late night dean feels

Puppy Love - Part 1

Pairing: neighbor!Dean x Reader

Word Count: 1,470

Summary: The reader’s dog wanders off and she finds him hanging out inside of an Impala that belongs to her gorgeous new neighbor.


You swear to god your dog is a ninja. He’s constantly sneaking off and getting into trouble. He’s worse than a little kid. He’s a 100 lb German Shepherd for Christ’s sake. You should be able to keep track of him.

“Murphy! Come here, buddy!” 

The beautiful beast is too smart for his own good. He’s a troublemaker for sure. He needs to know what’s happening at all times. You have a slight suspicion that he thinks he’s a police dog.

You quickly search the house and the backyard, you’re not surprised that he’s no where to be found. He tends to invade your neighbors lives. He’ll just waltz right into someone’s yard or house if he can. Sigh. You walk out your front door and start looking around.

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Imagine Dean getting put on the spot by Sam and finally asking you out.

Intro: You’ve known the Winchesters for over a year now. You met them at your aunt Jody’s house one night when they showed up unexpectedly; that in turn led to them staying for dinner. You’ve had a crush on Dean ever since you first laid eyes on him. For the next few months, due to sly conversations with Jody and casual text messages between you and Dean, you managed to make sure that every time the Winchesters dropped in for dinner, you were there. 

As time progressed, so did your feelings for Dean. Casual texts turned into late night - deep conversations and flirty behavior during dinners at Jody’s. Your feelings for each other were clear to everyone (including each other) but neither you nor Dean have worked up the courage to ask the other out on an actual date yet.

During one of the Winchesters’ recent hunts, Sam made a childish bet with Dean that if he lost, he’d have to ask you out at the next dinner. Of course, Dean accepted, thinking he’d win. He ended up losing the bet but didn’t view it as much of a loss since he was planning on asking you out anyways; he just wished it was on his own terms.

“Do it already!” Sam whispered close to Dean’s ear while nudging his arm. It was probably the 6th time tonight that he’s done that, distracting Dean from the good-humored banter going on at the dinner table. Dean cleared his throat and rolled his eyes, clearly fed up.

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It’s Just a Party, Janet

Summary: You, Sam, and Dean attend a high school reunion during a hunt. You really, really hate parties.

Characters: Dean x Reader, Sam

Warnings: Anxiety, panic attack, Dean being a bit of a jerk.

Words: ~2.4k

A/N: Whoops I’m late for @hannahindie and @pinknerdpanda‘s Dr. Frank-n-Furter’s Partici…..pation Challenge. The story itself is totally unrelated to RPHS (and for the sake of it, I’m going to pretend the movie doesn’t exist) but I’ve used a bunch of quotes, all of which (that are intentional) are bolded.

Originally posted by winsync

“You really think this will work?” Sam asked.

“Oh yeah,” you nodded. “I went to my–” the next word was mumbled incomprehensibly– “year high school reunion and I didn’t remember half the people who talked to me. We’ll fit right in.”

“I’m sorry,” Dean said, a hint of humor on his tongue, “how many years was it?”

“Don’t start with me, old man.” You leaned across the Impala’s bench, looking between the Winchesters. “So do we know our backstories?”

“I’m a rich city councilman, I was in the leaders of tomorrow club, and I’m engaged to you,” Sam recited.

I just love success,” you said, pressing a joking kiss to his cheek.

You and Sam didn’t have feelings for each other, but that was part of why you always chose to pretend to be with him instead of his brother, and why you were willing to jokingly flirt with him when you wouldn’t with the other. You did have feelings for Dean – the product of late-night talks in each other’s rooms when neither of you could sleep, which was all too often, and gentle touches while patching each other up after fights, and sitting together in silence when one of you was breaking down, and fiercely protecting each other, and years of sweethearts and beautifuls and that’s my girl’s – and the idea of holding his hand or saying cute things to each other made you nervous, like a little girl who desperately wanted to keep her feelings secret. Which you did, really. Unrequited feelings, you could handle. Awkwardness, you could not.

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Young and In Love

Written for: SPN HWC - Week 13

Prompt: “You’re an idiot. I’ve met smarter sandwiches.” & Love by Lana Del Rey

Words: 2553 (lyrics included)

Pairing: Dean x Reader

Warnings: Smut, Fluff, College AU

A/N: So for week thirteen I really like both prompts and I also love college AUs so here you go. I sincerely hope you enjoy. All errors are my own, gifs found on the google, and feedback is greatly appreciated. Thank you for reading!

Summary: Tagging along with your friend Jess to a college bar seems like a waste of time until you meet the older brother of Jess’ crush, Sam Winchester. As first it’s lust at first sight but after a tricked double date and a little karaoke something more seems to be brewing with you and Dean Winchester.


     Friday night in a college bar was not exactly how you planned to spend your evening, but your roommate Jess insisted. She had a crush on a boy in one of her classes and he was supposed to be there with his friends. Since your other friend Charlie was working you decided to bite the bullet and accompany her. However, since walking in you had this sudden urge to get the hell out. It was loud, crowded, and the overwhelming stench of too much Axe body spray was enough to put you off. Not Jess though.

     “Come on Y/N,” Jess grabs your hand pulling you through the crowd. “Hi Sam, we made it!”

     Jess was practically bouncing on her heels when Sam turned his smile widening at the sight of Jess. It relieved you a bit that what Jess was feeling was obviously not one-sided. “Jess, you guys got here just in time. We ordered a round. Um, I’m Sam by the way you must be Y/N.”

      You took his hand offering your own smile, “That’s me I’m the bestie you have to impress.”

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AMBROLLINS Appreciation Week - Favorite Headcanon.

I like to think that Seth is the much more dominant of the two. He knows Dean needs him and that gives him power.

Dean is VERY needy. He’s damaged due to his past of being neglected and hurt so he latches on to any attention he can get.

Seth makes Dean weak because he sees through the strong, stubborn, “crazy”, leather jacket-wearing act that he constantly puts on.

He knows Dean is an emotional wreck deep down and knowing that, it makes Dean vulnerable.

Seth would never admit it, probably because of his excessive amount of pride (just like Dean), but Dean does make him weak as well.

Dean was unique, a rare find for Seth. He was a splash of color in a black and white world and it amused and intrigued Seth. And Seth enjoyed playing around with Dean, testing his boundaries with him. He loves holding Dean and listening to Deans late night confessions about how Seth made him feel.

Dean loves bottoming in bed and Seth loves teasing Dean, knowing how submissive he can get.

Dean was an open book after all, wore his heart on his sleeve, but no one really saw and understood the scars underneath. No one understood pain like Seth, no one understood insecurity like Seth.

Dean doesn’t care what anyone thinks of him, but with Seth. Dean wanted to hear everything, he WANTED Seth to like him, he WANTED Seth to want him. He was desperate and thirsty for Seths attention, for Seths touch, for his love.

They’re very similar in the aspect that they’re both very passionate and their intensity can sometimes blind them.

But they have their differences. Seth longs for success while Dean craves love.

When they fade away from each other, fate ALWAYS brings them together, everything returns back to just them. Everything Seth and Dean do has a hint of each other in them. They were meant to be.

Two twisted souls that always find a way back to each other.


Character(s): Dean Winchester

Warning: None

Word Count: 1,175


           Late at night is the time you feel the best, and sometimes Dean can’t sleep, so your relationship works out nicely. You talk or do something quiet until the Winchester finally starts to feel like sleep is a possibility, and you join him when you decide to sleep as well.

           Tonight he went out on a supply run by himself, leaving you and his overtired brother in the second story motel room. Just as you begin to wonder when he’s going to come back, something small makes a plink noise as it strikes the window. The first one you ignore, but when the ‘plinks’ continue, you get curious and get up to investigate. One last plink hits the window as you open the sliding, screen-less frame and stick your head out. Old habits make you look down at the parking lot below.

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Excuse me while my brain just...

…can’t shut off and instead drops a gallon of DeanCas feels over my overtired sleepy head at 12.30 at night and gives me this (and with that proves I should be fucking asleep already):

Cas: “Dean, I can fix that.”
Dean: “Cas, it’s not broken.”

Because in the end that’s what it comes down to, isn’t it? They fuck up in epic, cosmic proportions, they hurt one another, their connections gets spun thin, they are pulled apart by fate, by life, by heaven, hell and purgatory and everything in between and yet they find their way back to one another. And what they have is complicated, it’s painful and even if some stuff is damaged and was not fixed yet, it sure as hell was never completely broken either.

Restless nights - Dean imagine

Request - “I’ve been feeling pretty down lately and i love your writing and i was wondering if i can get a cute and fluffy dean imagine? the reader and dean arent dating but they both cant sleep so they sit on the bed together talking and having some banter but its a little fluffy and when they wake up they’re in bed together cuddling and its all fluffy :3 you can decide the ending, thanks hon”


Your name: submit What is this?

You groaned in annoyance as you turned to face your digital clock, the red numbers glowing in the dark read, 02:15 am. Another sleepless night yet again, these were becoming more frequent and needless to say, you were tired of it. You and the Winchesters had the day off tomorrow, so when you finally did fall asleep, you could catch up on a few hours.

You dragged yourself out of bed, wearing some pink pyjama bottoms and your favourite Led Zeppelin shirt, and made your way towards the library to find yourself a new book to read.

You heard faint sounds; one of the brothers was up and watching something. The closer you got to the library, the clearer the sounds became. The volume was on low but you could faintly hear moans. ‘OH MY GOD! They’re watching porn!’

You quietly tip toed down the corridor and peaked around the corner, only to see Dean sat at the table nodding and biting his lip to what was on the screen.

“What do you think you’re doing, young man?” You spun around the corner, your voice mimicking a strict school teacher.

Dean quickly slammed the laptop shut, his face turning red. “N-nothing.”

“Oh c’mon Dean, I know you were watching porn. You can’t sleep either?” You couldn’t help but start laughing at how embarrassed he was - a first for Dean Winchester.

“I haven’t been able to sleep for a while. I was bored, and that was the only thing I could think to do.” He pointed to the laptop, standing up and walking towards the kitchen. “You want a beer?”


He handed you an ice cold beer and you took a sip. “Yeah, I was bored too. I thought everyone would be asleep.”

“Well, I’m awake and I doubt I’ll be sleeping anytime soon. You wanna come to my room?”

You and Dean were best friends; he was the only person you felt closest to. You had everything in common, so him asking you to come to his room didn’t seem like a weird offer.

“Sure, don’t try anything either, Winchester.” You said in a mocking tone.

“Aw man, really? The ladies can’t resist though.” He chuckled with a wink and you rolled your eyes at him, following to his room.

You both got comfortable on the bed, Dean sitting up against the head board and you sat near the end of the bed, your legs crossed so you were facing Dean.

“So, where did you get that shirt from? You wear it all the time.” Dean pointed to your Led Zeppelin shirt, the odd rip and hole showing you’ve had it for a while.

“January 12th, 1995. Led Zeppelin played a show when they were put in the Rock and Roll Hall of Fame and my dad took me to see them. Steve Tyler was there to, it was the last thing I ever did with my dad and he bought me this shirt when we were there. I’m surprised it still fits.”

“No fucking way, you saw Zepp live?” His jaw dropped.

“Yes fucking way, best day of my life. It was amazing. Have you been to any concerts?”

“No, it’s something I wish I could do.”

“We should go to a concert one day or a festival. It’d be nice to just, relax and get muddy.” You wiggled your eyebrows at him, causing him to laugh.

“Sounds like a plan, Robin.”

“Wait, Robin? I think you’re meant to say ‘sounds like a plan, Batman.’

“I’m Batman; I couldn’t say that if I’m Batman. C’mon, Y/N get your facts right!” He exclaimed, rolling his eyes in a joking manner.

“Alright, alright and you call me the nerd.” You gently slapped his leg which was out stretched on the bed.

“You are a nerd! You were probably the biggest nerd in high school…tell me about high school?”

You shimmied up the bed to sit next Dean. “Fine, I’ll admit I was a big nerd. I was in the AV club and on the chess team.” You shook your head at the memory, both you and Dean breaking into a fit of giggles. “What were you like in high school?”

“I got all the girls, I was a stud.” He winked at you, a smirk on his face.

“Should’ve known, nothing’s changed at all.” You returned the wink.

“Still getting ass. I bet you were a hot nerd though…”

“Are you saying I’m hot, Winchester?” A sly grin crept along your face.

“Well yeah, not as hot as me obviously, but pretty hot.”

You slapped his chest hard enough for him to say ‘ow.’ “You’re so full of yourself!” You laughed, rubbing his chest from the slap. “Ok, so tell me about your first high school crush? Don’t spare any details.”

The night when on like this, talking about anything and everything. Sharing stories no one else knew about, and before you knew it hours had past. It was past 7am and after hours of talking and moving around, you found yourself in Deans embrace.

You woke up slightly confused, only to realize you slept in Dean’s bed. Dean was lying behind you, his arms wrapped around your waist. You slowly turned yourself around, snuggling into his chest. The sudden movements making him grunt and wiggle around, warning you that he was waking up.

You expected him to freak out and push you away, but instead he stayed in the position you were both in.

You’ve known Dean for a few years and you were undoubtedly in love with him, although you would never admit it. The girls Dean would pick up at bars were the complete opposite to you, but with how you were laid right now, your stomach was aching with butterflies and you wanted nothing more than to kiss him.

You had kept your eyes closed, Dean still thinking you was asleep and he began to stroke your hair softly.

Why was he doing that? It seemed way too affectionate, nothing friends would do. You squirmed slightly, making little noises to make it seem like you just woke up.

“Morning.” You said, not moving your head away from Dean’s chest.


“You know, you can keep stroking my hair if you like.” You started tracing small shapes onto Dean’s chest, savouring this moment. It may never happen again.

Dean’s fingers brushed through your hair and his grip on you tightened, pulling you closer into his chest.

“This feels so right.” He finally spoke up after a few minutes of silence.

“What does?” Your heart started to race faster at his words, but you took a deep breath trying to brace yourself, he could mean something completely different than what was running through your mind.

“This, us, holding you. I don’t know why I waited so damn long to do something like this.” He sudden pulled you up, bringing your lips to his in a warm, chaste kiss. It took you a while to respond, you were so shocked that he was kissing you, the man you adored. Shortly, you wrapped a hand around the back of his neck, deepening the kiss, spilling all your pent up emotions into this one kiss.

You both pulled away to catch your breath, resting your head back on his chest.

“Let’s do this more often then.” You smiled into his chest, listening to the beat of his heart.

“I love you.” His voice was merely a whisper and if the room wasn’t so quiet, you wouldn’t have heard him. He didn’t expect you to hear what he said but you leaned up to plant a kiss on his lips before returning to his chest.

“I love you too.” You whispered back.


I hope this was okay, it was a little rushed but not much has been posted today so I wanted to get another imagine up

- Icarus

anonymous asked:

weecest with frottage

((YOU ARE THE BEST, ANON. This is my favorite kink to write for.))

It’s late at night when Dean feels something nudge against his hip. In the dim haze of sleep he realizes this is Sam bumping into him as a result of them sharing the same bed- John’s out on an emergency hunt leaving the two boys to their own devices just until the afternoon, he promised. So the boys decided to hell with having separate beds. Sam may be 17 and lanky and sprawls over half the bed but that’s honestly the best part about sleeping with him. Dean wakes up covered in Sam. That’s usually why they don’t share. On days they’re alone for a stretch they wake up in very compromising positions. Not that they minded but for the sake of not giving their dad a heart attack, they decided while he was around to sleep separately. 

So tonight, they figured they’d have a good head start in morning. No dad to worry about till hours after (they never slept late anyway). It was the perfect opportunity to finally sleep together after a week or two of having the chance without fear of being caught.

Dean, feeling Sam shift beside him again, goes back to sleep only to wake again with an insistent nudging sensation pressing hard into him. He also hears Sam whimpering, and when Dean looks down there’s his baby brother grinding his erection into his thigh, mouth parted in a gasp, hair messy from sleep, arms tucked under a pillow he clutches tightly. Dean’s half hard from the sight already, thigh wet from where Sam’s apparently been pressing for a while now. He shifts his thigh up, just a little, but the pressure is enough to Sam pant Dean’s name and open his eyes slowly. 

The next few moments, because it’s dark and the only thing providing light is the alarm clock flashing blue, everything seems quick and disorienting. Dean’s kissing him but Sam is biting into his mouth, licking and moaning, and then he’s climbing on top of Dean desperate for more, grabbing the back of Dean’s knees and pinning them to his chest while he rolls into him at a vicious pace. Dean is more than ok with going from 0 to 60 in literally two seconds flat but he’s dizzy now suddenly breathless as Sam whispers in his ear ‘hold onto me, need to feel you- fuck- already hard- so fucking wet-‘

If Sam was asleep before, Dean would never have known. His hips flick forward and the heat- the fucking heat and the fact that he can feel every inch of Sam through his boxers and the wetness- it all goes straight to Dean’s dick. Sam pushes hard right then, muscles straining to bury Dean in the mattress and then he holds himself there for good measure. His lips hover over Dean’s, Dean who is now whimpering and panting just shy of Sam’s smirk. He needs it, tries to buck his hips only for Sam to hold him there longer. 

“Fucking christ- Sammy- you gotta move- fuckin’ do something- I swear to god if you don’t-" 

Sam thrusts once; Dean nearly shouts. He’s so oversensitive, cock hot and demanding, pulsing, soaking himself with precome. Sam starts thrusting in earnest now, still keeping Dean pinned to the mattress which is incredible. Dean doesn’t know when Sam came to be this strong but he’s loving every second of their headboard hitting the wall, the bed groaning under their weight. With Dean looking up at Sam, dark hazel eyes, smug mouth kissing him, dragging out his top lip, and a few more hard rolls- one- two- three- Dean comes harder than he has in a long while, body shuddering, every muscle tense to the point of cramping. His yells fade out into a high whining noise as he tries to catch his breath. Warm stickiness spreads between them, dampens Sam’s sweatpants, ruins Dean’s boxers, as Sam follows not a second later, grunting loud into Dean’s shoulder, biting down, his body trembling with release and sweat as he finally collapses onto him.

They lay completely spent, their breathing a mixture of heavy panting and open mouthed kisses they press to bare shoulders and throats. It takes Dean all of his energy not to fall asleep with Sam slightly more alive on top. Their skin is slick, hot, shivering just a little as Sam presses a ‘missed you’ onto Dean’s collarbone; Dean returns the sentiment in kind by capturing Sam’s jaw in his and slowly laying it over Sam’s smiling lips.