#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.

[rizlowwritessortof]

Take a Shot

Written for @artyandink 's Jensen-a-thon event!

Let's face it, his henley looks good on both of you...

Pairing: Dean x F. Reader

Word Count: 935

Warnings: Nothing but a little good old-fashioned sexual tension, no smut, but Dean being Dean is a warning in itself 🔥🔥🔥 (Dividers by the absolutely lovely Daisy @firefly-graphics )

The tile floor is cool on your bare feet as you walk down the hall, your mind focused on the banana pudding left in the fridge from earlier tonight. If you can’t fall asleep, you might as well eat, right?

It’s kind of nice in the bunker when everyone else is in bed, only the dim light from the night lights that are always on in all the common rooms, the quiet hum of some mysterious machinery in the background, whatever it is that keeps the power on in this place. You shiver a little, the air cool on your legs. Why bother with pants when nobody else is around, anyway?

You’re halfway through the library on your way to the kitchen when Dean’s voice makes you nearly jump out of your skin, your heart pounding hard as you whirl around to face him. He’s standing across the room, a crystal tumbler of amber liquid in hand, his eyes shadowed in the half-dark. “Is that my shirt?”

“Damn it, Dean, you scared the living shit out of me!” you scold, your hand on your chest, trying to keep your heart from pounding its way free. “Why are you up? I thought you went to bed a couple of hours ago!”

An amused smile curves his lips. “Backatcha, sweetheart.”

“Well – I – I couldn’t go to sleep. So I wanted a snack.”

“Yeah, well, same here, and I wanted a drink. Mystery solved.” It’s slowly dawning on you that you’re half-dressed, and you feel the blush move up your neck, your cheeks warming as he stares you down. “You never answered me. Is that my shirt?”

You’re wearing a cream-colored henley that you may or may not have stolen – borrowed – when you were doing laundry last weekend. It’s so soft, and so big (because it’s his) and comfy, and yes, if you were being honest, you like wearing it because it belongs to him. It’s been against his skin. And you would deny that even under threat of torture.

“Yes, okay, I borrowed your shirt. And just for your information, I wouldn’t have come out here like this if I knew you were lurking around.”

“I’m not lurking. And just for your information, I don’t mind you coming out here like that.” In fact, he’s thoroughly enjoying the way his shirt looks on you. It’s soft, and it’s clinging just right to show every detail of the curves beneath – not to mention your perky nipples. No, he doesn’t really mind at all.

You can see his eyes sparkle even in the poor lighting, and you hope he can’t see your blush from where he’s standing. “Well, stop staring.” You turn your back and flounce from the room, heading to the kitchen and hoping with everything in you that the henley is covering your ass. You brush your hand back there, relieved that it is – barely – and walk resolutely to the fridge. Seriously, what the hell is he doing up, anyway?

You take the container and toss the lid into the sink, grabbing a spoon from the nearby drawer, and lean against the counter, taking a spoonful of the creamy treat and closing your eyes as it hits your tongue. So good. Totally worth a little embarrassment.

“So, you gonna share, or what?” You jump, startled again glaring up at him as he approaches.

“For fuck’s sake, Dean, could you wear a bell or something?” A thoroughly devilish grin flashes for a second, but he manages to rein it in quickly. You scoop another spoonful of the pudding, but he takes your hand in his and steers it up towards his mouth. You watch as he takes it in, those sinful lips closing around it and his eyes blinking slowly as he savors it with a soft hum. You feel your legs wobble a little, and things are clenching that should not be clenching just from watching someone eat banana pudding.

“That’s good.” He lets go of your hand, and after a couple of seconds you actually remember to take it back. You force your eyes down, but now the view is his shoulders and chest underneath another henley from his collection, this one a midnight blue, and he’s wearing sweats and his feet are bare. And you are hopelessly screwed. “Thought you were hungry,” he teases as you stand there with the empty spoon in the air, trying to remember how to breathe.

“I am – I was,” you stammer.

“Then why aren’t you eating?” He laughs softly at your defiant frown.

“Because you’re distracting me.”

“You started it.” You stare up at him, your eyes wide.

“Since when do you get distracted by me? You barely even notice me.”

“Shows how much you know.” You still stare at him skeptically, and he gnaws a bit at that plush lower lip before he continues. “Every night I walk by your door and I picture in my head what you might be wearing to bed. Some nights… well, let’s just say I really wanna open that door.”

You set the container of pudding and the spoon on the counter beside you, never taking your eyes off him. “Then why haven’t you?”

He shrugs. “I don’t know. Maybe I’m afraid you’ll tell me to get lost.”

You’re starting to smile now. “You know what they say, you miss 100% of the shots you don’t take.”

Dean steps up close, his hand moving to stroke over your shoulder and down, curling his fingers around your arm as he leans in, his voice rumbling in your ear. “Oh, sweetheart – I don’t miss.”

Tags for my lovelies: 

 @saenalife    @deanscarlett    @jensensgotyoudean    @jinkieswouldyoulookatthis    @deansdirtylittlesecretsblog 

   @geeklibrarian    @leatherwhiskeycoffeeplaid      @mrswhozeewhatsis    @littlegreenplasticsoldier    @sleep-silent-angel  

  @darcia22    @winchesterprincessbride    @ellen-reincarnated1967    @eyes-of-a-disney-princess      @deanslittleangel2y5  

  @melanie451        @spectaculacular-sammy     @bookchic20    @jodyri    @selma-jean-blog   

        @savingapplepie-eatingthings    @kittenofdoomage    @masked-maiden42    @lean-mean-deanwinchester    @ericuhlorain  

  @undecided-garden    @ceeceewinchester    @typicalweirdbookworm          @callmesweetheartifyoumeanit    @youtoldalie 

   @tanithlowisabamf-blog    @deandoesthingstome    @jxackles    @nerdwholikesword    @soivebuiltupaworldofmagic  

  @kreweofimp  @gabavaldman    @chaos-and-the-calm67-blog    @darkx143    @disassociativedogma   

 @ioanashalala    @jencharlan    @deansthirstblog     @dorky-and-i-know-it    @mischief-maker1   

 @winchestersandwordprocessors    @percussiongirl2017    @bringmesomepie56   @akshi8278    @torn-and-frayed  

  @sandlee44   @wingedcatninja  @evansrogerskitten   @emoryhemsworth  @peaceinourtime82 

 @dean-winchester-is-a-warrior  @sarcasmqueen74   @maliburenee     @mrsjenniferwinchester   @yeehawbitchs  

 @emily-winchester  @hobby27    spnbaby-67   @zepskies

[heliotrope155]

I do think it'd been hilarious to have a truth-serumed or spelled Dean around Cas, just start spilling his guts and flirting worse. But also genuinely think Cas would get so overwhelmed from going zero to eighty on this that he'd duct tape Dean's mouth shut after attempts to tell him to stop confessing romantic feelings kept failing. Final resort, Cas would whoosh away to some glacier and sit there until he'd collected himself.

[bloodydeanwinchester]

san francisco convention || july 14th 2024

[castiels-undercoat]

Fic where Dean thinks Cas is genuinley fucking with him by doing his whole like, standing really close, being very serious, not understanding references thing and he truly cannot tell if Cas is hitting on him or making fun of him.

[targaryenchester]

~C: "Yes sweetie, raunchy flirtation aside, today's choice of dinner remains a mystery"

~D: "The answer's simple: something meaty ;)"

[wigglebox]

Suptober - Day 13 || Flirt [x]

[bloodfreak-boyking]

this is how that scene went right

[ghostlyfleur]

OKAY I HAD A THOUGHT: Deany-boy not knowing his S/O has a really amazing singing voice, until one day he walks in when they don’t know he’s there and hears them?? I just think it’d be really cute. ☺️☺️

requested by @faerieroyal at my old blog

oh. i like the way you think!

maybe you’re re-organizing the bookshelves, sam’s new and improved organization systems something you’ve long stopped trying to understand, and you think you’re alone at the library, re-shelving huge encyclopedias.

dean stops short at the entrance to the war room, mesmerized by your mindless singing so much so he briefly wonders if you’re actually a siren and didn’t disclose that information in the years you’ve lived with the boys. you’re singing “my jolly sailor bold” from pirates of the caribbean, so in his mind it’d make sense.

you choke on your own voice once you spot him listening.

“now, don’t stop on my account, sweetheart” you feel like you’re choking “think you’d make an extra deadly siren, i can barely breathe right now.”

dean then jokes about how he’d let you manipulate him all you want and you start giggling, his smile widening on his face, completely enamored with his girl.

[solarcas]

Suptober Day 13 - Flirt answer the question, Cas-

[Open for better quality!]

[supernaturalfreewill]

Warnings: flirty!dean is probably a warning <3, some innuendo Dean had been simply trying to cross the alley to get back to the lot down the street where he'd parked the Impala when he was suddenly hit from behind and flung toward the wall. His body tensed, ready to fight as his palms landed on the brick, an arm in the middle of his back pressing him forward into the obstacle. But the next moment—he stopped, frozen. All the tension went out of his body and he found himself smiling.

A voice came from over his shoulder, almost right into his ear. "I'm a little disappointed. I was expecting more of a struggle."

That voice was familiar and his smile turned into a low chuckle. "A struggle? We both know you're into that kind of thing... I can't give you what you want right away! Besides, you think I wouldn't recognize you?"

He could hear a smile in your voice now. "Recognize me? You didn't see me or hear me. How could you possibly recognize me, Dean?" Your arm finally left the center of his back and he turned to look at you, his green eyes drinking in the sight.

"Your perfume," he said, self-satisfied.

You nodded, licking your lips, drawing Dean's eyes down to them. "One problem with that," you said. He gave you a questioning look. "I'm not wearing any perfume."

Dean looked struck for a moment, his brow furrowing slightly but then he shrugged it off. "I guess it's just you then and let me just say—you smell amazing," he grinned.

"Flattery as usual, Mr. Winchester."

"Oh, of course," he said, slipping his hands into the pockets of his jacket. "Fuck, I'm glad to see you though. Even if you did just slam me into a wall..."

"You must be getting rusty," you commented.

"I promise I'm not. Come back to the hotel. I'll prove it to you," he said, bouncing on the balls of his feet, clearly proud of himself.

You couldn't help but laugh. "Nice one."

"Thanks. So you'll come then?"

"Why don't we just start with a beer first, hmm?"

"Yeah, sure. It's your call!" Prompt: "I'm a little disappointed. I was expecting more of a struggle."

[thefirstradiant]

Suptober Day 10: Mushroom 🍄

Hey y’all! For day 10 I considered lots of different alternatives and ended up going indulgent ✨ sciencey case fic! ✨ It’s a super fun little piece and it’s Outsider POV!! I vibe so hard with outsider pov, our boys are so ridiculous. This is my episode idea. Anyway, read the tags and author note, but enjoy!

Summary: How was Rachel supposed to know her day would end with her having aided and abetted the cute, yet criminal Infectious Disease researchers?

Word count: 3k. Rating: Teen.

[sampilled]

Had a really weird dream last night. It was a gossip girl/spn crossover and gossip girl was a spirit and that’s how she was so omnipotent and when sam and dean managed to kill her, all of the gg characters were pissed cuz they missed the attention

[bloodydeanwinchester]

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

[lovealwayssay]

Dean Winchester is Lorelai Gilmore coded.

[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.