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Mile-High Club

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Dean Winchester, AVP
Underwriter
Commercial Banking
Garrison Bank, NA

Dean thumbs the embossed lettering on his new business cards and smiles. It wasn't five years ago that his father threw him out on his ass on the streets of Lawrence, and he had to scramble to make it by, crashing on Ellen's couch until he scraped enough pennies serving at a diner during the day and bartending at night to get to Sammy, who had a nice place in San Francisco while he went to Stanford Law School.

When Dean made it to California, he picked up a job at a bank as a teller, which was decent enough, and he was treated nicer than he had been working in food service. It paid his half of the rent and he got a few benefits to boot. After a year, he was promoted into commercial as an administrative assistant. His boss, Bobby, the sales leader for Northern California, took Dean under his wing and mentored him. Dean got promoted to relationship associate, and after that, it was only a small leap into commercial underwriting.

Dean has his own office now. With a window. And a view. Of San Francisco.

Presently, he cannot see said view, however, because he is cross-legged on the floor in front of his desk, surrounded by piles of tax returns for a major chain grocery store. He puts his new business card back in his wallet and gets back to work, flipping through the massive credit compliance volume in order to figure out what the flying fuck the difference is between an SBA 7(a) loan and an SBA 504.

He is blissfully interrupted by a knock on his door.

"Come in," he calls, highlighting a large section on transaction loans for 504s.

The door opens and Bobby steps inside the office, taking a seat on the chair Dean moved to the other side of the room so he could have room to analyze the returns. Bobby, whose suit jacket is always discarded by eight in the morning, leans down on his knees and asks, "How's it going, kid? Liking the new digs?"

Dean looks up and smiles. "Yeah, it's great."

Bobby nods. "Good. Well, I got some news for you."

"Yeah?"

"We're shipping you to Cleveland for a week for training. You leave on Monday."

Dean's smile wavers and he swallows. "Great, I'll take Baby and make a road trip of it. It'll be awesome."

"Son, the bank ain't gonna pay your mileage on that beast of yours to get all the way to Cleveland."

Shaking his head, Dean says, "No, no, I wouldn't ask the bank to reimburse me. I'll get there myself. It'll be fun."

Bobby stares at him, blank. "Son, you're gonna have to fly there."

Dean continues shaking his head. "I can't do that, Bobby. You know I don't fly."

"Well you're gonna have to, because you don't even know how to calculate a debt-to-income ratio yet and no one else here does either."

"I'll Google it," Dean replies quickly, setting the compliance volume down and standing.

Bobby stands too. "You gotta go to the training, Dean. I'm sorry."

"Why Cleveland, though?" Dean asks, trying to keep himself from raising his voice. His hands are shaking and he's having trouble catching his breath.

Bobby sets a consoling hand on his shoulder. "Because that's where central underwriting is. You'll be fine. I promise." He claps Dean on the shoulder once and smiles, then leaves the office, closing the door behind him.

Staring ahead, unblinking, mouth agape, Dean vividly imagines himself trapped for hours in a flying metal death box.

Dean should have never accepted this promotion.

***

Dean sits in the cafeteria, staring at his turkey sandwich, unable to gather the motivation to eat it. Food doesn't really matter anymore when he's just going to die on Monday anyway.

Charlie-from-IT plops down in the seat next to him with a tray of food and giant cookie in her mouth. Dean supposes he can stop referring to her as Charlie-from-IT and just refer to her as Charlie, considering they've hung out outside of work a few times and he's pretty sure that makes them friends now.

Again, though, friends don't matter when he's going to meet his imminent demise in less than a week.

"What's wrong?" she asks, opening up her chocolate milk carton.

Not meeting her gaze, Dean thuds his forehead on the table and lets it rest there, looking at his hands which are clasped in his lap. He mumbles, "I'm gonna die."

"I told you those ratios are killer. You signed onto a job where you have to do math forty hours a week, and our future clients' livelihood rests in your hands. No thanks, man. I'll take telling people to reboot their computers a million times over that."

Dean lifts his head and glares at her. "I can handle math and decision-making, Charlie."

She stops short putting a fry in her mouth. "Oh. Then why are you going to die?"

He sighs, and says, "They're making me fly to Cleveland."

Charlie puts her hand on his shoulder and nods. "I understand. Cleveland sucks. There's a YouTube video about it."

"No, it's not that. I just..." Dean runs his hand over his face and grumbles, "I hate flying."

Rubbing consoling circles on Dean's back, Charlie replies, "To be fair, you should also hate Cleveland."

Dean groans, "I'm not gonna make it there in order to find that out."

"Sure you will!" Charlie reverts her attention back to her lunch. "It's, like, impossible for a plane to crash."

Dean glares at her again.

Charlie looks at him from the corner of her eye and sets her fork down. Sighing, she says, "Look, I get it. It's scary. But if you need to relax, you can always do the MHC thing."

"What's that?"

"The Mile-High Club," she answers. "It's like online dating, but for fucking in airplane bathrooms."

Dean gapes.

"What?" she asks.

"You do that?"

"Personally? No. I haven't tried it. But a bunch of dudes in my guild have done it on their way to conventions and stuff. Apparently the site is really... efficient at pairing people up."

Dean furrows his brow and shakes his head. "That's ridiculous. Don't you get in trouble for shit like that?"

Charlie grins at him. "Not if you do it right."

***

That night, Dean gets home to find Sammy studying for the Bar exam, so he orders them a pizza and grabs a beer from the fridge. He loosens his tie, props his feet up on the coffee table, and takes out his laptop.

Pretending the first item on his agenda isn't finding milehighclub.com, Dean checks his email and replies to Ellen before finally breaking his resolve and checking out the site.

He looks up at Sam, huddled over his his textbooks on the other side of the room, the soft yellow glow from his desk lamp casting eerie shadows over his face and darkening the circles under his eyes.

He's not paying a damn bit of attention to Dean. Dean isn't even sure Sam saw him come in, or heard him while he ordered pizza, or even knows he's in the room with him right now.

Dean turns his attention back to the laptop and makes himself a profile. He picks the username Impala89, and when he gets to the question, "Are you interested in men or women or both?" he hesitates, chewing on his lower lip.

He's had plenty of sex with dudes in his lifetime, and he has no trouble admitting the advantages of fucking and being fucked by the male form. He digs chicks too, of course. He really just likes people. And sex. And having sex with people. He's just not sure about the logistics involved in fucking a dude on an airplane. Then again, he reasons, if he opens it up to dudes and chicks, the likelihood he'll find a match doubles. So he clicks "Both."

He types in his flight information and his seat number.

There's one other user on the flight with him, who is in coach on the other side of the plane, named ThursdaysAngel.

ThursdaysAngel has none of his or her– presumably her– profile information filled out.

Dean can't drink during the flight because he'll be on company time, and he doesn't want to take any pills, so fucking a random stranger on a plane is really his best option at this point.

He sighs, clicks "Message," and begins typing.

I'm flying out on a business trip. 24/M/SFO. You?

To his surprise, ThursdaysAngel replies immediately.

I bet you like mysteries, businessman. Send pic please.

Dean smirks, and uploads a selfie to the chatbox. In the picture, he's standing in front of a mirror, shirtless, because he's really just the worst kind of cliché.

ThursdaysAngel replies:

Oh, you'll do nicely. Meet me in the lavatory between business class and coach, 5:47PM PST on the dot. Knock softly with Shave & a Haircut. I'll reply with Five Cents and then you can enter. Look forward to "meeting" you, sexy businessman! ;)

Dean grins. Setting up a rendezvous on an airplane was easier than going through procurement to buy the damn flight reservation in the first place.

He's nervous about the anonymity of it all, and how awkward it'll be if he has to back out, but he's thrilled at the discovery that he's more focused on the admittedly more tolerable nervousness about his tryst than his reluctance to get on the plane in the first place. What was once roiling fear in his gut is now excitement and anticipation, and that'll hopefully be enough for him to get through the flight without having a heart attack.

***

Monday arrives far too quickly. When Sam dropped him off at the airport mid-afternoon, he hugged Dean tight and bid him goodbye with a simple, "Good luck, man. You'll be fine. I promise."

Having the promise of his brother, who has never once let him down, makes him feel slightly better about the whole ordeal.

Dean navigates through the ridiculous, invasive maze of security, waits at his gate, then gets on the plane when they announce his boarding zone.

Everything is fine until the engines turn on, and the screens in front of all the seats start playing a safety video.

He swallows, and grips the armrests until his knuckles turn white, staring ahead of him, unblinking at the safety video and trying to memorize it.

The woman next to him in the window seat leans toward him. "Are you gonna be okay, sugar?"

Dean looks at her. She's an older black woman with a warm smile and a giant purse underneath the seat in front of her that's bigger than Dean's suitcase.

He gulps and tries to smile, to no avail. The engines are loud and the plane is full, and Dean doesn't understand how everyone can be so goddamn calm about this. They're about to be in the sky, for godsakes. "Yeah, I'll be fine."

"Have you ever flown before?" she asks.

Dean shakes his head, then he nods. "I mean, once, when I was a kid. I don't... I don't like flying."

She smiles at him. "I can see that." Holding out her hand, she adds, "I'm Missouri, and you're gonna be just fine. Don't you worry about a thing."

Dean shakes her hand, willing himself to quit trembling, and replies, "Dean," giving her the nicest business-class smile he can muster.

Sam's promise, Missouri sitting next to him, and the thrill that he's about two hours away from fucking a stranger in the bathroom directly behind him are the only things keeping him from getting off this fucking death trap and quitting his job. Learning cost spreads and ratios and sales techniques just doesn't seem worth it.

***

An hour later, Dean is still staring straight in front of him at the screen that's looping commercials and telling Dean about all the snacks he can buy and credit cards he can apply for.

He managed to survive takeoff only by retelling himself the entire plots of all six Star Wars films. Dean was halfway through Revenge of the Sith when the fasten seatbelt sign turned off and he felt like he could breathe again.

The flight attendant served him some water, which he took only to make the facade more believable that he would need to go to the bathroom soon.

He's never been good at lying.

Missouri is leaned back against her neck pillow, eyes closed and breathing deeply.

Dean checks his watch. It's almost go-time. He looks around, and everyone is relaxed, watching movies on their screens. He cranes his neck to see if anyone is going into the bathroom between business and coach. There's no line. Everything is completely still and silent except for the dull roar of the engines.

He unbuckles his seatbelt and stands, meandering as casually as he can to the lavatory, wavering on his feet when he realizes he's walking in the sky.

But he's okay. Because he's about to go fuck a stranger in an airplane bathroom for no reason other than to relax his poor, frayed nerves.

He gets to the door. The handle reads "Occupied," but, per the instructions he's read dozens of times in the past week, he knocks five times in the familiar pattern. He looks back and forth down the aisle for good measure. No one is paying any attention to him.

He receives two knocks in return, and the door flies open. All he can see are a pair of the most intensely blue eyes he has ever seen and the glint of a wide, bright grin before being dragged by his tie into the tiny stall.

Blue Eyes slides the door shut behind them and locks it, then drags Dean in for a fierce kiss.

Dean doesn't even have time to register what's happening before a hot mouth is on his own, tongue parting his lips and stubble scraping against his chin. The man is nearly as tall as Dean, and his fingers are already threaded in Dean's hair, a low rumble in his throat as he takes Dean's bottom lip between his teeth and tugs at it.

Dean breaks away, gasping, his hand on the man's chest. "Whoa, man. Aren't we gonna, I dunno, talk about this first?" He finally gets a good look at the guy and hot damn this dude is all manner of gorgeous, with messy black hair, those beautiful blue eyes, plush lips slightly parted, and a five o'clock shadow over a strong jaw. His muscles strain against his tight black t-shirt and Dean looks down to see a bulge in his jeans.

The man growls– literally growls– at Dean. "Is this your first time doing this?"

Dean looks up from his crotch to his face. "Well, yeah."

The man rolls his eyes and sighs. "Rule one: no talking, just fucking." Then he leans in and places a hand on one side of Dean's neck while covering the other side in rough, sloppy kisses. Muffled by Dean's throat, he adds in a low rumble, "There is no rule two."

Dean bites back a moan, and asks, "Can I at least have your name?"

"Castiel," he replies.

Dean supplies, "I'm Dean," then gasps as Castiel bites down on the sensitive flesh near Dean's collar. Castiel loosens Dean's tie and unbuttons his shirt with quick, deft fingers. He pries it open so that Dean's collar is popped, necktie dangling over his naked chest, and Castiel breaks away to admire him, biting his bottom lip as he thumbs over Dean's nipples.

"God, Cas..." Dean hisses.

Cas stops and meets Dean's gaze. "Cas?"

Dean arcs an eyebrow, and instead of replying, reaches down to unbutton Cas's jeans, letting his hands explore the hard, smooth muscles of his abs and back underneath is soft cotton t-shirt.

Cas sighs and presses their bodies back together, kissing Dean again, this time slower, deeper. He unbuttons Dean's pants and reaches his hand inside, stroking the length of his dick in his palm.

Dean gasps into his mouth at the firm touch, bunching the back of Cas's t-shirt in his fists as he jerks him, slow and loose, until his cock is fully hard and leaking onto his palm.

Between kisses, Dean asks, "Who's gonna bottom?"

When Cas replies, his voice is impossibly deep, gravelly in a way that Dean has never heard from another person, a vibration that starts from his lips and runs down his chest and straight to his dick. "I will."

"Oh," Dean replies, breath hitching. "Yeah, that works."

Cas separates from Dean and takes a packet of lube out of his pocket, then pulls down his pants and squats down in front of Dean. He tears open the package, coats his fingers, and puts one hand between his legs, sliding a finger into himself.

Dean unzips his pants the rest of the way and pulls his cock out, jerking it while watching Cas prep himself.

Cas stares at it, mouth open, face contorted in pleasure when he hisses upon adding another finger. He leans forward and licks the drop of cum beading at the tip of Dean's cock, and Dean groans, quiet, stroking himself long and slow while Cas teases his head with his tongue.

Cas takes over, swatting Dean's hand away and wrapping his own around Dean's shaft, pulling it into his mouth and sinfully, slowly flicking his tongue around it.

Dean cards his fingers through Cas's hair, careful not to pull too hard or fuck into Cas's beautiful mouth, because even though he wants to, he's not going to do that to a total stranger, as much as this particular one would probably be into it.

Cas groans around Dean's cock when he shoves a third finger into himself. Dean watches as he does it, body contorted and filling up every square inch of the tiny room, pressed against the door and shoving his hips down onto his fingers as his fingers drive back up into him.

Dean thinks he might come just watching Cas fuck himself open.

Cas pulls off of Dean and gently slides his fingers out, then stands and turns to face the mirror, bending over slightly, his back to Dean. He pulls a condom out of his pocket and passes it back. Dean takes it, unwrapping it and rolling it over himself, pumping his dick a few times while staring at both Cas and himself in the mirror, each looking rumpled and debauched.

With one hand on his dick and the other on Cas's stomach, Dean lines himself up with Cas's hole and presses in gently, then pulls back out. He pushes in a little bit more, and pulls back out again.

Cas is panting between clenched teeth, eyes closed, and Dean presses in once more, this time bottoming out all the way.

Cas lifts his hand and bites at the pad of his thumb to keep from groaning.

Dean feels him loosening up around his cock while he rubs Cas's chest with his hands, up under his shirt, and teases his nipples, pinching them between his fingers until Cas is writhing, squirming in Dean's grasp.

"Fuck me, Dean," Cas gasps out, pushing back, grinding against Dean and shoving his ass onto Dean's hips.

Dean doesn't need more instruction than that, so he pulls out and snaps his hips back in, making Cas choke on a stifled cry.

Dean continues thrusting into him, fast and hard and deep, getting such little leverage in the small room that all he can do is press his chest against Cas's back and grind into him. He digs his fingers in Cas's waist and rolls his hips against him.

Cas stands up straight and leans against Dean's chest, head tilted back against Dean's shoulder, the angle forcing Dean to hit Cas's sweet spot over and over, making Cas's breath stop on each thrust inward, tiny broken whines escaping his lips.

Dean wraps a hand around Cas's dick as he fucks into him. He's slick with his own cum, and Dean jerks him, fast and dirty, coating his palm in his wetness and jacking him in time with his own thrusts.

They stare at each other in the mirror, and Dean bites down on Cas's neck where it meets his shoulder. Cas gasps, and his mouth stays open as Dean fucks into him faster, his own breaths heaving and catching while he mumbles, "C'mon, baby, fuck... fuck, Cas, you're so fucking sexy..."

And everything is made so much hotter by the fact they're in a goddamn airplane, which Dean is reminded of when they hit turbulence and hear a dinging noise indicating that they need to fasten their seatbelts.

Dean stops abruptly, slipping back to the anxiety he felt when they were about to take off, tensed and willing it to abate, and rests his forehead on Cas's shoulder, trying to catch his breath.

"Dean," Cas whispers. There's an edge of concern to the word.

Dean lifts his head to look at him in the mirror.

"It's okay. That's normal. Trust me." After a short pause, he adds, "If you don't keep fucking me, though, I swear to god–"

Dean, instantly soothed by the deep blue eyes staring back at him and the strong body leaning against him, slams into him again, and Cas's eyes close, mouth open and making quiet, strained noises, as Dean grunts and presses into him, fucking him open above god-knows-which-state, this total stranger, in public, hot and sweaty and half-dressed, where they could both get in trouble and Dean could possibly get fired.

And Dean loves it.

Dean sucks Cas's earlobe between his teeth, and apparently that's Cas's hot button, because he almost lets out a loud moan, but Dean catches it, smacking a hand over his mouth just in time as Cas groans into Dean's palm.

Cas reaches up and behind them to cradle the back of Dean's head in his hand, forcing their bodies some how closer together, clothes soaking through with sweat, slicked skin making filthy, quiet slapping sounds as Dean's thrusts become fast and shallow.

"Oh god, Cas," Dean whispers, brushing the shell of Cas's ear with his lips, hips losing their rhythm, becoming erratic with the short pulls of his fist on Cas's cock. "Fuck, I'm gonna..."

He feels Cas's body tense all around him, and takes his earlobe between his teeth again, biting down gently, and Cas lets out a shout into Dean's hand as he comes into Dean's other hand, hot streaks landing mostly in the sink in front of them.

In the mirror, Dean watches the wholly filthy and wonderful sight of Cas's orgasm, feeling his ass clench around the base of Dean's cock as Cas trembles, falling apart in Dean's embrace, and it pushes Dean over the edge. He stifles a moan by biting down on Cas's neck as he fucks into him, fast and hard and dirty, rolling his hips and pressing against Cas's prostate, earning him another surge of cum out of Cas's dick, shooting out and landing on the mirror as Cas rides down the shuddering waves of his orgasm.

Dean continues stuttering his hips into Cas as he comes down from his own, then rests his head on Cas's shoulder. Slumped together, holding each other up, they catch their breath, Dean tasting the salty sweat of Cas's neck as he trails it up and down with small, open-mouthed kisses.

Dean pulls out of Cas slowly, then leans back against the opposite wall. "Jesus Christ, man."

Cas pulls up his pants and buttons them, then takes out a paper towel from the dispenser and cleans up the mess they made, asking casually, "So what do you do?"

Dean looks at him, still too obliterated to even think about putting himself back together. "Huh?"

"You're a businessman," Cas says, looking at Dean in the mirror before turning around and facing him. "What kind of business do you transact?"

"Now you wanna talk?" Dean asks, incredulous.

Cas smirks at him, and reaches forward to slide the condom off of Dean's waning dick, tying it off and shoving it into the little door of the trash can behind him. "No one can fuck me that well without piquing my curiosity. So what do you do, sexy businessman?"

"I'm a banker," Dean replies.

Cas buttons Dean's shirt back up as quickly as he unbuttoned it, and reaches around behind Dean to tuck it back into his pants.

Dean's brain is too fuzzy to comprehend this act, so instead, he asks, "What do you do?"

Cas looks up at him through dark, fanned lashes, and gives him a small, flirtatious smile. "I travel."

"But where are you from?" Dean asks, noticing for the first time that, while he can't place a specific accent, Cas doesn't sound decidedly American. His words are too enunciated and there's a lilt to them that changes the cadence from the average American dialect.

Cas shrugs, gently tucking Dean's dick into his pants and buttons them, then rolls Dean's tie back around his collar and folds the collar back down. He tightens and straightens the tie, then smooths out the wrinkles of Dean's shirt with hands, running them along Dean's chest and shoulders and arms, then trails them down to Dean's ass and rests there. Face inches away from Dean's, he smiles with a tiny shrug and replies, "Nowhere important."

Dean continues prodding, reluctant for this exchange to end even though they've now occupied the lavatory for an excessive amount of time. "Where's home though?"

"Don't have one. Everything I own is in a backpack underneath the plane." He gives Dean a long look, breaking away from groping his ass and lifting his hand to comb his fingers through Dean's hair so that it settles back to an approximation of how it was. Then he leans in and kisses Dean one last time, quick and warm and chaste, and steps back, holding out his hand.

Dean takes it, and Cas gives it a firm shake before saying, "This was fun, we should do it again sometime," and winking, turning away to slide open the door of the lavatory and step out, then closing it behind him.

Dean looks at his hand and the business card Cas had apparently slipped into it. He examines it, thumbing over the small, embossed lettering. It reads:

Castiel Novak
Person
(323) 790-4967