Hot For Teacher
Summary: He never forgot the teacher that had the most impact on him.
Prompt: Dean Winchester, in class, crushing on the teacher
Pairing: Dean Winchester x older!female!teacher!reader
Word Count: 5643 words
Warnings: fluff, crushes, slight angst, some mentions of John’s stellar parenting (don’t @ me, I love him, but I can be character critical), smut (nothing underage), flashbacks, reader is approaching forty, some humor about sex in later life.
Ao3 Link
“I’m telling you, man, this isn’t our thing,” Sam dismissed, following Dean through the doors into the high school reception. His brother grunted, flashing his badge at the security guard, who directed him to the desk where a gentleman was quietly reading.
“And I’m telling you, it might be.” Dean retorted, fixing a professionally fake smile onto his face, leaning on the desk with one elbow. “Agents Townsend and Daltry, we’ve got an appointment?”
The man peered at him over his glasses, pursing his lips for a split second as he glanced at the identification Dean was holding. After a second or two, he looked down, checking the clipboard wedged underneath his arm, before he smiled back at them. “Principal Matthews is in her office, I’ll let her know you’re here.”
Dean nodded, turning to move a little further away out of earshot. “We got five kids, swearing they saw a monster.”
“Yeah, highschoolers, seniors in their final year, acting out an urban legend,” Sam replied. “We’ve got bigger fish to fry right now.”
“Yeah? Got any leads?” the older man challenged. “Because last I checked, we had bupkis to go on.”
Sam sighed, but the argument was cut short as a door opened, and a tall lady with grey hair looked at them. “Agents?”
The office they stepped into was large, decorated sparsely with modern furniture, and a large flag behind her desk read “Gellar Gators, Go, Go, Go!” with a cartoon alligator in a football helmet. As Principal Matthews took her seat, both men turned to face her, though Dean was still inspecting everything.
“I assume this is about the recent attacks,” she started, folding her hands in front of her on the desk. “I’m not sure what I can tell you that I haven’t already told the police. They took all our security camera footage and -”
“Nothing to be seen,” Dean interjected with a nod, pulling out a notepad and a pen. “We’re just following up, seeing if anyone remembered anything different. Maybe something they didn’t want to tell the police?”
“Why wouldn’t they?” the principal asked, obviously confused. “I know some of the other children were saying it was a monster, but we all know how children can be.”
“We’re just trying to make sure no one else gets hurt,” Dean continued, keeping his tone gentle. “You’re aware that there was another victim last night?”
“Danny Elderman, yes, I’ve been told,” she murmured, shaking her head sadly. “His mother said he would make a full recovery though.”
Sam dragged his hand out of his pocket, gesticulating slightly. “All the attacks took place on school grounds, Principal Matthews.”
“And the police searched the whole place,” she defended. “I can assure you, Agents, we are taking this seriously. The students have all been instructed to report anything strange and there’s a curfew in effect.”
The brothers shared a look, realizing that this wasn’t going to get them anywhere. Dean cleared his throat, stepping a little closer. “We’re gonna stick around, speak to some of the students, if that’s okay.”
Principal Matthews nodded, gesturing to the door. “Of course, anything to help.”
Turning on his heel to head for the door, Dean’s gaze caught sight of a board, showcasing the faculty members with photographs and a brief description of their position. A single face jumped out at him, and for a moment, he was seventeen again. He froze, staring at it, before Sam’s fist jammed into his back and forced him to keep going.
Once outside, he stopped entirely, spinning around to face his brother. “Did you see her?” he asked, feeling a little breathless.
Sam’s face scrunched up. “Who?”
“On the faculty board. Miss. Y/L/N -” He laughed, shaking his head. “Outta all of the schools in the country -”
“Wait a minute,” Sam mumbled, remembering the name. “The math teacher from Luther High? That Miss. Y/L/N?”
“Yeah,” Dean replied excitedly. “Wonder if she remembers me?”
Sam snorted, rolling his eyes. “She’s probably married with kids by now, Dean, it’s been nearly twenty years. It might not even be her.”
“It was.”
“Fine, say it is. What are you gonna do? Go tell her you had a crush on her when you were a kid?”
Dean pulled a face, irritated by his brother’s attitude. “Not hurting anyone if I just say hi,” he muttered bitterly, “and I didn’t say you had to come with me.”
Sam seemed glad of that, at least, and decided to leave Dean to make an ass of himself alone. The gentleman at the desk was more than happy to provide the “agent” with the classroom he needed, and as Dean strolled down the corridor towards her class, his mind began to wander back to 1996, and his three months in Dawney, Montana.
It wasn’t that he hated school, he just didn’t see the point of it, not when there were more important things in the world, like hunting. His dad had left them in this crummy mountain town while he tracked something through the forest, and Dean didn’t know how long they were going to be there. Attending high school was at least a way to pass the time, and it kept social services off their backs, as well as providing a useful tool for keeping an eye on his troublesome younger brother.
Sam was happy to be starting school again. Summer had dragged, and they’d been at loggerheads in their small rented room, with little to do to occupy the time. Luther High School wasn’t a huge campus, and it had barely four hundred students, so Dean was relieved of the pressure of trying to make friends when he didn’t want to.
The first day back, and he’d already managed to irritate the science teacher and the coach. His third period was math, and when the teacher walked in, Dean wasn’t sure she was a teacher at all. She was young, maybe a few years older than him, and she looked nervous as hell as she addressed her only senior class of thirty.
“Okay, good afternoon, everyone,” she greeted, dropping her stacks of paper onto the desk. “Hope you’re not too bored of learning after the summer break already.”
A kid in the middle raised his hand, and she pointed at him, waiting for his question. “Are you really our teacher?” he snorted. “You don’t look much older than us.”
She chuckled, tugging her blouse back down where it had ridden up. “I am definitely your teacher. Well, I’m a student intern. I’ve got a degree, I’m just working towards certification now.” Picking up a piece of chalk, she turned to the board and wrote her name out in neat cursive before turning back. “I’m Miss. Y/L/N.”
Another hand went up but this kid didn’t wait for permission. “How old are you?”
Miss. Y/L/N smiled. “Now didn’t your mama tell you it’s rude to ask a lady her age?” she chided. “If you really need to know, I’m twenty-two. Don’t worry, I’m sure you’ll hate me as much as if I was fifty,” she joked, picking up a sheet. “Anyway, we’re here to learn math, so why don’t you open your books to page thirty-three and we’ll crack on with some calculus. You’re gonna have to bear with me - they told me I was teaching ninth and tenth, so I wasn’t exactly prepared.”
In any other situation, Dean was sure he would have gone out of his way to make this poor woman’s life hell. He wasn’t a model student, and never had any intention of being one, but for some reason, as he watched Miss. Y/L/N fluster over her notes, apologizing repeatedly for the slightest thing, he didn’t feel the urge to be his usual irritating self. Instead, he kept his head down - when he wasn’t looking at her - and worked quietly, though he was certain he was getting every answer wrong.
The class ended, and the other students rushed to get out and onto their last lesson of the day, but as Dean went for the door, Miss. Y/L/N stopped him. He froze when she called his name, suddenly panicked that she had caught him staring, but the gentle smile on her face didn’t scream “trouble”.
“Dean,” she said softly, “sorry, I didn’t want to pick on you in front of everyone.”
“Did I do something wrong?” he asked carefully, the ever present concern of social services in the back of his mind.
“No!” she insisted, laughing lightly. “I was told you were new here, and I wanted to make sure you didn’t have trouble following. These guys can pick up where they left off last year, but sometimes high schools don’t always follow the same plan, y’know?”
“Oh, uh,” he scratched his head nervously, “I’m fine, y’know. It’s math.”
A bright smile lit up her face, and his heart did a funny fluttering thing that left him slightly breathless. “That’s great,” she enthused. “If you have any problems, feel free to come to me, okay?”
He smiled back, struggling to contain the boyish crow that wanted to burst out of him at her attention. “Sure,” he replied through gritted teeth, “thanks.”
It didn’t feel like he could get out of there quick enough. His last period was a blur, passing by him as he sat at the back, unnoticed by the graying gentleman trying to teach them about ancient Europe. Miss. Y/L/N’s smile haunted his thoughts, and he couldn’t focus on anything, even when he met Sam at the school gate.
“Dean?”
His brother’s voice snapped him out of his stupor as they walked home. “What?” he mumbled, staring over at him cluelessly.
“Are you feeling okay?”
Dean shrugged. “Yeah, sure.”
“You weren’t paying attention to anything I just said.”
Another shrug. “Was it important?”
Sam scowled. “No, but -”
He groaned, picking up speed a little. “C’mon, man, I’m tired.”
There was a small hope that his newfound level of infatuation with the opposite sex was only a fleeting thing, but when Miss. Y/L/N walked into class the next day wearing tight fitting pants with a red blouse, he knew it wasn’t. He’d had plenty of experience with girls his age, and though she wasn’t much older, he wasn’t sure his experience would lend him any favors.
The worst part was wanting to please her. He actually paid attention, making an effort to understand the numbers instead of half-assing it like he’d done his entire life.
Confiding in Sam after school didn’t leave him with any more hope either.
“Dean, she’s a teacher.”
“She’s a student teacher.”
“I don’t think that matters much,” his brother denied. “Besides, aren’t we supposed to stay out of trouble? Social services aren’t gonna look the other way if you seduce a teacher.”
Dean grumbled unhappily. “I’m eighteen in a few months,” he complained.
“You really think we’ll be here then?” Sam asked, sadness in his voice. “We’ll be lucky if we’re still here for Halloween, Dean.”
“Guess I have to hope Dad comes to get us soon then,” he sighed.
John didn’t come back for them soon. He checked in every week, promising it wouldn’t be long, but weeks rolled into months, and Dean’s crush grew, developing into something his teenage heart wasn’t sure what to do with. Channeling his nervous energy into actually doing his work was landing him with good grades, and two months in, he brought home his first report card that didn’t include an “F”. Of course, only Sam was there to celebrate it, but he was a little proud of himself.
Two months into their tenure at Luther High, and one Wednesday after class, Miss. Y/L/N asked him to wait after class again. This period was the last of the day, so he didn’t rush, waiting until she’d cleared everyone out.
“I wanted to catch up,” she began, leaning against her desk and bracing her weight on her hands. “See how you were getting on.”
He shoved his hands into his pockets, giving her an awkward smile. “Good, I guess,” he mumbled, the same nerves from their last chat reaching up into his throat to strangle him. He coughed lightly, shrugging. “It’s nice here.”
“Hmm,” she agreed, glancing out of the window. “It is. Not somewhere I’d wanna live forever though. What about you?” He shrugged, and she smiled gently. “I’ve read your file, Dean. Are you an army kid or -”
“My dad travels for work,” he muttered, avoiding her gaze.
“Can I ask what he does?”
He tensed, keeping his mouth shut, retreating to the safe behavior of brick walling it. Despite that instinct, there was an urge, something inside him telling him that she wouldn’t laugh at him or call child services, and it was getting harder to ignore as she eyeballed him for an answer.
She stood straight, folding her arms across her chest. “You’re a smart kid, Dean. You’ve shown that in your grades, that even with all the disruption, you’ve got a brain in there. Have you… have you considered what happens after school?”
He shrugged again. “The family business.”
“What does that mean?”
His heart thudded in his chest. “My dad, he…” Don’t do it, his father’s voice instructed sternly in his head. It never ends well. He swallowed again, trying to turn his voice to steel, to put her off like he had so many others. “He’ll be coming to get us soon. You’re wasting your time.”
“I don’t think I am,” she replied, ignoring the warning in his voice. “I don’t consider trying to help anyone to be a waste of time. And I feel like you might need some help. Even just - even just to talk to someone. Without judgment.”
An unattractive snort escaped him. “They all say that, sweetheart,” he advised her, the cockiness seeping out of him, “but that disappears when they hear what I gotta say.”
“Try me.”
The solidity of her challenge gave him pause, and he finally met her gaze, holding it for a few seconds. Even though he was significantly taller, she made him feel small, like she was seeing through him, and he shuddered, letting the guard drop.
“I can’t,” he whispered. “You’ll call some social worker. I’ve been through this before, and I’m not putting Sammy through that again.”
Miss. Y/L/N frowned, dropping her hands to her sides. “Your brother is Sammy, right?” He nodded. “I’ve had him for a couple classes. He’s a smart kid,” she paused, smiling, “just like his brother.”
Dean watched her warily, feeling like prey on its back, belly exposed and vulnerable.
“The bonus of being a student teacher,” she continued, slowly walking to the door and closing it, “is I’m very good at missing things.” The lock clicked as she slid it into place, and she turned back to him. “Safe space, Dean. Whatever you need to get off your chest, I promise I won’t say a word to anyone.”
He stared at her, too terrified to move for a second. It wasn’t like his father was going to break the habit of a lifetime and build a life here, so telling her might not have many consequences, but then again, it was ingrained into him not to tell anyone about the family business.
Miss. Y/L/N waited, patiently, moving herself away from the door and back to her desk, giving him the space, and the exit, if he needed it.
“Do you believe in ghosts?” he finally asked softly, unwilling to meet her gaze just yet.
She shrugged. “I don’t not believe in them,” she replied. “I’ve never seen one myself.”
“And if I told you they are real? Like really real, and my dad kinda hunts them.” He rushed it out, still unable to look at her for fear of her reaction. “Other things too,” he whispered. “I’ve… I’ve seen things that… that give me nightmares.”
Her silence felt judgmental but when he eventually managed to look her in the eye, she was only staring at him with compassion. “That sounds terrifying,” she said quietly. “I can’t imagine anyone would sleep well with that knowledge.”
“Which is why I shouldn’t be telling you anything,” he growled, frustrated with himself. “Rule number one, don’t tell anyone what we do. And I went and broke it because -”
The abrupt end of his outburst made her frown. “Because?” she prompted, and he grunted, running a hand through his short hair. “Because?” she asked again, stepping closer.
“Because I like you,” he murmured, shoulders slumping in defeat. “Because you don’t look at me like I’m some kind of freak.” He turned away, embarrassed and ashamed, and ready to throw the towel in on the whole school thing.
Her hand touched his shoulder and he jumped, alert green eyes meeting hers in surprise. “I’m flattered,” she whispered, smiling gently. “And you’re not a freak. You’re a kid with a hell of a weight on his shoulders.”
It would have been lying to say he didn’t appreciate the validation. “I’m eighteen in January,” he muttered.
“Still illegal,” she chuckled. “Position of authority and all that.”
“I can assure you, I have no respect for authority,” he tried, turning on the charm, but it only made her giggle. The laughter didn’t hurt him, which was surprising, but he already knew he had no shot at her, legal or not.
“I’m not gonna pretend the thought of things being real isn’t terrifying,” she said slowly. “Obviously, I can’t relate. But I was seventeen not so long ago, and I remember how scary just regular life can be. You’re Sam's primary caregiver, right?”
“Uh-huh. When my dad’s not around, and -” He shrugged, trailing off, leaving the implication that his father wasn’t around much in the air.
“That’s a lot of responsibility at a young age. And Sam’s such a good kid, you should be proud.”
“I am.”
Miss. Y/L/N smiled, placing her hand on his shoulder again. “You’re a good person, Dean Winchester. Whatever you decide to do with your life, just don’t forget that, and I’ve got faith you’ll be okay.”
Two weeks later, Luther High School was in the rearview, and they were moving on.
She was every bit as beautiful as he remembered her. Standing outside her classroom, staring at her through the square window in the door, he felt seventeen again. Of course she’d aged, so had he, but for a woman pushing forty, she looked great.
Her class seemed focused on everything she was saying, and she seemed to be in her element at the front of the room, running through a mathematical problem on the board. Dean stepped closer, and the movement made her gaze dart to the door, her whole body freezing as she saw his face. Her lips stopped moving, eyes wide; the bell rang, saving her from her class noticing her sudden distraction, and she quickly dismissed them.
He waited outside the door until the room was empty, then stepped in, closing the door behind him. Miss. Y/L/N - he noted her name on the board, internally crowing that she was not married - smiled, folding her arms across her chest as she watched him approach.
“Dean Winchester,” she breathed. “That smart kid I always wondered about.”
“Miss. Y/L/N,” he greeted. “Best teacher I ever had. Can’t believe you recognized me.”
Her smile widened. “How could I forget a face that handsome?” she chuckled. “And it’s Y/N, please, we’re both grown ups now.” She looked him up and down, not even bothering to conceal her appreciation. “Never thought I’d see you again.”
“You’re still teaching,” he commented, looking around.
“I am. What about you?”
“Family business,” he murmured hesitantly, unsure if she’d remember. “Guess I never found another path I liked enough.”
She hummed. “Are you happy though?” she asked curiously.
“Yeah,” he nodded, “for the most part. Yeah.” His awkwardness was showing like twenty years had never passed, and he smiled, shoving one hand into his pocket. “What about you? Husband, kids?”
“Hmmm,” she mused. “Two cats and a ridiculous amount of books about monsters,” she confessed after a second or two, and he blinked at her in confusion. “Guess I couldn’t quite drop the questions after what you told me. Only reading though, I don’t ever want to meet one in person.” Her face contorted in horror. “Oh, god, that’s why you’re here, isn’t it? The attacks - is it a monster?”
He pulled a face. “Not sure yet. My brother and I are looking into it -”
“Wait, your brother, Sam?”
“Yeah.”
“You weren’t kidding about family business,” she muttered.
“I take it you didn’t see or hear anything?”
She shook her head. “I’m afraid not. I don’t stay past dark, and I only teach the juniors now. You’d be better off talking to Mr. Harrison, several of his students were involved.” A knock at the door made them both turn, and Dean waved at Sam on the other side. “Is that Sam?” she asked, sounding a little shocked. “Wow. He got tall.”
Dean chuckled. “Yeah, he did.” He looked back at her, a smirk on his lips. “Listen, when we’ve dealt with this,” he began slowly, “I’d really like to buy you dinner. I don’t think I gotta worry about getting you in trouble now we’re both graying adults.”
Her laughter was music to his ears, and she turned to her desk, bending to scribble her number on a scrap of paper. Dean took the opportunity to admire her ass in the tight-fitting black pants, and his cock reacted at the thought of finally getting what his teenage fantasies had been made of.
She straightened and slipped the scrap of paper into his hand, closing his fingers around it. “I’m certain we can still find plenty of trouble to get into,” she purred, the sudden seduction making him flustered as Sam knocked on the door again.
“I bet we can,” he stuttered out, backing up towards the door. “I’ll call you, Miss….” He laughed nervously as he corrected himself. “Y/N.”
It hadn’t taken more than another few hours to figure out the case was vampires, and Mr. Harrison was actually the creature in question. He’d been turned on a wild weekend and had decided to attempt sustainable feeding, using his young students as walking blood bags. Unfortunately, the light snacks weren’t enough to keep him going, and it was only by the grace of Sam and Dean’s presence that the final victim wasn’t a casualty.
Dean was nervous to call her when they were finally done hunting the vamp down and when he finally dialed the number, he was half-expecting it to be fake. She answered after four rings, and he stumbled over his words as he asked her if she was still interested in dinner. Her answer was a resounding yes, and he let her take the lead on a place and time.
“You’re going on a date?” Sam asked, disbelief in his voice.
“Yeah, I’m going on a date,” Dean snapped, buttoning up his nicest shirt, one of his newer red plaid button downs. “One, I haven’t had sex in months, and two, she’s literally my teenage fantasy.” He paused, tossing his brother a dirty look. “Three, maybe you should consider getting laid.”
Sam sneered at him, then threw himself on the bed, switching the tv on. “I guess I’ll stay here then.”
“You do that,” Dean grinned, grabbing his jacket. “Don’t wait up.”
She was waiting for him in a little Italian place downtown, and it was all he could do not to grin like an idiot when he walked in and saw her. Her smile was bright as he sat down opposite her, both of them remaining silent as the server handed them each a menu.
“Hi,” she whispered, leaning in. “You look really good.”
Dean let his gaze drop, admiring the view of her cleavage in the little black dress she’d paired with leggings. “Hi yourself,” he murmured, smirking lightly. “That’s a very distracting dress.”
“Would you have preferred I wore a pantsuit?” she teased, giggling when his cheeks turned red. “This place is great, any of their pasta is amazing.”
“You eat here often?”
She nodded, smiling at him again. “It’s my favorite place.”
He didn’t know what it had been about her all those years ago, but she was the same now, coaxing him into an easy conversation. They talked about everything from her life to snippets of his, though she avoided asking about anything too intense, and he avoided sharing anything too disturbing. It was nice for once to just be a regular person, without the need to be incredibly guarded about his secrets.
Dinner moved onto dessert, and they kept talking, flirting with each other as the restaurant emptied around them. By the time their meal was finished, Dean had begun to envision what happened after, but when it came to propositioning it, he found himself unusually nervous.
She called for the check and insisted on paying, so he didn’t argue, sitting nervously as she thanked and tipped the server. When they disappeared again, leaving them alone, she turned her attention to him, smiling almost coyly.
“I’m not gonna pretend this is anything more than what it is,” she said suddenly, keeping her voice even and quiet. “One night between two adults, who they’ll probably never see again, right?”
He sighed with a tiny laugh, leaning his arm on the table. “I’m not the type to settle down,” he replied calmly. “And this life…”
“I get it,” she whispered, taking his hand. “I’m not looking for long haul. But I wouldn’t mind making a happy memory or two.” Her lips twitched into a smile. “Besides, I don’t wanna have gotten all dressed up for nothing.”
“I can assure you,” he replied firmly, “you did not.”
She grinned. “My place is about four blocks away.”
“My car’s outside.”
His inner seventeen year old, if such a thing existed, was jumping for joy as she led him out of the restaurant. She admired his car openly, prompting him to act out just a little, showing off his baby with pride before driving them back to her apartment. The aforementioned cats were meowing loudly when they entered, and he followed her into the kitchen, shedding his jacket as she fed the whining felines.
“Sorry,” she said breathlessly, returning to him once she’d washed her hands.
He smirked, bypassing conversation as he slid his fingers along her jaw and into her hair, pulling her into a passionate kiss that made her sigh when he pulled away a few seconds later. “Wow,” he murmured, staying close, noses tip to tip. “You know how many times I dreamed about doing that?”
“Did you ever dream about being in my bedroom?” she teased, twisting her finger in the collar of his shirt.
“Actually, most of the time, I was thinking about bending you over your desk,” he grinned, sliding his other hand over her hip. “I’m guessing you don’t have one in here?”
“No,” she giggled. “Will the bed do?”
“Lead the way.”
Her shoes were abandoned by the time they reached the bedroom door, with his shoes following just inside. Pants, shirt, and dress landed in another pile, and as they hit the bed, her leggings disappeared, his t-shirt following in rapid succession. His hands were everywhere he could put them, lips kissing every patch of skin revealed unless he was preoccupied by her mouth, and she whimpered when his fingers deftly unhooked and discarded her bra.
If only seventeen-year-old him had known this would happen one day.
Finally, he broke away to catch his breath, chuckling when he noticed her breathing heavily too. “If this had been ten years ago,” he mumbled, shaking his head.
“Tell me about it,” she agreed, reaching for the drawer beside her bed, opening it and pulling out a box of condoms. He happily took one but didn’t open it, flashing a grin at her. “What?” she asked.
“You’re rushing me,” he chided softly. “I have no intention of doing anything but savoring this moment.”
Any reply she had to that disappeared as his fingers slipped under the waistband of her panties, finding her already wet. Her moan drowned out his, and she clutched his shoulder as he eased a single finger into her, thrusting it back and forth to coax more wetness out of her.
“Oh, fuck,” she whined, arching a little, hips canting toward him in an effort to get more friction. “Oh, fuck, Dean -”
“You’re so wet,” he groaned, “can’t wait to have this pussy wrapped around me.” Her fingers tightened on his shoulder as he added a second, opening her up. “But I want you to cum first.”
It was pointless trying to quiet her own noises, giving up when biting her lip didn’t cut it. Dean worked her higher and higher, watching her facial expression crumble as she reached her peak, her cries turning silent when he twisted his hand and grazed his thumb against her clit.
“I really wanna eat you out,” he murmured, lowering his voice to a rumble, and she quickly nodded, giving him the permission he was seeking. Withdrawing his hand, he left her teetering on the precipice of an orgasm as he removed her panties and slotted himself between her thighs.
His tongue was warm against her sensitive sex and she cried out again as he explored her, figuring out what made her tremble. She was drowning in a haze of arousal, unable to think about anything beyond his mouth on her cunt, and when he sank two fingers into her again, she had to fight the urge to close her thighs against the pleasure.
Dean was in heaven, working her into a frenzy with his tongue and fingers. He’d had a lot of time to think about this particular fantasy, and having her here, wet and warm and inviting, writhing underneath him, he was certain he’d peaked. He knew he would be replaying this one on repeat forever.
“Deeean,” Y/N whimpered, fingers tugging on his short hair. “Fuck, I’m so close -”
He broke away, working his fingers into her harder as she spread herself open a little more. “Don’t worry,” he growled, “just let go, baby.”
Her cries echoed off the walls when he sucked her clit into his mouth, teasing the bud and crooking his fingers inside her to find that extra sweet spot. It didn’t take long; she wailed as her pussy clenched around him, her pleasure ringing in his ears, but he didn’t stop, working her through the climax until she went limp.
He couldn’t keep the filthy smirk off of his face as he got onto his knees and retrieved the condom from where he’d dropped it. “You doing okay there, Miss. Y/L/N.”
“Don’t,” she panted with a giggle. “You’ll make it awkward when people call me that.”
“Spoilsport,” he chuckled, opening the foil packet and tugging the condom free. “You still want this?”
She pushed herself up on shaking arms. “Uh-huh.”
A few seconds later and the condom was on. He stroked himself a few times before leaning down to capture her lips in a kiss, guiding the tip of his cock through her folds until she whimpered into his mouth. Her pussy was dripping, eagerly accepting every inch as he sank inside her, drawing back a couple of times when he met resistance, but not stopping until he was buried deep.
He had to stop then, feeling how hard his heart was racing. She caught his jaw with her hand, kissing him softly, lifting her right leg to press her knee against his side, allowing him to slip a tiny bit deeper. “Dreams do come true,” he murmured, brushing his nose against hers.
“You always were hot for teacher,” she joked, and he chuckled, kissing her hard again before starting to rock against her. He didn’t rush, enjoying every thrust, relishing the way her body drew him back in, keeping him close. She didn’t seem to mind that he wasn’t in a hurry, letting him push her into an easy orgasm. His hands wandered, toying with her tits when he was going slower, grabbing her hips when he got faster, a little more urgent.
“Want you to cum again,” he growled, holding her leg in place as he fucked into her, “Wanna feel it right around my dick.”
“Uh-huh,” she managed, clinging to his neck. “Wanna feel y-you too.”
He nodded then kissed her, focusing on nothing but how good she felt in his arms, underneath, around him. So soft and wet, warm, inviting, his literal dream come true. Even if this was only one night, he knew he’d never forget her.
“Fuck,” she gasped. “Dean -”
Her whole body quivered, thighs clenching around him as her pussy tightened, and he couldn’t hold it off, reacting with his own climax. His vision swam, and he couldn’t think beyond her warmth, her taste, her moans as she came for him. She clung to him until they were both done, collapsing with him onto the bed. Breathlessly, he kissed her one last time, withdrawing reluctantly to lay beside her.
“Holy shit,” she groaned, flinging an arm over her eyes. “I’m not gonna lie… the bar was low. You obliterated it.”
Dean chuckled, folding his hands behind his head, allowing the swell of pride in his chest. “That - that was awesome,” he agreed. “A dream come true. Literally.”
Y/N yawned, reaching over to place a hand against his chest. “I hope you’re not expecting a round two.”
He grinned. “Maybe in the morning.”
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