#Dean winchester x male!reader | Explore Tumblr Posts and Blogs

supernaturalscribe67 · 8 months

Text

Lucky

Words: 4,699

POV: 3rd Person

Pairing: Dean/Sam Winchester x Trans!FTM!Winchester!Reader [Platonic]

Warning(s): Mention of surgery, references to top surgery recovery, slight gore (maybe?), language (also, maybe?), loving and supportive family members, fluff

Summary: Top surgery was never something the reader thought was possible. With the help of Sam, he was able to make his dream come true, and his brothers are there for him to help while he's in recovery.

Request:

I would absolutely love Dean and Sam with a younger trans brother who just got top surgery and is in recovery? Just fluff of like helping him wash his hair or getting things for him and reassuring them? Love your content so much!! It so nice to see some more trans content in the supernatural fandom :)

@cometcreates

A/N: I am so sorry this took a little longer to get out than I planned - work has been extremely hectic and draining recently - but I hope you like it! Let me know what you think! Feedback is greatly appreciated!

Much love!

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People define luck in many different ways. Some say luck is a dollar bill lying on the ground, some say it’s a passing grade once they get their tests back, and others say it’s their true love. (Y/N), however, would define his luck as waking up every morning in the Men of Letters bunker with his brothers.

Years ago when he came out to his older brothers as transgender, although they were a little confused at first, they were fully supportive. They did everything in their power to make sure that their little brother was comfortable, not only in their home and out in public but in his skin as well. They purchased a binder for him, got him better clothing, adjusted rather quickly to his name and pronoun change, and got defensive - sometimes a little too much - whenever someone misgendered him. With all that they were doing for him, (Y/N) couldn’t imagine how luckier he could get. He already had an amazing support system, what else could he need?

At the end of last year, Sam approached him and asked him if he had been wanting to get top surgery, something they had talked about once or twice, but never regularly. When (Y/N) showed his interest in getting the surgery, Sam told him that he had done some research about different places where he could potentially get the procedure done, as well as all the criteria that certain places needed for him to qualify. After they sat and talked for a while, they concluded that, with Sam’s assistance, they would get started on (Y/N)’s journey toward top surgery.

The months following consisted of semi-monthly visits with a psychologist Sam found in Hays, KS - all of the medical professionals required a steady diagnosis of gender-dysphoria from a registered psychologist to be able to consider the patient for the operation - as well as reading up on the aftermath of the surgery and what was to be expected. Of course, (Y/N) knew he would get all of the information from his surgeon before it was done, but he wanted to make sure he was well-informed and nothing was left out of the consultation.

The consultation went well, and, after waiting for an eternity in the examination room, the doctor finally came in and set up the date for the surgery. (Y/N) was over the moon, and he immediately began to count down the days. Sam and Dean helped him get all of the necessary items he needed for the surgery recovery; various snacks, scar care creams, a surgical binder, a mastectomy pillow, and an extremely cozy blanket that he had begged them to buy. Even after they had gotten everything on the list, occasionally, they would buy something they thought would be beneficial for the recovery period.

Then, they waited. Day after day went by and (Y/N) found it difficult to focus on hunting rather than the anxiety and anticipation that bubbled within him, but his brothers kept him grounded in times of distress. They could tell just how excited he was, and they never wanted to dampen the mood by turning his focus back on the job. They wanted him to keep that enthusiasm even after he had the surgery. When the day of the surgery came, they didn’t even try to calm his excitement. Just seeing how happy he was made them feel the same.

The surgery went well. The recovery was going to be the hard part. The doctor made sure to prescribe him pain medication, which the brothers had picked up before they left the surgical center to head back to the bunker, and gave him a pamphlet describing all of his recovery needs in grave detail. Of course, they had already been well-prepared for the occasion, but it was nice to have it on hand. (Y/N) stayed in the hospital under observation for two days until he was finally released, clad in nothing but a pair of shorts, some slides, his surgical binder, the drainage tubes and bulbs connected to each incision underneath the binder, and one of Sam’s flannels that rested against his shoulders, keeping the front open to allow his chest to breathe. After he was wheeled and loaded into the back of the car, the three brothers made the drive back home.

By the time the Impala edged its way into the well-lit garage, the sun had gone down, and the night sky was littered with stars. It wasn’t a long way to Lebanon from Kansas City, about five hours depending on traffic, but the trip wasn’t entirely painless. (Y/N) was thankful for the medications he was given after his surgery, but the bumpy backroads in Kansas were ruthless and did little to provide a comfortable drive home. He initially tried to sleep through the journey, but every pothole they hit - accompanied by an apology from his oldest brother - sent another wave of discomfort coursing through his chest. He had never felt more joy in his entire life than when he saw the familiar dirt road as he and his brothers got closer to the bunker.

Dean parked the car and killed the engine. He turned, arm draped over the back of the front seat. “You feeling okay?” He asked.

(Y/N) glanced over at him and gave a small nod. He adjusted himself and winced as the pain shot through his arms and chest. “Just sore, hurts like hell. When am I due for my next round of meds, Sammy?” He turned to his older brother in the passenger’s seat.

Sam looked back at him for a moment and then down at his phone screen. “You should be able to take some more now. Why don’t we get you inside and into your bed first? That way we can get you something to eat and drink with your medicine.”

“No food,” (Y/N) groaned. “I don’t feel like eating now.”

“You have to eat something.”

“Fine, I’ll eat some crackers, or something small, or one of those snack cakes I got, but I really can’t eat anything filling right now. I’ll eat some more in the morning when I’m feeling better.”

“Alright,”

“Now, can someone let me out? These doors are surprisingly heavy.”

“Yeah!” Dean said, quick to jump out of the car and head towards the back passenger’s side. He opened the door and held out a hand.

(Y/N) smiled weakly as he reached over and grabbed Dean’s hand. He was slow to move out of the seat and plant his feet on the ground. When he stood, his legs shook, but he let out a sigh of relief. His legs were weak. The recovery had consisted of laying in his hospital bed and, occasionally, getting up and taking a few steps inside his room, just to keep the blood flowing in his legs. With the lack of energy he had and the five-hour ride back, his legs felt completely numb, as if they were made of Jell-O.

Dean held (Y/N)’s hand tightly while his opposite arm wrapped around his waist. He moved him away from the car and shut the door. The two of them made their way to the bunker door. Sam jumped out of the car and caught up with them as they walked inside. When they were greeted with the metal stairs that landed in the War Room, (Y/N) stopped. He let out a sigh of defeat.

“This is going to hurt like Hell,” he mumbled. He reached a shaky arm over and grasped the railing until his knuckles paled.

“We’ll take it slow,” Dean nodded softly.

(Y/N) returned the nod and they began to walk down the stairs, one step at a time. The entire time they walked, Dean held onto him tightly, both of their eyes cast down towards the steps. Each step, despite the snail’s pace they walked at, made a jolt of pain shoot through (Y/N)’s back. A pained expression crossed his face multiple times as he pressed his lips together tightly.

Finally, they reached the bottom of the stairs and another contempt sigh left (Y/N)’s lips. Sam brushed past them.

“I’m going to grab your crackers and water and meet you in your room, okay?” He placed a gentle hand on (Y/N)’s shoulder.

“Sounds good,” (Y/N) flashed a thumbs-up towards him before Sam walked down the hallway, toward the kitchen.

(Y/N) was a little quicker when they walked through the halls, and he was thankful when they reached his room. He wasted no time parting himself from his brother and making his way over to his bed. Despite his shaky legs, he held himself up well. He turned on the lamp on his nightstand, illuminating the room with a faint yellow glow.

His bed was neatly made with multiple pillows resting at the head - the doctor recommended that he slept elevated for the first week or so and then slept on his back for several months afterward. It would be an adjustment, but (Y/N) knew that he could get used to it.

He climbed into his bed, careful of the collection bags on his chest, and crawled underneath the layers of blankets. Instantly, he relaxed into the plush mattress, head resting on the stack of pillows behind him. Dean waltzed deeper into the room, eyeing him carefully.

“You okay?” He asked.

“Better now that I’m in bed,” (Y/N) looked over at him. “Although it just feels like I’m in another hospital room.”

“At least you won’t be eating any more hospital food,”

(Y/N) grimaced. “Don’t remind me of that, I’ll throw up.”

Sam entered the room, a bottle of water in one hand, the white bag with (Y/N)’s prescription narcotics tucked under his arm, and a small sleeve of saltines in the other. He set the water bottle and saltines down on the bedside table and opened the bag. He took out the orange pill bottle and fished out an oval-shaped white capsule. He handed it to (Y/N), who took it gratefully. He popped the pill into his mouth and drank some water to wash it down.

“You should probably empty those soon,” Sam said, gesturing towards the bags that rested against (Y/N)’s stomach.

(Y/N) glanced down at them and shook his head. “The doctor said every twelve hours should be good. They changed them right before I left the hospital, so they should be fine for right now.”

“Alright, if you say so,” Sam crossed his arms over his chest. “Do you need anything? TV? Books? Some snacks?”

“I’m good, thanks. I think I’m going to catch some shuteye for a bit. That car ride took all the energy out of me.”

Sam nodded and turned to walk towards the door. “If you need anything, let us know.”

“I will, don’t worry.”

“Seriously,” Dean piped up. “If you need anything, even if it’s small, just holler or shoot us a text.”

(Y/N) couldn’t help but chuckle. The overprotective nature of his brothers was something that never changed. “I promise I’ll call if I need anything.”

Dean and Sam both gave him a small smile before they turned and left the room, closing the door behind them. (Y/N) marveled in the silence. No nurses walking outside of his room, no snoring from his brothers on the pull-out beds, no heart monitors beeping constantly. It was peaceful. He reached over and turned off the lamp light, flooding the room, once again, with darkness. The darkness was something he missed. He would never take his pitch-black room for granted ever again.

He awoke six hours later, around the time when the medication began to wear off and the pain resurfaced. He had tried to reach over to the nightstand and grab the pill bottle, but his arms were too stiff. He swung his legs over the side of the bed and sat up, a grunt falling from his lips. The pain wasn’t as bad as it had been the day after surgery, it was mostly the sore tenderness he felt in his chest and back that bothered him. When his feet touched the floor, he was able to lean over and grab the pill bottle with ease. He uncapped it, took out another capsule, and popped it into his mouth, followed by a drink of water. The medication would start working in twenty minutes or so.

The ache wasn’t only in his chest and back, however. As he downed the water, he felt it fall into his stomach. A gurgle sounded from his gut and he placed a hand over it. He probably shouldn’t have taken the medication on an empty stomach. He needed some food. For a moment, he considered the saltines on the bedside table but quickly tossed out the idea. They didn’t sound as appetizing as they had before he went to sleep, and even then he had only accepted them to make his brother feel better. He wanted some real food. He wanted some of the snack cakes that he got for the occasion. The real question was; could he get up and walk to the kitchen by himself without bothering his brothers? It was still early, so they were most likely asleep. They had been with him the entire time he was in the hospital, and he wanted to make sure that they got the sleep they deserved.

(Y/N) placed his hands on his knees and let in a deep breath, his eyes falling closed for a second. With a quick exhale, he hoisted himself off of the bed. His legs quivered, and he had to reach back towards the bed to steady himself. After he stood for a couple of minutes, the blood seemed to flow back through his legs. They were unsteady, but less than they had been before. He shuffled his way towards his door and opened it, glancing up and down the hallways. He then made his way towards the kitchen. The sound of his stomach growling echoed throughout the corridor.

“Damn, I’m getting you food, calm down,” (Y/N) mumbled to himself.

It took a lot longer for him to get to the kitchen than it had taken to get to his room the night before. He was slow, uncomfortably so, and he hated it. He felt like an old man. At least I’m an old man without tits, he thought.

When he got into the kitchen, he walked over to the pantry shelves and glanced up. Sat on the second highest shelf were the cupcakes that he had been craving. Those delicate, chocolatey, packaged goodies. They were teasing him with the pictures on the front of the box. He wanted one so bad, and he couldn’t even reach them. He could barely lift his arms enough to reach the shelf directly in front of him. He tried to scour the shelf in front of him for something that sounded at least a little bit appetizing, but nothing made his mouth water as much as the soft, chocolate cakes near the top of the pantry.

Curse you, Hostess.

Just as he was about to give up and pick something from a more accessible shelf, the sound of padded footsteps echoed down the hallway. (Y/N) turned his head towards the door as Sam entered. Sam furrowed his brows.

“Hey, what’re you doing up?”

“Oh, the pain medicine wore off, so I took another one. Plus I’m starving,” he then turned his gaze back to the cupcakes.

“Do you want me to make you something for breakfast? I can make scrambled eggs.”

“Sure,” (Y/N) shrugged. “But…I really…want a cupcake.”

“For breakfast?”

(Y/N) looked back at Sam. His bottom lip was pushed out in a small, child-like pout. His eyes were big and his brows were tilted up slightly. It was his own signature puppy-dog eyes. Sam’s puppy-dog eyes were good, but (Y/N)’s was better. Those eyes were the reason behind him getting to pick a place to eat or what movie they watched most of the time.

Sam sighed as he walked over, grabbed the box of cupcakes, and ripped it open. He took out a package and handed it to (Y/N). (Y/N) beamed and ripped the plastic open. He took a big bite of the cupcake and hummed happily.

“Ok, you have your cupcake, but I’m still going to make you some scrambled eggs. You need to have some real food in you.”

“Cupcakes are real food, Samuel. Maybe you’d be happier if you ate one once in a while.”

“And maybe you’d be happier if you ate healthier.”

(Y/N) stuck his tongue out at Sam. Sam rolled his eyes and smirked before he walked over to the fridge. Meanwhile, (Y/N) trudged over to the table and sat down.

“You should probably change your bags soon,” Sam said.

(Y/N) glanced down at the bags and noticed that they were halfway full. He cursed under his breath. “Let me enjoy my cupcake and then I’ll empty them.”

“Do you need help?”

“Nah, I got it, thanks, though.”

Sam smiled and nodded. Without hesitation, (Y/N) shoved the rest of the cupcake in his mouth, a hum of pleasure emitting from his throat. Sam grimaced and turned away. (Y/N) glanced over at him.

“Don’t judge me,” he mumbled with a mouthful of food before he stood up and made his way to the bathroom to drain his bulbs.

Three days had passed, and (Y/N) had already started feeling better. His movement had increased, the pain was starting to diminish, and the fluid that filled the bulbs slowed. His mental health had noticeably improved and every time he looked in the mirror, admiring his newly sculpted chest, the smile would never fail to stick to his face for hours on end. One thing that he didn’t like about the recovery process though, something that stayed a consistent issue, was the lack of personal hygiene.

When his doctor told him that he wouldn’t be able to shower for a while after the procedure, he didn’t think that it would affect him as much as it was. Granted, he still took whore baths, using a damp washcloth and some soap to clean his body off the best that he could, but he could still feel the grime that coated his skin. Specifically, his hair was what bothered him the most. It was wet with grease to the point where it could stand up without any assistance from haircare products. (Y/N) felt disgusting. He needed to get his hair clean, quickly, and he couldn’t do it by himself. If he leaned over too much, the strain on his chest would cause the pain to flair up. He needed help. Sam had been busy researching and assisting other hunters who had called while the brothers were on a break from hunting themselves, so (Y/N) went to the next best person.

(Y/N) knocked on Dean’s door rhythmically. A faint ‘come in’ sounded from inside. He opened the door to see his brother on his bed, lying on his stomach, eyes glued to the television screen in front of him.

“Hey,” Dean said with a smile. “How’re you doing, kiddo?”

“Pretty good. The pain’s not as bad today. I was wondering if you could help me with something, though.”

“Sure,” Dean reached over, grabbed the remote, and turned off the television. He shifted himself so that he was sitting down on the edge of the bed. “What do you need?”

“Can you wash my hair for me?”

“I thought you weren’t supposed to shower yet.”

“I can’t get my chest wet, but I can clean the rest of my body. I’ve been taking whore baths for the past couple of days, but I haven’t been able to get my hair cleaned. Could you help me with that?”

Dean hummed and pursed his lips. “Yeah,” he said as he stood up. “Meet me in the bathroom, I’ll be in there in a bit.”

(Y/N) didn’t wait in the bathroom for long before Dean rounded the corner, a chair dragging behind him. He placed the chair in front of the sink and gestured to it.

“Sit,” he said.

(Y/N) awed. “It’s like a trashy hair salon.”

Dean rolled his eyes and chuckled. He grabbed the shampoo and conditioner from the bathroom cabinet as (Y/N) sat down in the chair. He leaned his head back so that it rested against the cool basin. Dean walked over to the sink and glanced down at his head. He grimaced.

“Damn, kid, you definitely need to wash that hair.” he reached down and touched a lock of his hair, wincing as he pulled his hand back, studying the sheen that the hair left on his fingers. “Ew.”

“Thanks,” (Y/N) deadpanned.

Dean smirked. “Don’t worry, I’ll get you all cleaned up.”

Dean turned on the hot water, the spout shooting out the liquid into the sink. Dean began to run his fingers through (Y/N)’s hair. (Y/N) instinctively closed his eyes. Dean wet his hair, pouring the water over the locks with his cupped hands.

(Y/N) could remember the last time he went to the hair salon. He was young, around the age of six, and Bobby had taken him to get his hair done. Even though Bobby seemed uncomfortable the entire time he was there, he wanted to make sure that (Y/N) had a somewhat normal childhood experience. (Y/N) was ecstatic, and enjoyed every minute of the haircut. His favorite part, however, was when the stylist was washing his hair. It was something about the way her fingers caressed his scalp, massaging the product into the roots of his hair, that brought an overwhelming sense of bliss. Dean’s fingers weren’t as gentle and soft as the stylist’s, but he sure knew how to give a good head massage.

Two fingers gently tapped against the side of (Y/N)’s head. He opened his eyes and looked up at his brother. He hummed in acknowledgment.

“I said ‘Do you like it’?” Dean repeated, a smirk curled into the corner of his lips.

(Y/N) slowly nodded. The suds dripped down from the side of his head and caressed the outside of his ear. “Feels nice. You should have gone to cosmetology school.”

Dean laughed. “I meant your chest. How do you…feel now?”

“Oh,” (Y/N) let out a short laugh. “Honestly, I feel great. I don’t have to bind anymore, which means I won’t have to worry about hunts and catching my breath. I no longer have to worry about if clothes will fit me because of my chest. I don’t look in the mirror and hate what I see…” his voice trailed. “I look in the mirror and I see me. The me that I was supposed to be.”

The two of them were silent for a while as Dean poured water over his hair, washing out the soap. His fingers caressed the back of (Y/N)’s scalp, watching intensely as the conditioner ran down the drain.

“You know, if it makes you feel any better, Sammy and I always saw you as our little brother. I mean, you never really did all that girly crap - makeup, playing with dolls, stuff like that. You were always interested in playing with the mud. The amount of times that you would get in trouble with Bobby because you would bring mudpies into his house, or whenever you would track mud inside when it was raining. He got so pissed,” he chuckled, and (Y/N) joined him.

“But then you got older,” he continued. “And it started to seem like you weren’t really my brother. But…something wasn’t right. I knew something wasn’t right, but I couldn’t quite put my finger on it. Calling you my sister felt wrong. I started calling you my little brother again whenever I told people about you, and then it felt right. When you told us you were transgender, it all made sense to me. It clicked. You never really were my little sister. You were my little brother, just with a few extra parts. Now that you got your surgery, I can see just how happy you are. How comfortable you are, and that means more to me than anything else.”

The conditioner was gone. (Y/N)’s freshly washed hair laid against the basin. Dean reached over to the cabinet and grabbed out a small hand towel. He ruffled the towel against (Y/N)’s damp hair, making sure to get all of the water off of the side of his face and his ears. When his face was dry, he helped him sit up.

“And me seeing you like this, I have never felt more proud of you,” Dean concluded.

(Y/N) glanced up at Dean, brows raised. His wet hair dripped onto his naked shoulder. “Really?” He asked in a quiet voice.

Dean smiled softly. “Yeah. I’m proud that you told Sam and me how you felt. I’m proud that you got the courage to go through with the surgery, and,” Dean knelt in front of the chair. “I’m proud to call you my baby brother.”

A lump had formed in (Y/N)’s throat. His eyes glimmered with tears that pooled in their corners. Without saying anything, (Y/N) reached forward and wrapped his arms around Dean’s neck, pulling him into a loose embrace. Dean placed his hands on (Y/N)’s back and smiled into the hug.

“I owe you and Sam so much,” (Y/N) spoke softly. “You guys take such good care of me.”

“You don’t owe us anything. That’s just what big brothers are supposed to do.”

“Not even if I bake you a pie?”

“Now, if you decide to bake a pie, I won’t turn it down,” Dean pulled away and held his hands up.

(Y/N) sniffled and wiped the tears away. “I should make Sammy one of those fancy salads he likes.”

“Oh, he’ll go crazy for that,” Dean mumbled. “Him and his damn rabbit food.”

“You go crazy for pie, though.”

“Yeah, but pie is good. Actually good.”

(Y/N) rolled his eyes, causing Dean to chuckle. Dean stood up and brushed his jeans off, stretching his arms above his head.

“What do you say we get Sammy and go watch a movie?” Dean asked.

(Y/N) smiled. “I’d like that.”

“Great! You go get Sammy and I’ll get the snacks.”

Dean turned and jogged out of the room. (Y/N) stood and tilted his neck from side to side, noting the small strain in his muscles. (Y/N) grabbed the back of the chair he had been sitting in, but stopped as he saw himself in the reflection of the small mirror. His eyes scraped over his body, from his head down to his exposed hips. He shifted so that he could see his torso from the side.

It was almost as if he was in a dream. Like, at any moment, he would blink and wake up in his bed with his breasts still attached to his chest. For years, he had been wanting to get top surgery, but it never seemed like something he was able to achieve. Never in his wildest imagination did he see himself standing in front of a mirror and feeling proud of the body that he stood in. He no longer saw the body of a woman, the man he was trapped inside and desperately attempting to claw his way out. He saw a man, who he truly was, the real (Y/N) Winchester.

And as he stared at his chest, a smile appearing on his lips, the words Dean spoke echoed in his head;

I’m proud to call you my baby brother.

Now, (Y/N) Winchester could confidently say that he was the luckiest man alive.

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panic-in-the-multiverse · 1 year

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Spider Infestation

Pairings: Dean Winchester x teen!reader (brief mention of Sam)

Imagine: being scared of spiders is not fun, especially not when they appear out of nowhere

Warnings: spiders, fluff, a bit angst? (Idk really), not proofread

A/N this is brought to you by the big spider on my wall that appeared out of nowhere scaring me to death (no for real my family literally ran to my room thinking I died or something)

Secondly this is short so sorry about that I guess but I had to write something to bring me comfort so this is what came from that, anyway enjoy. (I’m not actually scared of spider I just think they are disgusting, but I do however get scared when a spider appears out of nowhere when I turned back a second later)

A scream left your lips as soon as you saw the spider on the wall beside your head. You’d just been minding your own business as you readied yourself for bed, turned away for one second and when you turned back the scream left your throat before you could stop yourself.

You made a half sprint from your place by the bed, away towards the other side of the room while your eyes were still glued to the spider. You looked on in horror as the huge spider was about to crawl away. It’s big long hairy legs making invisible prints all over your wall.

Dean (followed by Sam) who’d heard the scream ran into your room gun in hand thinking it was a threat. He swung open your door, wide open and scanned the room for any kind of danger. Instead his eyes locked onto your scared form in the corner of the room. He lowered his gun and walked over to you slowly so as to not startle you.

“What’s going on?” His eyes looked at you in concern and when you didn’t answer he followed your eyesight and saw you were just staring at an empty spot on your wall. He’d think you’d seen a ghost had it not been for the fact that you weren’t the slightest bit scared of them.

“Hey kid, what’s going on” he slightly waved his hand in front of you to get you to look at him but it didn’t seem to work, he saw tears glistening in your eyes and got even more worried.

Slowly but surely you shook out of your fearful state and answered Dean's question with one word. “Spider”

The older hunter couldn’t help but let out a small chuckle as his face went into some kind of relief, and a small smile plastered itself on his lips. Thankful you hadn’t seen an actual ghost or something else that’d want to kill you, (though in your mind the spider was definitely out there to kill you).

Walking out of the room you stayed outside, Sam having long gone to sleep as he told Dean to deal with it with a tired yawn. Dean who as told to deal with the spider went and got some paper before he walked into your room to find the spider. When he found it he walked over to you with the spider and you whimpered away in fear and the grin that was plastered on his face as he brought the spider closer to you was quickly wiped of his face and he went to flush it down the toilet when you stopped him.

“No, don’t kill it!” Dean couldn’t help but to chuckle once more. For being so afraid of something you still seemed to not want to kill them. So instead he went over to the door and let the spider out.

When he came back once more he found you staring at yet two other spiders and he went through the procedure once more. Not long after that he went to his bedroom once more to get some sleep.

Your heart hammered in your chest as you later in your bed. You couldn’t sleep still thinking there were more spiders in the room. What if they were to crawl up in your bed and infest your blanket or start crawling over you. No you couldn’t be in your room for the night so you quietly went over to Dean’s room and knocked gently on the door. Hearing Dean’s voice grumble a tired come in, you opened the door and went inside.

“Hey”

“What do you want?”

“Can I maybe sleep in here with you?” Dean’s head lifted up from the pillow and he looked at you with tired eyes.

“Why?”

“I’m scared, what if there were more spiders or-“ you were cut off by Dean shuffling to the side of his bed and opening up the covers for you to get inside. Walking over to the bed you carefully laid next to him and he laid the blanket over you while also inviting you into a hug. You cuddled close to him and took in the comfort he offered. You were sure no spider would get you know.

#x reader #x teen #x teen!reader #x you #supernatural #supernatural x teen #dean winchester x reader #Dean Winchester x teen!reader #dean winchester x you #spn x teen!reader #Dean Winchester x teen #Dean Winchester x gn!reader #dean winchester x female!reader #Dean Winchester x male!reader

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wildgirllz · 1 year

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hi hello!!! i hope you're having a good day today! <3

i hope this isn't too specific, but can i request a dean winchester x male reader where they were childhood bEsT friends (they had the biggest crushes on each other but they could never admit it), but reader ran away from home when he was a teen and never got the chance to say goodbye to dean, and now dean and reader accidentally run into each other years later after they're both adults and on a case, and they have a mixed feeling reuinion because dean is OVERJOYED to see reader again, but also he is upset that reader never told dean where he was going, or even said goodbye? tysm <3

Ofc!! Here you go <3

Runaway

Word Count: 5k

Warnings: Angst, but a happy ending :)

It was just another day on the job for Dean Winchester, the hunter with the rugged good looks and the devil-may-care attitude. He had been hunting monsters with his brother, Sam, for years now, and while the work was dangerous, it was the only life he knew. He was good at it, and he liked the thrill of the hunt.

As he walked through the crowded city street, Dean felt a strange sensation in the pit of his stomach. It was a feeling he hadn't experienced in years, not since he was a teenager. He glanced around, trying to figure out what was causing the sensation, and then he saw him.

(Y/n).

Dean's childhood best friend. They had grown up together, spending countless hours exploring the woods and getting into all sorts of trouble. They had been inseparable, until (Y/n) had disappeared one day, without a word.

Dean had never been able to forget (Y/n). They had had a crush on each other when they were teenagers, but they had never been able to admit it. And now, here he was, standing in the middle of the street, looking just as handsome as ever.

Dean walked up to him, feeling a mix of emotions. He was overjoyed to see (Y/n) again, but at the same time, he was upset that (Y/n) had disappeared without a word.

"(Y/n)?" Dean said, his voice barely above a whisper.

(Y/n) turned around, and when he saw Dean, his face lit up with a smile. "Dean!" he said, his voice filled with surprise and delight.

For a moment, they just stared at each other, lost in memories of their childhood. Then, Dean spoke again. "Where the hell have you been, man? You disappeared without a word."

(Y/n)'s smile faded slightly, and he looked down at the ground. "I know," he said quietly. "I'm sorry. I didn't mean to just leave like that. I just... I had to get away, you know? Things were tough at home, and I needed to figure some things out."

Dean frowned. "What kind of things?"

(Y/n) shrugged. "Just... stuff. Family stuff. I don't really want to talk about it."

Dean nodded, understanding that some things were best left unsaid. "Well, it's good to see you again," he said, trying to lighten the mood. "What are you doing here?"

(Y/n) hesitated for a moment, as if he wasn't sure he wanted to answer. "I'm a hunter," he finally said. "I've been working on my own for a few years now."

Dean raised an eyebrow, impressed. "Really? You're a hunter?"

(Y/n) nodded. "Yeah. It's not easy, but I like it. It's... it's kind of like being a superhero, you know? Saving people, hunting things. It's a rush."

Dean chuckled. "Yeah, I know what you mean. I've been doing it for years."

They chatted for a few more minutes, catching up on old times and exchanging stories about their hunting experiences. Dean was glad to see that (Y/n) was doing well, but at the same time, he couldn't help feeling a twinge of hurt that (Y/n) had never reached out to him.

After a while, they parted ways, with (Y/n) promising to keep in touch. Dean watched him go, feeling a mix of emotions. He was happy to have seen (Y/n) again, but at the same time, he was hurt that (Y/n) had never told him where he was going, or even said goodbye.

As Dean walked back to his hotel, his thoughts were consumed by (Y/n). He couldn't believe that after all these years, they had run into each other again. It was like fate had brought them back together.

But at the same time, he couldn't help feeling angry and hurt. He had spent years wondering what had happened to (Y/n), worrying about him, and missing him. And (Y/n) had just disappeared without a word.

When he got back to the hotel, Sam could tell something was bothering him. "What's wrong, Dean?" he asked.

Dean sighed heavily. "I ran into (Y/n) today," he said.

Sam's eyes widened. "Really? How is he?"

"He's... he's good," Dean said, still lost in thought. "He's a hunter now, apparently. He's been on his own for a while."

Sam looked at him quizzically. "And that's a bad thing?"

Dean shrugged. "I don't know. It's just... it's weird, you know? We were best friends, and then he just disappeared without a word. And now he's a hunter, and I had no idea."

Sam nodded sympathetically. "I can see why that would bother you," he said. "But hey, at least you got to see him again. Maybe you can reconnect."

Dean snorted. "Yeah, right. Like he's just going to waltz back into my life like nothing happened."

Sam rolled his eyes. "Well, maybe he will. Or maybe he won't. But either way, you should try to make peace with it. Life's too short to hold grudges."

Dean nodded, knowing his brother was right. But it was easier said than done.

The next few days were a blur of hunting and killing, and Dean didn't have much time to think about (Y/n). But he couldn't shake the feeling that something had changed between them. They had been such close friends as kids, and now they were practically strangers.

It wasn't until they finished the hunt and were packing up to leave that (Y/n) showed up again. He was standing outside the hotel, looking nervous.

"Hey," he said, his eyes darting around nervously. "Can we talk?"

Dean hesitated, unsure. "I don't know if there's anything left to say," he said finally.

(Y/n) looked at him pleadingly. "Please, Dean. I need to explain."

Dean sighed heavily. "Fine," he said. "Let's talk."

They walked to a nearby park and sat down on a bench. (Y/n) took a deep breath and started talking.

"I know I disappeared without a word," he said. "And I'm sorry. But you have to understand, things were really bad at home. My parents were fighting all the time, and my brother was getting into trouble. I didn't know what to do, so I just... I ran away."

Dean listened, his anger slowly melting away. He could hear the pain and desperation in (Y/n)'s voice, and he knew that he had been through a lot.

"I didn't mean to hurt you," (Y/n) continued. "But I was scared, and I didn't know what else to do. And then, after a while, I was too ashamed to come back. I didn't know how to face you.”

Dean nodded, understanding. "I get it," he said. "But you could have at least told me you were leaving. I spent years wondering what had happened to you, worrying about you. And you didn't even say goodbye."

(Y/n) looked down at his feet. "I know,"

There was a moment of silence between them, and Dean couldn't help but feel conflicted. On one hand, he was glad to finally have some closure and hear (Y/n)'s side of the story. On the other hand, he was still hurt that (Y/n) had left without a word.

"I'm sorry," (Y/n) said softly. "I should have told you. I should have said goodbye."

Dean took a deep breath and looked over at his old friend. He could see the sincerity in (Y/n)'s eyes and knew that he meant what he said.

"It's okay," Dean finally said. "I forgive you."

(Y/n) looked up at him, relief flooding his face. "Thank you," he said.

They sat in silence for a few more minutes before (Y/n) spoke up again. "I missed you," he said softly. "A lot."

Dean felt his heart skip a beat at the words. He had missed (Y/n) too, more than he had ever let himself admit. They had been each other's confidants, each other's first crushes. But things had changed, and they had both gone down different paths.

"I missed you too," Dean finally said, his voice barely above a whisper.

There was a moment of silence between them before (Y/n) spoke up again. "I know we can't go back to how things were," he said. "But... maybe we could try to be friends again?"

Dean thought about it for a moment before nodding. "Yeah," he said. "I'd like that."

(Y/n) smiled, and they sat in comfortable silence for a while longer. Dean couldn't help but feel a sense of nostalgia wash over him as he sat there with his old friend.

As they got up to leave, (Y/n) turned to him. "Hey, Dean?" he said.

"Yeah?" Dean asked.

"Thank you for forgiving me," (Y/n) said. "It means a lot."

Dean smiled at him. "Of course," he said. "We were always meant to find each other again."

(Y/n) smiled back at him, and they walked back to the hotel together. It wasn't a perfect reunion, but it was a start. Dean knew that there was still a lot of healing to be done, but he was willing to try. He had missed (Y/n) too much to let him go again.

#supernatural #spn #dean winchester fanfiction #dean winchester fic #dean winchester fluff #dean winchester x reader #dean winchester au #dean winchester smut #dean x reader #Dean Winchester x male!reader #Dean Winchester x m!reader #dean winchester x male reader #dean winchester x you #dean winchester #dean winchester angst

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bitchinfawkseh · 9 months

Text

NSFW Dean Winchester Headcanons (Male Reader)

A/N: ahhhh this is a req from tiktok 🤤 yes ik this is short I just wanna see how well it does before I do more <333 thanks bbs

• ok first off he's constantly grabbing ur ass when he's in the mood don't matter when or where

• horny little shite

• likes it a LOT when he gets to blow you. Your face really gets him hard

• he's a switch def but prefers to be sub/bottom I think

• he loves to whisper dirty shit in your ear when he's fucking you... stuff like "You're such a good boy", "you look so hot with my cock stuffed in you." YEAH DIRTY BOYYYYY

• likes to film u (with consent ofc) while you give him bjs

• most vocal man you've ever met

• he likes handies in the shower whether that's giving or receiving.

• he's a very generous lover doesn't matter gender or sex you are

• he likes eating pussy and sucking dick what can I say

• I see u my fellow trans guys💪

• I think he likes to have his hands restrained with handcuffs or something as you give him blowjobs. Something about not being able to touch you drives him NUTSSSS in a good way

• he's bi we all already knew this so even if you are genderfluid I promise u he does not care

• if u are trans and have gone on T and like have the little pp. He still sucks that shit UP like it's his morning coffee

• u don't drive Baby but ya sure as hell blow him as he drives down the highway

#dean winchester headcanons #dean winchester x you #dean winchester x reader #dean winchester x male!reader #dean winchester headcanon

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justonemoregayboy · 2 years

Text

Morning teeth brushing routine

Dean Winchester x Male!reader

Warnings:Smut

word count: 2520

requests are open🖤

English is not my first language sorry if there are spelling mistakes enjoy reading.

Getting out of bed, Y/n changed into just a set of small briefs that barely covered his bubble butt. Even with Sam being out on his daily routine of running and Jack heading out with Castiel to investigate anything that caught the nephelim's attention, he still wasn't alone in the bunker. And he couldn't walk around with nothing but a smile.

Speaking of which, just like his big worked breasts, his smile was something he cared about a lot. His first stop after leaving his bedroom was the bathroom. After a quick brush of he tousled hair from his face, the next brush he picked up was for his teeth. With some toothpaste he went to work diligently maintaining his beautiful smile.

The bedroom door at the other end of the hall opened. A mature man walked down the hall to the kitchen to eat breakfast. He walked past the bathroom door and paused for a moment, seeing Y/n on the bathroom counter in he underwear.

Breakfast could wait.

Y/n glanced out of the corner of his eye as the man's reflection appeared in the large mirror in front of him. The defined contours of his muscular body suited he in he job as a monster hunter. His eyes swept over his washboard abs to see that he too was wearing only his underwear. The material of his briefs tightened as he struggled to contain the other impressive attribute of his. He couldn't be more excited to get up close and personal with the hot Dean Winchester.

Like most fucking hot men, Dean had a nearly insatiable libido. Lately, the restrictive nature of his job made it difficult for him to find a good hole that he could regularly drain that beast into.

Y/n's eyes followed Dean as he walked behind him. While he was still brushing his teeth, he wordlessly slid his thumbs into the hem of his briefs just enough to expose his privates. A small rope of arousal from him clung to he crotch. He had been anticipating this, and it was already pretty wet down there.

He knelt down and grabbed his ass with both hands, parting his boy pussy with his thumbs and giving him a long, slow lick. It wasn't meant to be a full course of foreplay. If he had woken up a little later and caught him at the breakfast table, it would have been a different story, as he would have crawled under him to grab his own breakfast. With a mouthful of toothpaste and his mouth probably sporting morning breath, this was merely a polite good morning kiss to his little hole.

He stood up and pulled his boxers down far enough to let his angry morning wood spring freely against Y/n's ass cheek with an audible thud. He held the thick girth of his shaft in his hand and guided the tip to the slippery underside of him, rubbing it up and down to lubricate himself well. After briefly teasing him, he slid into him unceremoniously. He put he hand on his hips and pulled Y/n toward him as he thrust into him, filling him with the full length of his cock in one fluid motion.

Y/n felt butterflies in he stomach. Even though it was something he had come to expect, nothing could really prepare him every time he felt him filling he completely. It was never hard on him. At least never too abrupt. He didn't crash it. But still he grunted involuntarily as he was thrust into he fist, thrusting that big cock against his sensitive prostate, literally taking his breath away for a moment.

He held it there until Y/n could get used to the size of him inside of him. Once he started breathing again, he began to move in and out of his ass, slowly and tenderly, pulling and pushing into that tight hole. His strong hands moved from holding his hips along his toned body to his chest, cupping them with a firm grip as he played with his sensitive erect nipples.

Feeling Dean in heat now, he vividly remembered the first time.

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It was a morning like any other. Dean found him on the bathroom counter brushing his teeth, both of them in their underwear. He greeted him silently with a hug from behind him, wrapping his arms around he waist, pulling him close. He could feel the size of his hard morning wood like steel wedged against his butt. It was a game he liked to play, to see how far he could push his limits before he pushed he away. Usually a firm elbow to the ribs was enough to send him off without any resistance.

But for some reason, this time, Y/n didn't. Maybe it was because he knew there was something very big inside those underwear burning for him. Maybe it was because it was that time of year when he wasn't thinking clearly. But whatever it was, a part of him was genuinely curious as to how far it would go. He allowed his embrace to linger.

Emboldened, Dean caressed the back of his neck and he moved his hips, rubbing against Y/n, sliding his shaft up and down between his cheeks through the thin fabric of his boxers and his cheeks from Y/n's tiny underwear. One of his hands moved up the length of his body to the bottom of his chest. He must have expected him to push him away for that. But I never arrive. His hand slid up to cup his chest through the skimpy shirt that barely covered him. His finger found and circled the tip of he nipple immediately. It was easy for him to find it, digging hard against the material of the garment. His thumb joined he, giving he just the lightest of pinches.

It was no longer a mere hug, a careless touch that they could both dismiss. It was clearly obvious to both of them the sexual nature of this embrace. They both knew it. And they both knew the other knew it. And yet, Y/n didn't try to stop him. Instead of startling him to his senses to redouble his resistance, he found himself melting into his embrace.

He hips grinding against him moved in longer strokes. He couldn't see it, but he could feel the bare flesh of his penis protruding from the top of his boxers against the base of his butt. He was so focused on the sensation that he almost didn't notice his other hand slipping its fingers into his underwear. But feeling his finger sliding into the top of his hole was a sensation he couldn't ignore. But he didn't want to anymore. His body shuddered as he felt he finger encircle his orifice. The strength in his arm bracing against the bathroom counter failed and he fell forward onto he elbows, and he moved with Y/n.

Dean took that as a sign. His hand in his underwear pushed he down to the middle of he thighs.

Y/n looked at the mirror. His muscular body towered over him. He had strength, yes. But he too. And between the two of them, he was much stronger if we talk about combat. If he wanted, he could take it right now, whether he allowed it or not. The idea scared and excited him.

If he told he to stop, he wondered if he would. He surely would, he always stopped first. But a part of him feared that this time he wouldn't. But a bigger part of Y/n was afraid that he would. And so he fell silent.

Behind him, he erection was almost completely out of he boxers. With he hand free of he, he angled it down between he legs before wrapping he strong, muscular arm around him again, holding him tight and teasing he breast again as he thrust. The side of he shaft slid against he boy pussy, surprising them both with how wet he had become.

He hand playing with his on he cock hadn't stopped as he continued to stimulate him more and more. He muscles were putty on he hands. He mind was a misty haze of excitement. He ability to even defend self was useless. And with the bulk of him pinning him against the bathroom counter, and the feel of his teeth against he neck, he was completely helpless to stop it and he knew it.

He hand playing with his cock moved between he legs to point he cock up. The tip pressed against the entrance of his boy's pussy and he stopped, froze, absolutely still.

Y/n looked at him in the mirror. His entire body was shaking as he gasped with animal lust. From the moment he first started up, he buried his face in he hair, inhaling the heady musk of a whore in heat. And now, in this final moment when he would be most lost in his instincts, he looked up from the nape of his neck to his eyes in the mirror.

He face was flushed with excitement, as much as his. His eyes were narrowed with lust, but in this moment of clarity, he could see that they were also tinged with fear. For a few seconds, he looked at he and Y/n looked back at him. It was clear that he loved him. He wanted him so much that it hurt he, even now, to deny self. But he realized that he was waiting for he permission.

Y/n could say no, and he would stop. He knew that he could. That it would be the right, albeit cruel, thing to do. As the arduous seconds passed, his eyes sparkled. There was no yes. And the cold sobriety of what he had done, of what he was about to do, with his best friend no less, had begun to sink in.

But just when all hope seemed lost, Y/n gave Dean the slightest nod. His Dean's face lit up with the joy of every morning and birthday and Christmas party combined. His arms wrapped around him and he hugged him tightly, pulling him to him as he pushed self into Y/n.

That was the first time Dean took his breath away. He wasn't used to such length and girth stretching him out so completely. Not that he hadn't had big cocks inside him before, no way. But Dean had certainly gotten the best of the Winchester genes. And something else . He took a bit of work, a bit of time and patience on both sides, but the depths of him managed to stretch enough for him to wield. Through his efforts, they treated him to feeling his heavy balls against his stretched hole every time he bottomed out with him.

Dean pressed his face against the back of his hair again. Not to enjoy his scent, but to hide his face. But it wasn't enough to quell his desperate, cathartic moans as he finally managed to get him into heat after so long. It broke he heart to hear it. If his back was turned, he would have hugged he back.

While he had waited for this moment, now he just wanted it to last forever. But it wasn't going to be. The sensation of Y/n of him coming increased the pressure around his cock, the massaging squeezes milking him for all he had, and the wetness dripping down his legs was too much. That, coupled with the wet sounds of his hips bumping rhythmically, accompanied by Y/n's moans in lustful passion, was a symphony of pleasure beyond compare. He could not stand it any longer.

He wielded it one last time. Y/n's eyes widened. As with so many things, he should have expected this, but he wasn't ready for it. His hand cupped his belly and the bulge in his abdomen swelled as he felt the tip of him widen, deep inside him. His embrace tightened, pulling him against him harder than ever, pressing the tip of him against his prostate, battering it as hard as he could. He felt his shaft throb and pulse as he pumped load after load, delivering it deep inside Y/n, with nowhere else to go but straight through he rectal canal, flooding he belly with a torrent of thick, pent-up seed of Dean who seemed to want to be able to raise him until he was pregnant with his baby.

For a long time, they stood together like this, panting and coming down from the euphoria of their shared climax. Neither of them could hardly believe what had just happened. Each wondered and worried if the other was upset or sorry. But once Dean was physically calm enough to back away, they had a long talk about consent and boundaries for next time. It was too many small potatoes for Dean to accept. All that mattered was that there would be a next time. And some time after that. And some time after that.

----------------------------------➸-----------------------------------------

So it was. And while it became as much a part of his morning routine as brushing his teeth, it never stopped being special. He looked at self in the mirror and Dean looked back at he, meeting he eyes, watching them flutter every time he trembled from coming so hard. Especially when he came at the same time as Y/n. They had gotten pretty good at it. He loved feeling Dean come deep inside him.

As soon as Dean finished, he backed away carefully so as not to let he get away. He pulled up his underpants as they were before they got there. He gave he a sweet kiss on the cheek before heading downstairs to make them breakfast while Y/n finished brushing. Y/n put he palm to he belly. He would get to feel a part of him inside he while he wasn't at work for the day. And just like brushing his teeth, he always left him with a beautiful smile.

Dean carried out his duties with a clear head, which allowed him to improve his hunts quickly while the other men in the bunker didn't understand why he was always so relaxed. And Y/n could be as happy as ever at home with his friends, feeling no resentment for being physically neglected. As per his wishes, he never told anyone who was the boy who made him practically glow when they all got together for dinner. But everyone could clearly tell that he was happier than he had been in a long time. For everyone, it was enough just to see him smile.

After all…

It was the prettiest thing he could wear.

#dean winchester x male reader #dean winchester x male!reader #male reader #male reader insert #supernatural x male reader #spnfamily

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deansfleshlight · 1 year

Text

okay so hi i just wanna put this out here. i joined the fandom mid 2022 and fell in love with dean. i dont really ship him w anyone in canon but i do love some destiel fanfics, i read a lot of em. tho i read dean x reader fics more. i dunno why i wrote this anyway but uhh well i need some help. i actually kinda prefer dean topping when im reading destiel fics or a dean x omc fics because i personally think that him bottoming is a little out of character, which is fine if u disagree ig its just me i dunno. well idk but i think ive ran out of bottom!cas x top!dean fics to read on ao3 so im asking for help. i already got a lot of hate from twitter because of this preference but umm well be kind pls im so bad at this😭

#dean winchester #castiel #deanncastiel #deancas #dean and cas #dean winchester x male!reader #dean x reader #top!dean #bottom!cas #bottom cas #top dean #top dean winchester #bottom castiel #fanfics #fanfiction recommendation #supernatural #spn fanfic #spn

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l1tw1ck · 4 months

Text

bottom Dean x dom!top!amab reader

started watching supernatural and good lord they are hot. only writing for dean and sam atm, only on s2

cw: nipple play, orgasm denial, begging

It was late at night, so dark that Dean had to walk around the house with his lighter. He's staying over at your place while he hunts down another creature. He couldn't sleep so he's getting a glass of water. He thought he was being quiet but he thought wrong, he jumps when the light turns on. "Can't sleep, Dean?" You smile.

"Guess not. Didn't mean to wake ya."

"It's fine." You slowly walk over to him, towering over his slightly shorter frame. He leans back into the sink, intimidated for some reason. "I know a way to help you fall asleep."

He knows exactly what you mean. "Be gentle." He smirks.

Dean grips the edge of the sink and leans his head back, mouth agape as you bottom out inside him. You're bigger than anything he's ever taken. He's only used his fingers but still. "Fuh- fuck–" He moans.

"Am I too big for you, baby?" You tease him, sneaking your hands up underneath his shirt to play with his nipples. Dean gasps in shock, ass squeezing your cock in pleasure. "Oh, you like that?"

He grips the sink harder, a short and strained whimper leaving his lips before he bites on the lower one. He feels good but he still has pride.

"Don't be shy," You slowly pull out before slamming into him. He can't help but let out a loud, slutty moan. "I wanna hear you, Dean."

Dean moans uncontrollably as you roughly fuck him, his pre cum dripping onto the floor and a string of curses leaving his pretty wet lips. "Shit!" He cries out, your cock hitting his prostate. "There! Right— fuck~!"

"You wanna come, Dean?" You grip the tip of his cock, preventing him from getting release. "Beg for it. Beg for me to let you come like the whore you are."

"I'm no- not a whore!"

"No? Then why are you taking my cock like you are?"

He whimpers again. His pride isn't worth it. He wants needs to come. "Ple- please! Please let me come, [Name]~! I wanna come~!"

"Good boy." Dean comes right when you release his cock, cum splattering all over the cabinet and floor.

#wicks🕯️shorts #top male reader #male reader #dean winchester x reader #dean winchester x male reader #bottom dean winchester #bottom male character #supernatural x male reader #supernatural x reader #🕯️supernatural

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godjustkys · 1 month

Text

| mdni 18+

| SUPERNATURAL headcanons

please give requests.

-----------------------------

RATED: NSFW

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STATUS: You're already in a relationship.

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Request: none, I wrote it myself on February 23rd.

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Dean:

1 - He might not admit it, but god does he love being bent over;

2 - He is SO FUCKING LOUD. When he's on top, he mostly groans, occasionally moans, but when he's on bottom,, the whimpers, whines and moans that escape his mouth is unbelievable;

3 - Praise him and he's on his knees for you;

4 - If you EVER put on a cowboy costume and you have the cowboy boots on... he's hot and bothered the moment he lays his eyes on you;

5 - LOVES pulling on your hair during intercourse;

6 - If the two of you are having sex and he's overwhelmed, he'll grab a pillow to hold onto or grip the sheets;

7 - You two have fucked in the back of Baby.. per Dean's request.. (surprisingly.);

8 - Once, in the heat of the moment, you started facefucking Dean while he was giving you a blowjob and ever since that happened, it's been his favourite thing about sex;

9 - You manhandling him is his guilty pleasure;

10 - At the start of the relationship, Dean believed that it would kind of be a switch-switch situation during sex. When you fucked for the first time, Dean was riding you and his legs started shaking. At that moment, he was thinking about getting off of you, but when you grabbed his hips and made him ride you up until the end, he gave up on that thought.

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Sam:

1 - He is not loud at all. Sure, a couple moans here and there but it's mostly just heavy breathing or grunts. Unless he's overstimulated;

2 - Whenever he's horny, he won't make it clear to you. He just gets all grumpy and grouchy;

3 - Unlike Dean, when he's overwhelmed, he'll hold onto you. And he'll scratch the living hell out of your back;

4 - If you mess with his hair during sex, so much as pull on it, he will moan;

5 - Once, when Sam got back from a hunt with an unconscious Dean, you scolded him and he got hard. (involuntarily);

6 - Sam insisted on trying mirror sex - lo and behold, he had his face buried in the sheets for the majority of it (when you didn't hold his head up). Why? He was embarrassed;

7 - During a hunt, Sam got really grumpy. You had to do something about it because Dean's taunting demeanour would set him off immediately, so you just dragged Sam into the bathroom, when Dean was out, for a quickie. It worked wonders;

8 - You had a habit of not caring about shortness of breath when kissing, so when you first made out with Sam, he thought he was gonna pass out. (He was overreacting, he was nowhere close to passing out);

9 - He LOVES it when you're bold and straightforward, it turns him on so much;

10 - His whole body starts shaking due to pleasure if you focus on his chest and neck too much.

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Castiel:

1 - If he's in the mood for it, he won't tell you. He will just stare at you until you figure it out yourself;

2 - If there is a moment when Castiel doesn't put his hands on your chest or stare at it, consider it a miracle;

3 - He cannot comprehend why he can't form coherent sentences during intercourse. He says "it must be some kind of curse". In reality, he's just too into it to care enough about speaking properly, but he does not realize it;

4 - Castiel does not realize how much you being rough with him turns him on. Degrade him for a couple seconds and he's hard;

5 - During sex, he holds onto you so tightly with his hands that a lot of the time, they leave bruises. Once, he noticed them and asked what happened. When you told him that they were from him, he just looked at you confused and said: "I never hit you?";

6 - Even though you being rough riles him up a lot, he prefers soft and gentle sex.

7 - When the four of you, you, Sam, Dean and Castiel were riding in Baby (you and Cas in the back seat), you decided to just lay your head in Castiel's lap and get comfortable. He was your boyfriend after all. It was fine at first, you even closed your eyes. Then suddenly, Castiel pushed you off. You sat up looking at him puzzled. He just gave you glare as he looked out of the window and covered his crotch. (Inconvenient places to get hard #2);

8 - He knows how mad it drives you when he gives you that soft innocent look during sex, it just makes you want to go rougher on him;

9 - He once asked you to 'rail him' without knowing what it meant. When you explained it to him, he replied with "oh, okay. So will you?";

10 - He finds your hands (minus your chest) the most attractive thing in the world. He WILL stare at your hands during intercourse because he wants them on him 24/7.

-----------------------------

A/n: if you want any of these headcanons to be made into a oneshot, please let me know. <3

#male reader #top male reader #dom male reader #fanfic #fanfiction #supernatural #dean winchester #castiel #sam winchester #dean winchester x reader #dean winchester x you #sam winchester x reader #sam winchester x you #castiel x reader #castiel x you #headcanon #request

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dilfstrap · 20 days

Text

humming like a car engine

dean winchester x gn reader

feminisation, pet names, degredation, thigh fucking

'how you doing pretty girl?' you whispered and gripped dean's chin, tipping his head up so he met your eyes. normally bright green, they were currently nearly glazed over and half lidded with pleasure. he was taking it like a champ: the slide of your dick between his thighs, fucking those muscular legs like they were the pretty little pussy you knew he wished he had.

his response was a near unintelligible moan, impossible to make out any words as he let more drool dribble down his chin. you pressed the heel of your palm into his dick and bit your smile into the smooth flesh of his shoulder at the high keening sound he let out at the feeling. his hips pressed hard up, back arching. you groaned and fucked into that lube slick space harder and faster, hand crushed between you, 'you like it when I play with your clit, babygirl? like when I make you get leaky and wet for me? it doesn't take much...'

dean's head lolled back, hitting the mirror above the sink he was propped on, and if he wasn't already garbling out a cry as his cock spurt more precum over your fingers, you would wince at the bang.

his fingers tightened and dug hard into the muscle of your shoulders, his legs clenched together like the good girl dean was clearly trying so hard to be, and you kissed him sweetly. your mouth caressed his for a moment before dragging through his drool to murmur in his ear, unsure if his fucked-dumb brain would even understand, 'cum for me then slut, like the desperate bitch you are.'

clearly, he did understand because his back arched again, and he rut his leaking pole against your hand like a puppy in rut. his mewls of pleasure had turned to sobs some time ago, but now they were nearly howls. his whole body tensed up all over and then he was gone, limp and loose as he spilled cum — thick and white — between you.

all the tension that had been building, and all the desperation that had built up in dean's body had left, but the hazey look didn't fade as a clumsy, dick drunk hand fumbled to smear over his stomach and reach between his own legs to fist your cock.

'so wet for you, jesus, so-' his voice trailed briefly into nothing but airy keening- 'fucking me so good.'

#mdni #usft #top male reader #sharkie writes #male reader #top reader #dean winchester #dean winchester x reader #dean winchester x male reader #dean winchester x top reader #dean winchester x gn reader #supernatural #supernatural x reader #supernatural x male reader

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pinkiebieberpie · 10 months

Note

omg THANK YOU SO MUCH for this -> ( https://www.tumblr.com/pinkiebieberpie/723937177190416384/yay-im-glad-to-hear-you-also-do-x-male-reader?source=share )!!!!!! i really do love it, tysm 🥺 it was really cute 💕💕💕 can i request a sequel to it with dean + reader adjusting to being together? since it's prolly a whole new thing for the both of them. again thank you!!!! ilysm 💕💕💕💕 - 🐊

i'm so happy you liked it!! 🩷🩷

dean would be so nervous but also so excited,

he doesn't want to mess something up in this new relationship,

because you are childhood friends he feels comfortable with you but at the same time he sometimes would be like "wait, can i kiss you?",

he needs reminders that he is loved and appreciated 🥹,

dean would organise so many dates, like official dates, because he wants to feel like "we are boyfriends, not friends anymore!",

little touches all the time!!

he is a little bit nervous with you around people, but only because it's something new,

also a lot of talking about this new relationship, about your needs and plans for your future,

sam is your biggest supporter, we love an ally younger brother!!

at the beginning of your relationship you have a lot of AND I MEAN A LOT OF late night drive dates, so you can eat burgers in the impala and talk about everything and anything;

supernatural masterlist

#dean winchester #supernatural #jensen ackles #dean winchester fic #dean winchester headcanon #dean winchester angst #dean winchester fanfiction #dean winchester x y/n #dean winchester x male!reader #dean winchester x you #dean winchester ff #dean winchester fluff #dean winchester supernatural #dean winchester spn #dean winchester smut #dean winchester au #dean winchester blurb #j's 🐊 anon

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supernaturalscribe67 · 9 months

Text

The Secrets We (Don't) Keep

Words: 7,314

POV: 1st & 3rd Person

Pairing: Dean/Sam Winchester x Brother!Reader [Platonic]

Warning(s): Language, Fluff, Mention of John Winchester, Mention of Childhood Abuse, Awkward Moments

Summary: After finding out that his brothers, Sam and Dean, read the first entry of his journal, the reader decides to take a rather creative approach to his payback.

Request:

i’d love to see you continue with that winchester brother reader! or something similar? your writing is very comfortable to read :)

@stklett

@xdark-acadamiax - (Tagged because I saw how much you loved this idea!)

A/N: I really hope you guys enjoy this next part! I can honestly admit some parts make me laugh so I hope they make you guys laugh as well! Feedback is greatly appreciated!!!

~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.

OCTOBER 2014

I don’t know why I thought I was going to be able to keep this journal private. I guess my expectations were too high. How dare I assume that Sam and Dean would respect my privacy? Of course, they wouldn’t. How dare I presume that hiding this thing between my mattress and boxspring would be a good idea? I mean, who in their right mind would hide something there? Everyone looks between their brother’s boxspring and mattress!

Silly me.

But, since I found out my brothers decided to read through my first entry (and ultimately vandalize my journal), I have done some brainstorming. Brainstorming ways that I can get back at them. I've considered the classic pranks to start with; itching powder in their underwear, hair dye in their shampoo, Nair in their body wash, or even putting laxatives in their coffee. All of these pranks have been used by all three of us multiple times. Even with some thinking, I’m still unable to come up with a prank that I feel would be good enough to teach them a lesson.

So, I’ve come up with the next best thing.

In this entry, I’m going to be writing down some of Sam and Dean’s embarrassing moments.

Throughout our decades of life, all three of us have had our fair share of shameful moments, but the instances that I am thinking of are ones that I like to bring up from time to time. Each time I mention them, I get an eye roll from Dean and one of Sam’s classic bitch faces. It’s always so satisfying to get that kind of reaction from them.

It would only be fitting to see what kind of reaction I get when they eventually read this entry.

JUNE 1989

Everyone has their fears. Some people’s fears are more valid than others. Sam has a fear of clowns, I have a fear of needles, and Dean has a fear of planes. I can understand Sam’s fear of clowns - Plucky Pennywhistle's always made me uneasy when I was a kid - and, as far as my fear of needles, have you seen some of the needles that doctors use on patients? They’re HUGE! No thanks.

What a lot of people don’t know about my older brother, however, is that he didn’t just suddenly have a fear of planes. He didn’t wake up one morning and discover that he didn’t like flying. Sam’s fear of clowns developed from our times at Plucky Pennywhistle’s, my fear of needles stemmed from an unprofessional doctor (who shouldn’t practice medicine anymore, in my opinion) from my second round of childhood vaccinations, and Dean’s fear of flying…well…

Dean used to be afraid of heights.

I say ‘used’ to be because, if he still has that fear, he does a really good job at hiding it. We’ve gone to some pretty high places on our hunts, and, from what I noticed, it never seemed to bother him. He could always be masking it well enough, which is possibly the case. Then again, he could have learned to deal with the fear and forget about it completely. Lucky him.

But, when Dean was younger, that was one thing that he was never good at doing - masking his emotions - especially when the three of us were by ourselves. When it was just us three, Dean felt like he could express how he truly felt about anything and we would keep it just between us. It was a little 'brother code' that we had going. Whatever was said between us was kept between us. Kind of like Vegas, in a way.

What happens in Vegas, stays in Vegas.

I’ve always wanted to visit Vegas.

Stay on topic, (Y/N).

For most of our young childhood, we spent half the time traveling with our father, and the other half at Bobby’s. I always loved going to Bobby’s house. It felt like a home. To me, it was always my home growing up, even if I wasn’t there all the time. Even though we stopped going there as often when we got older, it was still the place that I would technically consider my home. We had the most fun there. We felt like we could be kids for once. Like we didn’t need to worry about the things that went bump in the night anymore.

I loved Bobby’s house.

We were there during summer vacation, which was somewhat of a common occurrence when we were younger. Sam, Dean, and I always found things to do while we were there, and playing throughout the maze of cars in Bobby’s junkyard wasn’t unusual. Normally, we would play hide-and-seek, tag, have races, or some stupid war games that we would come up with.

That day, however, we discovered a new stack of cars, about six cars high in total, that we had not previously known about near the far backside of the property. We would have usually stayed towards the front, but, that day, we decided to roam around. Dean had the expert idea to see who could climb the highest. Sammy went first, climbing on top of the first car with some help before he got nervous and backed down. I managed to make it up three cars before I decided that I had enough and came back down. Dean, on the other hand, took the challenge a little too seriously. He didn’t waste any time reaching the car that sat on top of the pile. He was so proud of himself.

It all went downhill after that…

“Ha! I beat you both!” Dean exclaimed as he stood on top of the roof of the car, fists balled up and placed onto his hips in a mock Superman pose. “I’m the King of the Cars!”

(Y/N) rolled his eyes and crossed his arms over his chest. Sam pouted as he looked up at Dean, his bottom lip pushed out.

“I wanna get up there,” he said, letting out a small whine.

“You tried to get up there, Sammy, but you said it was too high.” (Y/N) explained, looking down at him.

Sam hung his head as he kicked a pebble on the ground. Dean still stood on top of the car, waving his arms around. He let out quiet, faint shouts as if mimicking a cheering crowd. Sam pursed his lips ever so slightly.

"I wanna play hide-and-go-seek."

"It's ‘hide-and-seek’, Sammy." (Y/N) deadpanned.

"That's what I said."

"Do you wanna play with just you and me?"

"No," Sam shook his head and glanced up at his oldest brother, who was still cheering for himself. "I want De to play."

(Y/N) gave a short nod before he turned to his older brother as well. He reached up and cupped his hands to the side of his lips. "Hey, idiot! Sammy and I wanna play hide-and-seek! Get down here so we can go play!" He called up to Dean.

"You guys are just jealous because I could climb up to the top!"

“No one’s jealous of you, Dean! We just want to play! Come on!” (Y/N) let out a groan as he placed his hands on his sides.

Dean scoffed and waved him off. “Yeah, yeah, I’m coming.” He mumbled as he walked closer to the edge of the car.

As Dean gazed down at the ground below, he froze. His eyes went wide and his legs and arms tensed. The confident smile that he had once had on his face was now gone, replaced by an uneasy frown. (Y/N) and Sam’s eyes were on him, watching him intently, waiting. After a minute or so of Dean standing there, not moving, (Y/N) shook his head and cupped his hands around his mouth again.

“What are you doing?” He called out.

(Y/N)’s voice caused Dean to jump and turn his gaze towards him. He opened his mouth, attempting to speak.

“I-I can’t get down,” Dean said with a shaky tone.

“What do you mean you ‘can’t get down’?”

“I can’t get down! I-It’s too high!”

“You were the one that wanted to get up there!”

“I know I was, will you just shut up!” Dean’s voice came out cracked and high-pitched.

(Y/N) closed his mouth and stood there, watching as Dean struggled to get down on his knees. As he attempted to move his leg down towards the trunk of the car, he felt the car shift. (Y/N) and Sam jumped when they heard the metal scrape against the car below. Dean let out a yelp and pulled his leg back. His fists were clenched onto nothing, knuckles a ghostly white color. His face was noticeably red and tears began to form in his eyes.

“G-Go get Bobby!” Dean called down.

“You can get down, Dean! You’ll be okay!”

“No! I’m not okay!” Dean let out a sob. “It’s too high! The car’s going to fall. Go get Bobby,” Dean’s voice was as shaky as his hands were.

(Y/N) looked down at Sam. “Go get Bobby, Sammy.”

Sam’s eyes were wide with worry as he nodded slightly. He turned and made a mad dash towards the house. “Bobby! Bobby!” He cried out.

(Y/N) then turned his attention back to Dean, who seemed like he was seconds away from having a breakdown.

“Dean! You’re going to be okay! Just come down the same way you went up.”

“N-No!” Dean shook his head rapidly.

“Quit being a baby!”

“I’m not a baby!”

“Then why are you crying like one!?”

“Will you shut up!?”

(Y/N) stopped talking and let out a huff. Not even a minute later, Sam came running out towards them, Bobby quickly behind him. Bobby ran his fingers through his hair stressfully.

“What the Hell have you idjits done?”

It took thirty minutes of coaxing for Dean to be able to climb down two of the cars before Bobby had to make his way towards him and carry him down the rest of the way. Needless to say, Dean wasn’t in the mood to play any type of game with us after that, especially when I began to tease him mercilessly about his crying. I still tease him to this day about it, comparing him to a cat that had been stuck in a tree. Bobby was known as ‘Firefighter Bobby’ for a good month-and-a-half after that.

We were forbidden from climbing on the cars anymore, which none of us seemed to have a problem with. As for my teasing, I had managed to get in trouble with Bobby once he caught me and was forced to help him organize the study while Sam and Dean went out to play. It wasn’t very fun, at the time, but I had learned a lot more about hunting during that punishment, so some good came out of it.

To this day, Dean still likes to pretend as if it never happened. Or, if it did happen, then it was either Sam or me that needed to be rescued. Not him. He never needed to be rescued (according to him). Still, Sam and I can remember this vividly. It’s two against one, Dean.

So much for ‘King of the Cars’.

OCTOBER 1989

Sam was always gullible when he was a kid. He grew out of it in his early teens and became more aware of how deceitful people could be. Before that, however, he was fun to mess with. I’m his big brother, I have a right to mess with him.

I still do, but it’s not as easy.

Sam was the type to believe anything that anyone wanted to tell him. Even if it was the most outlandish thing possible. I was able to convince him that unicorns were real and that everyone got one when they turned ten. When he asked Bobby what kind of unicorn he had gotten for his tenth birthday, Bobby told him the truth right then and there. He was so disappointed that he didn’t talk to me for about a week. I felt bad, at least a little bit. But the other part of me thought it was the funniest thing I had ever done to him at the time.

That was when he was four.

I still ask him what he wants his unicorn to look like.

He hasn’t given me a straight answer yet.

Around the age of six, Sam had started to let his hair grow out. Granted, everyone’s hair was growing out at that point - my father had neglected to get us any type of haircut for a little over six months - but out of all of ours, Sam’s was the longest. Dean had started calling him ‘Samantha’ at some point, which irritated Sam to no end. I decided to take a different approach, however.

Back then, we knew about monsters. We knew about the different kinds of monsters that our father fought but didn’t know a lot about them. We knew their names, what they looked like, and common signs for each of them. One thing we didn’t know about certain monsters was how people were turned into them.

So, with this limited knowledge in the back of my head, one dreary fall night, while our father was away on a hunt and Dean was out finding us some food, I decided to play a little…prank, if you will, on Sammy.

Sam’s eyes were glued to the television screen. A rerun of Alf played that he was completely enamored with. Meanwhile, (Y/N)’s eyes were attached to something other than the show. He watched as Sam brushed his long locks out of his face occasionally. Sam tucked some hair behind his ear, but it didn’t stay there long before it fell in his face. His hair was down to his chin by then and (Y/N) had to admit that he was more irritated about the length than Sam was.

When the show moved to a commercial break, Sam clenched his eyes shut and stretched his arms over his head. He glanced over at (Y/N) and furrowed his brows.

“What’re you looking at?”

“That hair,” (Y/N) gestured to the top of his head.

Sam frowned. “What’s wrong with my hair?”

“It’s long…too long,” (Y/N) narrowed his eyes suspiciously. He reached over and gently grabbed a piece of Sam’s hair before letting it go, allowing the strand to fall against Sam’s chubby cheek.

“Dad said he was going to get it cut soon.”

“Yeah, I know, but…it’s not like mine and Dean’s hair. It’s so much longer. It’s kind of like…” (Y/N) pursed his lips as he studied the top of his head. “Werewolf hair. Maybe you’re turning into a werewolf.”

Sam’s eyes slowly widened as he sat up straight and shifted uneasily in his seat. “I-I’m not turning into a werewolf.”

“I don’t know, it sure seems like it.”

Sam reached up and hesitantly ran his fingers through his hair. “How…how would I know if I’m turning into a werewolf?”

“What? You don’t know the signs?”

Sam shook his head. (Y/N) scoffed.

“Come on, Sammy! You have to know the classic signs!” (Y/N) exclaimed as he leaned forward, a small smirk playing on the corner of his lips. “The long hair, the way your fingernails curve, the hair between your eyebrows, and your sharp teeth.”

Sam brought his hands up to his face, his fingers roaming around his features. Quickly, he got off the couch and ran towards the motel bathroom, shoving the door open so hard that it bounced off the wall. (Y/N) followed after his brother. He watched as Sam studied himself in the mirror. He ran his fingers through his hair, brushed a single finger down his nose, studied the curvature of his fingernails, and bared his teeth. His eyes widened as soon as they landed on his sharp canines. Sam frowned and pushed his bottom lip out. It began to wobble as tears appeared in the corner of his eyes. He turned to (Y/N).

“I-I don’t want to be a werewolf!” He whimpered.

(Y/N) leaned against the doorframe and shrugged his shoulders. “Sorry, Sammy. It looks like you can’t help it.”

“B-But,” Sam turned and looked at himself in the mirror for a second before turning back to his brother. “But what if hunters come after me?”

“Hey!” (Y/N) shook his head as he walked closer to Sam. He placed both of his hands on his shoulders, bending down so that he was at eye level with his little brother. “That is something you never have to worry about. Dean, Dad, and I will protect you.”

Tears streaked down his red cheeks and he nodded. “Do you think Dad and De know?”

(Y/N) sighed and pursed his lips, moving his hands off of Sam so that he could place them on his hips. “I don’t know. I don’t think so. They haven’t said anything about it, yet. But, I think you should tell them. That way, they will be able to protect you.”

“I-I don’t wanna tell them.”

“Why not?”

“What if they don’t like me anymore because I’m a werewolf?”

(Y/N) shook his head and gave a comforting smile. “Sammy, they’re always going to love you, werewolf or not.”

“Really?”

“Really.”

Sam glanced down at the ground, his shoulders slumped. (Y/N) could see how much the news had upset his brother. He didn’t want him to be in hysterics by the time Dean got back, so he thought of the next best thing to try and cheer him up.

“You know, a lot of people think that werewolves are the bad guys,” he began. “But you could be the first-ever werewolf hunter! You could be the one werewolf that protects humans from bad things! Kind of like a…uh…a werewolf superhero!”

Sam looked up at him and raised his brows, cocking his head to the side. “A werewolf superhero?”

“Yeah!”

“Like a…a werewolf Batman?” A smile slowly appeared on Sam’s lips.

“Just like a werewolf Batman.”

The worry quickly left Sam’s face as he looked at himself in the mirror. He studied his face once more. “Maybe being a werewolf isn’t so bad,” he shrugged. “Thank you, (Y/N).”

“Anytime, Sammy,”

Sam turned and wrapped his arms tightly around (Y/N) in a bone-crushing embrace. “I love you.”

(Y/N) couldn’t help the smile that appeared on his face. Whether it was from the sentimental words or the devious nature behind them, he wasn’t sure. He wrapped his arms around Sam as well, pulling him close.

“I love you, too, Sammy.”

For six months, six whole months, Sam kept the little secret quiet. He would mention it to me from time to time. Ask me questions about lycanthropy in general or question me about whether or not I thought Dean and our Dad knew about it. I would always comfort him, tell him that I didn’t think they knew anything, and we would go about our day-to-day lives.

Eventually, it got to a point where I was hounding him to tell Dean and Dad about it. Sam was hesitant at first. He was scared about how they would react. I was able to talk him through it, though, and, one night, he sat all of us down so he could tell us.

The look on Dean and Dad’s faces?

Pure confusion.

And I thought it was the funniest thing at the time.

I had to hold back my laughter as I watched my father deal with Sam and explain that he couldn't be a werewolf if he had not been bitten by one. Sam was in hysterics at that point. He was crying and sobbing and while our father was trying his best to comfort him, I was trying my best to keep it together. At that moment, I patted myself on the back for the longest-lasting prank.

The celebration didn’t last long. When Sam told our father that I was the one who told him about it, he was furious. I swear, I saw his eyes turn red. I won’t go into too many details about my punishment, but it was one of the worst ones that I got. Even now, I don’t think that it was what I deserved. But it happened, and I can’t necessarily change it.

I couldn’t sit down for a week.

The punishment didn’t stop me from teasing Sam about it, but it was quick to make me stop when Sam told me he was going to tell Dad. Now that Dad’s dead, Sam doesn’t have anyone to tattle to. I can say whatever I want.

Cut that damn hair, Sammy. You look like a werewolf.

JANUARY 2010

We always had some type of celebration for our birthdays. When we got older, that is. Not all of them necessarily had a cake and presents, but they were celebrations nonetheless whether we acknowledged it or not. Whenever Dean has a birthday, his favorite place to go is at any local bar that we were closest to at the time. Sam and I would switch back and forth on who would be the designated driver so that the other one could celebrate properly with Dean. On Dean’s 31st birthday, I was the designated driver.

And, man, was I glad I was.

We were in Colorado after just finishing a hunt. It was a smaller bar near the far northeast corner of the state. It was a little busy, given it was a Sunday, but most of the clientele seemed to consist of regulars who would come in after their nine-to-five. I honestly couldn’t tell you what the theme of the bar was. The decoration scattered on the walls was a mix of historical pieces from the town we were in, rock 'n roll memorabilia, and different pieces from various Colorado sports teams.

Dean was plastered, and Sam wasn’t too far behind him. It had been a while since I saw the two of them get that drunk, but we were under a lot of stress at the time. I was jealous that I wasn’t the one who was able to get drunk enough to forget, but I figured I would make up for it later.

The bar began to shut down around one in the morning. The bartender had shouted for 'last call' half an hour before. I knew that I had to get Sam and Dean back to the motel before we got kicked out. It wasn’t that hard to find Sam, he had refused to leave his seat at the table the entire night. Trying to find Dean, on the other hand, reminded me of reading those ‘Where’s Waldo?’ books in the school library when I was younger.

Let me tell you when I did find him…

Oh boy.

(Y/N) sighed as he ran a hand down his face. His eyes drooped and he felt as if his body weighed a thousand pounds. After scouring the entire bar to find his brother for the past thirty minutes, he concluded that he deserved a bed for himself when they got back to the motel. Sam and Dean could share a bed, or sleep on the floor. He didn’t care. He just wanted to get back and go to sleep.

(Y/N) walked back up to the table that the three brothers had shared. Sam sat in his seat, back slouched over, his head laid on the wooden surface. His mop of hair was brushed carelessly over his face. (Y/N) placed a hand on his back, leaning close to him.

“Sammy,” he said, his voice low. Sam visibly jumped as he looked up at him with tired, glazed eyes. “Have you seen Dean?”

“Um…” Sam trailed, voice slurred, and pursed his lips. “Dean…Dean…” Before he could continue, Sam broke into a weak fit of laughter, his shoulders shaking. “Dean sounds a lot like ‘bean’. He looks like a bean because he’s short.”

(Y/N) pressed his lips together and patted Sam’s back. “He sure does, buddy. Thanks for the help.” He spoke sarcastically.

He stood up straight and turned around, his back now facing Sam. He ran his fingers through his hair as he looked around the almost empty bar. There were still a couple of regulars scattered around here and there, but most of them were clearing out. No sign of Dean, though. (Y/N) had to wonder how his brother could get lost in such a small place, but Dean had managed to do the impossible. Again.

In front of him, (Y/N) could see the bartender from earlier. She had walked around the small U-shaped bar and was making her way towards him. Before she could get closer, (Y/N) shook his head. He held his hands up slightly.

“I know you made 'last call' a while ago, and I’m sorry for staying, ma’am. I’m just trying to find my idiot brother.” He said with an apologetic tone.

“Well, that was actually why I was coming over here.” She said and placed her hands on her hips. “There’s some guy in the back and I was wondering if he belonged to you.”

(Y/N)’s shoulders slouched as he let out a sigh. “I am so sorry. I’ll pay for anything he broke or stole.”

“No, he didn’t break or steal anything. He’s doing…something else.”

(Y/N) furrowed his brows as an uneasy feeling began to make its way to his stomach. “What is he doing?”

She gestured back towards the bar. “Why don’t you come see for yourself?”

Hesitantly, he gave a nod and followed the bartender. She took him around the bar and to the back. Past the saloon-style swinging doors, a couple of feet into the supply room, (Y/N) came face to face with a sight he would never be able to forget.

Dean leaned against one of the many metal shelves. Even with something to lean on, his body swayed back and forth, indicating just how intoxicated he was. A goofy grin was present on his red face. One hand was balled into a fist and placed on his hip while the other one hung casually off of the shelf he leaned on. Beside him stood a mannequin, clad in an aged Colorado Rockies uniform paired with a baseball cap featuring the same team’s logo. (Y/N)’s jaw dropped.

Dean was flirting with a mannequin.

The bartender smirked. “He’s been back here for the last hour. I was going to kick him out, but I listened to how sweet he was being to Manny and I felt bad for him, so I just let him stay.” She nodded and leaned against the door, propping it open.

“Manny?” (Y/N) questioned, not taking his eyes off of his brother.

“Yeah. Manny the Mannequin. It’s this damn mannequin that the owner bought for twenty bucks when the local Sears closed down. He needed to put his stupid baseball outfit somewhere and he thought the best thing to do would be to put it on Manny and leave it in a bar. The regulars weren’t too nice to Manny, so we had to put him in the back here. It seems like your brother somehow snuck past me and found him.”

“I…I am so sorry about this.” (Y/N) gestured to his brother, who had begun to fiddle with the hem of the Rockies shirt.

The bartender snorted. “Trust me, this isn’t the worst thing a customer has done to poor Manny. Just get him out of here.”

“Yes, ma’am. Right away,” (Y/N) mumbled.

He stepped into the room just as the bartender turned and walked out. As he got closer, Dean began to giggle.

“You know, you have the prettiest eyes. Has anyone ever told you that? Oh, come on, I bet a lot of people tell you that. They’re like…like, um…” Dean paused and stared down at the ground.

(Y/N) quirked a brow and placed his hands on his hips. When he did, he felt the outline of his phone in his jeans pocket. A smirk made its way onto his face as he took out his phone. He knew that he could use this moment for entertainment purposes later. He began to record his brother as he cleared his throat. Dean jumped and turned to (Y/N), eyes wide.

“Hey, Dean. What’re you doing?” (Y/N) asked cautiously.

A smile broke out on Dean’s face as soon as he recognized his brother’s voice. “Oh! (Y/N), I want you to meet someone,” he slurred as he wrapped an arm around Manny’s shoulders, pulling the mannequin closer to him. “This is Cozy. She’s…she’s the most beautiful woman here and we’re going to get married.”

“Are you?”

“Yeah! Isn’t that right, baby?” Dean giggled as he reached up and poked Manny’s nose. “She’s the love of my life.”

“Well, I am so happy for you, Dean. She looks…beautiful.” (Y/N) was trying his hardest to keep from laughing.

“Thank you.” Dean smiled proudly.

“I think you’ve talked to Cozy enough for one day, though. I think we need to get back to the motel.”

Dean frowned. “But I don’t wanna. I wanna stay with Cozy.”

“I know, buddy,” (Y/N) walked over and placed his hand on Dean’s shoulder. “But Cozy has to go home, too. You can call her in the morning. Plus, we have pie back at the motel.”

Dean gasped dramatically. “Pie?”

“Yeah, pie,” (Y/N) pulled Dean away from the mannequin and wrapped an arm around his torso.

“Pecan?”

“Yes, Dean, pecan pie.”

“Oh, (Y/N), you know, you’re the best brother a guy could have.” Dean leaned his head against (Y/N)’s shoulder as the two of them stumbled out of the back room and towards their table. Dean let out another gasp as soon as he saw Sam. He patted Sam sloppily on his shoulder. “Sammy! Sammy! I met a girl!”

Sam groaned and lifted his head. He looked between (Y/N) and Dean, narrowing his eyes. “That’s not a girl! That’s your brother, stupid.” Sam grumbled.

(Y/N) sighed and rolled his eyes. “Come on, guys. Let’s get back to the motel before you pass out on me.”

There was no pie back at the motel. I just know that’s one of the only things that could get Dean’s attention.

Thankfully, both of them waited until they were in the car to pass out. I had tried my hardest to wake them up, but they weren’t budging. In the end, they both slept in the backseat of the Impala while lying on top of one another. It seemed like it would be extremely uncomfortable, but I wouldn’t know. I was able to go back into the room and relax in my own bed, in a place that was peaceful and quiet. No snoring, no moving around, nothing. It was some of the best sleep I ever had.

In the morning, when Dean and Sam woke up, they had to ruin my peaceful sleep by knocking on the door. They were a mess, both completely out of it and hungover. The smell of vomit stunk up the room so bad that I swear it’s still there if we were to go back and check. I got them painkillers, got them some water, and made sure they were nice and fed. When we were all sitting down and finally eating, I let them have it.

Oh, the teasing.

So much teasing.

I showed them both the video of Dean flirting with Manny. Dean grumbled and tried to get me to delete the video while Sam was trying his best not to laugh his ass off - he really couldn’t because of how bad his head probably hurt. Throughout our conversation, I swear, whenever I would look over at Dean, I could see his cheeks turn pink. I knew I had the perfect blackmail.

I still have the video.

You know, just in case.

APRIL 2014

Everyone who knows Dean understands just how much of a serial flirt he is. If it breathes and if he finds it attractive, he will flirt with it (the story with Manny should make that pretty obvious). I, on the contrary, know how to flirt, but I don’t do it as often as he does. Sure, I flirt with people now and then to get my fix, but it’s not something that I do every time I go out.

Sam, on the other hand, is the complete opposite of Dean.

Sam was always the type to be awkward around people he found attractive, even when he was a kid. The number of times I would see him in the hallways of schools trying to talk to girls was hilarious, but he carried that awkwardness into adulthood. I admit, a couple of years ago, that boy had some moves. He knew all the right things to say and do to make anyone swoon for him. I was sort of jealous of him, and I could tell that Dean was proud of him, in a way.

However, with how much has been going on the past couple of years, I’ve noticed that Sam has gotten a little rusty when it comes to flirting. There has been more than one occasion where he received a pretty nasty glare or a drink to the face followed by some rather colorful language. At first, I felt bad for him, but then it started getting funny. As he kept trying, the conversations he would have with people would last longer and longer than the last time. It still took him a while to leave with anyone, but baby steps. Baby steps.

There was one time earlier this year when I thought he was going to get a happy ending. It was going so well! I had to admit that I had been spying on him throughout his interaction, just out of sheer curiosity. We were celebrating after a hunt in Arizona. Nothing too big, just a basic salt and burn with a basic bar afterward. It was Saturday and the bar seemed like it was packed. We were lucky to find a table. Thankfully we did because my feet had ached that night from all the digging.

While I rested at the table, Dean went off to try and snag his own after-hunt reward while Sam walked over to the bar to chat up some cute brunette he had seen. The entire time, I entertained myself by watching him from a distance. Everything was going so well.

Unfortunately, for Sam, he let his awkwardness get the best of him.

“I swear, none of the good-lookin’ ones are single,” Dean grumbled as he took his seat back at the table, a defeated look on his face.

“Maybe you should lower your standards?” (Y/N) shrugged as he took a sip of beer, his eyes glued to his younger brother across the bar. “I mean, they have to lower their standards to sleep with you, don’t they? It’s about time you do the same.”

“Fuck you,” Dean scoffed a sipped his beer.

“Sorry, not interested.”

Dean rolled his eyes before he looked at (Y/N), noticing his gaze. He furrowed his brows. “The Hell are you looking at, anyway?”

Dean turned his head to look in the same direction as (Y/N), shifting his head to look over people as he attempted to see what had grabbed his brother’s attention. (Y/N) licked his lips and smirked.

“Looks like Sammy might get some tonight.” He said.

“No shit? Where?”

“At the far end of the bar. He’s talking to the babe in the blue dress.”

Once Dean stopped moving his head, he was able to see Sam and the woman standing at the corner of the bar. Both of them were facing one another. The woman leaned up against the bar while Sam had his hands placed awkwardly in his pockets. Both of them had smiles on their faces as they talked.

“Damn, she’s hot,” Dean mumbled.

“I know, right? He needs to take his hands out of his pockets, though. He looks like a fucking shy middle-schooler asking his crush out to the dance.”

“Eh,” Dean waved him off. “He always looks like that.”

“Yeah, I know, and have you seen him leave with anyone recently?”

“Point taken. So, what? You’ve just been watching this whole time?”

“I need to keep myself entertained somehow. Not in the mood for a one-night-stand, so I have to make my own fun.”

Dean gave a short nod before he continued to watch Sam. (Y/N) and Dean sat in silence as they watched Sam talk with the woman, mumbling back and forth to one another. As the two of them talked, Sam became visibly more comfortable. His movements became more animated and he pulled one of his hands out of his pockets. Both Dean and (Y/N) were practically sitting on the edge of their seats, their drinks completely forgotten about.

After ten agonizing minutes of watching, it was clear that Sam had become completely relaxed. They continued to talk as the lively bar moved around them. It was almost as if no one existed but the two of them. They were so engrossed in their conversation that Sam neglected to see the serving tray full of beer that was sitting down on the bar next to them. Finally, Sam took his other hand out of his pocket. He moved to lean on the bar, but his elbow never touched the polished bartop.

Instead, his elbow leaned against the edge of the serving tray, knocking it over. The tray and glasses clattered to the ground, sending glass particles across the floor. Beer splashed on himself and the woman he had been talking to, who had a look of horror across her face.

(Y/N)’s eyes widened as he quickly reached over and grabbed Dean’s arm. His jaw dropped and he immediately felt the laughter bubble up inside of his chest. He covered his mouth with his other hand and turned towards Dean. Dean snorted and turned his body so that he was facing (Y/N), his own eyes wide and hand covering his mouth as well. Both Dean and (Y/N) shook as they tried to contain the laughter.

They sat there, attempting to hide their amusement as Sam walked back over to the table, a defeated look on his face. He sat down, grabbed the beer that he had once forgotten about, and took a long swig. When he saw Dean and (Y/N) practically doubled over, he raised a brow.

“What’re you two laughing at?” He asked as a small smirk played on the corner of his lips.

(Y/N) turned away from Dean, pressing his lips together as he placed both of his hands on his beer. His gaze averted to the table, unable to look at Sam without laughing. He shook his head.

“Nothing…” he spoke in a broken, high-pitched voice. “Nothing, nothing. You wouldn’t get it.” He waved off and took a drink.

Sam looked towards Dean, who took a drink as well. “Yeah, you wouldn’t get it,” he paused. “Just like you didn’t get that chick’s number.”

(Y/N) snorted as he let out a laugh, his shoulders bouncing. Sam’s smirk vanished and was replaced with a deep frown. His cheeks turned a light shade of pink as he slammed his cup down on the table and stood.

“Real mature, you guys,” he grumbled, grabbing his jacket from the back of the chair.

“Oh, come on, Sammy!” Dean exclaimed. “You almost had her!”

Sam rolled his eyes as he put his arms into his jacket sleeves. “Hey, Sammy, look on the bright side!” (Y/N) began. “At least you were able to get her wet somehow.”

(Y/N) howled and slapped his hand on the table, Dean following suit. One of (Y/N)'s arms was curled against his stomach as he leaned forward. Sam glared at him.

“I’m going back to the motel.” He growled out before he turned sharply and walked away before Dean or (Y/N) could say anything.

By the time (Y/N) and Dean were done laughing, tears were rolling down their faces and their cheeks were bright red. Dean used his thumb and index finger to wipe away the tears while (Y/N) used the collar of his shirt. Once they were both settled, they leaned back in their seats. Dean shook his head.

“We really need to get that kid a hooker or something,” He finally said.

“I second that,” (Y/N) nodded and raised his glass.

Dean raised his glass as well before they both drank.

Sam didn’t talk to us for the rest of the night. He didn’t talk to us for the next couple of days until we got back to the bunker. Dean and I would try to get him to talk to us about something, anything, even the nerdy shit that he’s into, but he wouldn’t budge. On the drive back, he was wearing his headphones the entire time, so that whenever Dean or I would try to talk to him, he had some type of excuse as to why he didn’t talk to us.

Little asshole.

Wish I had headphones that I could just pop in to ignore the two of them.

Maybe I’ll pick some up?

Of course, I felt bad for the kid. He looked like he was having a good time, but you should have seen the look on the woman’s face when the beer spilled all over her. It was priceless! I had wished I held it together long enough to be able to see what had happened afterward, but if the look on her face had any correlation with her reaction, it probably wasn’t a good one.

Don’t feel too bad for the kid, though, he got laid a couple of months ago. He’s fine, basically back to normal.

Still, Dean and I like to bring it up occasionally. Sam has stopped getting so angry about it and has just resorted to rolling his eyes and ignoring us. One of these days, he’s going to get the balls to use one of our embarrassing pick-up attempts against us to shut us up.

God knows he probably has more instances of us than we do of him.

OCTOBER 2014

Jesus, my wrist hurts. Do people normally write this much in their journals? Certainly not at once, right? I have to be setting a new World Record. I wonder if there’s a world record for something like this? I’ll need to look it up later.

Trust me, though, I have yet to scratch the surface of the embarrassing memories I have of my two brothers. These are just my favorite ones. If they decide to read this, I hope the two of you enjoyed going down memory lane! Maybe you’ll learn not to look at other people’s shit?

Who am I kidding, of course you won’t.

I’ll need to hide this somewhere else. Maybe my closet? Maybe in one of my bags? I can’t even think of a place where they won’t eventually find it. Whatever, I’ll hide it in the back of my closet and see where that gets me.

The bunker door just opened. Sounds like Sam and Dean are back from the supply run. I’ll need to make this short and simple so I can help them put the groceries away before they start bitching at me.

Until next time,

Stay safe. (That STILL sounds bad. God, I’m terrible at ending these things.)

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supercap2319 · 2 months

Text

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*

#x male reader #male reader insert #male x male #supernatural #dean winchester #Dean Winchester x male reader #sam winchester #jensen ackles #jared padalecki

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sweetenerobert · 7 months

Text

𝐏𝐈𝐄𝐂𝐄𝐒 𝐎𝐅 𝐀 𝐏𝐔𝐙𝐙𝐋𝐄

DAY THREE OF HAUNTED HOEDOWN

dean winchester x vampire!male reader

genre: vampire au, explicit, minors dni

prompt: vampire au + "i can see how badly you want this, so i'm going to make sure you get it."

summary: trying to remember the last five hours of what happened after your transformation, you suddenly remember having sex with a stranger and you try to retrace your steps

warning: strong language, mention of blood, mention of dying. unprotected P in A, dirty talk, oral (m giving/m receiving), pet names, spanking, choking, creampies

word count: 2.3k

a/n: TWO POSTS IN ONE DAY?? yep! if this seems rushed my apologies.

The night sky cascaded down on you as you were shivering. The night was beautiful, but it was cold as each step you took made everything feel like you were walking closer to death.

Your blue work shirt is coated in your blood — near where your collarbone and shoulder blade rested. Your black and white canvas shoes have drops of blood on them. Tears running down your face had dried up. You hated this feeling — you felt the after-effects of coming back alive after getting your throat ripped out. This process was painstakingly slow. And you were scared — scared that you may never be the same again, scared that you might do something to hurt someone. You needed guidance from someone — anyone could help you forget about the stressful night you had.

You hear a car engine behind you, and you want to hide from the person driving behind you, but you are too weak to even jump into the bushes next to you, so you keep slowly walking. Your emotions wanted to come out; you wanted to cry a river right now. And you didn't understand everything currently, and it freaked you out how bad you wanted to cry.

The car’s engine was slowly creeping behind you, and you snapped your eyes shut, hoping that it would pass you; you didn’t want to be around anyone at this moment. You just wanted to walk — you had no idea where you were going, and you didn’t care as long you were away from everyone.

You slowly opened your eyes and saw the car driving past you, and you exhaled a breath you were holding. But then you felt the wind get knocked out of you as you saw the car approaching you in reverse. Feeling a mix of confusion, sadness, and rage all at once, you wanted to throw up, but you managed to keep yourself calm as the car slowly drove next to you and the passenger window was down.

“Are you okay?”

You glance to your left and see a dirty-blonde-haired man sitting in the driver's seat and glancing at you. You had to admit he was attractive, but you could be near. Your emotions were all over the place, and you didn't want some totally stranger being in the middle of that.

“Um—” You almost jump about how normal your voice sounds. It doesn't sound raspy or gruff, just your normal voice.

“I’m fine, thanks for asking,” You dismissed.

“Are you sure? I mean, I could take you back to my room and make sure you are safe— It’s no —”

“I’m okay, sir. Just a little out of it.” As persistent as this guy was, you didn't want him to be in the middle of this experience; you needed to be alone, not held up in some guy's room.

You suddenly hear his car screech as he stops and gets out, jogging towards you. He steps in front of you, and you halt your walking.

“Let me help — you need it. Whatever you are going through, you shouldn't go through it alone.”

You couldn't tell if the man’s tone was genuine or commanding, but you wanted to cry either way. You nodded your head. “Okay, I’ll go with you.”

The man guides you to his car and opens the passenger door for you. As you slip into the passenger seat, he closes the door. He was walking around the car and returning to his previous position — closing his door and looking at you. You reluctantly smile at him.

“Is that blood on your shirt?”

You glance at your shirt and look back at the man. “It’s mine?” You shrug.

You were in a motel bathroom shower, letting the water hit the top of your head as it dribbled down your body. The sadness you felt eventually disappeared as the drive here calmed you down. You found out what the name was — it was Dean. And that he was looking at his brother — younger brother, and has a love for rock music.

You weren't feeling the sadness, but you were feeling another feeling, and you couldn’t figure out what it was, and it was bugging you a bit.

The hot water weaved around your body almost like a dress made of water, and it was the heat you needed. You were sick and tired of being cold; you miss feeling warm. The soap leaving your body made a creek of bubbles and water. It almost looked majestic in your eyes, and you appreciated how it looked for a second that you were fine, but how you felt wasn't okay.

Turning the faucet off and letting the rest of the water go down the drain, your feet hitting the porcelain tile ceramic flooring as you walk towards the mirror — grabbing a towel and wrapping it around your waist. Bringing your hands towards the mirror, wiping the condensation, and seeing yourself in the mirror, hands on the porcelain sink.

You start to sniffle because of the steam messing with your nose, but you catch the scent of something you’ve never smelled before. You look around the bathroom as you try to find the source of the smell, and you can't seem to see it, but the smell intensifies as you look at the door. Whatever the smell was coming from behind the door.

You open the bathroom door, and the steam above you rises and travels along the ceiling. You see Dean looking at something in his duffle bag. You notice he’s not in the same jacket as before. He’s now wearing a flannel shirt. But with each step toward Dean, the smell becomes more intense and almost deafening in a sense.

Dean hears the floorboards creak behind him, turns around, and sees you in nothing but a towel. “Oh, hey. How was the shower?”

“It was good,” You nod.

“That’s good. I can see you're doing a lot better,” Dean nods.

“Do you smell that?”

“Smell what?”

“I don't know. But It’s almost intoxicating.”

“Huh, I wouldn't know what you're smelling. That’s how I am with pie though,” Dean chuckles.

You crack a smile and walk around Dean, and that's when the smell draws behind you. You turn your head as Dean walks towards the small table in the room.

“It’s you,” You mutter.

“What?” Dean questions.

“The smell — It’s you.”

“I stink?”

“Well, no, You smell intoxicating, and a sense a strong desire from you and — It’s lust.”

“What’s lust?” Dean asks, confused.

“What I’ve been feeling and this stupid smell and — are you horny, Dean?” You ask.

It was like a teenager who hit puberty. Dean looked defensive and scared at the same time. He didn’t know how to answer your question, so he looked at you.

You walked towards him, wanting to hear his answer, but you couldn't ask him again. You needed him to tell you. “Sorry If I overstepped my boundaries, Dean. But I would like to know.”

Dean scoffed, crossing his arms. “So what? I’ve been horny for the past couple of days. My hand isn’t helpin’ as much as I think it is.”

“You need help?”

“From who? I’ve been so busy. I can barely find the time for anyone.”

You unwrap your towel, and your cock sprung out hard as a rock, walking toward Dean, who can't seem to stop glancing at your cock. “From me, you could use me any way you want.” Days ago, you would’ve never had the confidence to tell anyone this, but this feeling sent you into overdrive, and you needed to get rid of it one way you could only think of.

Your hand finds Dean’s denim-covered cock already hard. As you rub your hand against the material, Dean inhales a breath and exhales a shaky breath. You unbutton Dean’s jeans and slide them down to his ankles. His cock leaps from the constriction his pants were torturing with. You were on your knees, and you took the tip of Dean’s cock in your mouth.

Dean slowly made his head go back as he enjoyed your warm mouth on his throbbing cock. He forgot how this felt; he hadn’t felt this relaxed in so long, and you provided him with a number one muscle relaxer.

His hips slowly start going back and forth into your mouth. You lightly gag on the tip as his thrusts hit the back of your throat. You notice Dean breathing through his plump lips; your cock throbs seeing him like this.

“Damn, baby. I’ve missed this so much,” Dean groaned.

You slip his cock out of your mouth, lick the slit of his dick, and he moans. You could taste the light pre-cum forming from it.

“Such a fuckin’ tease. I should fuck you just for that,” Dean seethed.

“I did say you could use me, so why not?” You shrug. You attempt to slide Dean’s cock inside your parted lips. He lifts you from your armpits and makes you stand up. Dean glances down at your cock and sees pre-cum leaking from your cock.

“I can see how badly you want this, so I'm going to make sure you get it." Dean kisses you passionately as his height makes you feel safe and protected, feelings you never thought you would feel again.

Your calves hit the back of the bed frame. You sit down on the edge of the bed — breaking the kiss. “Head on the pillows, now!” Dean commanded.

You comply with his command, and on your hands and knees, you crawl towards the pillow on Dean’s bed — Dean smacking your ass as you crawl to the pillow.

Dean takes his jeans off around his ankles, boots, and flannel. As he sees you lying on your back in the middle of his bed, his cock twitches, seeing the beautiful sight before him. He crawls after you and kisses you passionately, your cocks rubbing together, making this moment more intense than it already is.

Dean’s kisses trail down from your lips to your jaw and neck. Dean starts to nibble on your neck, and you whimper in retaliation — gripping the sheets, you feel your teeth getting outstretched — making you scared a little bit. Releasing your grip makes your teeth go back into their original shape.

Dean’s lips travel to your nipples as he sucks on them and pinches your nipples as he sucks the other one.

His kisses trail lower as his mouth makes contact with your hole. His tongue becomes an explorer, and he wants to explore you more. Your moans sound like music to Dean’s ear as he grips your thighs. “You taste like fuckin’ heaven, baby boy.”

You could cum hearing Dean call you a baby boy again.

Dean crawls up back to your face and adjusts his cock. You exclaim in pleasure as Dean slides his cock deep inside you. With each inch pushing deeper inside you, your moans became the sweet song Dean yearned for. You could feel your walls getting looser and looser; your hole was aching in pleasure.

“You’re so fuckin’ perfect, baby boy. Just what I needed,” Dean grunted. Dean was clenching his teeth. It was a sight that made your cock happy. Dean’s thrust became faster and more intoxicating with each passing moment.

“Fuck, Dean. You’re hitting so deep.” Your pre cum was rubbing against your naval. “Your pussy wraps around my cock so well, baby. I can't get enough of it,” Dean breathed. Dean leans his head closer to yours and kisses your lips more rough than gentle like last time.

Dean slides his cock out of you and flips you to lay on your stomach. You grip the pillows as he slides his cock in you — slowly.

“Such a fuckin’ tease,” You moaned.

“Only the best for my baby boy.”

Dean’s thrust becomes more intoxicating as you feel his balls clap against your ass. Dean makes a handprint on your ass — you yelp in response. You bring your head up, Dean wraps his arm around your neck, and you both share a passionate make-out between thrusts. You moan into each other’s mouths as you feel Dean’s cock twitch inside you.

“Baby, I’m going to overflow your ass with my cum,” Dean growls. Dean lets your neck go but pushes your head onto the pillow. You roll your head to the side to avoid suffocating. Your body starts to slide down, and you stop at an absolute point. The tip of your cock starts rubbing against the sheets, and you feel the lust almost shoot out of you.

“Dean, my cock — you're making my cock rub against the sheets,” You whimpered.

“Good, we get to cum together then, baby,” Dean growled.

You feel Dean’s cock get bigger inside you, and the throbbing intensifies. Dean’s thrust becomes more demon-like, and you're enjoying every thrust. You didn't want it to end this soon. Your teeth were feeling outstretched again, but you ignored it. You left your teeth stretched, and you bit down on the pillow.

“Fuck, baby boy. I’m cumming. I’m cummin’, baby boy!” You could feel his cum shoot inside you as you shoot strings of cum on the sheets under you. Dean clashes his hard chest on your back. “Thanks for that, baby boy.”

“Who said it has to end there? I told you that you could use me. I didn't specify for how long.” You turn your head to see a smirking Dean. “Well, then, you better get that pretty ass up. I’m going to fuck you against the wall.”

“That’s what happened hours ago?”

“Yeah?” Theo, your vampire “trainer” friend.

“Wow, does that happen to a lot of new vampires?” You ask.

Theo nods. “But, you should’ve seen me when I first turned.”

“Is that a story for another day?” You question.

“Hell yes.” Theo laughs.

“I would love to hear it then.” You smile.

#dean winchester #dean winchester x male reader #dean winchester x vampire!male reader #jensen ackles #jensen ackles x male reader #dean winchester supernatural #dean winchester smut #haunted hoedown

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dilfth1rster · 1 month

Note

I was wondering if you could do some smutty head cannons about Dean Winchester

Hi anon this is my first head canon like this, hope you enjoy it and if you want to further explore it, you know where to send me a request:)

Let's start with Dean is definitely a kinkyyyy himbo...

He's very dirty minded, any conversation that sparks as something a little sexual is like poking a bear with a stick. You never know what can trigger him.

I surely see him as both a dom and sub depending on a situation and or his mood. He doesn't see gender and would fuck anyone.

Nice chick in shorts a little too revealing? ... Yeah he would definitely try to hit that.

An older guy that gets a little too touchy after a couple of beers? Dean, umm- WOULD!

As of what he's into, it's a damn wide spectrum.

Starting with dress up... He loves that damn wild west cowboy shit. He loves getting in his cowboy boots and hat and a fringy jacket which also activates a dominant confident side in him.

He loves dominating and being dominated.

VERYYYY verbal whether it be about how nicely his big cock slides into you or how he degrades you and calls you his dirty cumwhore OR- how he pants in your ear while ramming into your ass with a speed of lightning.

He can NEVER decline a blowjob, he loves that shit. With him, it's more of a deepthroat or a "skullfuck" because he'd be holding you down on his wide 7 inches till u smelled the musky trimmed bush of his and later on definitely got lightheaded...

While I already mentioned his musk, I must add that his usual body smell is sweat mixed with a strong woodsy cologne and "leftover" whisky.

Dean appreciates when a lady shaves down there but he's a wild one for a hairy cunt as well as a bushy, hairy guy.

Loves high heels and "girly" accessories especially pink ones.

Is not scared nor intimidated by being called or referring to himself as Daddy.

Knows you're obsessed with his hands and loves helping you get wet by putting his chubby fingers in your mouth/throat.

DEAN WINCHESTER LOVES RISKY/OUTDOOR SEX!!!!!!! (includes public places such as dirty bar restroom which leads me to another thing that is...)

Unprotected sex. He's not friends with condoms, loves breeding you, and seeing his cum ooze out of you... and he CUMS A LOT.

He also loves getting bred by older guys(daddy issues I guess).

If you're okay with it:

He's definitely into watersports. Would love to piss on you, in his words "mark" you as his and degrade you.

Slap and choke you around(a little manhandling never hurt nobody huh?)

Make you worship his boots as a sign of your ultimate submission.

(let me include an image because it's getting hot in here...)

If it's longer than a one night stand he'd definitely want to cuckold you and make you watch as he breeds and destroys another young chick he met at the bar and brought to the motel room. Maybe if you're nice enough and behave he'll let you lick the juices off his cock after?

This man got a thing for piercings, belly button one that pops out from under your top, lip piercing or ESPECIALLY tongue and tits pierced... GOD DAMN!

Sex with him is usually fast paced(I say usually because from time to time it's not fast, IT'S DAMN RAPID)

SO... CUM-

we estabilished that mans got a breeding kink but well- Dean also loves cumming in your mouth and watching you swallow his sweet, chunky load, as well as painting your whole face in his seed.

If he's titty-fucking you he can explode directly on them.

If he's with a guy he enjoys getting bred and getting his face painted.

OH AND I ALMOST FORGOT-

This guy is a goddamn foodie, he loves to eat his sweet treats like the well known pie and such... he also loves to incorporate that into sex...

making you eat the pie he just came on or stuffing pieces of it into your pussy and eating you and IT out :)

Well- I think that's it for now. I'd love to further explore some of the aspect with you all, so if you got any questions or ideas, write away in the requests in my bio :)

(I'm a new writer so if you could like and reshare or leave a comment with your thoughts I'd really appreciate that)

#dean winchester #dean winchester smut #dean winchester fanfic #deanwinchester blurb #dean winchester headcanon #dean winchester x reader #supernatural smut #jensen ackles smut #jensen ackles headcanon #jensen ackles x reader #smut #male smut

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river13245 · 4 months

Text

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.

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