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Let's Fly Way Up to the Clouds

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Captain Martin is wiping champagne off his face in the airplane bathroom. That damned steward, he thinks, that damned incompetent steward. He’s gonna get it. He checks his watch and sees that it’s only an hour until they land. He’ll get him then, he doesn’t mind waiting; he doesn’t know how, but he will. Dean opens the bathroom door, peeking out and looking left, then right, to make sure he can effectively avoid his inept coworker. He doesn’t see him anywhere-- thank god-- and strides down the aisle. He opens the door to the cockpit and enters, thinking he’s safe, but no, there, in all his idiotic glory, he is.

“Why are you in the co-pilot’s chair, pal?” Dean asks, his voice on the edge right before actual anger; he was cool, but not that cool.

“The co-pilot wants I should sit in for him while he has a few drinks,” the kid replies, looking up at Dean with round eyes.

“And where’s the navigator,” Dean asks, really about to go over the edge.

“I think they’re together,” the steward responds, and Dean wonders how they could’ve been stupid enough to leave this little idiot in charge of the whole plane.

“You know what you’re doing?” Dean asks, sitting down in the pilot’s chair, “You know where we’re going?”

“You think they’d send me on a plane if I didn’t know how to use it? You think I can’t fly? You think I don’t know what’s going on around me?” the kid asks, indignant.

“Well,” Dean says, raising an eyebrow at him, then turning to check the plane’s map, “Do you?”

“No.” the steward replies.

Dean’s exasperated. He exhales sharp through his nose, and sees they’re hours off course. He swears he’ll fix this silly boy’s wagon. He could just about whack him right now. The steward puts a hand on Dean’s which surprises him.

“Look, Captain Martin, I wanted to say I’m real sorry,” the kid says, which surprises Dean even more, but also makes him slightly more irritated.

“Pal, we’re off course by hours, you’ve desecrated my plane, and all you say is you’re sorry?” Dean says, trying to ignore the feeling of soft, warm fingers on his skin.

“I know that, and I said I was sorry, Captain,” the steward says, and scoots up closer to Dean.

Dean steals a glance at him, at his medals and his full lips, which are pouting now, and his furrowed together eyebrows. He thinks of the kid introducing himself, referring to himself as his stewardess, and feels a jolt of warmth in his stomach. He tries to disregard it; he’s so mad at this bothersome, idiot boy. He swears it.

The kid pushes it, and he speaks again.

“Is there any way I can make it up to you, Captain?” he practically purrs, and rests his head on Dean’s shoulder, snuggling into it; Dean feels his nose rub on him through the fabric.

“I don’t even know your name, kid,” Dean says weakly, his resolve trembling as he steers the plane back on course.

“Jerry,” the kid replies, and rests his sharp chin on Dean’s shoulder, boldly pressing his full lips to the veritably un-stoic Captain’s neck for a kiss.

“Jerry,” Dean practically whines, “Cut it out.”

“Really?” the kid pulls away, and he sounds so disappointed that Dean almost feels bad.

Dean looks back at the kid-- Jerry-- and sees that he’s taken his hat off; he’s got closely cut hair that looks fun to mess up, and his eyes flick down to those lips that look so soft, like they’d feel good on his… Dean pulls his glance away and looks at the controls pointedly.

“I hate to upset you, Captain,” Jerry says, “I don’t like upsetting people in charge.”

“Only when they’re handsome, though?” Dean quips (maybe he’ll play with the kid a bit, why not), “You’re coming onto me like a runaway train, pal.”

“You want I should leave?” Jerry says, and his voice sounds genuinely disappointed, “If it’d make you feel good to be left alone, I’ll leave you alone.”

Dean thinks on it, he really does. He looks at Jerry, whose eyes are glistening, and whose cheeks are pink with blush despite this fact, and then looks at the plane controls. He figures the co-pilot and navigator have cleared out for good; they’re probably drinking the whole liquor cart without him, those bastards.

“No, kid, I think you should stay,” Dean says, hoping he doesn’t regret this, then adds, before he can really regret his actions, “Since you’re my stewardess after all.”

“Oh,” Jerry says softly, and scoots up next to Dean, just as the pilot cups Jerry’s face in his hand.

He runs his thumb over the kid’s bottom lip, over the divot in his chin, and Jerry stares at him with wide eyes, as if he’s completely shocked, but as if his day’s also being made.

“My stewardess,” Dean says again, firmly, then tacks on a question “All mine, huh?”

“Yes, Captain,” says Jerry, then flutters his eyelashes, “I want to make it up to you so bad.”

“You got pretty lips, you know,” Dean responds, then kisses the kid right on the mouth.

Jerry throws his arm around Dean’s shoulder, pulling himself into the pilot’s lap. Dean hits the autopilot switch, hoping it’ll work well enough for enough time, and holds Jerry’s hips in his hands. Jerry slips his tongue into Dean’s mouth, kissing like he wants to eat him up. Dean grabs his shoulders and pushes him away a bit, holding him in front of him. Jerry looks dazed and his pretty mouth is shiny; Dean thinks that he’d look good in lipstick; he’d look pretty dressed up like a real stewardess.

“Captain,” Jerry says, smirking a little, “I dunno what you’re thinking about, but you’re sure hard, boy.”

“You want me to tell you?” Dean raises an eyebrow, “You really wanna know, kid?”

Jerry nods, and shifts so his thigh rubs across Dean’s cock. Dean lets out a sound he’d describe as ‘awfully embarrassing’ if asked.

“Well,” Dean says, unbuttoning the kid’s jacket leisurely as he talks, “I was thinkin’ about you dressed up nicely, you know, like a real stewardess.”

“Like a broad?” Jerry asks, blush rising in his cheeks.

“Mhm,” Dean says, getting to the jacket’s last button and throwing it aside, then sliding his hands up under the white undershirt.

“You want I should do my lips up for you? All red and lovely for my Captain?” Jerry asks, flicking his tongue out of his mouth, smirking when he feels Dean’s cock twitch up against his leg, “And wear pretty stockings? With the straight seam up the back so it’d be easy for you to keep those big brown eyes on my legs? You wanna crash the plane, bubbe?”

Dean laughs at the last statement, and Jerry raises his arms up so he can pull his undershirt off him. After it’s discarded, Jerry looks down at the big hands resting on his waist.

“It’d be easy for you to push me around; look at the size of those hands,” Jerry says, softly, running his over Dean’s.

“I like that,” Dean murmurs in reply, “And I like when you call me Captain. And I’d like seeing you dressed up like a dame.”

Jerry mock pouts, “That’s not a nice name to call me, Mister.”

“You act like one,” Dean shrugs, “Besides, I bet you’re hard up for it, aren’t you?”

“Put that big hand there and feel for yourself, Captain,” Jerry says, then smooches Dean on the tip of the nose.

Dean rubs the palm of his hand against Jerry’s cock, and Jerry bites his fist to keep from being noisy.

“Is it really that hard to be quiet?” Dean teases, “I’ve only just started… You really do act like a broad.”

Jerry can’t muffle the bone deep groan he responds with, and can barely muffle the whine he lets out when Dean slips a hand down his pants. He feels the warm, big hand clutching at his cock through his boxers, and then it comes out; he’s about to whine again, but notices Dean’s undoing his pants. Jerry watches with bated breath as Dean pulls the pants down to his mid thighs and fetches his cock out of his boxers. Dean wraps a hand around it, and Jerry’s cock isn’t small by any estimate, but Dean’s hand is just so big… Jerry’s blushing again and buries his face in Dean’s neck.

Dean strokes a few times, then gives his cock a squeeze then says, “I thought you wanted to make me feel good. To apologize for what a bad job you’ve been doing all night.”

“Oh, oh, Captain, I do,” Jerry whines, squirming because Dean really is squeezing it.

“So what are you gonna do? You gonna get down on your knees for me?” Dean asks.

“Please,” Jerry says, “I want to, I want to.”

“You want it more than any woman I’ve ever met, even ones I paid,” Dean says, and Jerry’s cock twitches in his hand, “What, you like being easy?”

“Only for the handsome ones,” Jerry mimics Dean’s earlier jest, and slips out of his lap to get between his legs.

“Take the pants off, kid, you don’t need ‘em for anything right now,” Dean dictates, and Jerry nods, letting them fall and stepping out of them.

Dean likes this full view of the kid; he’s young and skinny, but he’s got a carpet of chest hair that Dean wants to pet his hand up against. What’s more, Jerry was right; he would look distractingly good in stockings. He’s got surprisingly lovely legs, and his ass is to die for. Dean swallows loudly as the kid gets between his knees. Jerry unzips Dean’s pants and fetches his cock out, and, oh, the feeling of those warm, soft hands is like heaven.

“It’s big,” Jerry says, dumbly, and Dean laughs again.

“What’d you expect, kid?”

“I expected big,” Jerry’s blushing, “It’s just real nice to hold, is all.”

Dean’s going to respond, but then Jerry slips those delectable, lovely lips onto his cock without missing a beat. It’s even better than he thought; Jerry’s looking up at him, through dark eyelashes, with big hazel eyes filled with adoration, half lidded. He takes Dean in his throat, so easy, and Dean’s cluttered thoughts organize enough to marvel at how much like a real stewardess Jerry is, and how fucking nice it would be to see lipstick smear off the kid’s full lips, all over his cock. He looks down between Jerry’s legs and sees the kid’s forearm tensing as he strokes himself, too. Jerry likes sucking him off, and that makes Dean sure he’s not going to last too long.

Dean buries his fingers in the short hair, and grips as best as he can. Jerry’s sounds vibrate on his cock, and it seems the faster and harder Dean pushes into the kid’s mouth, the more sound he makes.

“Not gonna last long,” Dean mumbles out, “Gonna do it in your pretty mouth.”

Jerry’s eyes drop shut and he moans again, so Dean responds, “You want that? You want to swallow for me?”

Jerry flicks his tongue over the head of Dean’s cock, tightens his lips even more, and, God, Dean’s cumming, wedged down the kid’s throat. It hits him so hard he sees stars, warmth flooding through his insides, and he holds Jerry in place, feels the kid’s throat tense, and lets him go after slightly too long. He watches Jerry’s neck; he sees him swallow, and the kid leans on one hand, locking eyes with Dean. He strokes himself once, twice, three times, and cums on his own hand and stomach. Jerry slumps against Dean’s leg, resting his cheek on his knee as he catches his breath. Dean’s tired and spent, but he can see how good the kid’s swollen lips look.

“All better now, bubbe?” Jerry asks, then smiles tiredly, “Ya like me now, even though I screwed up your flight?”

Dean pets Jerry’s head, and smiles begrudgingly, “Yeah, you idiot, I like you a lot.”