#dean x male reader

[pascalsummers]

You Give Them a Magical Companion (Team Free Will x Male Reader)

A/N: So this idea of mine originally started as just stuffed animals given to them but I wanted to give it a more 'supernatural' vibe lol. I couldn't find an exact mythology for what I wanted to do so I took a bunch of inspiration and just made my own thing. I'll probably make another post later on fleshing this idea out because why not?

What you need to know for the sake of this post is that the reader can imbue an item (Usually Jewelry) with a magical creature influenced by the wearer. Anyway with that out of the way consider this my birthday gift to you all, and enjoy!

-

DEAN

When it came to Dean you decided that a bracelet would be the best option for him. Mostly because you remember Dean complaining about rings getting scratched up when opening beers and him getting hit in the teeth by necklaces. He will forever deny fanboying over the fact that his companion turned out to be a wolf but that doesn't stop him from subtly bragging about it once in a while. Dean's companion is mostly used during hunts to help track down monsters or sometimes help in battle if Dean really needs it. When not on a hunt Dean can be found hanging out in the Batcave with the wolf sitting close by.

SAM

For Sam, you decided that his item would be a ring. You didn't want to choose anything that stood out too much and a ring seemed like the perfect subtle piece of jewelry. Sam was a little worried that the world would decide to make his animal a moose but much to his relief, it turned out to be a simple owl. The owl became a kind of study buddy for Sam as he would ask his companion to find certain books for him while he focused on other tasks. In return, Sam would give the owl scratches which it would coo at, and eventually, he even made it a small nest in his room for it to rest on whenever it wanted.

CASTIEL

Figuring out what item to give Cas was a challenge since Cas didn't seem to have a big opinion on the matter. Eventually, though you decided that he would have a necklace. When Cas accepted the gift and saw that his companion was a cat he was confused but of course accepted it. Cas didn't know what to do with his new companion but after a bit of contemplation, he decided to get all the needed items for a cat owner and set them up in his room in the bunker. Though Cas's companion didn't require any food or water to live it did eat any food and drink any water that Cas gave it. Usually, the cat can be found perched on Cas's shoulder watching the people of the bunker.

CROWLEY

Thinking about how Crowley you knew that a brooch would be a good choice for him. You thought it was the perfect fit for someone whose closet seemed completely made of suits. When Crowley laid eyes on his tiger companion he thought that it was an apt creature to be paired with. Crowley is quick to befriend the companion and learn as much as he can about it. During meetings and interrogations, Crowley will sometimes let the tiger sit close to him as a way to add a little extra intimidation factor. When not busy with something Crowley will let his companion roam around especially when Crowley's with the Winchesters just to annoy them a little bit.

[mggsv]

Pink Panties

m!reader x dean winchester (18+)

summary: Dean does a try-on haul of panties he buys while out for a case

warnings: slight!sub dean, oral (m receiving)

“Perfect..now turn around”

“You like?”

“I love..���

You moan out softly, cock in your hand as you watched Dean’s nearly naked body from every angle he could give you. The only thing on him were the pink pair of lace panties he bought while out with Sam as a little gift for you. You watch the muscles flex in his perfect little ass as he turns around. You could hear him chuckle as a hand reached back to pull at the elastic material of the underwear. You feel a whimper creating from your throat, pre cum leaking from your tip.

“You look so good Dean.” You hum. He turns back around, and your eyes wonder to his almost bare cock, hard and waiting on you. You felt hungry watching it through the near transparent material. “Fuck..” You whisper- hand speeding up its movements. “Come here, please.” You ask softly.

“Is that what my boy wants?” you hear Dean ask. Your eyes shut tightly as your hips bucked into your hand, clock aching. “Yes..on your knees, please.” He smirks over at you, a small glint of mischief in his eyes. Getting down on his knees Dean groans softly. His hand crept over his soft nipples, thumb flicking over them while he stared at your desperate attempt to satisfy yourself. He stroked your cock faster, thinking of how much he’s fill you after this.. “Dean..”

You watch as he crawls to you, hand squeezing as your breath cut short. Soon, his face near your cock, tongue darting out to lick the slick covering your fingers. “Let it loose.” His voice sent waves throughout your body. You let go, letting the thick strings coat Deans lips. Your body shudders at his tongue wrapping around your swollen tip. “Please..” you groan. Your legs had a slight shake to them, you held back. “Please Dean- I need it.. I want it so badly.” your eyes welled up, thinking back to those now wet lace panties. “I know..trust i’m gonna give it to ya baby.”

[supercap2319]

"Is this... Dean?!" Y/N asked, holding onto the old polaroid picture of a young man who looked exactly like Dean.

Sam, who was looking something up on his laptop, looked up and when he zeroed in on the picture of his older brother. He was shocked. "It is Dean." He stood up and walked towards Y/N for a better look. The two of them crowded over the picture, and saw a young Dean leading a team of cheerleaders. It was so shocking. And so unlike Dean.

Dean didn't do anything that was 'girly'. So, to see him doing something in fact 'girly' was a shock to them both. They both looked at each other and laughed. "W-W-Where on earth did you find this picture?" Sam asked in between laughs.

Y/N wiped a tear away. "Remember that high school you guys told me to check out?"

"Yeah? What happened?"

"Ghost. Couldn't move on. And while I was checking the archives of the school, I happened to come across this picture. And I've got another one if you'd like to see it?" He showed Sam the other picture of Dean yelling into a megaphone.

Sam chuckled. "Oh my God. If Bobby could see this."

"What about Cas? I'm sure he'd love this more than the pizza man." Y/N laughed.

"You don't think we should show him, do you?"

"Oh, most definitely." Y/an grinned.

That's how they found themselves walking towards the garage as Dean was fixing Baby. "Hey, Kristen Dunst! I didn't know you were in Bring It On."

Dean turned away from the hood of the car and looked at them in annoyance. "What are you talking about, kid?"

"I'm talking about this!" Y/N showed him the pictures as Dean gasped in horror. "Son of a bitch!"

Y/N and Sam started to laugh.

[sam-winchesters-my-bf55]

Dean helping reader with his T shots:

A/n: I made a dean version too! Yippie!!

Starting off, Deans hyper supportive

Like, if someone even makes a 'weird sound' if your talking about it, he shuts it down immediately

He never wants you to feel bad about you becoming happy and comfy in your own skin. Never.

He does have a fear of needles, so he doesn't really look when you actually go to do the injection, and he prefers not to give you the injection himself, but he will if you really want him to.

Pokes fun at your facial hair when it starts coming in, especially the little mustache you get

You know he isn't actually trying to be mean

Like sam, he's always really proud of you

He thinks its fucking awesome that you're doing this

Goes with you to every appointment, every followup, anything.

He really wants you to know he cares

Definitely celebrates once you reach milestones

Talks to you in a deeper voice sometimes when your voice becomes noticeably deeper just to mess with you

Gives you tips on how to shave, and do other things

Never lets you get down about yourself, and he sure as hell never lets you get insecure.

(If you don't mind it) He happily shows off your progress

He thinks its the most coolest thing ever that your doing this, and wants everyone else to know just how cool you are too

[jxydiel]

Dean winchester x trans male!reader

I believe it can also be read as not romantic but Dean use a lot of sweet nicknames.

Note : I was really uncomfortable today and I needed some comfort so I wrote this. English is not my first language so sorry if there’s mistake

Tw: dysphoria, I don’t know if it’s a bit angst at the beginning since (y/n) is really uncomfortable with himself.

But technically it’s just fluff because I needed it x)

->

It was summer and the sun was blasting horribly armed with his warmth. (Y/N) could see by the window of ‘baby’, people sweating even in shorts and t-shirt and that was so mood wrenching. Everything was shining brightly hurting his eyes.

Dean was blasting some Metallica, humming and tapping the steering wheel rhythmically while Sam was side eyeing him. They were all out on the hunt heading to some ladies house for investigation. Strange things have been seen and it was their duty to take care of it.

Sam was the one who founded the case while reading some news paper. It was easy, not nerve wreaking. It was supposed to be a nice and calm day. If only that was really true.

When (Y/N) was preparing himself to go, he knew how hot it was today and putting just some pants and a t-shirt would seem to be a good idea but something was feeling so wrong. He was watching himself, in the mirror of that impersonal bathroom, from head to toe. He couldn’t help himself but to feel disgusted, maybe the pants were too tight or the shirt stopped too high showing his hips way too much or even his chest was showing off too much. The young man didn’t found his binder in his stuff and didn’t wanted to make the two Winchester wait so he just told himself that everything was fine even tho it was not. He tried to forget all the thoughts and doubts he had and left the bathroom. (Y/N) definitely hated summer and that was even an understatement.

That’s how he ended being so grumpy and uncomfortable in the back of that car, pulling his shirt away from his body. On normal days he would have been singing with Dean way too loudly, annoying Sam but today he was way too silent to the brothers liking. Something was off with the boy and they both knew it but no one asked for now.

The three of them arrived at the house and (Y/N) was already regretting getting out of his sit. He felt naked, like everyone was watching at him intensively. That was kind of suffocating. Everything was awful, everything was so wrong with him. His head was looking down at his body and he knew he made a big mistake. He just wanted to become invisible right now and just go back home.

The brothers were waiting for him in the most complete silence and he joined them when he realised, ashamed. Dean knocked on the door after looking at (Y/N) with unspoken worries. The woman opened the door and stared at the three mans heavily. (Y/N) didn’t wanted to be there, he wanted to escape and go back in the car where he felt more safe. The gaze of that woman was burning his skin.

Dean took care of explaining everything at her and she let them enter the place. Sam started the little questioning after she let them sit on the old sofa, the fabric of which seemed to escape, revealing the moss inside. Being sat made it a bit better for (Y/N) but he was still absent, not concentrate on anything that was being said. He couldn't stop thinking about his appearance, his thoughts tormenting him relentlessly. He was playing with his hands trying to be forgotten, be the ghost they were hunting. The older brother put an hand on his shoulder and whispered “Are you alright sweetheart?” The young man startled, not expecting any touch and only nodded in return not wanting to worry any of them but it was kind of late for that knowing the look on dean’s face.

The latter tried to focus on the business but seeing (Y/N) like this was making it hard. The two of them were so close that they technically never needed to speak to each other to know that something was off. He whispered again softly to the young man by his side “follow me” and left the couch heading outside. When something was wrong, he had to fix it as soon as possible, as he couldn't bear to see the other unhappy. “We’re coming back” he warned his lil’ brother and the client. (Y/N) didn’t wanted to stand up because he would become more visible, at the mercy of all judgment. but he did follow Dean outside the house. He would do anything for Dean and vice versa.

The older brother stood in the front yard with a concerned frown as (Y/N) got closer to him. He clearly noticed how the other was endlessly adjusting his shirt again and again avoiding his eyes and he just realised what was happening. Dean didn’t needed to ask anything, he just took off his jacket and put it on the other’s shoulders. “Here you go my handsome man” Strangely Dean was always wearing something on top of his shirt even in summer and he was thanking himself for this on the moment.

(Y/N) smiled at Dean, hiding himself in the big jacket. He whispered “thank you” and Dean answered an “Of course love”. (Y/N) put the jacket correctly and yes it was definitely better but even tho, now, he was just feeling like a fraud. The young man sighed and apologised for creating some kind of problems but Dean reacted so quickly “Eh you have nothing to be sorry for, it’s not your fault Okay ?” (Y/N) simply nodded in response. Dean put his hand on the head of the other caressing his hair with the utmost gentleness.

“Do you want me to drive you back to the motel ? We can let Sam take care of this.” Dean asked after a long silence. (Y/N) wanted to say yes so much but he didn’t wanted to bother the two mans. It was work right now, he needed to be professional. “No, I don’t want to bother. I’m alright now.” He simply responded. “You’re never bothering sweetheart you know that. Are you sure ?” “Yes don’t worry about it. Thank you tho.” And they both went inside the house again.

When they came back inside the woman asked them if they wanted to drink something and misgendered (Y/N). She didn’t knew. It wasn’t her fault. But (Y/N)’s heart broke in pieces and everything was so wrong again. Sam was the one who corrected her pretty quickly and she apologised. “It’s fine. You don’t need to apologise.” Replied the young man to relieve her. However, when (Y/N) looked up at Dean he saw his murderous gaze that was frightening the client horribly and it made him chuckle a bit. “Don’t stare like that. It’s fine” (Y/N) pushed Dean’s shoulder playfully trying to reassure him but his eyes were still sad and the other saw it.

“Well we’re leaving the questionary to our associate there’s other thing we need to take care of.” Dean announced pointing Sam. The lil’ bro nodded agreeing with no words to Dean’s decision. They both knew it was for the better. The big brother left the house with a quick goodbye and (Y/N) followed again. “But I said I was fine staying.” Dean stopped walking and looked at him. “I’m doing it for me, I would have killed her.” And it was half a lie.

(Y/N) smiled brightly at Dean and entered the car next to the taller one. When Sam wasn’t there the front sit was his. And sometimes even when Sammy was there they switched places.

Dean drove quite quickly to the motel and when he entered the bedroom he went directly to his stuff to found some clothes of his. He knew (Y/N) always liked wearing his clothes when he was feeling down. It gave him some more comfort. He threw the clothes at the boy who escaped in the bathroom. The young man was back a small time after and Dean was looking at him sitting on the bed. “Are you feeling better ?” The latter asked with a serious frown. “Yes thank you Dean. You’re the best.” (Y/N) replied sitting by his sides. “I know” They both smirked and laughed. Dean felt a little helpless when this happened because no one could control it, but he would give everything he had so that (Y/N) would never have to feel so bad again.

“You’re the most handsome man on this planet I hope you know that.” Dean stated genuinely going for a hug. (Y/N) hugged him back tightly, hiding himself in the bigs arms of the other. He was feeling safe now. Everything would be alright. They both lay down on the bed while the older brother turn the TV on for some ridiculous but funny show to change the other mind. “Sammy will call when he’s done. I will help him with the rest but you can stay here” (Y/N) nodded. “Okay. Be careful you two” “we always are no worries.” They both smiled at each other and (Y/N)‘s head rested on Dean’s chest hearing his heart beat fast as he breath in and out. “Next time something like that happens don’t wait that long. We will, Me and Sam, always do anything for you to be comfortable.” “Yes, thank you Dean.” They rested like that for a while Dean making sure (Y/N) was laughing and feeling better until it was time for him to go help his brother.

[certifiablyseth]

this was sooo fun ahhh I loved it smmm !!

Hello!! I saw that requests were open but if they aren’t feel free to ignore this!! I recently have been getting super into the SuperNatural fandom and was wondering if you could write some Dean X Reader (mlm) fluff/crack? Basically just them staying up super late and drinking energy drinks and doing random shit while watching tv and eating snacks? Please any thank you <33

Dean Winchester x Male reader

could be read as platonic or romantic

• When Dean decided to do a movie marathon with you, you knew it was going to be quite something.

• First, you picked the movies. When you couldn't choose you decided to call Charlie. She recommended Harry Potter since Dean hadn't watched them yet. (it made her very frustrated)

• Then you made a grocery list together. It looked like the list of a small child who had switched it with their mom's list hoping she wouldn't notice and would just buy everything the child wanted.

• A small summary: candy, lots of candy, popcorn, chocolate, chips, popcorn, and enough energy drinks to fight God (not that you were) oh, and don't forget the pie!

• While Dean was setting up a big white screen to project to the movie on Sam walked in. "Dean, what are you doing?" the taller brother questioned "Y/n and I are doing a movie marathon, wanna join?" Sam grimaced "Yeah, no. I'm just gonna read something and then go to bed."  You laughed "Come on Sammy, you'll miss out on all the fun" "Yeah" Dean added "some boring book can't be more interesting than this" "Actually it's a thesis about..." Dean cut Sam right off "Okay that's enough, just go." Sam went back to his room, you yelled after him "Good night!"

• You surprisingly got through the first two movies without any disruptions, if you don't count Dean talking over it, yelling when someone did something stupid or hyping up the characters when they did something smart...He decided that Hermoine is his favorite just like Charlie.

• After the first movie you also took the Pottermore test to see in which house Dean is in.

• At the third one it started to get harder to pay attention, that's when you started chugging the energy drinks, that in combination with a lot of candy got you through another one.

• After four movies you decided, high on sugar, to do some karaoke. Probably not the best idea since one, Dean sings horribly false and two, it was like 3am.

• The next morning (1pm for you) Sam greeted you with a sour face. "Next time you warn me if you're going to do a movie marathon again so I can leave the bunker as fast as I can."

• You definitely did it again. (Charlie decided to join too)

[l1tw1ck]

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

- 🛸

No Longer a Mentor

Sub!Bottom Dean Winchester x Top!Male Reader

☆ Word Count: 1,512 ☆

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

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

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

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

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

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

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

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

“Why?”

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

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

“I probably haven't what?”

“Had sex…lately……”

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

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

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

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

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

Dean nods.

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

He nods again, more enthusiastically this time.

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

“Fuck. You’re big.” He breathes out.

“Too big?”

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

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

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

“Is this your first time with a man?”

“Yeah…”

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

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

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

Dean’s face gets redder.

“Now, let me see how you suck cock.”

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

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

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

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

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

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

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

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

“I already fingered myself earlier.” He smiles.

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

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

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

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

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

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

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

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

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

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

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

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

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

[godjustkys]

| mdni 18+

| SUPERNATURAL headcanons

please give requests.

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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

[chaoticforever]

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

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

A/n: Not too sure about this one.

Damn these handcuffs, Y/n thought. 

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

And that someone is Dean Winchester.��

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

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

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

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

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

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

Like the way Dean looked at him.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

"Y/n."

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

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

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

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

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

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

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

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

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

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

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

He was finally free.

Dean couldn’t get to him now.

XXXXX XXXXX

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Y/n's heart pounded.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

XXXXX XXXXX 

[pascalsummers]

You Have Bad Luck (Team Free Will x Male Reader)

A/N: This idea entered my head and I wanted to get it out soon so hopefully this is close enough to the theme of Halloween lol. Enjoy!

-

DEAN

Dean is constantly bouncing between finding it funny and being worried about your well-being. Whenever you end up tripping or walking into a door he can't help but find it a little funny. However, if the fall looks particularly bad he will refrain from laughing at the moment and check up on you. Dean has basically forbidden you from going on hunts with them since he is not willing to risk your bad luck affecting you at the wrong time. If you do want to help them out Dean will let you do some research for them but that is about as far as he will go.

SAM

Sam tends to have more worry when it comes to you and your bad luck. He will tend to pay more attention to you when you are around him to make sure you don't get too hurt. Sam will also keep you away from being on the front lines of a hunt but is more willing to let you help with the research. He also finds your bad luck kind of interesting and will usually give you good luck charms that he finds to see how they affect your natural bad luck. Sam does his best to counteract your bad luck by catching you before you fall or giving you a sturdy phone case to prevent your phone from cracking.

CASTIEL

Cas is very confused by the bad luck that follows you around. At first, Cas wouldn't exactly know how often it affects you but as time goes on he would start to get a feeling for how it operates and would act accordingly. Whenever you end up injured he will heal you with his grace and make sure that you are okay. Cas is more willing to take you along with him on hunts since he knows he can heal you if you end up injured. However, there will still be times when Cas thinks it would be best for you to hang back and help with the research.

CROWLEY

Crowley found your bad luck to be very interesting. When he first learned about it he joked about your ancestor pissing a witch off as a reason for it. Crowley has no qualms about making a quip or two whenever you trip on a rock or when you forget your wallet at home. He will make sure that you are not too hurt though he will never do so in an obvious way. Crowley tends to no bring you with him to meetings and stuff with one of the reasons being that your bad luck could cause unnecessary distractions to him and his work. His favorite nickname for you is "Black Cat" for obvious reasons.

[suiternatural]

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

[supercap2319]

"You know if I die, I know exactly who to blame for my introduction into an early grave." Y/N said snarky. The sounds of grunts and fireballs hitting the walls behind them echoed inside this warehouse. Y/N sat down behind the safe of an old car as he glanced to his left and saw Sam and Dean Winchester pinned down as well.

He saw Dean rise and unload his gun on some swarm demons, but he quickly ducked to avoid being hit. "Oh, so this my fault, kid?" Dean's deep and gravelly voice said.

"Yes, because you didn't care about what I wanted or said. You only cared about what you wanted. I told you, you can't vanquish the swarm demons without vanquish the swarm king."

Dean opened his mouth to retort, but Sam interrupted. "Can you guys fight later? We gotta get out of here."

"Sammy's right. They're getting closer now."

"I have an idea. We blast and bail. Deal?"

The brothers nodded as they all stood up as Dean and Sam let their barrels loose of their bullets and Y/N used his telekinesis to send fireballs back at the demons before they ducked and ran for the Impala.

[spermeboy]

DIRTY DEAN!

pairings: dean winchester x male reader

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

requested by: anonymous

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

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

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

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

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

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

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

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

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

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

[mggsv]

Diner Boy

m!reader x dean winchester (18+)

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

warnings: car sex, hair pulling, overstimulation

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

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

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

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

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

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

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

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

“…yes.”

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

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

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

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

[twdxtrevor]

I swear, he does this to us on purpose . . .

[m4nspr34d]

BUT DADDY I LOVE HIM

Dean Winchester x M!reader

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

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

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

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

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

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

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

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

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

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

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

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

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

Thump.

Thump.

Thump..

Thump..

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