Pairing: Professor!Dean Winchester x (Plus-Size) Grad Student!Reader
Summary: Forbidden fruit. Dean knew there was always a consequence for the taking and sampling part. The question was — is it worth how good it tastes? Remembering the feeling of your soft curves under his hands, the look in your eyes, and the temptation of your lips, he had a feeling it would be more than worth it.
AN: Happy fall! Class is in session, and it's the perfect time for some more Professor Dean. 😉
Here's the sequel series to continue this one-shot, 10 'Til Midnight. ⋆˙⟡
Series Tags & Warnings: 18+ only. Office politics, history, mythology, literature, Shakespeare, mutual pining, sexual tension, sexual fantasizing, smut, accidental drug use (you'll see lol), protective Dean, and more chapter-specific tags.
♬.ᐟ Listen while you read:
Playlist Poster || YouTube || Spotify
Chapters:
Chapter titles inspired by a line of Shakespeare.
Prologue - 10 'Til Midnight | Podfic version!
Part 1 - To This Great Stage of Fools
Part 2 - For a Charm of Powerful Trouble
Part 3 - Not With the Eyes, but With the Mind
Part 4 - In the Office & Affairs of Love
Part 5 - A Madness Most Discreet
Part 6 - The Law of Friendship (Bids Me to Conceal)
Part 7 - Speak Low, if You Speak Love
Part 8 - If Thou Hast Me at the Worst...
Part 9 - Hear My Soul Speak
ᝰ.🖋️ Series complete!
🎙️ Listen to a podfic version of the Prologue - 10 'Til Midnight:
⋆˙⟡ Tag Lists || Fic Library Blog ->
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Here is my art for Mydestielbabies_67′s BottomCas Big Bang fic “Turn On A Dime”!
I know the art doesn’t really give the content of the fic away at all (though Claire attacking Dean with a frying pan delights me. A little bit of threatening of your father’s new boyfriend is allowed.)
Square/s Filled: Professor AU - @spnaubingo / Office Sex @spnkinkbingo
Rating: Explicit
Pairing: Professor!Dean x Female!Professor!Reader
Word count: 3,679
Summary: Bobby is retiring from the Head of Department and sourcing a suitable candidate for the position. Dean and Y/N are each other's main competition, but the fight for the job leads to an unexpected but satisfying outcome.
Warnings: Swearing, mild angst, enemies to lovers, smut: dirty talk, oral sex (female receiving), Dom!Reader, Sub!Dean, mild choking, unprotected sex (wrap it up people)
A/N: I'm slowly getting back in the swing of things, so thank you to everyone for your patience. As always, happy reading and enjoy! Beta’d by my love @downanddirtydean.
The loud ambience of chatter, cutlery scraping against plates and laughter in the restaurant was a welcomed distraction. Y/N swished the last sip of wine in her glass around, her mind drowning out the people at the table that talked around her. It was her third glass, and she was contemplating whether she should order a fourth or go home, but she knew that she couldn’t leave just yet. Considering it was a history department dinner and the head professor, Robert Singer (or Bobby as he preferred to be called by colleagues) was retiring soon, she had to stay. More than that, she still needed a chance to make an impression to be considered for the head of the department, which was being squashed by her main rival at that very moment.
She glanced to her left, eyeing Dean Winchester as he sipped his beer and sat with Bobby. He threw his head back as he guffawed, his perfect teeth on full display and quite frankly she wasn’t sure what she wanted to do more: stab him with her fork repeatedly or ride him on that ugly plaid couch he had in his office. No matter how much she hated him and the fact that he got picked for everything, she couldn’t deny he was incredibly sexy.
“Bobby, you know if you were to trust me with this…” her ears perked up as she heard his deep, husky timbre across the table, tuning out all the other voices in the room as she focused on his, “I’m gonna do my fucking best to keep the department running the way you’ve been. We’ve known each other a long time…”
She scoffed, shaking her head as she brought her wine glass to her lips, and took the last sip in one gulp. She had known Bobby two years longer than Dean but if he was going to play that card, then she could play it better.
“Okay, let’s leave it there for today,” Dean announced, glancing at his watch. “Remember you’ve got a week left until presentations so no excuses about more time…”
A few students nodded as others groaned while they packed their belongings and started filing out of the lecture room. Dean wiped all the notes off the whiteboard as the projector screen buzzed, closing slowly. He took a few moments to shove his papers and books into his leather satchel, but a familiar laugh reached his ears causing him to pause what he was doing.
“Hey, Dean, can I talk to you about something?” Luke, his TA asked as he approached him.
“Yeah, sure…” Dean replied, distracted by trying to look out the door.
Luke blabbered about something, and he tried to give the kid his full attention, but when he spotted Y/N over his shoulder, walking into the room with Bobby by her side, both chuckling about who the hell knew what, he felt knots in his stomach. He glared at her, trying not to think about what she’d look like on her knees or even above him, and focus on the rage he felt towards her. She was just far too charismatic and everyone in the department loved her. When he got the job at the university 6 years ago, she had already been there for two, and all he ever heard was how great she was at her job and how she had set the bar extremely high for such a young person. After that he had made it his mission to reach an even higher one.
“Dean? You okay, man?” Luke asked, snapping Dean out of his thoughts.
“Y-Yeah, y-yes,” he stuttered, clearing his throat. “That all sounds great, so you’re good to go.”
“Okay,” Luke mumbled, frowning at him as he secured his backpack over his shoulder. “See you tomorrow.”
Dean sauntered across the room as Luke left, stopping in front of Bobby and Y/N, a forced smirk gracing his features. “What’s going on?”
Y/N sighed as her laugh subsided, turning to him. “Well, Bobby’s daughter is trying to get into fashion merchandising so I was just telling him how I have a cousin that works in fashion and could help her out.”
“Really?” Dean asked, his eyebrow raised in suspicion.
“Sure did,” Bobby replied, smiling at her before he turned to Dean. “This one’s incredible, even offered to have us over for dinner as a family. I know it’s not exactly professional, but hey, I’m retirin’ soon, so why the hell not?”
Dean huffed a laugh, nodding slowly. “Sounds awesome.”
“Alright, I better get set up for my class,” she stated, taking her oversized purse off her shoulder, smiling softly at Bobby. “I’ll see you around.”
Dean gave Bobby a tap on the shoulder as the older man walked away, before he followed behind Y/N. He watched as she set things out on the desk at the front of the room, making sure all her papers were evenly spread out with books open to the appropriate chapters, in line with everything else.
“What are you up to, Y/N?” he questioned, his eyes scrutinizing her every move.
“Right now? Getting ready to teach my class,” she answered, simply.
“Yeah, that’s real cute, I meant what are you up to with Bobby,” he snapped, his jaw clenching as he stared down at her.
“Nothing that you weren’t already doing at dinner the other night,” she countered, lifting an eyebrow as she looked up at him. “You pulled the “known each other a long time” shtick so I pulled the “known him longer” one.”
He bit down on his lip as he considered what she said. “You don’t want this job, Y/N. There’s a lotta pressure-”
“Which I can handle a hell of a lot better than you,” she stated, a confident smirk pulling at her lips. “I think you’re just afraid of how hard I’m gonna ride you when I’m in charge.” Her words got the reaction she had been hoping for, feeling her insides leap with pride at the way he gulped, his eyes widened slightly before he sobered, clearing his throat.
“You’re not gonna win, Y/L/N,” he muttered under his breath as he leaned in close to her, conscious that they were no longer alone as students began to walk into the lecture hall.
She scoffed, glaring up at him. “I wasn’t aware this was a contest, Winchester.”
“Oh, it’s always a contest with you, sweetheart,” he stated, smirking.
“Care to make it interesting, then?” she asked, folding her arms across her chest.
“Why not?” he shrugged. “If I get the job, you can’t complain about any of the decisions I make and…” he grinned, his green eyes boring into hers, “you have to buy me a drink every Friday at the bar across the street.”
She breathed in deeply, keeping herself calm as she nodded slowly. “Well, if I get the job, then you can’t complain about me being in charge either and… not just at work.”
He groaned softly, covering it up with a cough as he stepped back from her. “You’re on.”
Y/N’s eyes didn’t leave him as he turned and walked away, leaving the room with his shoulders tense. She smiled to herself as she saw her students coming in and taking their seats. No matter how much Dean got on her nerves, she had to admit that it was a lot of fun messing with him. She didn’t really care for holding up her end of the deal, but she did want the position of department head. She had been there 8 years and had worked hard every single day. Everything she had achieved was leading to this moment, and she wasn’t about to let Dean ruin that.
She just had to do it all her way.
The last few weeks of Bobby’s tenure passed by in a whirlwind. As he was the last of the old professors to retire and the department was now full of people much younger than him, it was up to him to choose between Dean and Y/N to lead the others, as they had been at the university the longest after him. While he cared about both of them, he knew had a decision to make and it was hard when he didn’t want to hurt anyone in the process.
Y/N went about that time as usually did, keeping her head down and doing her job. She had no interest in fighting fire with fire like she had that day when she and Dean made that deal. She had never been good at doing that, and much preferred for Bobby to choose her because of her work ethic. Though Dean certainly didn’t need to know that she was done playing mind games, because she did enjoy watching him squirm. She hadn’t seen him very often in the past few weeks, only glimpses of his retreating stature at the end of hallways or leaving the lecture room that she used after him on Wednesdays.
On a sunny Friday afternoon, Y/N and Dean finally came face-to-face after weeks outside of Bobby’s office. They walked in and took the two seats across from the desk, both looking around the room at the boxes full of papers and a few boxes of books, the rest left on the shelves for the next department head to use.
“So, I figured I’d call you both in here,” Bobby started as he sat down on his chair behind the desk, “and tell you what the final decision is.”
“Alright, lay it on us, Bobby,” Dean stated, a small chuckle escaping him.
“Well, it was a hard choice because you’re great at what you do… but Y/N,” the older man looked towards her, “This office is officially yours.”
“Oh my god! Are you serious?” she exclaimed as she stood up from her chair, an elated giggle falling from her lips. She rushed over to Bobby, hugging him tightly. “Oh wow, thank you, Bobby. Thank you so much…”
Dean pulled his lip between his teeth, gnawing at the skin as he gripped the arms of the chair he sat on. In some way, he was relieved. He had been right, it was a stressful job and it took a lot of work, so maybe it was a good thing he escaped that pressure. That didn’t mean it didn’t hurt. Slowly, he stood up from his seat, slapped on a supportive smile and held his hand out to Y/N.
“Congrats, Y/L/N,” he muttered, his smile faltering.
Y/N felt a pang in her heart as she looked up at him, her mouth pulling up slightly to accept his kindness. “Thanks, Winchester.”
“Okay,” he slapped his hands together, his eyes scanning the room, looking anywhere but at her. “I gotta go grade papers, so I’ll see you around.”
Y/N watched him leave, her face settling into a deep frown. He was great at what he did, and he deserved to at least be reassured of that. She and Bobby talked about a few changes before she left his office, stalking down the hallway as she glanced at her watch. She had quite a bit of time before her next class and she wanted to speak to the green-eyed professor, who no matter how much he frustrated her, she cared that he wasn’t beating himself up about this. She reached his door, the gold plaque displaying his name and majors underneath, and knocked swiftly. She heard his gruff “come in” and opened his door, shutting it behind her once she stepped in.
His office was warm, the desk close to the back of the room in front of the bookshelves, with the awful red, white and black plaid couch against the side wall, a brown leather armchair in front of the desk the only seat other than sofa and his own, but she chose to stand.
“Let me guess…” he started, staring up at her as he tapped his red pen against the papers in front of him, “you’re here to rub it in my face-”
“No,” she said calmly as she cut him off. “That’s the last thing I want to do.”
He scoffed. “Okay, sure.”
“Dean,” she sighed, shaking her head as her gaze softened. “You’re great at your job, and we both know that. I may be the head of the department officially, but I want your input, too. I want us to work together.”
He sat back in his chair, his green orbs observing her. “Really?”
“Really,” she confirmed, offering him a small smile.
“So… no tricks? You’re not playing me like you have been this whole time?” he asked, still doubtful of her sentiments.
“I haven’t been playing you these past few weeks, and I’m certainly not now,” she replied, firmly. “I think… I think we could work well together. You know, when we’re not goading each other.”
He huffed; his eyebrows raised as he nodded. Their eyes met across the desk as he contemplated her offer in silence. A small smirk grew across his lips. “Okay.” He stood up and walked around the desk, stopping in front of her, their bodies close. “You know, I’m not gonna make it easy on you.”
She bit her lip to keep from smiling. “Well, I do have authority over you, there might just be consequences if you act up.”
He hummed, nodding slowly in understanding. “Not sure I can get on board with that.”
Shifting closer to him, her hand slowly slid up his sweater and curled around his tie. She tugged on it hard, a soft groan leaving him as their faces were inches away from each other, their eyes locked. She had a mischievous glint in hers as her lips brushed against his.
“You don’t have a choice.”
Y/N pushed herself up on the toes of her heeled boots, pressing her lips to his in a searing kiss. Dean’s arms draped around her waist as he pulled her close, her hands groping at the grey sweater he wore. Their mouths separated long enough for her to remove it, pulling it off him and throwing it behind her. She loosened the tie but left it on him, her fingers hurriedly unbuttoning the white shirt he had on. It soon joined the sweater on the floor, as she grabbed him by his tie and turned around, pushing herself up to sit on his desk. They kissed roughly, both fighting for dominance as his hands slipped up her knees covered by her sheer stockings, finding the warmth of her upper thighs as he pushed her black skirt up around her hips. His plump lips trailed down her jaw and her neck, nipping at her collarbone and he tugged on her panties harshly, the lace giving way with a loud tear.
She pulled away from the kiss, a gravelly laugh falling from her lips as she pulled him by his tie. “On your knees.”
He showed her a glimpse of defiance, a cocky smirk on his face, but she gripped his shoulder tight in her other hand, a groan escaping him as he bent down between her legs. She spread them wider, a brazen grin on her lips as she led him closer to her heat with his tie. His head moved between her thighs, his tongue licking a long stripe against her folds, causing her to moan softly at the action just as he did at the taste of her. His skilled muscle circled her clit just as her hand gripped his short locks and held him in place, throwing her head back as she continued the motion repeatedly.
“So good,” she moaned, hooking her leg over his shoulder, her heel digging into his back. “Fuck, you’re so good at that.”
He continued his ministrations but alternated between paying attention to the swollen nub and running his tongue along her folds, teasing her tight canal, getting her wetter than she already was. He growled as he shifted closer to her, the sound sending vibrations through her and causing her to hold him tighter, refusing to let him move.
“Oh fuck, just like that,” she purred, biting down on her lip. “God, you’re fucking amazing…”
A soft whimper left him as he continued to work her over, his actions gaining vigour. She giggled to herself as she realized her words of praise were bringing that side out in him.
"You like hearing me say you’re good, Dean?” she asked even though he couldn’t answer, but she didn’t need one to know the truth. “You like being good?”
His green eyes glanced up at her, a thrill running through her as she saw the effect of her words on him through his gaze. She moved her leg away from his back, slowly shifting away to pull him up from the floor, their faces close once more. She leaned in and kissed him feverishly, moaning at the taste of herself on his lips and tongue. Her hand drifted down, sliding over the crotch of his trousers, feeling his bulge through the fabric, no doubt a result of what he had done with his skilled mouth. She made quick work of undoing his pants, letting him kick off his loafers and remove the trousers, joining the pile of his other clothes.
Y/N wrapped her hand around his hard shaft, pumping him back and forth, her pace slow and torturous as she looked up at his face, his features etched with pleasure as his eyes fluttered closed, his jaw clenching. He groaned loudly as she picked up the pace, dropping her saliva along his length, and continued to stroke him.
“Take a seat, lover,” she whispered, beaming up at him as she shoved him lightly towards the couch.
Dean dropped down on the sofa, his eyes never leaving her as she pushed off the desk, unbuttoning her red blouse and pulling it out from her skirt. She dropped it on the floor, leaving her in her dark red lace bra, skirt and boots. She sauntered over to him, straddling his lap and she took his tie in her hands, pulling him towards her. He stared up at her as she reached down and took hold of his dick, lining it up to her entrance. They kept their gaze locked on each other as she sank down on him, his neck straining back as she sat on his lap, his shaft completely sheathed by her walls. She moaned loudly, not caring that anyone walking past outside might hear her.
“Oh fuck,” he groaned, leaning back against the couch. “Fuck, sweetheart, you feel so damn perfect…”
She gripped the tie harder and pulled him close again, just as she started to rock against him. They both moaned at the sensation of his cock moving in and out of her, her walls clenching around him with each thrust of her hips. He lifted his to meet them, their bodies rutting against each other as she picked up the pace.
“So fucking good, love feeling you deep inside me,” she whimpered, her hand cupping his face as their eyes never left each other’s. “Feels so good, you’re so good to me, Dean… so good for me…”
“Y/N,” he grunted, his jaw tight as he looked up at her.
She looped the tie around his neck, pulling the end as she refused to let him remove his intense gaze from her. The tie pressed tight against his windpipe, a strangled moan leaving him as his eyes shut tightly. He was completely overwhelmed by everything she was making him feel, and he was more in awe of her now than he ever had been.
“Such a good boy for me,” she praised, smirking down at him. “Treat me so well, your cock fills me so good, baby, makes me feel so full… wanna feel you cum inside me.”
Her thrusts picked up momentum, her hips snapping against his as she rocked harder in his lap. Her walls contracted around his dick as he thrusted into her, moving deep within her and pushing her closer and closer to the edge. She pulled harder on the tie, his eyes rolling back as he growled, a wicked chuckle leaving her at the animalistic way his hands gripped her hips, pulling her down harder against him. She leaned down and kissed him hard on the mouth, the coil within her pulling harshly, ready to snap at any moment.
It was sudden, like a tidal wave crashing against the shore, but she bit down on his lip as her release washed over her, a gasping moan vibrating against his mouth as her wetness covered his shaft. He felt his cock throb as her walls contracted around him, his hands clenching into her thighs as he groaned weakly against her lips, spurts of his seed spilling deep inside her.
“Fuck,” she laughed breathlessly, her chest heaving as she pulled back from him.
Y/N removed the tie from around his neck, hissing at the red wilts circling around his flesh. She leaned in, pressing soft kisses along the tender skin. He pulled her close, resting his head against her cheek, breathing heavily as he came down from his high.
“If this is gonna be the consequences… of me acting up… we don’t have a problem,” he huffed out between harsh breaths.
She giggled, kissing his forehead. “Good to know.”
“Don’t you have class?” he asked, tilting his head back to look at her.
“Not for another twenty minutes,” she replied, stroking her thumb along his jaw.
“Any more consequences I should know about?” he smirked.
Her hand slid down his neck, her thumb applying a light pressure and causing a small grunt to leave him. She bit her lip, smiling down at him. This was definitely a new aspect to their working relationship, but she couldn’t wait to see where it took them.
“Plenty more.”
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Summary: Online school sucks but your professor is worth the torture.
Warnings: 18+, smut, unprotected sex (wrap it before you tap it kiddos), oral sex (male receiving), office sex, desk sex, sex from behind, biting, hair pulling, a hint of choking, professor Dean Winchester (yes, it’s a warning), student-professor romance and so on.
A/N: This one was inspired by “Pay Attention” written by my dear, lovely friend @winchest09 who also happened to be my beta once again and one of the best people I know. Thank you honey! <3
A/N: @talesmaniac89 once again, thank you for those amazing dividers! <3 Guys, go check her stuff, she’s a talented devil!
Lockdown sucked. Since the very beginning you knew it'd be a pain in the ass. Stay away from people, sit at home, wear a mask. Dammit. So many plans went to hell; your photography classes, your friends birthday party, visiting your parents in your family town. You knew it was safer like that but hell, you hated it. Your own apartment seemed to be getting smaller and even the flower on your window sill became annoying. Not to mention your online classes; sure, you didn’t have to get ready and drive almost half an hour to get to the Uni but sitting in front of your laptop had started to get on your nerves.
Your eyes were heavy and red after hours of looking at the screen, your body yelled to be stretched and you wanted to scream every time your internet lost connection. Headache became your best friend, so did coffee. You were pretty sure your addiction just deepened and instead of blood, there was caffeine in your veins.
You yawned and rubbed your eyes as you were sitting in on the first period of your last classes. The whole day on the same chair, you were sure you used every possible sitting position to try and remain comfortable. Glancing at the clock you growled; it’s been almost 10 hours.
How long can one day be?
Thankfully this subject was one of your favorites. And it wasn't because of the handsome man in white shirt who helped in enjoying the last two hours of this nightmare; at least that's what you've been telling yourself.
You like the subject, Y/N.
You smirked seeing how he brushed his longer than always hair with those beautiful hands; forearms exposed and tempting because of the sleeves being rolled up. His stubble was more visible due to quarantine and he just simply got hotter; you honestly thought it wasn’t possible. But there he was, behind his desk in a soft light; black watch on his wrist as usual, ring on one of those long fingers. Knuckles, little bones and veins, all making you lick your lips. This sharp jawline you dreamed to kiss, eyes so green that you could drown in them even through the screen. Arms hidden under the shirt that gave him a more casual, domestic look which made him even more attractive. You bit your lip seeing a gorgeous smile spreading on his face as one of his students said something funny.
Those teeth; incredibly white and sharp… the way they could sink in your flesh, leaving marks all over your body as his hands travelled up and down, raising up your temperature.
The things you could do with this man… The thought itself was bad but you couldn’t stop daydreaming about your professor. He was too tempting, too beautiful to hold back your imagination. You didn’t remember most of what he said during any classes, too mesmerised by him and even though his deep, smooth voice was so listenable, you weren’t able to focus. You caught yourself staring at him or closing eyes just to feel those vibrations running over your skin.
You missed sitting in class on his lectures. There was a reason why you chose the first row and it obviously wasn’t your ambition to learn more.
“Okay guys,” Dean started when you stretched. “I think we can take a break now. In the next meeting we’ll finish this Unit and I’ll let you free earlier. Um… so let’s make it twenty minutes and I will send you an invitation. Just don’t drink yet, I know it’s friday evening but I want you all sober just a little bit longer,” he joked and you smiled seeing few people laughing on muted.
Then he simply said “see you” and ended the meeting. You stretched again, taking a deep breath and stood up. Before leaving your room you opened the window to let in some fresh, evening air and then went to the kitchen. Filling cups with some sugar and tea bags, you waited for water to be boiled.
Leaning against the counter, you focused on the wall in front of you. The pictures hanging there were way too old and there were some stains marking the paper. This lockdown made you crazy; you already painted your bedroom and the office, and you made some renovation in the bathroom. All in all, you spent more money without walking out of home. Ridiculous.
You jumped a little, detached from your thoughts by the whistling kettle and soon your tea was ready. Humming some random melody, you turned off the light with your elbow and headed towards the office room. Using your elbow again you opened the door and smiled.
"Hey there, professor," you put one cup down on the desk. "How's your class going?"
He turned around on his chair and flashed you this charming smile. You were smiling at yourself from his laptop wallpaper; he took this photo almost a half year ago in his apartment, just two flats above your head. You still could feel the softness of his white sheets you had been tangled in on this picture.
"All fine," he took a small sip and frowned. "Just… one of my students seems to be off today."
"Oh, really? How?" You asked, leaning against a desk. He played with the cup, shrugging, visibly holding back a smile.
"She stares blankly, lost in her thoughts. She's not answering any questions willingly, she seems to be away." He acted like he was talking about some random girl.
You felt his knuckles briefly touching your naked thigh; it was way too warm indoors to wear something else than shorts. The delicate movement tickled you and your legs jerked uncontrollably. You looked at him, deep in the eyes and suddenly the air thickened. The tension between you two shot up; his intense gaze pierced into you like a sword, forest green eyes making your breath lose its track.
"Hmm, maybe it's your fault," you managed to suggest, putting down your cup. His eyebrows raised along with mouth corners.
"My fault?"
Now both his hands gripped your legs and sharply pulled you closer to him. You sifted his fluffy hair between your fingers and scratched the back of his head. He hummed in response closing his eyes as his palms sneaked under your shirt, making you shiver a little.
"You can be very distracting, Mr. Winchester," you purred standing between his legs.
Dean was looking up at you with sparks in his eyes and dimples caused by a pert smirk. Your shirt suddenly lifted up, exposing your stomach that he gladly kissed. Slowly and wet, using his tongue first, squeezing your hips at the same time. Hot, soft lips pressed to your skin, slightly sucking, heated breath fanning over your flesh, causing the ocean of goosebumps. You felt your insides tremble at the feeling. Closing your eyes you let yourself enjoy him; his strong hands now caressing your back, mouth placing open kisses across your belly and going up.
He knew how to build you up, how to turn you on. You swallowed hard and gasped when he licked your nipples; you didn’t bother to wear a bra at home. He smiled against you and backed away; you immediately looked down and kissed him. Deep and hard, cupping his cheeks, pushing on him so he leaned back on the chair as you straddled his lap. His grip tightening on your sides, fingers dipped in your flesh.
"How much time did you give your students?" You jokingly asked when his lips dropped to your neck.
"Twenty minutes," he answered and stopped, looking in your eyes again. "How much did you get?" you smiled and kissed him once.
"Twenty minutes," you whispered as you played with his ear.
"I like your professor," he whispered back, staring at your lips from under the hooded eyes.
"I like him too… A lot."
Smiling at your words Dean stood up, then dipped down just to catch you under your ass and lift you up. After sitting you down on the desk, he took away the cups and placed them on the floor; for safety.
Spreading your legs you allowed him to stand between them. Brushing your hair away he cupped your cheek and kissed you deeply, squeezing your thigh with his second hand. You didn't waste any time and kissing him back, you started to unbutton his shirt. When the material fell loosely, you caressed his strong stomach, feeling muscles rippling under your touch as he inhaled sharply. He sucked on your lower lip in response, then switched to your jawline, neck and collarbones; forcing you to close your eyes at the pleasurable feeling. When he reached this one, specific spot between your jaw and ear, a trembling gasp escaped you and your head fell back, revealing even more neck which he attacked immediately.
"Dean," you breathed out heavily, glancing at the clock. "You have to speed up." You noticed how his eyes fired up in a second. "Do your magic baby, or I'll have to help you finish in front of my friends." You flashed him a devilish smile as he wiggled his brows on you.
"Would be interesting, we have to try it one day." He winked at you and helped you stand up so he could take down your shorts and panties.
Then you dropped to your knees, taking down his pants in one move, freeing his cock. He moaned deep in his throat when, without waiting, you sucked on the tip. Looking up you saw his exposed neck as his head was tilted back. You licked the sensitive spot under the tip and smiled when Dean shivered and his body swayed a little. Taking him almost whole at once, you scraped his stomach; he instinctively gripped the back of your head which only made you growl. You bobbed your head a few times, hollowing your cheeks, tasting his flavor. Nipping on the apex every so often, dragged sexy noises from Dean what only made you weaker. You loved every tiny sound he made, you could listen to it all the time; that's why you enjoyed going down on this man so much. He was not holding back at all and it was such a turn on. You were easily losing control; wouldn't be the first time he finished like that because you couldn’t stop.
"Not today, sweetheart," not being able to take it anymore, he pulled you up, turned you around and with your front pinned to the desk you heard a low growl next to your ear.
"You have no idea how hard it is to focus while having you on the screen, knowing that you're next door, so close to me."
Strong chest against your back, pressing down your body; you could feel his heart racing.
"Vice versa, professor," you panted, feeling the weight of his cock resting on your lower back.
He fisted your hair, scraping your head and slightly lifted himself from you, kissing your shoulder blades and spine. You inhaled loudly, suddenly feeling his fingers on your clit, making small, sharp circles; drawing quiet whines from you. When his index slid inside, your body jumped in surprise. Dean chuckled low and sucked on the crook of your neck from behind; you couldn't help but smile, already drugged on him. And Dean Winchester was a high quality drug.
The last hour had been a torture. You knew he kept making moves that were waking up the corbes in your brain. Licking his lips, smiling straight to the camera, playing with his hair, "casually" flexing his body; this bastard knew exactly what he was doing.
Placing his palm on your lower back, Dean made sure you were trapped and a moan flooded out when he entered your pussy. Inch by inch he was going inside, stretching you in the most pleasurable way. You both moaned when he bottomed out, his fingers tightened even more on your skull. Your eyes rolled back with his first hard thrust; you clawed the edge of a desk. He pulled slightly on your hair and grabbed your shoulder, then started thrusting firmly, causing you to greet your teeth from the intensity. Every move, every push and pull, every squeeze and kiss was so delicious. Dean’s hot, fast breathing tickled the skin on your back, creating waves of chills that shook your body.
Dean started slamming his hips stronger, hitting your sweet spot, making your head spin. None of you were quiet anymore; the mix of your voices, moans and skin slapping on skin, filled the room. His hands appeared on your ass and he squeezed it; you expected to see red marks from his nails later. Dean's muscles were flexing with every move, his face grimacing from blissful sensation.
Even after almost a year, his game was a mystery to you; you had no idea what he was doing but the way he was moving was just different, making you feel some spiritual stuff you couldn't explain. Dean Winchester was the only guy who could make you feel like you weren't yourself; he was the only one you were completely losing control with. And with every bite you wanted more.
“Ah, Y/N,” he breathed out when you arched, giving him even better access, changing the angle a little bit.
“Five minutes, Dean,” you said almost out of voice, checking the time. “Faster.”
He growled and fastened; slamming into you with more speed, pulling you to him with every push. He was close, you could sense that by his more and more erratic movements. He couldn’t decide where to hold you, where to touch; hazed by the pleasure and the smell of sex filling the air. His voice got higher and every moan was a slightly higher pitch.
“Come on baby, let go,” you encouraged him, reaching behind you to claw his side.
“Fuck,” he cursed under his breath and scraped your back, leaving red lines on your body.
Then he bent over and his sharp teeth sinked in your arm at the same time his fingers found your clit, rubbing fast. You choked on your voice that got stuck in your throat; it was too much. He was filling you completely, scrapping every spot inside and outside that you needed. Warmth radiating from every inch of his powerful figure heated the air. Sweat broke across your bodies; a lonely drop rolled alongside his spine, strands of hair stuck to your forehead.
You managed to lift yourself up almost to a standing position; Dean palmed your throat, slightly squeezing it and kept working on you with his second hand. You started twisting, your knees sagging, eager for the relief you felt coming.
“Y/N, baby,” he licked your earlobe. “Please come with me, I need you to come, please,” he literally begged, craving for mutual finish.
“Oh my… Dean,” you warned him feeling the knot in your lower abdomen tightening unbearably. “Dean!” fiercely gripping the back of his head you leaned back on him as he kept pounding into you.
“Oh, fuck,” he stammered and thrusted forcefully two more times, then you felt his teeth sinking into your neck one more time, leaving yet another mark.
“Oh, yes!”
All of your muscles tightened to the max and then let go. Your pussy started pulsating along with his throbbing cock; it was like your bodies didn’t need any information from your brains, they knew exactly what and when should happen, they were connected.
Dean coated your walls with a hot cum; hugging you tightly, panting against your nape. You were shaking, your heart racing; breathing was problematic and if Dean didn’t hold you, you would surely hit the floor. Your nails left half-mooned marks on his forearms, so did his teeth on your neck.
You usually were slow - all touching, feeling every little inch of each other, moving smoothly but deeply, steady rhythm, building the other to the breaking point, to the edge. So when you needed to go quick, you would get crazy and high kind of easily.
“Shit, sweetheart,” Dean took a few deep breaths, trying to calm himself down.
You rested your hands on his desk, chugging, unable to stand on your shaking legs without any support. The blood in your veins was still boiling, rushing in your ears pumped by your hammering heart. Hissing, Dean slipped out of you and his seed dripped down on the floor. He showered your back with small kisses, caressing your sides and arms. You purred and turned around, softly pressing your lips to his.
“We have two minutes, baby,” you said and laughed when he moaned unsatisfied.
“This hour will be torture.” You both rushed to put your clothes on.
“I know, but then we will order pizza and watch some horror movie.” Smiling at him you opened the window and smoothed your clothes; he quickly cleaned the floor.
Standing in front of him again, you adjusted his hair and pecked him a kiss, thinking that people from your class will surely notice his blush and glassy eyes.
He looked at you with adoration and gentleness, his orbs shimmering. You knew this look; he gave you it when you first bumped into each other on your staircase, unaware that you were living in the same building. You were already crushing on your professor back then, so the fact that you were about to see him way more often than just in class made your stomach clench. That’s how it started. Later he offered you his help in some housework and studying, you became his healthy food service and after realising you couldn’t stay away from each other you opened the whiskey and let fate do its job.
You both had the feeling like you had known each other for years and you understood the other, not to mention how honest the two of you were, you still couldn’t fully believe that you were the one his heart had chosen.
“I love you,” he spoke almost like he could read your mind.
Your face lit up with a smile but the moment he bent down to capture your lips in yet another kiss this evening, you avoided it, biting your lip to shoo away a wide smile that wanted to break free and turned around heading to the door.
“See you in class, professor,” you said over your shoulder and smiled hearing his low chuckle.
A/N: Thank you for reading! I hope you liked it :) Feel free to leave some feedback, don’t be afraid to message me. Every word from you is gold <3
Pairing: Professor!Dean Winchester x Grad Student!Reader (Plus-Size)
Series Summary: Forbidden fruit. Dean knew there was always a consequence for the taking and sampling part. The question was — is it worth how good it tastes? Remembering the feeling of your soft curves under his hands, the look in your eyes, and the temptation of your lips, he had a feeling it would be more than worth it.
AN: @waynes-multiverse coined the perfect term for their “first collision” over on Patreon. Now, it’s countdown to who breaks first (again). 😏
Chapter Title: "Friendship is constant in all other things / Save in the office and affairs of love." — Much Ado About Nothing, Act 2, Scene 1; Claudio
Word Count: 5.5K
Posted on Patreon: Oct. 24, 2025
Tags & Warnings: (18+ only) Angst, college stressing, sexual tension, and smut (v. fingering, m. receiving oral, office sex), smidge of past body insecurity
♬.ᐟ Playlist: YouTube || Spotify
ᝰ.🖋️ Series Masterlist
Part 4: In the Office and Affairs of Love
December 25
Lawrence, Kansas
Mary Winchester knew what melancholy looked like. She’d felt it every day for six years. She saw it in the mirror every morning before she plastered on a smile, just to make it fit.
She also knew her sons. Both of them.
Eight years ago, her eldest hung out alone on the porch with a lukewarm glass of whiskey in his hand, just like tonight. It was cold enough for their breaths to linger on the air, the evening dwindling down to stars and violet shades behind the wrought iron fence. The ranch-style home John built with his own calloused hands still stood, a monument to his family, and everything his spirit stood for.
Dean looked a lot like him in this light. His broad frame was hunched over the wooden porch railing. His gaze was cast out to the city he used to call home, but in his mind, a whole world seemed to be in flux.
“It’s Christmas. No one’s allowed to drink alone,” Mary said, bumping his shoulder as she came up to stand beside him.
She leaned her arms on the railing like he was, and he tried to offer her a smile. She hadn’t seen many true smiles on his face in the past few years. She also supposed she couldn’t judge. Whenever her boys were home, though, she tried to be the mom they remembered, maybe even the mom they needed.
“I’m good, just getting some air,” Dean said. “It’s peaceful out here.”
“Yeah? How’s it going with work? Or…outside of work?” she asked, a leading gleam in her eyes.
He sent her a wry look. “Don’t play me. You’ve been trying to get intel from Sam since we landed.”
She smiled and rubbed his back. “I just want to know what you’ve got going on in your life. You boys are so far away. Feels like I’m always last to know.”
Dean paused, but he still shook his head.
“Nothing new to report. I’m just tired, I guess. Been a long semester.”
He took another drag of his whiskey, barely felt the burn on the way down.
He didn’t like lying to his mom. It felt like acid in his gut, coming back up through his tightening throat. He couldn’t tell her that he’d fucked up. And worse, he didn’t really regret it.
Two Weeks Ago…
Finals Week was over, but that didn’t mean Dean could rest. He still had exams to grade when he got back on Monday. It was a hell of a lot quieter now that the students were out on Winter Break. They’d return like zombies come January, feet dragging and eyes blinking slow until their coffees and energy drinks kicked in.
When Dean walked into his office, he set down his bag and was immediately drawn to a black gift box on his desk. It was long and thin and rectangle-shaped, with a red ribbon tied around it, no card to tell him who it was from.
Confused, he opened the box and found a silver pen. By the weight of it, it felt expensive, sterling silver. A small note was folded underneath it. Dean held the pen in one hand while he unfolded the note.
Give me your pardon, sir. I have done you wrong; but pardon it as you are a gentleman.
Unconsciously, he smiled. He recognized your handwriting.
Then the guilt and indigestion-inducing conflict set in.
He lowered heavily into his chair and rolled the pen between his fingers. Within seconds, he found himself setting it aside on his desk and opening up his laptop. Instinctively, he had a hunch that your note was some kind of quote. He felt compelled to look up those lines, to follow the path of your mind as he tried to understand it.
Of course.
He found the rest of it, what you might’ve felt you couldn’t say, in the final act and scene of Hamlet. As his eyes scanned the next few lines, they struck at his core.
This presence knows,
And you must needs have heard,
how I am punished
With a sore distraction. What I have done
That might your nature, honor, and exception
Roughly awake, I here proclaim was madness.
He read those lines over and over again until they blurred over, until he leaned back into his chair and breathed out slowly, closing his eyes, trying to find some kind of order to his thoughts.
Even when you apologized for something that needed none, you were uniquely you.
Now, Dean could only hope the calmer air away from the grit and chaos of New York City would drive you out of his mind for a while.
(It wouldn’t. It didn’t. And he knew he would be in danger the moment he stepped foot into his office.)
“Wow, you got her to meet your parents?” you asked.
“Dude, don’t sound so shocked!” Charlie said, stuffing another Twizzler into her mouth. “It actually went better than I expected. Mom went way too hard with the tinsel, as usual. Dad made no less than three gingerbread houses and almost lit our actual house on fire with his construction of the Christmas lights in the front yard. Dee said I basically live in a Candyland box, which, couldn’t really refute that one.”
You both were back in from vacation. Ironically, Dean wasn’t the only Kansas native. Charlie’s family lived in Topeka, yours in New Jersey. You might’ve had the easier commute, but you envied the pictures of Charlie’s two-story home, complete with a pool and three dogs.
Your dad owned a small independent music store, one of the last in the state, and your mom was a middle school Art teacher. Your parents were frankly lucky to still own your family home in the neighborhood you grew up in. It had been slowly getting gentrified for the past ten years, pricing out the middle class families who lived there.
But it was tradition for you and Charlie to spend the first week of January watching Christmas movies in your pajamas, eating way too much Christmas-themed candy that stores were trying to get rid of after New Year’s, and tying it all together with a friends’ post-holiday recap.
“And what about you?” she said, playfully shoving your shoulder while you tried to finish off one of those shortbread cookies with a peppermint Hershey’s kiss in the center. You almost choked on the pointy bit.
“Bitch,” you said with your mouth full. You shoved her back. “Nothing. I did nothing, except my mom burned the turkey so we had to order Chinese for Christmas dinner.”
She snorted. “That tracks. You guys really shouldn’t be allowed in a kitchen, by government mandate.”
“All right, my mom, yes. Totally. She should just throw away the oven mitts and commit to takeout for eternity, because my dad’s sure not taking up the culinary responsibilities in that house,” you said with a laugh. “But even I’m not that bad.”
Charlie shot you an incredulous look. “You’re fucking kidding, right? You set off the alarm a few weeks ago when you tried to make spaghetti.”
Your scoff had a bit of dramatic flair. Of course she’d toss that in your face.
“I’m sorry! I told you, I was trying to do too many things with the garlic bread, and the sauce just caught a little bit on fire.” You pointed at her with a Twizzler. “You still ate it, right?”
Charlie shook her head and continued stuffing her face with butterscotch candies while Home Alone 2 played on the living room TV.
“And what about Professor Dean? How did that leave off?” she asked, with a mischievous smile. “Did you give him a Christmas present? Handmade coupon for a free massage? Your sexiest pair of panties? Ooh, give him the little red thong! I bet he’d cream his jeans right then and there.”
“No, no, and no! Jesus Christ,” you laughed, but your face flared hot with a blush. You patted your cheeks to quell the radiation. “Well, okay, I just got him a little fountain pen. Nothing fancy. I saw it on sale, and…I don’t know, it made me think of him.”
You didn’t tell her the rest of it though. You couldn’t bring yourself to admit that you all but threw yourself at him—that you kissed him. And he kissed you.
It was one hell of a kiss. Sometimes you still felt the tingling sensation of what his plush lips had felt like; passionate, skilled, perfect. And the way he held you, masculine and firm, but also gentle and sensuous in ways that had your knees quivering where you’d stood.
And yet, in the end, you both agreed that it wasn’t a good idea. Too messy. Too risky. Too…much.
You still didn’t know what you were going to do when you saw him again on Monday. Technically you were still his TA, and when you checked your new class and work schedule this morning, your usual 5:00 to 7:00 p.m. block was still listed under his name in big, black letters.
Shit, you thought. You’d really messed up everything, hadn’t you?
The last days of your vacation spun like the frothy white flakes in a snow globe, all too soon settling into the beginning of spring semester.
Your last course schedule was filled with the hardest classes in your major. Most of them excited you, like Victorian Literature, The Evolution of Literary Criticism, Coming of Age & the Bildungsroman, and even your graduate seminar course—Topics in Women’s Literature: Class, Race & Self-Identity. Grouped together though, all that reading, all those essays, class discussions, quizzes and tests were going to be killer.
This was the home stretch, and just like your senior year of undergrad, it meant you had to find the last vestiges of your energy and put it all into finishing strong.
But that thought only reminded you of Dean. What he said to your class on review day hadn’t been the first time you heard that advice, but it was a reminder that none of this was free. You were paying for it. And it was all on you what you were going to make of yourself, now and after you graduated. Sometimes that pressure mounted behind your eyes and made your hands shake.
Which was why you knew you couldn’t afford distractions, let alone the risk of failure or expulsion. You realized that you couldn’t in good conscience continue to be Dean’s TA. It would be too hard—on your heart and on your mind.
You had to quit.
The professor had more or less the same office hours for spring as he did in the fall, and you had tried to make your schedule match as well. It meant that you knew he was in his office come 5:00 p.m. You hesitated there at the door.
Inhale. Exhale.
You forced yourself to raise your hand and knock.
“Come in,” his deep voice called from inside.
One more small moment to steel yourself, and the handle twisted under your hand.
Dean was already standing, leaning against the front of his desk with his hands in the pockets of his black slacks. Your eyes widened.
Dress shoes? Plus a white buttoned-down shirt, a sharp black blazer and a tie to match. He wore his usual neat scruff, his hair in its usual short sweep, but the rest of it was sharp, clean, like some GQ cover model.
Well, that’s just not fair, you internally lamented.
What actually came out of your mouth was—
“Hey. You look…nice,” you blurted.
“Uh, thanks,” he said, gesturing vaguely and a bit embarrassed at his clothing. “All the staff and faculty had to attend this board meeting for the Business School. Benny said I had to break out the monkey suit.”
You smiled in amusement. “That’s very on-brand.”
He chuckled. “Yeah, I guess. I’ve never really fit in much around here.”
Your smile slowly fell.
“Really? But you’re one of the most popular professors here.”
“Maybe with some of the students. Not so much with the faculty. Or the admins, for that matter. They think I, uh, play things a little too loose,” he said. And he sobered, staring back at you with guilt in his eyes. He reached back to grab something off his desk.
He held up the silver pen.
“Thank you for this, by the way. And I got your note too…” He sighed and pushed away from his desk, taking a cautionary step forward. He wanted to meet you were you were, but he held himself back. “None of this is on you, okay? So don’t apologize. Don’t feel like you owe me anything.”
You swallowed, hesitantly stepping toward him. But first, you closed the door so you two wouldn’t be overheard.
Dean’s shoulders tensed. He watched you come back into his orbit. Red flags, sirens, the whole bit flashed through his mind, but all he could do was stand there waiting for you, and whatever you might say next.
“There’s no denying that I started…this, whatever it is,” you said.
“It doesn’t have to be anything,” he said. “I should’ve stopped it. Matter of fact, we should just leave things where we left ‘em. I’ll even help you find another job. I’ll write a rec letter, or whatever you need me to do.”
You couldn’t help it. A small smile played across your lips.
“Whatever I need you to do?” you asked.
Dean’s jaw clenched. His gaze on you became all too focused, strained, conflicted.
You stared back at him as something gave way inside you. You knew this went against every firm decision you made for yourself this morning. You knew this could end terribly, proverbially if not literally in flames. But it was his kindness that undid you more than anything.
You had a suspicion that he felt this too, this...connection. It was something you didn’t know you’d been aching for, until you met him. You shouldn’t let something that important slip away, should you?
You took the risk of one more step, your fingers grasping the edge of his tie, admiring. It was black, with several tiny white and red squares that popped against his shirt and jacket. You’d like to pop all those buttons too.
A small, unsteady breath fell from your lips. You looked up him through your lashes.
“What if I just need you?” you said.
Dean said nothing. He couldn't. But his eyes followed the way the fabric of his tie wrapped around your long nails, now painted a darker burgundy. His hands found purchase on your waist, bringing you in just as much as you were leading him. He shouldn’t have let himself touch you. He should’ve just let you go.
Instead, he reached out and locked the door.
And that click of the mechanism was an audible shattering of his own resolve. He pulled you flush against him, every soft curve of your body against the firm planes of his. And his hand cupped your cheek, tilting your head up to his for a searing kiss.
It wasn’t soft or sweet. It was heat. It was frustration and yearning. It was throwing away the warning of consequences, and following the thrumming need of your hearts. It was teeth clicking and harsh breaths, your hair tangled around his fingers, his free hand roaming down your side, feeling your warmth through the fabric of your sweater, so neatly tucked into your skirt.
Your messenger bag dropped to the floor.
He turned you around with him, and his steps forced you backward until your ass bumped against the desk. He grabbed the plush of both cheeks through your skirt and squeezed you into him, rocking a gasp out you as you clung to his shoulders. You felt the press of his hard-on through his slacks.
“Up on the desk,” he ordered. His voice was rough the way you remembered after he kissed you the first time, sending a delicious tremble down your spine, and between your legs.
You did as you were told. Your ankle boots dangled off the ground after you hopped up on the desk. Dean kept a grip on your thighs, pulling you right to the edge. You took his face in your hands and kissed him this time, savoring every slow push and drag of lips and graze of teeth.
By now your lipstick was smudging into nonexistence. Your lips were kiss-swollen, but still needy, sucking his tongue into your mouth, your nails raking through his hair. He saw fucking stars, bucked his hips into yours on reflex.
Your little moan coaxed out the recklessness in him, manic and unrestrained. He pushed your skirt up your thighs and dragged your panties down until they fell around your ankles.
Meanwhile, you slid your hands under his blazer and worked it open, down his arms and to the floor. Then, you started on the many buttons of his dress shirt.
You only managed to get the first few undone before your concentration shattered. Dean’s hand traveled smoothly up the inside of your thigh now that he had you bare. His fingers parted the folds of your cunt and slipped right into your aching core, finding even more wetness than he expected. You whimpered against his mouth, clinging to his shoulder while you half braced yourself on the desk.
“Goddamn, sweetheart,” he said. “You’re soaking fucking wet for me already, huh?”
You weren’t able to answer with more than a moaning nod, but you didn’t have to. He felt the evidence dripping down to his wrist as his fingers probed deeper, experimentally, then moved up to your clit. He massaged in tight circles until it became a swollen bud. Torturous, slow movements had your hips writhing into his hand. Your breaths shallowed, puffing warmth against his neck.
“Oh fuck—please, don’t stop,” you whispered haltingly. Your nails bit into his shoulder through his dress shirt. He captured your lips in a kiss, swallowing your cry when you came. It washed over you in a tantalizing wave, your inner walls choking his fingers. He stroked one of your shaking thighs steady afterward. His fingers slowed down inside you.
“You okay?” he chuckled.
“Are you kidding?” you giggled, resting your head against his shoulder. A smile spread across your face. That just happened.
It’s still happening, you thought. A certain flash of resolve ran through you; your hands drifted down his chest and caught on the waistband of his slacks. Dean’s gaze was hot on your every move as your nimble fingers opened the little metal latch, drawing his zipper down slow.
You glanced up and met his eyes. You were really doing this.
He grasped your arms, making you pause.
“You sure? I mean really,” he asked.
You smiled and leaned up to kiss him in reassurance.
“Definitely.”
Your hand slipped inside his slacks, smooth and deliberate along the hardened length of him. He hissed at your touch, his hips canting toward you on reflex. You felt the shape of him through his boxer briefs, just to get an idea of what you were working with.
You sucked in a subtle inhale. “Oh, wow.”
He was bigger than you expected. Thick. Perhaps painfully hard.
His grip tightened on your shoulders.
“You gonna keep teasing me, baby?” he smirked.
Your smile deepened in amusement, even as you blushed at the new nickname.
“Just a little.”
You dipped low to cup his balls, massaging gently. His muttered curse, the tremble in his legs, it all satisfied you more than you were willing to admit. Your inner thighs squeezed against his hips on reflex.
Then you withdrew your hand, pushing back lightly on his chest. He quirked his head in confusion, but he began to step back in disappointment, thinking you might be changing your mind after all. He soon realized what you really wanted.
You kicked your tangled panties off your boot. It made it easier to slide off his desk and go to your knees instead. You dragged down his underwear by the waistband, just far enough to take his cock firmly into your hand. Dean had to grab onto the edge of the desk for support, a muttered curse falling from his lips.
Yours were sweet and sensuous the moment they touched his sensitive cockhead. Your eyes met his briefly, an endearing little smile dancing across your lips before you took him into your mouth.
He didn’t know that you were fighting a nervous giggle; that you were afraid of letting him down, but determined to make him feel good, and prove to him that this was worth the risk.
His other hand sunk into your hair on reflex as you salivated over his length, sliding your lips and tongue in a damn near perfect rhythm. Your worked him deeper and deeper down your throat, then sucked him all the way back up to the tip.
“Holy fuck,” Dean grunted, blinking in time with his stuttering brain. His legs wavered, forcing him to lean more of his weight against the desk. Your little giggle almost made him laugh too.
Saliva pooled down the side of his shaft, but you didn’t let it go to waste. You caught it with your tongue.
“Jesus,” he muttered, his fingers tightening in the strands of your hair. The sight of you on your knees for him was dizzying; his cock already throbbed a warning.
“Shit, hold on,” he said, grabbing your shoulder.
Your smile dropped. Before you had a chance to ask him what was wrong, he guided you off your knees, just so he could grab you up by the waist. He pulled you against him and gave you a thoroughly dirty kiss, his own talented tongue sweeping through your mouth.
His hands wandered, finding their way under the hem of your sweater after untucking it from your skirt. He wanted to see you, and finally getting to take in the sight of your tits barely held in by a black lace bra had him dragging his lower lip between his teeth.
He slipped a hand behind you and flicked the clasp open. You helped him brush the straps off and fling it somewhere by your feet.
Dean turned you around in his arms. It gave him a new vantage point, and better control to feel your body against his.
“Look at that, a perfect fit.” His voice was a rasp of whiskey in your ear while he got a handful each of your breasts and gave a teasing squeeze. “All of you, fucking perfect.”
You leaned against his chest and held onto his arms, trying to keep your moans quiet. Still, you breathed a slightly delirious chuckle.
“Wow. Been a while since a guy said something like that to me,” you said. It was half under your breath. You didn’t think he even heard it.
But Dean frowned. His fingers stilled while toying with your nipples as they hardened in arousal.
“What?” he said.
You blinked. Again, your mouth had decided to run away from you there. It now opened and closed, hesitating.
“Nothing,” you said, a weaker laugh under your words.
He didn’t like it. What he did like, was the way he got to explore every soft curve of yours under his hands. He guided your chin toward him, encouraging you to meet his eyes.
“You’re fucking beautiful, you know that?” he said.
You were captivated, mildly stunned. “U-um…thank you.”
You didn’t know why, but your eyes began to prickle with emotion. Part of it was Dean’s conviction. Though if you were honest with yourself, part of it was the words your ex slung at you when you were tossing his shit out of your apartment. He’d still been high, hungover, humiliated to be a walking cliché—caught dick-in-hand with some sorority girl from his Film Appreciation class—and upset that you wouldn’t take his excuses.
But he’d had no problem hitting you where a small, niggling insecurity had crept in like a shadow, distorting the truth.
“I’m sorry, okay? I was high, and drunk. Please, why can’t we just work this out?”
You rolled your eyes and continued tossing his Nintendo Switch controllers out into the hallway. He was muttering curses under his breath, half trying to pick up his shit, half still trying to grab your arm. You yanked it out of his grasp.
“Because this is fucking mortifying. Because I’ve had enough. And because you’re a fucking pig, that’s why!” you snapped. Other people were starting to peek out into the hallway, whispering, snickering. Many of them were students that you two both knew.
He stood there for a moment, embarrassed and angry.
“Well, maybe I was tired of fucking one.”
After a moment, you managed to blink the sting of memory out of your eyes. You gave Dean a smile that didn’t quite ring true.
His brows furrowed. He tilted your face up to his and lured you into a kiss; it was softer, but still laced with an underlying heat.
“Look, I don’t know what you’ve got goin’ on in your head,” he said. “I don’t know about that ass-clown you dated, or anybody in between. But sweetheart, so far there ain’t a part of you that I don’t like. And there’s no part that I’m not gonna fucking ruin.”
A hot blush spread across your face. You started to smile for real, but a small gasp escaped you as he guided you down onto his desk. You certainly believed him now.
And it was the confidence boost you needed to push away those old thoughts, beating back the shadows.
Your forearms kept you upright at the angle you thought he wanted. Already your thighs were shaking, your pussy clenching on nothing in anticipation when he guided your skirt up higher over your hips. He reached into his pocket and withdrew something from his wallet.
You glanced over your shoulder and watched him tear the condom packet, heard the shuffle of his clothing and his muttered curse as he fitted himself. Then you felt him at your entrance, his cock just as hard through the condom and lubed up in your wetness.
“Still okay, sweetheart?” he checked, rubbing your hip.
“Yes. Yes, please,” you said, a hint of desperation as you tried to keep your voice quiet.
He didn’t need to be told twice. Slowly he pushed inside, shallow thrusts, working himself in deeper and deeper, until he was fully seated in the deepest part of you. You bit the back of your own arm to stifle your moan. There were no words in your head to even formulate how good it felt to be filled by him. Goosebumps spread across your skin. Already your core was quivering around his length.
“Goddamn, feels so fucking good,” he gritted out. “Tell me. How you feel, sweetheart?”
“So good,” you choked on a whisper, shuddering as he found a new delicious angle inside you. “Oh, God…”
Dean smirked. His grip on your hips tightened a fraction. “Shit, we should’ve put on some music or something. Walls aren’t that thick…”
Not to mention that he shared one with Benny, of all people.
“Fuck, give me my phone. Or yours,” you said, laughing just at the craziness of this. But Dean did as you asked. He grabbed his phone from his loose pocket, unlocked it, and slid it to you across the desk. You opened up the music app and played the first song that came to mind—something you knew he would have.
A smooth guitar intro bled into a man’s familiar verse.
“Hey lady, you got the love I needMaybe more than enoughOh darling, darling, darling, walk a while with meOh, you've got so muchSo much, so much…”
Dean chuckled, having to pause and kiss your shoulder. “Nice.”
Led Zeppelin’s “Over the Hills and Far Away” swept you off in its current, while Dean’s smooth strokes went deeper, as if in time with the music. He spread your thighs a little wider to accommodate himself, dug his fingers into supple flesh. Your toes began to curl, your fingernails hooking around the edge of the desk.
“Oh, shit,” you uttered. That coil in your lower belly was tightening again. It was almost too much, overwhelming, yet not quite enough.
You slipped a hand underneath you to find your clit. Dean noticed, moved your hand away so he could help you himself. His fingers were a calloused dream, providing just the right kind of friction to make you almost faze out of your own skin. Your body was awash with heat and tingles when you came on his cock.
White little starbursts behind your eyes. A delicious throb in your cunt. Your inner walls gripping him tight.
“Dean,” you breathed, awed and wanton.
Even better than he fucking imagined.
You smothered your own mouth, muffling the sound of your moan. He came moments later; his release hit him hard enough to rock the vertebrae in his spine. His teeth found the soft flesh of your shoulder as his hips rolled to a stuttering halt. “Fuck…”
A grunt forced itself from his throat, and he bucked hard then, knocking a gasp out of you as he spent himself into the condom.
His body caved in around yours. Panting breaths echoed in the stillness.
He noticed when your arms began to shake underneath you. He pushed himself off and helped you stand upright. Your legs were shaky too. After you lowered your skirt, he held your elbow in support while you bent down to find your bra and panties.
“Oh shit,” you laughed.
Neither of you had noticed or cared as entire stacks of essays from last semester had gotten knocked over and strewn to the floor.
“You fucked up your own hard work there,” Dean remarked.
And you both laughed.
"Don't you mean we?" you quipped.
You lowered down first though, kneeling to sweep it all up. He joined you a moment later, after tucking himself back into his pants and zipping up. His dress shirt was a hot mess and his suit jacket was…some-damn-where. But he’d deal with that later.
For now, it was enough that his gaze got caught up with yours when you happened to glance up at him. You paused, smiling a little shyly.
He couldn’t help smiling back.
There on your hands and knees, you crawled forward and met him with a kiss.
You both knew it then. After tonight, there was no going back.
Just a couple of hours later, you made it back home to your apartment and showered before your roommate had a chance to see your disheveled, thoroughly debauched state.
Despite the January chill on the air, your face had stayed warm and blushing while you sat alone on the subway. It would flare up again every time you remembered who was at fault for the sticky wetness between your legs, and why even now, in the privacy of your kitchen, you were still walking on uneven ground.
Dean Winchester had thoroughly wrecked you.
“You’re all smiley again after back-to-back classes,” Charlie observed. "Something good happen today?"
You were puttering around in your pajamas, heating up some chicken tortilla soup. A small prickle of wariness ran down your spine. You tried to school your face into a more neutral expression.
“Yeah, I mean, I had a feeling taking Victorian Literature in my last semester was going to be intense, but Professor Dodd assigned great books this semester. I haven’t read Wuthering Heights in forever.”
“Uh-huh.” Charlie’s eyes narrowed with playful suspicion. “And how was work?”
You hesitated. Thinking fast, you decided to focus on your job at the library.
“Well, Marv is still Marv. He only ever comes out of his office to gossip, so at least I know all the tea. Apparently they’re doing all these renovations to the Business School by cutting the funding for the other departments. That’s why my hours got reduced.”
“Wow, that’s shitty,” Charlie said.
“Yeah, but apparently that school is EU’s biggest moneymaker, so that’s how Dr. Crowley’s justifying it.”
“That’s our education system for ya.”
“Sadly,” you said. “I was lucky to get my second job. I guess they had just enough room in the budget, or Professor Lafitte was just tired of Dean turning in all his paperwork late.”
Charlie rose a brow. “Dean, huh? You guys are on first-name basis now?”
You paused in your soup stirring, ladle in hand.
Shit.
“Well, kind of. Just when it’s the two of us in his office,” you said, trying not to smile to yourself.
It was more or less the truth, after all.
And for now, that was all you felt comfortable sharing. Not because you thought Charlie would out you to the school administration. She had been the one encouraging you from the beginning. But…well, maybe you just didn’t want to get into it. You didn’t even know what it was, exactly, so it felt safer to keep a secret for now, even if the lie did sting.
“Interesting,” Charlie remarked.
You noticed the way she was looking at you out of the corner of her eye, but you just continued your search for tortilla chips. And all the while, you ignored the question steadily pressing upon your mind.
What happens tomorrow?
AN: Well then. 😂 Was it everything you thought it would be? We've reached the point of no return, which of course means that here's the part where things get fun and complicated. 😜
See you next Sunday, friends...
Next Time:
“Are we really doing this again, here?” you asked breathlessly.
“Looks like it,” he said, kissing his way down your neck.
You were right. It was a risk. But right now, Dean couldn’t really bring himself to give a fuck. He had your thighs straddling his lap, your pretty blue sweater dress hiked high over your hips. He held you in place with a firm grip there, probably leaving his fingerprints behind.
He occupied your lips so you couldn’t voice any more smart rebuttals. You moaned softly, letting your fingers sink back through his hair. Dean’s desk chair creaked with every reflexive rocking of your hips against his.
At least you two were more prepared this time. Once of his records played at a decent volume: “Try and Love Again,” by The Eagles, off the Hotel California album. But there had been very little discussion before you found yourself back in the pull of whatever this was, whatever it could be.
📕 KEEP READING: PART 5
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This is for an older one, and I think the author deactivated their account. There’s one with reader x priest cas, and eventually reader x priest cas x professor dean. It’s literally the best smut I’ve ever read. I remember it had 4 parts, then very quickly got to 10, but before I found parts 5-10, the tumblr was deactivated. I swear I found it elsewhere though, thank you!
Help! xD I’m searching for fitting Prof!Sam pictures and oh my gosh, I already knew it because of various Prof!Dean stories and I mean - he’s Jensen Ackles - of course he is hot, but damn! I can picture him perfectly as professor! Look at these pics! I’m drooling... ❤️🤤
