Work Header

More Than Detention

Chapter Text

“Dean Winchester?” Dean lifts his head halfway, eyes remaining on the book he’s reading. It’s the only acknowledgement he gives the secretary that he heard her. “Mr. Novak will see you now.”


“Yeah, I bet he will,” Dean says with a smirk. He stands up and walks past her without another word, knowing the way to the new principal’s office extremely well. Before he enters the room, Dean slips his small paperback copy of Allen Ginsberg’s Howl into the back pocket of his jeans. It’s the only thing he changes. He leaves the half-smoked cigarette tucked behind his ear. He doesn't remove his leather jacket, or the flask of his dad's whiskey that's resting in one of the pockets. He definitely doesn't zip that jacket closed, even if his cotton white shirt is so thin you can see every tattoo beneath it. 


Dean doesn't knock, instead just pushing into the office. Mr. Novak isn't even surprised anymore at the behavior. He just stares blankly at Dean as the young man closes the door, locks it, and slumps down in a chair on the opposite side if Mr. Novak's desk. 


"Mr. Winchester," the principal finally states as a way of greeting.


Dean nods his head. "Novak."


"What is it this time? Smoking in the bathroom? Having sex in the janitor's closet? Sneaking-"


"Blowjob," Dean states simply, interrupting him.




"The incident you're referring to. From last week." Dean winks at him. "It was a blowjob in the janitor's closet. Not sex."


"Same thing, Winchester."


"Actually, Novak, it's not." Dean rests his elbows on his knees and leans forward, grinning. "Want me to show you?"


As always, Mr. Novak isn't flustered. He just continues to look at Dean with contempt. After a few more seconds of staring each other down, Mr. Novak sighs. 


"Do you care to explain why you've been sent to my office three times this week?"


"No problem, teach. Let's see," Dean tilts his chin and looks at the ceiling like he's thinking hard. "Well, first was the fire alarm issue. Second, if I remember correctly, was for telling Mr. Singer that he's a pompous ass who-"


"Language," Mr. Novak says in a tired, uncaring voice. 


Dean doesn't miss a beat. "Believes that no one can have an opinion on the material but him. As if he was there when Vonnegut fucking wrote-"




"Slaughterhouse Five. You think that prissy dick has ever-"




"Stepped foot in war? Or in any situation that left him traumatized? I sincerely fucking doubt-"




"It, Mr. Novak." Dean shrugs and sits back, not even winded from his angry rant. His body is used to them. "Three, however, is my favorite."


Mr. Novak arches an eyebrow. "Getting caught skinny dipping in the school pool in the middle of the school day is your favorite?"


Dean winks at him, smiling wide. "See, I knew you were aware of why I was here."


"Mr. Winchester, you -"


"Call me Dean."


"Excuse me?"


Dean leans forward again, darting his tongue out to wet his lips. "You'll be seein' a lot of me, handsome. Might as well call me Dean. It's shorter. Easier. Especially when screaming it during sex."


The only reaction this earns Dean is a slight tightening of Mr. Novak’s jaw. He takes in a calm breath before slowly telling Dean, "Twice last week. Three times this one, and it's only Wednesday. We're not even two weeks into school yet, Mr. Winchester. "


"Thanks for the stats, teach. I had forgotten."




"Why did I forget? Oh, well, that's probably a mixture of the beatings, the weed, and the-"


"Enough!" For the first time, Mr. Novak loses his cool. He slams his hand down on the center of his desk as he stands up to tower over Dean. Dean just smiles up at him like an invitation. "Tell me why you've been acting up like this, Dean. You were never well-behaved, but my records indicate that this is a new level."


Shrugging, Dean teases, "Maybe I'm enjoying detentions. That Mrs. Harvelle is quite the MILF."


Eyes narrowed, Mr. Novak speaks in an unsettling voice, “No, Mr. Winchester. I think you’re in need of more than detention.”


For the first time, Dean loses some of his confidence. "And - and what is that?"


"You're 18, correct?"


"Uh, yeah?"


"Good." Mr. Novak steps back from his desk. Staring Dean down, he undoes the buttons on his cuffs and rolls up the sleeves of his dress shirt. Then he's slowly removing his tie, sneering when he sees the way Dean watches his fingers manipulate the silk in a trance. "Stand up, Dean."


For the first time in perhaps ever, Dean is speechless. He doesn't even realize he's following the order and standing until he's being beckoned forward. Dean stares at his feet as they move around the desk, only pausing when they've stopped so Dean is only inches from Mr. Novak. 


Dean stares up at him in both fear and curiosity. "Since you can't ever keep your mouth shut, I thought I'd help you out."


Before Dean can ask what he means, the silk of Mr. Novak's tie is brushing against his cheek. The man steps into his space further as he reaches behind Dean's head. That's when Dean realizes what's happening. Mr. Novak is tying his tie around Dean's head, letting the material slip between Dean's parted lips. He whimpers when Mr. Novak harshly tugs at the material so it's digging into the corners of his mouth. His body begins to tremble as the knot is firmly tied at the back of his head. 


Rolling his tongue against the material, Dean's surprised at how full his mouth feels despite the tie being thin. He tries to speak but only manages a muffled, incoherent, "Wa's 'oo do'n M's N'v?


Using his common sense, Castiel figures Dean is asking something along the lines of 'What's going on?'  


Castiel answers, not because he has to, but because he's not a dick. Even if Dean Winchester pushes every single one of his fucking buttons, he's not a dick. “I’m going to punish you properly.”


Castiel turns him so he's facing the desk, then rests his lips against the shell of Dean's ear. He chuckles when the boy shudders and presses back against him. "I think you're in need of something much more hands on than detention, don't you think Mr. Winchester?"


Dean frantically nods, looking over his shoulder at Castiel with wide green eyes. 


"I think naughty boys like you need a lesson." He presses a hand to the middle of Dean's back, pushing until his front is resting against the desk. "I know why you keep getting sent here, Dean. I saw that look in your eyes the first time you saw me. You have a crush on the new principal."


Dean half-heartedly mumbles into his gag, shaking his head. This just makes Castiel laugh. "Don't lie. Liars are extra naughty. You don't want the extra naughty boy punishment now, do you?"


A slight whine escapes the boy as he quickly jerks his head in a firm no. "That's what I thought." 


Castiel can’t help but grin at the confirmation that this boy has a crush on him. It makes all his dirty thoughts regarding Dean the past two weeks much more valid. Just because he has a crush, though, doesn’t mean Dean wants it to be reality. Castiel knows if Dean starts to fight or begs to stop, this will be over in an instant. Gagged or not, he won't rape anyone. He is silently praying Dean wants this too. He has to make sure, though. Dean has to be able to say no. 


Castiel reaches over and picks up his small rubber band ball. He places it in Dean's right hand before softly stroking his arm to comfort him. "You drop that and this is over. I promise. If you get scared. If you don't want this. If I go too far. Drop that ball and everything stops, okay?"


Dean weakly nods. 


"Drop it for me, Dean. Show me what a good boy you can be."


The ball drops immediately, bouncing off Castiel's leg. 


"Mmmm, such a good boy," he coos as he kneels to grab the ball. He places it again in Dean's hand, then presses a firm kiss to the boy's cheek that isn't resting against the cool surface of the desk. It earns him a soft smile. 


That smile won't be there much longer. 


"Now, I usually punish my subs with ten lashes. But you've been sent here three times already this week, so I think thirty is best." Dean whimpers but squeezes the ball tighter, refusing to let it go. 


When Castiel begins to pull down Dean’s jeans, Dean startles. They both freeze for a moment but then Dean lifts his ass in the air like an invitation, his hand still firmly holding the ball, and Castiel continues.


Once Dean’s jeans are down to the middle of his thighs, Castiel runs a hand over the boy’s black lace panties. “Well, what do we have here?”


Dean whimpers, the noise turning into a low groan when Castiel takes both lace covered ass cheeks in his hands and squeezes hard. “I wonder what all your buddies would think if they found out Dean Winchester wears pretty panties. Should I tell them?”


Dean turns his head the best he can to look up at Castiel with wide, terrified eyes. He shakes his head frantically while begging Castiel through his gag not to tell. Castiel just chuckles. “I guess it can be our little secret. If you’re a good boy for me.”


With a nod of agreement, Dean rests his head back down on the desk and lifts his ass again, as if he’s telling Castiel that he’s ready to show him how good he can be. 


The sound of Castiel yanking his belt off makes Dean shiver. He jumps when the soft leather is dragged from one ass cheek to the other. Even through the panties, it feels amazing, making Dean’s body erupts with goosebumps. His skin feels like it’s on fire. It only gets worse when his panties are removed painstakingly slowly, the fabric whispering against him in the best way. 


Once his ass is exposed, Castiel folds the belt in half and starts to drag it back and forth again. Every few seconds, Dean tenses like he’s preparing himself for a hit. Eventually his body completely relaxes, though. He even finds himself humming. The sensation is nice. Like someone’s tickling him and -


Oh fuck . The first crack of the belt is so loud that Dean jumps from it more than the actual pain. He lifts his head slightly, looking at the door. Surely Mr. Novak knows they have to be quiet. They’re at school. In the middle of the day. 


Dean doesn’t have time to worry about it. Not when the blows start raining down so fast he’s unsure how Mr. Novak can even keep count. By the time the belt stops striking him, Dean’s ass feels like it’s been set on fire. It throbs with the beat of his heart and he finds himself reaching back with a hand, wanting to rub away the pain. 


“No no no. None of that,” Castiel chides, grabbing Dean’s hand before he can get to his destination. He collects Dean’s other hand as well and presses them together, using his belt to secure them above the boy’s head. “There we go. You still have five left, but I guess I’ll just have to use my hand for those.”


A tear leaks out of Dean’s right eye as he wonders if he can take much more. He still has the ball in one of his hands. Part of him wants to drop it. The other part thinks he’s strong enough to take this. He wants to be good. Not just for the whole panties secret, but for Mr. Novak in general. Dean wants more than anything to be Mr. Novak’s good boy. He needs to be. 


Castiel is a good dominant. He knows exactly what Dean is thinking. With one hand, he gently guides Dean’s face until their eyes are locked. Castiel’s other hand starts to stroke soothing circles on his abused ass cheeks. Dean hums in appreciation, looking up at Castiel with vulnerable eyes. 


“You’re being so good for me, Dean. Such a good boy.” Every muscle in Dean’s body relaxes, and he releases a soft sigh of relief. Castiel smiles. “Can you keep being good for me? For five more spankings?”


Dean nods. “Good boy.”


Before Dean can prepare himself, Castiel stands up straight again and lifts his hand. He spanks Dean once on his right cheek, then on his left. The boy squirms and whimpers, but he’s still squeezing the ball tight. Deciding to test Dean with his final three spankings, interested to see what the boy can take, Castiel lets himself loose. The first slap is his left, then on his right, then right over his crease so both cheeks are abused. Each hit was harder than Castiel thought he had in him, making his hands itch and vibrate with pain. His handprints are bright red over the already deep pink skin of Dean’s ass cheeks. When he looks up at the boy, he sees he’s quietly crying. 


Castiel releases Dean’s hands as he whispers softly, “That’s it, Dean. You’re a good boy. Such a good boy for me.” 


When the tie is removed from Dean’s mouth, he sniffles and licks his lips. He tries to thank Mr. Novak, but his voice cracks and breaks. 


With soft hands, Castiel guides Dean off the desk and turns him around. When they’re face to face, Castiel wipes Dean’s cheeks clean and smiles at him. Dean relaxes, smiling back. 


“Does my good boy want a reward?”


Dean’s eyes light up. “Yes.”


“Yes please, sir,” Castiel corrects, raising an eyebrow. 


With a shiver, Dean echoes back, “Yes please, sir.”


“On your knees.”


“Oh-” Dean pauses, feeling unsure. That doesn’t sound like a reward. He trusts Mr. Novak, though. He has no fucking idea why, but he does. It’s something in those blue eyes. They’re gentle, even when Mr. Novak is pissed off and yelling at him. Even when he was spanking him moments ago. Mr. Novak looks at Dean like Dean’s precious. Dean likes that. 


Castiel’s shocked when Dean says nothing more, and silently sinks to his knees without complaint. 


“Now, earlier you said there’s a difference between a blowjob and sex.” Castiel reaches down, cupping Dean’s right cheek and stroking a thumb over his pretty pink lips. “You offered to show me. I think I’ll give you the chance now.”


A beautiful blush spreads from Dean’s neck to the tips of his ears. He looks at Mr. Novak’s crotch where his erection is clearly trying to escape the confines of his dress pants, then flicks his gaze back up at him. 


“What do you say, Mr. Winchester? You want to show me?”


“Yes.” When Dean sees Mr. Novak raise an eyebrow, he quickly corrects himself. “Yes, sir. Please let me show you.”


“Good boy.”


The praise makes Dean shiver, his pupils dilating and his lips parting as he sucks in a sharp breath. It makes Castiel grin ear to ear. He knew Dean was a needy, submissive bottom just waiting to be tugged out from under the badass exterior he shows everyone else. He never thought Dean would be such a great submissive though. 


Castiel wants to keep him. Especially when he feels Dean’s nervous hands gently tugging his zipper down, green eyes flicking up at him to ask silent permission. Castiel cards his fingers through Dean’s hair and smiles down at him. “Go ahead, baby. Take it out.”


With an eagerness that Castiel knows would embarrass Dean if the boy wasn’t so turned on, he pulls at Castiel’s pants and boxers until his cock is springing free. Dean licks his lips and adjusts his knees so he’s at the perfect height. When Castiel’s cockhead is less than an inch from Dean’s mouth, he’s once again given big green eyes asking permission. 


Instead of verbally telling Dean to suck him, Castiel just tightens his hand in Dean’s hair to hold him still and uses his other hand to hold his cock steady as he guides it to Dean’s mouth. Dean opens for him immediately, but Castiel spends a few seconds just rubbing his leaking tip along Dean’s lips until they’re glistening with precum. 


“Look at you. So needy. So eager. But so patient and good for me.” Dean’s lips twitch into a slight smile, his eyes widening in a hopeful happiness. “I bet I could just jack myself right here, like this. Come all over your pretty little face. You wouldn’t even care, would you?”


“No, sir,” Dean admits in a husky whisper, his breath falling on Castiel’s cock and making him groan. 


“You’d probably even like it, wouldn’t you? To be covered in my cum? To be marked as mine?”


Dean nods rapidly. “Yes. Yes, sir. Yours.”


Castiel’s knees start to weaken, and he has to remind himself to get his shit together. This is a teenage boy. Eighteen or not. He’s a fucking student. He can’t be Castiel’s. This has to be a one time thing. 


“Suck my cock, then,” Castiel finds himself saying, even though he knows how wrong it is. Even though he never planned to take it this far. “Show me how much you want to be mine.”


With a soft whimper, Dean’s diving in and swallowing him down. The boy’s done this before. He’s good at it. The perfect amount of suction, bobbing, and tongue. When Castiel bucks his hips, pushing his cock further down Dean’s throat, the boy gags but takes it. When Dean begins to bob again, he makes sure the cock goes that deep every time, wanting to show Mr. Novak that he cares about his pleasure. Wanting to prove how good he can be. 


That’s when Castiel breaks completely. He grabs two fistfuls of Dean’s hair and holds him still as he begins to snap his hips forward fast and hard. Dean moans around his cock as drool leaks out the sides of his mouth. He just stares up at Castiel in awe as Castiel fucks his mouth. It’s his undoing. 


“Gonna come, baby.” He releases Dean’s head. “Pull away if you don’t want to swallow.”


Dean doesn’t move away. If anything, he gets closer, pushing Castiel down his throat until his balls are resting against Dean’s chin. Castiel spills down the boy’s throat with a few hot bursts of cum. Dean chokes and coughs, probably not prepared for what it would be like for the cum to be that deep in his throat as he tries to swallow, but he’s fine after a few seconds. 


Looking dazed, Dean blinks up at Mr. Novak through blurry eyes. He can feel his chin slick with spit, and possibly some cum. His cock is achingly hard and leaking a pool between his thighs, but he doesn’t care. He just wants to know if Mr. Novak is happy with him. 


Castiel gets on one knee in front of Dean, swiping a soft thumb along his chin to clean him up. When he puts the thumb to Dean’s lips in curiosity, he’s thrilled to find that Dean immediately takes it into his mouth and sucks it clean. 


Moaning, Castiel informs him, “You’re so fucking good. So good for me, Dean.”


“Thank you, sir.” Dean leans forward when Castiel starts to take his hand away, chasing his touch. When Castiel cups his cheek, Dean nuzzles it and sighs in relief, resting the weight of his head in Castiel’s palm. 


Yup. That’s it. Castiel is a goner. 


With his free hand, Castiel reaches down and gently tugs at Dean’s cock. Dean whimpers and leans further into Castiel’s touch, wiggling his hips a little to gain more friction. It’s not long before Castiel is spitting on his hand and picking up the pace, pulling filthy, beautiful sounds from Dean. 


“Gonna - gonna,” Dean breathes, unable to finish. 


“Go ahead. Come for me.”


Just seconds later, Castiel’s fingers are being covered with cum. Before Dean’s done spilling over his principal’s hand, before Castiel can pull away, Dean’s launching forward and crashing their lips together in a violent, hurried kiss. 


He immediately apologizes when Mr. Novak pulls away. “I’m sorry. That was bad. I’m so sorry, sir. I shouldn’t have-”


“Hush,” Castiel whispers, placing a finger over Dean’s lips to quiet him. The boy listens, but deflates. “You did nothing wrong. Thank you for kissing me. I like it very much.”


This makes Dean perk up, his cheeks flushing. He even gets the courage to ask, “Can I ever kiss you again?”


With a soft laugh, Castiel helps Dean to his feet and begins wiping his hand and Dean’s cock off with tissues. When Dean’s clean enough, Castiel pulls his panties and jeans back up, zipping and buttoning them for the boy. 


His boy. 


He may be going to hell, but he’s keeping this one. If Dean wants to be kept. 


“Sir?” Dean whispers, his voice trembling as he peers up at Castiel through his lashes. 


Castiel kisses Dean’s forehead, then says, “You can kiss me again, Dean. Soon. If you want to be mine.”


“Like your boyfriend?”


“In a way.” Castiel looks at Dean, searching his eyes for hesitation or fear. There isn’t any. “Do you know what it means to be a submissive, Dean?”


“Like Fifty Shades of Grey?”


This makes Castiel roll his eyes. “Not at all, but that’s a start I guess. I want you to do some research for me. Due tomorrow. I’ll be expecting you before classes start in the morning to discuss this.”


“I don’t need to,” Dean blurts. “I want to do that. I want to be yours.”




“I’ll do the research. I’ll do whatever you want. But I’m telling you now, I won’t change my mind. I want this. I’ve never,” Dean pauses, glancing down at his feet and tangling his fingers together. Castiel doesn’t understand why he’s suddenly so nervous until Dean mutters, “I’ve never felt like that before. It was like I was floating. It was - I dunno. Safe, I guess. That’s stupid. I’m sorry. I’m so stupid. Just forget-”


“No, Dean. None of that. You are far from stupid.” Castiel grabs the boy’s face and forces Dean to lock eyes with him. “I’m glad you felt that way. I’ll make you feel that way for as long as you’ll have me. But do the research tonight so when we talk tomorrow, you understand what I’m saying. Understood?”


Dean nods. “Yes, sir.”


“Now go to class.”


“Yes, sir.” 


Dean takes a few steps away from him, heading toward the door, and Castiel’s fingers itch to touch him again. It’s like he’s addicted.


"Hey," Castiel says softly, grabbing Dean's hand and tugging him into his arms for a gentle embrace. "Next time you feel like misbehaving, you're coming to my house. I'll put you in my playroom and show you a real punishment."


Dean shivers before peeking up at Castiel through his eye lashes. "What if I want to be in your playroom, though?" 


"Then behave. Trust me Dean, the playroom is much more fun as a reward."


"Okay." Dean gulps, cheeks flushed bright red. He nods frantically. "Yes. Okay. Best behavior, sir. I promise."


"Yeah," Castiel says with a soft laugh. "We'll see."