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I Can See You - Chapter 3

Kendall Roy Masterlist

Pairing: Secret Office Romance Kendall Roy x Fem Reader

Word Count: 9k

Chapter Summary: You and Kendall (unsuccessfully) attempt to adapt to your strictly professional relationship

Warnings: Age gap (reader in her 20s, Kendall is 39), swearing, brief mention of sexual assault (waystar cruise scandal), comfort, light smut (making out, grinding)

A/N: Apologies for the long wait!!! Had a lot of ground to cover with this chapter lmao, hope you guys enjoy it! Will do my best to have chapter 4 out sooner :)

Chapter Theme Song: Fire For You by Cannons

*No use of Y/N

“Hey, looking forward to working with you as well. Enjoy England!”

Kendall sits alone at the back of the Roy jet, baseball cap pulled low over his forehead as he stares at your text. He’s looked at it so many times over the last few days that he thinks there may be a permanent imprint of it etched behind his eyes.

He rereads it again, wishing your exclamation point had been assigned to the first sentence rather than the second. That’s what you should be more excited about - working in close proximity with him every day, not him having a horrific few days on the other side of an ocean.

Obviously he knows you aren’t aware of what this trip was for him. No one would guess that a few days in England with his family would make for one of the most miserable weeks of his life, or that he would board this plane feeling more alone and hopeless than he ever has before. The trip coming to an end is alleviating, but only partly. The shame he carries with him about the night of his sister’s wedding, the heaving guilt that is constantly sitting in the middle of his chest, has grown exponentially since he left New York. Seeing the dead kid’s house, meeting his family, being unable to confide in anyone, not even his own mother, about it… it’s bleak. It’s so fucking bleak and he’s now convinced that he will be living with this level of anguish for the rest of his life. It’s the loneliest feeling in the world.

The pilot announces that they’ve begun their descent into New York. Kendall locks his phone, the bright light from your text disappearing to black. It’s still there though, right behind his eyes.

————————————

Your week goes relatively smoothly, considering how it began. You and Jess finish your training by Tuesday afternoon, and the rest of the week is spent mostly just preparing you to fully enter the Waystar world. You meet a few other important executives, as well as their assistants, and you’re pleased to find out that you are definitely not the least qualified in the bunch. One assistant, Greg, who Jess tells you is actually a Roy cousin, stumbles awkwardly through your short interaction with him, using words he clearly doesn’t know the meanings of multiple times. He reminds you a bit of a newborn giraffe in terms of physical build, grace, and intelligence. If he can survive in this world, then you definitely can.

When Friday rolls around, you’re surprised to realize that you actually feel pretty good about your future at Waystar. You understand your tasks, are getting used to the routine, and no longer feel overly intimidated by the workplace. All that’s left to do now is learn how to maintain a professional working relationship with a man who has seen, touched, and been inside your naked body. Ugh. You have until Monday to deal with that though, a full two days to relax and reset before the real work begins. No need to stress yourself out about it too much yet.

It’s almost 7pm when Jess tells you you’re good to head out for the weekend. “9-5 isn’t really a thing at Waystar, especially when you’re an assistant,” she explained on Monday, so she’s been dismissing you later and later every night this week to prepare you for what’s to come. For now, you don’t mind too much. It’s not like you have any friends to make plans with or any money to do anything exciting with. The extra one or two hours are usually just spent at your desk while you and Jess exchange life stories, so you enjoy the opportunity to socialize. You can definitely see it becoming a frustrating expectation in the future, but you’ll cross that bridge when you get to it.

You grab your jacket and bag from your desk as you prepare to head home, the knowledge that you won’t be back here tomorrow giving you a lightweight, relaxed feeling. After saying goodnight to Jess, you head toward reception and push the call button for the elevator. The office is quiet, but not as quiet as you would expect it to be at 7pm on a Friday night.

‘This is part of why the Roys are billionaires,’ you think to yourself. ‘Running themselves and everyone around them into the ground.’

As if conjured by your insubordinate thoughts, the elevator doors open, and you’re suddenly face to face with Kendall and a man you’ve only seen in the many Waystar training videos you’ve watched this week - Logan Roy.

You take an automatic step back to give them space to exit the elevator, clutching your jacket close to your chest as if to protect your core from an enemy attack. You and Kendall stare at each other for a second, both of you looking like deer in headlights. He was clearly not expecting you to be at the office this late, and you were not expecting him to be back in New York this early. The surprise appearances the two of you keep making are never ending.

Kendall clears his throat as his dad exits the elevator first. Logan doesn’t even look your way until Kendall speaks and gestures to you.

“Uh, Dad, this is one of our new hires. She’s just started working under Jess as an administrative assistant.”

Logan stops and gives an uninterested “oh” as he turns to you and extends his hand for you to shake. You return the gesture and introduce yourself, telling him what a pleasure it is to meet him and work for Waystar.

“Good to have you aboard,” he nods.

You’re not sure where it comes from, maybe your lifelong need to be liked, but the urge to say nice things that you don’t actually believe suddenly takes over.

“Thank you. Really, it’s an honour to work for such a longstanding company. I’ve always admired Waystar’s consistency; how you’ve been able to maintain such a steady brand presence and image for decades is beyond impressive.”

Your praise has piqued Logan’s interest ever so slightly. “Glad you see it that way,” he remarks approvingly. “Consistency is what keeps our customers loyal, it’s crucial to our success.”

You nod. “I completely agree, and your track record in earning the consumers’ trust and then keeping them loyal… it’s very admirable.”

“Well, thank you,” Logan responds. “Hopefully you'll contribute to maintaining that consistency during your time here.”

“Absolutely, any way I can. Maybe I’ll have to adopt my own Waystar uniform or something so I can get into the right mindset.” You give him a sweet smile with your joke, internally hating yourself for being such a kiss-ass.

To your surprise, Logan emits a light chuckle and gives your arm a grandfatherly pat. “Good attitude,” he smiles, “that’s what we need around here.”

Your smile grows at his reaction. You may be a kiss-ass, but this feeling of relief, knowing you managed to not completely fuck up this interaction, makes it worth it. You suddenly remember that Kendall is also present and your eyes quickly flash to him, hoping you’ll be able to see what he thinks of your conversation with his dad.

Though you may have forgotten he was there for a moment, but you’re painfully aware of it now. His gaze is fixated on you, and he doesn’t look impressed. He looks… you’re not sure there’s an exact word for it, but the closest one that comes to mind is mystified. Not like he’s fascinated by you, but more like he’s looking at a math problem that he can’t seem to figure out. Intense concentration mixed with deep confusion and a sprinkle of frustration.

You’re suddenly desperate to end the conversation. “Well I won’t take up any more of your time Mr. Roy, but it was a pleasure to meet you.”

He gives you a nod and another pat on the arm. “You too,” he says, and then he begins to walk away. Your gaze flashes back to Kendall, whose expression hasn’t changed from the last time you looked at him. He stands there for a second, watching you as you press the elevator call button again and not saying anything when you finally look up and hold his eye contact. His brows are slightly furrowed and you think he’s bound to make some type of comment, but he doesn’t. He just walks away, following his dad deeper into the office and leaving you to stare after him.

The elevator dings behind you as it arrives, snapping you back to attention. You stumble inside, fidgeting anxiously with the buttons of your jacket as the doors close and you begin your speedy descent to the ground. You no longer feel like you have all weekend to relax, you know you’re going to spend the next two days doing nothing but replaying that short conversation over and over again in your head. What did you do to warrant that kind of reaction from Kendall?

Your commute is always cramped and tedious, but it feels 10x busier and longer today. You spend the entire subway ride with your headphones in your ears but nothing playing, which you don’t even notice until you get off at your stop - your mind has been making enough noise on its own. Eventually you reach your street and start to feel like you might be able to relax; you just need some food and TV to distract your brain. Just as you’re approaching your building’s front door though, your phone buzzes in your pocket. You pull it out and your heart stops.

Kendall Roy

2 Text Messages

You freeze in your tracks, your fingers rushing to unlock your phone. You don’t want to give yourself time to theorize what his messages might be about so you open them immediately.

“Have to say, that was both impressive and unsettling to watch.

You didn’t fuck him too did you?”

A shocked laugh escapes your mouth. Definitely not what you were expecting to read. You begin typing a response as you push the front door of your building open with your shoulder.

“Lol no, but you should still be worried. Clearly I’m naturally gifted at winning over members of the Roy family.”

You hit send before you can overthink it. His second text was the furthest thing from professional, so there should be no issue with you playing into the banter that he started.

Your phone buzzes again before you’ve even entered your apartment.

“Oh I am, anyone who can tame a Roy needs to be taken seriously.

Gotta keep an eye on you before you charm your way into my job next.”

You pull your jacket off and then toss your bag onto the couch, flopping down beside it as you smile at your phone.

“I was thinking of just taking your company shares actually. I’ll let you keep the COO title and office, it’s the least I can do.”

You know that texting like this is dangerous. It gives you and Kendall the opportunity to continue developing a personal relationship when you should be solely focused on your professional relationship. But… fuck, you really like him. You two click so seamlessly; talking to him, joking around with him, being intimate with him… it all comes naturally. If you’re going to be in each other’s lives and can’t do the physical intimacy part, you should at least get to have a little bit of emotional intimacy. It wouldn’t make sense to completely deprive yourselves of your connection, right?

That’s what you tell yourself when your Friday night texts to Kendall turn into Saturday morning ones, and then into a conversation that continues until the end of the weekend. The banter is still present, but your messages to each other also take on a more sincere tone. Kendall is almost always working in some capacity so his texts arrive irregularly, but when he does respond, he surprises you by actually seeming interested in how you’re spending your weekend. You give him little updates of your adventures around the different Manhattan neighbourhoods, and he makes jokes about you being a lame tourist, but he also wants to know your opinion of his city and what you’ve been most interested in seeing. The urge to make a “you should show me around” comment feels impossible to resist, but you manage to hold your tongue. It would be hard to pretend that your text conversations have been completely innocent after making a suggestion like that.

When Monday arrives, you actually find yourself excited to be fully working with Kendall rather than nervous. Continuing to flirtatiously tease each other at work is obviously out of the question (especially when everyone thinks you’ve only interacted once for less than 10 minutes), but you’re just happy you get to be around him. Your text conversations this weekend have fully cemented your fondness for him. His wit, his intelligence, his perceptiveness, you love it all, and the more you learn about him, the more you want to continue learning. It’s a dangerous realization to come to, but you tell yourself that it’s not a big deal. As long as Kendall stays professional, you can too.

You get to the office early, and Jess is, of course, already there (you’ve learned that you can show up as early as you want, but Jess will still be there first). You begin the day by reviewing Kendall’s general schedule for the week together, and you’re surprised to learn that he’s going to be crossing the pond again, but this time to go to Scotland for an event being held in his Dad’s honour. God, is he ever actually here?

Today, he is. He shows up a little after 9, wearing the stern expression that you’re still getting used to. The confident smile that crinkles his eyes, the smile that initially attracted you to him, is hard to picture when you watch him in his natural habitat. He gives you and Jess a neutral greeting as he strides into his office, and you begin to understand why one of your first impressions of him was that he belonged in any room he entered. It’s probably hard to not feel that way when you’re the prince of an empire and can see the effect your presence has on others. Everyone in the room sits up straighter when Kendall walks by, and you notice yourself do it too. The last thing you want him to think is that you aren’t taking this job seriously, so you remind yourself to always look like you’re hard at work.

Kendall has a meeting with some of the other top executives shortly after arriving, but it’s not long until he’s back in his office and calling you and Jess in.

“So let’s uh, go over the week,” he says, looking down at the paperwork on his desk as you and Jess sit down opposite him. “And then Jess, I want to make some changes to the script for that… recording studio bullshit I have to do for the uh, Dundee thing.” He looks up at her at this point, but his eyes haven’t travelled in your direction even once.

“For sure,” Jess nods before turning to you. “Why don’t you take it away with the main points for the week.”

“Oh yeah, um, sure,” you say as you shuffle through your documents and then begin to summarise the central tasks Kendall has this week. Board meetings, lunches with shareholders, calls with Scottish reporters about Logan’s upcoming Dundee celebration, his expected attendance at the preview for a play that his brother Connor is financing, etc. Once you get through all the boring stuff, Jess fills him in on the more nuanced and personal information he needs to know, which includes mentioning the ridiculously long email that Connor sent about Kendall’s ‘enthusiastic presence at the preview being of the utmost importance in order to set the tone for the play’s run.’ Kendall sighs.

“Jesus fuckin’ Christ,” he mutters, shaking his head slightly. He looks up at Jess - he hasn’t made eye contact with you even once yet. “Could you get him off my back somehow, like, I don’t fuckin’ know…” he trails off, thinking of what it’ll take to get Connor to shut up.

You jump in. “We already arranged for the playwright - Willa?” You look over at Jess to confirm the name, and she nods. “To receive a bouquet from you the night before the preview, but we could include the entire cast if you’d like? Make it a bigger gesture?”

Kendall finally locks eyes with you. “Oh, yeah, that’s, uh… that’s good, go ahead with that. Please,” he adds before looking back the pile of documents on his desk. “Is that everything?” he asks as he looks up at Jess, his eyes briefly flashing in your direction.

“Yep,” she nods. “Do you want to start making those changes to your script now?”

With your role in the meeting being complete, you gather your things and leave Kendall’s office, settling back in at your desk on the other side of the glass wall.

————————————

Jess pulls out a physical copy of the script she’s workshopped for Kendall. Her draft is good, but Kendall knows it needs to be more explicitly complimentary toward his father. Gotta do whatever it takes to keep him happy.

“So, what were you thinking of adjusting?” she asks as she scans the page, placing it on his desk between them.

“Oh um, something about him always being there for me, or…” he trails off, his mind elsewhere. “Uh, was it your idea to send flowers to Willa?” He can’t concentrate until he’s confirmed something for himself.

Jess looks up from the page and shakes her head, explaining that you had taken the initiative to write a response to Connor saying how excited Kendall was to attend the preview, and then arranged for a bouquet to be sent to Willa. All Jess had done was given you the go-ahead to send the already-written email, and her permission to order the flowers.

“Right,” he responds, “right, okay, thanks,” and then he directs his attention back to the script in front of him. He can feel Jess looking at him questioningly for a moment, and he knows that what he just did was suspicious as fuck. At Waystar, it really doesn’t matter who had an idea first, it only matters that bad ideas are rejected and good ideas are implemented. Confirming who suggested the (pretty basic) plan to quiet Connor’s cry for attention is not even remotely important, and Jess knows that. Kendall just couldn’t stop himself from hearing more about how you operate. How you took control of the Connor situation, the way you sweet-talked his dad, the fact that, so far, you’ve been more than capable of acting like you and Kendall never spent a night together… it’s bizarre.

“Let’s uh, fuck it, let’s put in something about my dad being there for my, uh… many ups and downs or whatever,” Kendall suggests, hoping to distract Jess from his unusual behaviour. She nods and searches the page for a suitable place to make the addition, and Kendall allows himself a second to look over at your desk. Unfortunately, Jess looks up at him before his gaze leaves you.

————————————

Your week speeds by. Kendall isn’t always in the Waystar building, but the quality of your day multiplies when he is - not just because you like being around him, but also because when you are, you can see that he’s just as aware of your presence as you are of his. You sometimes catch him sneaking glances at you from his office, and he comes out to your desks semi-regularly to make requests of Jess that definitely could’ve been done over the intercom. One day, when you’re settling back in at your desk after making a cup of tea in the kitchen, Kendall gets back to his office from a meeting and notices your drink.

“Those aren’t cheap, you know,” he comments as he walks by your desk. “Teabags are, what, like 3 fuckin’ dollars now? If you’re gonna have multiple every day, we’re gonna have to start taking that out of your pay cheque.” He smirks at you, and you can’t believe he’s actually doing this while Jess is sitting directly across from you. You haven’t seen him ever joke around with her, is this not noticeably out of character for him?

You try to react like a new assistant would with a boss she doesn’t want to disrespect - politely engaged. You laugh lightly (very lightly, can’t have Jess thinking you’re flirting) and smile. “I think it’s more like 20 cents, but okay, I understand, gotta do what you gotta do to keep this place running.” You shrug good-naturedly (“Nothing to see here Jess! Just being agreeable with the boss!”) and turn back to your work. You think you’ve hidden your connection with Kendall pretty well until Friday night rolls around. You’re just about to head out when Jess calls you over.

“Hey, sorry, can you hang back for a minute?” she asks.

“Uh yeah, of course. What’s up?” You settle back into your chair opposite her, resting your jacket and bag on your lap.

Jess leans forward on her desk and glances around. The office is relatively empty, and no one is seated near the two of you. Deciding that it’s safe to talk, she turns back to face you.

“Well, you’ve been here for 2 weeks, I just wanted to see how you’re feeling about everything so far.”

“Oh, um…” The way she asks the question catches you slightly off guard; this is definitely not a formal performance review, it feels much more like a personal check in. “Really good, actually. Everyone is pretty nice, I think I’m handling my tasks well… yeah, I’m feeling good about it all.” You nod to indicate that you’re done speaking, but she looks skeptical.

“… So everything’s totally okay?” she asks. Again, this doesn’t feel like official Waystar business, and she isn’t presenting the question in an accusatory manner, she seems… concerned.

Your eyebrows knit together in confusion. “Yes, everything’s totally okay,” you nod. “Why?”

She leans forward a little further. “I’ve just… I’ve noticed that Kendall’s been paying… extra attention to you.”

Your heart drops. Fuck. Does she know? Fuck fuck fuck fuck fuck.

“Like I said on your first day, he’s a good guy but he can be a bit, um, unsteady at times, and you know, he’s been a billionaire pretty much his entire life so he isn’t always conscious of the kind of power he holds…” She raises her eyebrows at you as if to hint at what she’s trying to say, but you don’t want to give any indication that you know exactly what she’s been noticing. You give her your best confused expression instead. “I just mean… you can tell me if you ever feel uncomfortable. Sometimes he just isn’t aware that he’s crossed a line that normal people wouldn’t.”

You pretend to finally realize what she’s suggesting. “Oh! Oh no, I haven’t felt uncomfortable at all.” Thinking on your feet, you come up with a valid reason for Kendall’s heightened attention around you. “I just mentioned to him, when he was showing me the copier room on my first day, that I was a little nervous to work here, which was probably a stupid thing to mention to my new boss during our first conversation, but I think after hearing that he’s just been more conscious about me, like, fitting in and being comfortable at the company, so he’s been paying closer attention.” You realize that you’re rambling and hope she assumes it’s because you feel bad that Kendall’s being wrongly accused of harassment. “So no, I haven’t felt uncomfortable at all, but I really appreciate you looking out for me.” You give her a smile of gratitude and she smiles back, seemingly satisfied with your explanation. You breathe an internal sigh of relief.

“Oh, okay good. You’re doing really well so far, I just wanted to make sure that everything else was okay too.” She smiles again and emits a breathy “whew” sound. “Cool, I feel better now. Sorry to keep you behind longer, please, go have a good weekend.”

“Thanks Jess, you too. I’ll see you on Monday.” You give her a little wave and try to stay composed as you make your way to reception while your mind screams at you. Having to act like you’re not freaking out in the elevator as it stops at multiple floors on its way to the ground is a cruel test of self-control, but you eventually make it out. The fresh air that hits your face when you finally exit the Waystar building helps you settle down a little, but not enough to completely erase your sense of urgency. You don’t hesitate in pulling your phone out to message Kendall.

Though you haven’t been texting each other as consistently as you did this past weekend, you haven’t exactly been ignoring each other either. Your conversations are generally innocent, usually just teasing jokes that you can’t make in the office without seeming too friendly (comments a little more intimate than pointing out your excessive tea consumption), but it’s now clear that you weren’t hiding your friendship as well as you thought. You rush to compose a warning text for him.

“Jess commented on you paying “extra attention” to me. We need to tone it down.”

You quickly hit send before re-reading the text. It’s not until it’s already been delivered that you realize that you didn’t mention anything about covering for him, or that she doesn’t seem to be suspicious anymore. It’s no surprise when you receive an incoming call from Kendall not even 20 seconds later.

“It’s okay, I handled it,” you say the second you pick up. You explain your lie about ‘confessing your nerves’ to him in the copy room on your first day, and that what Jess has noticed is just him keeping an eye on you. “She seemed to believe it, so if she asks, just pretend like you’ve become an empathetic person overnight.” You can’t stop yourself from adding in that little dig at the end, it comes too naturally with Kendall.

“Hey, I’ve got the empathy of fuckin’ Gandhi,” he quips. “I let you keep your job, didn’t I?”

You scoff. “For your ego’s sake, I’m gonna let you pretend that I didn’t have you backed into a corner. But seriously,” you add, your voice taking on a more serious tone. “Maybe we need to… take a step back from talking for a bit? Just until we can be friendly with each other less noticeably?”

Your heart aches for itself. Talking to Kendall, joking with Kendall, flirting with Kendall… You’re ashamed to admit that your interactions with him, whether by text or in person, have been the clear highlights of the week. Your conversation with Jess is a rude awakening though, and you think it’s maybe time for you to focus your attention on someone other than your boss.

Kendall is silent on the other end for a few seconds. “Uh, yeah. Yeah, okay. I’ll, fuckin’, uh, I’ll just see you when I get back from Scotland then.”

You want to take it back, you want him to resist, but unfortunately, neither of you does what you want.

“Okay, yeah, I’ll see you next week. Have a good trip and uh, enjoy the play tonight.” Kendall just responds with ‘yeah, thanks,’ and hangs up. You stare at the black screen for a moment, angry with yourself for getting into such a stupidly risky situation in the first place. You allow yourself a few seconds of self pity before you unlock your phone, open the app store, and download Hinge.

————————————

Kendall hangs up and stares out the window of his chauffeured car’s backseat. He’s a few minutes away from the theatre where Willa is holding her play’s preview, and if he didn’t want to go before, he definitely doesn’t want to go now.

The disappoint he feels is frustrating. You aren’t dating, you aren’t fucking, he can’t even really say you’re friends because you don’t hang out with each other outside of work. He’s not really losing much by not being able to text you anymore, so why is this so disappointing? He chalks it up to you being the one to suggest taking a step back. His marriage to Rava aside, it’s very rare that he’s not the one to end things (not that this was even a relationship to begin with, he reminds himself again). He’s just frustrated because his assistant was the one to say that they shouldn’t text anymore, that’s it. He just needs to find a new person to focus on, someone who he can feel a bit more in control with.

The car pulls up to the theatre. He opens the door and steps out, ready to be Kendall Roy.

***

Willa’s play is shit of course, but one aspect of it manages to hold his attention. An actress - this pretty woman with short brown hair - catches his eye and keeps it for the entire show. He practically beelines his way to her at the after party and doesn’t hesitate to turn the cockiness and charm up to 1000%. She’s cute and bubbly, he’s definitely attracted to her, and she seems to be attracted to him (or his money, name, whatever), so he takes her home that night. The sex is really good, but for some reason the entire thing feels… off. Something about her isn’t clicking for him, but being alone isn’t really an option for him right now; he can’t just not have someone else to focus on after his call with you. He throws himself completely into this fling in hopes that eventually, he’ll start to like her more.

He does it all. He love-bombs her, he invites her to Dundee, he holes up with her in their lavish hotel room, he shows her off to his family, but none of it works. What is he missing? He’s back in the swing of things, getting his ego stroked and his dick wet, she’s hot, and he gets to play the role of the swaggering billionaire who exists in a perpetual state of unshakable confidence; it’s all the things he usually finds some semblance of pleasure in, but not this time - this feels so much more vacant than usual. It’s infuriating, why is this being taken from him as well?

He finds himself growing increasingly frustrated with her for not properly fulfilling her purpose of being an easy distraction, but he knows that his anger is misplaced. It’s not her that’s ruined this for him, it’s you.

Her interaction with his dad is the nail in the coffin. Having his father’s approval is the single most important thing to him, and with her on his arm, he can kiss whatever respect Logan may still have for him goodbye. Even if, like you, she had aced her conversation with his father, he doubts it would’ve mattered. He knows why it feels empty; he hasn’t actually earned her affections like he did yours, and he doesn’t really care to. Whether she knows the real him or not doesn’t matter, because this thing with her doesn’t fucking matter. He sends her back home early and wonders how much more depressing his life can get.

————————————

Your Monday morning starts the same way it normally does. You get to work early and Jess is already there, ready to review the day ahead with you. Her behaviour this morning is a little more serious than you’ve seen before though.

“So there’s been some developments with the Brightstar incident…” she starts, and you can tell she’s already exhausted. “A whistleblower came forward, and he’s provided concrete details about what happened in cruises, and how it was all covered up. There’s going to be a federal hearing and Kendall will be testifying, so we…” she sighs. “We’re gonna have our work cut out for us this week.”

As you two get down to business, it becomes clear that it’s really just Jess who has her work cut out for her. She’ll be joining Kendall in Washington and working with him and the rest of the executive team to form a strategic plan for his testimony. Your week won’t be much different from the last two. You’ll be staying in New York, holding down the fort, and rescheduling every single one of Kendall’s obligations for the near future.

For you, this couldn’t have worked out any better. You’re only in your third week, so not having to learn anything new or dive into the dirty side of the corporate world is ideal when you’re still getting comfortable in the role. It also means that Kendall will be gone for at least a few days, which will make this transition of not speaking to him slightly easier. Out of sight, out of mind, right?

For Kendall, you’re concerned. Why exactly is he being called to testify? Because he’s the son of the CEO? Or because he played some part in this? Jess doesn’t give you many details about what this means for him, and you don’t press her for any. You’re not sure you want to know how involved he was with the cover up; you want to believe the best of Kendall, and if you learn that he was complicit in this kind of shit… the thought of it makes you feel sick.

Kendall and Jess leave for DC the next day, and you continue on with your week as scheduled. It’s weird being the only one there. You aren’t completely alone in the giant Waystar offices obviously, but without Jess and Kendall there, you’re pretty much just working by yourself and not answering to anyone. For this reason, you don’t hesitate to pull up the livestream for the congressional hearing on the day that Kendall is set to testify.

Tom Wambsgans is called first. You learned from Jess recently that he’s actually Kendall’s brother-in-law, and his assistant is Greg, the Roy cousin you met last week. Tom absolutely butchers his testimony in a way that gives you the worst possible second-hand embarrassment. ‘Good god,’ you think to yourself, ‘this company really is just a shitpile of nepotism.’

Kendall and Logan are next. He sits next to his father with a stern look on his face. It’s the look that has completely replaced the crinkly smile you initially associated him with. You miss it.

Logan begins his testimony by attempting to gently brush aside the accusations, but when that doesn’t work, he doesn’t hesitate to throw Kendall under the bus. Your heart rate skyrockets as it becomes clear that Kendall is now the main target. Fuck, the last thing you want to do right now is watch what happened with Tom happen to Kendall. The senator questioning him seems ready to play hardball, and though you suspect that Kendall might be capable of striking back, watching him actually do it is hypnotic.

No stutters, no swearing, no filler words. He uses ‘sir’ and speaks respectfully while also turning every accusation back on the senator. The way he commands the room with his testimony is mesmerising, and as you watch him control the situation, you feel something change - a different type of attraction to Kendall is rooting itself inside you, and you don’t attempt to stop it. Since the day you met him, you’ve thought he was handsome, smart, funny, sexy, all that good stuff, but right now… god, this is a side of him that you hadn’t fully seen yet and you need to see more. You want him to aggressively push you up against a wall before he has his way with you. You want him on top of you, talking you through it while he brings you over the edge. You want him to lay claim over you, to tell you that you’re his and only his. You feel your heart rate pick up again.

His testimony ends and you close the browser. Fuck. You shouldn’t have watched this. It’s the furthest thing from ‘out of sight out of mind’ you could’ve done. You’re brain is swimming with thoughts of Kendall. Kendall kissing you, Kendall touching you, Kendall fucking you. And now, you have to get ready for a date with someone else.

This week seemed like the perfect time to do it - waste no time and put yourself out there while Kendall isn’t around. You started matching with people on Hinge and eventually connected with someone you could see yourself having some fun with. He asked you out for drinks tonight, and you were originally planning on going home after work to change and get ready, but you don’t give a shit anymore. He’s not Kendall. It doesn’t matter.

You dump the contents of your bag out onto your desk. A tube of chapstick and some blotting papers are the only beauty products you have with you. Sighing, you dab at your face with the blotting papers and apply the chapstick. You’ll quickly fix your hair in the bathroom before you leave, but unfortunately, that’s all the prep this Hinge guy is going to get from you today.

You hang around the office relatively late. Your date is at 8pm, so it isn’t until 7:30 that you finally stop spinning from side to side in your desk chair and leave the building. When you arrive at the bar and meet your date, you immediately feel guilty. He’s good looking, he’s well dressed, he seems excited to be on this date with you, and you couldn’t care less about him. You could be on a date with the man of your dreams right now and it wouldn’t matter because he’s not Kendall. “Hit us as hard as you can, we can take it. We have nothing to hide,” in Kendall’s deep, assertive voice replays in your head over and over, and no matter how hard you try, you can’t get excited about the man sitting in front of you.

You’re able to make it through 2 hours before you just can’t pretend to enjoy the date anymore. He offers to walk you home, but you don’t accept. He doesn’t pressure you, just tells you that he had a good time and he hopes you get home safe. You end the date with a hug before going your separate ways, and you know that you will never see that man again.

The journey home is a daze filled with negative self talk. Your mind is stuck on the only man in the city that you can’t have, and when a perfectly good alternative is presented to you, you can’t do anything except think about Kendall. God, you’re a fucking mess.

It gets worse when you finally return home. You begin digging through your bag for your apartment keys, ready to just crawl into bed and sleep this day away, but they’re nowhere to be seen. You check the pockets of your bag, your pants, your jacket, but they aren’t there. Your mind races, wondering where you could’ve left them when you remember dumping your bag out onto your desk.

“Are you fucking kidding me,” you swear under your breath. It’s almost midnight on a Friday night, there’s no way in hell that your geriatric landlord is going to be around to let you into your apartment. You have to go back to work.

You feel numb as your climb into the Uber you order and are shuttled back to work. Forgetting your keys further confirms for you what a mess you are. When you arrive at the office, you speak to the security guard in the lobby. After showing him your ID card and explaining your situation, and he lets you take the elevator up. You plan on getting out of there as quickly as possible, but that changes when you approach your desk and notice that a lamp in Kendall’s office is on.

And then, you notice Kendall.

He’s on the couch on the far side of his office, scrolling on his phone while he roughly rubs the back of his neck. Your task of retrieving your keys vanishes completely from your mind, and you approach his office door, knocking softly. His head snaps up at the sound, but his expression relaxes when he see’s it’s you.

“Hey,” you say gently as you push the glass door open. “You’re back already.”

He rises from the couch. “Uh, yeah… benefits of a private jet.” He gives a half-hearted smile and gestures for you to come in. “I uh, yeah, I didn’t want to stay in that, fuckin’, political hell hole any longer than I needed to.”

“Understandable,” you say as you close the glass door behind you. He’s standing near the window now, arms crossed, and you stand opposite him awkwardly, unsure if it would be weird to sit and make yourself comfortable. His eyes flash over to the couch.

“Sorry, I’m fuckin’ exhausted, can we sit please?”

Though all you want right now is to be in your own bed, the expensive couch in Kendall’s office is an acceptable placeholder, especially when staying here also means you get to be in his company. You nod and sit down, and he joins you, keeping a good amount of space between the two of you.

“So… how do you feel?” you ask after a moment, your head turning in his direction.

“Oh, um, yeah. Initially, I felt pretty good,” he says. His legs are spread apart and he’s leaning forward, elbows resting on his thighs as he clasps his hands together in the empty space. You notice his long fingers, the veins protruding across the back of his hands, the defined tendons stretched across the skin. You never paid much attention to his hands before, but now, all you can think about is how much you want to hold them, want them on you, want his fingers in you. Fuck, you really shouldn’t have watched that livestream. “You know, everyone was telling me it went well, but, uh… someone still needs to go down for it. I just… I have this shitty fucking feeling that it’s gonna be me.”

There’s no trace of anxiety, or anger, or sadness in his tone. He sounds so removed from the situation, almost apathetic toward it. You’re desperate to find out if that’s for the reason you fear.

“Kendall, I have to ask,” you say slowly. “Did you… know? Anything about it?”

You don’t dare look at him after asking something like that, your eyes stay glued to your feet. He sighs, and you feel him sit up beside you. “I know it’s hard to believe but, no. I didn’t.” He pauses for a moment before he continues. “It’s… it’s kind of an unspoken rule that the nasty stuff shouldn’t reach my desk. The executives who report to me, they eat a lot of shit for me so that I don’t have to. Keeping upper level management out of it gives us plausible deniability… protects the company.”

You nod. It’s a relief that he wasn’t the one covering up the horrors that happened on those cruises, and you can now assume that his apathy toward the entire thing is a coping method - detaching himself from the feeling that he’s going to take the blame for everything is probably the only thing keeping him together.

He’s looking over at you now, and your concerned expression must be telling him a different story. “I know, just because I wasn’t fully aware of the details doesn’t make it okay. It’s fucking awful. But, I uh, I think I’ll be the one taking the fall for it anyways, so there’s my fucking karma.” He sighs again.

You shake your head slightly. That’s not at all the impression the hearing left you with. “I don’t know Kendall… I was watching and you… you did really well,” you offer. “I know I’m not a corporate strategist or anything, but from the perspective of an average citizen, you um…” you pause, wondering how to properly word this. “You seemed powerful.”

Kendall gives a small, slightly bitter laugh as he leans forward on the couch again. He hangs his head down and begins to roughly run his hands up and down his face. “Yeah, that’s uh, probably not the best impression to make when they want a top executive’s head on a fucking stick.”

You instinctively turn your body toward him and reach your hand out. It lands on his shoulder and you feel him freeze under your touch, but he doesn’t move away. “No, but not powerful in the sense that people will want to overthrow you, powerful in a way that seemed… warranted. Like… you controlled your responses so masterfully, no one could watch how you handled that situation and think that your power was just given to you by default or achieved through brutality.”

There’s no need to expand on this point - he knows you’re referring to Tom and his dad, and you wouldn’t dare to make any explicitly negative comments about either of them. You can see that the Roy family has a fucked up dynamic, but they also seem close. You need to focus not on what they did wrong, but on what he did right. “You presented yourself as someone who deserves their position, and Americans love it when people earn their privilege. I really can’t see you being a main target. You just… yeah, you came across really well,” you finish.

You suddenly realize that as you’ve been speaking, your hand has migrated from his shoulder to his upper back, and you’ve started to rub small circles against the smooth fabric of his button up shirt. He sighs, his head still hanging low, and you feel his muscles relaxing slightly.

“Thanks,” he mumbles softly, and you aren’t sure if it’s in response to your complimentary words or your soothing touch, but it doesn’t really matter as long as you’re helping him feel a little better. You continue rubbing his back gently for a bit until he slowly sits up straight again. You take this as his way of saying you can stop, so your hand retreats to your lap. You immediately wish you had another reason to keep touching him.

He takes a deep breath. “It, uh…” he stammers before pausing for a second, like he’s figuring out how to properly word what he wants to say. He leans back against the couch. “It would have been nice to have had you there,” he says, eyes glazed over and directed at the floor. “Jess was great, of course, you just, you have a comforting presence…” He hesitates before he looks over at you.

You hold his eye contact for a moment before your gaze drops to your lap. This conversation is heading in a risky direction - you should shut it down, say goodnight, and go home, but you can’t stop yourself from leaning into it further. The two of you can never be seen together outside of work, and right now, in his office with everyone else gone, is probably the only opportunity you’ll get to have another meaningful in-person conversation with Kendall. So, instead of being smart and leaving, you stay and say what you’re actually thinking.

“I uh, I’m actually kind of relieved that I wasn’t there,” you say lightly, fiddling with your fingers in your lap.

In your periphery, you see Kendall nod. “I get that… it wasn’t the most enjoyable environment to be in.”

“No, it’s not that…” you waver. Fuck, are you really gonna say this? There’s no coming back if you do, but maybe that’s what you actually want. The tension between the two of you has been built up too much and it needs to break. “Just… watching you… you know, do your thing, it um,” you laugh awkwardly, and Kendall sits up beside you as he waits for you complete your thought. You keep your eyes in your lap. “… I’m not sure I would’ve been able to play it cool around you after that.”

You keep your eyes down, but you can feel Kendall move closer to you, and when he speaks, you can hear a smile in his voice. “Oh yeah?” he says smugly. “You wanna elaborate?”

You roll your eyes, still keeping them off his face. “Oh my god, I already said you were powerful,” you groan jokingly. “What else do you want from me Ken?”

You’ve never shortened his name before. Jess always calls him Kendall, so using his more informal name would be suspicious. It slips out now though, but you don’t regret it. It just happened naturally, and you’re ashamed to admit it, but you love how it sounds coming out of your mouth. It feels a bit like how you would talk to him if he was your boyfriend. It’s nice to get to live in that world for a second.

“I want a whole fuckin’ sentence,” he laughs, and he moves even closer to you. Your legs are barely an inch apart, you can practically feel the heat radiating off him. You finally look up at him.

“It was hot, okay? You were hot, is that what you want to hear?”

His lips are on yours before you can react, but you don’t need to. Your response is immediate, as if you knew it was coming, and you fall into him like it’s second nature.

Kendall’s hands grip your face, his fingers knotting themselves into your hair. Your arms race to wrap around his neck, and you pull each other in. This is only the second time you’ve kissed, but it feels strangely easy, like it’s something the two of you have been doing the entire time you’ve known each other.

His mouth moves furiously against yours, his tongue slipping past your lips, and you feel excitement begin to build in your core. You could lie to yourself and pretend that you didn’t ache for him when you were in an office surrounded by other people, but it’s impossible to do that now with with his hands exploring every inch of your body.

Your arms loosen themselves from his around his neck and your hands slide their way down to the neckline of his dress shirt. It’s unbuttoned low enough for you to access the skin of his shoulders and upper back, and you sneak your hands underneath the fabric, desperate to feel his warmth. Your urgency to get under his clothing has him groaning against your mouth, and he pulls you onto his lap, his hands not hesitating in gripping your ass as he does. You straddle him, your core resting on his groin, and you can feel him hardening by the second.

Your hands travel down his chest to the buttons of his shirt, which you begin to undo frantically, and you feel Kendall continue to grow beneath you. God, knowing that you might get to feel him inside you again… it sends a rush of heat coursing through your body that settles snuggly in your lower stomach.

His hands still on your ass, he begins to guide your hips forward and back over his own, pulling your body down onto his so you can grind as much pressure against him as possible. The way your centre hits his just right is heaven. You break apart from his lips to moan into his neck, your hands still working away at the tiny buttons lining his shirt, his hands still guiding your hips.

“Fuck,” he husks into your ear, “god, fuck I need you,” and he begins to move your hips faster. Your fingers undo the last button of his shirt and you spread it open, pushing it off his shoulders and revealing his chest. You’re both feeling that same sense of urgency now, and Kendall’s hands leave your hips to travel to the hem of your shirt.

RING RING RING

The phone in his pocket sounds off, startling you out of your embrace.

“Jesus fuck, sorry,” he apologises as he pulls it out, and it looks like he’s about to silence the ringer when you both see the name on the screen - ‘Dad.’

He looks up at you. “Yeah, fuck, I should take this,” he says, and you immediately climb off him, returning to your spot on the other side of the couch. Kendall stands up, his shirt still open, and answers the phone.

“Yeah, Dad,” he says, and you can hear Logan’s gruff tone on the other side of the call. Kendall listens for a bit, his back to you, just nodding. “Yeah, okay, I’ll uh, I’ll make my way there. Okay. Yeah, see you soon.” He hangs up and hesitates before turning back to you.

“… Everything alright?” you ask. His eyes are fixated on his phone screen and he’s typing furiously.

“Um…” he says as he finishes writing his message. You hear the 'whoosh' of a text being sent before he locks his phone, stuffing it into his pants pocket. He then begins to button his shirt back up, and disappointment washes over you. “I… yeah, I don’t know. He’s organising a vacation for everyone… like my entire family, all the higher ups… pretty much anyone who could possibly take the fall for the Brightstar mess.” He shakes his head as he does up the last button. “Doubt it’s gonna be a fucking team building session or whatever.”

He finally looks over at you, pausing for a moment as his gaze turns a little softer. “It, um, it was probably good that we got interrupted before we did something stupid, right?”

You look down and nod. As much as your entire body wants to pick up where you left off, he’s right. What were you gonna do, be the assistant who fucks the CEO’s son on company property? What a fucking cliche. Add in the embarrassment of Kendall being the one to call it off, and now you can feel anxiety starting to build in your chest. What began as something you desperately wanted is quickly shifting into the most shameful moment of your life. You have to get the fuck out of here.

You stand. “I should go,” you say. “Um… I hope the trip goes well, and I’ll, I’ll see you after.” You don’t wait for a response from him, you leave his office and quickly grab your keys from your desk. You don’t look back.

The elevator doors slide open immediately for you, and you rush to enter, scrambling to press the button for the ground floor. You lean up against the wall as it starts its descent, exhaling a shaky sigh.

Fuck.

What now?

Tag list: @foreverasleep717 @berryfinch @ad-astra-again @18dmlk @maraschinodreamo @loveandthings11 @waystarnatco @allcheesemelts @r0semaryjane @l2theogan @fictionalmen-dilflover @thetorturedpoetssdepartment @randomnessfangirl @meowmeowyoongles @verchans @midcenturymanhattan-blog @straightedgevixen @vikingsisthenewsexy @joyfulpersonbeliever

#this is soooo good I can’t wait to see where it goes

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youreirrelevant · 3 months

Text

million dollar baby - kendall roy

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

word count: 4,510

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

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

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

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

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

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

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

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

“You’re Kendall, right?”

His eyes narrowed, the end of his cigarette crackling.

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

“Sorry, the taxi was really slow.”

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

“Oh. Haha,” you deadpanned.

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

“Hard to tell.” Your face burned.

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

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

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

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

“I hear you want to go into politics?”

“Yeah, I do.”

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

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

Clearly not enough.

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

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

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

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

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

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

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

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

“Food should be good,” he said simply.

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

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

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

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

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

Cecily’s reply came within the minute:

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

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

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

“Ugh,” you murmured to yourself.

“Fine.”

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

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

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

───── ⋆⋅☆⋅⋆ ─────

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

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

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

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

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

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

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

“With the… cocaine?”

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

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

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

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

“Okay. I’m sorry.”

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

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

From Cecily: How’s it going??

You switched it to silent.

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

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

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

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

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

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

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

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

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

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

“Um, both, I guess.”

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

“All first dates?” he asked.

“Yeah, pretty much.”

“Are most of them bad?”

“Kinda.”

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

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

“What?” he laughed.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

“Oh,” was all you could manage.

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

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

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

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

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

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

“How vintage of you,” you teased.

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

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

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

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

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

“Mhmm.”

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

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

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

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

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

“Please,” you whined.

“Please what?”

“Please, fuck me.”

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

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

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

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

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

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

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

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

“Yes,” you admitted breathily.

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

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

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

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

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

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

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

“Y-Yeah.”

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

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

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

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

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

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

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

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

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

Damn it.

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

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

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

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

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

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

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

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

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

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

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

“Yes,” he said tersely.

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

#ugh YES #SO excited when I saw this #and also it got my brain going to figure out some stuff for a fic I’ve been wanting to write so 🫶🫶🫶

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