Work Text:
“Please, Dean. A big case came in at work and Jack’s field trip is today .” Dean, chuckles to himself at Sam’s desperation– he was never going to say no, but he likes to make his brother sweat.
“I guess I can take the kid to the pumpkin patch...” Dean fakes exasperation as his brother floods the other end of the phone with “thank you”s and “i owe you one”s.
Truth be told, Dean loves his nephew more than he thought possible. He’d do just about anything for the kid, even take off a day of work and spend it in a pumpkin patch with a bunch of six-year-olds.
Yup, even that.
And if he has to remind himself how much he loves his nephew as he squeezes into one of those shitty bus seats that the kid behind him is already kicking like he plays soccer for Team USA, that’s his business.
Dean settles into the corner, wedging himself as comfortably as possible between the cool window and the seatback. He’s just about found the right positioning when Jack stands up on the bench seat. Dean sighs before leaning forward to grab Jack's shirt casually, making sure he doesn’t launch himself off the seat, but not too worried overall– the kid has enough energy right now he could probably run through a brick wall. Soon enough Jack must find what he’s looking for because he jumps up and down on the edge of the seat and yells, “CLAIRE! OVER HERE!”
Dean figures this is probably where he should intervene, and all it takes is a stern “Jack” for his nephew to turn towards him sheepishly before carefully crawling his way off the seat. By the time he’s back on solid ground there’s a small girl in pigtails practically vibrating in the aisle next to where Jack and Dean picked their seat.
This must be Claire.
“Hi, Jack. Wanna sit with me?” She practically whispers it, apparently the shy counterpart to Jack’s precociousness.
“Uncle Dean, can I?!” Jack looks back at him with the same puppy dog eyes that Dean hasn’t been able to say no to since Sam was Jack’s age.
“Yeah, yeah, fine. More room for me.” Dean makes a show of putting his feet up on the bench seat and folding his arms behind his head. Jack starts laughing before grabbing Claire’s hand and leading her to the seat directly in front of him.
Claire pauses a second, “Actually, Uncle Dean, Sir, is it ok if my dad sits with you? I don’t want him too far away…” Dean has to strain to hear what she’s asking but gathers the jist all the same before Jack speaks up.
“Yeah, Uncle Dean, make room for Mr. Cas.” Jack uses his thumb to point over his shoulder. Dean’s eyes follow the motion to a man Dean didn’t realize was standing in the aisle for what must’ve been this entire exchange.
Dean’s eyes trail up the man landing on a soft smile and the bluest eyes he’s ever seen. “Oh– uh– yeah– of course.”
Jack and Claire have settled into their shared seat by the time Claire’s dad, Cas , slides next to Dean. It’s a tight fit and Dean finds himself overly aware of the way their thighs are forced together. He tries desperately not to be annoyed by the fact this man doesn’t seem nearly as affected by their proximity as he is.
Get a grip, Winchester. It’s not like you’ve never seen a hot guy before.
Dean’s tries to think of any sort of small talk, his mind going blank save for the color of the man’s eyes. He turns towards him to say something stupid about the weather and Cas smiles tightly back at him before leaning his head back against the seat in what Dean can only imagine is a sorry attempt at trying to sleep on the bus ride.
Guess that alleviates any small talk… or interaction at all.
. . .
Castiel is only a morning person for Claire.
Never would he be on a bus, sans coffee, at 8:10 a.m. for anyone else.
But for his daughter? Anything.
So that’s how he finds himself slid into the bench seat of a school bus with some stranger trying to catch even a second more of shut eye while the entirety of Mr. Edlund’s second grade class screams the words to a song he thinks is from Veggie Tales.
Deciding sleep was probably a pipe dream, Castiel shifts in his seat and rolls his neck before finally taking a look at the man Claire ordered him to sit by so she could spend the bus ride with Jack.
Claire may be his number one but he’s pretty sure Jack will win out over him every time .
His companion is fiddling with something on his phone giving Cas the opportunity to figure out who he is without interruption.
Who he is, is the most attractive man Castiel has ever laid eyes on.
Based on what Jack said, he’s also Sam Winchester’s older brother, Dean.
Castiel had heard the mom’s talk about the elder Winchester at PTA meetings and open houses, but had never had the chance to see the man for himself. They prattled on about the “godlike bachelor” who slept around but never settled down. Castiel often found himself rolling his eyes, sure all their descriptions were exaggerated– he knows better than most there’s always something more alluring about someone you can look at but not touch.
Now he’s wishing the first time he got to look wasn’t in such close quarters.
From the flannel shirt, to the rough, oil-stained hands and the holy jeans that lead to muddy work boots, he’s checking everyone of Cas’s proverbial boxes. Dean is all man. In every sense of the word he exudes masculinity that Castiel can’t help but find extremely attractive.
This also typically screams “straight” in flashing neon lights.
Castiel sighs to himself, resigned, causing the man to look up and meet his gaze.
If Cas thought he was a goner before, the kind, green eyes might as well be the nail in his coffin. He can’t help but stare.
Lucky for him, it seems Dean may be having the same problem– maybe that flashing neon sign was all in Cas’s own judgemental head.
“Uh… um… hi. I’m–”
“Hi, I’m Cas.”
They both find the will to speak at the same time and immediately look away, dissolving into awkward chuckles before making eye contact again. Starting over, Dean offers his hand in greeting with a warm smile, “Nice to meet you, Cas, I’m Dean.”
“I know.” Nice, Cas. Real subtle.
Anyone else may have been uncomfortable but a sort of cockiness spreads over Dean’s features that should be unattractive but just isn’t– probably because even after only a few seconds of interacting with the guy, Cas can tell it’s a mask.
“Oh you know? Bummer. Was hoping my reputation hadn’t preceded me.” Dean punctuates his sentence with a smirk and a wink and Castiel practically melts right then and there.
“Nothing bad, I assure you.” Cas flirts back. Maybe it’s not the most appropriate thing to be doing on a field trip but this pumpkin patch is almost an hour away and the day may be a bit more fun with someone like Dean to entertain him.
“And I’m sure it’s all true.” Dean rolls his eyes and his shoulders tense a bit. Cas can tell he thinks much less of himself than the rumor mill let on.
He’ll just have to help with that.
“As far as I can see, you’ve been undersold.” Cas smiles widely, unsure where this boldness is coming from but feeling comfortable in it thanks to Dean;s reaction.
Dean’s eyes practically sparkle at the compliment, looking more green than Cas thought possible against the soft red that’s begun to tint his cheek bones. The man turns his head down and shakes it as he blushes before looking back towards Cas mischievously, “Well then it seems I’m at a disadvantage because I’m positive I’d remember hearing about you.”
Cas’s stomach does something absolutely ridiculous at the blatant interest from the man he thought of as a stranger only minutes before. This isn’t like him, so openly flirting or even chit chatting with another chaperone, but it comes easy with Dean and Cas isn’t sure he could stop if he tried.
Whatever the connection, Dean must be feeling it too because they continue talking about everything and nothing for the entirety of the bus ride. Cas decides in the time they talk that he absolutely needs to keep Dean’s hearty laugh in his life no matter what the cost.
Cas is so overwhelmed by his developing crush that by the time they reach the pumpkin patch, he finds he’s forgotten why they were on the same bus to begin with. After checking to make sure Claire is still in one piece, Cas turns to ask Dean why he’s here instead of Sam when he’s interrupted by a loud whistle.
Mr. Edlund, now at the front of the bus, begs everyone to quiet down so he can announce the groups for the day.
Cas is embarrassed when he finds himself hoping to be paired with Dean like he’s in elementary school again just waiting for the seating chart in which he was put next to the boy he liked.
. . .
Dean glances quickly to the side as Edlund announces groups and, like a goddamn preteen, sneakily crosses his fingers in hopes that he and Cas are paired together.
He wishes he had it in him to be embarrassed.
The bus ride was much more enjoyable once Cas resigned to the fact he wasn’t going to be able to sleep– Dean meant to ask why he thought that was even a remote possibility he just never got a chance.
Because they talked about every other thing under the sun.
Dean can’t remember the last time he was so content just talking to someone, but with Cas it all came so easily. It was flirty, and comfortable, and they got along great. Dean checked for a wedding ring not seven minutes into their conversation and was pleasantly surprised to find Cas’s extremely long fingers ringless. Between that and the man’s ability to flirt, Dean is almost positive the universe just dropped his perfect man in front of him and made them bat for the same team. Not to mention Cas’s smile– not the shy one he gets after you compliment him, but the real gummy one that only comes out when he talks about certain things. Dean wants that smile in his life for as long as humanly possible.
Sam is never going to let him live this down.
How the hell was he supposed to focus on pumpkin picking?
Cas elbowing him brings him back to the present in time to hear the next group, “Sam and Castiel with Jack, Claire, Ben, Krissy, Ash, and Lily for group four.”
At first he feels deflated, jealous of whoever got paired with Cas, but when he doesn’t move off the bus Cas gives him a weird look. Dean’s confusion only lasts long enough for Jack to yell, “Mr. Edlund it’s DEAN not SAM . My uncle had to come instead of my dad because my dad said a big case came in at work.”
Dean snorts at Jack’s repetition of what Sam said to him on the phone and then leans over the seat to ruffle the kid’s hair affectionately.
Edlund nods, “Alright, Jack. Sorry about that.
Dean
and Castiel, please take your group off the bus.” Edlund is patient enough with the kids, but Dean doesn’t blame him for showing a bit of annoyance at the chaos of it all– let’s just say Dean’s glad
he
isn’t the one in charge of this entire bus. “Ok, group five…”
Dean is following Cas off the bus as Edlund continues calling off group names. Castiel must chaperone a lot because before Dean is even sure what to do next, Cas is already implementing a roll call and buddy system. Jack and Claire cling to each other for dear life while Krissy, Lily, Ash and Ben pair off girl/girl and boy/boy. Everyone seems to get along and Dean realizes that Edlund must put them with their friends on purpose.
The rest of the field trip is like some weird dream Dean didn’t know he wanted. Through the petting zoo and hayride, Cas stays closer to Dean than is technically necessary, but Dean can’t find it in himself to care. When Edlund dismisses the kids into the pumpkin patch so they can pick out their pumpkins, Dean goes to follow Jack and is abruptly stopped by a strong hand on his elbow.
“They’ll be fine, come with me.” Cas says it quietly and Dean can’t find it in himself to argue. Cas is clearly the pro at ths chaperoning stuff– Dean finding himself more preoccupied with making the crinkles around Cas’s eyes appear and therefore goofing off for most of the afternoon. They walk side by side through the pumpkin patch, every once and awhile taking a headcount but largely just talking about nothing. Dean finds out that Cas’s wife passed away when Claire was born and he’s been raising her ever since. He can relate, often raising Sam on his own while his dad went out on his nightly benders.
That’s when Cas reaches for Dean’s hand– a reassuring gesture that should startle Dean but actually feels like the first bite of warm pie settling in his stomach.
Soon enough, Claire and Jack find them and drag them to where they found practically identical pumpkins that are definitely larger than the allotted poundage. Jack turns on his dad’s puppy eyes and Dean is helpless to say no to the few extra bucks it’ll be to take home the bigger pumpkin. When he glances over at Cas, it looks like Claire is having the same effect and he can’t help but smile at how clearly devoted to his daughter Cas is.
They help the kids carry their pumpkin back to the farm and then haul them onto the bus. After finally getting the pumpkins situated in the seat with the two kids, Dean is happily surprised when Cas plops down on the bench seat next to him. He sighs loudly and goes off on some tangent about how he hates pumpkin guts and he just knows that “big ass pumpkin” is going to have a ton of them.
Dean speaks before he catches himself, “Maybe we can carve them together?”
Cas’s eyes sparkle and Dean has never been more grateful for his lack of social filter, “I’d like that.” The smile Cas gives after agreeing to see Dean again is enough to warm Dean for the entire ride home.
He wants to see that smile again.
Thanks to Jack, as they’re loading their pumpkin into the back of Baby, he gets to. “Uncle Dean, can Claire come over to play?”
Dean should probably ask Sam but his brain is screaming at the opportunity to extend his day looking into the bluest eyes he’s ever seen, “As long as her dad says it’s ok…”
Jack fist pumps before running the short distance to where the Novaks are wrestling to get Claire’s pumpkin into the backseat. Dean starts to walk over and only picks up the end of the conversation over the kids begging please please please at Cas, “Well, I suppose if it’s alright with Mr. Sam than it’s alright with me.”
Dean interjects before Jack can say anything, “Yup. All square. I was going that way anyway so I can drop them both off. Besides, looks like your backseat is occupied.”
Cas sighs, looking at the pumpkin that just barely squeezed into his backseat before smiling that smile and turning towards Dean, “Thanks, Dean.”
God, he has a beautiful smile.
“No problem,” he shoots his shot, “Uh… just in case something happens between here and Sam’s, I should probably, uh, have your number.”
“Of course, just in case.” The way Cas’ eyes light up as he hands over his phone is unmistakable and gives Dean all the courage he needs for what he says next.
“And, uh, since I took off for the field trip and Sam is watching Claire, it looks like we both have a free night…” Dean can feel the blush covering his cheeks, but he finds it’s rooted in nerves as he asks out the first person he’s genuinely wanted a shot with in years.
Cas looks a little stunned at first, but schools his features as a matching shade of red creeps up his neck, “I’d, uh, like that.”
Dean smiles, “Great, I’ll text you the address and meet you there after I drop off the kids?”
“Can’t wait.” The excitement in Cas’s eyes make them even bluer and Dean can tell, if tonight goes half as well as the field trip did, it won’t be long before he’s a complete goner.
He’ll have to remember to thank Jack for having a friend with such a hot dad.
Ok, maybe not in so many words, but the kid is a pretty good accidental wingman.
Dean drops the kids off, shooting Sam a you owe me one glance as he ushers the two first graders through the front door and races off to the Roadhouse.
The night goes even better than the field trip surrounded by first graders– go figure– and Dean finds the guts to actually kiss Cas goodnight.
Somehow, everyday after that is better than the first so it’s no surprise when Dean finds himself down on one knee on the next year’s annual field trip to the pumpkin farm.