intheperiphery (intheperiphery) wrote,

Chasing Tail

Rating: PG-13
Genre and/or Pairing: Dean Winchester/Castiel
Spoilers: none, it’s an AU!
Warnings: schmoop, adorable kid!Sam, temper tantrums
Word Count: 9,207
Summary: It's mid-September and Friday's finally here. Professor Dean Winchester and Mister Castiel Milton bond over a mutual love of juicy burgers and making out in the Impala. A second date might be in order. Part 2 in the Once Upon a Wendigo verse.

Authors’ Note: Thank you for your wonderful feedback! If you’re just joining us, you don’t need to read Part 1, but it helps get your bearings on this wonderful universe we’re creating. You can read Part 1 here. Hope you enjoy and let us know what you think!


Dean’s alarm goes off at 6 o’clock sharp.

He stumbles out of bed and into the bathroom, hands on autopilot as they turn the shower knob. The shower gurgles noisily and spurts to life, an uneven spray hitting the tile and splashing beyond the shower door. He waits for the water to warm while he shaves in front of the mirror, leaving the slightest bit of stubble. He runs a palm across his cheeks and inspects his chin, looking for any missed spots. Not bad, he decides with one approving nod in the mirror.

When the steam begins to rise and cloud the bathroom, Dean hops in the shower and works quickly. The hot water goes a long way in waking him up and clearing his mind. It’s Friday which means he doesn’t have any classes to teach today, but Sam still has to go to school. Speaking of, Dean has a hot date with a particular school teacher. He squirts a dollop of shampoo into his hand and works it into his hair. This date is either the best idea or possibly the worst. Castiel is Sam’s teacher. Should things go awry, Dean doesn’t want Sam to be affected in any way.

But also, Dean hasn’t been laid since he-can’t-remember-when and a man has needs. Dean is under no illusion which head is calling the shots.

Besides, he justifies while scrubbing his body with soap, should things end poorly...aren’t they’re both mature adults? Castiel is a teacher and he takes himself very seriously. He’ll be able to keep his emotions outside of the classroom. Sam will be fine.

Dean rinses and shuts off the water. He grabs his towel and wraps it around his hips, making his way back to his room. The warmth from the shower unfortunately stays in the bathroom and Dean hurries to dress before his nipples have a chance to freeze. He pulls on an older pair of worn-in jeans and a plain t-shirt, then makes his way to Sam’s room. He knocks on the door and waits for a response. When he doesn’t get one, he turns the door handle and pads quietly to Sam’s bed.

“Sam, wake up. Time for school.”

The lump burrowed under the covers contracts into a smaller form. “‘s too cold,” it mumbles.

“If you don’t get up,” Dean warns, “I’m going to tickle you.”

Sam’s head pops out of his blanketed cocoon. “No, don’t,” he whines.

“Then come on.” Dean stands as Sam begrudgingly sits up and rubs at his eyes. “Ten minutes, kiddo. I’ll be in the kitchen.”


Castiel’s television flickers on to the 6 o’clock morning news. The glare of the old analog casts the room in a harsh blue light and the muted volume is still audible under a layer of static. The low buzz slowly rouses Castiel from sleep as he blinks bleary eyes at the grainy image. The old thing is reaching the last of its days, but Castiel can’t bring himself to throw it out. It’s Lucy’s favorite napping spot, second only to Castiel himself when he lays down to sleep.

He drags himself out of bed, disturbing aforementioned cat sleeping heavily on his arm. Lucy makes a disgruntled sound before immediately seizing Castiel’s warm spot and giving him his back, purring like a made off bandit.

A quick shower and shave later, Castiel re-enters his room just in time for the weather segment. He fishes for the remote and ups the volume as he dresses. It’s promising to be a blustery day if the tree branches tapping at his bedroom window are any indication. “Bundle up!” the weatherman suggests, “It’s flu season again.” Castiel works with children, he knows his odds, and grabs his scarf from the hook on his closet door.

Today is Friday which means two things: 1) he has one last day to wrap up his social studies lesson before the field trip next week, and 2) he needs to make copies of the permission slips in the office before class. Next week will hopefully bring more promising weather as he will be escorting fifteen toddlers to South Park, Lawrence’s first and oldest park. He’d make due with at least a little bit of sunshine.

And oh, he remembers with a pleasant start, it’s finally Friday. In addition to work-related items on his mental to-do list, there’s also the little matter of having a date with Professor Green Eyes and Freckles Winchester. Make that three things.

Castiel makes his way to the kitchen and prepares a bowl of instant oatmeal (the microwave being the one thing he can operate without injury) before Lucy finally makes an appearance demanding his breakfast.

Castiel dutifully opens a can of wet cat food onto a small platter, then places the proffered food onto the counter. Lucy hops up gracefully and begins to eat as the microwave announces the oatmeal. The two sit together in comfortable silence until Lucy abandons his plate, spotless and clean, and nudges at Castiel’s hand.

Castiel scratches him behind the ears. “There’s a good boy.”


By the time Sam rushes downstairs fully dressed, Dean’s serving his scrambled eggs on a plate. Sam climbs onto the chair and reaches for his fork.

"Dean! I need ketchup!" Sam announces. Dean fishes for the ketchup bottle in the fridge and places it on the kitchen island just beyond Sam's reach.

“What do we say?” Dean prompts

Sam’s face turns serious. “I love you.”

Son of a-- “The other one, Sam.”

“Oh. Pleeeeeease?” Dean slides the bottle across the island. “Thank you!”

Sam squirts an overly generous amount of ketchup onto his eggs and digs in with gusto. Dean sidles in next to Sam, his plate heavy with two eggs overeasy and a liberal side of bacon, and places a napkin on Sam’s lap.

“Don’t wipe your hands on your pants.”

The two brothers eat in silence for about two seconds before Sam strikes up a new conversation.

“Are you and Mister Milton going to be friends? Because he asked you to play with him today and he’s really nice and I like him and,” Sam takes a long gulp from his glass of milk, “you need friends.”

Dean frowns, mock offended. “Hey! I have tons of friends. I’ve got you, don’t I?”

Sam nods furiously. “We’re friends!” He eats another forkful of eggs. “You’re gonna have a playdate, can I have one, too? I wanna go to Ruby’s house. She said she has three dogs and they win prizes ‘cause they’re pretty.” Sam sips at his milk and tries to sound nonchalant. “Can we have a dog?”

Dean really has to hand it to Sam, the boy gets an A+ for persistence and effort. “Nice try, Sammy. We’ve talked about this before and the answer is still no.”

“We never talk about it. I ask and you always say no.” Sam pouts and stabs mulishly at his eggs, kicking his dangling legs against the paneling of the island.

“Sam,” Dean sighs. It hasn’t even been a full seven days since the last Dog Discussion.

“And I still want lasagna!” Sam continues, uninterrupted. “You said we would get some and then I waited and waited--”

Dean takes a bite of his bacon, savoring the crunch. After four years of raising Sam, Dean can distinguish a routine tantrum from a real one. A real tantrum usually involves a lot of crying, some biting, and on one rare occasion, a painful headbutt.

“--and I want more milk. Can I have a piece of toast?”

“Sure, you can have some toast, but you gotta eat it in the car. It’s time to get you to school.”

Sam forgets all about the milk and the toast and climbs down his chair to run into the hallway to collect his backpack and hoodie. He’s an excited bundle of energy and Dean manages to wrap a scarf around his neck and tug on the front to cover his mouth and nose. Dean then throws on his coat, grabs his car keys, and steers Sam out the door.


Castiel lets in a cold draft as he enters the main office, a few sheets fluttering off Missouri’s desk as the door closes behind him. His coat collar is turned up in an effort to stave off the chilly air, his scarf pulled up past his nose, and his hair wind-tossed like a boat at sea.

The corners of his eyes crinkle as he smiles under the scarf. “Good morning, Missouri,” he greets, voice muffled by the thick alpaca knit.

“It’s not normally this cold mid-September,” Missouri comments by way of greeting. She bends to retrieve the fallen papers when she suddenly stills, her sixth sense tingling. Her eyes carefully scan the room coming upon the large glass window facing the school yard. Outside, she can see the tree leaves shaking, the heavy boughs bowing in the wind. Peculiar that this should catch her attention.

She continues to inspect the room. Something is here. Something big. Her sharp, intelligent gaze turns curious as her eyes land on Castiel, who has ambled toward the copy machine and begun to pull out a document from his bag. Every sense in her body stands on end. Oh.

Missouri stands and makes her way toward Castiel. She places a gentle hand on his shoulder. “Can I get you a coffee, hon?” she offers.

Castiel loads the feeder tray and presses the large green button. The copy machine whirrs to life.

“I can get it myself,” he politely declines. He draws away from the machine to tug off his scarf and remove his coat. When he turns back, Missouri is already holding out a fresh mug of coffee. Despite his quiet, reserved demeanor, Castiel likes his coffee extra sweet and extra light with three creams and three sugars. He accepts the drink with a small nod of his head.

“Thank you, Missouri, although I am more than capable of preparing my own coffee.”

“You hush and drink up. Let ol’ Miss Moseley momma you.”

Castiel smiles around the rim of the mug and turns back to the copy machine. An insistent red light illuminates the display screen: PAPER JAM. He sets his coffee aside with a troubled expression and investigates the machine, trying to find the source of the problem.

Missouri takes the opportunity to study him. He’s wearing a typical outfit, crisp slacks, a button down shirt, tucked in of course, a plain thin leather belt, and a charcoal wool cardigan. But there is something different about and around him, an air of excitement, an undeniable electric buzz. What is she missing, she wonders, desperately trying to understand. The wind bringing in the turn of the leaves, that same wind came in with Castiel when he stepped into the office. The wind of change, her mind whispers.

It is in that moment that she knows, with a deep sense of knowing, that she knows.

What finally tipped off her empathic abilities, she can’t say. If she had to parse it, if she had to whittle the moment down past the meat and straight to the bone she would say that she simply looked. She looked at the man in front of her, all twenty-nine years of him, and saw the boy within waiting to love and be loved.

It won’t be long now, Missouri muses.

She shouldn’t meddle. She should not meddle.

“Honey,” she meddles, and waits as Castiel turns to look at her, his hand still tugging at the jammed paper, “is that what you’re wearing tonight?”

Castiel startles and looks down at his outfit. He runs his hand down the front of his shirt, a subconscious nervous tick, and asks, “Is this not appropriate? It’s about the normal variance for what I usually wear to work.”

“No,” she clarifies patiently, “is that what you’re wearing tonight?”

Castiel, bless his heart, doesn’t stop to wonder how she could possibly know about tonight, for which she is thankful. Instead he looks down again and licks his chapped lips. “Is this not appropriate?” he asks, increasingly self-conscious.

Missouri purses her lips thoughtfully. “Do you own any jeans?”

“I have a pair my sister coerced me into purchasing,” he reports.

Missouri hands him back his coffee mug and pats his cheek fondly. “Wear those.”


Castiel ends his Social Studies lesson with an interactive project. Kevin distributes pre-cut white drawing paper and 8-packs of crayons while Castiel explains their task.

“In preparation for our field trip next week, I want you all to draw a picture of where you live. Do you live in a house? Do you live in an apartment? Do you have any pets? What about your home is important to you?”

Soon the sound of oversized crayons rubbing against thick paper joins cheerful chatter as the students work diligently on their new task. Kevin helps peel the paper away from the crayons’ whittled ends while Castiel sits with each child individually to talk about their ‘home.’

He approaches Ruby first, her long brown hair tied into a high ponytail. Castiel squats next to her desk so that they’re at eye level before pointing to three black dogs in her drawing.

“Are these your dogs?” Castiel asks.

“That’s Pepper and that’s Max and they’re famous. Coco’s still a puppy and needs training,” Ruby rattles off, “she ate my mom’s favorite shoes. They were Prada.”

Castiel hums, both amused and impressed by Ruby’s show dogs. He praises her attention to detail before moving on. He slowly makes his way around the room, stopping at each desk to discuss every student’s interpretation of ‘home.’ He learns that Ben Braden spends most of his time in his mother’s yoga studio, Adam Milligan has a baseball cap his father gave to him for his birthday, and Amy Pond’s bedroom is littered with stuffed animal foxes.

Sam is hunched over his desk, scribbling furiously. His drawings tend toward the elaborate and gruesome, so when he spots the black crayon snug in Sam’s hand, Castiel expects the worst. To his surprise, however, Sam’s interpretation of ‘home’ is remarkably tame.

“Hello, Sam,” he greets. “Want to tell me a little bit about your drawing?”

“This is my house. That’s my room,” Sam says, pointing to a large window flanked by arrows. “And that’s me and Dean.” Sam beams at his two smiling stick people. “And that’s the car! Dean says it used to be dad’s but now it’s his. Dean calls it Baby and he takes real good care of her. Once he made me a turkey sandwich and I got really mad and I hid it under the seat and then the ants found it and I got into a lot of trouble.”

Castiel bites back a laugh. Sam can be a handful in the classroom, he can’t even begin to imagine what he must be like at home. His gaze strays to a pathetic looking dog on Sam’s paper, complete with tears. “Do you have a dog, Sam?”

“Dean says I can’t have one,” Sam whines, “that’s why the dog is crying.” Sam pets the picture fondly. “But that’s okay, it’s just me and Dean and Dean is the best. He doesn’t tell anyone, but he’s a really good cook and he can bake! He makes me pumpkin pie even though apple is his favorite. Once you’re friends, I bet he’ll bake you anything. You should ask for pumpkin pie because that’s my favorite.”

Castiel smiles fondly at Sam. “It’s a very nice picture.” Sam blinks up at him. “Do you mind if I put it up on the Art of the Week wall?”

Sam’s jaw drops in disbelief. “Really?”

“Yes. Can you sign your name at the corner?”

Sam picks up the black crayon again and scrawls ‘SAM’ next to the big sad dog. He hands his finished drawing to Castiel with an enormous grin.

Castiel’s heart swells with pride at Sam’s barely-contained glee. If meetings with Dean Winchester mean more of Sam’s beaming face, then Castiel needs to schedule more parent-teacher conferences.


“--awesome. Thanks, Becky, you’re a lifesaver.” Dean pockets his cell phone and hums cheerfully as he picks up the laundry basket full of Sam’s clean and folded clothes. He skips every other step going up the stairs, striding down the hall into Sam’s room. He works at a quick place, needing to get done several chores before his dinner plans.

His bare feet pad softly across the room. He’s a few feet away from Sam’s dresser when he steps on something small, plastic, and unforgiving. Sharp, stabbing pain rockets through his foot and he yells out, doubling over in agony.

Dean lifts his foot gingerly and peels a small, green lego away from his skin, four small circles imprinted into his arch.

“Son of a--” Dean hisses, letting the lego fall back to the floor with a clatter. He sets down the laundry basket on top of the dresser and quickly puts away Sam’s clean laundry in its respective drawers before heading downstairs to fetch the broom.

Returning to Sam’s room, Dean begins sweeping, starting at the corners furthest from the door. When he sticks the broom under Sam’s bed, he’s not surprised to hear the clacking together of small plastic pieces. He pulls the broom toward him and a small cache of legos emerges from under the bristles. When Dean told Sam to put his legos away before going to bed, this is not what he had meant.

Still, Dean is in too high spirits to feel upset over Sam’s deviousness. Instead he picks up the mess quickly, dumping the pieces in their corresponding container, and heads outside to work on the Impala.

He decides to give his baby a quick wash. She’s not dirty by any means, but he wants everything in tip top shape for tonight. Tip top includes a quick wash, a new car freshener, and most importantly, a clean and unobstructed back seat. He even polishes the leather upholstery and vacuums the floorboards.

Dean hangs the used rag over his shoulder and gives the Impala a slow once over. He whistles appreciatively and pats the hood. “Oh, baby. We are back in business.”

Polishing his baby takes longer than anticipated and when Dean checks his watch, he’s five minutes late in picking Sam up from school. He pats his pocket, feels the bulge of his wallet and keys, and hops into the driver’s seat. The Impala pulls out of the driveway with a low purr.


“Mister Milton gave us a paper you need to sign,” Sam pipes up from the backseat. “We’re going on a field trip to the park. The one we like to go to!”

Dean glances at him through the rearview mirror. “Give it to me when we get home, I’ll sign it for you.”

Sam fiddles with the tassels of his scarf and peers around the back seat. None of his toys are in the car, and it smells different. Sam breathes in deeply through his nose. “Dean, the car smells like Christmas.”

“It smells like pine,” he corrects.


“What do you mean why? Because that’s the scent I bought for the car.”


“Because it smells clean.”

“It smells like Christmas.” Sam corrects before turning his gaze to the window and humming quietly under his breath. “Is Jo coming over to play while you’re playing with Mister Milton?”

“Jo has a lot of homework to do tonight, so she can’t watch you today.”

“Is Uncle Bobby coming?”

“No, he’s not,” Dean braces himself, “but Beckster offered to take care of you tonight.”

“No,” Sam immediately wails, “Dean!”

“Becky’s a nice girl and she--”

“No, no, no, no, no,” Sam shakes his head emphatically. Tears instantly pool and streak down his cheeks.


Sam takes a breath and wails loudly, shrieking and kicking his legs against his booster seat.

Dean rubs a hand over his face and focuses on getting home as quickly as possible. Sam, meanwhile, works his hardest to sway Dean’s stance on the matter.

“De-e-a-a-an,” Sam sobs pathetically, “don’t make me stay with B-Becky.” He hiccups and continues to whimper.

“Sam, it’s just one night. I made sure to remind her you don’t eat meat.”

Sam’s wailing renews in earnest as he remembers the traumatic event. “She tried to make me eat Betsy!”

“And she’s not gonna do it again,” Dean tries to console from the driver’s seat. “Buddy, it’s just one night, okay?” Sam’s whimpering continues, but he doesn’t reply. “Buddy?”

Dean peeks a glance at Sam through the rearview mirror. Sam’s arms are crossed over his chest, head resolutely turned toward the window. His silent treatment doesn’t render its usual effect -- it’s ruined by the melodramatic sniffling and the fact that Dean knows he’s just being a little shit. His snotty face is scrunched into an expression Sam believes to be menacing, but it’s difficult to be intimidated by a 4-year old.

Dean pulls the Impala into the driveway, killing the engine. He unbuckles himself and goes to unbuckle Sam who deliberately faces away from Dean as he undoes the clasps of his booster seat. Once free, Sam pushes past Dean up the front steps of the house, foot tapping impatiently as he waits for Dean to open the door.

The front door swings open with a click and Sam runs up the stairs to his room.

“No running!” Dean yells after him. Sam slams his door in response.

Dean dumps Sam’s jacket, scarf, and backpack onto the couch and heads to the kitchen. Sam’s tantrum began typically (tears, yelling, kicking, silent treatment), but door-slamming isn’t in his repertoire. Dean frowns, opening the refrigerator and pulling out fresh celery stalks. This is different.

Closing the lid of the peanut butter jar, Dean leans against the kitchen island and stares at Sam’s after school snack. The raisins nestled in the peanut butter stare back.

Dean sighs, grabs the plate, and heads up the stairs. He knocks at Sam’s door. Silence.

“Sam, I’m coming in.”

Dean opens the door and finds Sam huddled under his blankets. The lump curls up tighter and gives its back to Dean.

“I know you’re not talking to me right now, but I made you a snack.” He sets the plate on the bedside table and notices that the little lump under the covers is shaking.

Sam’s crying for real.

“Hey now,” Dean says gently, pulling the covers back. Sam looks up at Dean and launches himself at Dean’s front, little hands grasping his shirt and his wet face pressing in at the crook of his neck. His shirt slowly grows damp, but Dean doesn’t mind as he slowly pets Sam’s back.

“What’s wrong, Sammy?” Sam shakes his head and sniffles. “Is this about the Beckster?”

Sam whimpers and nods, clinging harder to Dean’s shirt. “She’s a trickster,” he mumbles into Dean’s neck.

“A trickster?” Castiel’s warning about reading inappropriate stories for Sam’s age group comes to mind, and he suppresses the urge to roll his eyes. He can imagine him clearly, the smug expression, arms folded in a cocky manner, the I-told-you-so without ever saying, ‘I told you so.’ Dammit.

“Sammy, tricksters don’t exist. They’re just pretend.”

Sam takes in a shuddering breath. “Then w-why do you call her Beckster?” he asks, voice thick with accusation.

“Beckster’s just a nick---” Sam jerks in his arms. “Okay, okay. Um,” he fumbles, trying to problem solve his way out of this mess. If Sam thinks tricksters are real, Dean telling him otherwise is not going to change his mind. A solution slowly takes shape. It’s a little unconventional, but you don’t befriend the crazies by challenging their delusions. In fact, you do the opposite.

“What do tricksters like to eat the most?”

Sam is silent, then murmurs, “Sweet stuff. Like candy and cake.”

“That’s true,” Dean nods, encouragingly. “They’re really into sugar. Have you ever seen Becky eat a piece of candy?”

Sam ponders for a moment. “No...” he admits.

“And what does she tell you when you brush your teeth?”

Sam turns watery eyes up at Dean. “That sugar is bad for your teeth.”

“That’s right,” Dean says, brushing a thumb under Sam’s eyes. “She wears braces, too. Do you think she would wear braces to fix her teeth, then ruin them by eating candy?” Sam shakes his head. “It just wouldn’t make sense, right?”


Dean shifts Sam in his arms so he’s sitting in Dean’s lap. “So what did we learn?”

Sam sniffs once, nose still runny. “Becky can’t be a trickster.”

“Ding ding ding! Give the winner a prize!” Dean reaches over to the bedside table and hands Sam his snack. Sam rubs at his eyes with his sleeves and offers Dean a shaky smile.

Dean pinches his cheek. “Besides, even if she were a trickster, she’d never want to hurt you because you’re just so darn cute.”

Sam brings up a hand and touches Dean’s cheek. “You’d never let her hurt me.”

Dean swallows around the sudden lump in his throat. “That’s right.” He steals a celery stick off Sam’s plate and takes a bite. “Come on. I made enough for both of us. Eat up, kiddo.”


It’s twenty minutes until 6 o’clock and five minutes until Dean has to leave to go pick up Castiel at his apartment. Dean checks his appearance in the full-length mirror hung on his bedroom door. He’s wearing one of his nicer pairs of jeans, an ironed plaid button-up, and his boots are buffed and shined. He shoots himself a sly grin. Yeah, he’d sleep with himself, too. Which reminds him.

Dean walks over to his bedside table and opens the first drawer. He pulls out a box of condoms from the back and checks the expiration date. Still good. He tears off two packets from the roll and tucks them into his wallet. Then he tears off two more because you never know. He’s got a lucky feeling about tonight.

Sam’s Sesame Street DVD blares from the living room as Dean heads to the bathroom to brush his teeth. Grover’s warbly voice accompanies his final touch-up, and Dean pats on his cologne in time with the muppet monster’s song.

Dean trots down the stairs into the living room, picks up the remote and lowers the volume.

“Hey!” Sam protests.

Dean sets the remote just out of Sam’s reach. “I could hear the TV all the way upstairs.” Sam pouts and Dean narrows his eyes. “And why are you watching TV, anyway? Did you finish your homework?”

The doorbell rings before the interrogation can continue. Dean points meaningfully at Sam as if to say this conversation isn’t over. Sam ignores the message and points to the door. “Someone’s at the door.”

Someone is indeed at the door, and her teeth chatter as she enters the house. “Heya, Professor Winchester. I hope I’m not late.”

“No, you’re right on time, Becky.” He helps her out of her ridiculous pink coat and hangs it in the coat closet. They move into the kitchen as Dean gives a quick rundown on the rules. “I went ahead and made dinner, it’s in the oven. I hope you like lasagna, but you can help yourself to anything you find in the fridge.” He leads them back down the hall and pokes his head into the living room where Sam is struggling with his container of hot wheels. He frowns at Sam, who looks up guiltily at Dean. “Make sure Sam finishes his homework. No TV or any toys whatsoever until he’s done, that’s final.” Dean starts making his way to the front door, wrapping up his little speech. “He should be in bed by 8 and I should be back by 11.” He heads to the coat closet, pulls out his leather jacket, and shrugs it on.

“And you know you can call me in the case of an emergency, but if it’s serious then call 9-1-1 before you call me--”

“I know the drill, Professor,” she laughs, waving her hand as if to soothe his concerns. His totally legitimate concerns. “No worries! We’ll be fine.”

Dean pauses at the threshold of the front door. “I know he can be a handful at times.”

Becky flashes a toothy smile, braces and all. “Oh, Sam’s just a sweetheart. I could eat him right up.”

Something crashes in the living room and Sam shoots into the hall, frantically attaching himself to Dean’s leg and tugging.

“Do you really have to go? Please, please don’t go! Play with me instead! I don’t want you to go. Dean, please?” Sam’s grip tightens on Dean’s pant leg. Dean’s belt starts to dig into his side.

“Sam we talked about this--”

Sam turns to Becky abruptly. “Do you like lollipops?”

“Well, not particularly--”



Castiel stands in front of his full sized mirror, a feeling akin to dread coiling tight around his chest. He has a date with Dean Winchester in less than an hour and now thanks to Missouri, he has no idea what he’s going to wear.

Oh dear Father above. Dean Winchester. His student’s guardian. What is he thinking?

He isn’t. Asking out Dean Winchester had been a spur of the moment decision. He’d been taken by Dean’s devilishly good looks, his soft green eyes as they peered at Sam, and his firm muscles as they effortlessly picked his younger brother up off the ground. He hadn’t even given it a second thought -- something about the man made him act impetuously. Very dangerous.

He had planned to wear his work outfit to dinner. It was sensible; he knows he looks clean and neat because he buys his outfits right off the mannequins that parade them. He knows he is “color-coordinated” and “in-style,” and yet Missouri had insisted on jeans.

He digs through his closet, looking for the pair of jeans he purchased last year after Anna’s insistent cajoling. He finds them in the very back of the closet, pushed aside by slacks and steam-pressed collared shirts. He slips them on and is ashamed to admit he has to wriggle his way into them.

“You have to buy them a size too small, Cas,” Anna had informed him. “Denim stretches, but you still want to show off that ass.”

Said ass is currently trying to breathe, but he dutifully struggles with the button and pulls up the zipper with a huff of victory. They fit a little snug, but then again, that is the point. They’re a dark wash (“Serious jeans because you’re the boring type,” Anna had teased lovingly) and Castiel is pleased to note they are the right length.

He ends up pairing his jeans with a light blue button up, tucked in at the waist and buttoned all the way up to the top. It looks like a combination Anna would approve of for a date. He briefly considers just calling and asking her, but that would also involve admitting to having a date in the first place and he knows she would tell Gabriel and just no. No, no, no.

He grabs a thin brown leather belt and fishes it through the belt loops. He stares at himself critically in the mirror and assess the outfit he’s put together. He unbuttons the top two buttons of his shirt experimentally. There. Now he’s sophisticated and casual. Casually sophisticated.

“Fashion is very confusing,” he admits to Lucy, who watches him lazily from the top of the television.


Dean drums his fingers on the steering wheel as Hot Blooded pounds through the speakers. He is loathe to admit that it’s been a while since he’s gotten laid. The fact that he needs music to help pump him up for tonight’s date is almost embarrassing. Still, the music seeps into his body like an energy shot. Minutes before he pulls up to Castiel’s apartment, he’s ready to lay on the Winchester Charm.

Traffic is lighter than expected and Dean arrives at the apartment six minutes early. He takes a moment to drink in his surroundings. While Dean lives in a quiet little corner a few minutes drive from the university, Castiel lives in a busier part of town, two- and three-story apartment complexes making up most of the area. Despite it being a bustling place, the neighborhood is tidy and well-kept, with trees lining the road. Dean checks his phone to confirm the address, still four minutes early. The radio starts to play Blue Öyster Cult and Dean waits to call Castiel to tell him he’s here. He doesn’t want to seem too eager. He’ll call right on time, show he’s punctual, interested. Yeah.

The song starts to fade as the radio host cuts in, and Dean leans over to shut off the radio. He presses ‘Dial’ on his phone and stares at the building’s façade. Castiel picks up after two rings.

“Hello?” Castiel rumbles sexily.

“Castiel? It’s Dean Winchester.” Dean feels his face flush. What?

“Oh, yes, hello. How are you?”

“I’m fine.” Dean clears his throat. “Actually, I’m outside your apartment.”

“Oh.” Dean thinks he imagines the panicked quality to Castiel’s tone. “I’ll be out in a minute or two. Is that alright?”

“Sure, take your time.”


Lucy’s tail flicks excitedly as Castiel paces through the apartment. He spent so long fixating on his outfit that he completely forgot to schedule in time for his hair. He struggles into a pullover, pulls on his trench coat, and wraps a scarf around his neck. He makes to the door and stops right before putting his hand on the knob. It will just take a second, he reasons as he heads back to his bedroom one final time, tugging his brush through his hair in a last ditch effort to look presentable.

Castiel is simultaneously graced and cursed with a head of thick, healthy and unruly dark brown hair. He puts his brush down and looks into his mirror. His hair sticks up in stubborn, uneven tufts. He looks like he just rolled out of bed. Dean is going to think I didn’t try at all, he rues.

Lucy reaches up to play with the end of his scarf, but Castiel pulls away before a claw can snag on a thread. He hurries back to the front door, grabs his keys off the hook by the door and pockets his wallet.

“I’m off, Lucy. Don’t make a mess.” Lucy pulls into a stretch and curls into a ball on the couch, watching the door with one lazy eye.


When Castiel finally exits his apartment complex, he is greeted by Dean seated on the hood of a sleek, black car. He’s seated comfortably, leaning back lazily and balancing his weight on his hands. The second Dean spots him, he jumps off and lands solidly on his feet.

Oh, Castiel thinks. “I hope you didn’t wait long,” he says.

“Uh, no, no. Not at all.” Dean licks his lips, mouth suddenly dry. Castiel looks really good. He didn’t seem like the jean-wearing kind of guy, but damn. He needs to stop wearing slacks and slip into a pair of Levis more often. Even the trenchcoat can’t hide those muscular thighs and Dean is struck by an overwhelming desire to bite them. Knockin’ me out with those American thighs, his mind helpfully offers as the soundtrack to Dean’s fantasies. Thank you, AC/DC.

Dean snaps to and hastily opens the car door for Castiel, who nods in thanks and brushes close as he slides into the car.

“Nice car,” he murmurs and Dean has to fight back a smug grin.

He shuts the door behind him and struggles to regain his composure before getting in behind the wheel. Come on, Winchester. Pull yourself together.


The car ride to the restaurant turns awkward very quickly. Castiel sits perfectly still, back ramrod straight with his hands on his lap. Silence pervades the space, the only sounds coming from the heater, set to medium-high and slowly fogging up the side windows. Now would be the perfect opportunity to charm the pants off Cas, but Dean finds himself unable to think of anything suave to say.

“So...” Dean begins instead, lamely. “The Roadhouse’s okay with you?”

Castiel nods, a short, curt movement. “Yes. Their burgers are quite good.”

“Okay, cool. Just checking,” Dean winces. What the hell is wrong with him? Now is not the time to act like a thirteen year old virgin with a crush. “Do you go there often?” Seriously??

“Now and again,” Castiel responds distractedly, fingers fidgeting with the lapels of his coat.

“You can take that off, you know. You’re pretty hot,” Dean’s jaw snaps shut at the Freudian slip. “Uh, I mean, you look a little hot. I mean, you are a little hot, I mean you’re more than a little hot, you’re like a lot,” Dean’s voice dies down in embarrassment, “hot.”

Castiel begins to laugh; it’s not a mocking sound, but an incredibly amused one. The slope of his shoulders relaxes into a more natural posture and he turns to look at Dean who is resolutely staring at the road ahead.

“Yeah alright, laugh it up, Chuckles.” Dean grunts, but there’s a hint of a smile. “How about I try again,” Dean proposes. “How was your week?”

Castiel looks surprised by the question. “My week? It’s been pleasant, but it’s also not quite over.” He turns to Dean and smiles, teasing. “I’ll have to make a reassessment at the end of the night.”

“I hope you curb your grading,” Dean jokes.

“Are you implying I’ll need to?”

“Hell no.”


As expected, The Roadhouse is decently packed for a Friday night. Dean and Castiel shake off the cold as the hostess makes her way to the front.

“Hi, I’m Jo and I’ll-- oh, it’s just you,” she directs to Dean.

“Nice to see you, too,” Dean deadpans.

Jo opens her mouth, a playful retort on the tip of her tongue, when she spots Castiel standing behind Dean. It takes her less than a second to put one and one together and get GAY DATE. Dean can see the cogs turning in Jo’s head and knows the whole extended family will hear about tonight before dessert.

“Do you think we could get a booth somewhere a little quiet?” Castiel requests, looking around the busy restaurant.

Jo has the decency to at least pretend to be professional as she turns on her heel and leads them to the most private booth near the bar.

“Anything to start with, boys?”

“Beer from the tap for me, thanks.” Dean opens his menu to the entree page.

Castiel peers at the drink selection. “I’ll have a beer as well. Your imported draft, please.”

“Sure thing.”

Dean follows Jo as she approaches Ellen at the bar. They drop into conspiratorial whispers while shooting their table not-so-discreet glances. Typical. Movement in his peripheral vision catches his attention. Castiel is shrugging out of his trenchcoat and struggling out of his pullover. Dean’s brain promptly shuts down. Castiel isn’t built, but he’s toned and lithe. He has a runner’s body, slim hips, and strong thighs he wants to see straddle his lap.


“Wh- huh?”

“I asked, ‘Should I be jealous?’” He tilts his head in the direction of the bar.

“I hope you’re joking,” he deadpans. “Jo’s like a sister to me.”

“Just making sure,” Castiel murmurs, then busies himself with perusing the menu.

Dean is suddenly very warm and he slips off his own jacket, draping it over the back of his seat and rolling his sleeves up to his elbows. Castiel’s eyes slide off the pastas and straight to Dean’s biceps, still discernable under the sleeves. He’s usually not one to blaspheme, but Lord Almighty. It’s quickly becoming apparent that Dean Winchester is a deliciously generous package. Gorgeous man, gorgeous car, just plain gorgeous. He doesn’t realize he’s staring until Dean shifts under the intense scrutiny.

“You gotta try the burgers, they’re top notch.”

Castiel berates himself for getting caught staring. “I was planning on ordering one, but I always try to see if something else catches my eye. It seems my stomach is quite set on a burger, though.” He smiles over his menu and Dean’s stomach does a little flip.

Jo returns with their beers, setting them down with a thunk. Castiel wipes the foam spilling over the lip of his glass with a finger and brings it to his mouth to suck clean. Dean stares unabashedly.

Jo clears her throat. “You guys ready to order?”

“I believe so,” Castiel replies. “I’ll have the Classic Roadhouse Burger, medium rare, hold the pickles.”

“Okay. The usual for you, Dean?”

“The Hogtied Cheeseburger, extra bacon. Medium rare.”

Jo rolls her eyes. “You eat so much bacon you’re practically a pig.”

Dean levels her a glare.

“Alright, alright, I’ll go get your food.” She walks away, but manages to catch Dean say, “Ignore her, Cas...”

Aha. So his name is Cas? Time to tell mom.


“--so the guy has no idea what I’m talking about and miraculously pulls the answer out of his ass. If he weren’t so ballsy I’d have failed him on the spot.”

“I’ve never had to fail anyone,” Castiel muses.

“Dude, are you serious?” Dean exclaims, momentarily forgetting Castiel teaches children.

“Can you imagine failing a four year old? For what, unsatisfactory fingerpainting?” Castiel puts down his half-eaten burger and picks up a fry. “In a way I’m glad. Everyone does their best and everyone passes.”

Dean steals a fry off Cas’s plate, long since running out of his own. “I could not teach children. I don’t know how you do it, Cas.”

The repeated nickname brings a smile to Castiel’s face. “I do what makes me happy. For example,” he says, holding up his burger, “these burgers make me very happy. So I shall eat them.” He takes a bite as if to prove his point, closing his eyes as he chews thoughtfully.

Dean’s heart suddenly races. Dear god, this man is perfect. If he loves pie, Dean’s set for life.

They finish their respective burgers in comfortable silence until Jo comes by to clear the table. She throws her dish rag casually over one shoulder and whips her order pad out of her waist apron.

She flashes a pretty grin at Castiel, flipping the order pad open. “Would you like some dessert, sugar?”

“No, thank you,” he returns politely at the same moment that Dean says, “You know the answer’s yes, Jo.”

Jo rolls her eyes and snorts. “The answer’s always yes with you, porky.”

Dean wraps a protective arm around his stomach. “That’s no way to treat a paying customer, Joanna Beth.”

“Would you like to file a complaint with management?” Jo turns to the bar and shouts. “Hey, Ma!”

“Just get us some hot apple pie, a la mode, please. And get out of here before your mother comes over.”

Jo smiles prettily, feeling victorious. Dean’s a pushover when he’s on a date with a cute boy. She’ll remember this when she needs to force his hand in her favor. “I’ll bring two spoons.”

“I’m assuming her mother runs this establishment?”

Dean takes a drink from his beer. “Yeah, they’re good people. They helped me take care of Sam while I was still in school. Well, not just them, but still.”

“That must have been difficult.”

“Yeah, well.” Dean fiddles with his napkin. “Oh hey, check this out.” He folds the napkin methodically on his lap, hiding it from view until it’s complete. “Tah-dah. It works better with cloth napkins. More flexible.”

“It’s a crude approximation, but I suppose it’s rather well done for a paper napkin.”

“Don’t knock on my penis napkin.”

“As long as I can knock on something else,” Castiel delivers, straight-faced.

Dean chokes on his beer.

“Ugh, get a room. Here’s your pie.” Jo unceremoniously dumps the pie onto the table, droplets of ice cream splattering onto the wood.

“Oh baby, come to papa.” Dean slides the plate between them, offering Cas his spoon and taking up his own. “This is the only way to have apple pie, Cas. Trust me. Straight outta the oven with some old-fashioned vanilla ice cream on top.”

“I’m not really one for pie,” Cas admits.

“Just try it. I’ll convert you yet.” Dean takes a generous bite of pie and ice cream and sheds any sense of decency as he moans around the spoon. “Oh, that is so good.”

Cas’s bite is conservative in comparison, but the burst of sweet hot and cold on his tongue draws an unbidden sound of surprise. “It is good,” Cas agrees, and takes another bite.

“Like manna from heaven, am I right, angel?”

Cas’s spoon stops right before his mouth. “You looked up my name, didn’t you?”

“I know a thing or two about angels. It kind of falls right into supernatural lore. So I’m guessing you were born on a Thursday?”

“If I didn’t know any better, I’d say you are trying to impress me.”

“Is it working?”

“Very much, yes.”

Between the two of them, the pie slowly disappears and the ice cream pools at the bottom of the plate where the spoons can’t reach. Dean is the first to give up on his spoon, swiping his index finger across the middle of the plate to collect a dab of melted ice cream. He brings the finger to his mouth, tongue licking the finger clean in one broad swipe. Castiel follows the movement with a half-lidded gaze.

Everything about Dean seems to demand his full attention. From his youthful and boyish personality to the confident ease of his sexuality, Dean is a maddeningly attractive mix of sex and innocence, intelligence and base humor. Having Dean’s undivided attention is intoxicating, and it’s a feeling Castiel will hate to relinquish. It’s possible, Castiel realizes with a jolt, that he may already be quite taken with a man he’s only just met. The thought startles him, but when Dean offers him ice cream from the tip of his finger, the ice cream is not the only thing that melts.


Dean and Castiel stay until closing time, only realizing the hour when the background din of hungry patrons fades into the distant sound of Jo pulling stools away from the bar to make way for the broom.

Both Dean and Castiel fumble for their wallets before Ellen meets them at their table.

“We’re closed and I ain’t counting the till twice. Just go on home, you two.”

Castiel begins to protest. “I couldn’t possibly--”

“I’m buying your customer loyalty with a meal. Think of it as a courtesy with ulterior motives. Now get.” Castiel slowly shrugs into his pullover, knowing a losing battle when he sees one. “Dean, don’t forget to bring Sam around sometime. The boy’s too thin. At this rate he’ll be stuck in that booster chair til kingdom come. What he needs is a real Harvelle feast to fatten him up. And Cas,” she tests the name on her tongue, deciding she likes it, “sweetie, I hope to see more of you.”

Dean tips an imaginary hat. “Thanks for the meal, Ellen.”

The two take their leave and walk briskly through the parking lot, making a beeline to the Impala and the promise of a heater. Dean goes to unlock Cas’s door first like a true gentleman and gets as far as shoving the key in the lock before he suddenly finds himself shoved back against the Impala, Castiel pressing in close and kissing the lights out of him.

The shock is only momentary, and he’s quick to get with the program, his hands finding Cas’s scarf and pulling him in closer as their lips lock. The cold completely forgotten, Dean focuses on Cas’s hot tongue sliding against his own, the thigh pressing in between his legs, and Cas’s insistent hands creeping around the hem of his shirt.

Dean would never admit to getting lost in the kiss, but he was definitely very focused. Why else would he fail to notice the car key digging into his back and Jo coming outside to throw out the trash?

“Oh my god,” Jo gasps, “get a room you guys. You’re worse than the cats in the alley.”

Dean jumps as Cas pulls away with a breathless laugh.

“Isn’t it past your curfew? Go back inside,” Dean snarks.

Jo flips him the bird and goes back inside promising, “I’m telling Ma what I saw!”

Cas steps close again and nuzzles his neck, nipping at his jaw. “I’m sorry. I’ve wanted to do that all night.”

“No, that’s uh.” Dean clears his throat. “That’s totally okay with me.” One kiss turns into two, turns into three. The kisses turn frantic before Dean remembers they’re still standing in a parking lot, freezing their balls off. And frozen balls are blue balls (in a way), which is the opposite of what he wants.

“What do you say we get out of here?” Cas nods and Dean opens the car door. Castiel slides into the car while Dean knocks off the fall foliage caught in the windshield wipers. He settles into the driver’s seat, turning the key in the ignition and the heater to its hottest setting. Dean turns to look at Cas.

“Is some music okay with you?”

“Of course,” Cas nods. Dean presses the power button before he shifts gears to pull out of the parking space.

“--s just after 10 o’clock, you folks are listening to Loooove Hour--”

Dean hastily shuts off the radio. “I don’t usually listen to that,” he laughs nervously.

Castiel does not comment on the radio station, focusing instead on the time. “Do you think you can drive quickly? I want to be able to kiss you again.”

Dean steps on it.


The second Dean pulls up to the curb and kills the engine, Cas is back in his personal space, manhandling him up against the driver’s door and carding a hand through his hair. Castiel is stronger than he lets on, and a spike of desire shoots straight to Dean’s crotch. The kisses are rough and Cas tugs on his hair painfully and this is what Dean loves about sleeping with men -- the power struggle, the physicality, the push and pull toward dominance. Dean’s not a bottom, but holy fuck. If Cas is this aggressive, maybe he wouldn’t mind giving it a shot.

Given Castiel’s profession working with kids, it is a complete turnaround to discover the dormant alpha within. Castiel takes complete control of their makeout session, slipping in tongue, nipping at his neck and jawline, suckling on his earlobe, and managing to pull small moans from Dean’s lips as if he were a fucking virgin.

The Impala creaks on its suspension when Castiel suddenly pulls away, smiling as Dean leans forward, trying to recapture his lips. Cas keeps him firmly pinned.

“What’s the matter?” Dean demands. He’s hot, he’s bothered, and he’s got a boner with Cas’s name all over it.

“It’s late. I believe you said we only had until eleven.”

Dean looks over at the dashboard. The clock blinks 11:08pm. Son of a bitch.

Castiel kisses the scowl off Dean’s face. “Call me, if you feel so inclined.” He slides out of the car and walks into his apartment building, punching in the security code before entering. Once he’s safely indoors and out of sight, Dean exhales slowly.

Did he really just spend three hours having dinner with someone, and then spend one hour just making out? Something is seriously wrong, here. Whatever happened to Hole-In-One Winchester?

He tries to feel upset at the way his night ended versus the way it could have ended, but his heart’s not in it. He enjoyed himself, more than he’s ever enjoyed himself on any date in the past. He’d be walking on air -- if he were walking. As it is, the Impala purrs to life beneath him and they coast home together.


When Dean gets back to the house, Sam opens the front door before he’s even on the porch. Dean gives Sam a disapproving look.

“Sam,” he starts, “what have I told you about opening the door by yourself?”

Sam’s bad mood is palpable. “But I knew it was you,” he scowls, “I heard the car.”

“That’s no excuse. Why aren’t you in bed?”

“Why are you late?”

Becky runs into the foyer, stopping behind Sam. “I’m so sorry! We were in the kitchen and I turned for a second to get a glass of water and then he was gone and I heard the front door open and--”

Dean tries to calm her, but once Becky gets on a roll, it’s easiest to let her get it all out. Dean picks Sam up, and he immediately nestles under Dean’s chin.

“--but it’s not like we live in New York or anything and it’s pretty safe around here and Sam was very well behaved like usual except he didn’t want to go to bed so I thought maybe he was still hungry because he only ate half his lasagna but he did eat his broccoli which doesn’t usually happen with kids so I guess you’re glad he eats his veggies-- Oh my.”

Dean sets Sam down and nudges him inside toward the stairs. Sam banks left and heads to the den. When he turns back at Becky, she’s trying and failing to look anywhere but at his neck. Dean rubs an absentminded hand over his collarbone and feels the beginnings of a bruise. That sneaky bastard.

Dean pulls his wallet out of his pocket. “How much do I owe you for staying past eleven?”

Becky starts. “What? Oh no, I couldn’t possibly take extra, Professor! Just the usual should suffice. We had a lot of fun playing today. He’s just the sweetest!” She turns to look where Sam disappeared into the den. “I’m sure he’ll grow up to be a real lady-killer.”

Dean helps her back into her coat and pushes an extra twenty into her palm anyway. “Thanks for taking care of Sam, Beckster.” Dean hears a tin container rattle as toy soldiers tumble onto the carpet. “Now if you’ll excuse me, I have to put a certain little monster to bed.”

Goodbyes and good nights are exchanged, and Dean shuts the front door with an exhausted sigh. He trudges to the den and finds Sam making battle plans with his soldiers.

“Now is not the time for playing. To bed with you.” Dean lifts Sam up from under his armpits and pulls him away from his toys as Sam protests, “But I’m not tired!”

“It’s way past your bedtime, of course you’re tired.” Dean shifts Sam under his arm, holding him like a football. “Did you brush your teeth?”

“Yes,” Sam punctuates with a yawn.

“Good,” he answers, before putting them both to bed.
Tags: pairing: castiel/dean, type: fic, word count: 5001-10000
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