#coach!dean

She’d glance up every now and then, make it look like she was paying attention, but it wasn’t until she heard the principal utter the name of the new coach that her head jerked up, eyes wide as he walked in.

Dean Winchester.

“Dean’s a past student as well, like a few of you, and we’re really glad to have him…”

Y/N never thought she’d see him again in a million years. He was practically a ghost story around town after high school finished and he left soon after. He was the star quarterback, dated the captain of the cheer squad, and never knew Y/N existed. Though his friends had certainly said a few choice words to her during those days. No matter how much she had tried to hate him, he was completely crush worthy back then, and nothing had changed as she watched him shaking hands with teachers.

Her gaze wandered over his physique, his white polo shirt tight across his chest and arms, the edge over dark khaki pants. He had clearly grown more into his looks, which is saying something considering he was already a heartthrob in school. Sitting forward, she put her head down and got back to her work, determined to not be distracted by him again. She would often find herself daydreaming in class whenever he would walk in, late of course, and she always got in trouble for staring off into space.

“Y/N.”

Taking a deep breath, she closed her eyes and knew it was too good to be true to be able to ignore him. Lifting her head, she saw him smiling down at her before he took the seat across the table, crossing his leg as he sat back.

“It’s been a long time,” he stated, a smirk appearing on his face.

“Not long enough,” she mumbled under her breath, looking down at the essay in front of her.

He huffed a small laugh, hearing her clearly. “Still a firecracker.”

“Still?”

“You haven’t changed a bit,” he said, leaning forward with his forearms against the table, his hands clasped as he stared into her eyes.

Y/N felt her cheeks heating up under his gaze, but quickly stood up and gathered all her students’ papers in her hands. “That kind of observation would’ve required you noticing me in the first place, Winchester.”

Without giving him a chance to hit her with a witty remark, she made a beeline for the staff room door and made her way down the halls. She had no interest in going down memory lane, especially when she didn’t have the best high school experience.

She’d act professional, but there was just no way she was going to give Dean Winchester even a second of her time.

The next few weeks passed in the same way. Dean would try to start up a conversation whenever he saw her, and she’d give him one-word answers or none at all. She hoped he would just get the hint and give up, but she had to admire his persistence even if she found it frustrating. She wasn’t sure if he had some other agenda, that maybe he was trying to get her attention only to throw a milkshake in her face like one of the football guys did back in the day, but she had to remind herself that she wasn’t a teenager in high school anymore. She was a teacher, he was a coach, and they had grown since then.

A sunny day was welcomed by everyone, a nice change as they headed into colder weather and weren’t going to have days like this soon. Y/N sat outside at one of the lunch tables, taking her work and her food with her, hoping that the good weather would help with the dread of grading tests. If one more student got a question about the Civil War wrong, she was about to scream.

“Great weather, huh?”

Dean sat down on the bench across from her, turkey sandwich in hand as he smirked. Y/N sat back in disgust as she watched him glance over the tests laid out on the table.

“History, huh?” he muttered around a mouthful, shaking his head. “Could never stay awake in that.”

“Oh, trust me, I know,” she scoffed, rolling her eyes. “I nearly had to swap seats with you because you weren’t paying attention, but I couldn’t-”

“Because of your glasses,” he finished her sentence, shocking her with the memory. “You couldn’t see anything from the back. I remember.”

“Y-You do?” she asked, her voice low as she continued to stare at him. Of all the things she was expecting him to say, that wasn’t one of them.

He gave her a firm nod. “Yeah, I mean… I felt bad that Ms. Jones singled you out.”

“Well, it was forever ago, so you’re forgiven,” she stated, sighing. “I just… can’t believe you remember that.”

“I remember plenty of things about you,” he countered, leaning forward on his forearms as he looked into her eyes.

“Really?” she asked, raising an eyebrow, sceptic about what he just revealed.

“Yeah,” he replied, easily as he shrugged his shoulders. “You didn’t give a shit about what people thought about you, and uh, well I guess I wish I was more like that. Wouldn’t be in the mess I’m in now if I was.”

She frowned, watching him dust the crumbs from his sandwich off his fingers. “You and Suzy?” She had guessed that they were still together after high school, but clearly something had gone wrong.

“Divorced, three months ago,” he stated, a huffed, bitter laugh leaving him. “Moved back home to get away from her, now I’m staying with Sam and his family until I can get back on my feet.”

“Dean,” she breathed, her voice soft as she tilted her head to make eye contact with him. “I’m really sorry.”

One side of his mouth pulled up, nodding slowly. “Gotta start fresh somehow, right? Plus, it’s got perks, Eileen’s a good cook.”

Y/N chuckled. “You and food.”

“Hey, it’s one of the two greatest pleasures in this world,” he declared, emphasizing his point by taking a bite of his sandwich.

“And what’s the other?” she asked.

He swallowed, looking at her pointedly as he smirked. “I gotta spell it out for ya? Draw a diagram?” he winked.

“Oh my god,” she groaned, closing her eyes as she quickly realized. “We’re in school, Dean.”

“It’s not like they heard,” he observed, looking around the school grounds. “It’s not like they’re not already doing it, either.”

“Okay, that’s my cue,” she announced, standing up quickly and collecting the tests.

“Hey, come on, don’t leave,” he pleaded, his hand slipping over hers to stop her. “We were good, first time you haven’t looked at me with repulsion. I call that a win.”

“These aren’t gonna grade themselves,” she stated, flicking through the tests with her thumb.

“I’ll help,” he offered, his smirk turning into a grin as he knew he had her. “Just you know… give me the answer sheet.”

Y/N bit into her lip as she thought about it for a moment. For once he hadn’t gotten on her nerves, and she found herself thinking about those days when she wanted nothing more than for him to notice her. Now he finally had, and it felt genuine. She just hoped she was right.

There was only one way to find out for sure.

“Okay,” she whispered, sitting down again and handing over half the pile to him, followed by the answer sheet. “Let me know if you can’t decipher someone’s handwriting…”

“Sure thing, sweetheart,” he muttered, smiling at her before he looked down at the papers.

Feeling her cheeks heat up and butterflies in her stomach from the pet name, she put her head down and got to work, trying to ignore whatever she was feeling.

Y/N’s heels clicked against the path as she walked towards the football field. She watched as Dean yelled different instructions to the team, the boys moving with each play their coach called out. She sat down on the first bench of the bleachers, crossing one leg over the other as she stared down at the post-it note Dean had left on her desk.

Come by after practice. Something I wanna show you.

- D

It had been a couple of weeks since she first let her guard down with him, and things had actually been really good. They were spending almost all their lunches together, talking and laughing as they reminisced about the past. He had apologized on behalf of anything the guys had said to her back then, but she couldn’t accept it when he wasn’t the one who had done anything wrong. She was very much crushing on him again, as much as she was trying not to, but with those green eyes and kind smile how could she stop herself?

She lifted her head as she heard Dean blew his whistle in one long breath, calling the end of practice.

“Alright, nice work! Hit the showers!”

Dean spotted Y/N standing up from the bench, wearing a maroon dress and black heels, causing a smirk to grow on his features as he walked towards her. She felt her heart beating faster as he came towards her, the school’s red jacket over the polo shirt and his own dark blue jeans. They stood in front of each other for a moment, their eyes locked as they both thought of something to say.

“Ready?” he asked.

“For what?” she laughed.

Offering his hand, she placed hers in it, feeling her heart skip a beat as his fingers closed over. They walked back to his office to pick up his car keys before they left the school building. He led her over to his car and helped her in before walking around to the driver’s side. She turned to look at him, wondering what he had up his sleeve as he pulled out of the parking lot and drove down the street.

They drove just to the outskirts of town, the open highway ahead of them until Dean turned down a dirt road. They slowly came to a stop at a clearing, the sun beginning to set behind the trees in the distance, bathing the sky in hues of pink and purple. He got out of the car just as she did, taking her hand once more and helping her sit on the hood as they looked up at the sky.

“So… what’s going on?” she asked, nudging her arm into him.

“You have to guess,” he replied, smirking.

“What? I don’t-” she shook her head, huffing a small chuckle as she couldn’t understand what he was trying to do. “Okay… twenty questions?”

“Sure,” he agreed, still grinning.

“Okay… is it something I can see?” she asked, glancing around them at the clearing.

“Nope,” he muttered, smugly.

“Is it something small?” she questioned.

“Yes,” he replied.

“Okay… something I can touch?”

“Yeah.”

“Something I can eat?”

“No.”

Y/N continued trying to guess what he was talking about until she finally gave up. There was just no way that she was going to get it.

“Alright, fine,” he gave in, reaching into his pocket and taking out a small, rectangular box. He glanced up at her as he opened it, watching the disbelief flash across features.

“Oh my God, how-how did you-” She took the box from him, lifting the silver necklace out, her thumb running over the small, dragonfly pendant that hung from it. “I lost this, how do you have this?” she asked, shaking her head in shock.

“You dropped it after a P.E. class and I was going to get it to you, but I guess I forgot. Then I thought I lost it too, but I found it in a box of my stuff a few days ago,” he explained, looking between the necklace and her.

He took it from her hands and opened the clasp, reaching behind her neck and locking it in place. As he drew back, his face was close to hers, their eyes peering into each other’s. She never thought that when he first joined as coach that this would be the outcome, but she couldn’t hold in how she felt anymore. Y/N leaned in, pressing her lips to his in a soft kiss, a moan escaping her as he cupped her cheeks in his hands, the kiss becoming deeper.

It was exactly how she had imagined it would be, all those years ago when she would daydream in class. No. It was even better because it was actually happening.

Dean pulled away first, leaning up and pressing his lips to her forehead in a light kiss, making her smile. “Never dreamed we’d be here, huh?”

“I did, but…” She smiled, lifting her head to look into his green eyes, falling deeper for him than she ever had back then.

“I’m really glad it’s finally real.”

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You were an English teacher, and you loved everything about your job. The subject, your kids, the impact you made. You taught the juniors and seniors mostly; AP English was your specialty and kids had a semblance of respect by that age. You had been teaching at this school for almost five years, and there hasn’t been a teacher yet who has excited the other female teachers like Dean Winchester has. You sighed as you took one last look at yourself in the mirror; you knew the conversation that you were about to have with Dean wasn’t going to be pleasant. One of your kids, one of the football players, is failing your class… and it’s no pass, no play at this school. You knew that’s what Dean wanted to talk about when he stopped by the teacher’s lounge this morning and asked you to drop by his classroom whenever you had a minute. Well, it was your free period, and you had a minute. 

Your heels clicked as you made your way down the tiled hallway, stopping at classroom 7B and peering through the small window in the door to see if he had a class going on. He was sitting on his desk in his sweats, a picture of the cotton gin up on the projector screen, talking with his hands to a full classroom. Although Dean coached the varsity football team, he taught the freshman, and the freshman were the worst. You knew you weren’t supposed to say that as a teacher, but it was true. They had no sense of respect or boundaries of any kind, and it drove you up the wall. It’s why you stuck to teaching the higher grades. You took a deep breath before turning the door handle and pushing the door open. Dean looked over at you, a small smirk appearing on his lips as the whole class turned their heads to see who had interrupted their “learning”. As if they were paying attention anyway. 

“Ms. Y/L/N, welcome to American History,” Dean teased, motioning to the classroom around him. You rolled your eyes and began to walk over to him as he told the class to find the answers to some questions in their textbook. “What can I do for ya?” he asked with a sweet smile as he stood up from his seat on his desk and moved to sit in the chair behind it. 

“You told me to drop by when I had a minute, you had something you wanted to tell me?” you questioned, like you were reminding him of his words this morning.

“Oh yeah, about that. I need you to pass Ryan. He has to play this weekend,” he insisted in a hushed tone. You both knew that high school kids, no matter the age, are nosy little fuckers and any information they hear will spread like the plague throughout the whole school in minutes. You chuckled and shook your head.

“I’m not doing that,” you replied with a shrug.

“Y/N, please… he’s the star quarterback, we need him or we’ll lose for sure.”

“Well, Ryan should have thought about that before he copied and pasted his entire essay from Wikipedia,” you retorted, your tone harsh but still hushed. 

“Y/N, I know you don’t know me all that well, but please. I won’t ask for any more favors. I’ll punish him in other ways for  cheating. He can sit out the next game if he doesn’t get his act together but this one decides if we go to the playoffs,” Dean practically begged. 

“Oooooh, are you two flirting?” You heard a prepubescent boy’s voice ask as the whole class stifled a giggle.

“Is that any of your business, Cooper!?” Dean boomed across the room, and the entire room immediately went silent. “Get back to work, stop looking for attention because you won’t get it from me. Not in this classroom.”

You hadn’t noticed the heat that was rising in between your legs until now. The dominance in Dean’s voice, the way he didn’t take any shit… and God, it had been so long since you last had a good lay. No, Y/N… don’t you dare, the angel on your shoulder began to tell you, but the devil on your other side reminded you that it had been so long since you last had a good lay, and that was enough to convince you. 

Dean turned his attention back to you. “So, about Ryan?”

“How about I think about it, and I’ll stop by after the day ends? Is there practice today?” you asked.

“No, no practice on Fridays. I’ll see you at 3:30, then,” Dean smiled. “Thanks, Ms. Y/L/N!” he called after you as you walked out the door, making you blush, but there was no one in the hallways to see it. Thank God. 

The rest of the day went by so incredibly slow; you were about to rip your hair out from the sexual frustration that you were feeling. It was taking everything you had to not space out watching the clock, daydreaming about Dean bending you over his desk and –

“Ms. Y/L/N, you okay?” You heard one of your kids ask. You cleared your throat and shook yourself out of your daydream. 

“Yes, Katie, thank you. Just tired,” you smiled, hoping that you weren’t blushing too hard. Thirty minutes, you reminded yourself as you took one last glance at the clock before going back to grading while your class analyzed a chapter from a book that you couldn’t remember the name of: that’s how preoccupied you were with dirty thoughts of Dean. 

Finally, the bell rang and your students practically ran out of the classroom as they always do, wishing you a good weekend. You waited for the hallways to clear of the other kids, before locking up your door and making your way once again to Dean’s classroom.

You turned the door handle to room 7B just like you had only a few hours beforehand, only to an empty classroom this time. Dean was sitting behind his desk, leaning back in his chair, his feet propped up on the surface in front of him. He was passing a football between his hands, and a smirk appeared on his face as you entered the room and closed the door behind you.

“Well?” he asked, in regards to the whole Ryan situation.

“Well… I don’t just go around doing favors for free, Mr. Winchester,” you hinted. You were much more confident now, without a crowd of 14-year-olds listening in on your every word. You stepped behind the desk and leaned your ass against it, causing Dean to put his feet back on the ground and sit up a little straighter. He raised his eyebrows at you.

“What can I do for you, Y/N?” he asked, his tone laced with a hint of mischief. 

“That is the question, isn’t it?” you replied sassily. 

Dean chuckled deeply. “What? You saw how I barked orders at Cooper earlier and now you want me to do the same to you? Is that it?” 

You were caught completely off guard, and your face showed it. How did he know? “How did you –”

“Please, your thighs clenched together the minute I told him to shut the hell up. Then you were practically shaking walking out of here. Not that any of them noticed; they’re the most oblivious group of kids I’ve ever seen. But… yeah, you didn’t do a very good job of hiding it, sweetheart,” he smirked, putting the football that he was toying with back on its stand. He stood up and took a step to the side; he was standing directly in front of you now and you let a whimper fall from your lips. “Lucky for you, it’s been ages since I’ve had a good fuck,” he chuckled, placing his hands on your hips, “and by the way you’re actin’,” he continued, moving his hands to grip under your ass, “I can tell that it’s probably been ages since you’ve had a good fuck, too, huh?” he asked, lifting you up onto his desk. All you could bring yourself to do was nod. Dean smirked and leaned in, his lips nearly grazing your ear as he continued in a whisper, “I know all that Lee and Fitzgerald and Homer has to get a little bit tedious, no?” He moved his hands below your skirt, slowly making his way up underneath it. Very slowly. “What book are your kids reading now? ‘The Great Gatsby’, right?” His hands were on your upper thighs now. You nodded; your breath kept hitching and you couldn’t bring yourself to speak. Looks like he wasn’t as airheaded as you thought he was. “That’s a good book,” he continued, as he forced your legs apart, causing your skirt to ride up. You let out a shaky breath accompanied by a nod and Dean chuckled at your obvious neediness. “You want me to stop talkin’ about books and just fuck you, don’t you?” He asked, using his fingers to push your panties aside. Your clit was pulsating; you had never been so turned on in your life. You nodded enthusiastically, wanting him to touch you already. He was hovering his fingers over your clit now; you could feel their presence but not them. “Funny, I could have sworn that you knew how to speak. You do teach the damn language, don’t you?”

“Y-yes,” you stuttered, your brain still foggy from what was going on. “Fuck, p-please.”

 Dean slowly pushed two digits inside you, drawing a moan from your lips. “Jesus, you’re so fuckin’ tight. How long has it been since someone’s been inside you, doll?” he asked with a breathy chuckle as he began to slowly pump his fingers in and out. 

“Fuck,” you breathed, grabbing hold of his bicep to keep yourself from falling back on the desk. 

“Answer me,” he demanded, plunging his fingers deep into you forcefully.

“Oh, fuck!” you yelped. “I d-don’t know,” you managed, throwing your head back as he started to curl his fingers inside you. Dean attacked your exposed neck with sloppy kisses, the cold air against the wet spots he was leaving sending shivers down your spine. 

“God, you’re so fuckin’ wet,” Dean remarked, as he continued to pump his fingers inside you. “That all for me, doll?” 

You nodded, forgetting how to speak. With Dean’s breath on your neck and the way his fingers were stretching you open, you were surprised that you were remembering how to breathe, let alone speak. A gasp escaped you as Dean abruptly pulled his fingers from your cunt, his free hand finding its way into your hair before gripping it harshly. 

“I thought I told you to use your words, hm?” he hissed in your ear, his words going straight to your core.

“I – uh –” you breathed, your thoughts scrambled.

“Seems to me like you need a lesson in following direction, don’t you think?” Dean asked, not even bothering to wait for your reply before he maneuvered you into a bent over position on his desk. He swiftly pulled your skirt up, revealing the globes of your ass underneath, as you were wearing a thong. Without warning, a sharp smack was delivered to your ass, drawing a yelp from your lips. “Nuh uh, you shut that pretty little mouth of yours. Would hate for someone to hear us, wouldn’t you?” he growled, delivering another hit to your other cheek. 

You nodded. “Fuck, y-yes,” you breathed, resting your forehead on the cool surface of the desk as another smack was delivered to your ass. You counted about five before there was a stop, and you heard the swishy sound of sweatpants behind you before feeling your panties move aside and a cock moving between your folds.

Dean chuckled darkly as he felt your arousal gather on his tip before he pushed into you, a groan falling from his lips. “Fuuuuck, you feel good.” You whimpered in response as you felt his cock fill you. “What? My cock feel good, doll? Been too damn long since you’ve been stretched open, hasn’t it?”

“Mhm, y-yes,” you gasped, feeling his tip hit the back of your walls. 

“Show me. Show me how good it feels. Fuck yourself on my cock, Ms. Y/L/N,” he commanded, as he lifted his t-shirt up slightly to keep it out of the way – he wanted as clear of a view as possible. You yelped when a sharp smack came down on your ass. “You better start movin’ if you want me to fuck you long and hard in a minute. Show me how bad you want this cock.” 

You whimpered as you moved your hips backwards, your ass cheeks slapping against Dean’s thighs as you rocked yourself back on his cock. It felt so good to finally have someone inside you; your toys were simply not doing it for you anymore. 

“There you go, there’s a good girl… Fuck,” Dean grunted, as he grabbed your hips to still you, before thrusting into you fast and hard. 

“Oh, fuck!”

“Shhh, shh, shh,” Dean hushed, his hand making its way to the back of your head and fisting your hair, pulling you up to be flush with his chest as his other hand went to cover your mouth. “You know what happens to faculty who gets caught fuckin’ in classrooms, Y/N?” he asked between relentless thrusts. 

You nodded, squeezing your eyes shut to try and keep yourself from moaning his name.

“Yeah? Then be quiet, for fuck’s sake,” he grunted, his hands going back to your hips as he released you from his grasp. You dropped your upper body back down to the desk, your hands gripping the edge of it. You were so close – all it would take to get you there would be –

You held in a moan as Dean’s fingers came around to rub circles on your clit, bringing you to the edge almost instantly. You could tell his thrusts were becoming sloppier – he was close, too. 

“God, I can feel you baby, you’re close, aren’t you? You wanna cum?” he breathed.

You nodded. “Yes. Fuck, I’m gonna –”

“Cum, cum for me. Cum on this cock,” Dean grunted, as he chased his own high. 

It’s as if his words triggered something inside you, your orgasm coming seconds later. You spasmed underneath him as he continued to fuck you through your high, nothing but heavy panting filling the room as both of you were concerned about making too much noise. 

“Oh, fuuuck,” Dean moaned, as he thrusted one final time, pulling out quickly before aiming his release at your lower back. “Christ,” he breathed, shivering a little as his high rode out. He leaned over to pull some tissues from a Kleenex box on his desk, quickly wiping his seed off of you before you stood up on shaky legs. You quickly pulled your skirt back down, the both of you trying to make yourselves look presentable again. 

After a few seconds of semi-uncomfortable silence, you moved out from behind his desk and cleared your throat. “I guess… I’ll see what I can do about the whole Ryan situation, Coach.”

Dean shot you a cocky smirk. “‘Preciate it. I’ll tell him to stop fuckin’ around in class and pay attention. Not sure how they lose attention, really. I wouldn’t be able to look away if you were my teacher,” he winked. 

You rolled your eyes before turning around, starting to make your way to the exit. “Dean,” you paused right before you reached the door.

“What’s up, sweetheart?” 

“Just – um – if you ever need another favor…”

“Hah, yeah. I know who to ask,” he chuckled as he sat back down at his desk. “Hey, Ms. Y/L/N,” he said, as you reached for the door handle. You stopped to listen. You could hear him throwing the football in the air and catching it again. “I fuck outside of favors, too. Just so you know.”