#30 days of dean winchester
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tgtbata · 4 months ago
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i will remember you all winter long
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chteretree · 5 months ago
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30 Queer Characters for Each Day of Pride Month.
I hope the eyes make you as uncomfortable as they made me 😘
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Day 23: Dean and Castiel from Supernatural!
This is another ask and you shall receive, the person who asked for this I’m sorry and you know who you are. Anyways yeah queerbaiting rules, this one’s for you tumblr
Full Speedpaint on YouTube!
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beckawinchester · 1 month ago
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Day 9
In another style
The only other style I can think of is cowboy 😂
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weewoowings · 1 month ago
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Shamelessly stolen from Twitter. Let's see if I remember to do it for the whole month.
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There is only one answer for me, and it has nothing to do with loving the other character any less.
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It's him. It's always been him. Loml 🫶🏼
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cupidswurld · 22 days ago
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sam dean costumes 💪 for dress up as ur type day
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m1zumono · 1 year ago
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trying to analyse sources this is boring it’s painful it hurts i wanna cry
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alltheficsiwant · 6 months ago
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I am completely hooked into this! This is so beautifully written. I love ittt!
A Deeper Kind of Kiss
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Summary: Y/N is ready to explore a new first with Dean, but will her harsh upbringing get in the way?
Warnings/Explicit 18+: Smut. Kissing, making out, mutual masturbation, a gentle kind of dirty talk, talk of sexual firsts, brief discussions of sex shaming, and a psychologically abusive parent, religion used as body control. All quite brief. Mostly this is fluffy smut! 😊❤️
Pairings: Dean Winchester x Y/N
Word Count: 3k+
A/N: So, I’ve decided to do all 30 of these writing prompts. I may miss a day here and there, but I’m going to try to do one a day, and I will be completing all 30 no matter what.  They won’t always be in order.  This fic will be for the prompt: Use the title of the last song you listened to.
That last song was "Kiss Me" by Ed Sheeran.
Hope you enjoy! I will be putting together a Masterlist for all 30 prompts and adding it to my main Masterlist.
A/N 2: K, this is a sequel to my very first prompt story:
First Time for Everything
and it's prequel:
An Introduction to Heroes and Monsters
I got quite a bit of feedback from the original story asking for more with them, to find out how they met, and then some fics showing more of Y/N's "firsts" with Dean. So, I'm planning on doing that.
This sequel picks up right where An Introduction to Heroes and Monsters left off. I've included the last few lines of that fic at the start of this one, just so it flows. You technically don't need to have read the other two to read this one, but it might make it more enjoyable. Hope you like it!
Both beautiful text dividers, below and at the bottom, were created by @talesmaniac89.
Masterlist // Tag Lists
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Y/N continued to look up at Dean's profile as she sat beside him on the couch and finally, he looked down at her with a questioning smile.
"Hey, kid. You good?"
Y/N smiled widely, amazed by her answer.
"So good." She said and pulled him close, kissing him softly and melting as he deepened it, tongue sweeping across her lips. She moaned softly and opened for him immediately.
He pulled her into his lap so he had better access to her lips and then her throat and then the delicate skin just below her collarbone where he sucked bruises into her skin.
He pushed his hand up under her shirt and grasped her breast.
Y/N gasped in surprise; it was the first time he'd touched her like that.
He pulled back, and his jaw was clenched tightly as she ran her fingernails through his stubble, loving the raspy sound it made.
"Sorry," he said hoarsely, "got a bit carried away."
He kissed the tip of her nose and leaned his forehead against hers.
She was breathing rough as she kissed him again, fast and hard before pulling away and asking him to continue. "Think you could get carried away again?"
His eyes were dark with lust and they made her shiver. "Are you sure?"
"Completely." She said and then leaned up to whisper in his ear. "I'm more than ready to share another first with you, Dean Winchester."
She pulled back slightly and Dean's dark, forest green eyes stared into her and through her as she held her breath.
"Come here." He whispered gently as he leaned close and turned his head so that his lips skated along her cheek. He skimmed his finger tips along her other cheek, tucking her hair behind her ear and then cupping the side of her face.
Leaning forward, he nuzzled his nose against the sensitive skin behind her ear, licking at it and nipping. Y/N let out a shuddered sigh and grabbed onto the sides of his open plaid shirt.
He took both sides of her face in his hands now, delicately, like she was made of something very fragile. He kissed her deeply, tongue dipping further and further into her mouth with each pass of his lips. She moaned and gripped his shirt tighter.
He sucked her bottom lip into his mouth as he pulled away, letting it go with a little pop.
"Do you like when I kiss you like that, Y/N, reaching into you, deeper and deeper?" Dean asked unnecessarily. He just wanted to hear her say it, wanted to listen to her confessions, wanted to hear her say yes again and again.
"Yes." She said quietly, still shy to talk about the passions he brought out in her. She wanted him so badly, and she knew he wanted her too. She knew he cared about her and would never hurt her.
But after years of being told her body was sinful, it was still hard for her to admit to the things she was feeling, and the things she liked.
He stood up from the couch and, grasping her hand, pulled her along down the bunker hallway and into his bedroom. He closed the door behind them and walked her backwards to his bed, kissing her ceaselessly as they moved.
He pushed her gently to sit on the bed and then to recline there against his pillows. He sat down beside her and for several minutes he just looked at her while he let his fingers glide across her cheekbones, over her forehead down the side of her neck, let his fingertips trace the contour of her lips.
"You're so unbelievably beautiful, sweetheart." Dean whispered to her, his deep, gruff, voice causing her stomach to flip flop pleasantly.
He leaned over her and kissed her softly as though he was trying to wake her from a hundred year slumber.
Dragging his lips down her neck, he spoke against her skin.
"I wanna see every inch of you, wanna put my hands on you, wanna taste the salt in your skin. I wanna feel you shake when I touch you, wanna make you come apart and watch the bliss spread across your beautiful face."
Y/N was already shaking in anticipation of feeling his hands on her bare skin, all of her bare skin.
"Do you want that, Y/N?"
She nodded emphatically.
"Say it, say you want me."
"Yes, Dean, I want you. God, please!" Y/N cried out as Dean pressed his lips to her pulse point.
He sat up again and his hands moved to the hem of her t-shirt. "Lift your arms up." He guided her and she raised them above her head.
He slowly lifted the t-shirt, dragging his hands over her ribs as he did so. When he'd pulled it off completely, he took another minute to just stare at her in the satiny, pale pink bra she wore.
His hot stare made her nipples harden and press against the cups of her bra. He brought his hand up and lazily rubbed his thumb in circles over the satin, making the hard little nub ache.
Her hands were still raised, lying on either side of her head, resting against the pillow. She closed her eyes tight and bit into her lower lip trying not to moan out her need for him. The way her blood rushed through her body, the way her core muscles were fluttering and clenching embarrassed her.
She couldn't help but feel like she was being too eager, or acting like a harlot, as her mother would say. She'd also say that men didn't really like women like that.
Dean sensed how she was holding back and stopped. "Open your eyes, sweetheart."
She did as he said and he could see her need reflected there, but he asked the question anyway. "Do you want me to stop? We can just lay here together; as long as I've got you in my arms, I'm happy."
But she was shaking her head. "No, Dean...I don't want you to stop. Please, don't stop."
Dean smiled gently. "Then what is it? You're holding back, I can tell. Are you scared? Because I promise I'm not going to do anything without asking you first."
Y/N bit her lip again and then spoke quietly. "I'm a little scared, but not of you. I'm scared I'm going to do something wrong, or stupid. Or that I'm gonna do or say something that turns you off...or...I don't know, it's all a little overwhelming. I've never felt like this before."
"Like what?"
Y/N blushed deeply, but Dean urged her on. "Tell me, sweetheart, tell me how you feel when I touch you."
She turned her head away from him, too shy to look at him when she answered.
"I feel like there's something hot against my skin, like it's branding me, but instead of wanting to pull away, it makes me want to be branded over every inch of my skin. When you're touching me in one place, I desperately want you to be touching me in all the places."
Dean placed two fingers on Y/N's chin and turned her face to him. "See, what you just said, was hot as hell. As long as all your reactions are honest, Y/N, you can't say or do anything wrong. And you're never going to turn me off by telling me what you like, whether it's with words or moans, or that breathy little sound you make when I do something like this."
Dean palmed her breast and grinned as she threw her head back and sucked in a stuttering gasp.
"Yeah, that's the one. All of those things turn me on. Big time. So tell me what you like, and tell me if you don't like something too. Tell me if I'm going too fast, or if you want me to stop."
He leaned down and kissed her slowly and thoroughly, sucking away all her breath and leaving her gasping.
He pulled back an inch and spoke against her lips. "Your pleasure turns into my pleasure, sweetheart. So, when I touch you here..."
He ran his hand up the outside of her bare thigh, his fingertips reaching just under the leg of her pajama shorts. With a slight curl of his strong fingers, he squeezed her thigh and Y/N let out a high moan.
"...and you make that noise, I know you like it and that definitely, fucking turns me on."
He moved his hands up to cup both her breasts, kneading gently, and Y/N covered them with her own, encouraging him, with her head thrown back against the pillow.
Dean leaned down and trailed featherlight kisses across the swell of her breasts. He ran his callused fingers up and down her ribcage before placing a final kiss at the top of each breast and then sitting up.
He ran the tip of his forefinger along the line of her bra.
"Will you take this off for me and let me see you, touch you, taste you?'
Y/N nodded and sat up too. She reached behind her and unhooked the material there. It hung loose on her shoulders for a moment, still covering her breasts and she thought Dean might try to remove it for her. But he stayed still, waiting for her to reveal herself to him in her own time.
She reached up and pulled on the straps, peeling the satin from her skin. Dean's eyes became almost black, his pupils crowding out the verdant green as he took in her half-naked form.
Goosebumps pebbled her skin as she watched his eyes scan over her. She was desperate to feel him caress her flesh, to feel him brand her with his fingerprints.
She looked at his mouth as he bit into his bottom lip, and a quiet whine escaped her.
"Please, Dean," she entreated, "I need you to...I need your mouth..."
She stumbled over what she was asking, but Dean understood anyway and he leaned in for a soft, brief kiss.
"Lay back " He directed her, his voice low and silky.
She laid back against the pillows, and sidled in closer to Dean as he stretched out alongside her.
"Tell me what you like, Y/N." Dean reminded her as he trailed his fingers down from her collarbone and then down over her left breast. He encircled her nipple with his blunt fingertip, before taking it between his thumb and forefinger and giving a small tug.
Y/N gasped harshly and then a deep moan issued from her throat in a voice she barely recognized as her own.
"Do you like that, sweetheart? And this?" He asked as he lowered his head to her breast and sealed his lips around her nipple, swirling his tongue around the tight bud.
Y/N plunged her hands into Dean's short locks and gripped tightly. He drew her nipple and the flesh all around it deep into his mouth and sucked hard, making Y/N yank on the hair she had entwined in her fingers.
Dean growled and Y/N dropped her hands. "Oh, Dean, I'm so sorry." She panted.
But Dean merely bit her skin gently before letting her breast fall out of his mouth.
"Don't be,"he said, and his breathing was rough too, "I like it."
His grin was all wickedness before he lowered his head to her right breast and gave it the same attention.
Y/N was soon writhing mindlessly on the bed, her hands alternating between pulling on Dean's hair as he made pleasure spike through her veins, and knotting up the bedsheets beneath her as she tried not to shout out her need.
Dean pulled his head up so his mouth was level with hers once again and kissed her long, licking into her open mouth and sucking on her tongue while his big hand alternated back and forth, squeezing and kneading first one breast and then the next.
Pulling away from her mouth and leaving her breathless, Dean moved his hand down to rest against the waistband of her shorts.
"How are you doing, sweetheart?" He asked. Y/N licked her lips and tried to speak.
"I'm...good..." She took a shuddering breath. "So good. Please don't stop."
Dean shook his head. "I won't. Are you ready to go further?" His long fingers splayed across her lower abdomen, the tips resting just above the softly rising mound beneath her thin shorts.
Y/N felt the breath whoosh out of her lungs and nervousness set in. Sensing it, Dean pulled his hand back up, covering her bellybutton.
"It's okay, sweetheart, we don't have to."
But Y/N was shaking her head. "No, I want to. I..."
She threw one hand over her eyes. "I...God Dean, I want you to touch me so badly, but..."
She trailed off, and Dean pulled her tighter against his side.
"Tell me, sweetheart. Remember, can't say anything wrong as long as it's how you really feel."
Y/N took a moment before she looked up at him and told the truth. "I've never...never been touched there."
Dean smiled gently. "Well, no, I figured."
Y/N shook her head. "No, I mean...never. Not, not even by me."
Dean's eyes widened and she felt her cheeks go red. Dean quickly schooled his features, but Y/N knew she'd shocked him. She tried to explain.
"For as long as I can remember, I was told that that..." She struggled to find words. "...area was sinful, wicked, and touching myself in any context other than to wash, meant I was depraved and perverted."
Dean was scowling deeply and Y/N was quick to reassure him. "I certainly don't believe that anymore. But it's been hard to change that deeply ingrained feeling that it's wrong. When I was..."
She cut herself off abruptly and looked away from him.
Dean kissed the cheek he could reach, brushing his knuckles gently over her cheekbone.
"You're safe, Y/N. Nothing we do here together can be wrong if we both want it and everything we say and do here is just for us and will never leave this space between us. So, what were you going to say?"
Y/N nodded, knowing she was safe, and knowing too, that the way Dean touched her was something sacred, not wicked. But she blushed over what she was saying anyway. She couldn't help it.
"When I was...pining over you, wanting you to kiss me and touch me, and sure you'd never see me like that..."
She paused and Dean took the opportunity to kiss her quick and hard. "Silly girl." He admonished.
Y/N ended the kiss smiling. "Yeah, well...anyway...I thought about you all the time. And at night I couldn't stop my mind from wandering, thinking about your beautiful face and your hands and, God your mouth!"
Y/N brought her hand up to trace his plump lips. "I couldn't help it, and the more I thought about you the more I...um...ached - down there. It got so bad, and I wanted you to touch me so much that I finally decided to...touch myself."
Y/N shrugged her face burning. "I'd long ago realized my mother's thinking was antiquated and backwards. I knew it wasn't really a big deal and that apparently people did it all the time."
She grinned shakily at Dean. "I'd watched a lot of television by that point and they certainly treated it as something comical that everyone does."
She bit her bottom lip. "But then, before I was able to work up the nerve, I started wondering whether it was disrespectful, and maybe even gross and wrong to be...thinking about you while I was touching myself so...privately. It felt wrong to do something like that to you in my head. So, I stopped myself and went to bed miserable as usual."
Y/N looked into Dean's face and saw his deep desire there, making her think she'd been mistaken, maybe it wasn't wrong. Maybe he didn't mind.
Dean took a breath in through his nostrils. "So does that mean that you've never had an orgasm?"
Y/N ducked her head. "Actually, I think I had one while I was sleeping once. I woke up just as it was ending and it was such a strange feeling. But I remembered that I'd been dreaming about you, and so I googled it, and apparently there are things called 'wet dreams'. And boy, they weren't kidding about the wet part, everything was soaked."
Dean let out a guttural groan at her innocent description. "Fuck, Y/N, you're killing me here."
She frowned at him momentarily. "Should I not have told you?"
Dean shook his head, immediately reassuring her.
"No, sweetheart, of course you can tell me. Thank you for telling me. And I promise you that the thought of you touching yourself, while you imagine that it's my hands on you, is just incredibly hot and in no way wrong or disrespectful. And I'll be honest back and tell you that I actually did think about you, quite a few times over the last year, when I was alone and stroking myself, desperately wishing it was you."
Y/N's eyes grew. "Really?"
"Hell yes. Hope you don't think it was disrespectful."
Y/N thought about it for a second and then felt her breathing pick up at the thought of him wanting her like that for so long. She shook her head.
"No, I don't." She said shyly.
Dean leaned down for another kiss, but kept it short, pulling back to sip at the corners of her mouth.
She licked his bottom lip and he groaned. He brought his hand up to run his thumb across her mouth, staring into her eyes.
"Touch yourself now."
Y/N felt like fire was racing across her skin as he gave the suggestion.
"But you're here now. Why don't you just touch me."
A muscle jumped in his jaw as he explained his reasoning. "It's your own body, Y/N. You need to feel it for yourself first, before you let me in. Learn what feels good, get to know your own flesh."
He smiled slightly. "Do you remember anything from your wet dream, I can try and reenact it for you if you want." He gave her a little wink and Y/N felt her stomach tighten.
"I don't really remember, unfortunately, but..."
Dean cocked his head. "But?"
Chewing at her lips again, Y/N gave a little shrug. "I remember what I was thinking about when I wanted to touch myself before...can I tell you?"
Dean swallowed hard. "Fuck yes."
"Okay." She said, smiling shyly at his obvious interest. "First, I imagined you taking off your clothes. I'd seen you coming out of the shower room a couple days before with just a towel wrapped around your waist and it absolutely killed me."
Dean chuckled as he rolled away and stood up. He pulled off his flannel, tossing it on the floor and then reaching for the hem of his forest green t-shirt. Y/N sat staring at him, not moving.
He let his hands fall to his side. "Lay back, and let your hands move wherever you want them."
Y/N nodded, following his instructions. As he pulled the hem of his shirt up again, slowly revealing his smooth, lightly freckled torso, Y/N put her hands on her breasts, kneading them as Dean had, though it didn't feel as intense as when he did it.
Dean turned to throw his t-shirt over the desk chair, bending to pick up his flannel and hang it there too. When she was presented with his muscular back and round backside, a soft moan slithered out of her throat and she pushed her hand beneath the waistband of her shorts.
Dean turned back to face her and when he saw one hand moving under her shorts and the other squeezing her breast, he groaned deeply and ran a hand down the front of his jeans.
She could see the large bulge pushing against his zipper and she'd seen enough movies and tv to know what that meant.
"Jesus, Y/N," he said brokenly, "you're the sexiest fucking thing I've ever seen."
Y/N bit her lip as she swirled her middle finger around the small, sensitive nub that lay nestled within the warm, wet, folds of her body.
"Will you..." She groaned as she pressed a little harder. "Would you...can I watch you touch yourself too? I...I'd really like to see it. Is that okay?"
Dean walked closer to the bed and continued to rub against the bulge in his jeans. "Yeah, sweetheart, that's more than okay."
He popped open the button on his jeans and then slowly pulled down the zipper. He pushed the denim down over his hips so that he was left in only his black boxer briefs.
His voice was strained as he cupped his hand around himself. "Do you want me to be naked, or leave these on?"
"I'd...like to see all of you, if that's alright." Y/N said breathlessly, realizing that she would never have expected to feel comfortable enough with someone to have this kind of intimate conversation. Most extraordinary of all, she wasn't embarrassed anymore, a little shy still maybe, but not embarrassed.
She knew Dean meant everything he said, that they shouldn't be ashamed to ask for what they wanted from each other. They were partners in this giving and taking of pleasure, and she absolutely loved exploring it.
He nodded in response to her request. "Can I see you too, beautiful? I wanna see your fingers moving in and out of your body, all wet and slick, wanna watch you chasing ecstasy."
Y/N nodded breathlessly and pulled her hand free of her shorts, the damp of her body clinging to her fingers as she pushed down the slightly sweaty cotton.
Dean pushed form fitting briefs down his thick, muscular thighs and they were naked together at last.
Y/N found herself gasping at the size of the appendage protruding from Dean's body. She knew the mechanics of sex, which made her suddenly concerned that it simply wasn't going to work whenever they eventually got to that part.
How on earth is he supposed to fit inside my body? Y/N thought with an exhilarated kind of fear.
But she pushed that out of her mind for now, concentrating on the way Dean's hand was running up and down his length. He took his hand off only long enough to spit in his palm and then returned it to his shaft immediately.
He caught his bottom lip with his teeth and let out a groan that had Y/N's core muscles clenching, and suddenly desperate to be filled. She instinctively pushed her hand lower, and slid one slim finger inside the opening to her body.
She let out a stuttered moan. "Oh God, Dean." She breathed.
"Yes, sweetheart, I'm here. You're so beautiful like this, Y/N, so perfect. Just keep searching, keep seeking your pleasure."
Y/N nodded, eyes closed as she thrust down against her hand, sliding another finger into herself.
As she slid her fingers in and out, her thumb found the hard nub and began to press against it as she watched Dean standing over her, muscles rippling and tense as he bucked his hips into his hand.
She suddenly felt something like an electric shock shoot through her body and she cried out in pleasure and surprise, thrashing her head side to side on the pillow.
"That's it, sweetheart. Find it, find your climax, don't be afraid of it. I'm right here, you're safe. Let me watch you come apart, let me see you dissolve into shudders and moans."
His words acted like a catalyst and she felt herself falling over the crest of a wave, felt pleasure rippling out across her skin, tingling every nerve ending and making her muscles go rigid and her toes curl.
As the pleasure blinded her she was vaguely aware of Dean's deep grunt of pleasure and his curse, and she hoped he was finding the same kind of release.
When the colored lights finally stopped popping behind her eyes, it was just in time to see Dean tossing tissues into the garbage can beside the bed before climbing in next to her, and pulling her close against him.
He kissed her temple. "You okay?"
She nodded sleepily and snuggled deeper into his chest, loving the feeling of his warm, bare skin along the length of her naked body.
"I'm so good."
Dean let out a contented rumble from his chest and pulled the blanket over them both.
Before she dozed off, she leaned up to place a slow, closed-mouth kiss against his heavenly mouth.
"Thank you, Dean. This was another first I'll never forget."
Dean kissed the top of her head. "I'm glad, sweetheart."
As she was almost asleep she whispered words that guaranteed Dean wouldn't be sleeping for a while.
"Next time though, I want it to be your fingers inside me."
Dean let out a rumbling groan and felt himself start to harden slightly again.
"Yeah, sweetheart, the next first time."
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1. Jensen RPF + Any/All characters Jensen plays.
@lyarr24
@siospins2
@impalaslytherin
@akshi8278
@maggiegirl17
@candy-coated-misery0731
@nt-multi-fandom
@slytherinlyn314
2. Dean Winchester Fics Only.
@saikoswritings
@lgranger67
@carryonwaywardgirl
3. Any/All Fics (regardless of fandom/character.)
@sunshineandwings86
@kazsrm67
@sexyvixen7
4. Everything (includes fan vid/DOOL edits as well)
@unabashed-lover-of-fictional-men
@awkward-and-indecisive
@maliburenee
@supernatural4life2022
@spn730015
@b3autyfuldisast3r
@kickingitwithkirk
@waywardbaby
@foxyjwls007
@deanwanddamons
@deandreamernp
@deanwithscissors
@myloversgone
@snowlovespie
@leigh70
@all-alone-he-turns-to-stone
@fangirlxwritesx67
@charred-angelwings
@hopefuldreamers-world
@mysherlock221b
@jensensgotyoudean
@stixnstripesworld
@thoughts-and-funnies
@magssteenkamp
@norman1967
@princessmisery666
@eevvvaa
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@deepsketchsupernaturalcowboy
@b-i-t-c-h-i-e
@twirpbunwarrior
@mysweetlittledesire
@waynes-multiverse
@mrsjenniferwinchester
@bernasaurus
@jensenslady79
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tgtbata · 4 months ago
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the only day it ever snowed
full version here or here. for a request by @zmediaoutlet.
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beckawinchester · 1 month ago
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Day 14
A bad day
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zepskies · 11 months ago
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Hey could I request angsty and fluffy headcanons for Dean having a crush on reader but he thinks she has a crush on Sam but she actually has a crush on Dean back
Hey lovely!
So I kiiiind of already did this type of prompt with "Dean gives you an impossible choice" and its sequel, "Choosing Him."
But I'll do another imagine in this vein for you! ❤️
Pairing: Dean Winchester x Reader Word Count: 1,000 Tags/Warnings: Fluff, angst(ish), fear of unrequited love, mutual pining
Imagine: Dean reads you wrong.
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When Dean falls for someone, it's "slow and steady wins the race."
But the spark. That spark is instant.
He feels it with you.
Your pretty smile. Your "get it done" attitude that mirrors his. The way you know all of his references, whether it's movies or TV or music — you grew up learning how to tell time from what was on TV, just like him.
It's the way you laugh with him, share quiet moments of contemplation with him, and even moments of grief with him. Even when it's his grief, you always come. Whether it's to sit beside him, or share a drink with him, or make him something you know he likes, or get him to take a drive with you.
But realistically, you have more in common with Sam.
Both of you are bookish (nerds). You two get into heated discussions about Dante's Inferno and proper Latin translations. (You always accuse Sam of his pronunciations being off, while Sam argues, "At least I remember the whole exorcism. You think the damn demon cares if my vowels are off?")
You and Sam bicker. You playfully tease him, bring smiles to his face just as often as you bring them to Dean's. You're comfortable with him, playfully jabbing his arm or his chest when you mess with him.
Sam takes it with a smile, or a slight roll of his eyes, but always with fondness.
Dean can't help the churning in his stomach. Every time he thinks he has a read on you. Every time he thinks it's safe to maybe, one day, after a hunt, after an episode of Dr. Sexy, after you get out of the shower, after he's made you a home-cooked meal, after you sit with him and talk about everything and nothing while he works on his car — he thinks he might have a shot if he asked you out.
But he always falters, because he just can't fucking tell. He thinks you and Sam have something.
And Dean...he likes you. A lot.
More than he's ever willingly expressed.
But despite his reputation with women, he's never, and will never, step on his brother's toes.
Until he can't help himself.
It's your birthday. Sam got you a series of books he recommended to you last month. (Again, fucking nerds.) Dean got the booze and made the food to celebrate.
But you're surprised, and even a little teary when he brings out the cake he bought at an honest-to-God bakery. He even stood in line, waited 30 minutes to have them write your name on it, with little balloons. The frosting letters are drawn in your favorite color.
"Happy Birthday, sweetheart," Dean tells you. His tone is a little too soft. It's because he sees your unshed tears, and his heart clenches.
It's just a fucking cake.
Does it really matter that much to you?
But he still feels a well of warmth and pride in his chest. He turns to his brother with a smirk. "I win."
It's meant to be playful, but he kind of means it. Sam just eyes him knowingly.
"Sure," Sam laughs.
What the hell does that mean? Dean nearly frowns. But he's soon distracted — by you leaning in close to kiss him on the cheek.
He turns just in time (with slightly wider eyes) to see you blush.
That smile tells him something.
"Thanks, guys," you say to both of them. But your hand lingers on Dean's wrist, squeezing a bit.
At the end of the night, Sam turns in early. You stick around to help Dean clean up.
"Aw, stop. You're the birthday girl. I got this," Dean says, waving you off. You join him at the kitchen counter and lay a hand on his arm.
"Dean," you say softly. It earns his attention. You look a little nervous, your eyes falling from his, then meeting them again.
"What's the matter?" he asks. His brows furrow. He's thinking of your lips on his cheek. Unconsciously he glances down at your pretty mouth.
"Was wondering if you could help me with a birthday wish," you said.
A smile begins to tug at your lips, and Dean can't help but smile back. Intrigue, and a small tremor of something triggers up his spine.
"Oh yeah? What's that?" he asks.
You bite your lip. "Okay...I'm going to ask you this once. Yes or no. And if it's no...then we won't talk about it ever again and you'll have to wipe it out of your memory, because I don't want to make things weird or make you uncomfortable and I don't want to have to do something drastic, like leave the Bunker—"
Dean's smile falls as his brows raise in slight alarm. He also raises placating hands to stop your verbal flapping.
"Whoa, hey. What? What the hell kinda birthday question is this?"
You close your eyes and take a breath. "Okay."
Your eyes open, and as what happens far too often, Dean's captured by them.
"Close your eyes for me," you request.
"My eyes need to be closed to answer a damn question?"
"Damn it, Dean. Just do it, please!"
He lets out a slightly peeved breath, but he obliges you, shutting his lids. He really doesn't know what the hell is going on...until you lay a bracing hand on his chest and press a soft kiss to his lips.
For a moment, he freezes.
He inhales deeply through his nose as the surprise fades.
Relief floods in its wake.
A smile reaches his face.
But soon enough, before you can pull away, he grasps your upper arms to hold you in place. He dips his head down to kiss you in earnest. His lips find yours, gentle at first, and then gaining in passion.
He learns quickly the pattern of your lips, and the heady feeling of that knowing travels straight to his brain, stronger than the whiskey he drank earlier.
It's like you two were made to move together. To end up just like this.
You both are breathless by the time your eyes slide open and meet one another.
Dean's lips curve into a smirk. "How's that answer for ya?"
Your smile is beaming bright.
"Yeah, that works."
Chuckling, he pulls you in closer and tugs a strand of hair behind your ear, his thumb brushing your blush-warmed cheek.
And he answers you again.
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AN: Ugh, I'm sappy as hell. 😂 Hope you liked this! Let me know what you think. 😉
Read Sam’s version: “Sam reads you wrong.”
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mxltifxnd0m · 4 months ago
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heat wave ࿔ s. winchester
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summary: heat waves suck in the bunker
pairings: sam winchester x reader, sam winchester x fem! reader
word count: 1.7K
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warnings: no use of y/n, not beta'd, fluff, complaining about heat, nudity, suggestive content, one or two dirty jokes
a/n: i made a post about complaining about this heat wave that is happening in my area and decided to write about it. this was intended to be a blurb but it spiraled out of my control LMAO
(also i haven't posted this frequently in like... ever LOL. so please say thank you to sam winchester for being my muse)
please reblog and lmk your thoughts and opinions!! i wanna hear what you guys thought about the fic!
𝘴𝘢𝘮 𝘸𝘪𝘯𝘤𝘩𝘦𝘴𝘵𝘦𝘳 𝘮𝘢𝘴𝘵𝘦𝘳𝘭𝘪𝘴𝘵
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You hated the heat. Nope. Scratch that you loathed the heat. Despite growing up in hotter climates, you never grew to like the heat. You can tolerate it, but you've always preferred the colder months, where you can layer all you want and get warm and cozy.  
But with summer, there was so much you could wear until you were almost naked.  
The bunker could only do much to keep out the heat during the summer and keep the heat in when winter rolled around. An unexpected heat wave hit Lebanon, and since the bunker didn't have any AC or windows, it was practically hell on earth in the bunker.
Sam and Dean were out on a hunt, and you were stuck in the bunker due to having a nasty run-in with a witch that left you concussed and bruised ribs. They said the hunt was a quick salt and burn a state over, so they would be back in a few days. But in the few days they were gone, the heat became almost unbearable.
You spent the past few days stripped down to a bra and the shortest PJ shorts you had. You would have strolled around the bunker naked, but you were a little paranoid that Sam and Dean would come home early, and you didn't want to give Dean a free show. The amount of water that you had drunk could be considered criminal, but you managed to sweat most of it.
You even went out and bought multiple box fans for the library, war room, kitchen, and your bedroom (To hell with your boyfriend and Dean's bedroom. They could buy a fan for themselves.) because you could barely stand the stifling heat that managed to worm its way into the bunker.
The heat had gotten to the point where you were sprawled out on your back, starfish styled on the cool tiles of the shower room. This was your only saving grace in this place (and taking cold showers right before you went to sleep). When the tiles below you would get warm and sticky, you would just shuffle (drag) your body slightly to another patch of cold tiles.
You were so focused on cooling down your hot body that you didn't hear Sam calling for you when he couldn't find you in your room. He and Dean eventually found you on the shower floor.
"What the hell are you doing?" Dean's voice echoed off of the shower room walls.
"Finding reprieve from this god-awful heat." You sat up on your elbows to see Sam and Dean standing in the doorway, uncaring of your state of undress. Being a hunter and getting injured in inconvenient places had left you topless in front of the boys plenty of times and vice versa, so it left no room for modesty.
"This bunker doesn't have any AC or windows, and this heat wave has been terrible. You guys need to fix that." You said before sliding back down and moving to a patch of cool tile.
Sam's chuckling made you smile despite the heat. "Considering this bunker was built in the 30s, they didn't exactly have to worry about heat waves or AC."
Your smile dropped as you scowled at Sam's words. "I hate global warming. Also, how are the two of you not sweating your balls off yet?" You had noticed that they were wearing their flannels.
"We just got back and spent the past 10 minutes trying to find you. Safe to say we haven't spent much time in the bunker to feel the heat."
"Well, you're about to Deanie-boy, be prepared to strip." You went to take a sip of water from the bottle you had brought with you, only to find that it was empty.
"You would love to see that wouldn't you."
"It's nothing I haven't seen before." You said before getting up from the floor with a slight groan.
"Besides, I'd prefer to see a strip tease from a different Winchester." You winked at Sam as you walked in between the boys, giving his ass a quick tap as you left the shower room and headed toward the kitchen to refill your water bottle.  
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About two and a half hours later, the heat had gotten to the boys, and they were stripped down to their boxers, trying to survive. Dean ended up stealing one of the fans you bought and stashed it in his room, but even then, the fans were just blowing around the warm air that was in the bunker.
When it came time to eat dinner, you guys quickly got dressed because none of you wanted to spend another second in the hot bunker. The cool night air was like a healing balm over the heat wave as you guys found a diner that also had outside seating. After you guys were done eating, Dean drove the three of you around for a while with the windows down in the Impala, not wanting to go back to the stifling hot bunker.
You guys got back home at eleven o'clock, and the temperature in the bunker got significantly better, but it was still uncomfortably warm. You all headed to different bathrooms to shower off the stickiness that the three of you were already feeling.
You took your time in the cold water, not wanting to leave it just yet, but you eventually left the shower once your skin acclimated to the water and started to feel warm to you. You wrapped yourself in a towel and made your way to your room.
Once you made it to your room, you turned on your fan, cranked it to the highest setting, and dropped your towel. You didn't bother with any clothes or getting under the covers because you would throw them off of yourself the second you started to sweat. You crawled on top of your covers and rested your back against your headboard. You wanted to read a bit before you went to bed, so you grabbed your Kindle off of your nightstand and began to read.
About fifteen minutes later, you got a knock on your door. "Babe?" Sam's voice was muffled by the thick door.
"You can come in." You tell him, not looking away from your Kindle.
You heard the door open, and that's when you looked up at Sam entering your room. You caught his surprised expression as he took in your nude form and quickly shut the door. You saw lust flashing through his hazel eyes as his gaze traveled up and down your body.
Sam cleared his throat as he kept his eyes trained on yours. Ever the gentleman. You thought as you smirked at his reaction.
"Did you need something?" You asked, batting your eyelashes at your boyfriend as you placed the Kindle in your lap. Your eyes also wandered up and down Sam's bare torso as he was only in his boxers. His anti-possession tattoo stood out against his tan chest and was littered with scars that had faded with time.
You saw Sam swallow thickly as his eyes flickered from your chest to your eyes. "I was wondering why you weren't in our room?"
It was technically Sam's room before you moved into it. After a couple of months of dating, you found yourself sleeping in his room more often than your own when you initially moved into the bunker.
"As much as I love you, Sammy, I cannot sleep with you during this heat wave."
Sam frowned slightly as he made his way to your bed and sat on the edge of it. "Why not?"
You scoffed. "Because you're practically a human furnace, and as nice as it is sleeping with you during the winter, I just know I'll be soaked just sharing a bed with you."
A dirty smirk wormed its way onto Sam's face as his warm palm landed on your ankle and slowly trailed up your leg. "I'm glad I have that effect on you, but I already knew that."
You narrowed your eyes at him as you wriggled your leg away from Sam's grasp. "Ha, ha, you're so funny." You deadpan. "But I'm being serious. You radiate heat, which isn't fun when we're trying to survive a heat wave."
Sam started to pout at you. "But babe-"
"Nope. Not hearing it." You cut him off and shook your head at him as you moved your Kindle to your nightstand. "You're sleeping in your bed alone until this heat wave is over."
"Now, go back to your room." You gestured to your door.
A small huff left Sam as he got up from your bed. "Fine, but at least give me a goodnight kiss."
You rolled your eyes slightly. "Get over here, you big baby." Sam moved to the side you were lying on and bent down to kiss you.
You intended the kiss to be chaste, but Sam (being the little shit he is) had other ideas. He grabbed both of your cheeks with his hands and pulled you into a passionate kiss.  
It was unexpected, but you melted into the kiss as your hands instinctively went to his chest. He tasted like mint and something that you could only describe as Sam. Sam swiped at the seam of your lips, and that is what broke you from your Sam-induced haze.
You pushed him away from you and glared at him lightly. Sam just had a cheeky grin on his face.
"Nice try, now go to bed."
Sam still had a grin on his face as he bent down again and kissed your forehead.
"Goodnight, baby," He murmured softly against your forehead before pulling away.
"Goodnight, Sammy," You said with a soft smile as he left your room.
You turned to your nightstand and turned off the lamp that illuminated your room. Your room was engulfed in darkness as you shuffled further down your bed until your head hit the pillows. You fell asleep as your fan blew cool air towards your bed.
Little did you know, Sam ended up sneaking into your room once you were asleep and woke up in the morning soaked in sweat and having a moose of a boyfriend wrapped around your sweat-slicked body.
It's safe to say that you gave Sam a very rude awakening that morning.  
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s0urw00lf · 3 months ago
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hii!!
i was wondering if you could make a scenario of a protective!sam x reader? maybe an instance of reader gets taken by vamps and roughed up a bit. so when sam and dean find them, they’re kinda woozy from blood loss and opens up to sam about their feelings (kinda like a drunk confession) and upon learning reader feels the same way, sam gets extra protective and carry’s them out and just basically like a big shield.
i hope this wasn’t too rambley, but i’d love to see what you come up with!!💞
When push comes to shove
Pairing: Sam Winchester x reader
Warnings: tourture, blood loss, drowsy love confession
An: thank you for requesting and omg I love this idea so much and I may have taken it a bit to far… but I hope you like it 😁. I’m proud of myself I started this at 3:30 and finished it at five.
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You were walking down the road desperate for air, Sam and Dean had kept you locked inside the stuffy motel because you’d got a nasty scratch starting from the bottom of your back to your shoulder from your last hunt and weren’t really in the shape to be fighting off creatures of the night. You made sure to grab your knife and gun because even though you weren’t fit to fight you weren’t going to walk at night completely unarmed.
The street was lit up by the dim lights on the street and the air was cool and foggy, making your skin feel a little sticky but you couldn’t care less, this was the most you’d been able to do in days. Sam and Dean were currently out inspecting a nest of vamps that had migrated over from Michigan. And you knew better than to try and argue with them when they were both on the same page so here you were.
All of a sudden your instincts were on high alert, and you had no clue why. You kept walking at a steady pace, trying not to alert who or whatever made your nerves spike. All of a sudden you heard a snap behind you and the air stilled. You whipped around not seeing anyone and then it clicked vampires.
You grabbed your knife laced with dead man’s blood and called out, “Whoever you are don’t be stupid. Come on out.” Silence. You cursed at yourself for coming outside with a barely healed wound and not in the shape to protect yourself. You looked around in circles squinting to see past the line of trees to the right of you.
Suddenly something had grabbed you and threw you sending you flying back into a car that had been parked on the side of the road. The alarm blared in your ears and a searing pain shot up your spine and you were positive the stickers Sam carefully placed were ripped and your wound was bleeding freely.
You hissed in pain trying to get up to reach for your knife that you dropped. It was about six feet away but the blur in your eyes and the pain in your back made it almost impossible for you to move. You whimpered pathetically closing your eyes calling out for the one person you wished was there with you in that moment “Sam”.
“Sam’s not gonna help you love” a deep raspy voice said from above you. You opened your eyes , surprised at how close the voice was only to feel the man’s fist collide with your head knocking you out cold.
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Sam and Dean just arrived back at the motel after a not so successful ‘steak out’ as dean called it. They both entered the room ready to inform you that they hadn’t found anything. But the room was empty making Sam frown. “Maybe she’s in the bathroom?” Dean suggested with slightly concerned expression. Sam dropped his bag and hurried over to the closed bathroom door. knocking “y/n, you in there?” He asked putting his ear to the door. After no response he twisted the door knob pushing the door open slowly just in case you were in there any by some miracle just didn’t hear him.
When the door fully opened and he didn’t see you his heart practically stopped, he turned to Dean with a panicked look “she’s not here” he said. Deans face hardened “grab your stuff, let’s go”. Sam immediately complied grabbing his machete and vile of dead man’s blood. Nothing was going to stop him from getting you back.
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You woke up with a gasp at the feeling of ice cold water being poured over you. “There she is? Pretty one I’d say.” The same voice from earlier spoke. Your body felt heavy and you were in so much pain you couldn’t pinpoint exactly where it was coming from. “And she smells good” a female voice spoke. You couldn’t see the faces of your attackers clearly and you were almost sure you had a concussion and were suffering from major blood loss.
You were tied to a chair, and the air in the barn was hot, not doing much to numb the pain you were in. The lack of blood in your system made you groggy, almost as if you’d been drugged but it also made your composure slip which resulted in your talking. A lot.
“They’re gonna find you. And when they do your gonna wish you kept walking” you muttered groggily. You knew they heard you because they both laughed out loud as if you’d told a joke. “Oh and she’s funny, you know I might want to keep her” the female spoke again. “Whatever you want my love” the male spoke.
Suddenly you felt a sting on the side of your neck, you hissed “I’m gonna kill you, you blood sucking son of a bitch” you hissed in pain, you were able to focus your eyes to see your attacker holding your knife to your neck and another pain shot through your body. He’d pushed the blade deeper in “mhm I’m sure you will” he said sarcastically.
“How’s about a drink love” the man asked gestiring to the blood flowing down your neck, turning to the lurking woman behind him. “I’d l ove one” she said stalking closer to you. Suddenly you heard the heavy footsteps of more people vamps rushing in. “Someone’s here” another guy called from the entrance. The couple looked from him to eachother back to you. “Then let’s tell them where we are shall we?” He said before stabbing the knife into your leg. You screamed out in pain, white hot pain coursed through your veins and you cried. Tears streamed down your face and your head again went woozy.
You heard your name shouted by none other than Sam but as much as you wanted to you couldn’t bring yourself to lift your head. And for what seemed like forever which was probably about five minutes fighting occurred and you hadn’t realized when it stopped until you heard the clang of a knife hitting the ground beside you and hands gently crab your face and lift your head. Even though you couldn’t see through your tears you immediately recognized the outline of the younger Winchester brother and your heart soared. “Untie her” he quickly told Dean who had just reached you after killing the last vamp. Sam wiped your tears even though more would just replace the ones he wiped “it’s okay, you’re okay” he comforted you, making eye contact with the knife lodged into your leg. “It hurts Sammy” you cried leaning into him after Dean cut the ropes keeping you tied to the chair. “I know sweetheart I know, we’re gonna get you to the hospital, how’s that sound?” He asked gently lifting you up bridal style.
The pain that shot through your body made you feel like you were gonna pass out and you were until Dean lightly patted your face “c’mon kid I know it hurts but you gotta stay awake okay? Talk to me and Sammy alright” he asked gently. You tried to nod but you didn’t know if you moved at all. “I love you Sammy” you said the first thing that came to mind.
The brothers paused in shock put eventually shook it off, Dean took that as his que to walk ahead and Sam let out a soft laugh. “I love you too sweethear” he said softly. He couldn’t believe you’d just said the words he’d been dying to say to you. But he wouldn’t allow himself to belive that you meant it romantically and you knew he wouldn’t. “No like I really love you, like more than friends. I love your eyes, and smile, and the way you get shy when people complement you. I love your voice and how smart you are. And god your hair, I just wanna play with it all the time.” You ranted, listing everything about him that made you fall deeply in love with him. Sams heart raced, not knowing what to say back to you, and he was somewhat thankful you were a little dazed because you wouldn’t see how flustered it made him.
“And I like really love you too, everything about you. I could go on for days about things you do that make me love you” Sam said with a smile. His heart sank when you winced, he’d forgotten he was supposed to be getting you to the hospital. Sam held you tighter and moved with more of a purpose, and from that moment on he’d decided he’d give his life for you in an heartbeat and if the day comes that he feels any different then he’ll pray to god to send him right back to where he belongs. With you.
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headcaasefiction · 2 months ago
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I decided that I wanted to make my own Kinktober list for this year! I've finished 5 so far and mapped out pairings and summaries for the rest. All of these will be exclusively characterxREADER fics. I'm hoping I finish most, or all of them, but if I don't I'll just roll them out as one-shots in the following months.
I'll be writing for a few different fandoms: One Piece, Supernatural, The Sandman, Stranger Things, and Buffy the Vampire Slayer.
If you want to use my list and you write/draw for any of those fandoms, make sure to tag me, I'd love to read them or see your art!
Here's a list of the pairings I'll be writing for:
Day 1: Dean Winchester/Reader (Supernatural) Day 2: Dean Winchester/Reader (Supernatural) Day 3: Shanks/Benn/Reader (One Piece) Day 4: Mihawk/Reader (One Piece) Day 5: Sanji/Reader (One Piece) Day 6: Mihawk/Doflamingo/Reader (One Piece) Day 7: Cross Guild (mostly Mihawk)/Reader (One Piece) Day 8: Spike/Reader (Buffy the Vampire Slayer) Day 9: Demon!Dean/Reader (Supernatural) Day 10: Morpheus (Dream)/Reader (The Sandman) Day 11: Sanji/Reader (One Piece) Day 12: Zoro/Reader (One Piece) Day 13: Sanji/Reader (One Piece) Day 14: Eddie/Reader (Stranger Things) Day 15: Doflamingo/Reader (One Piece) Day 16: Sanji/Robin/Reader (One Piece) Day 17: Shanks/Mihawk/Reader (One Piece) Day 18: Eddie/Reader (Stranger Things) Day 19: Shanks/Benn/Reader (One Piece) Day 20: Shanks/Mihawk/Reader (One Piece) Day 21: Shanks/Mihawk/Reader (One Piece) Day 22: Shanks/Reader (One Piece) Day 23: Mihawk/Reader (One Piece) Day 24: Doflamingo/Reader (One Piece) Day 25: Sanji/Reader (One Piece) Day 26: Morpheus(Dream)/Reader (The Sandman) Day 27: Angel/Reader (Buffy the Vampire Slayer) Day 28: Sam Winchester/Reader (Supernatural) Day 29: Shanks/Benn/Reader (One Piece) Day 30: Mihawk/Reader (One Piece) Day 31: Dean/Sam/Reader (Supernatural)
Happy writing everyone! Can't wait to see what everyone creates this year!
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allmoshnobrain · 2 months ago
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Hello, lovelies! 
I decided to try taking part in kinktober for the first time this year. The stories will be all reader inserts and mostly less than 2k words unless I get in the mood to write longer ones. I’m not sure I’ll be able to post every day, but I did come up with a 31 prompt/pairing list that I fully intend to finish even if it takes a while!
Fandoms featured: Metallica/Megadeth, Venom (band), Call of Duty, Supernatural, Naruto 
You can also participate in the writing list with my FREE SPACE dynamic. There are some free spaces for specific pairings and you can shoot me asks with suggestions for kinks and plots featuring them. I will choose one for each character featured to write!
(I may still write non featured requests outside of kinktober, though. And if I get no asks for any of the characters I’ll just choose something to write about them on my own lol).
Free spaces available: Sam Winchester (SPN), Jason Newsted (Metallica), Cap. John Price (COD), Kakashi Hatake (Naruto), Cronos (Venom) 
I will keep posting my other stories and requests like Valley of Roses if I write them, even with kinktober going on!
You can check the full list with characters and prompts for the month below:
Week 01: 10/01 to 10/05
10/01: Caught in the Act + Voyeurism | Jason Newsted x Reader x James Hetfield
10/02: Gun Play | Dean Winchester x Reader
10/03: Biting + Hickeys | Dave Mustaine x Reader
10/04: Sex Toys + Public | Simon “Ghost” Riley x Reader
10/05: Blindfold + Group Sex | 90’s Metallica x Reader
Week 02: 10/06 to 10/12
10/06: FREE SPACE | Cronos (Venom) x Reader
10/07: Edging | Kirk Hammett x Reader
10/08: Mirror Sex | Cronos (Venom) x Reader
10/09: Breeding Kink | Kakashi Hatake x Reader
10/10: Size Kink + Gentle Dom | Simon “Ghost” Riley x Reader
10/11: Dacryphilia + Spanking | James Hetfield x Reader
10/12: FREE SPACE | Jason Newsted x Reader
Week 03: 10/13 to 10/19
10/13: Cockwarming + Begging | Dave Mustaine x Reader
10/14: Degradation + Angry Sex | Dave Mustaine x Reader
10/15: Phone Sex | Lars Ulrich x Reader
10/16: Public Sex | Cap. Price x Reader
10/17: Choking | Simon “Ghost” Riley x Reader
10/18: FREE SPACE | Cap. Price x Reader
10/19: Praise Kink + Daddy Kink | James Hetfield x Reader
Week 04: 10/20 to 10/26
10/20: Aftercare | Cliff Burton x Reader
10/21: Masked Kink | Kakashi Hatake x Reader
10/22: Car Sex | Cliff Burton x Reader
10/23: Filming + Threesome | Lars Ulrich x Reader x Kirk Hammett
10/24: FREE SPACE | Kakashi Hatake x Reader
10/25: Bondage | Lars Ulrich x Reader
10/26: Thigh Riding + Handjob |  Dean Winchester x Reader
Week 05: 10/27 to 10/31
10/27: Virginity Loss | Sam Winchester x Reader
10/28: Friends with Benefits + Keeping quiet | Jason Newsted x Reader
10/29: Period Sex | Kirk Hammett x Reader
10/30: FREE SPACE | Sam Winchester x Reader
10/31: Halloween Special: Sex Pollen + Fuck or Die | Dean Winchester x Reader
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lamentationsofalonelypotato · 9 months ago
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I Wish You The Best
Pairing: Dean Winchester x f!reader, Reader POV
Summary: You thought you had it all figured out, but when a certain green-eyed stranger keeps showing up in your life and turns it upside down you wonder if it’s best to push him away or if you should let him in. Reader is a grad student in medical school that doesn’t know anything about the supernatural world. This is the first fic in my Before You Go Universe, but can be read as stand alone.
Tropes: Angst, Fluff, Mutual Pining, Age Difference (Reader is early to mid-20's and Dean is probably early to mid-30's)
Word Count: 5.5K
Warnings: Some swearing (once or twice), Mentions of sex (not explicit at all), Implied sex, Self-deprecating Thoughts (Dean),  Dean might be a little bit OOC.
Note: This is told from Reader's perspective. Any references to the reader is made using you or your. There is minimal use of y/n. I tried my best to proofread, but nobody's perfect. If you don’t like, don’t read, but if you do like, you’re my favorite!
Internal monologue is in italics and is in first person.
Main Masterlist
Series Masterlist
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"Did you understand anything from that lecture?" Tim asks nudging your shoulder.
The sour smell of beer and sweat fades in and out of your nose as you make your way to the Science building through the mass of students on the way to the football game. It was a Thursday night, Thursday night for everyone else meant tailgating, cheap beer, and face paint, but Thursday night for you meant four hours in the anatomy lab surrounded by the oppressive smell of formaldehyde and bent over a table examining the internal intricacies of the human body.
It wasn’t unwelcome, you knew what you signed up for when you decided to go to medical school, but you still wished that the lab was earlier in the day instead of at 6 pm.
The air is filled with the dull throb of energy, pulsing with the music from speakers all over campus, and through the throngs of people that pass you on the way to the stadium. The buzz of excitement in the air vibrated through your nerve endings. If you paid attention to how well the football team was doing, you would have known that tonight was the championship, but the closest you got to pigskin was the bag of pork rinds in your backpack and the occasional football player that asked you for help finding research materials during your shifts at the library.
"Nope." You reply jostling past a group of guys toting a giant stuffed pig wearing jersey of the school’s rival while they catcall some girls up ahead dressed from head to toe in bright red.
"Then why did you keep nodding?"
"Because Professor Drake was staring right at me!"
"You didn't have to make eye contact."
"It's a little late for that don't you think?" You smile up at him. He's taller than you, with dark hair falling forward into his glasses and a lean build. "But it's alright, I'll just binge watch YouTube videos."
Tim laughs adjusting his backpack over his shoulder. You had been lab partners since your first year, randomly assigned and forced to collaborate, but after many late night study sessions and mental breakdowns, Tim was one of your only friends.
“You seem to spend a lot of time on YouTube." He smiles.
"It's free education."
"Seems ridiculous to pay all this money just to learn it on YouTube."
"If YouTube handed out degrees for watching videos I’d be a doctor by now. I’d probably also have a degree in culinary arts.” You look down to check the watch on your wrist. You were both running late for lab. Dr. Welsh hated it when students were late, in fact, he was notorious for locking the door. Each week there was always some poor soul that banged on the door for entry, but Dr. Welsh knew no mercy. One time, you witnessed another student attempt to sneak in through the window an hour late. Dr. Welsh made them go back out the way they came, despite the lab being on the third floor.
At least the student brought a ladder with him.
“Culinary arts?”
“I like pie. Plus baking helps me cope with my stress.” You knock into his shoulder to shut him up. “What? You don’t watch anything weird on YouTube?”
“I usually start watching videos to understand the lectures and suddenly it’s been 7 hours, it’s 3 am and I’m watching a timelapse of metal rusting.”
“We’ve all been there buddy.”
"Hey doll-face!" You hear from somewhere behind you, but you ignore it, believing it to be another group of guys who splash beer over the sidewalk.
You glance down at your watch again.
"We're not going to be late." Jake says sensing your anxiety. "We've got 5 minutes."
"Early is on time, on time is late, late is inexcusable." You sing-song.
"Dr. Welsh embroider that on a pillow for you?"
"No it’s just-"
Someone grabs your backpack and pulls you back a step. What the- You whirl around prepared to cuss out a drunken frat boy, but you weren't expecting Dean Winchester.
"Dean." You say in surprise.
He looks better than you remember. Dean's wearing a red flannel covered by a black jacket, his hair tousled just the right amount to look effortless, his green eyes crinkled around the edges as his mouth pulls into a smile that makes your knees weak.
Your relationship, if you could even call it that, began your first week of classes, two years ago. You had just moved into your apartment and met your new roommate, but instead of going out to the new student mixer with her, you decided to stay in and unpack. It was past midnight when you heard a commotion in the apartment next door and when you opened your front door to investigate, you found Dean in the hallway leaning against the wall.
His clothes were torn, he had a knife in his hand, blood was soaked through the front of his shirt, but when his eyes met yours, you weren't afraid. He looked so broken, so small that you had to help him. So you pulled him into your apartment and stitched him up the best you could, while he tried to lie about how it happened and explain why he looked like he'd been through a blender. Dean had never been good at lying to you, not even then. He was also the biggest baby you had ever met when it came to wound care.
In the months that followed Dean continued to show up, each time with injuries less and less life threatening asking you to help him, until one day he showed up perfectly fine and continued to show up. You would spend every minute together for a few days and then he would leave like nothing happened, only to show up again in a few weeks and it would start all over again. 
Sometimes you thought that he wanted more than just a few days together, but then he would just leave, not giving you any other explanation. You hadn't expected to fall for him as hard as you did, but each time he left it broke you. You found yourself hoping each day that he would show up, only to be disappointed when he didn't. Days would drag by fading into shades of gray until finally Dean would show up and everything went back to color, only to sink back into monochrome when he left. The last time you had seen him was a month ago, when you told him that you couldn't do this anymore and told him not to come back.
But now he was here, again.
"Hey Doll-face." Dean smiles wider.
You try to ignore how your heart stutters in your chest when he smiles at you.
"Do you know this guy?" Tim asks you taking a step forward to put himself between Dean and you.
Dean's eyes trace Tim, smile slipping into confident smirk as he sizes him up. He opens his mouth, but you interrupt whatever thought was about to come out.
"Unfortunately I do." You sigh. "Tim can you give us a minute."
"Sure. But-"
"I know." You say, understanding that he was going to remind you what time it was. "We won't be late."
"I'll be over there." Tim puts a healthy distance between the two of you, far enough to give you space, but close enough that he can see you.
Dean is still smirking at him. "Boyfriend?" His eyes flit to yours, amused.
"Lab partner." You adjust your grip on your backpack unsure what to do.
I said everything I needed to say the last time. I thought that was it. Did he think I didn't mean it?
You think about the last time he was here, when you told him that you couldn't do this anymore and when he finally left, how you skipped all your classes and stayed in bed for two days clutching a pillow to your chest and wishing that it was him. It had felt like the end. The end of whatever the hell this had been. Sometimes you wished that you had defined it the first time you slept together, wished that you had told him you didn't do that ever, that you didn't just sleep with people without feelings because you knew sooner or later it would end up like this.
Then again you knew that you always had feelings for him, since the moment you locked eyes with his the night you met.
"He’s cute. If you’re into that geeky kind of thing. Though you could always date Sam-"
"What are you doing here?"
"I was in the neighborhood. Plus I didn’t want to miss the big game.”  Dean's eyes flit to the mass of people swarming around you, shouting and singing as they stumble down the cracked pavement. The dark shadows of the buildings stretch long over campus, illuminated by the lamplights that line the sidewalks.
"You should have called"
"I did. You never pick up" He arches a perfect eyebrow.
"Most would take that as a hint"
"Well Sweetheart given my profession you not picking up made me worry."
By now you knew exactly what he did. Despite Dean not acting like he wanted a relationship, when all was quiet and it was just the two of you laying in bed he confided in you, told you things about his life that made you hold him close and wish that you could make him forget all about it. You loved those soft moments with Dean, when it felt like more and you could imagine that Dean wanted to be as wrapped up in you as you were in him.
Your heart clenches in your chest as you try to forget it all, forget the day he walked into your life, and forget how much you like him.
"I can’t do this with you right now, I’ve got a lab in 3 minutes." You turn towards where Tim is standing, prepared to leave.
"Come on you can blow off one lab.”  Dean grabs your backpack turning you back to face him. “We can go to the big game. You know I can’t say no to free beer-“ The look in his eyes is joking.
He doesn't understand.
You shake him off. "No I can't Dean. This is important to me. This is my life. I can't drop everything just because you show up out of the blue."
"It wouldn't be out of the blue if you picked up your phone." His smile dips into an attractive pout that makes it very difficult to think.
"Dean why are you here?"
"I told you, I was in the neighborhood-"
"We talked about this. I can't do this anymore."
"I remember you talking about it."
"Yes and I remember you leaving." You snap as the memory of the last time you saw him rises in the back of your throat. You think about the days that followed, when you couldn't focus and flunked a test. 
"Y/n-“ Dean sighs.
"Look, I like spending time with you, but I can't keep doing this to myself. You show up, we spend every second together for days, and then you leave. It would be one thing if we were trying to do long distance, but we’re not.  All I get is radio silence for weeks and then you show  up all over again like nothing happened, expecting to pick up right where we left off, and the cycle begins all over again."
"I don't go radio silent for weeks. It’s you that doesn’t pick up your phone or text me back.”
"Yes you do and I can't do it. I won't do it. Because every time you leave I wonder if it's the last time I'll ever see you and-" You take in a breath to stop the ball of emotion that lodges itself in your throat. "It does something to me. And I'm not saying that what you do is any less important than what I'm trying to accomplish here. I’m not telling you to stop hunting. But this is my life Dean, my future. And I don’t want to put that in jeopardy because you show up every few weeks when you’re feeling restless. I want more than a few days every few weeks. I want more and I'm worth more. And if you can't give that to me that's fine, but please stop coming around and so I can find someone else who can."
The expression on Dean's face shifts, it's no longer the playful smirk or attractive pout, it almost looks heartbroken.
But that can't be right. Dean doesn't see me that way.
You look at where Tim is waiting for you to avoid Dean's gaze. He’s looking down at the watch on his wrist and you can feel his apprehension.
"I've got to get to my lab." You turn away from Dean, but stop halfway to Tim. "It was good to see you Dean. I wish you the best."
As Tim and you begin to walk away, you can feel Dean's eyes on you the whole way up the stairs into the science building, but you refuse to turn back.
"Are you okay?" Tim whispers.
"I will be. Let's just go before Dr. Welsh locks the door." You mutter while pushing down the guilt that rose when you thought of how Dean looked when you walked away.
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Despite Dr. Welsh’s attempts to lock the door, you were far too angry with Dean to let another man stand in your way, so when you and Tim arrived to lab 10 seconds before the clock struck 6, you shoved your boot in the door before Dr. Welsh could shut it. And by some miracle he let you in. Maybe it was the murder in your eyes.
Tim had been stunned, you were usually more reserved, not quick tempered. But everything that happened with Dean rubbed you the wrong way.
You couldn’t decide if you liked him or hated him. Right now the hate was winning.
How dare he? You thought to yourself, hand clenching on the scalpel so tightly that Tim backed up. How dare he just show up again after I told him not to?
“Y/n, are you okay?” Tim had asked.
“I’m fine. Don’t I look fine?” You’d snapped at him.
Even Dr. Welsh had given you a wide berth through lab.
 After you cleaned up everything it was 10:26 pm, which meant you had a little time before your late shift in the library.
“Did you want to go see if that shawarma food truck is still parked around the corner?” Tim asks hesitantly.
“No. I’m just gonna go to the library and study before my shift.” You mumble, shouldering your backpack and ignoring the urge to think about Dean.
Hopefully he took the hint and he’s gone. The thought brought a prick of guilt. Would that be the last time I ever saw him? Would those be the last words I ever said to him? You fight the urge to call him, to apologize, because the one thing you had wanted to say was that you liked him and you didn’t want him to go, you wanted him to stay in your life permanently. Sure long distance was hard, but for him it would be worth it.
“Oh.” Tim pauses for a minute. “Are you sure you’re okay?”
“Huh?”
“Well that Dean guy. You seemed kinda upset.”
“I was- am. But it’s okay, give me a few hours I’ll be over it. I’ll see you tomorrow.”
“Sure.”
“Make sure to send the link to that Timelapse of metal rusting.” You try to smile, but the joke falls flat.
“Okay.” Tim watches you go.
The library was only a 9 minute walk from the science building, but it still felt too long. You longed to be lost in your notes, to think of anything else other than Dean, but you couldn’t.
Why did he have to come back? Why couldn’t he have just let it lie? I was doing better-
You think about the weeks that followed his last visit, a haze of homework, tests, and work.
Well, I was doing okay.
The thrum of music is still in the air, but now less people pass you as you walk down the sidewalk, and the ones that do are holding hands and laughing. Your thoughts shift to Dean again.
I like him, but I have to get over him because it’s not going anywhere. You think about the first time you slept together. Maybe this is my fault, maybe I should have defined this from the beginning. I mean, I know the kind of person he is…
That thought makes you pause. Sure the first few times you’d patched his wounds Dean was sexy and flirty, but all the times that followed he seemed, sweet, charming. It wasn’t that you spent every moment in bed, he had taken you out to dinner at the diner down the street, fought with you over the last slice of pie, took you to a bar for drinks  where he shamelessly beat you at pool, other times he waited for you to be done with your classes to make sure that you didn't have to walk home alone at night. You remember how mad he had been when you told him you did that, but gas was so expensive and it was easier to walk the four blocks.
Someone grabs your arm from behind, pulling you out of your memories, and you finally snap. Using the only self defense move you knew, besides S-I-N-G from Miss Congeniality, you knock off the hand and flip the offender over your shoulder prepared to spray them in the face with the mace in your pocket.
But then you realize who it is.
Dean frowns up at you from the ground. “When I taught you that, I didn’t expect you to use it on me.”
“Just be happy that I didn’t pepper spray you.” Your eyes narrow.
 Maybe I should. It would make me feel better.
“Would have been the highlight of my night.” He stands up from the ground brushing off the front of his clothes with a pointed look.
“Dean what are you still doing here?”
“I want to talk.”
“I’ve said all I need to.”
“But I haven’t.”
“I don’t care. You’ve heard what I need to say and I’m sick of you not listening.”
“Y/n-“
“Fine, I’ll say it one more time, but listen this time.  I've never, never depended on anyone else in my life. It's been me, me for a long time.” You poke your finger into his chest to emphasize your point. “Then you just sauntered in and changed everything. You made me care about you, worry about you, and you made me depend on you showing up in my life. Every time you leave it breaks me. Every time I’m in a funk for days. The last time you left, I cried for two days and I didn’t go to any of my classes! I'm trying to be serious about my life. And I can't do that if you show up every few weeks and make me expect something and then leave a few days later and I'm devastated.”
Dean’s eyes widen in surprise. “I didn’t know that.”
“I have to get over you Dean, and I can't do that if you keep showing up. So please just go.” You turn away from him.
His hand comes down on your arm again to turn you back to him. “I don’t want you to get over me.”
“What?”
“Do you think I like leaving you? Do you really think it’s that easy for me?” He looks hurt.
“It certainly seems to be when you walk out after a few days with a smile like it means nothing! Like I mean nothing-“ You fight the tears that burn against your eyes. You wanted to be something for him just as much as he was something for you, but you were afraid. You hadn’t depended on anyone since you graduated and moved away from home. You weren’t used to needing someone in your life this much.
"You mean everything!” Dean shouts grabbing your shoulders. “It’s me that means nothing."
You blink your eyes for a second, not comprehending what he’s trying to say. "Dean what are you talking about?"
"I didn't think you wanted that-" He looks down.
Your eyes trace the slump in his shoulders, the frown on his handsome face, and the way he won’t meet your gaze.
What is he talking about?
You try to think of a time that you’d seen him look so vulnerable, but the only time you imagine was the night you met.
"Wanted what?"
"Me.” Dean’s voice is a whisper.
"I'm confused."
His eyebrows are furrowed, lips pressed into a tight line. “I’m nothing like you.”
“What does that have to do with anything?”
“You’re a little younger than me and you’re smart and you’ve got this bright future ahead of you. You don’t need someone like me dragging you down-“
“Someone like you? Dragging me down? Dean what are you talking about?" You can't comprehend what he's saying. You reach up to cup his cheeks, but Dean pulls back from you, glancing away.
“I didn’t go to a fancy college, I barely finished high school. I’ve spent most of my life in motel rooms  committing credit card fraud and trying not to die.  And then I met you. You’re funny and caring and so smart, and  I just thought that you would like it more if I came by every once in a while to relieve some tension. I didn’t think that you would want me to stay.”
He didn’t think that I would want him? That can't be right. Dean is so confident usually. You search his face and see the genuine vulnerability behind his green eyes.
“Are you serious?” You ask him.
He doesn’t say anything.
“Dean, you are smart-“
“Not the same way you are”
“Dean.” You can’t help but take his hand. Dean’s green eyes focus on yours for a second, wide and open. “You don’t have to go to college to be smart. You’re resourceful and you know more about supernatural creatures than anyone else. Even the top scientists and doctors in the world don’t believe in them and they went to stuffy old colleges and fight with one another over who’s smarter. I don’t care that you didn’t go to a fancy college. What you do is important, probably more important than what I’m going to do. You protect people, you’ve saved the world more than once, and sure maybe it’s not glamorous to some people but it is to me.”
His eyes widen in surprise.
“Have you thought that maybe I like spending time with you because you’re so different than the people I see everyday?” You ask him softly, squeezing his hand.
“No.” Dean mutters.
“I wasn’t born with a silver spoon in my mouth, I don’t have lavish wealthy parents bankrolling me. My dad is a mechanic. I work two jobs and send him money so I don’t have to worry about him. Sometimes I feel like a fraud. But when you show up I don’t feel like a freak. With you I feel like I don’t have to pretend, I can just be me. And I like you, a lot. This has never just been about relieving tension or sex for me. Ever. I mean it’s nice-“
“Just nice?” Dean raises an eyebrow.
You flush bright red. “I like spending time with you without that too. All the times we spent laying in bed or went to a bar or went to get food, and we talked were equally as wonderful for me. I like talking with you. I like hearing about your life. I just assumed that you had someone in every state that you visit when you’re feeling restless and that you didn’t want a relationship.”
“There’s no one else. Hasn’t been since I met you.”
Deans eyes lock with yours as you comprehend what he just confessed.
“Really?” Your voice is only a whisper.
“Fuck I’m not good at this romantic comedy shit-“ He mutters to himself shaking his head. “I like you too. I wish that I could be here all the time. I hate leaving you. It’s too quiet. When I’m not here all I do is think about you, what you’re doing, how your day was.”
Your entire body explodes with his words, heart beating so fast you think it’ll grow wings and take flight.
“When I was younger I used to laugh at Sam because he wanted a normal life, but with you I understand.  You’re so different than anyone I’ve ever met and it hurts me when I’m away from you.” Dean continues with a soft smile that makes you lose all feeling in your legs.
He takes your other hand. “I understand that what you’re doing is important and I’m not asking you to quit school. All I’m asking is that you give me a chance. I want to make this work. I know that long distance isn’t easy, but I want to try.” His eyes search yours, begging for a answer, but you can barely breathe let alone speak. You watch his face fall as he takes your silence as your answer. “But I understand if you don’t want to, because you are worth more. You’re worth more than a few days, than a phone call or a text. You deserve someone who can be here with you all the time. You’re worth more than what I can give you. And you shouldn’t have to settle-“
You grab the front of his flannel because you can’t think of anything to say and pull him down to you for a kiss. Pins and needles trace down your spine as his soft lips move against yours. He smiles against your mouth, folding you into him, his large hand on the small of your back just under your backpack causing warmth to shoot down your spine. You lose yourself in the way his body fits around yours
“I’m not settling.” Your hands cup his cheeks as you look deep into his eyes. “I never want you to feel that way, because you are worth a hundred of any man I have ever met in my life. And if it’s my cross to bear to make you understand that every day of my life, then so be it. Because I would be lucky to spend any amount of time with you. I don’t want anyone else. I just want you, Dean. I’ve wanted you since the day we met and every day after. And I’m yours as long as you want me.”
Dean’s smile breaks open something in the pit of your stomach and goosebumps scorch across your skin. “I can’t imagine not wanting you.” He presses his forehead against yours.
You stand there with his warm hand pressed into your back trying to think of another time that you felt even a fraction of what you feel for him. You think about your high school boyfriend, about a few of the guys you dated in during your undergrad years, but you come up with nothing. Because you can’t compare him to anyone else you’ve ever met. And it hurt you to think that Dean thought so little of himself in the grand scheme of things.
He leans down to kiss you again, pulling you against his chest so tight that everything blissfully falls away.
“Are you hungry?” He whispers against your lips after a minute.
“Yes, but my shift at the library starts soon. I’m there til 2.” You tighten your hands at the back of his neck, not wanting to let him go.
“Okay. I’ll go with you.”
“Dean it’s okay if you just want to go back to my apartment and sleep. I can give you the key-“ You notice the dark circles under his eyes, but you know that Dean wasn’t one to complain about being tired.
“It’s worth being tired if I get to see you.” Dean smiles. “But I’ll go get us some food, because I’m hungry too.”
“Don’t forget the pie.”
“Have I ever?” He brushes his lips to yours one more time, but you don’t remove your arms from around his neck. “You’re going to have to let me go doll.”
“Just 5 more minutes.”
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You spend the weekend together in your apartment. All those blissful moments together solidify the thought that this is real, that this time it’s going to be different. Every night going to bed with Dean tucking you against him and waking up every morning with your head on his chest feels like a dream, and you never want to wake. Every kiss and intimate moment between you feels like more, and you have to keep reminding yourself that it isn’t just sex, hasn’t ever been just sex. Dean wants to be there with you all the time, hold you close to him and share things with you. And this time you finally understand that you do help him forget and know that you do bring him as much comfort as he brings you.
When Monday comes and Dean has to go, you try not to think of it as the end.
Dean leans back against the door of the Impala, his hands on your hips, green eyes blazing in the sun, but it’s his eyes that warm you more than the sun’s rays.
"Sweetheart-" Dean begins, sensing what you’re thinking. His thumbs rub smooth circles against waist where your t-shirt rests.
"I know." You press your face into his flannel, inhaling the scent you ascribe to Dean. He smells like oil, leather, and the spicy scent of the soap he uses that tickles your nose.
"Hey." His free hand comes under your chin to raise your gaze back to his. "I promise I'm gonna come back. I promise that we're going to make this work. It’s going to be different.” He cups your cheek, eyes soft and understanding.
“I know, but you’re still leaving.” Your tighten your arms around his chest.
“I wish I didn’t have to. But Sam called, he needs me-“
“I know.” You breathe.
You don’t want Dean to feel any worse than he does about leaving, especially when you remember what he said to you a few days ago, about you deserving more and about how he wished he could be more for you. Deep down you know that both of you are determined to make this work, so you put on a smile.
 “It’s okay.” You gently rub his back.   “You’ll be back in 2 weeks and I’ll be on spring break in a month.”
“Does that mean I’ll get to see you in a bikini?” Dean grins.
“You’ll have to wait and see.”
“Hmm. Well until I see you-“ He raises his right hand from where it rests on your hip to remove the large silver ring from his finger. "Don't panic, it's not an engagement ring." Dean's smile breaks you a little.  "Just me promising that I'll come back, that I'll call and text you so much that you'll be sick of me." He slides the ring onto your thumb, the weight comforting.
"I could never be sick of you."
“Just you wait.” He winks, holding your hand to his chest. “I bet I can prove you wrong.”
“I welcome the challenge.”
The kiss goodbye is bittersweet, but you hold yourself together, refusing to cry as Dean gets into his car and leaves. You watch the Impala disappear around the corner, taking your heart with it, but just as it does your phone rings.
“Hello?”
“I miss you.” Dean’s voice fills the line and this time you can’t stop the tears.
“I miss you too.”
“I promise I’ll be back in two weeks.”
“Okay. Please be careful.” You remember all the stories he's told you over the time you’ve known him, all the horrible things that happened to him and Sam. Sometimes you wish he hadn’t, because you can’t help but worry.
“I’m always careful.” You can hear him rolling his eyes.
“As the person who has spent the past 2 years patching you up, I can say with certainty that you are not always careful.”
“Then I promise to be more careful than usual.”
“I’ll hold you to that.” The wind picks up, pulling your hair from the ponytail at the back of your head.
“I’ll call you when I make it back to the bunker.”
“Good.”
“Bye Sweetheart.”
“Bye Dean.”
Your gaze drops to the heavy ring on your thumb and you hold tight to the hope and belief that this time is different, allowing the memories of the past few days to brush away any doubts that threaten the thought of what the future will bring.
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Thank you so much for reading!  If you'd like to be added to the taglist for future fics in this universe please let me know! :)
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so-much-for-the-seashells · 5 months ago
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Baking With BF!Dean Winchester Headcanons
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✨ Dean Winchester x GN!Reader ✨
*sighs in 2014 was 10 years ago* Minors do NOT interact, this is not “rizz-ing!” Off you go!
A/N: I love writing these because they’re like half baked yet surprisingly endearing thoughts and it’s fun haha.
Icons by me!
All notes are appreciated! Hope you enjoy!
Content Warning: I have a bad sense of humor and make some sex jokes but nothing too explicit, at least I think so. Definitely still 18+
( ˘ ³˘)♥︎ ♥︎ ♥︎ ♥︎ ♥︎ ♥︎ ♥︎ ♥︎ ♥︎ ♥︎ ♥︎ ♥︎ ♥︎ ♥︎ ♥︎ ♥︎
-3 favorite things to bake with him
1. Pie (obvs)
2. Brownies (sometimes with pot…)
3. Cookies (all kinds)
-okay, now that that's been established...
-one day you had jokingly suggested the bunker should do a cookie jar
-this was taken seriously; not only by Dean, Sam and Cas; but also by literally every regular passerby. Even Rowena's made a batch of red velvet cookies. (We threw those ones away, we couldn't trust that they weren't poisoned, made of blood, or both)
-but if it's just the usual crew (you, the brothers, and Cas) then you have a weekly rotation
-and Dean regularly suckers you into "helping" him, even though you both knows he’s capable of being a big boy (and I mean he is a big boy if you catch my drift) and doing it himself
-those candy apple green eyes work wonders
-anyhoo
-one of his favorite, stupidly cheesy things to do is as follows:
-you’ll have a taste of the batter/dough/filling, as one does (it’s always good cause the two of you together are an unstoppable force in the kitchen) (alone is a different story- it’s usually Kraft Mac n Cheese cups)
-and while you’re trying it, making faces, he’ll look over and innocently ask if he can try it
-like “Can I get some, sweetheart?” (And yes he most certainly can get some.) (batter, I mean) (definitely batter) or “can I try some, doll?”
-and no matter how many times he’s tried it you’ll say yes
-so he’ll lean down, cupping your cheeks in his rough hands and kiss you as passionately as humanly possible
-like, these kisses could literally bake the cookies or whatever because of how hot they are
-and he’ll make sure he really gets to try it
-and then he’ll pull back with a smirk, cause he’s done it at least 30 times before and you still let him and still like melt into a puddle every single time. Without fail.
-you guys like to put on Disney soundtracks in the background when you bake. High school musical and Moana primarily, but he’s also taken with the soundtrack of Julie and the Phantoms. (He complained about the show being unrealistic supernaturally speaking and then was adamant that there should be a season two and cancelling it was a crime worthy of hell)
-also, rock, obviously. As a fan of Bon Jovi, you best believe you sell him on them and slow dance to Bed of Roses while things are in the oven. It’s only right.
-if you’re listening to heat of the moment and Sam the baby giraffe walks in he will get those sad eyes, making both of you scramble to make him something else, like some keto hidden veggie brownies or some shit, to make him feel better
-now, in specifics
-pie is for fun. You two usually make one to split for after dinner. Roughly once a month, but should be more often. Well, that’s not fair if you count creampies
-apple is his favorite, ofc. You use Mary’s recipe, and you’re the only person in the whole wide world that he trusts with modifying it in any way
-you also make them for him if he’s sick or if you guys have for some reason had a fight. The latter is rarer, but does still happen on occasion
-it’s okay though, because pie will always make things better
-cookies are almost exclusively for the jar. These are made on random frequencies, usually a lot at a time.
-he likes butterscotch a lot, and you find a way to mix your favorite flavors into either one monstrosity or one beauty of a cookie
-you guys have in fact made your own recipe. It’s awesome. Like, prized possession material.
-and then brownies
-they’re literally just pimped up store bought mix. Preferably Ghirardelli, for maximum bougie-ness
-and then sometimes you guys add some fun time grass
-you’ll do that when you just want to have a soft night. You’ll always way up to him laying on you and holding you like a koala though- may your back be prepared
-overall he just really enjoys spending time with you in any way that he can and baking is a great way to do that
-Dean Winchester is precious
-I rest my case
If you have any ideas for more headcanons, send a request! My box is always open!
Xx
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