#high school dean

[seasononesam]

1x03 // 4x03 | insp

You know what? I'm sick of this attitude.  Family business, Mary... family.

[holylulusworld]

Naughty High School Adventures (1) - Kinktober 28

Summary: Why do you date an asshole? That’s what Sam and Dean want to know.

Pairing: Janitor!Sam Winchester x Teacher!Reader x Gymteacher!Dean Winchester

Warnings: shy reader, two guys want one girl, awful boyfriend, mentions of cheating, a hint of making out, implied cucking/cucking, jealous Dean, language

A/N: Because I have no self-control, I turned this one into a mini-series.

Kink: Cucking

Idea by: @moosekateer13

Kinktober vs Flufftober 2023

“Sonofabitch!“ Dean barely has the time to jump aside as the guy he despises almost runs him over with his brand-new bike. “Don’t you have eyes, idiot! This is a high school parking lot, not a racetrack!”

“What the fuck!” One of Dean’s colleagues exclaims loudly. She barely had the time to hide behind Dean’s car to not end up under the man’s bike. “What a loser!”

“Exactly,” Dean agrees. “That dick-less loser always makes such a fuss. I can’t believe Y/N is dating that asshat.”

“Well, she was lonely for a while. Maybe Y/N believes no one else is interested in her. She’s a little shy and always looks a little nerdy. Her taste in clothing isn’t better.”

Dean furrows his brows. “What?” He cocks his head to glance at his colleague. “But she looks cute. Did you see her outfit today? I liked the gray sweater, pleated skirt, and black flats. She looked so small next to me.”

“What is going on?” Sam, Dean’s younger brother and the new janitor at the high school asks. He cocks his head to watch his brother frown deeply. “Isn’t that the cute teacher you tried to hit on?”

“Shut up, Sammy. Her douchebag boyfriend almost ran me and Lisa over,” Dean grunts as he must watch the teacher he tried to invite for weeks walk toward the douche almost running him over. “I hope she doesn't get on that bike. That asshat doesn’t even wear a helmet.”

Sam grins. “Dean, she won’t get on that bike. Y/N is a responsible person. Plus, she’s got like ten books, her laptop, and a bag.”

“You're right,” Dean nods thoughtfully while watching you and your boyfriend. “Bastard didn’t even offer to take her books or shit.”

“Hmm…maybe we should lend her a hand?” Sam dips his head to look at his brother. “You know, to help her carry the books and all.”

“She’s talking to her…” Dean frowns as the cute teacher turns back around to stomp toward the building. “Uh-oh, I guess she’s mad at him. We should check on her. Right?”

“It’s the right thing to do, Dean,” the younger brother agrees. “The building is almost empty, and I need to lock it. Everyone is already on his way home to enjoy the weekend.”

“Oh…OH!” Dean looks at his brother, smirking darkly. “We shouldn’t leave her all alone at the building. That would be ungentlemanlike.” 

“Y/N,” you startle when Dean Winchester, the gym teacher, enters your classroom. You wipe your eyes and try not to show that you cried. “Is everything alright? My brother wanted to lock the building and saw you walk back inside.”

“I-“ you sigh deeply and shake your head. “My boyfriend bought an expensive motorcycle. I can’t believe he’s a thoughtless dumbass.” You huff. “My car broke down, and I asked him to pick me up. And he…he comes here with a brand-new bike while I cannot afford the money to repair my car. We talked about sharing finances and he goes off, spending money on things like this.”

“Sweetheart, you shouldn’t waste your time on that asshole,” Dean steps inside the room, eyes trained on your face. “How about I drive you home, Y/N?”

“Really?” You gasp. “You will?”

“Sure thing, sweetheart.” Dean brushes your excitement off. He acts as if it’s not a big deal for him to drive you home. Your boyfriend always made a fuss if you dared ask him to drive you somewhere. “But I need to help my brother first. I promised to help him collect the balls at the gym.”

“Oh, I can help too,” you lick your lips. “He’s always so kind.” You get up from your chair, pressing your thighs together at the thought of spending time with Dean and his younger brother. “He helped me more than once since he’s working here.”

“Sammy is a nice guy, and smart. He’s just a little shy around pretty girls,” your colleague flashes you a grin. “He only works as a janitor to make some extra cash for Stanford. He’s going to be a lawyer.”

“That’s great,” glancing at the books on your desk you sigh deeply. “Thank you for offering your help. My boyfriend is…”

“An asshole?” Dean offers, making you gasp. 

“DEAN!”

“It’s true, sweetheart. A man shouldn’t treat you like he does,” your colleague argues. “I saw how he treated you firsthand today.”

You huff. “Can we not talk about him? I’m already fed up. We wanted to spend the weekend at his parents’ cabin, and now he’s having a sleepover with his buddies to do God knows over the weekend.”

“Let’s forget about your deadbeat of a boyfriend. How about my brother and I show you how a woman like you should be treated,” Dean grabs your books and laptop. “I promise we won’t do anything you don’t like. Give it a thought.”

Dean flashes you a smile making you go weak in the knees. He’s holding out his free hand, offering something more than a ride home. 

You take his hand without hesitation and say, “Will your brother be around too?”

“Oh sweetheart, he cannot wait to get his hands on you.”

You didn’t know what you expected would happen if you followed Dean into the gym to join his brother. But you knew they were up to more than chit-chat.

At first, you talked a bit and helped Sam pick up the balls. He was a little shy but smiled the whole time. “Thank you for the help. This way I can finish work earlier.”

“Sammy is a little shy,” Dean suddenly stood behind you to whisper in your ear. “But I know he’s burning to bury his fat cock in your sweet cunt, Y/N. What do you say? Do you want to have two men satisfying your needs for once? I know that limp-dick of a boyfriend didn’t do you right.”

“Dean, I—” you licked your lips. Sam was suddenly more interested in cupping your face with his large hands than cleaning the gym. “We barely know each other. I mean…you’re hot…shit…did I say this loud?”

“Just say yes, sweetheart, and we are going to be so good to you,” Sam smirked at his brother’s words. “We will make sure you can’t walk straight after we are done with you.”

Dean nuzzled you. “Dean and I will make you feel so good, Y/N. Since you started working here, we wanted to make a move.”

“You did?” You breathlessly replied. Having the brothers so close arouses you more than anything. The thought of having them both makes you dizzy. “Really.”

“I’ve been walking around with a raging hard-on every day since I saw you in your short skirts and little blouses for the first time. Do you want this? Do you want Sammy and me to take care of you sweetheart?”

“Yes,” you spluttered before you could change your mind. “I-we…he’s not very interested in me lately. I guess he’s cheating on me or shit.”

Three hours later, …

“What this?” Your boyfriend opens the video you sent him some hours ago. He presses play, and his eyes widen.

“Hey there, you sonofabitch,” Dean taunts. “Do you want to know how your now ex-girlfriend will spend her weekend? How about I tell you.”

“She will be full of cock, just like right now…”

“I hope you’ll like the show…” Sam adds. “We will see if you get to watch next time…”

Part 2

Tags in reblog.

[girlsvmonsters]

Art created for the @destiel-shit-post-mini-bang

Apologies, I don't have a story link. But I still wanted to share the art I created for the event cause I had a lot of fun with it.

Castiel takes Dean to prom (after getting age-regressed to high schoolers thanks to a witch).

[thescarleteagle]

I love how in the beginning Dead Girl Walking and the Dead Girl Walking reprise, the beats are different from each other. Compared to most musical reprises, which are usually the same song just slower or faster, this particular duo shows Veronica’s character arc in a great way. In Dead Girl Walking, Veronica is at her low and just wants something to put her out of her misery induced by Heather C., therefore the beats are more mysterious and ominous as she walks by Jd’s house, wanting to be his “Dead Girl Walking”, but in the reprise, she is a literal dead girl walking because of him. In the reprise, the beats are driving because she has a mission and an actual purpose, she’s not a Heather anymore, or a condemned high schooler, she is simply trying to rid herself of the mess she created. By the reprise, she has grown from the easily manipulated Heather, to the smart and powerful Veronica that we know and love, and I think this small detail reflects that.

[animemusicbrackets]

Anime OP Showdown!!!: Round 2B

"Sakura Kiss" - Chieko Kawabe (Ouran High School Host Club)

VS

"History Maker" - Dean Fujioka (Yuri!!! On ICE)

[cephalopodsquad]

danny is the only man in pro wrestling i respect

[clever-name]

emphasis on the dean

[suncaptor]

I think Dean might throw a bit of a fit if he found out Sam liked men but not because he's being homophobic at Sam but because he's accusing Sam of lying to him.

[ilovejohnwinchester]

does anyone else ever forget how long ago 2005 was and then Dean and Sam are shocked that John figured out how to text on a phone and Dean asks Sam what MySpace is because it’s the sort of thing only a college kid would have heard of?

[pinkdean]

Sorry the post about 10x05 fan fiction got me thinking

[vendettasfanfictioning]

Nerd/jock destiel but Dean's the nerd and Cas is the jock. OR jock/cheerleader, Cas is still the jock but this time Dean's a cheerleader. OR EVEN BETTER these both happen and everyone's happy.

[wh-t-ver]

No, because I will never shut up about Mary Winchester and how she doomed her children. She makes a deal with a demon to save her lover, and I understand that, but she doomed her life, her husband, her CHILDREN. She didn't know, but she pretended like that deal never happened for YEARS. She marked her sons, made it impossible for them to have the normal life she wanted for them, and when she comes back, she reveals her true colors, falls back into the hunting lifestyle so easily, and it disturbs Dean to his core because HE KNEW his mother before she died, even briefly. Sam isn't disturbed because it's all he's ever known. A parent going on hunts is so natural for him. He wasn't thrown into this life, he was raised on it. Dean was thrown into it, and he adapted too fast. He became a mother and a father for his brother, growing up too fast.

[freakwiththeknifecollection]

This one was such a hit, have this one too

[profoundbondfanfic]

In Secret Places

In Secret Places by Brinchestiel Rating: Mature Word count: 106k

Seventeen-year-old Castiel Krushnic doesn’t trust, doesn’t cry, and he certainly does not love. Life hasn’t exactly been the easiest ride, so when he gets stuck living with Missouri Moseley and the Winchester brothers in the dead-end town of Janesville, Wisconsin, life seems like it's set to get a whole lot worse. What he learns, however, is that things in life aren’t always as they first appear. And people are never who you thought they were. They can grow, change, and bloom but only if you let them. "If you look the right way, you can see that the whole world is a garden." - The Secret Garden by Frances Hodgson Burnett.

Teen Castiel has not had an easy life.  His brother Gabriel steals a car while Cas is with him and gets thrown in jail.  When Cas gets home, his mother kicks him out, and her boyfriend isn’t going to lose any sleep over his absence.  Homeless and without any options, he’s flipping between sleeping on the streets and the local shelter.

But Cas is a survivor if he’s anything, so when his lawyer offers to take him home where her two unofficial foster kids live, he’s all in.  Except for that crappy temper of his, the fires flamed in his chest by rejection and anger. He lashes out and is on his own, far from home with nowhere to go.  But someone comes to his rescue.  A new friend, a new reason to be afraid to step out of line, a new person he has to please to maintain a warm place to live, food on his belly, and an easy supply of cigarettes and pot.

But Alistair is an asshole and the people he hangs out with give Cas the complete creeps.  So it’s not the worst when Alistair kicks him out because he steals some money and camping gear and ends up roughing it in the abandoned lot behind Old Man Singer’s house.  Until his stuff is stolen and he has nowhere to go but back to Missouri’s where Dean, who hates him, and his little brother Sam live while their Dad is off somewhere crying in his whiskey.

The relationship between Cas and the Winchesters is hard-won.  Deep down, Cas is a good person, though, who stands up for Dean when he’s bullied and who smiles softly as Sam, and who is really fucking smart when he actually tries.  Dean doesn’t want to like him, but the more time they spend together, the more they realize their traumas are similar and have forged them both in fire, the harder it is to ignore that flutter in his stomach when he looks at Castiel’s blue eyes.

This fic is a nice long read with an in-depth examination of the boys’ psyches.  Their backstories are intricate and full of humanity.  Their budding relationship is so engaging, at times, it's easy to forget about the rest of the plot, and then it swoops back in and punches you in the gut.  This is a happy ending story, even if at times you wonder how it’s ever going to get there.

[number1tailsdollfan]

”AND SO I BUILT A BOMB!!”

[jellybracelet]

Thinking about how Sam and Dean probably went to school on long island... ♥️