Work Text:
Dean isn’t quite sure what possesses him (perhaps, at his impending disciplinary hearing, he could claim that he was bedeviled by the patron saint of bad ideas) to do it.
What it is — the immortal question, going unanswered by Faith No More and other highbrow philosophers — is Dean getting himself fired.
And not for a good reason that any self-respecting, anti-capitalist, Gen-X-slash-Millenial would consider honorable — like stealing from the register, or punching a deserving entitled customer in the face — oh no.
Dean’s going to get canned for hitting on his boss.
It’s pretty much rule number one, right after ‘bend your knees not your back when lifting heavy boxes of paper’: don’t attempt to fuck the boss.
A simple rule for probably about 98% percent of the world’s population who don’t have an absolute hotass for a boss. Those who do? Well, either they’re better at controlling themselves than Dean (not an impossible feat; Dean’s impulse control is right up there with a pyromaniac in a match factory), or they are at least a bit more discreet about it.
Y’know, subtle. A coy smile, a fluttering of lashes, sitting on their desk so that your crotch is right in their eye line, accidentally-on-purpose dropping your pen so that when you bend over, they get an eyeful. That kind of artfulness.
They probably don’t try to get into the boss’s pants in front of the entire work group chat.
Because it takes a special kind of idiot, and Dean may not win awards for many things, but in idiocy? He takes home the gold.
In Dean’s defense, 1) he's been in lust with Castiel for literal years, 2) everyone played along, and it was a funny interaction, but now Dean’s left with a weird squirmy feeling in the pit of his stomach, like a load of eels are slipping over each other, and he’s not sure whether to throw up or rub one out.
In the end, he splits the difference and re-reads the text exchange that he’s been quietly panicking over at his desk for the last hour or so.
Cas: Hello, everyone. I’m letting you all know that I won’t be in today as I’m currently at the hospital. Last night I injured my ankle on a patch of black ice outside my house, and it has swelled up rather alarmingly (my ankle, not the black ice). I have wifi, but no cell service, so if you need me, please WhatsApp call or message me.
Jo: Oh no! Hope all turns out okay. Wishing you back on your feet (!) soon, boss.
Dean: just as well my halloween outfit is a sexy nurse, let me know if you need me to rub your ankle
Charlie: replying to Dean: HAHAHA. Need to see it.
Jo: replying to Charlie: I don’t!!
Cas: replying to Dean: My place, 6 pm
Charlie: replying to Cas: Looks like you chose treat, Cas.
It’s not like Dean is overly attached to his office job — probably just as well, considering — but he does like being able to eat and pay rent.
Still, despite the chances of Dean going round to Cas’ place for sexy times rather than sad shouty firing times being in the median range of zero to minus fifty, there’s a small (actually, above average) part of himself that is hopeful. Because like Monty Python sang, you should always look on the bright side of life, and Dean is nothing if not a staunch optimist when it comes to getting his dick wet.
Because he could show up at Cas’ in costume, couldn’t he?
If he is going to get fired, then he’s got nothing to lose. And if Cas — the stoic, serious, sexy motherfucker — is actually flirting with him? Well then, Dean's got everything to gain.
It’s Dean’s very own game of trick or treat. He gets fired or he gets laid, but either way, he goes out with a bang.
***
As it turns out, chicks have cornered the market on sexy nurses. Dean considers himself a feminist, but there ain’t nothing equal about the plethora of adult nurse costumes that he’s faced with in the busy, last-minute-panic-buy-oh-fuck-it’s-halloween, store.
There’s something for everyone’s kink — as long as that kink is skewed female. From the traditional naughty nurse with an impractical garter, to midwife scrubs, to Florence Nightingale’s modest floor-length gown and apron. But there’s not a whole lot of hot male nurse costumes. There’s a doctor costume, because of course there is, but that’s not what Dean promised.
And Dean likes to keep his promises. Especially to hot bosses.
So, it’s with a heavy sigh that he chooses a traditional white latex number off the rack, and a pair of stripper heels that he’s gonna have to cram his toes into like a fucking geisha.
Who knows, maybe he’ll break his ankle too, and end up in the hospital next to Cas.
***
Dean doesn’t know how chicks do it. Driving in heels is a literal nightmare. Like one of those where everything is happening in front of you, but you can’t control it. Except you’re also in a car that you theoretically have control over, but it’s like there’s a golf ball stuck under both the accelerator and the brake at the same time.
Whether warranted or not, Dean totally gets the stigma about women drivers, because fuck .
Getting out of the car is quite an ordeal as well, because Dean’s all Bambi-on-ice in 6-inch heels, while simultaneously trying to tug down the painfully short dress over his ass and balls. For any nosy curtain-twitchers watching to see who leverages themselves out of a loud-ass monster car, they’re certainly in for a head-shaking, eyebrow-raising time.
Halloween or not, drag is an art that’s not always appreciated by the middle classes, and as Dean clings to the doorframe of the Impala for dear life, he realizes that he didn’t think this through.
What if Cas’ neighbors are homophobes? What if they’re… whatever the Halloween equivalent of Scrooge is?
Though, as Dean glances around, keys clutched and digging into the meat of his palm, he can see a few promising spooky decorations on nearby porches. Which is something at least.
Leaning his weight against the rear door on the driver’s side, Dean tries to smooth his outfit down. The dress is built for cleavage that Dean doesn’t have, but if he’d thought ahead, he probably could’ve worked some magic with tape and his pecs.
Nothing about anything Dean’s doing right now suggests there was any thought at any stage, let alone pre-planning.
It’s the very opposite of premeditation; it’s postmeditation.
The stethoscope around his neck is cold against his bare skin, and the little white hat balanced precariously on his end-of-day hair is certainly doing very little to keep his head warm. The suspenders make his skin itch, and as he teeters up the pathway to Cas’ neatly kept mid-century modern surrounded by a literal white picket fence with plastic skeletons leaning over a side each as if they’re in deep conversation, Dean shivers.
(On the plus side, his dick might’ve retracted into his body, so at least there’s little chance of it making an appearance from under the hem of the dress.)
The eels are slip-sliding about again and if he doesn’t end up going ass over tit, it’ll be a Halloween miracle. Each step is hard won, and by the time Dean reaches the front door, he’s too relieved to care about whether he’s in for a trick or treat — as long as Cas will let him take off these damn shoes .
Thing is, Cas is a good boss, and Dean’s enjoyed working under him (wink wink) for the past two and a half years. It would be a shame to lose his job, but that ship kind of sailed when Dean let his dick do the (metaphorical, he’s not that talented) typing.
So, rather than stand outside any longer — he’s genuinely worried he might get upskirted by some enterprising teenager late to the mischief night celebrations — Dean decides that it’s time to just go for it.
Fire or fuck. Trick or treat.
Cas has a fancypants Ring doorbell, so there’s every chance that he’s seen Dean standing on his porch, having some kind of inner crisis while wearing a naughty nurses uniform.
It takes him long enough to answer the door that Dean’s convinced Cas either ain’t home (which can’t be the case, because the lights are on, and nobody leaves lights on during Halloween unless they’re home and willing to answer the door to costumed strangers) or that he’s enjoying making Dean wait.
It soon becomes apparent that it’s neither of those things, because when the door swings open to a warm and sweet-smelling home, Dean’s boss is on crutches. He’s also shirtless, and wearing nothing but sweatpants and a boot on his right foot. Dean doesn’t know where to focus, but eventually, he settles on Cas’ face, which has more dark stubble on his jawline than usual, and his plush, pretty mouth is curving up into the beginnings of a smirk.
Ah.
Cas’ blue eyes sparkle with amusement as his employee stands there, towering over him in stripper heels, wearing (that word is doing a lot of work) a white latex naughty nurse outfit. If anything deserves a million-dollar payout in a sexual harassment case, it’s this.
Fire or fuck, let’s do it.
“Hi,” Dean says, trying to sound as seductive as possible while his teeth are threatening to chatter. “I’m here to give you a sponge bath.” He figures it’s marginally more subtle than “Drop your pants, I’m a nurse”.
“Oh,” Cas says in that throaty, deep voice of his. “I’m so glad you’re here. I’ve fallen pretty hard, and I’ve just had my breath taken away —”
Dean’s in love. Any man, woman, or enby who can cram that many puns into a single sentence is marriage material.
Cas continues, his eyes alight with mischief and humor, and holy fuck, maybe, just maybe this is Dean’s treat after a lifetime of tricks. “ —so can you show me how to do mouth-to-mouth… on me?”
Fuck it is.