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#they work at waystar royco
cottoncandysprite · 5 months
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Colin Robinson, the long-suffering HR director: "That's his boss......... :/"
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kazanskyy · 1 year
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tom originally planned to go to this year’s company halloween party as mark antony to shiv’s cleopatra (his idea, obviously) but now he’s on the way to a finalized divorce and very much without a costume partner so he just passes the outfit off as “generic roman general” while also making unsubtle nero callbacks that only greg gets. meanwhile, greg throws together a pretty low-effort cowboy costume cus it’s easy and he already had most of it, and really this party is just an excuse to get drunk with tom and have a good time. they don’t think anything of the fact that they spend the whole party in each other’s company until the next day when greg opens his email to find he and tom were somehow nominated for and won the “best pair” costume category for octavius and jedediah from night at the museum.
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homoqueerjewhobbit · 3 months
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Business: 💖💓 we're family owned 💗💞
Me: So was Waystar-Royco
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grendelsmilf · 1 year
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tom and greg have a hilarious dynamic their exchanges (and toms lines in general) are some of the funniest dialogue in the show, and the fucked up implications of tom like. offloading his misogyny/projecting his emasculation onto greg are genuinely fascinating but I cannot for the life of me understand how people ship them in like a very genuine & earnest way?? some of y’all will see two tall, ugly, obnoxious white men and black out , methinks
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westzane · 1 year
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Idk something about this pregnancy storyline not sitting right with me. It feels kind of cheap. Not very succession-like at all. Almost like a cop-out to put Shiv in that situation because now a massive part of her storyline is about whether she’s going to get back with Tom and whether she’s going to keep the baby. And it feels like the more interesting storyline of whether shiv is finally going to earn some credibility within the company and actually prove herself and maybe put herself in strong position suddenly takes a back burner. This finally feels like the season where Shiv gets to play with the big boys and I hope that isn’t taken away.
Ultimately, though, Shiv is the only one who’s relationship is a main focus on the show, which inevitably eats into her storyline. It takes away from Shiv the individual to give to Tom and Shiv (in that order). Given that, I don’t know if they’ve given enough to Shiv the individual to have earned this pregnancy. Although maybe it’ll give us more insight into Shiv the individual, the one with mother issues, the careerist, the vengeful spiteful cruel Shiv. But I have a feeling it will be more about Tom and how this is an in for him to get back into Shiv’s good books, and subsequently, and more importantly, back into the inner circle.
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finitevariety · 11 months
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"Logan Charles Roy was a legendary news proprietor, a media visionary, a brilliant businessman, a job creator and, above all, a loving family man. For over 60 years, he presided over the company he founded, Waystar Royco, the largest family-owned media conglomerate in the United States.
Logan's childhood was marked by adversity. Born in Dundee, Scotland, on the eve of World War 2, his father died shortly after his birth. A few years later his mother, Helen Roy, sent Logan and his older brother Ewan to Canada to escape. They were never to see their mother again, and their sister Rose also died as a young child. Both Logan and Ewan were raised in rural Quebec by relatives.
Though academically gifted, Logan left school at the age of 13. After a brief period working as a store clerk, Logan inherited his Uncle Noah's small advertising billboard company along with his brother Ewan. Over the next decade they grew their small businesses into the largest billboard companies in Canada. From there, the brothers' diverging interests saw Logan take control of the company.
Logan moved to the United States in 1972, determined to diversify Waystar Royco by moving into media. He quickly acquired several declining newspapers, such as the New York Globe, working his magic to dramatically turn these around and [elevate?] them to their former glory.
Logan firmly established himself as one of the country's most important media moguls with the launch of ATN, American Television News, in 198[1?/4?]. Now widely regarded as the nation's most [?respected] news source and a [?format admired] around the world, ATN changed the American media landscape overnight. Since its launch, ATN has, in the service of public interest, provided a [??] breed of television ...
[STEWY FINGER INTERLUDE 👀 ]
... several American Presidents ... necessary, a strident defender of the ... American people against threats both [[?? and ??].
Though Logan scaled such lofty heights [??presumably 'in his'] public life, he remained a humble individual, prioritizing his work, his family, and his [??]. He is survived by his wife Marcia and his children, Connor, Kendall, Siobhan and Roman Roy."
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starsandsugars · 11 months
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Burning Desire
PAIRINGS: shiv roy/f!reader
SUMMARY: you had hoped that working on a work assignment with shiv might make her open up to you. Instead it lead to you 'opening up' in an entirely different way. (NSFW • MINORS DNI)
TAGS: coworkers hooking up, degredation, praise, office crushes, cheating (if you squint)
NOTES: hi guys :) this is my first fic I'm posting on tumblr and my first piece of smut so please be nice and I hope y'all like it!
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Your heart hammered in your chest as you felt Shiv's hand press firmer against your mouth, forcing you to keep quiet even as she continued to pump her fingers into you at that ruthless pace. Each stroke of her fingertips hit that perfect spot inside you, drawing out animalistic sounds that were just barely concealed by her. Every little touch made you feel electric, every inch of your body practically vibrating from the pleasure.
As your head tilted back and knocked back against the door, you thank whatever God there was for putting you in this situation.
You had seen Shioban Roy countless times around the Waystar offices, normally in some meeting or getting into an argument with her siblings that half the staff had to witness.
You knew very little about her initially other than what was public knowledge. You had no reason to pay her any mind, but you always felt your eyes drawn to her anyway.
At first you reasoned it was because of the effortless way she commanded the room or the fact that, as Gerri's second in command, she was kind of your bosses boss but as your curiosity began to change shape it became harder and harder to deny.
You couldn't tear your eyes away from her if she walked by your desk, the simple twirl of her hips enough to take your breath away. When she leaned over her desk to talk to you, you just about lost your ability to think clearly. And the one time you saw her kiss her husband in the lobby it filled you with a feeling you refuse to admit even to yourself.
It was ridiculous, and beyond irresponsible.
For one, she was your boss. If that wasn't enough she was married - to the head of news at the company that you work for no less!
You did your best to convince yourself that it was just an office crush. She was a beautiful woman with a touch of power that turned you on more than you wanted to admit. That was surely all it was.
Or it least, that was all it had been, until you got assigned to work on an agreement that Shiv, as President of Operations was hwading. t really wasn't an overly complicated assignment, which is why Gerri handed it over to you, and you expected to be done with it in a couple of days.
As it turns out, that was far from the case. The other company refused to sign, and what could have been a couple meetings turned into long days and nights cooped up in Shiv's office hunched over paperwork.
Your silly crush hadn't gotten away, and had gotten even harder to manage. Now you were close enough to smell her expensive perfume, close enough to hear the edge her voice took when she was telling you to do something.
You tried to push it down, smother it, but the flame only grew brighter with each day you spent together.
Finally, after a million emails and a formally worded threat of litigation, the smaller tech company signed the contract and became a part of the growing monolith that was Waystar Royco.
You had never seen Shiv happier, practically beaming as she went immediately to gloat to her father. You took your things and disappeared back to your own office, expecting that would be the end of your Shiv Roy saga.
You were a little sad to see it end, but you're sure your vibrator will thank you for a break now that you won't have to constantly be so close to her so you prepare yourself to just move on.
You should have known things with her could never be that simple.
Just as you began to catch up with your other work you've been neglecting to help her she pops her head into your office.
"Come out with me to celebrate our win." She says without so much as a 'hello', "Drinks on me."
It wasn't a request so much as a command, but you found yourself agreeing anyway.
With that she turned on her heels, leaving you with a fluttering feeling in your stomach.
You were distracted the rest of the day wondering what she was up to. Did she really just want to celebrate? What was her game here? You knew the Roys well enough to know they never did anything without an agenda.
By the time she came to get you from your office at the end of the day you were all but convinced she was going to fire you. You went with her anyway, heart thumping in your chest as the two of you sat quietly in her private car.
She had her driver take you two to a high end bar that seemed to be pretending to be a dive bar. It was busy, with warm bodies and loud music everywhere. It could almost pass for a normal bar if it weren't for the suits all around and the fact that one of their drinks rang up for twice as much as your hourly wage.
She (thankfully) bought you your drink and turned to gave you fully once you had both settled into a leather booth.
It started off perfectly innocently, talking about you success with the deal and your future at Waystar. Your anxiety began to melt as you realized she really wasn't firing you. In fact, she seemed like she genuinely wanted to talk to you.
You talked your way through another 2 drinks each, both of you slowly opening up to each other. You told her about how much Gerri gets on your case and she tells you about her open relationship with Tom.
She drops it into the conversation casually but the way she blinks her eyes gives her away. She knows exactly what she's doing.
"I mean, I don't control what he does. Why would I let him control me?" She leans a little closer, and the finger tracing the rim of her drink turned into a heavy hand on your thigh.
Her voice lowers as she continues, sending shivers down your spine.
"I sleep with whoever I want. Whenever I want."
Your voice choked up a little as you responded, voice sticking in your throat from the sheer shock of it all.
"Yeah, me too." You manage, drawing a laugh from the redhead.
"Oh yeah?" She teases, eyes twinkling as she whispers into your ear.
"Why don't you come show me?"
Before you can even begin to think better of it her ingers splayed are across your back and she's guiding you to the back of the bar.
She opens a door knowingly and you realize she had planned this. If she had to have an angle, you were glad it was this one.
Once the two of you were inside she pressed you back against the door. The cold metal pulled a shiver from you, but the second her lips were on yours it's like every other sensation melted away. She kissed you like she wanted to consume you and you would be more than happy to let her.
As if reading your thoughts she bit your lip, pulling a little yelp out of her. She grinned and moved her lips against your neck as her hands slid up under your dress. You preened under her touch, breathy moans escaping you despite yourself.
It took only a moment for your panties to be tugged down your legs but she paused before actually touching you. You tired rolling your hips but all she did was brush your clit all too softly.
"Shiv, please." You begged, tapping into the want for submission she so clearly had in her normal life. The tendency clearly extends to sex because as soon as you give her what she wants she finally pushed her fingers into you.
She was clearly skilled with her fingers and she worked you up in no time. You moaned loudly, and she gripped your chin to warn you.
"Be. Quiet."
When you couldn't comply she shoved her hand over your mouth, gripping your cheeks to keep it in place. When you whimpered enough to be heard through her attempted gag she crowded you further against the wall.
"Shut up."
She spoke into your ear, equal parts threat and promise.
"Unless you want us to get caught. Maybe you'd like that. Maybe you want everyone to see what you let me do to you in this bathroom."
She strikes just the right spot inside of you and your thighs begin to quake, fingers clutching desperately to her shoulders. You know you should try to maintain some level of basic self respect but when she looks at you with those hungry eyes you just can't find it in yourself to care.
"God you're such a slut." She says, sounding pleasantly surprised. The words send sparks down your spine and you feel yourself tumble over the edge.
Your mind is hazy and your legs shake so badly she has to use her thigh to prop you up.
Once you had calmed down enough to do something that resembled normal breathing she let you go, smiling like she's just won some kind of contest.
"Good girl. I knew you had it in you." She says, and it's a struggle not to let the praise go straight to your head.
She starts to check her reflection in the mirror over the sink as you stay against the door, trying to make your brain work properly again.
Eventually you come to your senses enough to straighten up and try to appear half as nonchalant as she is.
You approach her, leaning against the sink as you watch her fix her hair.
"You're not going to let me return the favor?" You ask with a tone od faux innocence, trying to talk as if it were about a business deal instead of the most mind blowing orgasm of your life.
"Oh trust me, you're going to." She grins at you in the mirror. "But we're not doing this again in the bathroom. We're going back to my apartment."
She strides right out of the bathroom, knowing you were going to follow her without you having to say a word.
She's not wrong, and you chase after her before you even have the time to realize your panties are still discarded on the bathroom floor.
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brookheimer · 1 year
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shiv booking herself a room to grieve her dead father in because she does have emotions about it she is grieving she is crying but if she as a woman at waystar royco is seen showing them anywhere at any time she is ruined. the boys can boss everyone around can arbitrarily fire anyone who looks at them wrong roman can fire a longtime executive because she mentioned his dad kendall can be on the verge of tears when a set designer is unable to create realistic looking clouds in less than a day of work but shiv? shiv can't do any of that. shiv has to be stone. when men show emotion in the workplace, it isn't seen as emotion, it's seen as Man. anything a woman does in the workplace is seen as emotion and thus seen as Woman because the two are seen as being virtually interchangeable. shiv schedules her grief because it exists and she isn't actually the emotionless pinnacle of masculinist ideals (independence, self-sufficiency, pride, stoicism, distance) she tries to be but god is she fucking trying to be so she blocks herself out a twenty minute period of time to be a person because if she's a person in public then she becomes a Woman and that's untenable.
big fan of that specific choice from the writers' end because that was honestly a really smart way to straddle the modern 'conundrum' facing female characters -- it allowed her to simultaneously maintain masculinist respect and human emotionality, while very much drawing attention to the absurdity, cruelty, and inhumanity of both the expectations she's trying to meet and the degrees she must go to meet them. typically Strong Female Characters must be emotionless hard-hearted and cold if they hope to remain Strong. if they show emotion they are demoted from Strong Female Character to just Female Character. what a brilliant way to circumvent that -- it's not just Strong On The Outside Soft On The Inside or whatever, it's a character study moment while also being a metatextual critique of the absurd boundaries and forced emotion regulation placed on women not only in the workplace but on the screen. shiv hiding her moment of vulnerability shows that she hates it too, knows it's weak and bad and wrong too; shiv going out of her way to schedule moments of alone time to have emotions shows she won't let her emotions get in the way of anything important -- she's internalized the bizarre masculine emotional narrative deeply enough to be respectable in the audience's eyes, thus maintaining her position as a Strong character despite being seen acting like a "Female" one. but ! it's still framed so absurdly and painfully that it additionally works on the level of meta commentary, highlighting just how small and high the hoops female characters have to go through in order to be seen as respectable by a general audience while also retaining their humanity and emotionality (that male characters are free to express however they'd like)
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leviathanspain · 2 months
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you NEED to write more for Tom 😭😭😭 like I’ve been thinking so much about age-gap f!assistant tropes with Tom it’s actually insane, like Tom asking you nonchalantly to ride his thigh (or him) in his office 🌸🌸
skin tight
tom wambsgans x assistant!reader
synopsis: tom knows how to push your buttons perfectly, and you let him
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tom wambsgans was a total asshole. he was arrogant, thought himself to be the hottest piece of ass to ever come out of ATN and you were stuck working for him, bringing him coffee just to never drink it, or to make you run all around the city looking for a bagel that didn't exist. it was an endless cycle, but you found him to be the most tolerable associate of the roy family, and decided that between him and kendall, being tom's assistant wasn't all that bad.
if you ignore the obvious sexual tension of course.
"here is that-" you didn't get to finish your sentence before tom waved you away. you sighed, rolling your eyes as you spun on your heel and stepped out of his office, tossing the scalding cup of coffee into the nearest bin before settling back down at your desk. that had been the third time today that tom had made you get things for him, just for him to send you and it away. normally you wouldn't let this behavior phase you, but it was starting to get to be too much.
there had been a break in your thoughts and you turned to glimpse into tom's office, and found him already looking at you. you gasped slightly in surprise and stood up, knowing that this had been no coincidence.
you kept your head bowed as you stepped inside the office. you could feel his eyes on you, feeling the irritation coming from his gaze. you swallowed thickly, "tom?" was all you could manage, unsure of what to say, especially to him.
"close the blinds," he spoke quietly, not whispered but a quiet, and serious tone. you did as he said, moving to first close the one directly facing your desk. you watched as the life of the ATN office was shut away by the white blinds. your hands shook slightly but you finished the rest. you turned around, silently waiting for him to speak.
he finally did speak, after a minute of unbearable silence.
"now come fuck yourself on my thigh." his words had left you speechless, but you weren't exactly opposed to not doing as he said. you stared at him for a moment and he shrugged, "clearly you've been angry with me. i am giving you an opportunity to release that anger." he spoke cooly, glancing over at his computer, as if this was like any other work conversation.
you waited, thinking.
"okay." you decided, and watched as tom looked up in mild surprise, as if he hadn't expected you to agree. how could you not? not when he's been subtly hitting on you since your employment. tom wambsgans was an asshole, and cheating on his wife had been nothing new at this point. nearly everyone in waystar royco had heard of shiv and tom's marital problems.
tom watched as you walked over to his desk. you were wearing a tight black pencil skirt, so tight that he could see your hip indentations. you leaned against his desk, his thigh next to you. "i need you to pull my skirt up. It's-" you didn't finish, his fingertips grazed your skin as he shucked your skirt up, seeing your lacy underwear peeking out. he looked at you and you remained unmoving, letting him proceed to remove your panties, gently pulling them and letting them slide down your legs.
he patted you to step out of them. you inhaled a breath as his finger ran once over your slick folds. your breath shook slightly but your thoughts were clouded by lust. all you could think about was how good your cunt will feel against his thigh.
tom didn't remove his pants. he was going to let you fuck yourself on his hundred dollar suit pants.
you hovered over him, and his hand found it's way to graze your cheek, brushing your hair back as you finally sat down on his leg, feeling the friction of the fabric against your cunt. you shivered, and tom's hand moved to your waist, gripping it.
you inhaled sharply as your hips began to move.
"i was doing it on purpose." he spoke, eyes glued to the sight of your pussy grinding down on his thigh. tom smirked, "watching you listen to my demands like it was the word of god.." he trailed off and you grunted, "shut up." you whispered weakly, too focused on the pleasure to defend yourself properly.
you knew tom saw you as nothing but his young female assistant, nothing other than someone to fuck. what you were currently doing did not help your image. in his eyes, you were weak, a plaything, a punching bag.
you moaned, unable to hold yourself up, you grabbed onto his shoulder to steady yourself. tom grunted softly, "mmhm, let me hear you baby." he whispered, hand brushing through your hair. it was slightly romantic, and it made you feel uneasy. romance was something that had to be avoided at all costs with tom wambsgans.
you panted, and gripped his shoulder tightly as you felt yourself getting close. he chuckled deeply. "you're so wet, you're seeping through." he loved it, he loved how good his thigh was making you feel. he could only imagine how you would look stuffed with his cock.
you shivered, moaning loudly as you came all over his thigh. tom gripped your waist, and he was smirking, watching as you fell against him. he was warm, the fabric of his suit felt nice against your cheek. even his hand had been rubbing your back.
you jolted up, and awkwardly leaned off. you stood up, deciding to struggle to get your skirt down as he looked at the mess you had made on his thigh. you were blushing red, hot and absolutely bothered. you stared at him, and at your crumpled panties that you had forgotten to slip back on. he followed your gaze and picked them up.
tom stuffed them into his pocket, and scooted back behind his desk. he began to work as if nothing happened and you remained planted, quiet and exhausted.
tom didn't glance at you, "you can go. and don't ever roll your eyee at me again." you began to walk away, "yes, sir."
asshole, you thought silently, letting his office door slam behind you as you walked past your desk, deciding to take the rest of the day off.
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tomshivendgame · 10 months
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tomshiv - romcom edit (uptown girl by billy joel)
pov: Succession AU where Tom works at Waystar Royco as Shiv’s assistant
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mandobatemans · 9 months
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intrigue (Tom Wambsgans x f!reader)
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warnings: infidelity, fingering, unprotected piv sex, soft!dom tom, size kink kinda, biting, greg, do NOT have sex with the head of conservative news organizations irl!!!, i am a shivcel fr anything negative abt shiv in here i didn't mean it ily siobhan 🫶, NSFW UNDER THE CUT
word count: 4,740 (i got carried away)
A/N: this is loosely based on s4 e7 but there's no real timeline so it probably takes place like somewhere around season 3 or 4? this is my first succ fic so...enjoy 🤗 & also this took me SO long to write i'm so deeply sorry to anyone who was waiting
also posted to ao3
Tom had never been a fan of the whole “open marriage” arrangement. When he thought back to that fateful night (fateful night…who else would say that about their wedding night?) what he remembered most was the look on Shiv’s face when she told him that she wanted an open marriage. On their wedding night.
It was more for Shiv anyway. Tom rarely thought about actually acting on the arrangement, whether it be out of love for Shiv or loyalty to her father, he wasn’t sure. Sure, he had kissed someone here or done oral there when high on coke, but he had never actually fucked anyone else.
Something was different, though, tonight. Firstly, they were hosting a Waystar/ATN event at their apartment, and despite being chairman of ATN, he wasn't even sure what the evening was for. Shiv had told him about it last minute, casually mentioning it as they were being driven to work, like it was dinner at Logan’s rather than hundreds of media moguls and politicians to host. Actually, dinner at Logan’s felt equally, if not more, important than tonight. A better equivalent for how nonchalantly Shiv had mentioned it would be Connor inviting them somewhere.
Secondly, Shiv had suggested, outright, that they both find someone to hook up with at the party tonight. Earlier in their bedroom, after getting dressed in silence, Shiv had turned to Tom while putting her earrings in to share the idea. He knew she would be acting on it whether or not he did, and why shouldn’t he? It had been a while since he had gotten laid and was verbally (and physically) assaulting Greg a lot more as a result.
Did he just pick someone? How did you approach someone and say, “Hey, I’m in an open marriage but I’ve never actually done anything more than get my dick sucked with anyone else…anyway, let’s fuck!”
Tom fidgeted with his glass as he surveyed the room.
Despite your personal beliefs and the endless human rights violations that Waystar was affiliated with, their (and by extension ATN) events were some of the most lavish you'd ever attended. As a political journalist, it was standard for your company to send a journalist or two to whatever soirée the Roys were throwing. Everyone took turns, and this time you had drawn the short straw. It hadn’t been too bad so far, you thought, although perhaps you were jinxing yourself. You had kept to yourself mostly, chatting with other journalists you frequently saw around the city on assignments, snacking on the hors d'oeuvres, and listening to the ridiculous conversations political and media bigwigs were having.
You had been to an event hosted by the Roys before, but they were usually at ATN, Waystar, or some expensive venue. Being invited as a member of the press to Shiv Roy’s apartment felt strangely intimate. You were certain this was some calculated business move on the part of one Roy or the other, but you honestly didn’t really care. Whatever drama was happening within Waystar Royco was contained within the Roy family. You were simply here to supplement a piece your coworker was writing on the atmosphere of this political season.
It was only an hour into the party when you had collected all the quotes and interviews you needed, and sampled almost all of the hors d'oeuvres. Your boss expected journalists to stay for most, if not all, of the night for these things, in case some political bombshell were to happen. You were pretty sure nothing too monumental was going to happen in this room full of suits, especially with all of the Roys notably absent from the festivities. Even Shiv, whose house it was, looked like she wasn't paying any attention to what was going on in her home. In fact, she had been in the corner all night, talking to some prominent New York and D.C. women, important enough that you knew their faces but not important enough for you to attach any names to them.
You checked your phone for the time. You could probably get away with leaving in another hour if you made up some family emergency as an excuse for your editor. Even another hour seemed like ages. Maybe you could re-interview some people? Speak to some guests whose quotes would never make it in the article just to kill time? Sighing, you opened your messages, thumbs hovering over the chat with your editor, putting your journalism degree to use by brainstorming an excuse to get you back home in your bed before ten o’clock. When you turned around to pace while you typed (a nervous habit), you found yourself face-to-face with one of your hosts.
It felt like a fucking cliché. Literally bumping into someone at a party? If one of your writer friends wrote something like this, you'd tell them it was bullshit and things like that didn't happen in real life. Yet here you were, inches away from–
“Tom Wambsgans, Chairman of Global Broadcast News at ATN.” He introduced himself, reaching out a hand for you to shake.
You returned the handshake, grateful that he wasn’t offended by you bumping into him. “I know who you are.”
“And I know who you are.” He paused. “That sounded stalkerish, didn’t it? I meant, I know who you are because I’ve read your articles.”
“You have?” You were surprised. Your company and your articles in particular were considered left-leaning, the very opposite of the stories ATN ran.
He nodded. “Gotta keep up with the competition. I’ve seen some of your features on the network, as well.”
“Really? I would have thought you would just watch ATN all day,” you teased.
Tom made a face and then shook his head. “No, no, no. Plus, I wouldn’t really call any of our journalists ‘journalists’ so much as pretty faces. You do your own research and look good on the camera. That’s impressive.”
You raised an eyebrow and Tom’s eyes widened, processing what he had just said.
“God, I do sound like a fucking stalker.”
You laughed, “Just a little bit.” You let him cringe for a second, then smiled to reassure him. “No, but I’ve seen some of your interviews since you took over ATN. You look good on the camera, too.” You paused, before adding, “Maybe that makes us both a little stalkerish.”
His eyes lit up at your response, earning a genuine laugh (the first one that night not faked for some suit, he noted).
“Uh, sorry for bumping into you. I wasn't looking where I was going,” you explained, waving your phone in your hand for context.
“Ah, cell phone. The curse of the twenty-first century.”
You furrowed your brow involuntarily for a moment. He wasn't how you expected the spouse of a Roy to be like. Whether that was a good thing or a bad thing, you weren't yet sure.
“I’m making a huge ass of myself, aren't I?” He sighed. “I’ll leave you to the party–”
“No! It’s okay. Stay,” you heard yourself say. It was Tom’s turn to raise an eyebrow. Okay. You found him attractive. And even despite his eccentric comments, you also found yourself wanting to talk to him more. You were, however, purposely avoiding looking at the wedding ring on his finger.
To Tom, it all seemed too perfect. You, for example. He was being honest when he said he had seen and read some of your work and that he enjoyed it, and he did sometimes watch other networks to get an idea of the competition, but he had left out the fact that there was something about you in particular that made him watch the entire segment when you happened to be on air. And the fact that sometimes he'd scroll through your articles online and imagine you reading them aloud to him. But he wasn’t a stalker. And now you were here, in his house, on the night that his wife had all but shoved him into the bed of anyone that he wanted.
But still; one pleasant, slightly flirtatious conversation didn't mean you wanted to ride off into the sunset with him. Or, more accurately, go upstairs with him.
He scanned the room for Siobhan. Although it had been her suggestion, and he knew she had acted on the arrangement before, he still felt like it was somehow a trap. Like she’d hire someone to hide behind the bedroom door that night and catch him with his pants down (literally) to use as blackmail.
But sure enough, she was across the room, laughing at something some lobbyist had said, and resting her hand on the other woman’s arm slightly longer than a casual touch would last.
The longer he thought about it, the more confident he felt. If you were interested, he wanted to spend the night with you. And maybe more. But he was getting ahead of himself.
“It's kind of loud over here. Come on,” he gestured with his head toward the opposite corner of the apartment, one not occupied by any guests save for an elderly politician snoring on the couch.
You followed him, nodding when he asked if you wanted another drink before picking a champagne flute off of a passing server’s tray. He handed it to you once you reached the corner, your hands touching during the exchange. It seemed like even more of a cliché to feel sparks fly at this tiny touch, so you ignored that, as well.
“You host these kinds of things often?” You asked, leaning against the wall and taking a sip of your champagne. The room was full of very important people, though none of them seemed to be talking about very important things. You couldn't quite wrap your head around why a high-level executive who had married into one of the largest media conglomerates was wasting his time talking to you (flirting with you?), but you had seen stranger things in this city.
He grimaced and shook his head. “No, no. I’m usually just a guest.” Tom laughed and took a sip of his drink. “And not a very important one, at that.”
“I’m sure that's not true. I mean, how many people watch ATN? And you’re in charge of what airs or doesn't air.”
“1.89 million,” he replied, taking a sip of his drink, “Outside of the office, nobody’s really worried about what I think.”
“Not even your wife?” You stopped after you said the words, giving your brain a second to catch up with your mouth. “I’m sorry, I didn't mean any disrespect, I–”
“No, no, no, no, it’s okay,” he assured you, reaching out to rest a hand on yours consolingly. Tom leaned in closer so only you would hear him, unnecessary considering the secluded corner you two were in.
“But no, not even my wife.”
Your eyes darted to his hand atop yours, suddenly aware of how large his hands were. They almost completely covered yours, and they felt so comfortable and right there, like–
“We have an open marriage,” he suddenly said.
“Oh.”
Tom seemed disappointed with this reaction, quickly removing his hand from yours and adding, “That’s just to say that, our marriage is, uh, unconventional, so her not caring what I have to say isn’t that unusual.”
You were still processing the feel of his hand on yours, much less the revelation that he actually might be flirting with you and that it actually might go somewhere. By the time your thoughts caught up with you, it seemed like he was about ready to excuse himself and go scream at his reflection in the bathroom.
“Well, I’m sorry about that,” you responded, mirroring his gesture from before and resting your hand on top of his to comfort him. “You don’t deserve that, really.”
He scoffed. “You don't know what I deserve.”
You looked up at him, taking the time to absorb the look in his eyes that revealed just how much he was going through.
“Uh, Tom?”
Tom rolled his eyes and turned away from you to snap at the source of the interruption. “What, Greg? Can’t you see I’m having a conversation?”
“It’s just–well, Shiv is leaving with someone.” The taller man gestured at the door, where sure enough, Shiv was weaving her way through the crowd toward the elevators with the lobbyist from earlier, her hand guiding her by the small of her back.
Tom bit the inside of his cheek. “Well, Greg, we do have an open marriage. So, everything’s fine. Now, scram.”
Greg looked between the two of you and hesitated for a second before nodding and disappearing back into the bustle of the party.
Tom turned back to you. “That’s Shiv’s cousin, Greg. I’ve sort of taken him under my corporate wing, so to speak. Showing him the ropes and all that.”
You nodded, finishing your champagne.
“Well,” he said.
“Well,” you echoed.
He paused for a minute, though it seemed to last much longer than that. “You’re writing an article about this party, right?”
“Yeah,” you responded, unsure of where he was going with this.
Tom leaned in, lowering his voice. “What would your editor say if you got a behind-the-scenes look at the party?”
You raised your eyebrow.
“Of course, you'd have to come upstairs…” Something shifted in his tone. You were well aware of what the change implied, and you’d be lying if you said you didn't want to jump at the offer. This wasn’t you, though. Sleeping with a married man? On top of that, not just any married man, but the host of the party that you were covering for work. It sounded like a problem you’d encounter on an Intro to Ethics exam. But any moral qualms you had about the issue were pushed out of your head when you registered the way Tom was looking at you.
“Of course,” you repeated, nonchalantly, setting your empty champagne glass on a nearby table.
Something flickered in Tom’s eyes. “Shall we?”
“Lead the way, Wambsgans,” you replied, gesturing dramatically.
Neither of you spoke for the entire walk away from the excitement of the party to the quiet of Tom’s bedroom. It looked much like you had expected it to look: modern, chic, and impersonal. You were sure Tom (or Shiv) had some personal items somewhere in the house, but the bedroom was so clean and styled that the only indication anyone slept or dressed in there was some of Shiv’s makeup and jewelry strewn haphazardly on the vanity.
When he had closed the door behind you, Tom stepped closer to you experimentally, as if he was afraid you'd flee like a wild deer if he moved too fast. You stepped closer as well, which seemed to give Tom the permission he was looking for. Within seconds, his mouth was on yours, his hands cupping your face, all tongue and teeth. There was hunger and desperation in the kiss, but it was hypnotizing, beckoning you deeper and deeper. He was almost doubled over to reach you (god, he was tall), so you shifted your weight to stand on your tiptoes.
Tom broke the kiss, leaving you with a confused look on your face.
He shed his suit jacket, throwing it carelessly on the floor. Next, he rolled up the sleeves of his shirt to his elbows. Tugging on the length of his tie, he loosened it enough to undo a few buttons at his collar, revealing an inviting expanse of chest hair.
“Turn around,” he told you, snapping you out of your male-stripper-fantasy gaze.
You did as he said, something in his tone going straight to your core. You felt him run his hands from your shoulders down your arms, then down your hips and up to your waist, the action bunching up the fabric of your dress. He moved your hair to the side, pressing hot kisses to your neck that made your eyes roll back.
“Can I take this off?” He whispered, his lips trailing up to your ear.
You nodded in response, trembling momentarily under his touch. Tom unzipped your dress, helping you push it down your body and step out of it. He unhooked the back of your bra without moving further. It occurred to you then how wrong this was, to be sleeping with someone else’s husband in their own bedroom, but to your surprise, you didn’t care. The only thing you cared about was the heat of Tom’s gaze on your bare back. You took your bra off the rest of the way and discarded it on the ground next to your dress. Once in only your underwear, you turned back around to face him, watching his eyes follow every curve of your body to drink in the newly exposed skin.
“Wow,” he said, simply, reaching out to grab you by the hips and pull you closer to him. “You’re gorgeous.”
Grinning, you stood on your tiptoes to kiss him again, cradling his face in your hands. You felt him smile back into your kiss. Before you knew it, he had you pressed against the wall, totally enclosed by his larger form. He went from kissing you on your lips to your neck to behind your ear to your chest, as if he couldn't decide which spot deserved the most attention or for how long.
One of his hands slid down to the waistband of your underwear, the cold metal of his wedding ring a shock against your hot skin. You made eye contact with him as his hand slipped between the fabric and your skin cup your cunt, whining when you felt his touch. He seemed to get off on that, capturing you in a kiss again at the same time he slipped a digit into your wet heat. You were too hot; you pressed your hand to his chest to stabilize yourself and pushed your underwear down your legs and kicked them off. Tom smiled at this, getting right back to pumping his finger in and out at a pace that almost made you melt down the wall.
It was probably a power trip thing, you thought, you totally naked and him almost fully clothed. You didn't mind because it was kinda hot, but it wasn't what you had expected from Tom based on the unassuming, Midwestern image of him that was circulated in columns and by the Roys themselves. But, then again, you hadn't expected to find yourself in this position at all when you left your apartment earlier that night.
The pace of his fingers felt so good, so intoxicating, that now that you had him, you needed more of him.
“A-another one,” you whined between kisses.
When you opened your eyes to look at him, Tom had a smug look on his face. Sure, it was arrogant, but it turned you on, so who really cared? “Yeah?” he asked, “You want another one?”
“Tom,” you hissed, gripping onto his shoulder as his finger curled in just the right way that it made your legs go numb.
The look remained on his face, but he added another finger nonetheless. Tom appeared to inhabit both extremes when it came to sex: he really wanted to pleasure you but he also really wanted to do what he wanted. Luckily, those two wants aligned.
He was making you feel so good that you needed to have more of him. Your kisses got sloppier, each so desperate to be further molded with one another that your tongues tried to push impossibly further into the other’s. Tom shifted his hand so he could angle his thumb to rub slow, tantalizing circles on your clit as he continued to pump his fingers. Your grip on his shoulder tightened–you feared your fingernails would leave dents in his skin–but like so many other things tonight, you couldn’t bring yourself to care. You could feel the pressure rising in your middle, your cunt clenching around his fingers in anticipation of your impending orgasm, but then it stopped.
You opened your eyes that you hadn't realized were squeezed shut to look at Tom, who had his hand in front of your face, fingers glistening with your slick. “Open,” he encouraged. You obeyed, accepting his fingers into your mouth and licking them clean with a ‘pop.’ He stared at you like you had hung the stars in the sky. He jerked his head toward the bed. “Sit.”
There was authority in his commands, but you didn’t fear him; from the short amount of time you had spent with him, you knew he was at his core a sweet man. You would admit to yourself that you had been curious how his awkward, nervous energy would translate into the bedroom, but once alone, he seemed to be a different man.
You watched him strip off the rest of his clothes eagerly, smiling up at him once he rejoined you on the bed totally naked. He must’ve noticed you staring, because he asked: “Do you want me to put on a condom?”
You shrugged, shifting your eyes back up to his own. “No, it’s okay. I'm on birth control.”
He sighed in relief. “Good. I don't even know if I have one in here.”
“Then why’d you ask?” You laughed, encouraged by the smile that crossed his face when you did so.
“Seemed like the gentlemanly thing to do. If you said yes, I would’ve sent someone to go get one or borrowed one from–”
“Tom?”
“Yeah?”
“Just fuck me already.”
“Alright. If you say so,” he teased, leaning down over you to kiss you. Both your lips were red and puffy from all the kissing and some biting, but it didn’t matter. You could feel his cock pushing against your stomach from the angle, so you reached down to take him in your hand and pump his length.
“Fuck,” he murmured against your skin, face buried in your neck as he pressed kisses to the every inch of available flesh, “Fuck…Can I?”
“Please,” you responded, noticing a little desperate hitch in your voice that you ignored. Tom licked his hand and cupped your sex with it, running the pads of his middle fingers through your folds a few times to collect the wetness between your legs. Gently, he guided his length into your opening
inch by inch, watching your face for any sign of discomfort before bottoming out.
You should’ve expected his dick to be big from his height, the size of his hands, his nose, whatever, but you hadn’t considered just how big. It was quite a stretch to take him fully, but he gave you all the time you needed to adjust and get comfortable. When you were ready, you bucked your hips up into his to give him the okay.
Tom took your permission to move and ran with it, grabbing your left leg and placing it over his shoulder before pressing you down further into the mattress with his body weight so he could thrust into you at a deeper angle.
You lifted your head to meet him to return to making out, the sensation of his tongue down your throat even more erotic now that he was inside of you, as well.
His thrusts were deep but not as aggressive as he had been with his fingers. He wouldn’t vocalize this, or even admit to himself that he was thinking this, but he wanted this to last. As much as it was supposed to be a hookup–emotionless sex–he found himself wanting it to happen again, despite his attempts to push those thoughts deep into the recesses of his mind.
One arm was thrown around Tom’s neck, hand gripping a fistful of his hair. Your other hand went down to your clit, beginning to rub circles to match the pace of his thrusts.
“You wanna cum again?” He teased, “Again, when I haven't cum once?”
You narrowed your eyes at him, playfully, slipping your finger down from your clit to lightly stroke the length of his cock that wasn't fully inside of you.
He let out a moan, eyes twinkling as he snapped his hips a little harder, snickering when you gasped in response.
Tom caught you in another kiss, resting his weight on his forearm that was positioned next to your head. You arched your back up into him, urging him deeper, which he obliged. “Touch yourself,” he said, disconnecting his mouth from yours just long enough to give the command.
You smiled into his lips, rubbing your clit again as his thrusts became sloppier and jerkier. He was holding on until you came again, despite his earlier cockiness. The moment he felt your walls tighten around him, he let go, spilling inside of you with a grunt.
He pulled out, rolling off of you to lay beside you.
Tom was still catching his breath, and you watched his chest heave for a few moments. “Hey, you okay?” He asked. “Everything alright?”
You smiled, nodding and reaching over to kiss him again. “I'm good, yeah. You?”
“Perfect, actually.” Tom smiled back at you. He found himself lost in the moment, lost in your eyes, lost in the connection you two had just had, and it was too much for him. Quickly, he sat up, ready to change the subject. “You need to clean up?”
You furrowed your brow at the sudden shift in his demeanor, but going along with it nonetheless. Despite him just having been inside you, you didn't feel like it was your place to mention the change. “Yeah. Can I?” You asked, gesturing vaguely toward the bathroom.
“Yeah. Oh, yeah. Go ahead. Towels are above the sink.”
You flung your legs over the side of the bed and stood, heading toward the bathroom. “I’ll just clean off real quick, then I’ll be out of your hair.”
“No, no, no. I mean, you can stay the night. If you’d like, that is. I could call you a car, though, if I’ve made some awful faux pas and you don’t want to look at me for another–”
“Tom.” He focused on you again after his brief spiral. “I would like to stay.”
He grinned. “Great, that's great.”
“Just let me–” You waved your hands around your lower body, “–clean all this up.”
“Yeah, of course, sure. I’ll be here.” He added the last part in a quasi-sing-song voice.
At the sound of the shower turning on, Tom rose to locate his clothes and try to clean up. He pulled his boxers back on, taking his dress shirt, pants, & jacket to be thrown into the hamper. They really should be dry-cleaned, he considered, but found that he couldn’t be bothered. As for your clothes, he wasn’t sure what exactly to do with them, so he laid your dress across a chair in the bedroom and left your bra and underwear on the floor. He was still considering whether he should pick them up or not when you came out of the bathroom, towel wrapped around your torso.
Once you had dressed in your undergarments again and Tom had given you an undershirt to sleep in, you started to wonder what all this meant. If it had just been a hookup, why were you staying the night? You had thought you’d feel dirty and disgusted with yourself, spending the night in someone else’s bed with someone else’s husband, but you didn’t. You didn’t know what that said about you, what it meant that you were perfectly comfortable talking into the night with Tom, both laughing and sharing stories long after you had agreed to turn the lights off and get some sleep. That almost made it worse, you thought, that it wasn’t just sex. That made it dangerous.
After you had drifted off, Tom spent a few minutes watching you sleep. He tucked a stray hair behind your ear, watching the worries of the day wash off your face while you slept. He knew it was wrong to be more comfortable in this bed with you than he was with his own wife. But that was something to deal with (or repress) in the morning. Here, now, with you wrapped in his and Shiv’s bedsheets, your form against his chest rising and falling with his breaths, he could pretend it was meant to be like this.
@swiftcession @greenwrldsz @zirrocom @lukas-matsson @ledtassoo @bluecruz97 @rita-lean @grainyimag3
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haderjr · 1 year
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gays work for waystar royco. real faggots work for nohobal enterprises!
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Text
I Can Take a Beating (Like a Good Pair of Headphones)
Pairing: Kendall Roy x Reader
Rating: T, shockingly
Notes: Hey look it's that Kendall Valentine's oneshot I mentioned. Title from the Walk the Moon song Headphones. Written today and not beta-read, shocker, I know. also lolololol posted it to the wrong account the first time
Warnings: Cursing; Roman being a little shit; mostly fluff; potential power imbalance
Summary: This is where Kendall feels a little…Conflicted. He could hold out for whenever your birthday is, but your headphones seem to be on their last legs. And if he’s being totally honest, he’s been considering asking you out. Valentine’s is just a few days away. He could…Give them to you, ask you for a drink then? Or would you feel obligated because he’s the boss and he’s giving you a gift? 
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GIF by jeremystrongs
He sort of admires your loyalty to your old pair. You’ve clearly had them for longer than they’re meant to be kept. You use them every time you're listening in on a meeting, or if you're head-down to get some work done. When you're finished, you always lift the headphones off of your ears with tender reverence, setting them aside and plugging them in to charge immediately (for as long as you must’ve had them, he’s certain the battery must be on its last legs). Then you always reach up, brushing little black flecks of flaked padding away from your ears before you duck your head back, inspecting your collar and shoulders for any little bits that may have escaped your notice. 
 Look, he gets it. Kendall’s a headphone guy.
He’s ready, willing, and able to discuss the merits of Meze, Denons, Bowers & Wilkins, Sweetwaters. He has more pairs than he can count, more pairs than he cares to think about. And maybe that’s why he does this himself, instead of asking Jess to handle it. It becomes a bit of a pet-project. He puts more time into it than he’d care to admit. He has a goddamn spreadsheet to compare each of the models he’s considering getting you based on the music he’s heard you discuss. 
He has Roman do some snooping. It’s not a hardship. You’re one of the few people at Waystar Royco that Roman can stand. Kendall has to barter a couple of assignments and a future favor for it, but it’s worth it. Roman gets a breakdown of what you like to listen to, a full array—music, podcasts, audiobooks, streaming services that you prefer to use. And for the minor tooth-pulling it took to get his brother to agree, Kendall’s got to hand it to Roman. He got all of the dirt that Kendall needed to make a decision. 
Kendall winds up having a pair custom made. The headband has a subtle diamond pattern, using two of the colors he sees you wearing often. The earpads are thick and cushy, and certain not to flake any time soon. He makes sure to have a headphone jack included, just in case, you know. He wants to give you options. 
But this is where Kendall feels a little…Conflicted. He could hold out for whenever your birthday is, but your headphones seem to be on their last legs. And if he’s being totally honest, he’s been considering asking you out. Valentine’s is just a few days away. He could…Give them to you, ask you for a drink then? Or would you feel obligated because he’s the boss and he’s giving you a gift? 
He’ll have them delivered to your desk, that’s what he’ll do. He’ll gauge your reaction, see how you like them, work it out from there. 
--  
“Roman! Is this why you were asking me all of those questions about what I listen to?” 
“Well, you know," His brother gives a lame shrug, eyes wandering the package on your desk.
“This is so sweet of you, you didn’t have to do this!” 
Kendall’s heart drops from his mouth to his stomach. He can’t do anything but watch as you rest your new custom headphones back down in the box and throw your arms around Roman’s shoulders with a gleeful grin. Kendall blinks dumbly as Roman reluctantly raises his arms and gives your sides a pat. 
Roman just shrugs. “Maybe now that black shit from your other pair will stop getting all over the fuckin’ place.” 
You’re laughing. You’re laughing at Roman and you’re hugging him. It’s not right. That’s supposed to be Kendall’s laugh, and Kendall’s hug. Kendall swallows roughly, turning from the two of them as Jess warns him that he has a meeting in three. 
“Uh—Yeah. Yeah, thanks,” He nods. He chances one last glance at you. He takes in the way you draw back from Roman, picking up the headphones. He sees you smooth your fingers over the diamond patterning, and the earpads. You look so goddamn happy. It makes him feel so goddamn happy. 
It’s almost enough to quash his urge to ask Roman what the fuck he was thinking. 
--  
“What the fuck were you thinking?” 
“What? Dude,” Roman frowns as Kendall leans into his space, cornering him before either can leave the conference room. “Did you have falafel for lunch? I’m getting garlic.”
“You know you didn’t send her those fucking headphones,” Kendall spits. 
“No, but who cares? I did all the research, right?” 
“You asked her some questions. I did the research.” 
Roman rolls his eyes, glancing back in your direction. Kendall looks over Roman’s shoulder, peering through the glass wall to where you’re sitting at your desk. You’re using your new headphones. Every now and again, your fingers raise to brush over the band, or over the outside of the pads. Each time, your smile widens before you force yourself to refocus. 
“You want me to go tell her?” Roman offers. 
“No. No, you have done more than enough.” 
Roman smirks, holding his hands up in mock surrender before miming zipping his lips shut. Kendall puffs irritatedly as he draws back from Roman, meeting Jess at the door. 
“What’s next?” He asks, eyes set on you as he walks down the hall. Jess rattles off his next few meetings, appointments, a note that he still hasn’t RSVP’d to Shiv and Tom’s for their Valentine’s dinner (or Valentinner as Tom had called it when he reminded Kendall of it that morning). Kendall considers for a moment. If he had a date for Valentine’s, Tom would probably get off his back about going to that stupid thing (then again, probably not. It would likely be met with a hearty congratulations and an urging to bring them along, no matter how premature the meet-the-family stage would be. Then again, you already know most of Kendall’s family—but still, he wants to take you to dinner, not into the lion's den). 
“Okay…Okay. I’ve got,” He shakes his sleeve back from his wrist, “What, half an hour free?” 
“Yep,” Jess nods. 
“Okay. I’ll uh…I’ll meet you back at my office. Thanks.” 
He stops as Jess goes on, and watches you across the office again. He can’t tell at this distance, but are you…Listening in on a meeting? Or are you focused up? He doesn’t want to interrupt your flow. He had those headphones specifically noise-cancelling so that nothing would interrupt your flow. He glances toward his office, then back over to you. He can just…Look, right? He can look over your shoulder from like a desk back, see what the hell you’re working on and make a judgment call. Yeah. Yeah, that’ll do it. Kendall moves carefully, desperately trying not to look at anyone as he walks through the office (though he fails and subsequently gives a quick smile, a mutter of, “Hi,” when he meets the odd person’s eye). 
He gets a couple of feet behind you and tips his chin up a touch, eyeing your screen over your shoulder. Email. He’s seeing email. Email opening, email closing, email being archived, so nothing too…Involved, probably. 
Kendall can still turn away from this. He can still turn around, and let it go. And then you tip your head forward, your fingers brushing over the band. He can see the reflection of your smile on your laptop screen, and—Yeah, damnit. He’s gonna do this. He’s not letting this go. 
--  
You glance up at the vibration of knuckles wrapping against your desk. You glance to them, then up at the person knocking. You do a double-take at the sight of Kendall standing in front of your desk. You grin, sliding your headphones off of your ears. 
“Hey!” 
“Hi,” Kendall smiles, his eyes dropping to where you’re still grasping your headphones. “You busy? You wanna go grab some coffee?” 
“Yeah! Yeah, sure,” You nod, looking down at your laptop. “Just lemme me, um…” You finish off an email and pause your music before you carefully slip your headphones off. You raise your hands to your ears, absently dusting at your ears, though there’s no reason for you to. The pads of your new headphones are pristine, and uncracked. You stand, pulling your jacket on and rounding the desk to join Kendall. 
-- 
“How’s, uh…How’s your morning going?” He asks. The two of you are pressed pretty close in the crowded waiting area of the Starbucks, waiting for your drinks.
“It’s been pretty nice, actually. Not completely crammed with meetings—and I had a really unexpected gift on my desk this morning.”
“Oh yeah?” 
“Mhm! I mean, I had a little, uh…A suspicion when Roman asked me about all of the stuff I listen to.” 
“Really.” 
“Yeah. How’s yours been?” 
“It’s uh, it’s, uh…” Kendall trails off, looking around. “Been kind of a mixed bag.” 
“Really?” You shift from foot to foot, fingers accidentally brushing against Kendall's. “What’s going on, everything okay?” 
“Things are fine, but I have to,” He clears his throat. “I have to tell you something.” 
“Okay,” You nod. Kendall looks like he’s trying to bring something up and hold it back all at once. His lips are pursed into a thin line, his brow furrowed. You tip your head to the side a little, raising your brows. “What’s going on?” You press softly.
“The truth is…” He seems to weigh his words for a moment before he meets your eye. You’re stunned by the way he watches you—with a nervous smile on his lips. 
“Those headphones, um…They weren’t from Roman.” 
Your chest flutters with nerves and butterflies as it sinks in. “They were from you?” 
“Yeah.” 
“Why did Roman let me think that they were from him?” 
“Because he’s a shithead. I mean he’s my brother, I love him, but he likes to do things that get under my skin.” 
“He seems good at it.” 
“Oh, he’s an expert,” Kendall chuckles softly. “But I, uh…you know, you work really hard, and you clearly, like, love your headphones, so I just wanted you to have some good ones.” 
“Good ones? Kendall, you got me, like, the 24-karat gold of headphones.” 
“I mean, yeah. Yeah but you’ve earned them—” He goes quiet as you dart in, curling your arms around him before you can think to stop yourself. You didn’t hesitate like this when you went to hug Roman, but Roman is different. You have a far more casual relationship with Roman. You and Kendall, well. There’s always been this feeling pulling you toward him, but with this revelation and this gift, it’s grown stronger. Kendall’s hands rest hesitantly on your back before he draws you into his chest a bit more. You grin, turning and pressing your face into his shoulder. 
The two of you let go as you hear your orders called. You turn, smiling as he passes you yours. 
“Thank you,” You smile, and repeat it as he opens the door for you. The two of you take meandering steps back toward the office, keeping close enough for your arms to brush as you go. 
“I uh…I actually wanted to ask you something,” Kendall adds. 
“Oh?” 
“Yeah, I know, uh…I mean, I’ve been meaning to do this for a while. Not the headphones thing, but this other thing—And I don’t want the headphones thing to effect this other thing.”
“Okay.” 
The two of you come to a stop at a crosswalk, watching cars zip by as you wait to cross. 
“What is it?” You press. Kendall’s gaze sweeps your face before he looks down at his coffee cup. 
That guarded gaze is back. “I wanted to know if you’d be interested in grabbing dinner, or a drink sometime. Something, you know.” 
Your brows raise, your smile widening as you nod. 
“Yes, I would.” 
“I mean, it doesn’t have to be a big thing—”
“Right—” 
“—But I would like to get to know you better, and I’d really, um—I mean it when I said that I don’t want the headphones to uh, to influence—” 
Kendall goes quiet as you lean in, pressing a kiss to his cheek. He blinks at you in surprise, and you grin as you draw away. 
“I’m up for dinner, or drinks, or…Whatever,” You insist. 
“This is going to sound cliché and stupid, but are you busy this Valentine’s?” 
“I am not…On one condition.” 
“Okay, yeah. What is it?” 
“We don’t go to that Valentine’s dinner….Thing that Tom’s doing.” 
Kendall smiles widely, shaking his head. “I would never put you through that, trust me.” 
“Okay,” You laugh, “Then yes, let’s um…Yeah. Let’s.” 
--  
Kendall doesn’t walk you back to your desk—he’s got his own meeting to get to. But you feel him watching you as you settle down at your desk, unlocking your laptop and picking your headphones up. You glance up his gaze, smiling and winking as he catches your gaze. You bite back a giggle as he grins and turns hurriedly, nearly walking into a wall as he goes. You dip your head, pressing play and forcing yourself to refocus on your work. 
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vclvetfleur · 10 months
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Obedient Chapter 1
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roman roy x fem! reader
Summary: After college you hadn't been able to land a job. You hadn't even been able to book a single interview. After spending a night with your old college roommate, you see how lavish her life has been after becoming Kendall Roy's assistant. After a long night of helping her move in, she offers to help you out. She unsure of what exactly she might be getting you into with getting you an interview at Waystar Royco. But it was better than being unemployed.
Warnings: Degrading and implied drug abuse
Word Count : 3.6k
Notes: AHHHH I finally wrote a chapter. I hope you guys enjoy it!
Chapter 1: The meeting
You laid flat on the new couch your college friend had gotten. “Jess, Jesus fuck, when is this thing coming?” you whined, shooting back up to look her way with a pouty lip. She had been bent under her television to figure out how to exactly plug in her Amazon TV stick. Jess’ new job had afforded her the luxury of not just a new couch, but a new television, new coffee table, new bed and a brand new apartment. If you could even call this place an apartment. It was giant. Jess truly got lucky, at least that’s what you always thought. You had to be lucky if you saw how Jess and you were back in college, stealing and flirting your way just to feed yourselves or feed into your lifestyles. You had even convinced a man to pay for your wardrobe once.
“I don’t know, I’m not the tracker now am I?” she spewed out in annoyed tone. “Can you just help me? Shine a light or something.”
You hopped off the couch and grabbed your phone from the glass top coffee table. You waddled over and turned the flash on. After watching the few attempts of her trying to squeeze her hand into the right angle of the HDMI bit, your anxiousness reached a level of annoyance.
“Just let me.” You huffed before grabbing it and tilting your head to attempt to do what she had, failing just the same.
“I told you! It’s fucking impossible.” She laughed.
“You should’ve done this before hooking up the tv.”
“Oh wow, cause I really thought plugging this in was going to be so hard. Shut up.”
“AHH!” You shouted in excitement. You hopped up and down and revealed your hand from under the tv and clapped your hands together with the phone in-between them as the flash shined on the wall. “I did it! I did it!” You giggled. You pulled the cable down and plugged it into the outlet before rushing back to the couch. You grabbed the remote and turned the television on. You continued to gloat on your achievement.
“Yeah yeah, enough. Let me see when the pizzas almost here.” She grabbed her own phone, swiping through it to find the time estimate.
Ding. Ding. Ding.
Her phone was constantly buzzing. “Is that the pizza? Is the driver lost?” You questioned. Jess’ face had dropped a while ago. Ever since she had picked her phone up. It was her boss. She absolutely despised the job. That wasn’t true. She didn’t despise it. She was just constantly worried. She was constantly worrying about her boss, Kendall Roy. She was his assistance. And he never understood the boundaries of the job.
“No, it’s just work.” Her lip twitched on the side to show some kind of pity. But pity for who? Kendall? Was he in some kind of issue again? Or for you? For ruining the night. “Just ignore it” You shrugged.
“That’s why you’re unemployed” She joked. Your jaw dropped as your hand fell on top of your chest as if you’ve been shot. “Ouch” You said sarcastically.
“No, no I’m sorry. It’s just, I just don’t think you’d understand.” She quickly tried to recover. But she was right. You didn’t understand. You don’t understand what Jess’ job really consisted of. She had a lot to deal with. While you, regardless of being unemployed, you didn’t have to go score drugs for your ex drug addicted billionaire boss. You had just graduated college, same with Jess, but you thought Jess was lucky. She just left college and she was already involved in such a high profile, high paying job. She went from a dorm room to a studio in Brooklyn to a 2 bedroom penthouse in Manhattan because it was a fasted commute to her job. And because her job could afford for her to even pay for it.  While you couldn’t even land an interview. You were just hopping from one job listing to the next. But thankfully you did have a fund to help you pay for your way for just a couple more months.
Jess found this job in the oddest way. You actually met up with her the night after it happened. She had been working for a restaurant when she met the Roy’s. And Kendall had just fired his assistant over the restaurant they were just sitting at for ruining the dinner reservations. Apparently, the place and time really mattered to the investors that much. So, while she waited on their table, Kendall asked her if she would want to work for him. It was ridiculous, sure, but she was the only one trying to not make a scene with him around since everyone working was staring, except her.
It was impulsive, but hey, look at her now.
“Uh, the pizza’s gonna- uh- be here in like 6 minutes.” She felt guilty. She knew it was out of reach, but Kendall would not stop bothering her with text after text. She thinks he might be out drinking again because his texts sound irrational. This was right after the huge blow out with his father, which was very public. And everyone watched as he came to crawl back and basically publicly beg for daddy’s attention back with that pitiful interview he gave. “Hey seriously- I’m sorry- that was super uncool. It’s just- Kendall is not really that well put as he seems.”
“No, It’s fine Jess. Seriously. You have lavish job with a psycho boss.” You tried to joke it off. You weren’t annoyed about the joke, just the constant apologizing. Jess wasn’t usually the one to really apologize so excessively. But her job really changed her. She was so much more nervous and shakier. As if anything she said could be used against her, even if it was a joke.
“I didn’t mean-“ You cut her off.
“Let’s just watch tv. What was the movie you wanted to watch tonight?” You tried to remove the subject from the air. It wasn’t a great feeling knowing your friend pitied you. Despite the awkwardness you tried to keep a grin on. You didn’t get fazed much. It didn’t take a lot to hurt your feelings. You’ve heard worse and meaner things before. You were scattering to move things you’ve just placed on the table for some room for the pizza when it finally gets here. You got up and went to her fridge before turning your head back to Jess quickly.
“My place might be hiring” She blurted out. She didn’t mean to. There weren’t really any other assistant positions. Shiv doesn’t work there. Her husband Tom had his own little assistant, Greg. Logan had way too many to even count. And Kendall wasn’t that trusting despite the restaurant ordeal. Except maybe Roman. “I’ll ask!”
But those words were the 5 words you heard nearly every week for weeks now. It was an exhausting thing to hear.
Your shoulders dropped down as you watched her frantically type on the keyboard. You don’t know exactly what she was saying, but whatever it was, it was a lot.
“Dude, I’ll be fine, don’t ev-��� You started before Jess put a hand up. “No. Don’t.” She persisted. Was this a mistake? Yes. Will she regret it? Possibly. She didn’t want to give you off to the lions, but god the money was so good.Jess was being paid 16k. A month, with a bonus here and there. Just to listen to Kendall whine and ask her to run around. Sure was it a lot of work and stressful? Yes, but she knew you could probably handle it. Plus you’ve met Kendall before from time to time. He seemed normal enough.
She put her phone down and finally paid you attention. “Okay, done. Now let me search the movie up.”
You both spent the rest of the night just drinking and eating pizza throughout the movie. With little jokes being told to each other here and there. But it got late and you decided to go home.
You spent the next couple of days on your laptop as you were doing what you did best, ignoring all your issues. You see a notification pop up on the corner. Jess texted you. You clicked on the text.
‘i got you an interview!!!! tomorrow 1pm.’
‘Kendall said he figured it out for you!’
You went completely pale. You didn’t think it was possible. Finally. You finally got an interview. And you didn’t even have to put in a resume or a super fucking cover letter. You could not express the happiness you felt. You texted Jess back immediately.
The next morning you got up early. You were way too excited to sleep throughout the entire morning. It was just how your brain worked, I guess.
You spent this time to get ready. You wanted to leave an impression. This was a multi-billion dollar company filled with millionaires and billionaires. You couldn’t stand out. Thankfully, you had an outfit saved for an interview. It wasn’t anything lavish, but it looked nice. You set it on your bed and went into the bathroom to take a shower. You made sure to scrub down your body as hard as possible. Your mind constantly reminded you of the people there. You made sure you smelt as though you had just run through a field full of every type of flower to ever exist. Or as if you had put yourself in the washing machine a dozen times. Whatever sounded cleaner.
You sat on top of your bathroom counter as you blow dried your hair. You tried to get every single bit of hair to look as perfectly placed as possible.
You went through your make up and then started the rest of your day. You sat at your bed with coffee and a piece of toast with almond butter on top of it as you watched tv before you had to leave. Specifically, you watched ATN. You needed to be in that mindset.
Once you finished your breakfast, you got dressed, sprayed on deodorant and perfume and decided it was time to go. Your nerves were through the roof. You checked the time. 11:30. You undid the caps of your medicine and took them with the last bit of coffee you had in your cup.
Unfortunately for you, childhood trauma left you with a lot of crazy pills you needed to take in the morning and night.
You left your apartment and walked down to the train. The ride was agonizing as you waited for each stop. You left the station once you hit your stop Cortland Street. You walked down a few blocked before hitting the building. You stared up at it as you couldn’t believe this is where you were possibly going to start working. You watched men in nice fitted suits that probably costed two times what you pay monthly for your studio. You shook of your nerves and walked into the lobby and then up to the receptionist.
“Uh- hi, I’m here for an interview.” You tried not to stumble on your words.
“Name.” She sounded unamused. She barely gave you a look. She seemed as though she had no intention to either. You gave her your name as she tried to search you up. She finally looked up from her screen and pointed at the turnstile. “Floor 52”
You nodded and walked through and to the elevators. You stepped in as you hit the button. 60 floors? Seemed excessive.
You watched as the numbers lit up as we passed each floor. Each floor just caused more and more anxiety in you. You didn’t know if you had it in you to even work in a place like this. What if you did bad at in the interview? Oh god, did you forget your resume? You panicked. You opened your bag for the millionth time since leaving the apartment to check for the folder again. You had a constant anxiety about losing things. You probably checked if you lost your phone or key about 10 times while on the walk from your apartment to the subway. And then some more.
The elevator dings and the silver doors open to reveal offices. You stepped out to only see walls and walls of just glass. Seemed redundant for an office if they could hear and see you, but okay. People passed through with papers or phones in their hand as they were trying to keep their heads low enough to get unnoticed. You walked around before seeing Jess with Kendall. She grins big before sending you a wave and then a gesture telling you to come over.
You obliged and headed towards her. “Hi!” you greeted before reaching to give her a hug.
“Kendall. You remember y/n? She’s here for the interview.” Jess grinned.
“Of course. Uh- ya. Uh-so, he’s not really here right now. He’s uh- fucking idiot- he’s late to his own fucking interview for his own assistant.” Kendall seemed to be annoyed as he was looking around. “Fucking idiot. I told that-“ He stopped himself as he tried to breathe through his annoyance. Jess’ head shot from you to him as her face dropped. She was left with the impression that Kendall maybe needed another intern. Logan couldn’t possibly need another one. Tom had Greg and seemed contempt.
“Oh, my interview isn’t with you?” You sounded confused, trying to sound as polite as you should be right now in this moment .
“No-uh you’re interviewing for Roman’s assistant.” He informed you quickly. Jess looked at you with bulged eyes. She seemed to have no clue about this. You had looked at her with a moment of confusion of why she seemed so worried. He said it as if it was not a huge deal. But for Jess, she knew she wouldn’t ever set this up if she knew it was for Roman.
“That’s fine, I can wait for him.”
“No, you shouldn’t. Let me just call him.” Kendall tried to cover up his own brothers mistakes. He walked away before checking his phone and putting it up to his own ear. “Uh-why don’t you just get a coffee or a snack in the break room til he gets here” he whisper spoke as he held her hand over the phone speaker.
Kendall seemed sweet and considerate. I don’t understand why Jess had such an issue dealing with him honestly. He didn’t seem bad. Maybe nicer than what I’ve seen of the other members on the board honestly. Those interviews, gosh. They were absolute messes. Kendall was a mess sure, but at least he shows a bit of remorse.
Before you could expect it, which honestly, unless you had even heard about Roman, no one knew what to expect from him other than utter chaos and dumbass bullshit. The elevators dinged and revealed who your interviewer was.
Wow. What an entrance.
“Alright cock licker, I’m finally here.” He announced to the entire floor. People’s heads barely even moved.
A short man with a stripped, what you can only think of was designer, dress shirt with a navy blue suit and enough gel in his hair to glue back the titanic together waltzed in. He walked through as if he basically owned the company as if he was THE Logan Roy himself.
Kendall power walked towards him. “You’re late to your own interview for your own fucking assistant dipshit.”
“Relax, I was busy paying the homeless people on the subway to fight” He smirked, waiting for a reaction.
“Yeah like you’d ever even been down that filthy rat hole.” Kendall scoffed.
Oh wow. Maybe he was as bad as Jess made him seem. I guess he liked to play Social Justice Warrior whenever he liked to.
“Yeah okay, where are they then? I’m ready for a black coffee.” Roman shoved past Kendall before finally laying his eyes on you. He would way it was cause he didn’t recognize you, but he barely even recognized people within a 20 feet radius of his own office. “Okay yea, come to my office I guess.” He spoke to you. He turned around and put his hand up, motioning you to follow him. Almost like how you would with a dog.
You nodded and followed before looking at jess with a look that could only be described by ‘what the fuck did you get me into?’
“Sit.” He ordered before plopping down on his leather chair in front of his desk. He laid back before finally feeling adjusted and looking up at you.
His eyes met yours before you immediately shifted them away from his. You grabbed a folder out of your duffle bag as you were ready to get your paperwork out before being interrupted.
“What the fuck are you doing? Are you turning in your fucking homework or something? Oh god you were that kinda kid huh? The one to remind the teacher of homework. God. Ew. No I cannot have that. Put that shit away.” He sure was pushy. Was he trying to upset you so you’d leave? What was the point of being a dick?
“Uhh sorry I just thought you wanted to see my resume or something” You shrugged. You tried to keep a calm composure. You needed this. I guess you can handle this kind of abuse for a bit. Maybe just until you had enough. Which you were pretty sure you’d make enough.
“Uhh” he mocked “No I don’t need to see that. You’re an assistant not whatever the fuck these other people do.” He gestured to everyone outside. You looked out and saw Kendall and Jess shooting glances at you. They knew what they had just out you up to. Jess feeling worse about it than Kendall did. You bit the inside of your own cheek to keep yourself from saying whatever you wanted to actually say.
“My bad.” You quicky apologized. “So, what questions are you gonna ask me then?”
“Uhh can you run to get me coffee?” He prompted.
“Now?” You shot him a confused, but annoyed look.
“Yeah. I’m hiring an assistant. Not a hooker. I would like if you dressed like one though. But I can’t hire someone who can’t do something simple like buy fucking medium whole milk latte.” Okay wow he was really annoying.
“Yeah, I can order coffee.” You said blankly.
“Good, go get one for me across the street.” He shooed you with his hand.
“Now?”
“No shit. Ugh I thought having an assistant wasn’t gonna require training. Do I need to keep dog treats in here to reward you? You’re not gonna piss on the floor, right? You don’t need that much training.” He tried to stop himself from giggling at his own jokes. He stood up before pulling his wallet out of his back pocket. He flipped it open and pulled out a $50. He handed it over to you and sat back down.
You stood there with the money, confused. “You really want me to do that? Right now?” You questioned again.
“Goooooood. Yes. This counts for your interview so you know, get to it or whatever the fuck.” He shooed before going onto his phone.
You nodded quietly before leaving the office. I guess you had to go get him what he asked for. God what a major fucking douchebag. I mean you’ve seen how he’s acted over social media and tv, but never did you think he was this bad.
Jess rushed over to you. “Y/n Oh my god, I’m so sorry I didn’t know. I thought Kendall just meant he was gonna get another assistant” She frantically explained.
“Its fine Jess. I guess I gotta get the oily weasel a fucking latte.” You scoffed. You held her arm to reassure her you were okay and not annoyed with her. She couldn’t of known.
“What? That’s what he said?” She tried to rationalize what Roman even asked for. You nodded before getting in the elevator. Jess almost walked in before hearing Roman from his office. “Hey! Come on, this isn’t a two people job now!” You rolled your eyes and hit the L button.
You quickly made your coffee run, making sure to get something for yourself, since you guess he was paying for it. You grabbed your matcha and his latte before heading back to the office. You walked in before setting down the cup and money on his desk.
“Ooooh what’s that? You go through rehab too? My brother drinks that shit.” He continued to try to strike as many nerves as he can. He really had a big mouth. It almost as if he let every intrusive thought that came to mind out.
You sat back down before taking a sip of your own drink. “Nope. So what else are you gonna ask or are you gonna make me do more embarrassing shit for free?” You finally let your annoyance out. You might regret it, but fucking hell, you could not spend the afternoon being someone’s little errand boy with no compensation.
“You’re already hired. Ya just send it whatever the fuck you need. I don’t know, ask Jess how to do all that shit, but ya I guess this latte is fine enough.” He hid his smile before taking a sip from the latte you gotten him.
You sat up a bit straight as you set your drink down. “That’s it?”
He nodded before furrowing his eyebrows at you. “Ya. What?”
“I just expect to-“  Roman quicky cut you off. You never liked being cut off. It was really one of your pet peeves. You couldn’t stand it. But I guess you needed to get use to it with this job now.  
“Just do whatever I ask you to, okay? You seem obedient enough.” He rolled his eyes before putting his feet up on his desk.
Notes: Next chapter is up!
Chapter 2
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Blurred Lines pt 1 (Kendall Roy x f!reader ~ 18+)
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Explicit ~ Minors DNI
Characters: Kendall Roy x female reader
Summary: you work with Kendall and he has an active fantasy about how your first time together will go
WC: 950
Warnings: smut, unprotected sex, masturbation, voyeurism if you squint maybe
A/N: I don't even know where this came idea came from 🤣. There's just not enough Kendall smut. Basically, the whole thing takes place in his head.
Part 2 here
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When Kendall Roy wanted something, nine times out of ten he got it. What you didn’t know, what no one knew, was that what he wanted right now, what he desired more than anything, was you.  
He had first noticed you a few months ago. You were a new hire at Waystar Royco, you had to be, he thought. Otherwise, he would have known about you. You were impossible to ignore. You commanded the room, even without speaking. People wanted to just be near you, to be in your orbit. 
He watched you for a while, observing you from the safety of his office. It wasn’t just your body he admired, although he did definitely like that - the way your skirts clung to all your curves and your blouses always had the top button undone, showing just a small hint of what was underneath. No, he also appreciated the little things about you that everyone else seemed to take for granted - the way you bit your bottom lip when you were really concentrating, the lilting laugh you had when someone told a joke, the way you held your head down and did your job but were also not afraid to stand up to the boys club you were surrounded with. 
You had spoken a few times, brief pleasantries or details for upcoming meetings, but not much more. He was technically your boss, and he was trying to control himself. 
Inevitably though, you became almost an obsession for him. Consuming his every thought, he found himself falling behind at work, completely unable to concentrate. Looking for hidden meaning in every smile you directed his way, he felt like a teenager with a crush. His only relief came when he was home alone at night, with just his mind and his hand. 
He had an entire scenario of how it would finally happen running through his head night after night: you would finally notice him, really notice him at work. Maybe after yet another long, boring presentation you both had suffered through. He would take you by the hand and lead you back to his office. Words wouldn’t be necessary. He would kiss you slowly, finally acting on all of the impulses he had held at bay for so long. 
Unzipping his pants, he began stroking himself, already hard just thinking about it.
You would respond to him hungrily, obviously feeling the same way about him. The kiss would deepen, all tongues and teeth and lust. You would moan his name and it would be the sweetest sound he had ever heard. His fingertips would ghost over the hem of your dress, then slowly move up the inside of your thighs, barely touching you, the promise of what was coming making you more wet than you had been in a very long time. 
Once his hand did reach your now-aching center, he would push aside your soaked panties and run his fingers through your slippery opening. He would have you backed against the wall for support, otherwise you might be on the floor from the feeling of his fingers curling inside you, repeatedly hitting all the right places. Taking his time, he would relish the look of absolute rapture on your face, knowing he was the cause of it. The noises you made would make him hard instantly. 
He would take off your dress and unhook your bra, his mouth finding your hardened nipples. You would arch your back, begging for relief. “Ken….Kendall…” you would gasp as he quickly undid his zipper. Wrapping your legs around him, in mere seconds he would be inside you, where he had wanted to be for so long. Buried to the hilt, he would fit perfectly, like you were made for each other. Who knew, maybe you were. Each perfectly paced thrust of his hips would bring you closer to the edge. 
He would then carry you over to his desk, pushing everything off into the floor and sitting you on top. Entering you again, the change in angle would have you groaning, pushing your hips hard against him, not able to get enough of him.
He put a hand against the wall and kept stroking himself, all these thoughts running through his head making his dick throb and pulse with need. 
He would move a hand down to circle your clit, making your legs shake, working your body closer to climax. When it did overtake you, you would rake your nails down his chest, digging in and leaving behind crescent moons that he would wear proudly, loving the thought or being marked as yours. 
Your name and a string of curses would fall from his lips as he came inside you. Afterward, he would hold you on the couch in his office, kissing your forehead and making sure you were okay, hoping this was just the first of endless encounters between you.  
He wanted to make you feel like he was the only man in the world, all you would ever need. The feeling of being inside you would be like heaven on earth. Even though he was a man who could afford to have anything he wanted, all he really wanted was for you to stay by his side, maybe forever. 
As this fantasy played itself out in his head, Kendall felt himself letting go, spilling his seed all over the Italian marble floor. He had to find a way to make this a reality. He couldn’t keep this up; he was driving himself crazy. How hard could it really be?
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616wilsons · 11 months
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call it what you want
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PAIRING stewy hosseini x roy!reader
PROMPT “why are you ignoring me?”
SUMMARY whenever stewy is at the office, he always stops by to say hello. but recently he has been walking right past you without saying a word. you’ve had enough.
TAGS @chaithetics @lukas-matsson @violentdelightsandviolentends
WARNINGS brief mention of drugs, fluff
WORD COUNT 3.1k
NOTES my first time ever writing an actual one shot! please go easy on me lol. if you would like to be added to my taglist please let me know! enjoy my loves 🩷
While you were the youngest Roy sibling, you still had an important role at Waystar Royco. You went into the office every day just like your brothers, Kendall and Roman. Your father had been grooming the three of you to be in the business for as long as you can remember. You were always more interested in the family business than your sister so you, Kendall, and Roman were the ones who were always in the office. You did a lot of what they did, go to board meetings, meet with investors and board members, organize offers on your father’s behalf, et cetera. Most of the board members would rather deal with you than your brothers and you took that seriously. So, when Stewy Hosseini suddenly ended up on Waystar’s board, your job got even more complicated.
You had known Stewy as long as he had known Kendall. They met in their first year of college, but you only met him in person when you were eighteen and they were twenty-three. As soon as you met him you were enamored. Not only was he one of the most attractive people you had ever seen, but he was also passionate and motivated, which were traits you looked for in relationships. You became good friends over the years, you knew he was always in your corner and vice versa. You crushed on him from afar, planning on never letting anyone know of your feelings. One, he was older than you, and two, he was Kendall’s best friend. He could only ever see you as Ken’s baby sister… right?
Fast forward to the present, Stewy was in the office more and more. You saw each other if there was a board meeting and always found time to talk. If he was visiting Ken, he would always stop by your office or find out where you were just to say hi. Always. Even if he just saw you the day before. He would end up staying for at least an hour because you both get caught up talking to one another. You always had great conversations with each other even if you didn’t always have similar interests. One day he was walking around with Roman at the office. To get to Roman’s office, they would have to pass yours. You saw them coming and anticipated Stewy, at least, smiling or waving. They just walked right past and entered Roman’s office. He’ll probably stop by after, you think and resume your work. After a while you heard him leave Roman’s office and you smiled to yourself, thinking he would stop in. He did not. He walked out of Roman’s office and walked directly to the elevators, intent on leaving. You frowned to yourself. Did he not see you? Or is he just busy? There is a board meeting tomorrow so you could talk then.
Stewy walked into the meeting right as they were about to start, so you didn’t get to talk beforehand. You tend to linger after the meetings anyway in case any of the members need you for something. At the end of the meeting, Frank did pull you aside to mention something. Out of the corner of your eye, you can see Stewy leaving the meeting room. Sometimes he’ll leave and just go wait in your office, so you assume that’s what he’s doing now. You smile to yourself and then turn back to Frank. When you’re finished with your conversation, you head back to your office. You start racking your brain for things you have been meaning to tell him with a smile growing on your face only to walk past your office and find it empty. You halt and look around quizzically. You stop by your assistant’s desk, which is right outside your office, and ask her if anybody stopped by.
“Uh no, not just now,” she answers.
“Oh,” you reply. “Really?”
“Uh huh… Is everything okay? Are you looking for someone?” she asks as you look around the office.
“Uh… no. No, everything’s fine,” you flash her your signature “all good” smile and scurry on back to your office, leaving your assistant confused. She is used to your frantic-ness, so she watches you enter your office and then resumes her work. You plop down on the couch in your office with a sigh. Two days in a row? Is he really THAT busy? No way. Is he avoiding me? What did I do? You shake yourself out of your thoughts because you have work to do. You decide to wait it out and see what happens within the week.
He had been to the office twice more during that week and avoided you completely. You were fed up. What the hell did I do? Why is he being such a dick? You call him on Friday evening, and he doesn’t pick up. No way he is THAT busy. Fucking ass. Fine, if he wants to play that game, I can play that game! You in fact did not want to play that game but he started it. Yes, you’re aware that is childish, but your anger is blinding you and you’re feeling petty. The weekend passes and nothing else happens. There’s a board meeting on Monday and you decide to confront him afterwards. You were going to force him to talk to you afterwards. He can’t avoid you forever, right?
Though he can try. Once again, he timed his entrance to the meeting so he wouldn’t have to speak to anyone beforehand. He sits down silently, across the wide table from you, like always. He can feel your eyes on him, but he doesn’t look at you. At least not until you’ve scoffed under your breath and turned away from him. You don’t notice his eyes on you amidst your frustration towards him. You focus on Frank and Gerri and their agenda for today’s meeting. You even take notes while Stewy, unbeknownst to you, watches you. More like admires you, really. He’s in awe of you. He is sometimes perplexed on how a person like you can exist in a world as fucked up as yours. He knows it’s changed him, but it never seems to affect you. It overwhelms him, especially since he’s been seeing you in person regularly. Whenever there were stints of time in between your interactions, he could push the thoughts back, pretend they aren’t there. But as your encounters have become more frequent, so have his thoughts about you. He always thought of you, ever since you met. He would read a book or watch a movie and think she would like that, or she would hate that. He keeps a mental checklist of things he knows you like and whenever he sees anything pertaining to that thing, he thinks of you and smiles. He used to think that was special to your friendship. He didn’t have many female friends before you, so he had never experienced this before. It took him a while to realize that people don’t think about their friends that way. He doesn’t want to think of these feelings right now out of fear it’ll overwhelm him. He’s afraid to even open his mouth around you and have everything spew out. So, he avoids you. He knows it’s not right or smart but it’s the only thing he can think of doing right now without ruining everything. As soon as the meeting is adjourned, he’s out of his chair and heading for the door. You immediately move to follow him, ignoring the looks from Frank and the others as you do. You try to catch up to him as quickly and quietly as you can. When you finally catch up to him, you grab him by the arm and pull him into your office without saying a word.
“What the hell?” He turns to look at you. You don’t bother to answer and instead launch into the rant you had been practicing all morning.
“Did you get a new phone number?” You ask innocently.
“No?” He replies, confused as to why you’re asking.
“And your phone is working?” You continue.
“Yes...”
“And you’ve seen me in my office, right? You’re not going blind?”
“No, I am not going blind,” he sighs.
“Is anyone dying?”
“No, why the hell are you asking me-”
“So, you don’t have any good reason to be avoiding me then?” You finish. He doesn’t reply. You raise your eyebrows as if to say well?
“I haven’t been avoiding you-”
“Save it, Hosseini,” you cut him off immediately. You were tired of playing this game. “Are you mad at me or something?”
“No, why would I be mad at you?”
“I don’t know, I’ve been wracking my brain and I can’t think of anything. What the hell is going on? You’ve been avoiding me for two weeks without a good reason? Seriously? What the fuck?!” You’re starting to get frustrated at this point. You told yourself you would try to remain calm but when he’s looking at you like you're crazy, it’s a bit off-putting. He still hasn’t given you much of a response. You throw your hands in the air and turn away from him. He sighs and puts his hands on his hips.
“You want to know the truth?” he asks softly, causing you to face him again. You nod your head. Another sign comes from him, and he looks at the floor. “Because you drive me fucking insane,” he laughs under his breath. At first, you're not sure you heard him correctly.
“What?” You have never been more confused. “I don’t... What are you talking about, what did I do?”
“It’s not anything you did,” he says, eyes still on the ground. “It’s just you.”
Your forehead creases in confusion. “Okay... Then what-”
“I’ve been avoiding you because I’m afraid I’ll say something I’ll regret,” he exhales. He’s looking at you now, almost sad. You don’t understand.
“Like what? What could you possibly say to me that could be so bad?” You’re exasperated. “You just said I drive you fucking nuts, what am I supposed to fucking do with that?!” You’re shaking your head and starting to pace. He’s upset you; he worded things wrong. “Fuck,” he whispers to himself.
“I don’t know how to do this,” he says, pointing between the two of you.
You turn to face him and breathe out a laugh, “You were doing just fine a week ago!” You stop pacing and look him dead in the eyes. “What the hell changed?”
“Nothing!” he says. He’s exasperated, too. “I just…”
He looks at you, trying to figure out how to word the next part. What he says now will affect your relationship from now on. There’s no going back.
“I don’t know how else to say it so I’m just going to... say it...” he begins. He takes a deep breath and briefly closes his eyes.
“Do you remember when we met?” he asks. You blink a few times, what does that have to do with-
“Yes,” you reply.
“I saw you in the house before Kendall told me who you were. I thought you were beautiful. I mean I still do but... that first time I saw you? I was head over heels already. And then I found out who you were and immediately shut those feelings down. Ken’s baby sister? No way, he would kill me, your dad would kill me, it couldn’t happen. But then I got to know you... and God I was fucking...” he lets out a deep breath.
“You have no idea the effect you have on people, Y/N. How important you are to people. To me.”
A beat passes.
“You’re important to me, too,” you whisper. He smiles and closes his eyes, that thing he does when he genuinely takes what you’re saying to heart. He knows that but it’s still nice to hear.
You’re afraid he’s going to end the conversation there. You take a step towards him and gently say his name, “Stewy-”
Before you can even think of something else to say, he says, “I’m in love with you.”
Now it’s your turn to take a deep breath. He takes that as a sign to continue. “I should have told you sooner but I... I didn’t realize what I was feeling, but I know now. It’s love. I love you, Y/N. I think I always have. You don’t have to say anything or feel the same way, but I owed you an explanation. And an apology. I’m so sorry for everything, especially for making you feel like you did something wrong. You didn’t, you’re... You’re perfect. I’m the asshole.”
When he’s finished, you stare at him for a bit with your mouth open. You then start to shake your head in disbelief.
“You’re an idiot,” you finally say.
“Probably,” he replies. “For what?”
You take a deep breath.
“I have loved you since the minute I laid eyes on you,” you tell him. His stance shifts and he is trying to process what you’re saying. “I just kept it to myself because I always assumed you only saw me as Ken’s annoying little sister.”
“Well, no, that’s Shiv,” he says causing you to laugh. Your laugh makes him smile. “But don’t tell her I said that because she's scarier than you.” You laugh harder.
“God are we really this stupid?” he asks while laughing.
“Speak for yourself, I know what I feel,” you reply. He’s smiling at you and begins to nod.
“You’re right. I’m an idiot.”
You smile at him. “Yeah, well...”
He’s shaking his head in disbelief. “Wait do you really... I mean is this... real? Is this really happening?”
“What did you think would happen?” you ask him.
“Honestly?” You nod. “I thought you would slap me and tell me to fuck off.” That pulls another laugh from you. Eventually he joins in.
“This is real,” you say. “At least, it is for me. I’ve never felt this way about anyone. And believe me, I have tried.”
He smiles, “I know. Me either. I mean, you’re it for me. I think I’ve always known that, but I just hadn't accepted it until recently.”
You nod. He takes a step closer to you and takes one of your hands in his. “So... what now?”
“We should probably talk about what all this means, at some point.” He nods in agreement and takes your other hand. “Um, we’ll have to decide if we want people to know... Because that could be tricky business wise. And we’ll have to tell Kendall and my dad, at some point. I don’t think they’re going to be happy but, whatever. We’ll have to inform the board, Sandy, and Sandi, talk to HR-”
“Y/N?” he stops you.
“Hmm?”
“You’re overthinking again.”
“Right. Sorry.”
“Don’t apologize, it is one of the many things I love about you.” He’s practically beaming as he says this which causes you in turn to beam at him. You move closer so his hands are on your waist and yours are on his shoulders. You look at him.
“Say it again,” you whisper. “Please?”
He doesn’t even need to ask what you mean. He tightens his hold on you and looks into your eyes.
“I love you.”
Your face hurts from smiling. He smiles back at you.
“I love you, too,” you tell him, and he breaks out the biggest smile you’ve ever seen on him.
You’re both still beaming at each other when he gently rests his forehead on yours and takes a deep breath.
After a beat he asks, “Can I... can I kiss you?”
“You better,” you tell him, and he tips his head back to laugh. He looks at you and brings a hand to cup your cheek. He searches your eyes for any hesitation and slowly leans in. He gently presses his lips to yours and somehow, it’s even better than either of you had ever imagined. After a moment you break apart and you giggle. He smiles and moves back in to kiss you, his hand firmer on your face. You both can’t stop smiling. You keep the kiss relatively short and tame. When you break apart again, he has your face in both hands and your arms are under his.
“Can I take you to dinner tonight so we can talk?” he asks you.
Before he can even finish the question, you are saying yes.
“Yeah?”
“Yes. I would love that,” you tell him.
“Okay. I’ll pick you up at seven?”
“Perfect.”
“Good,” he’s smiling and leaning back in to kiss you when there is suddenly a knock on the door causing you both to freeze. You can’t see who it is from your position, so you untangle yourself from Stewy and go over to open the door. He sighs as your warmth leaves him. You open the door to your brother, Roman, looking a little pissed. You open the door just wide enough to where he can’t see Stewy in your office.
“Oh, hey Rome, what’s-”
“It’s noon,” he says cutting you off.
“Okay...”
He widens his eyes and then it hits you, you were supposed to meet your brothers for lunch at noon.
“Shit, I’m so sorry, I didn’t see the time,” you tell him.
“Are you still coming or what cause I will go without you if I have to,” he says, talking one hundred miles a minute.
“Uh,” you quickly look back at Stewy to gauge his reaction. He is shaking his head no. You turn back to your brother, “Actually, can we rain check? I accidentally double booked my lunch today and-”
Roman waves you off, “Yeah, yeah, fine, whatever. Oh, have you seen Hosseini around?”
“Uh not since the meeting,” you lie, which you’re not very good at. You’re grateful it’s Rome asking you and not Kendall because he could read you like a book. Rome would rather use his energy elsewhere, like kissing up to dad.
“Okay, let me know if you see him,” Rome adds. “I wanted to ask him if he knows any coke dealers in Prague.” And with that, he turned around and left. You are trying to process what your brother just said about cocaine when you feel the door being pushed closed from behind you. Stewy pressed a hand above your head on the door to close it. You turn to face him, and he has a devilish grin on his face. His free hand snakes around your waist and he asks, “Now, where were we?” before sealing his lips to yours again.
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