Genre and/or Pairing: Dean Winchester/Castiel
Spoilers: none, it's an AU!
Warnings: schmoop, adorable kid!Sam
Word Count: 4,109
Summary: Mr. Milton’s favorite student has an enthusiasm for drawing terrifying monsters -- in vivid finger-paint detail. Concerned for Sam Winchester's 4-year-old psyche, Mr. Milton schedules a parent-teacher conference. Part 1 in the Once Upon a Wendigo verse.
It’s the third week of the school year and Castiel has finally settled into a comfortable routine with his students. Mondays have been designated as “Art and Culture” day and the children enjoy funneling their post-weekend energy into various arts and crafts. This Monday is no different. As soon as Castiel lays out the various art supplies, eager hands swoop in to pick and choose their favorite colors of construction paper, pipe cleaners, and paint. Sam Winchester grabs several cups of red paint and runs back to his seat.
“Indoor speed,” Mr. Milton warns.
Soon the sounds of snipping scissors and wheezing glue bottles can be heard throughout the classroom. Castiel likes to begin Mondays by instructing his students to create a visual summary of their weekends using any medium of their choice. Kevin Tran, his TA, sets up the easels for the students that wish to paint while Castiel brings out a small stack of plastic aprons from the supply closet.
Once the students are settled and working, he makes his rounds slowly and observes everyone’s progress. Most students, artistically inclined or otherwise, have shown improvement in both skill and enthusiasm. He spots Jessica Lee Moore making a rabbit out of pipe cleaners and mentally notes to make sure none of the wires' sharp edges are available to little hands. Ed Zeddmore and Harry Spangler huddle close together as they build little director’s chairs out of popsicle sticks. Castiel is helping Ruby Talbot locate a pair of lefty scissors when Sam accidentally drops a cup of red paint all over his shirt.
“Sam, where is your apron?” he asks as he makes his way over to assess the extent of damage to Sam’s clothes.
Sam looks up innocently. “I forgot it.”
“Now, Sam, remember the rules: when we paint--” Castiel’s gaze strays toward the easel and he stops mid-speech. “Sam,” he asks gently, “what are you painting?”
The painting in question is the latest addition of what Castiel is beginning to refer to as “worrying weekend summaries.” The painting is done entirely in black and red paint depicting a monstrous, vaguely humanoid creature looming in what appears to be a cave. It is surrounded by an inaccurate representation of fire, its clawed hands pointed up like it’s writhing in pain.
Sam follows Castiel’s gaze and calmly replies, “A wendigo.”
Castiel has no idea what in the world a wendigo is, so instead he nods in agreement and steers Sam into the washrooms to help him change into his spare clothes. The moment he gets a chance, he schedules an appointment with Sam’s guardian to have a talk.
It's not the first time Sam has painted...interesting creatures. In the first week of school, Castiel witnessed Sam’s interpretation of a werewolf, and just last week Sam’s vampires had made him pause in worry. The vampires were as terrifying as they were inaccurate, their fangly mouths twisted in horror as a man chased after them with what Sam identified as a “really big knife!” Now with the newest addition of this wendi-whatever, Castiel has detected a pattern -- a pattern that requires administrative action.
The worst of the situation isn’t even the fantastical beasts coming from Sam’s imagination. It’s that the paintings are so graphic, so violent in nature, that Castiel cannot display his artwork in good conscience. As long as Sam’s theme continues, his work will never appear on the “Art of the Week!” wall, and Castiel’s heart twists at the look of pure dejection on Sam’s face when Fridays roll around.
Well, I'll just have to change that, Castiel decides.
Dean doesn’t hear his phone go off during his mid-morning class, but he feels it vibrate in his pocket. He feels it vibrate again a few minutes later and makes a mental note to check his voicemail as soon as he’s done teaching. Dean hopes it’s the electrician. The house has had some issues with the wiring and last week when he plugged in the vacuum, sparks flew. Dean needs to get that checked out before he accidentally electrocutes himself, or worse, before the house goes up in flames. He also needs to make this week’s grocery run and Sam needs new clothes for the fall. Sam’s growing like a weed and his last winter’s coat doesn’t fully cover his torso anymore, the sleeves barely reaching his wrists.
Which reminds him, the Impala’s been making a weird clunking sound and Dean needs to check his baby over pronto.
Dean sits on the edge of his desk and crosses his legs at the ankles. “According to last night’s reading, who can tell me the classic signs of the presence of a ghost?” The semester has just started and Dean doesn’t actually expect his students to be in “school mode” just yet, but he still likes to weed out the slackers. Besides, he’s not exactly known as an easy professor, quite the opposite in fact. “Professor Winchester is a hardass and if you slack in his class, he will ride your ass until kingdom come -- not that you’d mind, Winchester is fine!” Oh yeah, Dean knows all about his profile on RateMyProfessor -- and Professor Winchester is HOT. By the looks on his students’ faces, he’s pretty sure they’re all well aware.
There’s a furious rustle of flipping pages as the usual suspects shoot their arms into the air. “Someone new. Someone who hasn’t done the reading, preferably.” His eyes survey the room. “You, the one in the hoodie avoiding eye contact.” The frightened student in question looks like a deer caught in the headlights. Dean smiles charmingly, but it belies the shark within. “Time to dazzle me with your brilliance.”
“Uh...” the student begins, “y’know. Flickering lights?”
As his students file out, Dean collects his papers and bag and heads back to his office, a converted supply closet on the second floor of the English Department. The room is just large enough to squeeze in two bookshelves, a desk, and two chairs on opposite sides. It’s a little cramped, but it’s a better scenario than when he shared an office with Professor Henricksen. They had come to the conclusion that while they could coexist, they could definitely not cohabitate.
Dean dumps his shoulder bag and miscellaneous papers onto his messy desk before plopping into his chair, the seat swiveling under him. He pulls his phone from his jeans and scrolls through the notifications. He has one missed call and one voicemail. The missed call is from Sam’s elementary school, which is odd considering the voicemail in his inbox is definitely from a sex line because hello, Dean would not mind more of where that gruff voice came from, please and thank you.
The voice self-identifies as Mr. Milton, the name of which Dean recognizes from the “Congratulations! Your child has earned him/herself a spot in our prestigious kindergarten!” letter he had received in the mail a few months ago.
Aside from the totally hot sex voice, the message is simple and requests that he call back immediately to schedule a parent-teacher conference. That in itself is worrying because Sam’s not the trouble-making type. Well, not yet anyway. Dean may be a professor, but he was a student once and can still remember all too well the brand of trouble Winchesters tend to attract. What if Sam beat up some kid? Or worse, what if Sam’s the one who got beat up? He didn’t raise a bully, but he didn’t raise a pushover either, and Dean really doesn’t want to explain why Sam knows how to throw a solid punch.
Then Dean’s mind starts to race. What if it’s not about a fight at all, but something more serious? What if Sam’s sick? What if he accidentally swallowed something? What if he’s developed an allergy to something, like his peanut butter sandwich? Maybe Dean should switch to turkey? But how would he get Sam to eat it? The school would tell him if Sam needed hospitalization. Right?
Dean is supposed to have office hours until an hour before Sam’s out of school, but he cancels them with a handwritten note on the outside of his door. He’s capping the black marker with his teeth as he calls the elementary school to confirm his attendance later that afternoon. Whatever this is about, it’s getting settled today.
Castiel is facilitating “Clean Up Time” at the end of class when he receives confirmation from the main office that Sam’s guardian, Mr. Winchester, will be meeting with him within the hour. Castiel thanks the secretary, a plump jovial woman named Missouri, and hangs the classroom phone gently in its cradle. He’s pleased Sam’s parent responded promptly. It showcases a healthy family environment and a serious investment in the child’s education. A voice nags at the back of Castiel’s mind. If Sam comes from a good, loving home, where is his gruesome imagination stemming from? Something smells fishy.
Castiel collects various nearly-empty bottles of tempera paint and places them on a tray. He calls Sam over and hands him the tray. “Will you help me put these away in the supply room?” Sam nods and they head toward the back of the classroom through a door where they keep everything from supplies to the spare clothes the children sometimes require.
It is one of the most well-stocked closets Castiel has ever had the pleasure of using. The tuition alone for the small private school keeps the classrooms stocked, the campus clean, and every piece of technology updated to the latest software. Add in generous contributions from private donors and Castiel has the best salary he’s had in years.
“How did you enjoy art time today, Sam?” Sam holds the tray of paints while Castiel plucks the containers and sorts them away.
“I drew a wendigo on fire,” Sam boasts, puffing his chest proudly. The tray tips forward and one paint container falls to the floor with a thump.
“Do you like wendigos?” Cas asks conversationally as he stoops down to pick up the bottle of tempera paint.
“They’re really cool! When they die, they make this sound!” Sam pulls in a large breath of air and screeches.
Kevin runs into the storage room in a panic. “What’s happening??”
Castiel feels like he just lost a year off his life. He unclenches the fist over his heart and smoothes out his cardigan. “Nothing, everything’s fine. Sam...he’s feeling very energetic today.”
Sam smiles, rocking back on his heels. Kevin leaves with a wary glance over his shoulder as Castiel takes the tray from Sam’s little hands and kneels down. “Sam, I called your father and he’s going to come talk to me about your paintings. How do you feel about that?”
Sam’s eyes widen. “Am I in trouble?”
Cas pets the top of his head in a reassuring gesture. “No. In fact, you can play with the puzzles while we wait for him to arrive.”
“As soon as your classmates leave for the day.” Castiel pushes off his knee and stands. “Now go finish cleaning up with your friends.”
They don’t have to wait long before Castiel hears footsteps approaching. He leaves Sam hunched over his puzzle, tongue poking out of the corner of his mouth in concentration, and meets Mr. Winchester a few feet outside the classroom door.
A man about his height, maybe an inch or two taller, slowly approaches him. He’s bowlegged, Castiel notices, and he’s wearing pants that are snug around the bum. The material looks rough, raw denim with a dark wash. They look expensive. He’s walking casually, the rest of his tanned body sporting a well-fitted plain grey t-shirt, biceps clearly visible.
“Hi,” he smiles, “you must be Sam’s teacher, Mr. Milton.” The man extends his hand in greeting, and Castiel takes the offered hand in a firm handshake.
“Mr. Winchester,” he acknowledges with a nod. “Thank you for coming.”
“Oh, you can just call m--”
Thunderous little feet interrupt as Sam launches himself at the newcomer. “DEANNNN!”
“Hey there, Sam-squatch!”
Castiel watches as “Deannnn” scoops Sam up in an effortless one-armed embrace, holding him firm around the waist. The affection is easy and familial, but Castiel doesn’t know of any children who address their parents by their first names. Perhaps this is one of those new age parenting styles, the ones about equality between parent and child. Dean certainly looks young enough.
Unless this isn’t Sam’s father after all. An older brother, perhaps?
“I heard you talking to Mister Milton! Did you come to see my drawings? Mister Milton says they’re really good! Today during art time--”
Dean breaks Sam’s long-winded monologue and places him on the ground. “Alright, sounds great, Sammy. Why don’t you go work on your homework or play with some of the toys inside while I talk to your teacher?”
“I was doing a puzzle!” Sam protests.
“That’s awesome, dude. Think you can finish it before we go?” Castiel hears the challenge in the question, and by the way his face locks in determination, Sam does, too. Dean fistbumps Sam and turns to Castiel.
Dean’s bright green eyes shift beneath long eyelashes as they follow Sam as he disappears into the classroom. His gaze reveals a deep fondness for the toddler, and his shapely lips quirk in a proud grin. When his attention shifts back to Castiel, the soft expression hardens a bit, his back straightens and his broad shoulders lend to an already imposing form. It makes for quite an attractive sight.
“So you asked to speak about Sam, Mr. Milton?
Castiel nods. “He’s not in any trouble, if that’s what you’re worried about. Your son,” Castiel fishes, “ is a pleasure to have in class. All the other students get along with him very well.”
The fight bleeds from Dean’s tense frame. “Damn straight he’s a pleasure,” he snorts, clearly smug. “So what’s this about?”
Daddy Winchester, then. Figures, Castiel rues dramatically. A man that handsome is not only married, but microchipped -- and only because keeping him under lock and key might arouse the suspicion of the neighbors.
“Well,” Castiel begins, “I’m a little concerned about Sam’s creative outlet.” He licks his lips, chapped from the cold and dry weather. “As I’m sure you’re well aware he has quite the imagination, the nature of which is disturbingly graphic for a boy his age. He’s a talented artist, but I’m wondering as to where he might be getting his ideas.”
Dean’s blank stare conveys efficiently that actually, no, Dean has no idea what he’s on about.
“He paints extremely vivid pictures of monsters and creatures,” Castiel says deliberately, as if Dean’s acting purposefully obtuse. At Dean’s persistent blank look, Castiel sighs. “Perhaps it’s best if you see them for yourself.”
Mr. Milton leads Dean inside, a cheerfully painted classroom with large glass windows decorated with patches of brightly colored tissue paper. The rendered effect is that of a DIY stained glass project. Sam is sitting on the floor in a far off corner, next to a pile of beanbag chairs thrown haphazardly in a heap like a patch of overgrown pumpkins. There are bookshelves everywhere laden with everything from picture books to legos to toy trains and make-believe phones.
Mr. Milton’s desk is off to one side, angled so that it faces a majority of the classroom. The desk is practically bare, only the essentials crowding in a corner along with a framed picture of a very grumpy cat. A smaller desk is situated close by with a handmade nameplate that reads, “Kevin.” Once at his desk, Mr. Milton rifles through his files and lesson plans to pull out Sam’s paintings. They’re all saved in a yellow manila folder, presumably kept filed away from young and impressionable eyes. Dean looks on as the paintings are spread out over the desk, the paintings little more than a large mass of black and red paint.
“Sam said this one was a werewolf,” Mr. Milton says, pointing to the aforementioned painting and disrupting Dean’s thoughts. He points to another. “This one is a vampire. And this one,” he points to one that is still slightly damp, “this one happened today. It’s a wendid-- a wedido-- an I-don’t-know-what.”
Dean valiantly suppresses his growing amusement. “A wendigo?”
Mr. Milton turns his gaze to Dean in suspicion. “Yes. That.” He drops his eyes back to the paintings. “You have to understand, Mr. Winchester, these images are very violent. I’m worried about Sam’s mental well-being.”
Dean can’t help himself. Sam? Mentally unbalanced? He ducks his head and tries to stifle a laugh.
“I suppose you find this amusing?” Mr. Milton’s tone is lethal. “It’s always such fun when your child exhibits early signs of emotional trauma.”
“Look, Mr. Milton,” Dean holds his hands up in mock surrender, “this all has a very logical explanation.”
Mr. Milton’s glower reeks of ‘I am an educator and therefore you should show me some respect.’ Were Dean a lesser man, he might be cowed into submission, but Dean’s an educator, too. A menacing glower is Teaching 101. Mr. Milton’s staredown is solid, his pretty blue eyes adopting a sharp edge, not dulled through the lenses of his rimmed glasses. It’s really kind of hot.
“I’m an English professor down at the university.” At Mr. Milton’s unimpressed stare, Dean falters. “I’m teaching Supernatural Mythology in American Literature this semester,” he offers. “Urban legends make their way in, too.”
Realization dawns on Mr. Milton’s face, but is quickly replaced with righteous indignation. “You think this,” Mr. Milton whispers incredulously, gesturing wildly toward the paintings, “is suitable material for a four year old?”
“Oh, come on,” Dean complains, “it’s like ghost stories!” He pauses, then adds devilishly, “Or, you know, like stories from the Bible. No one ever complains about those.” At Mr. Milton’s ungiving stare, Dean huffs. “Okay.” He turns to Sam who is still diligently working on his puzzle. “Hey, Sammy, are wendigos scary?”
Sam looks up from his puzzle and shakes his head. “Nope.” Then, in the same tone adults adopt when telling their children yes, there is such a thing as goldfish heaven, Sam adds, “you can kill them with fire."
Dean snorts. “Yeah, if they were real.”
Once Mr. Milton has been sufficiently assured that, no, Sam is not under the impression that these monsters are real, does he finally allow the conversation to stray toward friendlier topics.
“So...” he begins lamely. “You’re a professor?”
“It’s not as glamorous as it sounds,” Dean laughs, “but I’m sure you know that.”
“Teaching is its own reward,” and Mr. Milton winces at how Chicken Soup for the Soul it comes across. Dean’s reaction is to throw his head back and laugh.
“Whatever, Buddha. You teach four year-olds. Any wisdom you dish out doesn’t get any deeper than ‘look both ways before you brush your teeth.’” At Mr. Milton’s responding chuckle, Dean turns sheepish. “That didn’t come out right.”
Mr. Milton flashes a real smile at that and Dean feels himself unconsciously lean forward in his seat. ‘Mr. Milton’ looks to be around his age, maybe a year or two older, and now that he’s relaxed and chatting, Dean can see why all the mothers titter about this particular man at the school gate. He’s attractive--and how so--and either oblivious to his good looks or completely unconcerned with the fact.
Despite the fact he works with messy children, Mr. Milton is clad in a nice pair of charcoal slacks and a button down shirt he’s tucked into the waistband. He is sporting a simple brown leather belt, accentuating his narrow hips. His body is lithe, but toned. Behind him, his cardigan is slung across the back of his desk chair along with a tan colored trench coat. His sleeves are rolled up to his elbows, revealing lightly-muscled arms, but Dean takes most pleasure in the shape of his hands. They’re the hands of honest labor, strong and firm, but the paint under his fingernails tell of a gentler occupation. They’re gorgeous.
They’re also conspicuously ring-free. Perfect.
“So, Milton. Is that...British?” Dean fishes, leaning his elbow on the desk, his grin dangerously charming. The intent is not lost on Mr. Milton whose eyebrows shoot up in surprise.
“It’s just very old,” he admits. “And Castiel is fine.”
“It’s from the Bible,” Castiel informs him, answer rote.
“Dare I ask?” Dean teases.
“That would be your prerogative,” Castiel supposes, “but it is perhaps a conversation better suited over dinner and drinks.” It’s delivered nonchalantly, but Dean detects a definite lilt in his cadence, turning the statement into a quiet, hopeful question. Hell yes.
“Maybe this Fri--”
“Deeeeaaannn, I’m hungry,” Sam whines suddenly. Dean and Castiel snap apart, their hands caught in the proverbial cookie jar. Sam abandons the puzzle and climbs onto Dean’s lap, looking up imploringly as Dean’s arms instinctively hold him in pace. “I want lasagna.”
Castiel pushes off the desk, his wooden chair struggling against the carpet. The moment is lost and he begins to collect Sam’s paintings in a flurry of nervous energy.
“Well, I believe the matter has been settled. Thank you for seeing me today. Sam’s a wonderful student, a true all-around joy to have in class.” He places the paintings back in the manila folder and holds it out to Dean. “I believe you’ll want these?”
Dean tucks the folder under his arm and ruffles Sam’s floppy hair. Sam’s expression is mutinous as he preens his hair back into place. Sam’s mood is quickly descending into the depths of Dean’s personal hell. Here comes prissy pants. Time to go, he thinks.
“Alright Picasso, we’re going home. Say goodbye to Cas--Mr. Milton.”
“I don’t wanna go home, I want lasagna!” Sam kicks a leg against Dean.
“Sam,” Dean says sternly, to little effect. He turns his attention back to Castiel and shoots him a commiserating smile. “Sorry. Little brothers, am I right?”
“I’ve seen my fair share of temper-- wait, what?”
Castiel is shocked and Dean quirks his eyebrows in response. “Did I say something weird?” His expression is meant to appear genuinely bewildered, but its execution is compromised by Sam, who is making pitiful noises and pulling at Dean’s face.
“You're not Sam’s father?" Castiel blurts, sans filter from brain to mouth. His brain throws up a red flag, but it’s too late.
Dean doesn’t bat an eyelash. He gets this all the time from people who see him and Sam together. Of course Castiel would be under the same impression. It’s an honest mistake: Sam’s young, Dean’s of parenting age, and they’re clearly related. Dean doesn’t mind rectifying the misunderstanding. He opens his mouth to answer, but doesn’t get a single word in edgewise as Sam chooses that exact moment to stick as much of his hand as he possibly can into Dean’s mouth. And because Sam is a punk, he volunteers his version of the truth.
“Nope, Dean’s my brother and he’s bi--,” Sam struggles with the pronunciation, “bi-sensual.”
Dean literally pulls Sam’s hand out of his face. “Sammy!”
“That’s what Uncle Bobby told Aunt Jody!” Sam chirps.
“That is not what Uncle Bobby told Aunt Jody,” Dean grits through his embarrassment.
Castiel huffs a laugh, heartened by Dean and Sam’s bickering. “Well that’s good to know.”
Dean fumbles. “What’s good?”
“Dean,” Castiel smiles, “may I ask you out to dinner?”
As Dean and Sam make their way to the car, Sam makes one final stand for dinner.
“Are we getting lasagna now?” he demands, hanging like a limp noodle in Dean’s arms.
Dean shifts Sam onto one arm as he fishes for his car keys. “You’re getting yesterday’s veggie loaf.”
Sam gives up, deflating into his car seat. “Okay.”
Dean buckles him in with a practiced ease. “Maybe next week, kiddo.”
The week has started off on a good note. The students in his class are actively interested in the course material, Sam’s not in trouble, and he’s even got a hot date lined up on Friday.
Dean looks back to the elementary school and lets out a deep breath. It’s been a long time since he’s gone on a date; it’s been even longer since he’s dated. Sam is his first priority and raising him solo has been a full-time job. Everything else has been on the back burner ever since--
--anyway, it’s not like he’s thinking of dating Castiel. He’s Sam’s teacher for crying out loud.
It’s just one date. One really, really hot date.