#Dean Winchester x male reader

[l1tw1ck]

dean winchester consumes my mind LAWDDD I beg for anything with that man, surviving off of scraps looking for more top male reader x dean 🤕

- 🛸

No Longer a Mentor

Sub!Bottom Dean Winchester x Top!Male Reader

☆ Word Count: 1,512 ☆

After spending his young adult years with you, his mentor, more than his father, Dean found himself falling for you. He eventually made a move and forever changed the dynamic of your relationship

🕯️: well luckily for u, i just finished this draft :3

CW: Age Gap, First Time Bottoming, Blowjob, Fingering, Frottage (Sort Of), Creampie

Dean’s known you for a couple years, you're a friend of his dad’s and a fellow hunter. You became his mentor in place of his father, who often hunted on his own and left Dean in your care. You liked to stay in your state since the area was basically a supernatural magnet while his father preferred to travel the country so he chose you to finally allow Dean to stay in one place for more than a week. If you were anybody else, Dean would've been annoyed that his dad didn't take him along despite his age and experience. Instead of going to college, Dean spent those years learning to hunt with his father and mostly you. Thanks to all the time you spend with each other, his allegiance to you is almost stronger than his allegiance to his father. He hangs on your every word and treats you like a god. It's thanks to you that he finally accepted his bisexuality. But he doesn't want to tell you that.

He first started feeling differently towards you when you started to become more physical with him. You often hold onto his shoulder with your strong hand or pull him out of the way by his waist and it drives him crazy. He so desperately wants to feel your hands on other parts of his body and vice versa. Your voice makes him weak in the knees and you sound especially attractive when you've found your prey. You're much older than him but he can't get rid of his feelings for you. He tries his best to be content with just having a crush.

After you two had dinner, you decided to drink with him. The two of you laughed and talked over a few cans of beer and deepened your relationship further.

“You ever been in a relationship, [Name]?” Dean asks, slightly tipsy.

“A few. I mostly slept around in my college years and experimented a bit with other hunters but in the end I decided to marry my job instead.”

“Why?”

“I wanted to marry someone I could tell everything to so I tried dating within my circle but none of the hunters seemed to click with me in the ways that really matter.”

“That makes sense…then you probably haven't…” He trails off.

“I probably haven't what?”

“Had sex…lately……”

You laugh. “No, I haven't. Honestly, I think getting laid would really help me. It's been a rough couple weeks.”

“I…” Dean gulps. “I could help with that….if you don't mind…….being with a guy..”

You look at him in surprise. “You're drunk.”

“I’ve only had two cans and a half…You know I don't get drunk that fast.”

You look at him differently, no longer with the eyes of a mentor. “You’ll bottom?”

Dean nods.

You smile in amusement. “I might be a little rough, can you handle that?”

He nods again, more enthusiastically this time.

“Come here.” You motion for him to come over to your side of the table. He stands in front of you. “Kneel.” You order. Dean immediately kneels, his cock steadily growing in size. You unbuckle your belt and pull down your underwear. Dean stares at your cock in awe, body heating up as he watches you jerk it to its true size.

“Fuck. You’re big.” He breathes out.

“Too big?”

“I can handle it.” He says, licking his lips.

“Attaboy.” You run your hands through his hair. Dean blushes. “Ever done this before?”

“Never..” His eyes are trained on your length.

“Is this your first time with a man?”

“Yeah…”

Your gaze changes. Dean shivers in arousal. “How long have you wanted this?”

“A long time…I’ve been…fingering myself, in case we….” He looks away.

You grin, turned on by the thought of that. “You'll have to show me that some day.”

Dean’s face gets redder.

“Now, let me see how you suck cock.”

He's so hard right now. He opens his mouth and slowly swallows your length. He makes a dragged out moan in pleasure as he feels your thickness enter him. Pre cum leaks out of his cock as he imagines how it’ll feel in his ass. He bobs his head up and down enthusiastically, mimicking his past girlfriends by simultaneously swirling his tongue around your shaft.

“Fuck–” You moan. “That's it– good boy.”

Words can't express how happy Dean gets when you praise him.

“You're better at this than I expected, baby.” You smile at his cuteness. He can't hide how pleased he is. “You like sucking dick, don't you? I never thought you’d be a cock slut, Dean.”

He moans. He’ll happily be your cock slut. He pulls away and licks your length in a very sexy way, gaining more confidence thanks to his elevated horniess. “I love your cock, sir.”

“Of course, you’re my cock slut.” You press your hand against his cheek. “Stand up and take your clothes off, I wanna use your other hole.”

Dean’s cock throbs even more. He stands up and quickly removes his clothes, shivering under your hungry and lustful gaze. You pat your lap and he quickly sits on top of you, your shafts pressed against each other.

You grope his ass. “I don’t have any lube..” You trail off, mesmerized by his soft butt.

“I already fingered myself earlier.” He smiles.

“Good boy.” You praise him. “Then spit’ll be enough. Say ‘ah’.” You bring two fingers into Dean’s mouth. He sucks on your fingers in the sluttiest way he can before you take them out and gently push one of your saliva covered fingers inside his soft hole. You give him a moment before adding the second, then you start to finger him.

Dean lets out the prettiest moan you’ve ever heard. “[Name]~” He arches his back and subconsciously thrusts his hips, his cock rubbing against yours. “Your- yours feel so- fuck~” He groans. “So much better!”

You moan as well thanks to the sudden friction. You bring him into a sloppy kiss, the temperature between the two of you steadily rising. Dean pulls away first, more desperate for air, and presses his forehead against your shoulder. “Don't stop– mm- gonna come~” He whimpers. Your fingers find his prostate, an immediate gasp of pleasure leaving Dean’s lips. He throws his head back. “There! Yes!” He moans, grinding against your cock even faster. The combination of his moans, his expression, and his cock against yours all contribute to bringing you to closer your orgasm.

Dean comes first, cum splattering over the two of you. Yours comes second thanks to the amazing look on Dean’s face.

“You're so fucking sexy, Dean, you know that?” You take your fingers out and knead his ass.

“I know.” He gives you a kiss. “I want you inside me.”

You lift Dean up and slowly lower him down on your cock. You both let out noises of pleasure as you penetrate him. He bites down on his lip, thoroughly enjoying the feeling of his ass stretching to accommodate your girth. Once you bottom out, you give him time to get used to it. “Your cunt feels fucking amazing.” You groan. It's hard to hold yourself back but thankfully for you, Dean has no intention of waiting any longer. He places his hands on your shoulders and starts riding you. He quickly loses his momentum as the pleasure begins to overwhelm him. You help him out by grabbing his waist and doing the work for him, allowing Dean to fully enjoy himself.

He knew anal sex would feel good, especially because it's anal sex with you, but he never really had an idea of how good it’d feel until now. Now he's completely blissed out and only able to moan like a slut. It's especially thanks to your quick and rough speed that he's unable to think properly. You couldn't get yourself to go slower even if you tried. His ass just feels way too good.

“Your ass is perfect, Dean–” You groan. “So fucking good-” You hold him and stand up then gently place him on the table after clearing it of the empty cans. You rut into him like a monster, so horny that you feel like you could fuck him all night. You can never get enough of him.

Dean arches his back and shakes as ropes of cum spurt out of his dick. You know you should stop, or at least slow down, but you can't. “‘M sorry baby, fuck–” You moan, hanging your head low as you find your orgasm approaching. “‘M gonna come inside, okay? Gonna fill up your tight fucking cunt with my seed–”

Dean’s conscious enough to understand you. “Ye- yes!” He grins. He's been wanting to know what it feels like to get creampied. “Co- come inside!”

Encouraged by his words, you spill your cum into his warm and welcoming hole. Your thrusts come to a stop and the two of you start to catch your breaths.

“That…was so fucking good.” Dean says, leaning back.

[chaoticforever]

When The Dark Crawls | Yandere Dean Winchester x Male! Reader

Summary: Everyone knows that when a cat chases a mouse, the mouse looses. Dean lives for the thrill of the chase, and Y/n L/n? The man just wanted to leave.

A/n: Not too sure about this one.

Damn these handcuffs, Y/n thought. 

The cold metal of the handcuffs dug into his skin, causing him discomfort and making it difficult to move his right hand. He gazed around the area, hoping to find something that could allow him to unlock them, but didn’t see anything. He needed to find something fast before a certain someone came barging in here.

And that someone is Dean Winchester. 

A well-known hunter who had saved Y/n's life from bloodthirsty vampires that wanted to suck the blood out of him. In the beginning, Y/n had been so grateful to have met the man. He would be dead right now if it wasn't for Dean, after all.

However, as it turned out, that wasn't the last time they had seen each other. The following week after the whole vampire incident, the h/c man had been attacked again, and it seemed like he had nothing but bad luck with all these supernatural creatures attacking him for no reason.

Once again, Dean was there to save the day. He had shown up at the abandoned house they had Y/n trapped in with lots of silver bullets and managed to kill the werewolves and free Y/n from his binds.

Again, Y/n had thanked Dean for saving his life, and Dean just said that it wasn't an issue and that maybe he should stay with him tonight to ensure he was safe. The hunter laughed it off as a joke, but Y/n decided to take him up on that offer. He didn't want to risk another near-death experience. They say that third time's a charm, and next time he might not be so lucky to get away like the last two times.

On that day, Y/n asked about Dean's life and the circumstances that led him to engage in combat with these creatures, which he had not even believed in until a week prior. Dean explained to him that he and his brother hunt these monsters and it's the family business. Y/n couldn't imagine growing up like that, but he told Dean that if he ever needed any form of help from him, such as a place to lay low to let him know. Dean did save his life so Y/n believed that he should reciprocate.

And a friendship between them formed, where Dean would stop by whenever he was on a hunt to check in or if he simply wanted to hang out with Y/n. Y/n always welcomed him. It's not like he had many friends, so he was glad to have another. However, he had noticed something.

Like the way Dean looked at him.

Y/n was not stupid. In fact, he was quite perceptive, and he was aware that Dean had a crush on him. He made sure to let Dean know that despite his gratitude, he doesn't share the same sentiment. Dean is an attractive guy, with beautiful forest green eyes, yet he only perceives him as a friend. After the rejection, Dean said it was fine as long as they were still friends.

However, it seems that Dean lied to him, as evidenced by the way he continued to touch and stare at him. In passing, Dean would find different excuses to touch or brush up against him. He found reasons to be near Y/n; their paths crossed more frequently than before. Y/n would turn a corner, and Dean would be there, leaning against a wall with a smirk on his face. He'd be at the same coffee shop, sitting at a nearby table, looking at him with a predatory gaze. When he went on a date, there was Dean, glaring at Y/n's date the entire time with a steak knife in his hand.

Hence, he felt increasingly uneasy with Dean's constant presence, but whenever he mentioned it, the hunter insisted that he was protecting him. Y/n did not share this perspective and informed Dean that he needed some space away from him. Dean's jaw tightened, and he warned Y/n that he'd regret his dismissive treatment.

Later, he discovered that Dean had been quite serious in his words, as the day Y/n's car unexpectedly broke down on the road one night and Dean kidnapped him, taking him to a secluded cabin far away. Dean claimed that Y/n belonged to him and was protecting him from everything that was evil in the world. He had to do it.

Y/n had attempted to escape before, but he was recaptured by Dean every single time. As punishment, Dean would spank Y/n's bare ass with his hand. Since then, he had learned not to attempt an escape while Dean was present, opting instead to try when he was absent. It wasn't fair that Dean decided to ruin his life, and he was determined to reclaim his freedom.

The h/c-haired male opened the drawer next to the bed and was relieved that he saw a paperclip. He knew people usually pick door locks with this clip, therefore, he was hoping it could pick a cuff lock.

Quickly, he bent down and picked up the paperclip, his fingers shaking as he tried to manipulate it into a makeshift key. He inserted the bent end into the keyhole of the handcuffs, twisting and turning it in a desperate attempt to unlock it. Sweat beaded on his forehead as he struggled.

"C’mon," Y/n muttered under his breath. 

Finally, after what felt like an eternity, the handcuffs unlocked, and the cold metal fell off his wrist. Thank God. He exhaled, rubbing his tender wrists, still feeling the lingering sensation of those handcuffs. I am free. Not wasting another moment, he stood up and darted out of the room, peering through the blinds to survey for any sign of Dean. A wave of relief came over him when he didn't spot the Impala.

Y/n's heart pounded in his chest as he bolted out of the cabin, his feet carrying him farther away from his captivity. Y/n didn't know where he was going, but he didn't care. All that mattered to him was getting as far away from this location as possible before Dean realized he's gone. Adrenaline coursed through his veins as he continued to run through the woods. despite him feeling incredibly exhausted.

Soon, Y/n reached the road and was so overjoyed when he spotted a car coming down the road. "Hey, stop!" Y/n jumped in front of the car and threw himself in front of it, causing the driver to slam on their brakes before the car could hit him.

The driver — a tall guy with brown hair —exited the car and promptly approached Y/n, looking worried. "Are you okay, sir?"

Y/n shook his head, his voice breathless from the running he did. "I'm not. This guy... he kidnapped me. Please, help me."

The tall man nodded. "I'll help you. Get in the car." He opened the passenger door.

"Thank you," Y/n slid into the passenger seat and buckled up as the other male shut the door and got behind the wheel.

"It's no issue," he turned the keys and the car roared to life. He stepped on the gas and the car cruised down the open road. The man glanced over at the one sitting in the passenger seat. "If you want, you can stay with me tonight. Then we can deal with whoever took you tomorrow."

"That would be great, thank you again." Y/n was sincere. "Do you have a name?"

After those words escaped his lips, Y/n wanted to hit himself. Of course, he has a name. Everyone on this planet has one.

The driver laughed. "It's Jared. And you?"

"Y/n."

During the remainder of the drive, Jared maintained a focused gaze on the road ahead while Y/n observed the passing scenery through the window in thought. The events of the past few months with Dean had left Y/n a bit shaken, but he felt incredibly fortunate that someone had been driving by at the right time to help Y/n escape from that stupid hunter.

When Jared brought his vehicle to a halt, Y/n shifted his attention to the imposing structure before him. The exterior looked quite old, and Y/n turned to face Jared, his expression marked by confusion.

"Uh, why are we here? I thought you said you were taking me back to your place."

"And that's what I'm doing now," Jared said. "This building is where I live. It's my bunker. You'll be safe here, don't worry."

Y/n regarded the place with suspicion, feeling a sense of unease that caused warning bells to ring in his mind. Despite his apprehension, he chose to ignore his intuition. After all, Jared had gone out of his way to help him, even though he wasn't obligated to, and Y/n decided to trust him. If it wasn't for Jared, he would still be at the cabin with Dean, and that was not a situation he wanted to be in.

Jared opened the car door for Y/n and escorted him inside the bunker. Despite the unappealing exterior, the interior was surprisingly inviting. Y/n appreciated the contrast. Jared then led Y/n to the room where he would be staying for the night, excusing himself to retrieve a blanket.

Y/n took a moment to assess the room, noting its basic amenities: a bed, a desk, and a drawer with a lamp, which was the only light source. Despite its simplicity, Y/n found the room to be quite inviting.

Later, Jared re-entered the room with a blanket, fresh towels, a washcloth, and a toothbrush. "Here's a blanket in case you get cold, a toothbrush for your teeth, and a towel and washcloth for your shower," he explained, placing the blanket on the bed, the toothbrush on the desk, and the towel and washcloth on the rack. "Get some sleep. I know it's been a long day."

"Thank you so much, Jared. I don't know what I would've done without your help." Y/n expressed his gratitude once again because he needed this man to know that he was so grateful for helping him.

Jared smiled reassuringly at Y/n. "No problem at all. I'm just glad I could help."

Jared left the room and closed the door behind him. Y/n lay on the bed and put the blankets over him, closing his eyes.

He was finally free.

Dean couldn’t get to him now.

XXXXX XXXXX

The next day, Y/n awoke feeling utterly refreshed. It had been a while since he'd slept so well, and according to the clock, he had slept for more than twelve hours. Although he hadn't intended to sleep for so long, he supposed his body needed it.

Rising up from the bed, Y/n gathered his towel, washcloth, and toothbrush, and proceeded to the bathroom. After a brief exploration, he found the bathroom and removed his clothes before entering the shower. The warm water cascaded over his skin, providing a soothing sensation as it cleansed his body and his mind.

After taking his shower and brushing his teeth, he returned to the guest room and he decided to wait for Jared to return so that they could discuss their next move.

Folding the covers meticulously, Y/n heard the door creak open from behind. Knowing that it was Jared, Y/n initiated a conversation without turning around. "Hey, Jared. Thanks for allowing me to—"

Panic seized Y/n's heart as he retreated a step. There, in the doorway, was Dean Winchester with a devilish smirk on his face that sent a shiver down Y/n's spine. No! Y/n's thoughts raced with alarm: he was free. How did Dean find him again?

Dean edged closer, attempting to narrow the gap between them. "Surprised to see me, Y/n?" he mocked, voice laced with amusement from the fear in Y/n's eyes.

Y/n retreated, pressing his back against the wall. "H-How did you find me?" he stammered, his face contorted with fear. The intimidating man's presence made it impossible for Y/n to conceal his terror.

A dark chuckle emitted from Dean's lips as he closed the remaining distance between them. Now face-to-face with Y/n, he slammed his hand against the wall beside him, trapping him against it. "Oh, I always find what's mine," he declared. "And you, sweetheart, are definitely mine."

"I'm not yours!" Y/n retorted, but his defiance was quickly overshadowed by a pressing concern. "What did you do to Jared?" he asked, worry clear in his tone.

Dean's smirk widened. "Jared's not real," he divulged, causing Y/n to stare at him in bewilderment. "His real name is Sam, my brother. And this bunker? It's ours."

Y/n felt his world shatter once the truth unraveled. He had never escaped; Jared, no Sam, brought him back to Dean. Y/n had been deceived from the beginning.

"This can't be true," Y/n whispered.

Dean's fingers trailed possessively down his arm. "It is true, my little plaything," he gripped Y/n's jaw and forced a hard kiss upon him, only to break away when Y/n continued to resist his advances. "Stop fighting it, pretty boy. Just let it happen."

No, this was bullshit. Y/n wasn't going to just let it happen or continue to cower in submission. Y/n delivered a swift kick to Dean's groin, causing him to crumple to his knees, clutching his injured area. He fled as Dean's chilling laughter echoed throughout the place  Dean taunted Y/n, urging him to run, claiming that he loved the chase. Y/n sprinted, feeling the wind whip against his face. He needed to get away on his own, unable to trust anyone in case another person he bumped into happened to be acquainted with Dean.

The surrounding area seemed devoid of buildings and people for miles, but in the distance, Y/n saw an abandoned house. It was his only option. He dashed inside. The interior had peeling wallpaper and boarded-up windows, yet it didn't look that bad. Y/n figured that Dean wouldn't consider searching for him here. His plan was to remain hidden until he was certain that he was safe, free from Dean.

The floorboards creaked beneath Y/n as he raced up the stairs, and the bathroom door was the first one he encountered. Y/n didn't hesitate before entering the shower and closed the curtain, trying his hardest to calm his ragged breathing.

Seconds turned into minutes, and in the deafening silence, Y/n believed he might have escaped Dean's clutches this time. But the illusion shattered when he heard doors opening, the floorboards creaking, and the taunting voice that was Dean's. 

Suddenly, the bathroom door opened, and Y/n stopped himself from breathing.

"Y/n, are you in here?" Dean's voice was laced with false sincerity. "Get out here. There's no point in hiding. I'll find you."

Y/n remained silent and unmoving in the shower, but it became very challenging, particularly as a spider crept up his leg. Not now. Get off me. The spider, though, disregarded Y/n's silent plea and kept crawling. Unable to endure the crawly sensation any longer, Y/n used his right foot to kick the spider off his left leg and killed it as quietly as he possibly could.

Y/n's heart pounded.

Two steps outside the bathroom, the green-eyed male halted, his attention drawn by a faint noise emanating from the shower. A smirk tugged at his mouth as he turned around, his gaze narrowing.

"So, that's where you are?" Dean walked back into the bathroom and yanked the curtains open, revealing an empty space.

A moment of confusion clouded Dean's face as he scanned the empty shower for Y/n. Unbeknownst to him, Y/n had silently exited through the second door connected to the bathroom and hidden in the nearby room's closet. This cat-and-mouse game between them intensified with each passing moment, but still, Y/n remained steadfast in his determination.

Yet, at the same time, Y/n struggled with the fear of being caught. He knew Dean was a highly skilled hunter, who's good at tracking people down. His chances of escaping were slim to none, but he was going to take his chances, nevertheless.

Y/n could hear Dean's footsteps echoing through the house, growing louder as he approached the room Y/n was hiding in. Then, the door to the room opened, and Y/n remained silent and still as Dean sauntered fully into the room. Not again.

"Come out, come out, wherever you are," Dean persisted, his voice saturated with that sick, sadistic satisfaction. "You can run, but you can't hide from me forever."

Y/n's fingers trembled as he searched for anything he could use as a weapon, but there was no weapon in the closet. Nothing. Y/n pressed himself against the wall, accidentally triggering a hidden mechanism that pushed him backward into a secret room nestled in the closet.

"Just you wait," Dean said, approaching the closet, his fingers curling around the handle with a predatory grace. "I have so many things in store for you, and you are going to love every fucking second of it. Ready or not, sweetheart, here I come."

With a swift motion, Dean yanked open the closet door, anticipating the sight of Y/n cowering in fear. To his surprise, the closet showed nothing but empty space. Dean's laugh echoed through the room. "I love this little game of cat and mouse, but trust me — I always catch my prey."

In the hidden room, Y/n's ear was on the wall, hearing the closet door closing and Dean's retreating footsteps. Y/n pushed open the secret room's door, entered the closet, and emerged into the main room.

The hidden man cracked the door open, the hinges silent, and he peered through the slightly ajar door. He observed Dean going up the stairs, heading to the attic. This was his opportunity, his one chance at freedom. Carefully, he eased the door open fully, ensuring not to make a sound.

Y/n's heart thundered in his chest as he tiptoed down the stairs, his eyes vigilant for Dean or his brother. He did not need any surprises. His pace quickened as he headed for the door, his hand hovering over the knob. He had done it. He won—

Suddenly, Y/n's body was sent crashing to the floor. Dean had appeared out of nowhere and tackled him to the ground. No, Y/n thought, his hopes shattered.

Y/n struggled to free himself from Dean's grasp and crawl toward the door, mere inches away. Dean, however, didn't plan on letting Y/n escape him this time. His grip on Y/n's legs remained firm as he pulled Y/n closer. Then, he pinned Y/n's hands above his head and placed his knee on Y/n's crotch, immobilizing him.

Dean smirked triumphantly down at his captured prey. "Man, that was a fun little game of cat and mouse, but you should know that you're my bitch." He reached into his pocket and retrieved a syringe, heightening Y/n's panic. Y/n struggled to free himself, but Dean's strength was overwhelming.  He took the cap off and quickly jabbed the needle into Y/n's arm. Weakness washed over Y/n, rendering him helpless against his impending fate.

The green-eyed hunter chuckled darkly as he looked down at Y/n, caressing his face and letting his fingers trace over Y/n's lips. "I'm taking you home now. You'll never be able to escape me, pretty boy. Stop trying, and get used to being mine."

Y/n was starting to think that Dean was right. There's no way he can escape him.

Dean felt a sense of triumph as he looked down at Y/n, his little plaything. He had won, and there was no turning back. He knew that he had done terrible things to get him, but he didn't care. All that mattered was that he had Y/n, and no one would take Y/n away from him.

As the tall man carried Y/n away from the abandoned house and to the bunker, he could feel Y/n’s body tense up in his arms. Dean knew that he was terrified, but he didn't care. He would do whatever it took to keep the other man with him, even if that meant resorting to violence.

Dean placed Y/n on the bed in his room, their room, and could sense Y/n's fear permeating the air. He relished every bit of it, loving that Y/n was afraid of him and would soon understand who owned him. Dean needed to break Y/n, to make him see that Dean was his one protector from danger. He was doing all of this for Y/n, to ensure that he was always safe.

Dean climbed into the bed, wrapping his arms around Y/n and pulling him close. He could feel Y/n's body trembling with fear, but he didn't let go. He had to show him that he's in control. Now and always.

"It's alright, baby," Dean whispered in Y/n's ear, planting a kiss on the back of his man's neck. "I'm here, and I'll protect you from anything that could harm you, but don’t even think of trying to leave again unless you want a punishment. There’s no place you can go that I won’t get you."

Y/n remained silent, which didn't bother Dean, since he knew that after this day, Y/n wouldn't dare try to leave him again.

The green-eyed man held him close, and he thought about all the things he would do to keep Y/n with him. He would make sure that Y/n never left his sight, that he never spoke to anyone else, and that he was the only one who could protect him.

After all, Dean killed the few friends Y/n had to make Y/n dependent on Dean. He had proven his love and devotion to the man in the most extreme way possible.

And now he would do whatever it took to make sure that Y/n loved him back.

XXXXX XXXXX 

[suiternatural]

national underwear day but WE KNOW. WE KNOW HE LIKES WEARING PINK LACEY SATINY PANTIES🫵🫵🫵

[spermeboy]

DIRTY DEAN!

pairings: dean winchester x male reader

summary: after dean helped you out from an ancient curse, you decided to reward him with a special treat.

requested by: anonymous

warnings: SMUT, extreme fuck, humiliation and face slapping kink, choking.

"Thanks for your help back there" you say to him softly as you wipe some of the blood off his face and place some plasters over cuts, he winces slightly "o-ow" he says in a low soft tone. "Sorry Dean" you whisper to him gently caressing his cheek, you both stare deep into eachothers eyes until you feel him grip onto your hips as he pulls you onto his lap in the drivers seat. "D-Dean-" you begin to speak until he places a finger on your lips "shh baby" he whispers to you in his low seductive voice.

Dean's grip on your waist tightens and he begins to push you back and forth making you grind your hips down against his growing bulge, "m-mhm" Dean groans out as you continue to grind down against his bulge. "Someone's horny," you lean down to whisper in his ear as you gently begin to nibble at his earlobe. Dean grunts slightly as he pushes you off him lap and into the backseat where he climbs into the back seats towering over you in the car.

Dean wraps his hand around your throat, pulling your face closer to his, "so perfect," he mumbles to himself as he admires your flustered face. Dean presses his lips softly against yours as he tightens around your throat, turning you on more as you both begin stripping off naked, trying not to break the kiss. Once you're both naked and finally broken the kiss to come up for air, you stare and admire eachothers naked bodies.

You lean back against the backseat, and you pull your legs up to reveal your bare asshole for him. It pulsates slightly as the cold air hits it. You become all flustered once Dean finally leans forward and presses a soft kiss against your hole before his eyes change dark and ravenous as he dives him to lick wet strips up your hole before showing his index finger in.

He continues sliding his finger in and out of your hole before pulling out completely, and he begins to unbuckle his belt, pulling it off and striking it across your ass "A-AH!" You yelp out, but your dick leaks like a facet. He strikes your ass again and again until your ass is red raw, he pulls down his jeans and underwear stuffing his underwear in your mouth.

The salty taste of pre-cum soaked in his underwear caused your body to shudder until he pushed his cock in your asshole, you tighten around him as you feel every inch and vein of his cock. "Mhm!" You whimper out through his underwear as he pulls out just to thrust back in roughly, he pushes your face against the car window so everyone in the parking lot can see you.

"F-Faster!" You whimper out as he thrusts back and forth into your hole, his grip on your hips tightens as he nears his release wanting you to cum before he does. He constantly hits your g-spot causing you to release yourself all over the car door as your body is pressed against it, once you release your hole tightens around him causing him to blow his load inside your hole. Dean collapses against your body as the windows are fogged up, "fuck baby.." He whispers in your ear as he pulls you away from the window and into a hug.

sorry that this fic isn't longer, BUT happy Halloween! 🎃

taglist - @starboye @mailmango @ghostking4m @kingchaospostsstuff @crispysoup318 @inhumanshadows @its-ares @gayaristocrat @cronaaaaaaa @irlsamcarpenter

[mggsv]

Diner Boy

m!reader x dean winchester (18+)

summary: he’s a regular, comes often but there’s never really a pattern. he sits with his brother, Sam, you learned. sometimes they’re smiling and having a good time, other times they look like they’ve just fought, but no matter what- they always sit together, and today you’ve caught his eye- Dean.

warnings: car sex, hair pulling, overstimulation

“He’s staring at you…” Your work friend, Charlie, had said. You were standing at the counter sorting the tickets. It wasn’t a busy day, but it wasn’t slow either. It kept you both working, with plenty time to talk. You gave her a small look before scoffing, “You say this almost everyday Char.”

“Well yes, but, Sam and Dean don’t come here everyday.” You catch her eye as she motioned over to the table she just came from not too long ago. “You are very pretty..you get mistaken for a girl often-“

“I don’t want to talk about that. And besides,” you pick up a tray of food, fit for another table, “I’m sure they’re staring at you, you just like girls and don’t take interest.” You give her a wink while she starts to giggle.

It was true, though. He was staring at you. Your beautiful frame, your curly hair fanning around your face, your perfect lips that pulled into a smile whenever you interacted with the tables to catered to for the night. Dean was watching, and you felt his gaze.

You could hardly work. His eyes made your legs week, and your pants tight. You felt hot but there was no sweat. Your hands shook while taking orders. You knew what you wanted, what your body screamed at you to take before the chance of a lifetime slipped away.

Your shift ended roughly at 10. You’re tired, body aching. You take off your apron before saying your goodbye’s to your coworkers. Charlie had left an hour before. It was raining outside, it made you groan. As much as you loved the rain, you walked to work, and walking in the rain meant an umbrella you didn’t have. “Need a lift?” you hear a voice behind you, a familiar one at that, his voice. Dean. You hear yourself chuckle, turning around to look at his tall frame. “No.”

“No? It’s raining like hell out here and you have no umbrella, and you say “no”?” He’s leaning against the glass frame of the wall. He bore a small grin, but those eyes..those eyes said so much more. You felt it. They trailed your body down to your hips, and rested before making their way back up to your eyes.

“Yeah.” you cleared your throat. “And if you’re done..” you look away, staring at the rain pour harder. The droplets beginning to splash against your legs and his boots. Dean moves closer, the soft clack of his shoes perfectly in sync with the rain. Where was Sam, you had wondered. “Do you..need a ride?” He asked again, lowly, fit only for you.

“…yes.”

the walk back to Dean’s beautiful car felt like forever. He shielded you from the rain, his brown leather jacket over your frame. His arm wrapped around your shoulder securely like you were the most precious thing in the world at that moment, protected..

“ha….ha fuck.” Your hand was lost into his short locs of hair, gripping on what you could. You breathed heavily into the small space of Baby’s backseat, suffocated. Dean held your waist, cock disappearing into your hole for what seemed like the hundredth time this night. His teeth sank into his bottom lip, sweaty forehead rested against your shoulder. “Dean..” you moan.

He shuddered, bottoming out inside of you. Your cock leaked against his stomach. You were so closed it rubbed just up against it in the right of ways. Your breathes came to a shuddering halt. Your heart seemed to drop into your stomach, and a clean wash fell over you. Your hands found their way to Deans shoulder, squeezing as you rode out another orgasm, your seed shooting lazily across you and Dean’s stomach. “You feel so good baby..” He groans. His hands tightened the grip onto your waist. While your body relaxed against his own, he sped up. Your body moved quickly against Dean’s thick cock. “So fuckin’ good.”

Your body rolled against his. Your legs felt tight, you tried your best but your body shook to its core. “Dean-“ You gasp, nails digging into his shoulder. He hit that spot inside of you so well…You couldn’t help the helpless whimper falling from your lips. “Almost there.” Dean grunts, failing to notice Sam’s name flash across his buzzing phone.

[supercap2319]

Dean: *Smiles charmingly* "You know, Y/N. You should go out with a real man."

Y/N: *Looks at him and smiles* "Sure. Do you know one?"

Sam: *Laughing in the corner*

[m4nspr34d]

BUT DADDY I LOVE HIM

Dean Winchester x M!reader

Warnings: Fluff, Angst, After sex, star crossed lovers.

Summary: Your relationship with Dean has been under wraps from the day you had met, struggling to come to terms with the fact you would be shun by your already displeased parents for sneaking around with a ‘Vigilante’ such as himself.

You fingers tapped at your computer, your headphones blasting the heavy bass of your music in your ears. It was another late night, your parents had turned in hours ago, all that was left for you to do was finish your essay and finally get to bed yourself.

The table shook as your phone vibrated, looking down to see Dean’s caller ID. Your music paused, your hands tipping your headphones onto your neck. “Hey, you.” His voice said over the phone, the distant sounds of cars passing over the phone. “Hey, you okay? It’s late, Dean.”

“Cant I call my boyfriend?” His voice said, that teasing town he always used, god. “Never said that. just— you never call at this time.” You said, chuckling as you took your headphones off, leaning back into the chair as the phone held close to your ear. “Yes I do!” He was defensive, you could just imagine the sour look on his face as he said it. “Not unless you’re up to something.” You added, amused to see where he was going with this.

“True.. look outside.” He said, bluntly, an almost defeated tone coating his voice. Your head fell back as a laugh escaped your lips, predictable. You stood up from your chair, walking to the window, not surprised to see Dean out in your front lawn, leaning against the lamppost, the phone held to his ear as he smirked. “Cute guy in my lawn, think you can give me five?” You teased as you leaned down onto the interior ledge, his scoff over the phone paring perfectly as his eyes fell to the ground for a moment, his head lifting again to look at you. “Need some company?” “Always.” You didn’t even have to think of the response, quick to hang up the phone, opening the window just enough for Dean to be able to lift it from outside.

You sat back into your bed, grinning to yourself as you waited, feeling like a teenager again, it had been a long time since Dean had to sneak in, only that your parents had caught on to what you were doing when you came back on the weekends, upping their security on you a bit. Your face lit up as you watched him appear in the window, a smirk on his face as he slowly opened it, carefully climbing inside and finding his footing. He was quick to step to you, you doing the same. His arms snaked around your waist, pulling you close to him, the smell of his cologne like a drug, the way he looked down at you with such compassion, such true and unequivocal love.

“I missed you.” He let his neck fall to you, nibbling at your ear playfully as you felt his lips pull into that damn smirk. “I missed you too.” You replied, your hands sliding up and down his arms. His head lifted once again to meet your eyes. “It’s my dad, you know how he is.. he just— he doesn’t want us to be a thing, he thinks you’ll corrupt me or something.” You said, a slight giggle passing as your hand reached to his head, your finger brushing through his short hair, your gaze moving between his beautiful; so, so beautiful— eyes, and the movement of his hair beneath the caressing of your fingertips. “Bit late now.” He said, his hand cupping your cheek, his thumb brushing beneath your eye.

you both started to giggle, your hands pressing against Dean’s mouth, your eyes widening as you desperately tried to suppress the laughter. His body pushed towards you. His hands pressed against your hips, firm but soft, setting you down onto the bed.

Your head rested against his bare chest, both of you at your most venerable, your hand lay adjacent to your face, your fingertips barely moving as you gave him any notion that he had every bit of your attention. “Y’know, we could just run away.” He broke the silence. You giggled at his remark, silly; but true. “You know I cant.” It wasn’t the first time he had entertained this silly fantasy, you two running away with Baby, living off diner food, motel after motel; much less glamorous than he seemed to think. “Yeah.. Yeah I do.” He said, looking down, pressing his lips into the side of your forehead.

“I have a life Dean, I have so much.. I cant throw it all away, I mean— Stanford? I worked so hard for it all, I can’t do that.. I just can’t.” Your voice was much softer than before, the playful banter only lasting for so long before the two of you had to bare the truth right in the eyes. “You could work at the shop, with me.” His head lifted from the side of yours, tilting to meet your gaze in his. “I know shit about cars.” “I’ll teach you.” It was tiring, you were both so different, such different backgrounds— yet, you both yearned for the one thing: eachother. A sigh tipped off your bottom lip, adjusting your head to ease the strain on him. “One year, then i’m outta here, we can settle down together, get a place, maybe a dog— or a fish, we’ll see how you clean up behind closed doors.” Your tone fell softer, a light chuckle hiding behind each word, but it didn’t take away from the clearly pained smile he flashed.

“I’d give it up for you— all of it, I don’t expect you to do it for me, you’ll be better than I am. I just don’t want you to outgrow me when you’re a big fancy guy in a penthouse.” “You know I wont.” “No, I don’t.” It hurt, truly it did, but that was how it worked. No matter how much you both lied to yourself, there was only so much of this sneaking around before it got tiresome, the closest thing to a date being sharing a few beers on your roof. “I don’t love you like the rest, you’re different, and I know I don’t have to be the one to say that for you to believe it.” Your attention peaked, propping yourself further up his chest, your cheek resting as you kept your jaw lifted to keep within his gaze. You hated having this conversation, sometimes you wish you could block out all the sad, the hurt, but, that’s just how it was. “I really do love you.” Those words meant everything to you, they always did, the way he said it at all the right times, it was never a one and done, it was a rare occasion, you knew he meant it— you knew he always did. “I know.. I know. I love you too.” Your fingers trailed up, passing his collarbones as you took the pendant of the necklace in between your fingers.

“Just let me talk to him, have lunch, i’ll sort it out, I swear.” His voice was so desperate, the way you could tell how bad he wanted this, how bad he needed it. “It’s better this way.” “Is it?” Silence, again. It was so hard balancing your own well-being with your family; your blood, and the man you genuinely saw yourself growing old with. “It doesn’t matter what we do, he won’t change his mind, I don’t want that to weigh on us.” Ignorance was bliss, whatever you didn’t know, couldn’t hurt you. a a kiss pressed against your forehead, his hand firm against your nape, his thumb gently rubbing back and forth along the skin beneath your earlobe. “Stay until I fall asleep?” Your eyes lifted, looking up as he flashed you a smile, nodding as his eyes closed for a moment. Your head pressed against his chest once more, your eyes fluttering as you drifted, the sound of his heart beating soothing you, the reassurance you needed, the kind that let you know how close he was, how he was always gonna be your shoulder to lie on.

Thump.

Thump.

Thump..

Thump..

Dividers: @cafekitsune Thought I’d start off with something short and sweet as I’m still getting my footing on here, any tips and criticism are welcome and appreceated. 🌹

[bigfan-fanfic]

Got A Problem With That? (Male!Reader x Dean Winchester)

@innerpiratefun Can you make a part 2 of Dean Winchester x Male Reader he's a mechanic in California, it's my favorite fic also could you include a part where Sam realizes the collar and says something to dean but dean doesn't take it off or something like that, btw love your fics

Here's PART 1

"He's good at that stuff. Maybe better than you." Dean smirks at his little brother.

Sam scoffs. Skeptical.

Dean chuckles, turning up the music.

They've left you back at the motel - there's no way you're letting Dean travel off alone for this journey, but you're also not skilled in monster hunting, so you've made yourself useful through research.

You're currently compiling a little database on monsters through research and the brothers' anecdotes.

You're not very happy about being dragged into a search for John Winchester, but you want to support Dean, who seems to have genuinely missed his brother.

Besides, apparently Sam tried to leave, but was driven into a deeper need for vengeance when his girlfriend was killed in the same way as their mom.

"You're pretty, ah, serious with him, yeah?" Sam asks again. In the two weeks since you started traveling together, Sam has asked this quite a few times.

"Yeah." Dean responds shortly - as he has each time. He knows their dad might be weird about it. Knows he and Sam weren't exactly raised to even know about sexuality besides heterosexuality.

They both know things, but it's still... awkward to see each other after so long and have to share that.

Dean's been wearing a leather jacket and many layers - trying a little harder not to let his collar show.

It's technically just a necklace, but it serves the same purpose.

You have a thicker leather one for play, but for just wearing, it's a black chain of twisted links attached to a black circle. It's not particularly noticeable, but it is distinctive.

"So... what's this?" Sam asks, reaching out and pointing at the necklace.

Dean tenses as if about to smack Sam's hand away, as if thinking he was going to touch the necklace. "Y/N gave it to me."

"Oh. It's... nice."

"Thanks."

Sam clears his throat, uncomfortable. "Looks kinda like a BDSM thing."

Dean winces. And that tells Sam all he needs to know.

He chuckles a little. "Wow, Dean."

"Shut up." Dean growls. He's not laughing.

"Jeez..." Sam smirks, happy to get under his skin. "I was just-"

"It's something special to my partner and me. That's all you need to know. And all I feel like telling you. Got it?"

"Okay."

The drive is unbearably awkward, especially on the way to take down another spirit.

"Dean?" Sam asks as they park.

"Yeah?" Dean asks gruffly.

"I'm... I'm happy you're that close with someone. I wanted to have what you have with... with Jess."

Dean shifts uncomfortably. But he doesn't protest or shy away - you've helped him learn to communicate and part of that is listening.

"So yeah. It's really cool that you have a partner you're so close to. You're a lot less of a douche than you were." Sam chuckles.

"Yeah. Th-thanks."

"Jerk."

"Bitch."

Sam makes to open his door. "How'd you pull a guy so much smarter than you, anyway?"

They leave the car, already more relaxed.

"Yeah, well, it's actually a funny story..."

[sweetcocopowder]

Could i have a demon dean fic with the prompts "Are you afraid of me?" And "Take it off" with a male reader please

Prompt 6 | Crossroads Demon!Dean x Male! Reader

Synopsis: You finally bring yourself to summon a crossroads demon to strike a deal. But you quickly find out that this crossroads demon does things a lil differently to seal a deal.

Word Count: 3.7K

Warnings: Smut. Tongue fucking. Size kink. Dean's a big boy. Reader's short. Praise. If i miss anything, please tell me. It's late at night.

Notes: I am so sorry that this took forever to post. This is probably the longest fic for the Milestone. I wanted to get it right since these types of prompts take me forever to write. But, I hope your enjoy hehe

You can’t get your breathing under control. It comes short and shallow that it makes your head dizzy and light. It actually worked. The ritual actually worked. You stumble backwards, your feet catching against each other on the loose gravel as you fall on your ass. So much for first impressions.

The demon stands tall in the middle of the crossroads clad in a pitch black suit. He sweeps a hand through his blonde hair, trying to tame it but some strands still fall over his freckled face. His black eyes scan over his surroundings before they flicker to an intoxicating green. They set upon you, a frown forming deep upon his features.

“You’re a little pipsqueak now aren’t you,” the crossroad’s demon comments.

At that, you’re quick to your feet, dusting yourself off as thoroughly as you can. You puff out your chest and square your shoulders, because you’re in charge. You’re the one that summoned this demon. You’re the one making the deal. How dare he call you that when you’re the only offering him something in return.

“Don’t call me that,” you snap at him, but your voice comes out cracked.

The demon chuckles, a set of fangs showing from behind his lips. He walks towards you, and you quickly realize just how much taller he is than you. You’re short for a man, only coming up to a 5’5. And standing next to someone over 6 feet is always something.

“I can call you whatever I damn well please,” the demon snaps.

You flinch slightly, brows furrowing in anger at the mouth on this hellish creature. He may not have any horns. Or no tail. Or any hooves in those dress shoes he wears. But he sure as hell smells like a demon. Sulphur at its finest.

“I’m here to make a deal,” you get back onto topic, the reason why you even summoned him here in the first place.

The demon rolls his eyes. “Yes, yes. I know why you’re here. Didn’t summon me for a chit chat now did you?”

He pinches your chin between his thumb and pointer, inspecting you. He moves your head back and forth, looking over every inch of you. You swat his hand away at the feeling of your cheeks flushing something hot.

“Is it money you want? You want your girlfriend to love you? Want a promotion at your job you’ve been stuck in for eight years? Or want your boss dead?” The demon lists off on his clawed fingers.

“What!? No!” You bark out.

“A new car? Your partner to be pregnant?” The demon asks a few more things. “I can do that myself if you want. If you’re the one shooting blanks then you’ve come to the right person. Probably the straightest and strongest shooter you’ve met!” He chuckles loudly.

“No! What are you going on about?”

The demon laughs harder, the noise seeming loud out in the open, deserted road. “Then what is it you want, pipsqueak?”

You ignore the comment. “I want to be six foot tall,” you answer with as much confidence as you can muster.

The demon goes silent. He stares at you with wide eyes, as if you’re pulling his demonic leg. But when you stand there in silence, not speaking a punch line, it settles into the demon that you aren’t joking.

As much as you’d like to be joking, you’re not. You’re sick and tired of people belittling you because of how short you are. Treating you like a child even though you’re a grown ass man. It’s humiliating at some points. And this demon is just showing you that it’s all true.

How will you explain it when you come back to your boring office job six feet tall? You’ll get to that afterwards.

“So,” the demon clears his throat. “You want to sell you soul to be six feet tall? Am I correct?” He asks bluntly, gesturing his hands around as he speaks.

You nod with a, “Yes.”

The demon pops a hip out with a hand placed over it. You watch the motion before dragging your eyes back up. You’d be a fool to admit the demon before you isn’t hot. You wonder if this is what he looked like before he became a demon. How does becoming a demon even work?

The demon shrugs. “Well I guess I know people that have done worse.” He sighs. “Do you know how a crossroads deal is made?” The demon asks with a cocked eyebrow. He makes his way towards you again, reaching out and patting down your tie.

“Yes. A kiss to seal to deal,” you say with confidence.

Just a simple kiss.

“I do things differently,” he says as he hooks a finger into the tie.  

“What?” You utter out weakly before you can control yourself.

With the smell of burning fabric, the fabric touching the demon’s finger burns a neat line. It falls off, flopping to the ground. His green eyes land on you and you find yourself unable to speak. A hand hooks into your belt and you stiffen up greatly, your face burning a bright red once again.

“My deals are struck a lil’ more intimately. A little more hands on,” the demon grins, his lips only mere inches away from yours.

You can smell the demon better than before now. The smell of sulphur still lingers, but there’s something else that lingers. Something much sweeter. It’s not a pleasant combination of smells though. But what else did you expect a demon to smell like. Rainbows and unicorns?

But you know what the demon is talking about. You summoned a cross roads demon. Not a fucking succubus.

Yet at the same time, you don’t want to have to do the entire ritual again just to get an ugly demon. It would be a shame to pass up on an opportunity like this. Yes? Maybe you are a little messed up in the head. But those green, green eyes. You can’t seem to look away from them.

“Do you still want to be six foot tall?” The demon all but growls out right in your ear.

You swallow thickly. What harm could getting fucked by a demon to be a little bit taller do? You’re just selling your soul.

“Y-yes,” you utter out.

The grin that spreads across the demon’s face is devious. “Are you afraid of me?” He asks, his voice low and even.

It goes straight to your crotch though. You’ve never had anyone come onto you like this but you’re quickly realizing you might be more into it than you may have first realized. You swallow thickly, not being able to look away from the demon’s piercing gaze.

“No,” you squeak out.

The crossroads demon takes a large step away from you with a hearty laugh spilling from his lips. You’re confused. You can’t help but stand there dumbstruck at the sudden change. With the demon’s back turned, you quickly adjust yourself in your suit pants. Don’t tell yourself that he was joking?

The demon turns back around to you, his eyes looking you up and down as if you’re a piece of meat. You can’t help but step from one foot to the other under the watchful, dark gaze.

“Take it off,” the demon suddenly says.

“W-what?” You utter.

“I said,” the demon makes his way back towards you, placing a finger on your chest. “Take this fucking suit off or otherwise you’ll be walking home in nothing but your birthday suit.”

Oh. Oh. Oh my lord. You can feel yourself become as bright as a tomato and yet, you follow the command instantly. You begin stripping, starting with your coat and button up, then to kicking off your shoes. With only a split second of hesitant, you take off your suit pants and hesitate at your underwear. You look to the demon before you who only cocks an eyebrow your way. You swallow thickly again, butterflies coming to your chest as you strip everything. You cover yourself subconsciously with your hands in front of yourself, trying to hide your bulge.

You flinch at the warm hand splayed across your chest suddenly. You can’t drag your eyes away from the crossroads demon. He licks his lips in anticipation, liking what he sees before him.

His hand glides up your neck to the back of your hair, gripping in to tug your face upwards to him. He’s so much taller than you it’s almost intoxicating. You’re almost standing on your toes as he comes down for a kiss, capturing your lips with teeth and tongue. You can’t help but moan into the kiss as the demon grabs onto your sides tightly. His sharp nails dig into your soft skin causing a harsh shiver to run down your naked back.

The demon pulls away, looking down at you with devious green eyes. A string of saliva connects your flush lips to his and all you find yourself doing is staring.

“Now,” the demon purrs, “Did you want to take this on the hard gravel or do you want to try and stand and take it?” He asks lowly.

You swallow thickly, thinking it over. The thought of your back or stomach getting scuffed up doesn’t sound all that pleasant in your eyes.

“I’ll be alright standing,” you say, a slight shake in your voice.

The demon shrugs with a cocky expression on his face. “Alright,” he mumbles, “It’s your deal.”

He then drop to his knees in the loose gravel, his eyes never leaving yours. He grabs onto your thighs and spins you around. Definitely not the direction you thought this was heading, but you don’t complain otherwise. You can’t help the shaky exhale that leaves your lips at the sudden direction this is turning. This is not what you thought would be happening tonight, but you can’t remember the last time you were properly laid. So may as well take this as it is.

Large hands spread your cheeks open and you suddenly feel very, very exposed. You try and hold back the whimper that tries to escapes your throat as hot breath touches your skin. You bite down on your knuckles as you bend over just a little, giving the demon a better look.

“I’m gonna loosen you up a bit,” you hear the grin on the demon’s voice, his face buried under you. “Don’t want this to be unpleasant is all. May be a demon but I’m not a monster.”

“Who would hav- AH!”

You don’t get much warming than that before a hot tongue licks from the base of your balls all the way to your hole. You shiver violently at the feeling. Does his tongue feel much stickier and thicker than a normal humans or is that just your imagination? He licks a long strip from your balls to your ass again, this time slower than the last. And this time you can’t help the sound that comes from your mouth. You place both of your hands on your knees with your head bowed between your shoulders. This might be a little harder than you thought.

“Don’t hold back, pipsqueak. I love hearing those beautiful noises,” the demon says huskily. “It’s like a reward.”

You go to say something, but everything and anything you were going to do is thrown away as a thick tongue is pushed past the tight rim of your ass. You let out a startled cry at the odd sensation of the hot, sticky tongue within you. It’s as thick as at least three fingers and feels longer than such. It prods and seeps deeper within you, as if searching for something. It stretches you oddly, the strange feeling earning a whimpered moan from your lips.

You bend over a little more, fisting your hands on your knees as they begin to shake. You shudder an exhale as the demon’s tongue curls within you, folding on top of itself to make itself thicker before coiling back out. This is not what you had in mind, but you must admit it does feel amazing. If he keeps this up, you might have to take it to the gravel because your legs might just give way.

You can’t help but keen and gasp at the warm tongue prodding and pushing against your prostate. Your legs shake as it only feels like he goes deeper, and deeper. A sheen of sweat starts to cover your skin that’s quickly cooled in the cold night air.

Your cock sits half hard between your legs, but it wouldn’t take much more to get yourself to full length. You wrap a hand around your cock, giving yourself a few dry strokes. You can’t help the groans and whines that slip through your parted lips as the demon seems content in eating you out for the time being.

After another minute of prodding and twisting, you feel yourself already coming close. This is all so new and blissful that you can’t help yourself. You’re coming in your hand before you even know it. You gasp and groan, clenching your jaw as the tongue retracts from within you. A little shame rids into your gut, but the satisfaction out weights it for now.

A dark chuckle comes from behind you, “You lasted a little longer than some of the other fellas that come to me.”

“Nice to know,” you pant out.

You don’t think you can stand much longer. You return your hands to your knees, trying to catch your breath.

“But we ain’t done, pipsqueak,” the demon rumbles as he stands to his feet.

You peer over your shoulder with wide eyes to catch the demon wiping his mouth with the back of his sleeve. His blonde hair is ruffled, and those green eyes only watch you with a hunger that’s on the verge of starving.

“Deal isn’t struck until I come in you,” he says bluntly.

“W-what?” You stutter.

The demon leans into your back, wrapping his arms around your middle and hooking his chin on top of your head. He engulfs you fully, holding on tight so that you can’t leave. He leans down and breathes into your ear, and you can’t help but freeze up and become ridged.

He speaks slower and gruffer this time, his voice rough in your ear, “I’m going to fuck you until you come again from just my cock. And nothing else. And then I’m going to fill you up so that you, a little pipsqueak like yourself can become nice and tall to impress everyone around you.”

Goosebumps run across your cool skin at the thought of such. You’ve never had anyone talk to you like this. You’ve never let anyone talk to you like this, but oh my do you like it a little bit too much. The rough words go straight to your soft cock, making it twitch.

“Do you want me to do that?” The demon asks as one of his hands slides back around to your ass, giving the soft flesh a squeeze. “Can you do that for me? Hmm?”

You breath out shakily, “Y-yes, please.”

You can feel him grin again against your neck before giving your flushed skin a kiss. He moves away but just enough so that he can undo his belt. The clinking of the buckle is loud on the open road, and you suddenly become very aware of where you are. You glance around at the empty fields that surround the gravel crossroads. No one comes down here and you bloody hope that no one decides to spontaneously come down a deserted road. But all of that is quickly washed away as a thumb prods into your saliva slicked ass. You grit your teeth at the wet sound and the feel of the cool saliva running down your legs.

The demon hums behind you, almost satisfied with what he’s inspecting. “I think I over did it a little, but you’ll be perfect all the same.”

The thumb disappears to only be replaced by the warmth of the demon’s cock. From what you can feel, he’s big. You can’t help but tense up as you suddenly over think everything. But a hand comes around your front, resting over your heart.

“Oh my,” the demon hums. “Now now, that won’t do. Relaaax, pipsqueak. I ain’t going to do this if you don’t want to. It’s your deal after all.”

The statement does in fact calm you down. You’re here to make a deal. He may be a demon, but he hasn’t hurt you as of yet. Which is reassuring to you right now.

“L-Let’s seal the deal,” you shakily utter out. Not out of fear, but more anticipation and need.

A low chuckle in your ear has your soft dick twitching. The demon pushes past the rim of your ass, the head of his girthy cock slipping in easily. You gasp loudly as he pushes in a little further before pulling out and slamming his hips flush against your ass. He bottom’s out quickly, the entire length of his dick sitting snuggling inside of you. He worked you open well enough to do so, a deep chuckle emitting from his flushed lips. He curves in just the right way that hits against your prostate almost perfectly. The way that has your knees becoming weak and leaves you breathless. He stretches you a little painfully, more so than his tongue but you find yourself only wanting more. The pleasure that courses through your gut fizzles your head and you find yourself not thinking straight.

The demon begins a quick pace, using the hand on your chest to keep you in position as he thrusts into you. He more or less towers over you, being able to hold you up if your legs decided they didn’t want to support you any longer.

The noises that comes from your mouth are ones of pure bliss. You don’t know where to put your hands and after a while you end up placing a one on top of the demon’s on your chest. He chuckles at that, low and deep into the nape of your neck before grabbing a hold of both of your wrists. He crosses your arms in front of your chest, holding onto you tightly as he pounds his hips into your ass. The wet plap of the demon’s hips is numbed out by just how loud you are. You whine and keen and moan with every thrust and every inch he gives you.

You try to catch your breath but every time it’s knocked out of you with each thrust. You’re unable to keep yourself quiet at the closeness and the fulfilment of the demon. He breathes into your neck, mouthing words and kisses into your sweaty skin. Your once soft dick now bounces between your legs half hard. You don’t think you could handle anything touching your dick at the moment. Everything buzzes and trembles in all the right ways.

“You’re probably the best one yet,” the demon grins in your ear. “Taking my cock like a good lil’ boy.”

The praise makes you feel high. You get lost in everything, the constant stretch and pull of the demon pounding without tiredness into your ass. You hunch over, allowing better access for the demon and he follows you. Towering over you, holding you close to his chest. Engulfed in his arms that could wrap around your entirely.

You come a second time, this time being much harsher than the first. You forget how to breath and forget where you are for a second. The demon lets up. Even when you’ve tightened around him, it only makes his movements even more driven. He pumps once, twice before driving his cock deep within you. The warm sensation of him filling you makes your entire body shudder. Makes your dick twitch, expelling a little more cum before once again softening between your legs.

Your legs tremble and shake and if it weren’t for the demon holding onto you, you would have fallen on your face by now in the gravel. You breath heavily, trying to catch your breath as the demon makes sure every last drop of him is expelled inside of you. Sealing the deal.

He pulls out and you whine at the sudden loss. It’s a pathetic noise that you can’t stop. You never knew you could make so many noises until tonight. Nothing that has ever been drawn from you before. And find yourself having loved every moment.

“Can you stand?” The demon chuckles.

You lick your lips and swallow thickly. After a while, you nod sharply as you drag your feet under you. The demon lets you go but keeps his hands on you, afraid you may fall to your knees. But you don’t, you shake a little, but you stand all the same.

You can feel the demon’s cum drippling down your leg and you already know it’s going to be a fun five hour drive home. You might have to grab a motel because five hours sounds like five days right now.

When you turn to face the demon, you now stand eye to eye with his green gaze. He grins from ear to ear with a cocked eyebrow. The deal has been struck.

You don’t feel any different, but the ground does now look as if it’s further away. You’ve gotten your extra inches. Just like that.

“Th-thank you,” you manage to get out.

This makes the crossroads demon laugh, covering his mouth with a hand. Crow’s feet scratch at the corner of his eyes. He points to you with a toothy smile.

“You know, if you ever want to make another deal, call on me personally,” the demon chuckles deeply, “This was fun.”

That, actually sounds like a good idea. You work in an office. You’re digging yourself an early grave anyways.

“And how should I-“ you have to lick your lips, your entire mouth dry. “How should I do that?” You ask.

“Dean,” the demon finally greets himself. “The name’s Dean.”

-

:)

[l1tw1ck]

Not a Suspect

Bottom!Dean x Top!Male Reader

☆ Word Count: 1,292 ☆

probably ooc/plot dependent, I haven't watched in a while 😭

CW: Non-Con, First Time Bottoming, Anal Fingering, Humiliation, Overstimulation, Semi Rough Sex, Blood Mention, Daddy Kink, Creampie

“What the hell do you think you're doing?” Your hand is pressed against Dean’s neck, his back against the wall. You lifted him a few inches in the air in order to meet your eyes. You caught him snooping around your room.

“I- I thought this was my uncle’s house!” He smiles sheepishly. You're so much stronger than he is, he wasn't expecting to be put in a chokehold. “The door was unlocked so—”

“Save it. I’ve seen you and that other guy hanging around town snooping for information about that incident. You must think I’m a criminal, huh?”

“That's not the case, sir, I um—”

“Did you come to that conclusion after you searched my things?” You click your tongue then look him up and down. “I’ll let this slide though. As long as you make it up to me.”

“I uh, I have forty dollars-”

“Hmm.” You place him on the ground and turn him around. You grab his wallet from his back pocket and find an ID. Your old jobs gave you the skill of knowing what's fake and what's real. “Of course. I knew you weren't a real detective.” You laugh.

“I’m an undercover investigator!”

“Uh huh.” You find a secret pocket and find his real ID. “There we go. Dean Winchester.”

Dean’s ears burn red. He can't believe he's in this situation and that he can't fight back, something about this is making him feel timid. Sam warned him not to do this but he didn't think he'd feel so helpless against you. He’s fought much stronger and scarier creatures than you but it's different when it comes to humans. You can't figure out their motives so easily.

You drop his wallet and lean over, unbuckling his belt then forcefully pulling his pants down. “Hey! What are you doing?!” He flails around defiantly.

“Stop moving.” You use his belt to tie his wrists together.

“I’m not gay!”

“You really think I care, sweetheart?” You pull down his boxers. “Besides, I’m sure you’ll enjoy yourself.” You spread his ass open and spit on his rim before forcefully shoving a finger inside him.

“Fuck!” He cries out. “Stop!”

You chuckle. “I know your type. You gag at the mere idea of having sex with another guy.” You force another finger inside him and start stretching him out. “Then, once you do, you love it like the little slut you really are. Trust me.”

His entire face is red with humiliation. “You're wrong.”

“We’ll see about that.” You find his prostate. Dean moans, his knees buckling. If it weren't for your hand on his waist, he’d probably fall. “There it is.” You say gently, your husky voice making him feel strange. You continue to prod at his prostate, reveling in his strained whimpers. He’s trying so hard not to make a sound. He clenches his fists and aggressively bites down on his lip as you continue to pleasure him, although he doesn't want to admit that.

He will admit that it hurts. A lot. Dean rests his forehead on the wall. He hates how good it feels despite everything, your thick fingers stretch him out so well. His face is so hot it feels like he has a fever. “Ah–” Dean gasps. “No- no—” He shuts his eyes tightly and lets out a muffled moan as he comes, splattering the wall with his cum.

“Good boy~” You praise him, slowly sliding your fingers out. It feels like Dean’s head is going to explode. “I’m a little too impatient to keep going.”

Dean gulps at the sound of your belt falling to the ground and your fly being unzipped. There's nothing he can do to stop you. You take out your hard length and press the tip against his rim. You lick your lips and begin to force yourself inside. “You're tight, baby.” You groan, pressing your chin on his shoulder. His palms begin to bleed from how tightly he's clenching his fists, it's too painful for him.

“Fuck—” He breathes out. You're big.

“It hurts, doesn't it?” You coo, reaching out for his weeping cock. “Let me help you.”

Dean moans as you begin to roughly stroke his dick. “Sto- stop–” A single tear runs down his cheek. You're reaching so far inside him. He rolls his eyes back as you bring him closer to his climax.

“It’s all in, baby.” You bottom out. “How’s it feel?”

“It fucking hurts–” He hisses, more tears running down his cheeks. “You bastard– ah~!” He comes once again.

“You're cute when you whine.” You slowly pull back then shove your cock back inside. Dean rolls his eyes back and lets out a slutty sounding moan. You grin and start thrusting in and out of him at a steady pace. You look at his beat red face, his mouth remaining open to let out his pathetic moans. “‘S good, isn't it?”

Dean shakes his head despite his body betraying him. “No- No~!”

“You're not good at lying.” You place your hand on his throat, lifting his head up. “Admit it. You like getting fucked.”

He bites down on his lip and rips a bit of skin, blood trickling down. You lean in closer and lick up his blood. “You like how Daddy spreads open your tight hole, don't you, baby?”

He lets out a muffled whimper, his cock weakly spurting out another rope of cum.

You chuckle. “I know I’m right.” You let go of his neck and stroke his dick again. “You’re just a pretty little cock whore.”

“Nnh- No-” He moans. Dean is well aware of the fact that his lies are completely unbelievable. He doesn't want to like this at all.

“Yeah? You really think you're not? You think you're not into this?” You laugh again. “No, Dean, you're a slut who loves taking cock. You love how it feels to have a cock in your ass. Admit it.”

“I don't- I don-” He pauses, drool spilling from his lips as you stroke his sensitive cock.

“Be honest, slut.” You rub the tip of his length with your thumb. Dean has another orgasm. He…He really does like it.

He whimpers adorably. “Don't…Don’t stop.”

“That’s what I thought.” You say smugly, smirking. He shivers. You let go of his poor length and pull out. You turn him around and lift him up by his thighs, pushing his back against the wall. He looks at you in embarrassment as you slide your length back inside him and roughly fuck him.

Dean moans more freely than before, his eyelashes fluttering like a hand fan. He wraps his arms around you for stability. “Fuck~! Wai- wait~!” He gasps.

“I can't control myself, your cunt feels too fucking good.”

He mewls. You lean in and sloppily make out with him. You’re driving him insane. You slide your hand up underneath his shirt and rub your thumb against his nipple. He moans into your mouth. His nipples have always been sensitive but it feels even better in this situation.

You pull away and let out a groan. “Gonna come, sweetheart, right in this tight ass of yours.”

“Mmh- yes~” Dean really feels like a slut now. You were right.

You chuckle and let out a low sound of pleasure as your thrusts slow to a halt, your cock spurting hot ropes of cum into his cunt. “There you go, getting your ass stuffed is a much better job for you.” You pull out and drop him onto your bed. “Should I call you a cab?”

He shakes his head. He doesn't want to leave. “Can I stay?”

You chuckle. “Sure. And you know what? I know a few things about that incident you're looking into.”

[mlmxreader]

You're The Only Hell Your Mama Ever Raised | Dean Winchester x m!reader [NSFW/MDNI]

『••✎••』

↳ ❝ You're The Only Hell Your Mama Ever Raised, Warrant with dean Winchester please? ❞

: ̗̀➛ After ten years of living with Bobby, you decided to join the Winchester brothers with hunting; four years later, things between you and Dean start to get a little more complicated than just hunting partners.

trigger warnings: ̗̀➛ alcohol consumption, praise kink, swearing, blowjobs, cum swallowing

↳ word count: 1545

•───────────────★•♛•★──────────────•

It was such a vivid memory that you could hear Bobby talking in the twilight hours of the night, hushed tone and grumbling with every other sentence, almost as if he had ever regretted taking you under his wing the same way that Rufus had; they were the closest thing that you had to parents, and with Rufus halfway across the country working on a case, it was down to Bobby to keep an eye on you.

But you couldn’t tell who he was talking to, you couldn’t hear who was on the other send of that fucking phone, but you figured that it was likely to be either Rufus or John Winchester - an old friend of his who had a little bit of trouble with his own boys, the youngest of which was the same age as you. 

“It’s time that boy was shippin’ out,” Bobby grumbled, and you knew without seeing him that he was shaking his head and stressing himself out. “And I mean come hell or high water. He’s old enough now, he should be in his own home with a good damn job. Not still bouncing between my place and Rufus’ place… set him up with Dean and Sam? Are you stupid? He isn’t a hunter!”

You waited for the inevitable as you scratched the side of your neck and chewed at the inside of your lip, not really sure how to react to such a suggestion yourself; you had known Dean and Sam since you were kids, but it was different now you were all grown up.

You hadn’t seen them for years, and there was no doubt in your mind that they had changed a lot more than you ever did.

“He smokes and spits and drinks and fights, sure,” Bobby scoffed. “But that’s on me - I let him get away with it and don’t tell him off properly… yeah, no, no, his friends do all look like trouble - but I wouldn’t expect anythin’ less… no, he sleeps pretty much all day and he’s never around at night - you’d think he was a vamp til you saw his teeth… I just… where’s the boy I used to cuddle? He was so little, and such a nice kid… where’d I go wrong?”

You wanted to go down and reassure him that it wasn’t his fault how you turned out; Bobby and Rufus did everything for you, they never gave up on you no matter what you were like.

You could understand why he was so frustrated, but you didn’t want him to sit there blaming himself at all. So, you crept down to where he was in the kitchen, and waited for him to hang up before you hugged him tightly and shook your head.

“You didn’t go wrong with me anywhere, Bobby,” you murmured to him. “You and Rufus are the best dads a guy could ask for.”

Bobby sighed heavily, although he couldn’t help but to hug you back as he frowned. “Ten good years you’ve been with me, kid - and it’s like suddenly I don’t know you no more.”

You pulled away and cleared your throat, nodding slowly. “I’ll go find the Winchester boys. They’ll put me on the right track, don’t worry.”

•───────────────★•♛•★──────────────•

Four years, you had been on the road with Sam and Dean, now; you checked in with Bobby and Rufus  as often as you could and went to visit whenever you got the chance, but you were happy with the boys in all honesty.

But it was a slow night tonight, on the way to the next town hoping that there would be a case, you and Dean were forced to share a room, as there were only two left in the motel and Sam was… preoccupied with someone who worked at a local pub. 

“You’re not the only hell Bobby ever raised, y’know,” Dean chuckled, shaknig his head as he took a long swig from his bottle of beer.

You shrugged as you hummed softly, nursing your glass of vodka as if it would last all night. “Yeah, Rufus tried to tell me that - but you know me, I only ever do things that my way… and to think, Bobby thought I was a good boy just goin’ through some phase.”

He grinned, doing his best not to laugh as he quirked a brow. “You? Good?”

“You can’t say much anyway,” you mused. “You’re the only hell your mama ever raised.”

He nodded, pursing his lips slightly as he struggled to hold back the laugh. “Maybe so, but at least I didn’t try and pretend to be good.”

You shook your head as you licked your lips, quirking a brow. “Remember when your dad used to dump you at Bobby’s and we’d sneak out all the time?”

“Yeah, ‘cause you were always doing it so I went along - it was only fair,” he pointed out. “But you know how it went down when Dad found out I snuck out… wouldn’t let me have no fun.”

“Don’t worry,” you told him. “Two more years to make it sixteen, then you’ll see - we’ll both have changed our ways.”

Dean put his beer bottle down, crossing the room as he raked his eyes over you, swallowing thickly before dropping to his knees between your legs. “Well, if we only got two more years to make some trouble… why don’t we raise a little hell ourselves?”

You started to chew at the inside of your lip, breath hitching in your throat as you looked down at him and noticed that sparkle in his green eyes; you nodded, which only earned you a playful smack to the side of the knee. 

“C’mon, be a good boy and don’t act coy,” Dean told you softly. “Tell me.”

You nodded again, clearing your throat and almost gulping. “I’m sure we can raise a little hell.”

Slowly, he ran his hands up your legs, settling his fingers between them so that he could feel the outline of your cock; gently and carefully, he started to palm it through the dense and coarse fabric. “This okay?”

You stifled a moan as you nodded. “Y-yessir.”

He grinned. “I like that. You want me to keep goin’?”

You couldn’t even stifle your moan anymore, letting it out with a shuddering breath as you raised your hips a little and practically squeaked out for his touch; Dean helped you slowly, pulling your jeans and boxers down to your ankles before wrapping his hand around your cock and giving it a few firm pumps.

With great control, Dean slowly licked a stripe from the base to the tip and hummed softly.

“Don’t stop,” you groaned out softly, and when he finally took you into his mouth, you felt like that was it.

Fuck raising hell, you never wanted the sensation to end; his mouth was so warm and wet, his tongue worked you so expertly and when he used one hand to massage your balls and the other to wrap around your cock and stroke it - fuck.

You didn’t want anything else in the world. Your hand managed to find its way into his hair, tugging at the short brown strands softly as you tilted your head back and stared at the ceiling for a moment before closing your eyes tightly shut.

Letting yourself drown in the feeling of his mouth around you. The soft sounds of his mouth as he took every inch of you one bit at a time; his eyes closed as he focused on nothing but making sure that you felt as good as possible.

Even the soft little moans he made around your cock only spurred you on more and more as your breathing grew more ragged and harsh by the second, doing your best not to buck your hips and fuck his mouth as hard and fast as you could.

But fuck, when he started to twist his hand a little bit, you were nearly completely over the fucking edge.

Dean’s movements picked up as he realised how close you were getting, almost desperate to taste your cum in his mouth; his spit and your precum mixing so that his mouth squelched a little around you; you could already feel it coming, your toes beginning to curl in your shoes as you heard him gag and grunt around you.

Your grip on his hair grew tighter as you gently bucked your hips against him, needing nothing more than to know what it felt like to cum in that pretty and smart mouth of his. You buckled, thighs shaking as you yanked at his hair one last time and, without warning, finally came.

To his credit, Dean didn’t stop, still sucking and licking your cock until it was perfectly clean, a long trail of spit from his mouth when he pulled away at last, looking up at you with a massive fucking grin.

“Fuck,” you breathed out, wiping sweat from your forehead as you realised just how fucking weak you were from your own orgasm. “You weren’t kidding about raising hell, huh?”

Dean shook his head as he laughed softly. “Nope… but if you wanna, we can keep goin’, maybe see just how far we can get until the morning.”

if you made it to the end of this fic and you enjoyed it, then please, if you have any cash to spare even if it's £1, then please consider making a donation to help Tahani to save her family. Please, every little contribution does genuinely help!

[delusionalwritingsofagay]

Hiya love, I was wondering if you could do a fic with Dean Winchester? Dean is bisexual and has a boyfriend but hasn’t told Sam or Bobby yet (around season two) and his boyfriend is like a model or something? Anyway, Dean finally works up the courage to tell them and Sam and Bobby are all like “yeah, we know” and Dean’s all like shocked and his boyfriend chuckles kissing his cheek telling him something like “I told you you idiot!”

The Closet is made of glass

Pairing : Dean Winchester x Male reader Tags : Coming out, established relationship, Set maybe season 2, family feelings, Fluff Word count : 922

Authors notes : I'm so sorry for the wait I suddenly forgot how words worked, anyway I hope you like it :)

The Impala roared down the dark, winding roads of whatever backwoods they found themselves in. Dean Winchester was worn out, tired from a long hunt that hadn’t gone as smoothly as they’d hoped. But the weariness was not just from fighting monsters; it was the weight of untold truths that bore down on his heart like a lead weight.

Dean glanced sideways at Y/N, his boyfriend, perched in the passenger seat, effortlessly stunning as always. The way the moonlight caught their features made them look even more like a model just stepped off the set of a photo shoot. The smooth curve of his jaw, the soft light in his eyes, made him ache with a mixture of love and anxiety.

“Hey, are you alright?” Y/N asked, breaking the comfortable silence that had enveloped them. His  voice, soothing and melodic, wrapped around Dean like a warm blanket. He absently ran a hand through his tousled hair.

“Yeah, just tired,” he replied, forcing a smile. But inside, he was a storm – the fear of revealing his relationship with Y/N gnawed at him. He hadn’t told Sam or Bobby yet.

They parked at a small motel, the flickering neon sign casting an eerie glow that seemed to dance and flicker, almost mocking Dean’s internal dilemma. As they walked into their shared room, Dean’s heart raced. He had planned for this moment, rehearsed what he wanted to say a dozen times, but the words never seemed to stick.

“Dean,” Y/N said, stepping in front of him and gently cupping his face. “You look like you’ve seen a ghost. What’s going on?”

Dean hesitated, his chest tightening. “It’s just… I’m worried about telling Sam and Bobby,” he finally confessed, his voice barely above a whisper.

Y/N smiled, a knowing glint in his eyes. “You’re worried they won’t accept you, huh?”

“It’s not that! It’s just… they’re my family, Y/N. They might freak out knowing I’m… bisexual. That I’m with you.”

Y/N chuckled softly, kissing his cheek gently. “Dean, you idiot. You think they don’t already know?”

His stomach dropped. “What do you mean?”

“They’re not blind, Dean. They see the way you look at me. The way you smile when I walk into a room. Trust me; they know more than you think.”

Dean’s heart raced even faster. “But what if I’m wrong? What if they don’t accept it?”

“Then let them surprise you,” Y/N encouraged, his eyes softening. “You are brave when it comes to fighting monsters. This is about you, Dean. It’s okay to be vulnerable with them.”

He sighed, releasing some of the tension that had built up inside him. You’d think after years of hunting supernatural creatures, admitting his feelings for someone would be simple. But no, Dean Winchester could face off against demons and ghosts, but facing his family with this truth felt impossible.

As if reading his thoughts, Y/N nodded, squeezing his hand. “Let’s just focus on one step at a time, okay?”

Taking a deep breath, Dean agreed. “Alright, let’s do it.” He felt slightly reassured, bolstered by Y/N’s unwavering support.

Later that evening, with the weight of the moment looming over him, Dean called Sam and Bobby to sit down with him in their cramped hotel room. His heart raced as Sam sauntered in, looking as perplexed as Bobby. They shared sidelong glances, sensing Dean’s tension.

“Dean, you good? You look like you just met a  Reaper,” Sam remarked, raising an eyebrow. Bobby merely nodded, crossing his arms and leaning back in his chair.

“Yeah, you look like you’re about to announce the end of the world,” Bobby added with a hint of concern mixed with his usual gruffness.

“Uh, yeah, about that…” Dean started, voice shaky. Y/N stood beside him, offering silent support.

“Guys, I just wanted to—” He swallowed hard, “I wanted to tell you both that I’m… I’m bisexual. And… I’m with Y/N.”

There was a moment of silence, the kind where a pin could drop and shatter glass. Dean felt the heat creeping up his neck, embarrassment gnawing at him.

“Yeah, we know,” Sam said flatly, a grin creeping across his face as if the tension evaporated in an instant.

Dean blinked, his brain struggling to process that. “Wait, what? You knew?”

Bobby chuckled, the corners of his mouth twitching upward. “Boy, I’m not nearly as old as you think. I can see you’re happier, and it didn’t take a psychic to figure it out.”

Y/N let out a soft laugh, stepping forward and playfully nudging Dean. “See? You worried for nothing.”

Dean’s mouth dropped open in shock, his heart pounding in disbelief. “Why didn’t anyone say anything?”

“We figured you’d come to us when you were ready,” Sam replied, his expression softening. “Besides, it’s none of our business to push you into anything.as long as you’re happy, that’s all that matters.”

Feeling the weight lift from his chest, Dean turned to Y/N, who wore a proud smile. “See? I told you, you idiot!” he  teased, leaning in to plant a kiss on his cheek. The warmth of his affection wrapped around him like a shield.

Dean grinned, the tension melting away. “Well, I guess I’m the idiot then,” he chuckled, feeling lighter than he had in a while. 

As they settled into comfortable banter, joking and reminiscing, Dean caught Y/N’s eye from across the room. Y/N winked at him, and he felt a surge of affection.

[m4ng0-gh0st]

Spn boys NSFW headcannons (CIS male reader)

Dean

You had to help him out the first few times but after that he got it DOWN.

One of his favorites are you on your knees sucking him off.

He definitely teases you by moving his hand really close to your crotch or sometimes he full on just palms you through your pants when your sat next to him however it highly depends on what is going on and where you guys are at.

If you were one of the "villains" you two definitely used to have hate sex.

If you aren't them you two just have sex to release some steam if it's more of a friends with benefits relationship but if it's a romantic relationship then it's because you two genuinely enjoy having sex

Most definitely rough sex most times but if he has the time and or nobody will be around for a while then it'll be more sensual.

Sam

He more of a groaner than like a moaner/whimperer.

I mean maybe you can get him whimpering 🤷

Don't pull his hair no matter how tempting it is...

He definitely likes you riding him but if you are the dom you then missionary. (He definitely does missionary even when he's Dom)

He does like seeing your face during sex.

Nothing to out of the normal he's pretty simple when it comes to sex.

Castiel

He doesn't make much noise I mean maybe a groan here and there and if you're lucky a moan or whimper.

He's a little clueless when it comes to sex despite him watching the pizza man and the baby sitter... But that's okay! You help him the best you can.

You can definitely get him to moan or whimper if you suck him off.

You most definitely end up the dom most times.

If you like rough sex then he’ll participate but he does enjoy gentle and sensual sex more.

You two have most definitely gotten caught and or have been overheard while having sex.

Crowley

You know he's in the mood when he starts getting handsy.

He'll pull you into his lap or if you guys are around people he'll pull you away or teleport you two away.

This does happen quite often.

You don't really know what you do to make him horny but you do make him horny a lot.

You've two been caught making out somewhere in the bunker because Crowley had pulled you away.

You two have experimented quite a lot.

He denies it but he does really like intimate and soft sex.

He does occasionally like you as the top but when you are the top you are 6/10 times a soft top

He does get whiny and bratty. Mostly when you two have been very busy and haven't had sex in a while.

Definitely sasses you during sex. He has a loud mouth and he can't help himself.

Praise him and he seems fine but on the inside he is DYING

Gabriel

He's even worse than Crowley when it comes to getting handsy.

He is a brat when he's the sub for sure.

Kinky as hell 💀

You've guys practically have tried EVERYTHING.

A little bit after he returned from being tortured you guys basically had a whole day spent on having sex.

He enjoys either making your brain turn to mush or having you turn his brain to mush.

He has a lot of energy and when I say a lot I mean A LOT.

He is a major switch when it comes to you.

Jack

I don't know if it's alright to do some for him since he's technically like 3 but he's fully grown so let me know if it is 😭💀

[river13245]

They React To You Being Asexual

Dean, Sam, Castiel, Crowley, Rowena, Lucifer

(this is going to be a thing that I do regularly so request)

Dean Winchester

The both of you have been dating for almost a month now. You weren't oblivious to the fact that Dean was a very touchy guy. He would go to bars and pick up women all the time before you came around. Maybe that's why you had a pit in your stomach. You go to dean who was in the main room of the bunker and ask dean if you could talk to him in private.

He gets up and walks into your guys's room. "what's going on. Something happen?" he asks and you shake your head. "no not yet. Uh I just thought I should tell you something" He sits down on the bed and looks at you. :alright what's going on?" you take a deep breath in and speak all in one breath "Im asexual. I know that you like sex which is not a fault but I just know i'm not going to be able to give that to you"

He asks you to explain it to him and when you do he nods and its quiet for a moment before he speaks. "babe this isn't going to change anything between us. You don't want sex. that's fine i can take care of myself if i need to. Don't feel bad" when you sit beside him hs places his hand on your thigh and you rest your head on his shoulder.

Sam winchester

Your boyfriend was sitting on the bed reading when you entered the room. He looked so nice in the sweatshirt and sweatpants he was wearing. You were taking a moment to think about how you wanted to tell him that you were asexual.

Sam had never once made you feel as if you had to do anything you didn't want to do. If anything he was always cautious for first moves. your first kiss he leaned in slowly, making you close the gap. He also never really asked or initiated for the both of you to go any further beyond just kissing and cuddling. You had a feeling he knew which made you less nervous. "whets going on in that head of yours" he asks as he looks over at you.

You sit onto the bed beside him. "there's something I need to tell you" he puts his book down to give you his full attention before nodding. You take a breath before saying calmly "i'm asexual. I don't ever want to have sex with you. I should have told you sooner and i'm so sorry I didnt i was just waiting for the right time an-" You stop speaking because sam has placed both of his hands on the sides of your face and kisses your lips. "its okay honey, I have had a feeling that you might be and I still love you either way. Plus i have a lower sex drive than most people so you dont have to worry with me okay?" You nod and you cuddle up against him as he reads a little while longer.

Castiel

You were sitting on your bed just thinking about how you were to tell your boyfriend that you were asexual. Your boyfriend had never really said anything about wanting sex or anything like that but it still made you nervous. You knew Castiel wouldn't break up with you because of it. So once you calmed yourself down a bit you prayed for him. "castiel I need to speak with you"

Wasnt even 2 minutes later and hes standing in front of you. "Theres something on your mind?" he asks and you nod. "yes there is. I just needed to tell you that if we are going to continue our relationship..there will be no sexual acts. Kissing and everything is fine but just not sex."

He looks at you for a moment before he takes your hand in his "That is perfectly fine. Angels dont need to have sex." you lean in and kiss his cheek and hug him

Crowley

Crowley had been in one of his moods today. Your boyfriend was a very moody person. One thing could piss him off so because of this you were not looking forward to telling him about the fact that you are asexual. In fact you were thinking about not telling him. Not for a while anyways.

However when he walked into the room he could see the way you didnt come up to him to welcome him back like you always did. So he crossed his arms and looked at you. "what" you asked as you looked up at him. "What is going on? You arent acting normal" this caused you to roll your eyes at him. "when have I ever been normal" he shrugs but doesn't say anything else which makes you sigh.

You laid down onto the big bed you two shared. "Crowley I am asexual. That's why I haven't made a move to do anything more than kissing" He uncrossed his arms and lays down beside you. "really that's what's got you so weird?" nodding in response he rolls his eyes. "I'm a demon and have lived much longer than you have. You being asexual is the least of my problems. I want to be with you either way"

Rowena

Rowena was doing some of her witchy stuff looking beautiful while she focused. You knew you shouldn't interrupt her but this was eating you alive. Your friends had been talking about their partners and how they were great in bed and everything else. You loved your friends of course but its started to eat away at you. That you couldnt and wouldnt give that to Rowena.

She was a woman and many women want that part of the relationship. That kind if intimacy and you were feeling awful about it. Rowena deserved an explanation so before you could talk yourself out of it you walked up to the table and took a seat. "Rowena Love" She looked up at you and when she noticed how you looked she stopped what she was doing. "what's wrong dear"

You let out a long sigh before explaining to her about what you and your friends were talking about and then you pause for a moment before speaking again. "I know that you probably want that and I cant give it to you. How could you possibly be happy like this" She places both her hands on the sides of your cheeks and kisses your forehead then your lips. "I am happy with you. There has not been a moment where I doubted us or my feelings for you. You are the one that I want to be with for the rest of our time here" She pulls you into a soft hug

Lucifer

You had just walked back into your home and Your partner was sitting on his chair that he had claimed as like his "throne". He had been talking to a few other demons that worked for him and so you tried to walk quickly past them but he made you stop. "where do you think your going?" he wasn't angry he was just confused because you usually greet him when you come back home. You look at him "i'm going to our bedroom"

He could tell by the tone of your voice and your body language that something was wrong. So he quickly made the demons leave before turning to look back at you. "come here" you walked closer to him and he looked at you sitting up more on his chair. "what happened while you were out?" He was very protective over you and it was written all over his face. You knew he was going to find out anyways so you begin to tell him.

You tell him about how your friends were asking about how you and your boyfriend was. Asking how the sex is going etc etc. Lucifer nodded and was actually letting you finish speaking. "when I told them that. We don't have sex because i'm asexual they started judging me and everything." He almost speaks up but you cut him off "why do you stay with me. Lucifer I know that you have had many demons and even other angels in your bed before. Why stay with the one who cant give you what you need"

Lucifer looks at you as if you just said something in a language he didn't understand. He uses his power to bring you closer to him and then he stops and holds his arms out for you. Silently telling you to sit with him and so you do. You sit on his lap and rest your head on his shoulder. "I may have had others share a bed with me. But none of them have had such a emotional hold on me before. You are the one that i fell in love with. Don't ever doubt me or my feelings towards you." he says the last part with such a serious tone and all you can do is nod and let him hold you.

[supercap2319]

Dean eats your ass while your trying to do research.

"Ohh, Dean!" Y/N whimpers as he grasped the table for dear life and support as he felt Dean's slick and wet tongue inside him.

It didn't start out like this. They were looking into a case and Sam asked Y/N to do some research while he cross-referenced all the possibilities of what it could be, and where it would strike next. It was quiet and boring research until Dean showed up with a mischievous glint in his eyes.

He tried to protest that they would play later on, and that Sam would kill him if he didn't do this research, but the moment Dean slipped his hands in his pants, it was all over for Y/N. He was stood up and bent over the table as Dean pulled his pants down around his ankles and gave a sharp smack to his ass as Y/N yelped. Dean whistled. "Damn. You gotta nice ass. I betcha that tight pucker of yours is just itching for my tongue. Maybe my cock."

Y/N shivered at Dean's dirty talk and before long, he was having his hole eaten out by Dean as he tried desperately to finish his research.

[m4nspr34d]

TWENTYSOMTHIN’

Dean Winchester X M!reader

Warnings : Angst, fluff. Nothing extreme

Summary : After a few years of dating you finally bring up the topic of marriage, which you two have only briefly spoken about. Dean shows displeasure at the idea, reminding you of when you first met.

It had been months since you and Dean had spoken about where your relationship was heading for the future, something that he got angsty about when you brought it up. Marriage was a big no for him; and for a long time, you were completely with him.

Your eyes followed him as his head moved to the best of guns and roses playing, watching as he loaded the shotguns full of salt. The thought was unbearable, you couldn’t shake it no matter how hard you tried.

“What’d you do if I proposed?” He stopped, his eyes widening for a moment as his hands halted. “What?” His eyes stayed on the shotgun, his hands still. “If I proposed.” You placed the shotgun onto the table, leaning back and crossing your arms, letting him know this was the conversation you wanted to have; the one you needed to have. “Are you gonna?” His eyes lifted, his eyebrows doing the same. “Well— No.” You said, thinking for a moment. You weren’t sure if he meant at this very moment, or ever, but no seemed like a good choice for now. “It doesn’t matter then.”

Your eyebrows furrowed in surprise, watching as he disregarded you and went back to the shotgun. “No, we need to talk about this.” “No, we don’t.” “Yes, we do!” You weren’t going back and forth with him about this, so you tore the shotgun from his grasp and threw it onto the bed, sitting on the edge, having to turn your neck to face him. “What’s this even about, you said you didn’t wanna get married.” He said, a sigh; a deep bothered sigh lining his words. “That was years ago, Dean.” You softened your voice, innocence.

“You know how I feel about it, it’s dumb, the whole thing.” He grimaced at the thought, looking away from you. It wasn’t something you expected him to like, but that didn’t make it any less painful. “I don’t think so.” The tone of your voice dropped, turning you head away from Dean, both of you facing in opposite direction’s. “I’d do anything to put a ring on your finger.” His breath paused. He had never considered it, of course he couldn’t imagine his life without you, he wanted to grow old with you, but he never even saw both of you getting old.

It was silent, he was lost for words, it hurt, it hurt so bad. “Seeing you in a suit, our first dance, sitting at that table with you, eating fancy meals, all of it.” Still silence. You had no more words to say, not till he gave it the light of day, you felt like you were taking to a damn therapist. “Jesus— Will you say something!?” “What’d you want me to say?!” Truly, you had no idea. If he said yes; it’d feel like a compromise, something to shut you up. If he said no; well, you had no clue.

“You know I wanna be with you forever—�� “Then marry me.”

…

“Dean?” “I can’t, you know I can’t. But it means nothing, a ring won’t make us official, that’s our call.” His hand trailed to your’s, his finger tips rubbing against your finger; your empty, ring-less finger. You pulled away, squeezing your eyes shut. You wanted to walk away, come back and forget this conversation happened, but it was too late. You knew he wasn’t ready to commit to you, is he waiting for someone better? No.. Maybe?— No. Your thoughts were the loudest thing in the room, not your words, not his, not even the busted AC. “

“So would you say no?” Your voice was cold, blank as you shut your eyes, taking in the silence while it was there.

He inhaled sharply, biting his lip as he clenched his jaw, balling his hands into a fist. He felt like rolling over and dropping dead, this was the last thing he wanted, it had come on him so unexpectedly, like a bad cold. “Yes.” He said, finally mustering up the courage. You’re eyes squeezing shut as you felt an itch on the corner of your eyelid, followed by a tear as you steadied your prolonged inhale.

You giggled as you watched the twentysomthin’ man smirk at you, licking his teeth as your eyes locked within his. “You’re really something.” Your eyes narrowed as you spoke, chuckling. “Maybe, you like it though.” He said, a sultry tone coating his lips as the words rolled off. You don’t even know this guys name, his age, for all you know he could be some crazy bastard. “You ain’t gonna ask me my name, sweetheart.” His hand leaned against the back of the bench, wiping the snow from it, the small flakes tapping off the sleeve of his jacket. “Enlighten me.” His smirk grew, his head turning away for a moment as his tongue clicked. “Dean.”

Dean. Fitting, not sure why but— it was. 20 Minutes ago you were sitting out the back of the club, contemplating weather to spend your last few bucks on a box of cigs, but you had completely forgotten about it by the time this guy: Dean, had weaselled you down the street to the park bench in the middle of December, snow and all. “Let me guess, bartender?” You were sure you were right, that charming face was bound to get his tips up. “Not even close.” You scoffed, surprised you were wrong. “What is it then.” Your chest rose and sank with each breath, the cold air flowing towards the ever shrinking space between the two. “Cars, I fix cars.” “So a mechanic?” You said, raising your eyebrows, tilting your head. “Guess so.” You decided not to question his awfully vague answer. “And you?” He said, his eyes still fixed on you, the small white dots of frosty snow scattered around your clothes. “In between.” “In between jobs and you have time to blow your buck on a cheap bar in the middle of the city?” His voice laced with that undermining tone he’d been slipping.

Who even was this guy, really. You couldn’t wrap your head around it, something so unexpected, so— everything. “Tell me somethin’, you got a boyfriend? A husband?” He said, his eyes widening as his words trailed. “God no, never. Marriage makes me nauseous.” A chuckle followed you words, a quick glance to the marina, the snow lacing the black railing. “There has got to be a catch with you.” The tension was tight, airtight, feeling the air around you stiffen, the snow became background, your attention fixated on him, and only him.

Divider’s: @cafekitsune 💌 : Another short little fic. In complete honesty, I acc got the idea from the song twentysomthings, i’m not acc sure who sings but, oh well! But I got like, this cute little picture in my mind of Dean and whoever sitting out on a bench by the water late at night, snow everywhereee!! Super cute imo. I’ll try my best to do a longer more fleshed out fic, and eventually smut when i’m ready. 🌹