#flirty!dean

[supernaturalfreewill]

"Dean—"

He looked up to see you standing in the doorway, already in your pajamas which just happened to be one of his old t-shirts. Sam had gone to bed hours ago.

"Aren't you coming to bed?" you asked him, your forehead creased a little.

"I'm not tired," Dean sighed. "I'll be fine. I should keep working on this."

You stepped farther into the room. The floor was cold on your bare feet and the gentle padding sound of your steps echoed softly. "But if you don't," you said, stopping behind him and looping your arms around his neck, "I'll be so lonely without you. Come lay with me so I can feel whole again and fall asleep," you murmured. Your body leaned in against his and you nuzzled into the crook of his neck.

Dean sighed and his eyes closed, but he couldn't help smiling. His hand rested lightly on your forearm. "Are you trying to seduce me into healthy sleeping patterns?" he chuckled.

"Maybe," you hummed, kissing his neck. "Is it working?"

Dean laughed again. "Yes. Yes, it is."

"Oh, good," you breathed against his skin, and Dean could hear that you were smiling.

"Question..." Dean said softly. "You wearing anything else under that Metallica t-shirt?"

Now, it was your turn to laugh. "Why don't you come to bed and find out?"

"Oh, I'm definitely finding out," he said, pushing back from the table and turning just in time to see you scampering away toward the bedroom, biting your bottom lip.

#dean winchester #dean x reader #dean x you #dean drabbles #flirty!dean #dean imagines #spn drabbles #fanfiction #superrnatural #spn family

[wigglebox]

Suptober - Day 13 || Flirt [x]

#suptober23 #destiel #dean winchester #castiel #destiel fanart #spnfanart #wiggleart #this took me so long to figure out I literally had to scrap like ten ideas #despite always drawing them all cute together I actuall struggle with the concept of flirting I guess lmao #also I was gonna have dean being the one flirting at Cas but then I remembered how cute it was in the show when that #man was flirted at by people he was interested in lmao #looking at you Aaron #he got so flustered! #also I like confident flirty Cas sometimes okay lol #but I also like the headcanon or concept of Cas being unintentionally sexy or flirty and driving dean up the wall by merely idk folding laun #laundry lmao

[bloodfreak-boyking]

this is how that scene went right

#i have a theory that every time dean ribs sam #its to cover something that's like over the line flirty/sexual #like he's either gonna kiss sam or call him an idiot #emma rewatches spn #1x17 hell house #spn #wincest #samdean

[solarcas]

Suptober Day 13 - Flirt answer the question, Cas-

[Open for better quality!]

#go to bed dean you're drunk. ah wait #suptober23 #suptober #destiel #destiel fanart #deancas #deancas fanart #married deancas #dean winchester #bi!dean #castiel #castiel supernatural #flirty drunk dean #spn fanart #supernatural #traditional art #marker art #solar draws #chapeldean #emeraldcas #spxcekya #everybody give it up for beyonce tshirt cas ✨✨

[bloodydeanwinchester]

🩸Bloody Dean Every Episode🩸 ↳ 1x02 || Wendigo

#helloooooo s1 bloody dean you are SO gender #i love how that last gif shows that deans flirty bravado is actually all an act and as soon as someone actually kisses him he goes all soft #also WOW is it different going from coloring s15 to coloring s1 #bloodydeanseries #bloody dean #my beloved<3 #spn 1x02 #spnedit #deanedit #cowboycoven #spn #supernatural #dean winchester #s1 dean #tusersana #usermoogs #tw flashing

[soupernatural]

this fic has my favorite still-an-angel au cas and some of my favorite deanisms i’ve written. here! have some solo hunter dean flirting with ghost (1990) references and cas flirting by mind reading.

#i think about going back and editing some of my old fics and this is one of them but i just semi reread it and it’s cute still #this cas is sooooo autistic 2 me personally and this fic is my favorite flirty banter i’ve written too #it feels like dean 2 me but i wrote him so big shrugs #also dean loved ghost he’s just posturing #zo.txt #dc posting #zo.dbr #zo.au

[found--family]

#bisexual disaster #destiel #polls #flirty dean #thoughts #dean is bi #these were all unnecessary to The Plot and thus proved bi!dean + pining/flirty!dean and destiel in canon thankyou and goodnight

[fandomimaginesftw]

Hi! I love your writing and was hoping to request a Crowley x Female Reader fic please. The reader hangs around & hunts with the Winchesters, but unlike them she has a huge soft spot for Crowley and just loves his personality and kinda lets slip that she has feelings for him.

EEEE I've never written Crowley before! I really hope you like it <3

Word Count: 858

SPN Tags: @carryonmyswansong @mogaruke @hobby27

It was a boring day in the motel room. Sam and Dean had decided to go out to get some grub while Y/N sat in wait. The bed sat on wshe as uncomfortable, but she figured it would start to feel better once she got buzzed from the beer that was in the mini fridge. One after another, she drank and drank until the room started to fuzz and move a little. She lied back on the scratchy blanket, sighing softly as she lifted her arm to check the time her watch displayed, 2:23 pm. She groaned, pulling herself up to sit, then stumbled slightly as she stood.

“Squirrel and Moose off on another love fest?” A distinctive British voice asked, making Y/N’s head twist quickly. Her eyes fell upon the demon, former King of Hell, and she straightened up. She then shook her head, keeping gazes locked with him.

“No, they’re out getting food. What are you doing here Crowley?” She did her best to keep her composure, but there was something about the demon that struck a chord inside of her that was rarely strung. Maybe it was that devilish accent, no pun intended. Or maybe his eyes, or the way he carried himself. Whatever it was drove Y/N crazy when he was around. Of course, they would never let anyone know that, especially not the Winchesters. He hummed, sitting at the small dining table that was placed in the small room.

“I came with information, thought the boys might be interested.” He sent a smirk her way, making her cheeks freckle crimson.

“Oh? Care to share?” They sent a smirk back, not wanting him to know that he had any hold over her. He motioned her to come over with his fingers, sending Y/N’s mind into a swirl of conflicting emotions. They obliged, sitting in the other chair adjacent to his. He leaned in close, beckoning her closer with another wave of a finger. She leaned in closer, keeping her eyes trained on his, fighting every reflex she had to look at his pink lips. 

“The vampires you three ar elooking for? They’re closer than you think.” His eyes shot sown to her mouth, drinking in the sight. She stammered, binking a few too many times, then leaned back from him, her back resting against the chair. 

“How close?” Y/N asked, taking the liberty to look at the rest of his handsome face, not really caring if he saw now since he had just pulled what he did. He laced his fingers, tilting his head.

“I’ll tell you, for a price.” Y/N scoffed, crossing her arms. 

“No way, Crowley.” He then stood, taking two stesp to get in front of her. She swallowed lightly, looking up at him from her chair. He smirked down at her, lifting her chin with his first finger. He then bent over, their faces inches from each other.

“Too forward, darling? Next time, then.” He leaned over to her ear, whispering that the vampires’ nest headquarters is two doors down. Before she could say anything, he disappeared and then the door opened seconds later. She shot up from the chair, praying that her face wasn’t too red. Sam and Dean walked in with delicious smelling food, Dean sending her a wide smile.

“Grub time, Y/N. I got you a burger.” Dean handed her a bag, then noticed her face. His smile dropped and he sat the food down, tilting his cute little head a little. “What’s wrong?” Y/N shook her head, sending an equal msile his way.

“Nothing’s wrong! Why would anything be wrong?” She giggled unconvincingly, then sat down adn started eating her burger. Dean sat across from her ,raising a brow before shrugging and biting into his burger. Sam tossed around his salad with a fork, frowning in that way that he did when he was thinking. “By the way, the vamp’s nest is two doors down.” Y/N informed the brothers, then continued eating.

“How do you know that?”

“Well, Crowley told me.” Their cheeks started burning at the mention of his name, and Sam dropped his fork into his plastic salad bowl, snapping his head up to look at them. Dean did the same, setting his burger down.

“What are you doing?” Dean asked, pointing a shaming finger at her. Her eyes widened as she took another bite to avoid any eye contact.

“Y/N? Why did you make that face when you said his name?” Sam asked, coming to sit down as well. Y/N couldn’t really avoid them much longer, plus the alcohol in their system was working against her. 

“Oh my god, you like him?” Dean all but screamed. Y/N shrugged, eating faster than she ever had before. Sam groaned, and Y/N just whined, not wanting them to make un of her or give her a lecture.

“That’s…So weird, Y/N,” Sam said simply, then went back to his salad. Dean gave Y/N a questioning look before going back to his burger, not able to process this information at the moment.

#spn #supernatural #x reader #reader insert #crowley #crowley x reader #sam winchester #dean winchester #x you #x y/n #fluff #smut #flirting #crowley is flirty #asks #asks open #request #requests open #send in asks #send in requests

[supernaturalfreewill]

warnings: sexuality, (recommended NC17+) You didn't notice him standing in your doorway until his deep voice broke your concentration. You looked up over the top of your favorite book.

"Really?" Dean asked. "Again?"He leaned against the doorframe, an amused expression painting his handsome face.

You grinned and shrugged. "It's my favorite," you said. "It's a comfort story."

He stepped over the threshold. "Don't you get bored? I mean, how many times have you read it now?"

"I used to read it once a year," you said.

Dean laughed. "Nerd." His laugh always crinkled the corners of his eyes and made your heart jump in your chest. You found it irresistible. "Man, I hope I'm never stuck with you on a deserted island. You'd probably start reciting it from memory."

"If you and I were stuck on a deserted island, you think that is what I'd be doing?"

Dean's eyebrows lifted. "Wow. Didn't expect that from you but," he smiled and gave you a heated look, "that is so much better."

Your cheeks flushed. "What? No, Dean! I meant—I meant, like, trying to find a way off!"

Dean laughed harder. "Oh, I can think of a few ways to get you off."

"Dean! Oh my God!" You put a hand over your face and tried to hide your furious blushing.

"Hey, don't hide that! I love it when you blush," he said with a boyish smile. "I earned that."

"You're ridiculous," you said, managing to shoot him a look.

"True. But I'm hoping you like it," he said.

You sighed. "I hate to admit it but I do..."

Prompt: "I really hope I'm never stuck with you on a deserted island."

#flirty!dean #dean winchester x reader #dean winchester imagines #supernatural #spn imagines #dean winchester drabbles #dean winchester x you #dean w x y/n #spn reader insert #fanfiction

[pussypopstiel]

When pam told dean “you dont want me you just like to flirt” ive never been more deancoded in my life like sorry i do not want to fuck i just love to flirt

#but i hate the commitment of oh lets fuck NOOOO…. #my silly little posts #dean flirty but ultimately uninterested representation

[the-gray-ghosty]

Dean: "i killed hitler. You know what? I think that entitles me to free drinks for the rest of my life. I'm gonna get T shirts made."

Sam: "you know no one's going to believe you, right?"

Dean: "But you'll believe me. You were there."

#this scene #sam and dean #the way dean says ''but you'll believe me'' is so hot and like flirty lmaooo #sam winchester #spn #supernatural #dean winchester #samdean #i have a feeling he used that excuse a lot to try to get what he wanted ''cmon sammy i killed hitler-i deserve pie'' #''sammy i ahouldnt have to wash the impala since i just killed hitler'' #''sammy i killed hitler last week so i shoud get a pass from digging this grave''

[hunter-hero-nerd]

Bathroom Confessions

Prompt: “I would love to hear those words in any other place than this bathroom, holding your hair back.” Pairing: Dean Winchester x OC!Female Hunter (Olive O'Hara) Warnings: Nothing major, alcohol, sex mentioned, flirty fluff A/N: Hey y'all This is my first fic in a while, so please be kind! This is a one shot featuring my oc, Olive O'Hara. I have plans to make a series with her. So if you like this, be on the look out for that!

The Olive O'Hara Chronicles Masterlist! Main Masterlist!

The Impala buzzes with excitement as the three of us make our way to the bar Dean had spied up the road. I tug nervously at my dark wash denim skirt that is just a tad too short. It has been too long since I’ve gotten any, if you catch my drift, and I am out to play tonight. The hunt had gone way better than anyone, Sam especially, thought would go. So, when the older Winchester nearly demanded that we all go out for a celebratory drink, I said yes when I normally would say no. It’s painful to watch Dean flirt with any random girl and take her home. 

My crush on Dean, I always thought, had always been hidden until one night, a very drunk Sam proclaimed that it was very evident to him. So, after that I decided to stop putting myself in a situation for jealousy and giving my crush away to the Winchester that shouldn’t ever under any circumstances know. As cliche as it sounds, his friendship means way more to me than any stupid crush. 

But tonight, I am going to take a huge step in getting over someone… by getting under someone else. Some townie at the bar would have to do to give me the spark to give others a try. “And here we are! Some random bar! But, who gives a shit as long as they have booze!” Dean cheers from the driver’s seat as he puts the Impala in park in front of said random bar. 

We all climb out of the car and I catch Dean eyeing me up as I straighten out my skirt. “You dressed up tonight. Lookin’ good.” He winks seductively then offers his arm playfully. My stomach flutters but I take it as I know that’s how he is. He playfully flirts with most people. Really Sam is the only one who’s safe.

“Well, maybe y’all will be a man short going back to the motel tonight. If I’m lucky.” I say with some faux confidence in my voice.

“You really gonna go home with some rando?” Dean says, stopping us short. Is that jealousy I hear?

“C’mon, you do it. And plus, I’m not your average girl. Remember? I haven’t been a civilian since I was 18.”  I look up at his face and see it semi-relax, but he still doesn’t seem happy. He drops the conversation and leads us into the bar. His energy shifts and smirks down at me. 

“Who wants a drink!” He says and gets Sam and my drink orders and goes off to the bar. 

“Look, an open pool table. Wanna play?” Sam asks me with a smile. He knows I know he can beat me any day of the week, but he loves to torture me. And me being the friend I am, I oblige with a wave of my arm ushering him to lead the way. He racks us up as Dean came back with their beers and my vodka Red Bull.

“Here’s your girly drink.” He says with a smirk as he hands me the drink. I take it and chug at least half in one swig. “Better slow down! I ain’t holding back your hair if you get sick. You’ll have to get your rando to do that.” I roll my eyes and then place my drink on the high top table we had claimed. I pick up my cue and saunter over to the pool table.

“Ladies first.” Sam proclaims as he removes the rack from the table. I set my shot up and break the balls evenly throughout the table. I even sink one.

“Solids.” I call, proud I have a chance to out run Sam’s impeccable game.

“Finally getting good!” Dean cheers from the sidelines. I roll my eyes and line up my next shot. It just so happens to be in front of Dean and I have to lean over a bit. I flip my way too long hair out of my face. I need to cut it but every time I think about it I get upset. So, I like to let it grow as much as I can. “Liking this view, sweetheart.” I hear Dean say and I’m thrown off my game. I miss the shot terribly, and hear Sam’s roar of laughter.

“Guess it’s my go!” He cheers as he sets down his beer and surveys the table. I head back to the table and chug the rest of my drink.

“Want me to help you with your next shot?” Dean quips flirtatiously. I smirk before replying.

“Only if you buy me another drink.”

Many, many rounds later, I am drunker than I have ever been in my life. Dean and I have been playing this back and forth that has completely distracted me from my goal of getting over him. As I finish another drink, the room begins to spin. “Maybe let that be your last one, sweetheart.” Dean says as he catches me sliding off the edge of the bar stool.

“M-you’re probably right.” I say slurring my words. I grab his shirt to try to stabilize myself and look up at him as the world fades around me.

-Dean’s POV-

Olive has been killing me all night. The way she’s dressed, the way she’s carrying herself, the way she’s just existing. It makes it hard for me to not get sucked in and try to avoid all feelings for my fellow hunter. When I saw her down her first drink I knew she was in for a night. She never holds her liquor well and usually once she starts drinking, she turns into a fish. So, how could I let this woman that I cared for get shitfaced and go home with some rando to do god knows what? So, I glued myself to her hip. 

Olive starts slipping from her bar stool and I instinctively catch her and slide her back on. “Maybe let that one be the last one, sweetheart.” She mumbles something I can’t quite hear in return and grabs a hold of me. She looks up at me and I see her glassy brown eyes try their best to focus. “Oh, you’re trashed.” I joke as I feel a genuine smile appear on my face. She mumbles again. “What’s that?”

“Dean, I don’t feel good…” Her voice is small and almost embarrassed. 

“Okay! Bathroom!” I say without a second thought, scooping her into my arms and carrying her to the single bathroom. We’re barely in the room when she rushes to the toilet and pukes up all the vodka she’d been drinking. I follow her and sweep her long ebony hair out of the way. “It’s okay. It’s okay.” I shush as I rub circles into her back with my free hand. She starts to relax and come back to reality.

“I’m sorry…” She whispers as she sits back a little, wiping her mouth.

“Don’t start with the I’m sorrys. Once you start, you don’t stop, Drunk Oli.” She looks up at me with her beautiful eyes.

“I love you, Dean. Like. Love you love you.”

“I would love to hear those words in any other place than this bathroom, holding your hair back.” I say as I sweep a few stray hairs away from her face. She whines drunkenly.

“You don’t understaaaand.”

“It’s okay. You can tell me in the morning.” I laugh and help her to stand. “Let’s get you back to the motel.”

#dean winchester #fanfic #supernatural #dean x ofc #fluff #flirty fluff #writing prompt #oneshot #sam winchester

[applesandpomogranantes]

i need an edit to deja vu by olivia rodrigo except its Claire Novack and Dean into Jo Harvelle and Dean

#i will stand by this #Clare and Dean had the same relationship as Jo and Dean but Jo and Dean had flirty overtones that didnt fit with the rest of their #relationship #i mean #jo harvelle #was constantly feeling like #dean winchester #was treating her like a child because thats how #ellen harvelle #treated her (righfully so) #but i feel like so many parellels can be drawn between #Jo #and #claire novak #supernatural #Spn #spnedit #spn family

[snakecat]

rewatching free to be you and me after seeing that post that was like, misha collins was choosing to play castiel as an ancient being who doesn’t understand social cues so that’s why he gets in dean’s personal space etc. and they were also like, okay but that doesn’t explain jensen ackles’ choice to have dean hit on cas this entire episode. and i’m rewatching it now with this in mind and i’M like ???????

like yes, dean hits on people in a teasing/not serious way all the time. but his forwardness and sarcasm paired with castiel’s complete lack of knowledge of how humans interact with each other is WILD lmao like dean saying that line about how they’re thelma and louise and they’re gonna hold hands while they go off a cliff and cas is just visibly short circuiting cuz he has NO idea what dean is talking about or why they might be holding hands later. or how naturally dean fixes his tie while giving him advice about being a human. or when dean finds out cas might die and is immediately like “BERT AND ERNIE ARE GAY. AND YOU ARE NOT GONNA DIE A VIRGIN” like hello ???????? dean is just slowly destroying this angel and it’s the beginning of season 5. castiel i’m so sorry

#just wanna clarify that while the writers were obviously the ones to give dean all these flirty lines #jackles did NOT have to play it like that LMAO #the energy in this episode is so cursed cuz i can’t tell what the intentions of it are #like they HAD to know how gay this was. they had to #years ago i was like this this is obviously queerbaiting #and now i’m like. it prob was queerbaiting on their part but also with what we now know about the writers’ intentions and destiel #it has more layers than that. idk #i just feel like their chemistry is so goddamn obvious that it’s impossible to ignore #supernatural #free to be you and me #destiel #deancas #thoughts

[angelsdean]

knowing how much jensen hates the ending we got i just Knowww that man wanted the other one misha described aldjksjdk he wanted to sidle up to cas in that bar like “hey there” with his little texas drawl don’t argue with me im right

#idk why I’m imagining dean in cowboy getup but I am #ohhh camera angle we just see his bow legs walking up to the bar #and then dean says all flirty ‘hey there’ and the camera pans up to reveal cas #and he’s smiling his big gummy eye crinkling nose scronching smile #and dean smiles back and sits down waaay too close thighs and shoulders touching and they just keep grinning n drinking their little drinks #I would’ve been soooo happy with just that like I can read between the lines they’re in LOVE #vic.txt

[a-eo-iu]

also I've been thinking about Des my oc Des (short for Destiel) and about the song Os Anjos by Legião Urbana (a song about an angel being so so tired from all the evils of humanity) and about DTA Castiel (a fallen angel who is disillusioned with humanity) (and about how even in canon both Dean and Cas are very jaded and sarcastic guys), and I think I'm having some Thoughts about what to make of Des's personality

#youni originals #modern weirdos #des #basically all I have on him so far is he's an actual cowboy. like has his own little ranch. also very flirty #which is very dean #but thinking about an angel being so fucking tired of all the bullshit going on in the world and deciding to retire and #become a cowboy instead. and eventually learning of destiel and seeing sides (both good and bad) of himself in both of the characters #and being like fuck it that's who i am now. and naming himself destiel. #plus i loooove when angels are actually huge bitches #like yes this is a cosmic being who is good and righteous. and if you look at it wrong it WILL tell you to go fuck yourself. #also thinking about him being kinda neighbors with mill (reclusive lich who hates vampires) and having a flirty gay thing with her #like they're not together at all but they flirt and tease each other (or at least des does) to the point of people thinking they are #also des as an angel has so much knowledge (and possibly powers) that mill as a wizard would probably find useful #also the idea of an angel (holy being) and a lich (corrupted undead human) being friends. very fun