Work Text:
Castiel hates these stupid office parties, but as the CEO of the company, he can’t exactly skip them. Even if it means wearing an ugly Christmas sweater, listening to the same ten Christmas songs on repeat, and participating in the office's secret Santa. That last one is what he hates the most. They give a fifteen dollar limit, and they all buy stupid gifts that are guaranteed to go straight in the trash when the person gets home. Last year someone bought Castiel a cheap key chain with the letter ‘C’ on it. The year before that, he was given a self help book on how to make yourself happier. He hadn’t appreciated the slight nod toward his overall surly attitude in the workplace. The year before that, he was given a Star Wars bobble head. He hates sci-fi.
He always buys his person a practical gift, because he’s not an idiot. Last year he got Jan from accounting a gift card to Starbucks, which he knows she loves because she comes to work every morning with a to-go cup from there. The year before, he gave his assistant Jason a gas card, because his girlfriend lives thirty minutes away. Before that was Lukas, the receptionist, who ate skittles like they were going to stop making them. Castiel bought him a mega pack of each flavor.
This year he got Patty, the head of his finance department. Castiel bought her an Italian cuisine cookbook, because he overheard her in the break room last week saying her husband loves Italian food and she wants to learn how to make more of it for him.
Castiel is handed a thin box that’s wrapped in red and white striped paper, his name written on it in neat writing. He picks at the bow on the corner and starts to plan what he’ll say in his presentation later this afternoon. He’ll only have fifteen minutes after this stupid party before he’ll be expected in the conference room.
Did Castiel mention he fucking hates office parties?
----
Dean drinks his eggnog, really wishing it was spiked. When he went shopping for the present he got his boss for secret santa, he had brought his friend Charlie along. They had gone for dinner and drinks before. That’s probably why Dean thought at the time that it’d be a great idea to buy Castiel Novak, the CEO of the company who gives Dean his paychecks, cheap drugstore ladies lingerie.
In hindsight? Not a great idea. Not even an okay idea. Bad idea. Very bad.
When it’s Castiel’s turn to open his gift, Dean sinks further into his seat. He already opened his. It was a pair of fuzzy socks that he’ll secretly wear all winter. There have been a few gag gifts, similar in nature to what Dean bought Castiel, but always given to a jokester in the office, not the grumpy boss who doesn’t speak to anyone unless it’s barking orders.
Dean’s totally getting fired.
He holds his breath as Castiel methodically removes the wrapping paper from the box. It seems to take an eternity before Castiel is finally lifting the lid of the clothing box, peering down at his present. Dean knows that Castiel has no idea it was him who bought it, but he still can’t help that his heart races and his hands shake. What if Castiel has the list that someone makes every year to hold people accountable? What if he finds out it was Dean who did this terribly inappropriate thing?
“You have to show us!” someone teases, making people laugh.
That’s when Dean forgets about his own feelings, because he sees how Castiel is reacting. As he tentatively lifts the red santa babydoll top with white fur lining the edges, Dean notices that Castiel’s hand is shaking, and his cheeks are turning red enough to match the lingerie. He doesn’t lift the rest of the contents of the box, because the top is enough for everyone to get the picture.
Gabriel, Castiel’s CFO and best friend, immediately steps in to help everyone who doesn’t know if they should hurry to change the subject or laugh their asses off. “Wow, Cas. Didn’t know that was your thing.”
Castiel shoots his friend a glare but says nothing.
“It’s definitely your color,” someone else adds, taking a chance.
Then people are giggling and continuing the teasing.
“Brings out your eyes.”
“Will make your legs look great.”
“You can bring me presents if you want, Santa.”
By the time Castiel’s turn is over and attention has moved elsewhere, Castiel is completely flustered and looking ready to spring out of the room. His cheeks are still bright red, and he’s gnawing on his bottom lip like a nervous child.
Dean grins. This was so so worth it.
Except he makes the mistake of looking up, still grinning like an idiot, and making direct eye contact with his boss. His expression freezes and he finds himself blushing too. Castiel’s eyes narrow, and it’s clear he’s figured Dean out.
Dean’s not sure who runs out of the room faster, him or Castiel. It doesn’t matter. He knows he can never show his face to his boss again. He’d rather die.
----
When Dean came back to his desk, he had a note on it. A note he’s probably read a hundred times in the last few hours.
Mr. Winchester,
Please meet Mr. Novak in his office at 8 PM.
You will be compensated for the overtime.
Thank you.
Dean reads it again at 7:56 PM, waiting down the hall from the office door. He doesn’t know if Castiel is who wrote it, or his secretary, or someone from Human Resources. He doesn’t know if he’ll be yelled at, laughed at, or fired.
He doesn’t know which he’d prefer.
At 8 PM sharp, Dean knocks on the intimidating office door with Castiel Novak CEO in the center of it. There’s a slight pause, then, “Come in.”
After a deep breath, Dean pushes through the door and enters the massive office. He’s never been here before, he’s never needed to be. He’s not important enough. Dean is just some low level finance guy. He’s never even talked one on one to Castiel Novak before. Dean’s worked at this company for six years, and he’s had an intense crush on the CEO for all of them, but not once did he try to interact with him.
Castiel is sitting behind his desk, but stands when Dean enters. He’s shed his suit jacket and tie, leaving just a white button up shirt with sleeves rolled and the top two buttons undone. Dean’s never seen the man comfortable like this. All mussed and sexy. A little loose around the edges.
Then his eyes fall on the desk between him and Castiel, and he sees his present sitting there, the top off to reveal the contents. Dean gulps.
“Loved your present, Mr. Winchester,” Castiel says in a slow, smooth voice.
“Uh.. I - I didn’t-”
“Don’t lie, Dean. My secretary is who keeps the list every year. I know this was you.”
Dean feels his face flush. “I’m so sorry, sir. I didn’t-”
“Stop.” Castiel comes around the desk and leans back against it, arms crossed on his chest, legs kicked out with one ankle over the other. Far too casual for the situation. He drags his eyes down Dean’s body, taking his time to appreciate him. Dean feels like he’s under inspection, but he has no idea for what. “You see, I’m not a lingerie guy myself. But you seem like you’d look quite good in some.”
Opening and closing his mouth, Dean tries to think of something, anything, to say. When he comes up blank, Castiel smirks and says, “Maybe you should try it on for me.”
“Wh - wh - I -”
Ignoring Dean’s panicked stuttering, Castiel picks up the sexy santa top and lets it hang by a strap from his pointer finger. It dangles in the air as he offers it to Dean with a sexy smile. “Go on. I’m sure you’ll look lovely.”
Dean stares at it in shock. Then he realizes his cock is rock hard, and he’s hurrying to grab the top, snatching it from Castiel and putting it in front of his crotch. By the way Castiel smirks, Dean didn’t hide his boner fast enough.
“You don’t have to,” Castiel drawls. Even though he’s still teasing, still looking at Dean like he wants to eat him alive, Dean has no doubt that Castiel means that. He doesn’t have to do this. He can walk out right now. Keep his job. Never discuss this again.
“Just this?” Dean asks in a thick voice. “Or the rest too?”
“The rest? What else is in there, Dean?”
“The hat and the p-” Dean stumbles to a stop, realizing Castiel knows exactly what’s in the box. He just wants Dean to have to say it out loud.
Castiel’s smirk widens. “What was that, Dean?”
“Nothing.”
“Oh. Bummer. I was really hoping to see you in those panties."
Dean tucks his chin to his chest, wishing he could just disappear. He doesn't notice Castiel is coming closer until he sees his feet. A finger gently lifts his chin until Dean's eyes are on Castiel's.
Watching Dean for any sign of resistance, Castiel begins to undo his belt. Then the button of his pants. The zipper. He slides Dean's jeans down to his ankles, purposely brushing his cheek against Dean's boxer covered boner.
Without being told, Dean toes off his shoes and steps out of the pants. He stands there in his candy cane socks, black underwear, and ugly Christmas sweater. The sweater is removed next. Then the socks. Then, with one final look, Castiel pulls his boxers down to his ankles.
When Dean is standing stark naked in front of a very sexy, very dressed Castiel, his blushing kicks in again. Thankfully, Castiel distracts him by pulling him in for a kiss. He devours Dean with his lips, tongue, and teeth until Dean is breathless and trembling. Then he pulls back and places fabric in Dean’s hands.
“Get dressed for me. Nice and slow. I want to thoroughly enjoy my present.”
----
By the time Dean is dressed in the Santa lingerie - including the little hat and the silky stockings - his rock hard cock is leaking through the satin panties and he’s trembling. He looks up at Castiel through his lashes, anxiously nibbling on his bottom lip. Dean’s confidence is boosted when he sees how wrecked Castiel looks in front of him.
“You’re gorgeous,” Castiel whispers, reaching out a hand and running it along Dean’s arm. He leaves a streak of goosebumps in his wake. They’re like a plague. By the time Castiel pulls away, Dean’s entire body has erupted in the tiny dots, shivers running up his spine.
Taking Dean’s hands, Castiel guides him over to his desk. He sweeps his hand across the top to get everything out of the way before laying Dean on his back across it. Castiel’s touch is agonizingly slow as he runs his fingers down to the beautiful stockings. Dean moans at the feeling of being tickled through the silky fabric, muscles melting in pleasure as his skin erupts with fiery need.
Dean looks up into Castiel’s eyes, hoping the man can understand how desperate he is. But Castiel just smirks down at him and continues teasing Dean with his fingertips.
“Cas-” Dean stops himself. He swallows hard and tries again. “I mean - Mr. Novak. I-”
“No. Cas.” Castiel leans over him, brushing his lips along the shell of Dean’s ear. “I like you callin’ me Cas. That’s what I wanna hear you screaming when I fuck you on my desk.”
Gasping, Dean lifts his hips and grabs two fistfuls of Castiel’s hair, holding him close. “Yes. Fuck me. Now.”
“Patience. I’m trying to thoroughly enjoy my present, Dean.”
“Sorry,” Dean whimpers. His body is shivering even though he’s overheating. If Castiel doesn’t fuck him soon, he’s fairly certain he’ll explode. “Please, Cas.”
“Shhhh.” Castiel pulls back, placing his lips over Dean’s. He kisses him slowly, each touch gentle, sweet, completely opposite of what Dean would expect from the man. As he continues working against Dean’s lips, Castiel wraps his big hands around Dean’s calves and lifts his legs up. Slowly, Castiel drags his fingertips along Dean's legs until he’s at his bare thighs where the stockings stop. Then, Castiel parts them, settling his body into the open space. A few more adjustments and Dean is spread out wide, feet on the edge of the desk, red-panty-covered hole on display. Castiel breaks the kiss and presses the pad of his thumb against the spot where he knows that hole is hiding. Dean chokes and cants his hips.
Finally - finally - Castiel is unzipping his pants and pulling his cock out. He takes out the bottle of lube and condom he had put in the lingerie box with the hope this would happen, squirting some lube on his fingers. He moves those pretty panties aside and rubs the liquid against Dean's tight pucker, smiling when Dean whines and thrashes his head.
“So responsive,” Castiel coos. He dips a finger into Dean and begins to work him open, his cock leaking a puddle against the desk where it rests. “I like it, Dean. I like you.”
“Like - like you too.”
“Yeah?” Castiel adds a second finger, chuckling as Dean spreads his legs wider, lifting his hips to try and get more inside him. “You gonna let me fuck you, Dean?”
“Fuck yes. Now. Come on.” Dean rests his stocking covered feet over Castiel’s bare ass, trying to pull him in. Castiel shivers at the feel of the material against him.
He can’t wait any longer. Two fingers is going to have to do.
Castiel rolls the condom on before slathering it with lube. Then he’s pressing against Dean’s hole. Dean startles, looking up at him with wide eyes. “Aren’t you gonna take the panties off?”
“Of course not. You’re not the present, Dean. The pretty clothes are.” Castiel nudges Dean’s hole until his head is breaking past the rim, then adds, “You’re much more than just a present, Dean. Much more.”
“I - I’m not speci- aaaaaaaaah.” Dean arches his back and nearly screams as Castiel fucks into him hard, slamming the remaining seven inches of his cock inside Dean in one sharp movement. Feeling his eyes roll back in his head, Dean can do nothing but widen his legs and rest back against the desk, giving into the overwhelming feel of being stretched and filled. It burns in the best fucking way.
By the time Castiel has set himself a steady rhythm, the burn is gone and all Dean can think is he needs to come. He needs to come right the fuck now. It’s pathetic - he’s not some teenager that can’t last more than a minute - but between the teasing, and the dirty talk, and the fabric that feels fucking amazing on his cock, and the look on Castiel’s face, and the way he fucks Dean at just the right angle and speed to turn him into a whimpering mess? Yeah. Dean’s not lasting.
“Fuck, I’m not gonna last,” Castiel grunts, echoing Dean’s thoughts. He reaches into the panties and wraps a hand around Dean’s cock, having no idea Dean was about to blow as is. It only takes two pumps before Dean is coming undone, covering his panties and santa top with cum.
Castiel groans. “Fuck. Look at you. So fucking sexy.”
Hanging his head, Castiel pounds into Dean three more times before pausing deep inside him and coming. The two of them continue panting, trying to catch their breath. As they come down from their highs, Dean begins to shake again. This time it’s not because he’s horny or desperate or on the verge of exploding. It’s because Dean just got fucked by his boss. On his desk. At work.
What the hell was he thinking? What happens now? They can’t work together. What if someone finds out? What if he gets fired? Or worse, what if he gets a fucking promotion? Then he’s just some damn sleaze that fucks his boss to get ahead. And what happens with them? Was this a one time thing? Are they-
“Dean,” Castiel whispers. “Calm down.”
Blinking his eyes a few times, Dean realizes that Castiel is out of him and already zipped up. A warm washcloth is cleaning Dean. His panties aren’t even on anymore. Castiel helps him sit up and takes his top off, then his silk stockings. When Dean is completely naked, Castiel puts the washcloth to the side and cups Dean’s face with gentle hands.
“Calm down, Dean. Breathe.”
“I have to go.”
“No.”
“Let me go.” Dean shoves Castiel, hopping off the desk and hurrying to get his clothes on. He trips and falls to the ground after trying to shove his legs into his pants too quickly.
Castiel picks him up, not letting go until he’s stable on his feet. “Dean, this wasn’t what you’re thinking it was.”
Feeling his face heat up, Dean turns his back and forces a scoff. “I know that. I’m not some clingy asshole. It was just a hookup.”
“Oh.” Castiel clears his throat. “Is that - is that what you want?”
“I-” Dean adjusts his shirt that he just pulled over his head. His hands are shaking. “What do you want?”
“Dean-”
“Nope. You started this. You have to say it first.”
Castiel chuckles softly. “Alright, you got me there. But you have to look at me.”
Closing his eyes and taking a huge deep breath, Dean faces Castiel. “Okay. Go.”
“I’ve wanted you for a long time, Dean. But I was your boss and I never wanted to make you feel uncomfortable or pressured.” When Dean snorts, Castiel nods. “Yes, I’m aware that’s hypocritical considering what we just did. But.. I don’t know. I guess I thought you giving me that present was telling me you like me too. I got excited. Thought you liked me on your own, without thinking you had to as my employee. That’s stupid.”
“No. It - it makes sense,” Dean whispers.
“Was I wrong though?”
“About what?”
Castiel looks unsure for the first time. The confidence is nowhere to be found. Dean kind of likes the vulnerability. It makes this feel like they’re on the same level. “Was I wrong about you wanting me?”
“I think I made it pretty obvious I want you. I fucking dressed up like a slutty santa just now and let you fuck me.”
“Right. Of course. I meant,” Castiel rubs the back of his head anxiously. “Do you want more than that?”
“Like a relationship?”
“Yeah.”
Dean looks away and over at the window. Their company is on the 53rd floor. It has an amazing view no matter what window you look out of, but as the CEO, Castiel has a view that’s more than amazing. It’s breathtaking. Overlooking the water, mountains off in the distance. At this angle, you'd have no idea an entire city is just out of sight.
This is how Castiel’s entire life is. Good views. Money. Expensive clothing. Fancy restaurants. “Why would you want that with me?”
“Dean-”
“I’m serious.” Dean looks at him, eyebrows pulling in. “I’m nothing. Just some little worker bee. And don’t address that, because if you offer me a promotion or a raise or some shit like that, I’m going to fucking punch you. I’m not some whore fucking my way up the career ladder, okay?”
“Dean, I would never assume that’s what this was. But I don’t give two shits what your job is or your salary or any of that.” Castiel takes a deep breath, his cheeks turning slightly pink. “I want you because when someone forgets their lunch, you pretend you had a big breakfast or you packed too much so they'll let you share. I want you because when Lucy got cancer and had no family to drive her to all her appointments, you took unpaid time off to bring her to every single one. I want you because you're obsessed with pie and become a little kid whenever someone brings one to the breakroom. I want you because you convinced the entire office last year to throw a surprise retirement party for Donny. And those are just a few reasons off the top of my head."
When Dean just stares at him in shock, Castiel adds, "Your job will never be affected by a relationship with me - positively or negatively. If I was wrong and you don't feel the same, be honest. We will forget this happened. I swear it. But if you do feel the same? I'd really like to take you to dinner tonight."
"Okay," Dean says in a hoarse voice. He takes one step closer to Castiel, feeling his belly flip. "Dinner it is."