendall was too distressed to answer any of them, and you didn't want him to have to relive the evening that he was clearly still traumatized by.

"Uh-huh," he answered. "Tell that to my dad."

"I'm not going to tell anyone anything," you assured him.

Or maybe you should. But despite all the damning information you knew about the family, it had become clear that anyone who turned against them never fared well. You knew that well enough after working for Kendall. And you weren't in a position to be out of a job, or worse, sued for more money than you even knew could exist because of a breach of a non-disclosure agreement.

Kendall was relieved, though he knew it didn't solve the problem. Nothing ever would. But keeping it to himself…forever…would be slow torture. He wasn't built for that. "Sometimes I feel like…You're the only person who I can trust."

Hesitantly, you reached out, placing your hand on his shoulder and squeezing it gently, then rubbing soft circles between his shoulder blades. You hated to see him like this. He continued.

"I don't know about the only person," you answered.

"My dad would hate it. He's the one who hired you."

"I think he'll be fine."

"Thank you," his hand rose to his shoulder to clasp over your own, your eyes locked, and for a moment you saw a flash of something unfamiliar cross his face, a magnetic force that was drawing you closer to him, and you broke eye contact to clear your throat and take a sip of your tea, removing your hand from under his own.

"Maybe you should rest," you suggested. "Trying to sleep might be better than not trying at all."

He nodded. "Why don't you finish your tea first?"

The suggestion was purposeful, you knew. Just another way to try to keep your company without him having to ask directly if you'd stick around. And he didn't have to ask, because you did stick around.

When you woke a few hours later, it took a moment for you to remember where you were. It wasn't the room you'd been staying in, but Kendall's. Still lying on top of the duvet, your head was resting in the crook of his arm, your body near his but not touching. He was sprawled on his back. You hadn't fallen asleep that way, but somehow, you must have moved closer to him as you slept, seeking the warmth, the comfort of someone familiar. And clearly, he had done the same.

How you ended up in bed with him in the first place, even though it was on top of the covers, and clear that nothing inappropriate had happened, was still foggy in your memory. And you realized you were even wrapped up in one of his old Harvard sweatshirts.

Through bleary eyes, you looked at the alarm clock. It was still dark out, the early hours of the morning, and you gingerly got out of bed, careful not to wake Kendall, who looked the most peaceful you'd seen him in ages. Before you left, you grabbed a blanket from the ottoman at the foot of the bed, pulled it over his sleeping form, gingerly tucked it in around him and turned off the lamp by his bedside table.

Then you crept away, the only evidence of your stay the empty teacup on your side of the bed. Neither of you would act like any of it had happened.

+++++++++++++++++++++++++++

The elevator doors opened with a ding, and you stepped out into the entryway of Rava's apartment. You still weren't sure why this was the place Jess had told you to come, but she was always informed, so you didn't question her direction.

Surprisingly, Kendall's ex-wife Rava was the first to greet you, rounding the corner, her heels clicking against the marble floors. Whatever was going on here, frustration was clearly written on her face.

"Here to see Kendall?" she asked after you both exchanged pleasantries.

"Yeah, what is he doing working out of here?" you asked.

She bared her teeth in a combination of a grimace and a smile. "That's a great question, isn't it?"

It was clear she was unhappy with the current state of her home, where about a dozen suits were walking in and out of various rooms of the elegant penthouse. Rava dropped the facade just for a moment, stepping closer and leaning in, voice lowering to a whisper. "Sorry, I didn't know you were back working with him again, is everything okay?"

"Uhm, yeah, actually, everything's fine," you chirped, and it was almost a little too obvious you were lying. "I'm an advisor now, believe it or not."

"And you saw what he did?"

"Oh yeah." Truth be told you'd been applying to a job at another company when the press conference popped up on the news. The constant turmoil at Waystar had been starting to wear you down, and despite the fat checks they'd been cutting you, you were wondering if it was worth all the trouble year after year.

"Did you have any idea that he…"

"No. Not at all."

"Right. And you're an advisor?" she questioned. "Sounds about right."

"I can't predict his every move," you shrugged. " I mean, you know Kendall better than I do."

Rava scoffed. "I don't know if that's true anymore."

You'd always liked Rava. Especially at first, she and Kendall were still married when you'd started working for him, even though they were estranged. You spent some time with her, with his kids, and always found her to be the most normal person in Kendall's family. Besides Greg and even Willa maybe – mostly just anyone else who was on the outskirts of the family like you. But as things turned more sour between Rava and Kendall, and you fell out of touch. Obviously, your obligation was to her ex-husband.

"Hey!" You turned to find Kendall standing in the entryway of the apartment.

Rava said goodbye before brushing past him and disappearing down a hallway.

"Sorry about her," Kendall smirked. He may have been coked out, you couldn't tell, because sometimes his confidence was a little too similar to what it looked like when he was in the middle of a bender. "She's a little pissed I'm crashing at her pad for the time being."

Waving your hand, you shrugged off the apology. "She was very pleasant to me."

"Uh-huh," he said, giving you a once-over. You had worn your favorite power suit, which was an oxymoron because you hated having to dress this way for work. "So….what are you doing here?"

"I saw you on the news," you quirked an eyebrow as he stepped closer to you, watching his face change to a slight smile, this time more sincere. He wasn't high, at least not yet.

"Oh yeah?" he whispered. "What'd you think?"

"I mean, holy shit," now you were having trouble being low-key. Truth be told, you were happy for him. Everything he had done was actually…judicious, impressive even. But considering the fact that you hadn't heard a lick of it from him beforehand made you think it was all spontaneous. Even if it was, it didn't matter as long as the public didn't find out, and if all the information he had was as damning as it sounded.

"Holy shit is right," he answered. "Did they…did they call you?"

"Yeah, obviously," You answered. It had been Gerri, of course, the person you were – or at least had been – closest to besides Kendall. And Logan knew it, which was why it was her who called. Kendall was waiting for more information, some kind of verification of why you'd come here. There were only two reasons, and he knew that.

"I told them to fuck off."

"Really?"

"Really," you nodded, biting your lip to hold back the smile, but it didn't work out so well. "I think…I think…this could work. I believe in you, Kendall."

He closed the gap between you, pulling you into his arms, face pressed into your hair. The faint smell of cigarettes lingered on his starched suit, a hint of his expensive cologne still discernible, though you could tell he'd been awake for days. "Thank you," he murmured. "That means a lot." Returning the embrace, you allowed yourself one moment to bask in the rare display of affection.

Not that affection was something that you should need from your boss, but for some reason it felt right. Of course, your relationship with Kendall had definitely crossed the boundaries of professionalism on more than one occasion. Part of it was the nature of the job – I mean, for the first whole year you worked at Waystar you'd had to drag him stumbling out of nightclubs, sneaking him in and out of back entrances and alleyways so the media didn't catch a whiff of his antics. Then there was the amount of time you were forced to spend together in general. Lines got blurred, you both knew too much about each other, and you were more sweet on him than maybe you should be, even though you knew it was wrong, even though you knew he was wrong.

The truth was, whether this was going to work out or not, you had to back him up. Right now was not the time to leave him high and dry. The rest of his family already had, and you felt some sort of responsibility to make sure he was okay. You would follow him anywhere, even if it was only to stop him from crashing and burning.

The elevator dinged, and you both seperated just as Naomi Pierce exited. You ran a hand through your hair as Kendall straightened his jacket, greeting his girlfriend with a kiss. If she'd seen you wrapped in his arms, she didn't give any indication.

"You remember Naomi, right?" Kendall asked. "I thought it'd be good to have her stop by and keep us all company."

You nodded, offering a tight-lipped smile. It actually seemed like a horrible idea. Naomi had been around for a few months, so you'd met her once or twice. She was generally unpleasant, as were most of Kendall's friends or romantic interests. But it was none of your business and he seemed happy, so you could only hope that maybe she was nicer than she let on.

"But hey, uh, Jess is just inside in the living room, and she'll catch you up to speed," he continued, wrapping his arm around Naomi's waist. "I've got a meeting with Lisa Arthur I want you to sit in on, and I'm pretty sure I've just hired the best fucking PR team in New York, so I hope you're ready to jump right in."

The way Kendall's demeanor had changed in mere seconds didn't go unnoticed. It was all business, now. Whatever. You gestured to your messenger bag slung over your shoulder. "Of course I am."

"All right, great, awesome. Well, I'm happy to have you here."

Grinning, you backed away. "Yep, me too." Turning to leave the room, you finally let the fake smile drop from your face. You hoped this wasn't a mistake.

+++++++++++++++++++++++++++

Entering the main room of the event space, you paused to take a look around. There was so much going on, it was hard to keep track of it all, between the nods to Kendall's upbringing, the ridiculous fake magazine covers plastered on the walls, the celebrities and socialites milling about, and the bassy club hits blasting over the loudspeakers.

Luckily, you were a VIP, and you were hoping that the wristband that had been looped onto your wrist mere moments ago could get you into a much less overstimulating area.

You had to say, the party was a great representation of your life that past few weeks, still clinging on, despite seeming destined to fail. Kendall's choices in dealing with the media through this whole ordeal had been questionable at best, and despite your objections, the train just kept going, even though it's destination was becoming more and more unclear.

It was frustrating, because at one point, you truly believed that Kendall could pull this off, become CEO and get Waystar back on track. But unfortunately, as of late, he was more focused on pandering to critics and obnoxiously defending his actions to the public than he was actually accomplishing anything meaningful. His PR team which he'd talked up so much were only yes men and never provided any constructive feedback. He'd fired the only other voice of reason Lisa Arthur, so you were the only one left.

You'd tried every way you could think of to question his choices, to steer him in more productive directions, but he either ignored you or flat out refused. It wasn't fun to argue with Kendall, and you'd had your fair share of spats at this point, so you were feeling a little bitter.

Oh well. You had tonight to get dressed up, be a little irresponsible and hopefully forget about the shitshow that was your job. At least that had been the promise of the evening.

Kendall found you first, sneaking up behind you and slinging an arm over your neck to pull you in for a hug. He was some combination of drunk and high, but clearly not crashing yet, as the huge smile on his face was very telling.

"Hey, happy birthday!" you exclaimed, accepting his hug and then a very overzealous kiss on the cheek.

"I'm so glad you could make it," he chuckled, an arm winding around your waist as he led you out of the river of partygoers towards a balcony area overlooking the party, where it was a little more quiet. "I thought you'd find some excuse to not show."

"Well, you only turn 40 once so…I couldn't miss this," you gestured towards the dance floor below.

"It means a lot that you're here," he took a swig of the beer in his opposite hand, the one on your waist not moving as his gaze became rather intense. You saw behind his dilated pupils all the sincerity in his words, and immediately, the resentment you'd been feeling all but melted away as you relaxed against his touch. You laughed lightly, eyes darting around just to make sure Naomi wasn't nearby, you didn't think you could handle more than one run-in with her catching you in his arms. When you saw that the coast was clear, you loosened up.

Kendall cleared his throat, leaning in. "Listen, I know I said I'm trying to change the culture of misogynistic bullshit that my dad created or whatever the fuck, but I have to say…off the record….you look fucking hot."

You rolled your eyes and swatted at him playfully. "Oh my god, shut up."

"I mean come on, this dress…it's definitely working for you," he gave you a greedy once-over, he couldn't help himself. "I like it alot."

Giggling before finishing the drink in your hand, you leaned in to whisper in his ear. "I thought you might," you said coyly. He laughed as you drifted closer to him. It'd been awhile since you'd engaged in a shameless flirt with him, which unfortunately, was one of your famous pastimes. Things had been far from playful between you both as of late. You were pretty sure the edible you took before you left your house was kicking in, because you were feeling lightheaded, each graze of his hand left your skin tingling in its wake.

"What's this?" you pinched the shoulder of his jacket - which was a little ridiculous - you preferred the way he looked in his tailored suits, but you wanted him regardless. "I like this."

"Gucci," he answered.

"Holy shit, you went all out."

"You gotta," he shrugged.

"Well, I'm happy to be here, I hope you're having a good night," you let your hand rest on his bicep, smiling at him.

"I am, I hope you are, too."

You both seemed to realize where you were at the same time, slowly inching away from each other, his hand leaving your waist, the guise of professionalism back up again even though you were both some variation of high and drunk.

Kendall's gaze shifted over your shoulder. "Hey," you were interrupted by a familiar man's voice in your ear. You turned to find your date for the evening, offering you one of the two drinks in his hands.

"Thanks!" you accepted it graciously. "Uh, Kendall, this is Ron, Ron, Kendall."

The smile had disappeared off Kendall's face, and they shook hands, exchanged pleasantries, as you sipped your drink and watched. Ron was handsome, dark curly hair and big brown eyes. You wished you knew more about him but all you knew was that he was a lawyer, in tech or something, and he had a California King sized bed in his apartment. He was the perfect, cute distraction that you needed.

Kendall excused himself shortly after, and you ended up with your shoes off, on the dance floor with your date. Drinking and partying had never really been your 'thing', but it was usually a means to an end doing business, so you'd grown to enjoy it, even if it was just for convenience sake.

A few hours had passed, and you were now thoroughly buzzed, moderately stoned, and a little sweaty. You'd sampled all the hors d'oeuvres, let Ron pull you into a few dark corners to make out, and had done a few laps around the space, checking out all the details Kendall's PR team had put together. You were thankful that organizing it wasn't a part of your responsibilities, as it was pretty chaotic.

Eventually, you somehow got separated from Ron, and ended up in the super VIP area, which was some sort of treehouse-themed situation, and you ran into Kendall again.

"Hey," he said, grabbing you by the wrist and pulling you aside once more. You laughed at first, wondering if he was trying to engage again in some light flirting. "I didn't know you were, uh, seeing someone."

"Oh, Ron?" you asked. "Mmmmm, yeah we're not really seeing each other. It's not really…we're just fucking." Too far gone for finding a way to nicely explain what a sneaky link was, you winced at your own answer. You'd never spoken to Kendall so candidly about your personal life.

"Right, got it," Kendall answered shortly. He wasn't in the same state as he had been earlier, now more stiff and serious. Perhaps the drugs had worn off, or things weren't going his way. You'd noticed that Shiv and Roman had made an appearance but did your best to avoid them, so you wondered if that was making him antsy. "That's good, actually, because I need you to do something for me."

"Like what, like work?"

"Yeah uh-huh, kinda."

You clicked your tongue. "I don't know, I thought everyone was supposed to be able to let loose tonight, I thought work wasn't supposed to be a thing. I mean, they tried to take my phone when I came in."

"And you didn't let them?" he frowned, and you realized this was a completely different Kendall than the one who had been hitting on you a mere hour before. He opened his mouth to speak again but then closed it, shaking his head.

"Hey are you okay?" you asked, putting your hand on his shoulder.

"Yeah, I'm fucking fine," he shrugged away from your touch. "But really, you still have your phone? What are you, spying on me? Taking notes to pass off to my dad like you used to?"

"What? Kendall, no, I just…I didn't…"

"Didn't what? Think the rules apply to you?" Kendall asked. "What's been going on with you lately, anyways?"

"What are you talking about?"

"All the fucking negativity, just like, killing the fucking vibe, I mean-" he cut himself off. "Whatever, listen, walk with me."

"Ohhkay?" you let him put a hand between your shoulder blades as he guided you through the crowd towards a lounge area. Stopping just short of it, he gestured to a handsome blonde man who was scrolling on his phone looking bored.

"You see that guy?" he gestured towards the man. "Do you know him?"

"Am I supposed to?" you wondered where this was going.

"It's Lukas Mattson. He owns Gojo."

"No shit," you raised an eyebrow.

"Waystar is trying to buy Gojo, and I think Roman and Shiv are trying to make a light approach tonight. I can't let that happen, or we're fucked."

"And?" you had no idea how this involved you.

"Listen, he told me earlier he was trying to find someone to hang out with tonight-" Kendall paused when he saw your face, stuttering. "Well, the exact words he used were privacy, pussy, and pasta."

"You're a super VIP, so you can get into pretty much any of the more quiet rooms. I just need you to flirt with him, get him out of the public eye, keep him company, you know, whatever. And hey, you might get a more serious situation out of it than whoever the fuck I met earlier. You're both kind of into that hippie shit. Don't worry, I'll introduce you."

You felt sick to your stomach.

Without waiting for your response, Kendall dragged you forward, but you didn't budge. He turned around to look at you. "Come on."

"No," you said, but he either didn't hear or didn't care, you staggered forward fighting against his weight pulling you forward. "No, Kendall, hey, stop!" You hissed, digging your nails into his arm until he finally turned around to face you.

"What's the issue?" he asked, irritated, as if he was allowed to feel that way after what he'd just asked you to do. Sure, you knew how to turn on the charm to close a deal and it never hurt to be a little coquettish, but it was always at your own discretion. This was just flat-out offensive. And really, deep down, it hurt.

"I- I mean," you stuttered, trying to come up with something. The room felt like it was closing in on you, your face growing warm, your throat dry. "I don't really think this is a solution to your problem, I mean, why don't you just kick Roman out?"

"Kick my own brother out of my birthday party?" Kendall raised his eyebrows. "Oh yeah, the media would fucking love that, wouldn't they? They'd eat that shit up, I'd be asshole of the year."

"Kendall, I don't understand why you are so worried about what everyone thinks of you." you asked. "Who cares? He's been treating you like shit."

"You're fucking unbelievable, you know that?" Kendall shot back. "What's your fucking deal anyways? I mean, first the phone, now this? You've spent the last few months shooting down any decent idea I have, are you trying to fuck this whole thing?"

"What?" you were incredulous. "No. Kendall, I'm trying to protect you."

"Uh-huh, yeah, well, I don't fucking need you to do that for me anymore, okay?" he hissed.

"That's not what I meant, and you know it. I'm just trying to make sure you're making the right decisions okay? Sometimes you need to think things through, I mean, you've been really impulsive lately and-"

"Well if I wanted your two cents I would ask, okay?"

"I've fucking bitten my tongue more than I can count and you want to act like it's just me being a bitch? I'm not going to let you whore me out to your business partners whenever you want." At this point you were just yelling. Luckily, there were very few people who seemed to even notice it over the music and general debauchery happening.

Kendall's eyes darted around. "Lower your voice."

His patronizing tone only spurred you on, and stepped forward so you were inches from his face. "You don't want my advice, so what am I even here for?"

"That's a good question."

You let out a sharp exhale, your stomach dropped. It was impossible to mask the damage his words had done. Tears burned along your waterline. God you'd never cried in front of him before, this was humiliating. "Fuck you," you jabbed your finger into his chest, hard enough he stepped backwards. You couldn't keep your voice from shaking. "I believed in you."

You stepped backwards as he met you with a dead-eyed, blank stare, like your words weren't even registering, like none of this even mattered to him, like you hadn't been loyal to him for years, like you weren't his only real confidant. Swallowing hard, you swiped at the tears under your eyes.

"Enjoy your party," you said, turning on your heel. You wouldn't give him the satisfaction of looking over your shoulder on your way out.

+++++++++++++++++++++++++++

When you first got home, you had a good long cry. The whole shitty mess of tonight found you surprisingly heartbreaking, especially because you weren't sure if you could ever make amends with Kendall after everything you said. Of course, there was a sort of relief in finally giving him a piece of your mind, but you could've handled it better. You weren't much of a crier, but once the years worth of pent up emotions were released, it was hard to stop the floodgates.

Enough time passed for the alcohol to wear off, and thanks to a lengthy bedtime routine, a few glasses of water, and smoking half of a joint you rolled, you were finally able to calm down.

Kendall hadn't known what it meant to be home in decades. Or maybe he really never knew what a home was. But it wasn't his penthouse suite where his girlfriend had taken him after the party. There was only one person, besides his father, who knew who he really was, who had never betrayed him, and the last thing he had done to her was terrible. But he couldn't think of anywhere else to go.

You were half asleep when there was a knock on your door. It was well past any reasonable time for a neighbor to be reaching out, and you checked the peephole out of caution.

Kendall was on the other side. You couldn't see much, but he was hunched over, leaning against the door. Maybe, if you ignored him long enough he'd go away. But you shifted your weight and the creak of the wooden floorboards gave you away before that was even a possibility.

"I know you're in there, open up," you heard him call out, loudly, too loudly. You had neighbors, thin walls, and an overly-attentive landlord.

Sighing, you opened the door, not bothering to unlock the deadbolt and peeking through at him. "Kendall, go home."

"Please let me in," he wedged his hand in between the small crack of the door. If he really thought it would stop you from slamming it on his fingers, he was wrong. But it would be a risky move.

He was not okay. You could tell immediately. He never was, but this was different. And you were angry at him, still, but it seemed like sending him back down the hallway would get you into more trouble than it was worth. The obligation to protect him was more deep-seated than you'd thought.

You groaned loudly, shoving his hand out from between the door and it's frame. "Fine," you hissed, letting him inside. And he walked past you, but paused in the tiny entranceway to your apartment, looking at the floor. For a moment, you wondered how he even knew where you lived, but you supposed this was the address on all your paychecks, so it wasn't exactly a shock he'd found you.

"I'm sorry," he said suddenly, looking up at you. You crossed your arms. "I fucked up. I shouldn't have done that to you, tried to use you like that. But really…I shouldn't have talked to you like that and I…I'm sorry I made you cry."

You sighed. "That's all this is about?"

"Well, no…" he began. "I mean, yeah, uh, maybe…I guess."

"Okay, well, thanks for that," you said flatly. There was clearly something else going on, but you weren't even sure if you had the time or energy to try to get it all out of him. "And I'm sorry, too. I said some shitty stuff."

"It's fine, I deserved it," he answered quickly, and snuck a glance over at you. You knew what you looked like, the complete opposite of earlier, hair unkempt, glasses on, pajamas on. "You're not going to quit, are you?"

"Ugh," you rolled your eyes. "Seriously? This couldn't have waited until tomorrow, Kendall?"

He lowered his head again, refused to make eye contact as you glared at him. You weren't going to speak any more, you were still frustrated with him. Hell, you weren't even sure if you really accepted…or believed his apology.

"No." Kendall swallowed hard, raising his gaze from the floor and looking at you. Beyond his over-dilated pupils was a deep, deep despair that threatened to drown you along with him. "I just, uh…can you?" He stepped forward, arms slightly open. You knew what he was asking for, even if he couldn’t bring himself to do it.

"Come here," you murmured. Meeting him halfway, you closed the gap between him, wrapping your arms around his shoulders. He clung to you in return, tightly, desperately, burying his face in your neck and holding on like his life depended on it. He let out a choked sob, muffled by your shoulder, and you could feel his body tense up, trying to hold everything back.

"It's okay, Kendall," you whispered, turning your head to brush your lips over his temple, the urge to comfort him unavoidable. He could probably count on one hand any sincere act of kindness he'd ever encountered. There was a chronic desire for genuine connection that was never fulfilled, he was constantly rejected by the people he was supposed to love and trust. And maybe you couldn't fix it all, but you could at least try. You let him be the first to pull away, which took some time. "Why don't you come in and sit down, let me make you something to drink, okay?" you rubbed his arm, and he clutched at your hand clumsily. "Come on, take your coat off."

Kendall took off the ridiculous jacket he'd been wearing all night, and you hung it up, making your way to the kitchen and pouring him a glass of water while he sat on the couch.

"This is so fucking pathetic," he said, under his breath but loud enough to hear, and you passed him the glass, which he sipped from once before placing on the table in front of him.

"If it makes you feel any better, I cry every year on my birthday," you said, before grabbing a blanket from a drawer in your coffee table and draping it over his shoulders.

"Really?" he asked. "Why?"

You shrugged, rubbing his back. "I don't know. It's always a letdown, isn't it? Getting older?"

He snorted. "Uh-huh, I guess so."

Kendall leaned back, and you shifted your weight to tuck your feet underneath you, putting your arm over the back of the couch and facing him. "So uh, what happened with that guy you were with earlier?"

You laughed dryly. "Ron? I don't know. I left without him. I told him he could stay, so…who knows."

"I was uh, a little surprised he wasn't here," he said.

"Mmm, well if he wanted to be here he had the option," you answered. "Anyways, he was talking to a girl before I left so…I'm sure he's fine."

"Uh-huh."

The two of you sat in silence for a moment, and you were trying to think of a way to make him feel even the slightest bit better. "Listen I know it's technically not your birthday anymore, but do you want your present?"

"Uh, sure…" Kendall looked at you. "You didn't leave it there?"

"No, well," you looked around sheepishly as you stood up. "I took it when I left, cause you…hurt my feelings, and I was pissed off," you joked.

He smiled slightly at your words, but when his expression neutralized again he looked in even more pain than before. "I'm sorry," he repeated his words from earlier.

"It's okay, it was a little dramatic of me anyways, because I don't know what I'd do with this." Picking up the large gift from behind the couch, you passed it to him and sat back down, looking over his shoulder.

Tearing away the wrapping paper to reveal what was underneath, Kendall paused. "What...is…"

"Italy, Lake Como," you answered, leaning over his shoulder to look at the watercolor painting that had taken weeks to complete. "I don't even know if you remember, it was last year, before the shitshow. Some conference or something everyone had to go to. I'd never been before, and it was so beautiful. It was only a few days, and you seemed so happy."

You pointed to a small figure in the corner of the landscape, the silhouette of a man smoking, leaning over a balcony. "You can't really tell, but that's you."

"It's beautiful." Kendall shook his head, fingers tracing over the image of himself. "Who'd you hire to do this?"

"Oh, I did it," you answered. Kendall looked over at you. "I have the reference photo, I can show you."

In hindsight you weren't really happy with yourself for the amount of effort you'd put into this – it was too much, in your opinion. While you were painting, there were several times you almost scrapped it, as you weren't even sure if he'd like it, and it cost you next to nothing. You'd never had much luck buying gifts for his family, as there was nothing they couldn't afford and buy for themselves. For Kendall at least, this had seemed obvious.

"Holy shit, I didn't know you could do this," he looked back at the painting. "This is like…fucking professional."

"Oh, no not really, it's just a hobby."

"No," Kendall shook his head. "Just take the compliment."

You felt your face grow warm, a little bashful. "Well, thanks."

"No, thank you," he said. "I don't-" began, before his voice cracked.

"Okay, stop that," you smiled, but felt your face fall when he set the painting aside. "What, do you hate it or something?"

"No," he said, and put his head in his hands. "Not at all."

"No please," you giggled, trying to get him to pep up. "I wasn't trying to make you cry, you can't cry right now."

"I don't deserve this," his voice trembled. "I was so shitty to you, I've been so shitty. And you fucking do this kind of stuff for me."

"Stop it," you scolded, wrapping your arms around him from behind. "If all of that was true, I would've quit a long time ago. You've done a lot for me."

Kendall shook his head, but sat up straighter, clearing his throat. "Uh-huh. I'm not so sure about that."

You took a deep inhale, because you weren't going to waste energy arguing about something so petty.

"What's really going on, Kendall? Did something happen tonight?"

He was silent for awhile, so long you weren't even sure if he had heard you. But before you could speak again, he did.

"I don't think I'm gonna win anymore. My dad wants to buy me out. I think he knows something…something I don't."

Kendall frowned before continuing. "Tonight was…I don't know if anyone there really cared about me. Naomi…" he shook his head. "Even Shiv and Roman, they were just trying to get at Mattson. My dad….he's ruined them…"

Kendall began to weep again, and you pulled him back into your arms gently. "I'm so sorry," you murmured, and he curled closer to you, his head falling to your lap. Carefully, you carded your fingers through his hair, massaging his scalp. Kendall had never, ever been this open with you. Maybe one other time. But this was a different type of vulnerability, a deep wound that opened well before he crashed that car into the river.

"Maybe you should get out," you said quietly. "Take the money, Kendall, and get out. Everything Logan has put you through can't be worth this."

He turned and looked up at you, his hand clasping over yours, bringing it to hold it over his heart. "Maybe I should."

"By the way," you added. "I care about you."

You knew tonight wasn't time for some grand confession. Not while he was in this state. So it was the closest you could get without saying it outright.

"Thank you," he mumbled. "You're the only person who really knows me."

You gave him a sad smile in response.

"I'll leave soon, I promise."

"You can stay," you answered softly.

And so he did, staying with his head on your lap and you leaning back against the couch cushions. The traffic outside, which once used to keep you up all night, eventually lulled you both to sleep.

Part II

[from-the-clouds]

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

gif by @televisionchronicles

Part One | Part Two | Fic Playlist | Masterlist

Summary: You attempt to piece your life back together after your time spent with Kendall, and finding out your job is likely obsolete.

Words: 6.9k.

Warnings: Contains SMUT (minors dni) unprotected sex. Depression. Angst. Kendall Roy existing and being a deeply sad man. Spoilers for seasons 1-3 of Succession.

A/N: So uh, I didn't think I'd continue this but I was kind of itching to write something longer with Kendall, and I really liked these two. So I sat and thought about how to keep this going and have a plan. All the kinks aren't ironed out yet, but I am assuming there will be at least 3-4 more parts, maybe. Hopefully ya'll are interested/excited & down for the ride.

I apologize in advance for any inaccuracies in business procedures or anything like that while I progress through this storyline. I write for fun while still working full time, so don't always have time to deeply research every story I post. But I've been really enjoying writing this. Sorry in advance for allllll the angst. And sorry to my former english teachers for using flashbacks. Also, all flashbacks are in italics

Also please go listen to the playlist I made for this story! Music is such a big part of the writing process for me and I love when writers post what they listen to when writing! Helps me discover new stuff.

Frantically typing on your computer, you were trying to get all your work done before the end of the day. For the first time in years, you had time off for the holiday, and you were spending it alone at a resort in The Bahamas. You were usually alone on the holidays anyways, but at least this year it wouldn’t be spent in your shoddy apartment.

When you heard a knock on your office door, you looked up, to find Kendall poking his head in. “Oh, hey Ken, come in,” you frowned. He rarely came to visit your office, so you wondered if you were in trouble, especially when he shut the door behind him.

“Hey, you’re leaving tonight?” he asked.

“Yeah, I got a flight to catch in a couple hours,” you said, eyeing him as he stepped forward, somewhat awkwardly. Fuck, fuck, fuck. You tried to figure out what you had done wrong recently that might warrant a closed door meeting. During your last one-on-one with him you had gotten rather snippy about an acquisition he wanted to make that you thought was a poor choice, and the conversation ended with him commanding you to leave his office. But honestly, that type of thing had happened before and hadn’t been a big deal. Maybe this time it was, and you hadn’t realized it.

“Uh-huh, I wanted to catch you before you left. Give you this.”

“What?” you sat up straight in your desk chair, leaning forward as he presented you with a very professionally wrapped gift you hadn’t noticed he was holding until now. “What is this?”

“You can open it,” he stood in front of you, waiting, crossing his arms.

“Kendall, seriously?” You asked, looking down at the white box, emblazoned with the Dior logo. But you did as he instructed, undoing the crisp ribbon and lifting off the top of the box. Reaching inside, you pulled out a very intricately designed piece of what felt like…silk.

“Wow this is…” your eyes widened as you pulled the scarf out of the box, admiring the detail, the feeling of the fabric slipping delicately through your fingers. “It’s beautiful.” You shook your head, unable to find anything else to say, unable to express any emotion besides pure shock.

“Uh-huh,” he said, watching you closely. “I’ve been clean for a year now, and uh, I know that uh, you aren’t still…doing the same job you did when we met but uh, I can’t help but think you’re partially responsible for helping me get my shit together, so uhh…I wanted to thank you.”

With a fucking Dior scarf? What were you going to do with a Dior scarf? You didn’t even want to know how much it cost, even though you were absolutely going to look it up when you went home just to see. Probably more than you spent on groceries in a year. You did pretty well for yourself at this point, in fact, you’d been pretty excited when you were able to buy a dress one time at FreePeople that wasn’t in the sale section, but Dior? That didn’t seem attainable, ever.

“If you’ve been clean for a year, you should buy something for yourself, not for me,” you said, wryly, setting down the scarf and offering a smile. You really, really, hated receiving gifts, there was something about it that made you feel guilty, especially when it was unexpected. Because of that, the only thing you could do besides blush and avoid eye contact was crack a joke.

“Uh-huh, well, it’s Christmas, too,” he said, as you continued to inspect the gift. “And…I’ve seen you wear stuff like that. They’re hand painted, you know.”

“Yeah,” you shook your head, taking a deep breath. You already knew that because you’d read it last week in an art magazine. This was, in theory, a very good and considerate gift. But, you wondered if it was even appropriate to wear something like this around the office, if word got out that he’d bought it for you.

Pushing back your chair, you stood, circling around your desk to approach him. “Thank you, Kendall, it’s beautiful. Very thoughtful.”

In some deeper part of your brain, you thought this was a really hot thing for him to do for you. But you were going to pretend like you didn’t.

So you hugged him carefully, and he seemed surprised at first, taking a second to hug you back, embracing you cautiously. As you pulled away, however, he pressed a gentle, well-mannered kiss to your cheek. One of your hands remained on his shoulder as you looked at him.

“You should be really proud of yourself, you know. Staying sober for a year…still in this shitshow?” you chuckled, gesturing around the office, shaking your head. “I’m proud of you. That can’t be easy.”

Squeezing his shoulder, you dropped your hand. He chuckled, looking down, putting his hands in the pockets of his suit jacket. “Uh-huh…fucking, it’s not. But uh, thanks. I should let you get back at it, though. Merry Christmas.”

You smiled. “Merry Christmas, Kendall.”

--- --- --- --- ---

Sunlight streamed through cracks in the curtains, and it took you a minute upon waking to recognize where you were.

It was warm. Comfortingly, blissfully warm, and you turned your head to find the source of the heat, and the soft sighs next to you.

Kendall.

His head was on your shoulder, your arms wrapped around him, holding him close, while one of his hands splayed across your belly. Snippets of the night before flashed through your mind, his mouth on every part of you, body stretched out over yours.

Now, he looked so peaceful, curled around you, snug, fast asleep. The air in his place was cool, you could feel the goosebumps rising on your exposed skin, but he was like a furnace coiled against you. You didn’t mind.

“What is this?” he had whispered at one point the night before, while you were still trembling in the wake of an orgasm, his arm across your waist, pulling you back against his chest. The two of you had been up nearly all night, you’d let him take you however he wanted, however you begged for him, a pathetic, whiny mess. You obeyed every order he’d given. And he had been so, so good to you.

Your stomach tightened at the thought of it, a dull throb returning between your thighs, as if you hadn’t had enough. It would probably be awhile before you did have enough. And that was the issue.

There wasn’t an answer to his question you felt you could give. It was Kendall, after all, and you liked Kendall. You could feel that this wasn’t a one time thing. But from a practical standpoint, maybe it should be. Or maybe not. Your mind kept batting the possibilities around. Even now, there was a deep impulse to sneak out of his arms, gather your things, and leave the apartment without saying a word.

“Hey,” a low voice interrupted your emotional turmoil, as your eyes locked onto the man who was causing said turmoil. So much for leaving without waking him, you thought, staring into his dark eyes.

“Hey,” you answered, as Kendall shifted his weight, sliding from underneath you. It allowed you to fall deeper into the down pillows, trapped beneath him as he hovered over you, arm around your waist.

“Have you been up for long? You should’ve woken me.”

“I didn’t want to,” you answered. “You needed sleep.”

“Uh-huh,” he murmured, leaning forward to nuzzle his face into your neck. “How sweet.”

You were trying to figure out a way to stay in this bed longer. Leaving meant facing consequences. But unfortunately, you had to pee.

“You sleep okay?” he asked.

You giggled, the vibration of his voice, low and gentle in your ear made you shiver. His lips found a place on your neck, pressing there lazily, absentmindedly. “Yeah, I did.”

Of course you did. It would’ve been nearly impossible not to sleep well after last night, made up of several rounds of intense, passionate sex. It was all fucking, napping, talking, and then fucking again, until you both eventually found your way to sleep.

“Are you hungry? Do you need to shower?”

You thought for a moment. If you said no, made some excuse and dipped out awkwardly, he’d definitely ping it as being weird. Then you’d actually have to talk to him about what you’d both done. Maybe if you pretended like everything was okay, you wouldn’t have to. Also, unrelated, but you knew his bathroom was probably much nicer than yours, and you kind of wanted to experience showering in a billionaire's shower. “A shower might be nice.”

“Go ahead,” he pulled himself away from you, tucking a piece of hair behind your ear tenderly. Why was he being so nice? It was like he could sense your apprehension.

The shower felt nice, an opportunity to wash away the filth of the night before. And while you kind of hoped that Kendall would join you, you were a little thankful that he didn’t, ultimately. It was good to have a little space, an opportunity to clear your mind. Even if that space left room for all the doubts that had been in the back of your mind while you let Kendall have his way with you.

Why did you do that? That was a terrible idea. Everything’s gonna change now. Was it worth it?

Sure yeah, it was. And you needed to stop acting like you hadn’t been in your right mind when you’d made the decision. You had been. You knew exactly what you were doing. You had wanted it.

There were ample towels to dry off with, you wrapped one around your head and one around your torso when you were finished, brushing your teeth with a spare toothbrush you found still in it’s packaging in one of his drawers. After that, you felt a little more human, looking in the mirror and noticing the lovemark Kendall had left on your neck. You knew it’d be a bitch to cover up. A few bruises on your hips left a roadmap of other places he’d touched you. Thinking about it again had your stomach flipping and you could feel yourself getting flushed.

But you couldn’t let your mind wander. You had to focus on your exit strategy.

Leaving the bathroom, you ducked to pick up the dress you’d worn the night before, that had been discarded on the floor, along with your bra and panties. You heard the sink running in the other bathroom - yeah, his fucking master bedroom had two bathrooms – and assumed Kendall was freshening up as well.

Now would’ve been a good time to sneak out. But the idea made less and less sense the more you thought about it. You knew deep down you would’ve never done it to begin with, because it was downright cruel. And you didn’t want to be cruel. You could have your dramatic mental breakdown about this later. You had to keep it together, for him.

“Here, let me help,” you were attempting to zip your dress back up as Kendall’s voice interrupted you, reentering the room. He had changed into a sweater and sweatpants.

Stepping behind you, he helped you zip the dress all the way up, squeezing your shoulder gently, and you turned around to face him. “Do you want breakfast or anything?” he asked.

You shook your head no. Really, you were overcome by the urge to ask him if he’d get back in bed with you just to cuddle. He looked so cozy in that fucking sweater. But that was no good, you figured. “No, I should probably get going, Ken.”

“Uh-huh, okay,” he pulled away from you slightly, looking a little wounded. Something you wouldn’t have noticed if you didn’t know him. “You okay?”

Fuck. You nodded, lying. “I’m fine, sorry. I just feel like I’m imposing.”

“Well, you aren’t,” he smiled lightly, reaching out to pull you closer to him, his hands steady on your hips, touch still igniting a flame within you. “But if you need to leave, let me at least walk you out. You want me to call a car?”

You shook your head no. “I don’t mind walking. But thank you.”

The walk would clear your head, or so you hoped. A smile teased at the corners of your mouth as you made your way down the hall together, pausing to put on your boots and grab your purse.

“So, is this it, then?” Kendall asked, stopping you as you were about to slip out the door, his hand clasped around your bicep, holding you back. You hadn’t hugged him, hadn’t kissed him since you’d gotten out of bed. His eyes were wide, earnestly searching yours. Oh my god, you really couldn’t refuse him. Not just from a physical standpoint but also just…because it was him. You couldn’t forget everything he’d been through. “Will I…can I see you again?”

You tilted your head. “Is that…what you want?”

Kendall nodded. “Uh-huh…I do, I- yeah. I do.”

“Okay then uh, maybe Friday?” It was only a couple days away. Hopefully by then you might have your thoughts sorted out.

“Of course, I’ll call you.”

You smiled, nodded, stepped towards the door but he stopped you again.

“Hold on, come here,” he said, pulling you close, into his arms. He kissed you again, reverently, hand cradling your face and slowly parting your lips with his tongue. Tears bit at the back of your eyes, overwhelmed by emotion - guilt, sadness, uncertainty, affection - spinning through you all at once. All that, and you still couldn’t help but smile against him, as he pulled away slightly, just to wrap you tightly back against him. Returning the hug, you let your fingers graze between his shoulder blades.

“Thank you,” he said into your ear. “For everything.”

“Of course, Ken,” you pressed your lips to his cheek, his eyes fluttered closed. “I’ll see you soon, okay? Take care of yourself.”

He nodded. “I will.”

--- --- --- --- ---

The phone rang several times before the person on the other end finally picked up.

“So let me guess, you’re finally jumping ship?”

You were sitting on your couch wearing sweats, curled up under a blanket, laptop open in front of you. On your TV were reruns of MasterChef, but muted, as you were more occupied with the person on the other line.

“Oh hey Stewy, glad to hear you’re doing well,” you answered, pushing back the cuticle on your ring finger with your thumbnail. “I’m doing great, thanks for asking.”

“Come on, you of all people should appreciate skipping out on general pleasantries,” he answered, clucking his tongue. He paused on the other line, lowering his voice before speaking again. “I know there’s only a handful of reasons you’re calling me.”

“Mhm,” you affirmed. “Care to guess which one?”

“Well, if you really wanted to make my day you can imagine what I’d like this phone call to be about…” he paused, and you rolled your eyes, even if he wasn’t there to see it. “But in light of current events I’d suspect the real reason isn’t fun.”

You chuckled lightly. Stewy was the biggest flirt you’d ever met in your career. It almost would’ve offended you, if he wasn’t equally as suggestive with every other person he met, Kendall included. In fact…maybe even more so with Kendall than anyone else. But that was an analysis for a later time. “Yeah, well I hate to burst your bubble, but it’s not fun.”

“That’s too bad. You know, I always figured you’d reach out. I’m just surprised it wasn’t sooner.”

Throwing the blanket off your lap, you stretched your hands over your head. “How do you mean?”

“Well, Kendall and I used to be friends…and uh, even considering that, I don’t think I’d last long working for him. You held out a lot longer than I expected. But then again, he did seem awfully….protective of you.”

“Kendall’s not the issue,” You said. Kendall was frequently, and currently, an issue, but…in a different way. “He is…was a good boss.”

“How’s he handling this news?”

“I don’t know,” you lied. “I mean, I’m sure he’s not thrilled but uh, hopefully he’ll figure things out.”

“Yeah, well, we’ll see about that. If you’re still on good terms with him, I’m surprised you’re calling me.”

You sighed. This man was kind of exhausting. Sometimes, you felt your brain wasn’t meant to work the same way the people in this world did. To you, there weren't a thousand thinly veiled messages being communicated in this call. Right now, you were just trying to find a job. “Well, you and I have always gotten along. And I trust you-”

“You shouldn’t-”

“Can you let me finish? Damn.” you snipped, sitting up straight and rolling your eyes. “I mean that in the simplest sense of the word.”

“Atta girl.”

It was easy to picture him now, leaning back in his chair with his feet on the desk, maybe strutting down some hallway with one of his hands in his pockets, the other holding his phone to his ear, always in a rush to get somewhere, each conversation he was running off to always more important than the last. Honestly, you were a little surprised he picked up at all.

“You’re a well connected guy, Stewy,” you said, standing up, beginning to pace around your small living area, stepping in between the cracks of your wooden floor absentmindedly. “And I’m looking for work. It kind of makes sense you might help me out. Keep an ear out, if you hear of anything.”

There was a long pause on the other end of the line. “I mean, I’ll see what I can do. I can give you the number of a good headhunter, for starters.”

“That’d be great.”

“Yeah, I’ll have my assistant send it over. You should send me your resume, too. And uh, don’t go hopping on to anything too quickly. Talk to me, first. And who knows? Ken might still need you.” He started to talk a little faster, which told you you maybe had 30 seconds before his attention was pulled elsewhere.

“What do you mean?”

“Well, I don’t know. Logan can’t be the only one to make this decision, selling all of Waystar. There’s other people- hey, sorry, I gotta run to a meeting. But uh, yeah, let’s keep in touch.”

The line went dead before you could say goodbye and you sighed. All things considered, that went better than you were expecting. You just hoped it would pay off.

--- --- --- --- ---

The few days away from Kendall were exactly what you needed. It sounded counterintuitive, considering that he’d been on your mind most of the time. But you’d worked through the kinks.

You’d come to a conclusion, or really, a lack of a conclusion. Logistically, it was a bad idea to sleep with your former boss. Doing this was setting yourself to be hurt. There was no way it would ever work out. So you decided to keep doing it, anyways.

As someone who had spent all their life buttoned up, sacrificing their own happiness to do the right thing, the practical thing, the good thing, you were sick of it. It wasn’t fun. It wasn’t rewarding. It just made you more miserable. You wanted to do the bad thing. It felt good to do the bad thing. And if he needed someone, why couldn’t it be you?

One trembling hand reached out to open the front door of your apartment, finding Kendall on the other side. The last time he’d been here, you’d been unprepared. Hell, the last time you’d seen him, you’d been unprepared. This time, you’d cleaned your place, you’d made dinner, you’d showered, shaved, made sure your underwear was matching, spent the better part of your day just making sure you looked your best. At one point, while you were on your hands and knees scrubbing the kitchen floor, it dawned on you that Kendall had probably never had to do anything like this, and it sort of pissed you off a little, nearly making you reconsider inviting him over in the first place. But then you immediately changed your mind.

Now, you half wished you hadn’t invited him over here days ago, and that he would’ve just showed up without any plans in place. Because all of the preparation, all the anticipation, had given you too much time to think.

“Hey,” Kendall stepped over the threshold, into your space, looking around. He looked handsome, of course, wearing a fucking sport coat and brown pants. Underneath the blazer was a crisp white t-shirt, unbuttoned just enough so you could see just a peek of his chest hair. Coming into your place looking like a professor who you’d do anything for to pass his class. It kind of pissed you off.

“Hey,” You’d already started drinking before he arrived. Kind of because you didn’t want to be drinking in front of him, since it had seemed like he was trying to stop the last time you were together, but mostly because you were fucking nervous.

“I brought this,” he said, revealing a bottle of wine that had been tucked under his arm.

You let him place it in your hands, looking at the label. You knew very little about wine, but you knew that this particular winery didn’t sell bottles for anything less than $500. “Thank you, this is like….really fucking expensive.”

“Oh? I don’t fucking know. The guy at the place said it was good, so…it probably s.”

“Come on in,” you said. “I just made dinner, if you’re hungry.”

Kendall followed you in. “Maybe in a little bit. Unless you are…”

Shaking your head, you crossed your arms in front of your chest and leaned back against the counter to look at him. Your stomach was just doing constant summersaults, twisting into itself. You didn’t want to eat either. And you were sort of frustrated with yourself for being so on edge, considering that the last time you’d been together he’d been fucking you raw. It had been awhile since you intentionally spent time with someone you actually liked.

Kendall watched you set the bottle down on your countertop, hands trembling. You weren’t easy to read but he had picked up on things over the years, here and there. It was rare, really, for you to show any type of anxiety, uneasiness. In fact, out of most of his employees, he could always rely on you to be composed. Of course, he wasn’t going to call it out and make things worse. There was, in the back of his brain, the very real concern that he was here just so you could tell him you regretted everything. In fact, he sort of wanted you to say it, so then he wouldn’t spoil you any further. Everything he touched got fucked.

Even knowing that, he still reached out, tentative.

“You look beautiful,” Kendall stepped closer to you, one of his arms sliding around your waist. Something about his touch made much of the nervousness dissipate. He leaned into kiss you very slowly, eyes searching for your own, all warmth and sadness before they closed, his lips slotting with yours.

Immediately you wanted more. Wanted him to hoist you up onto the counter, push your dress up over your hips and let him have you however he liked, frantic, desperate. All he had to do was kiss you, it was pathetic. But Kendall hadn’t been into that when you were last together. And maybe you needed to exercise some self-control and let him take off his shoes first, at the very least.

But he seemed different this time, his hands wandering, one of them gripping your ass, the other holding you tightly to his chest. Humming against his mouth, you let him lift your leg to hook over your thigh. His hips pressed forward, pinning you in between him and the counter, gave him space to run his hands underneath the skirt of the dress you’d worn, casual but nice enough for a date.

Two fingers hooked in the waistband of your thong, dragging it down. “Wow, so eager,” you teased.

“I can’t stop thinking about you,” his voice was lower than usual, husky, filled with want. The warmth of his breath hit your neck, fanned out, his tongue grazed over the spot where he’d bitten you, now a fading bruise.

“Me too,” you whimpered when he sucked down on the still tender area, like he still knew it still hurt but wanted you to feel it anyway. You didn’t know how he was so good at guessing what would turn you on, but maybe it made sense, deep down. He’d known you for long enough. Maybe he paid closer attention than you thought.

You rutted your hips against his, desperate for some kind of friction, something to help quell the arousal burning between your legs. Kendall steadied you, holding you back, away from him, and you whined in protest, until he spoke. “I’m gonna take care of you,” he murmured. “Don’t worry.”

And then he dropped to his knees, one hand on each of your hips. Looking you at you, he pressed his chin to your stomach, pulling you flush with him. And he stayed like that for a moment, watching your chest rise and fall, feeling the goosebumps that rose on your skin.

When he finally tore his gaze away, you knew what he was going to do, but that still didn’t prepare you for it. One of his hands lazily dragged down to hook on the soft underside of your knee, lifting it over his shoulder.

Kendall’s head turned to press a kiss against the inside of your thigh. And you were trembling, not from nerves anymore, it was anticipation. He was moving so slowly, smirking at every noise you made, every hitch in your breath. You made fists in the shoulders of his dress shirt, longing for purchase, even though it gave you very little.

And he was nipping, sucking, trailing his mouth lazily, moving closer to where you wanted him. “These dresses you wear…” he chuckled. “You make it so easy for me, don’t you?”

You nodded. Maybe you hadn’t imagined this exactly, but it was part of the reason you’d worn one. “Ken,” you sighed, softly, one final sweet plea before his mouth latched onto your clit. You were so wet already, he sunk two fingers into you with nearly no resistance, all at the same time.

Crying out, you reached behind you to brace yourself against the counter, clinging to anything you could just to keep yourself from collapsing. You’d never met a man so eager to go down on you, so fucking desperate for it. Kendall was fucking moaning into your cunt, the vibration making you shake even harder, even in his steady hands.

He found a rhythm that had your toes curling, sobbing out his name, and he didn’t relent. Not even bothering to offer any dirty talk like before, his mouth was otherwise occupied, and he seemed focused, diligent. You were going to last an embarrassing amount of time, having spent the better part of the week daydreaming about him. Curling his fingers perfectly, over and over again.

You came within minutes, too easily, overexcited, or maybe because he knew how to play you like a fucking instrument. Legs buckling beneath you, you squeezed your eyes shut as he let you ride your orgasm out on his mouth and fingers. And then he was standing again, wrapping you up in your arms.

“Kendall, you really didn’t have to-”

He cut you off with a kiss, tasting yourself on his lips. “Shh,” he pulled away. “Enough of that.”

“Wanna go to my room?” you asked, giggling in between sloppy presses of his lips. He was really horrible, really, in the best possible way.

“Sure,” he said, tugging at the loose end of the scarf in your hair, the one he’d bought you as a gift years ago. You never thought he’d notice you wearing it in this context, trailing behind you to your bedroom where you praying he’d fuck you within an inch of your life.

He was palming at the zipper of your dress as you stumbled over the threshold, you turned around to claw at the buttons on his shirt, a bit more confident this time around, and better at unbuttoning them. Before you’d been thrown into this world, very few of your previous flings ever wore button downs, besides on special occasions. They were a little frustrating.

The problem with Ken going down on you was that it seemed to only make things worse, as in – that it only made you more needy for him.

After you’d haphazardly managed to get each other out of your clothes, your back hit the bed, he stepped between your legs and you reached for his cock, hard between you both. His head tilted backwards, eyes closing as you worked him with your hand. You really, really wanted to suck him off but you were also feeling a little bit selfish, so you resisted the urge. In his brief moment of surrender, you watched him carefully in the dim light of the room, his cheeks all pink and flushed, the way his throat worked as he swallowed hard between gasps.

“You’re great, you know that?” you asked him softly, and his chin tilted down, eyes snapping open to look at you. You thought it might’ve made him smile, briefly, something to break the tension. Because he was, and you’d always thought so, even despite seeing his worst parts. But instead, his brows drew together and he shook his head, cupping your jaw with one hand and answering you with a bruising kiss. His teeth trapped your lower lip and he bit down, pulling back until you mewled at him. All of that to avoid just saying that he didn’t believe you. Like if he vocalized it, only then would you realize it, too.

“I want you on top, understand?” he asked, and you nodded, moving to let him join you on the bed, straddling his hips. He sat up, hands squeezing your breasts, pinching your nipples, as you kissed him again, moaning into his mouth.

You lowered yourself onto him, slowly, as he was still above average and not entirely easy to take all at once. But he was patient with you this time, pressing his lips down the column of your throat, down your chest, latching on one of your nipples, groaning at the feeling of you around him.

When you were fully seated on him, tentatively swaying your hips, feeling him deep in the pit of your stomach, he wrapped his arms around your waist.

“You’re so good,” Kendall cooed. “So fucking good for me.”

“Just for you,” you answered, voice a hoarse whisper, gazing down at him through half-lidded eyes as your hips rocked forward.

It felt nice to be so close to him, you’d always wanted to feel this, never imagining how good it might really be, or that you’d be able to do it at all, so you savored every moment. You knew that was the point of all of this, perhaps, but it went deeper than fucking for you.

Kendall felt the same, even though your self-doubt wouldn’t always let you believe such a thing, you knew it to be true just from the look in his eyes, his fingers tangling in your hair while you moved languidly, lips locking. He met each rise and fall of your hips, you felt him deeper than you ever had.

When you came, shuddering and sighing, gripping him tightly, he let out a gasp that sounded pained, and in one swift moment was somehow able to flip you both over pressing down into the cradle of your pelvis. He was on top of you again, pinning your hands over both of your heads. “Ken-” you sighed, still throbbing around him, inhaling sharply as he drew back, fucking into you, determined. After one particularly deep thrust he came undone, filling you up, your name on his lips along with a few choice expletives.

You really were too good, too sweet, too loyal for him, but he couldn’t help himself. He wanted you anyways, he was greedy. He liked that you wanted him back, it almost had him believing maybe he did do something right, somewhere along the way, even if he had a long way to go.

In the afterglow, he held you, tucked under his arm, head resting on his chest, still trying to steady your breathing as his fingers trailed down your arm. Your eyelids were heavy, he was so warm. There was something about him that felt so….safe. And that was wrong, probably. But it wasn’t like you could tell yourself not to feel that way.

“So uh, before we got distracted I did have something exciting I was meaning to tell you,” Kendall’s voice, still husky from lingering arousal, cut through the silence.

“Hmmm?” you asked, looking up at him, mind still hazy and blissed out. “What’s that?”

“I’ve been talking to Roman and Shiv, bouncing around ideas, and uh, we realized there’s still a chance to save the company if we can convince the shareholders that dad’s not acting in their best interest.”

You stared at Kendall a minute, processing the information, what this meant. When it registered, you raised your eyebrows, blinking once and shaking your head. “Okay.”

“What?” Kendall asked. “What’s that face?”

“Nothing,” you lied. “I’m thinking.”

“What’s there to think about?”

So many things. You jerked your head forward, widening your eyes in shock to answer his question. Your lawyer brain started up. “You really want to do this?”

“Yeah, you know, fucking, we’ve gotta start reaching out, talking to people. But uh, if we can pull this off, we can get the company back,” he explained. “And then, get everything back on track.”

“Ken,” you sighed. “I thought you didn’t want to be CEO anymore. I thought you wanted to cash out.”

“Uh-huh, well, if this doesn’t work out then maybe, I just-” he began, and you rolled off of him, onto your back, covering your face with your hands. He stopped talking, and you felt him shift to face you, one of his hands carding through your hair. “Hey, what’s wrong?”

“I’m trying not to argue with you right now….because you just made me feel really good,” you shook your head. Dread was pooling in the pit of your stomach. This. This was why all of this was a bad idea. “I should’ve fucking known. Fucking Stewy tried to warn me,” you muttered.

“Stewy, what do you mean?” Kendall asked. “Have you been talking to him?”

You shook your head again, rolling your eyes before turning to Kendall. “Yeah, I called him Tuesday about helping me find a job.”

“Alright, what the fuck? What’d you do that for?” he said, irritable. “I told you I’d take care of you. Also like, I’m gonna fucking need you when I do this.”

“Oh, you’re going to need me?” you asked, raising an eyebrow. “Great. I’m so glad I get a choice in the matter.”

“So what, you don’t want this?”

“No, I don’t. I think it’s a poor idea.”

“Nice, cool. Fuckin’ uh, glad to see you’re supportive-” Kendall moved, sitting upwards, making to leave the bed but you grabbed his wrist first. He’d taken you so off guard with this, but now your brain was working a little better.

“Hey, Ken, stay here a second,” you softened your tone slightly, realizing you were coming in awfully strong, forgetting everything that had been going on for him the past few months. Also you weren’t interested in chasing him down through your apartment so scantily clad. He did, looking over at you with a surprisingly bitchy look on his face, one you’d seen probably a thousand times before. “Just let me finish.”

He stared at you, expectant.

You took a deep breath. “First of all, you need to do some soul searching as to why you think any critique of an idea you have is a declaration of hate because that’s not what this is. It’s not…it’s not that it’s a bad idea, okay?” you rescinded your words from earlier, even though you still very much thought it was a bad idea.

“I just don’t want to see you get hurt again,” you continued, pausing to gather the rest of your thoughts. “It’s….it’s been really hard for me to watch over the past few years because I care about you.”

Kendall sighed, expression softening as he lowered himself back down slightly. You continued. “I think you’re so smart and capable, and maybe all that energy could go into something else.”

“Uh-huh,” he turned back to you. “But this means a lot to me.”

“I know it does, I get it,” you sympathized. “But I want you to be happy. And I don’t know if putting yourself through this again is going to help.”

Kendall’s mind was already made up, you already knew. You weren’t going to be able to change it. “I’ve still got to try. Not just for me, but for Shiv and Roman. I can’t leave them hanging.”

“I understand,” you nodded. And you did. He’d caught you so off guard, you weren’t prepared for a conversation like this. Didn’t have the tools to fight him on it without it blowing up. So you backed down.

“And, I do need you,” he said, after a long pause. “I was gonna fly to LA on Monday.” I was hoping you could come along. You’re so good with this stuff.”

You should say no. But you knew you couldn’t. Why couldn’t you?

“After, we can spend a couple days in Acapulco,” was leaning towards you now. “Just the two of us in a private cabana, a hot tub overlooking the ocean, a bed big enough we wouldn’t have to leave it…”

He pulled you closer to him, hand on your waist, slowly trailing down to grip at your ass, squeezing roughly. Your eyes closed and you sighed, too pliant under his influence. But you knew if you were going to do this, you had to draw a line. I mean hell, it had been important to you, when deciding if you wanted to follow through with whatever the fuck this was between you both – that he was your former boss. Not your current one. And if you were back under his wing, well, that changed everything.

“Kendall that sounds lovely,” you said. Because it did. “But uh, if we’re going to be working together maybe this-” you gestured between the two of you. “Isn’t a good idea.”

“Why not?”

You scoffed. “Uh….so many reasons? Morally, ethically, spiritually. Obviously, it’s an HR nightmare, and a huge potential scandal. And just…you know…boundaries. Like, we’re talking about work right now and I’m in bed with you. That’s not fun. I don’t want to do that.”

Kendall pursed his lips together, confidence in his eyes that rarely surfaced, and you liked, but in this situation found annoying. “Uh-huh well, I think you should reconsider.”

“Okay,” And if he was getting to play this game, then so were you. Because if you took it in any other direction you’d end up arguing. You paused for a minute, furrowing your brows and looking around the room, pretending to be deep in thought, before focusing back on him and nodding. “Yeah, I just did, and I still think it’s a bad idea.”

“Well, I shouldn’t be here, then.” Kendall sighed, removing his hands from you, which was unfortunate, and you realized, you did not want. At least not now. You didn’t want him to leave you like this. In a salty kind of way.

“Wait Kendall-” you hooked your leg over his hip, dragging him back towards you.“This doesn’t change that I like you. You can’t leave yet. I just need some time to think it over. We should enjoy tonight, at the very least.”

He glanced back at you, unamused. “Plus, you haven’t even had dinner yet, and, not to brag or anything, but I am a culinary school dropout.”

“Oh wow, you’re so impressive,” he said sarcastically, and then added after a moment, fondly. “I didn’t know that about you.”

“It was a long time ago,” you explained, climbing on top of him, knees on either side of his waist, you pressed your palms against his chest. He tried to look irritated, but the facade slipped when you tilted your head, running your finger down the bridge of his nose, over his lips, before giving him a cheeky grin. He wasn’t going to change the subject, distract you from getting what you wanted. “Please?”

He looked at you, the affection in his eyes betraying him before he could even give his answer. “Okay.”

Part IV