Work Text:
When you first met Kendall Roy you thought he was a very sad man.
His assistant had quit and for some time he called you by her name.
"I'm sorry, it's just that Jess was my assistant for almost six years, we went through a lot together." He smiled at you with all his teeth with that particular smile that didn't quite reach his sad hazel eyes.
"Don't worry, I understand." You'd reply and continue working, though in your mind you'd wonder what he meant by "we went through a lot together."
You certainly didn't consider yourself a lovey-dovey person, you had actually had two serious relationships and one of them had almost ended in marriage, but he wanted children and you weren't ready for that yet, so the two of you had broken off the relationship on good terms.
You had always been a fairly efficient executive/staff assistant. You knew he had hired a prestigious human resources agency to recruit candidates. When you broke off your long relationship with your partner and decided to move to New York and start over, when you went to the job interviews and completed all the rigorous recruiting stages, you finally met your boss: Kendall Roy.
It was there that you thought you had never seen such sad hazel eyes, plus his deep voice and his hands, you didn't know how to explain it but you found your boss's hands extremely attractive.
Sometimes you thought about him a lot, especially when you watched movies from the female point of view, it was very true that female directors or screenwriters used to emphasize the eyes and hands of the characters.
Suddenly you found yourself fantasizing about your boss, about his voice when he didn't call you by the name of his former assistant, about his hands when he moved them repeatedly almost like a mania to explain something, about his eyes that were always sad and adorably hazel like those of a baby deer.
You had to accept that you liked your boss because you thought about him too much and not only during work but in your free time at home, watching movies, cooking or masturbating. It was surprisingly easy to think about his hands, specifically his thick fingers and you would lie if you didn't imagine his cock.
After six months you noticed that you sighed every time you smelled his tobacco and vanilla cologne that he left in the air as he passed by, plus he had stopped dyeing his hair and the natural gray tone had come to light making him look even more irresistible.
The job started to be a condemnation and a reward in equal parts, you could be by his side and work with him, smell his cologne, hear his voice, see his sad hazel eyes, from time to time brush his fingers with yours when you handed him some document, but after that you realized that he only saw you as a simple assistant and that you would never fill Jess Jordan's place.
You wondered if the two of them fucked, but you didn't even dare to ask him, he was so professional and focused on work that you knew you couldn't cross the line.
So you hated your situation, you didn't like remembering your college days when you had a platonic love affair with your professor that was never going to happen, you had a problem with authority, you couldn't possibly have a crush on your own boss who was also ten years older than you.
He was kind and polite to you, he had considerations with you.
"It's Friday night, you should be with your friends or your boyfriend and not here, sorry for forgetting these papers, but it was very important that you bring them to me." He said to you as he signed the papers.
"Oh don't worry, I literally don't even have a dog to bark at me when I get to my apartment, I was thinking of adopting one actually, since I'm new in city I don't have any acquaintances yet." You mumbled and then felt embarrassed that you had given him so much information.
He just smiled at you, you picked up the papers he had signed and scanned them, the next day a little golden haired Cocker Spaniel showed up at your door, it was a dog from a stray adoption association, so they were coming to drop the dog off and give you a form you had to fill out to officially make it yours.
On Monday you came to work, you didn't know what to say, you knew it was him, but neither of you mentioned it, and so things were happening between the two of you.
You said you would kill for a chocolate donut and he had a dozen delivered to the office, you said it would soon be your birthday and that you would like to visit your mother and he gave you a trip home in his private jet and also took you and your mother to dinner at one of the most luxurious restaurants in your old city.
That time when he went to the restroom, your mother ambushed you.
"Are you fucking your boss?"
"Mom of course not!"
"Oh well what a waste, he's a great catch."
You couldn't believe your own mother would tell you that, but she was right, Kendall Roy was a great catch, maybe he had once been a disaster and you knew that from the news, but now he was a good man who was focused on his children and the company he was founding.
You had been part of the company from the beginning, as his assistant you knew many things about him. You knew his brothers, especially Roman and Connor Roy, as he was estranged from his sister.
Roman had told you when you were busy in the office with some papers.
"So you're my brother's new boy toy."
"Excuse me?" you blinked.
Kendall had warned you about his brother's behavior.
"Yes, Jess's replacement."
"I'm Mr. Roy's assistant if that's what you mean."
"Yeah, whatever, Jess will always be better than you."
"I try to fill her shoes as best I can, sir." You hissed.
"I bet with Shiv, you know, they hate each other, but she's still my fucking sister, so I bet with her, I told her about you and how much Ken likes you, she says you two are already fucking, I say Kendall is dumb enough to do that, uh, you know, he would never fuck a female employee because uh he doesn't want a sexual harassment lawsuit, so poor you, you'll have to refrain from my brother's cock."
You were shocked and he laughed at you with his arms folded.
"Poor little thing, you really want my brother to fuck you don't you? You're his dumb assistant, you can only clean up his shit, he'll never see you for anything else." He walked away.
You felt tiny and that night you decided that you would quit, that you couldn't go on with that job.
You couldn't go on when you were so in love with your boss. The next day the two of you were going to Dubai on business. You planned to hand in your letter of resignation and give him a two-week deadline to find your replacement.
When the two of you were alone on the private jet and the flight attendants had left, he was looking at his lap top, you were looking at yours. He noticed the awkwardness in the air, you didn't used to be so quiet, that was what he liked most about you.
That you always had something to say, something to tell him, you talked about your little dog that you had named Park because he liked Central Park so much, about your mother and her witticisms at home, about your sugary tastes, about all the movies and series you used to watch, you talked all the time and kept him out of his mind.
Ken couldn't stand being inside his mind, he hated every damn second of it, all the horrible things, all the regrets, the constant chirping of all his misfortunes, but there was you and he had met you and he needed you like he had never needed anyone before, it was true he missed Jess at first, but she was happy where she was and he was happy for her and meeting you had changed his life.
"Is something wrong?" he asked with a smile.
You had the letter in your lap, you handed it to him and he put on his glasses to read it.
"Uh is this a fucking resignation letter?" he grunted.
You nodded. You had to be strong, you had to be firm.
He was furious and in a year working with him you had only seen him like this once when his sister sent him some flowers as congratulations for founding her digital media company, he made you throw the flowers in the garbage
"May I ask why?" he hissed through his teeth.
Everything was falling back on his shoulders, you were abandoning him, you were abandoning him like when Jess had left him, that time he had reacted badly, he had called her dumb and juvenile. He didn't want to act the same way with you, but he couldn't believe it, he had treated you so well, you two had connected in a way that even he hadn't connected with Jess for six years, he couldn't believe you were abandoning him.
You were about to answer the response you had rehearsed, he stopped you.
"Never mind, never mind. I need... uh... I need some air..." he stammered standing up and going to the Private Jet room.
He felt like he was having a fit, his chest hurt like it was a black hole, you were leaving him, and he suddenly realized how important you were to him, he couldn't let you go.
You had seen his moist hazel eyes, your heart squeezed, you couldn't leave him alone, you went to the room and saw him sitting on the floor next to the bed, he hugged his legs to his chest, you sat next to him and took his shoulder.
"Ken."
"You're going to abandon me, why? I can do better, just let me try, let me prove it to you." He was practically sobbing, he was touching his head, he almost wanted to pull his hair.
You couldn't believe your eyes or what he was telling you, he was pleading with you. You put your hand on his cheek and wiped one of his tears with your thumb.
"Ken, you don't have to prove anything to me..."
"Then why are you leaving?"
You didn't know what to say to him, you wanted to look away, you couldn't look into his wet hazel eyes any second longer, but he stopped you, took your chin and then kissed you.
You felt his soft lips, his breath, his hands on your cheeks.
You wanted to make him feel better, you wanted to tell him you would never leave him, you let your hands slip into his belt, unbuckled it and unzipped his brown pants.
He groaned.
"Uh wait, do you really want to...?"
"Yes, I want to." You interrupted him, he didn't say anything, just let you pull down his boxers.
He had a faint precum stain on the fabric and his member was hard, dripping small, glistening drops of precum.
You had fantasized about your boss's cock too many times, now you had it in your hands, you pumped up and down spreading the liquid along its length, you leaned down sitting next to him and spit on his member.
He sighed with his mouth half open unable to believe what he was seeing, he just stroked your hair while you took the head of his cock into your mouth.
He felt your tender lips around his cock, your tongue licking and making its way to suck the rest of his cock.
You cupped your cheeks trying to fit his full length, caressed his balls with your hands and he sighed, throwing his head back and looking up at the ceiling as he stroked your hair between his fingers with one hand and the other was on your jaw.
He didn't want to miss a second of your small mouth sucking his cock, of your juicy lips and tongue covered in his fluids.
So he watched intently, tracing the line of your jaw with his finger, holding your hair in a messy ponytail so it wouldn't get stained and you had all the freedom to lick, spit and suck.
He could hear you gagging and it only made him want to cum. He wasn't even lasting 20 minutes he felt like a complete loser, but you were provoking that in him.
"Fuck, fuck, I'm going to cum." He mumbled.
You looked at him and nodded. He understood he could do it in your mouth, so he let out a stream of his cum and you swallowed it all.
"Fuck, that was perfect" he said a little more smiling as he wiped your mouth and chin with the sleeve of his brown sweater.
He grabbed your cheeks and kissed you, you were so happy, if a little numb and he noticed. He lifted you up in his arm and carried you to the bed.
"What are you doing?" you asked when you felt him on you and his hand slipped easily under your skirt.
"Rewarding you for being such a good assistant honey." He murmured against your lips smiling broadly.
"Really? I don't remember it coming in my contract to give you a blow job to make you feel better Mr. Roy." You said playfully feeling his thick fingers between your wet folds.
"You will have a new contract for an indefinite period of time."
"Really?"
"Yes, they call it a marriage certificate." He smilingly replied sticking a finger inside you.
You squirmed with pleasure and he kissed you.
You were really willing to sign that contract.