dean x charlie

The Arrangement Masterlist

Summary: in an AU where the Winchester family owns a multi-million dollar company, Dean’s in a bit of a pinch. Grandpa Samuel is threatening to cut him off if he doesn’t straighten out and stop getting into trouble. Instead of taking some responsibility, Dean comes up with an ingenious plan: find someone to pretend to be his girlfriend. You and Dean have never gotten along, but a fake relationship seems to be beneficial to you both… 

Part 1

Part 2 -  Sam disapproves of your little arrangement, and you and Dean have you ‘first date’

Part 3 -  Dean reflects on your first date, and makes plans. The second date goes a little better, and Dean finds out how good your acting skills really are.

Part 4 -  You spend the night at Dean’s place

Part 5 -  Dean struggles to deal with the rest of the morning, and then gets an unexpected call. The two of you go on a double date with Sam and Jess.

Part 6 -   Jess informs you about Dean’s past, and Sam teases Dean. After dinner, Dean brings you home to find someone unexpected waiting for you, and helps you deal with it.

Part 7 -  Dean meets your mother, and you go dress shopping with Jess.

Part 8 -  You and Dean head out to his hometown, where you finally get to meet Mary and John. The sleeping situation causes some minor problems.

Part 9You and Dean have an interesting morning, but Sam interrupts. Later, you and Mary have a little heart to heart, and Dean says something surprising.

Part 10 - The gala finally arrives, and Dean is absolutely floored by your dress. An interaction with Samuel leaves Dean fuming, but you calm him down. Dean finally admits his feelings.

Part 11 -  Dean reflects on the evening, and the two of you have a talk

Part 12 - someone delivers some unexpected and unpleasant news, sending you running. Sam and Benny confront Dean, and the three of them go looking for you.  

Part 13you head to the only safe place you can think of. A talk with your father gives you the courage to return to work, where Dean finds you immediately. But he’s not expecting your reaction. Charlie and Cas come to the rescue. 

Part 14Dean tries to cope with your breakup, and then gets a surprise visit from Crowley. Your friends take you out to try and cheer you up, but eventually you head home alone, only to find someone waiting for you.

Part 15You have an encounter with Mark, and Dean shows up just in time. The next morning, the two of you talk things out. Sam arrives with some news.

Part 16 (conclusion) -  Dean responds to Sam’s news. The two of you pay a visit to Samuel, who lashes out. Secrets are revealed and threats are made, leaving you reeling. You and Dean discuss the future.

Epilogue - A few months after the events of part 16. Sam and Jess’s wedding, a housewarming party, and revealing conversations.

Epiloge Part 2 - The Fourth of July finds you and the Winchester clan at the lake to celebrate the holiday. Jess shares some news and Dean surprises you with an important question.

5

(The only time I shall ever quote taylor swift… well some what)
HONEY.
HE’S A DEMON DRESSED LIKE A DAYDREAM.
(Literally)

I swear my parents don’t know if I’m satanic or a religious freak.

-I have devil traps all over my room
-Wear an anti possession bracelet
-talk about how cool lucifer was
But then I:
-Can name 20 different Angels
-I could do an exorcism in less then a minute
-And can explain the relationship between Michael and lucifer with exquisite detail.

But what my parents don’t understand is I’m neither I just watch supernatural.

So...

I think some of you know that ABO Appreciation Day is coming, and I’m planning big, so… Here is my schedule to July 31st (and this doesn’t include the story I post at 3:30pm). Let me know if you want to be tagged, but I’ll only be tagging until July 20th, okay?

(The schedule is based on the Atlantic time zone.)

10 am: Alpha!Tony x Omega!Reader
11 am:  Alpha!Dean x Omega!Reader
12 pm: Omega!Bucky x Alpha!Reader
01 pm: Alpha!Sam x Omega!Reader
02 pm: Beta!Bruce x Omega!Reader
03 pm: Alpha!Benny x Beta!Reader
04 pm: Alpha!Steve x Omega!Reader
05 pm: Alpha!Balthazar x Omega!Reader
06 pm: Omega!Clint x Beta!Reader
07 pm: Alpha!John x Omega!Reader
08 pm: Beta!Vision x  Beta!Reader
09 pm: Beta!Charlie x Omega!Reader
10 pm: Alpha!Loki x Omega!Reader

The Arrangement (Part 14)

Originally posted by bringmesomepie56

Summary: Dean tries to cope with your breakup, and then gets a surprise visit from Crowley. Your friends take you out to try and cheer you up, but eventually you head home alone, only to find someone waiting for you.

Pairing: AU!Dean x Reader

Word Count: 2,500

Warnings: Language, alcohol consumption (like a lot) (this is not how to cope with feelings, friends), heartbreak, sadness, loneliness, desperation, suspense, cliff-hanger

A/N: Reminder… I love you guys a lot. Like so much. Don’t hate me, it’ll be okay!

Check out the series masterlist HERE

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Already Occupied

Request from anon for a Jax x Reader where reader is Chibs’ niece and she really likes Jax even though he’s with Tara. Includes Tig x Reader friendship too :)

Originally posted by nikitassoul

“Do you think he’ll ever see me as more than just a kid?” You sip your glass of whiskey as you sit cross legged on Tig’s bed, one of your late night chats taking place.

Tig was one, maybe the only one, who knew of your gigantic crush on Jax. You could tell your best friend anything, and he knew you too well to be able to miss your feelings for the blonde biker. But all you seemed to be to Jax was Chibs’ kid niece, young and childish.

“I don’t know, sweetheart.” Tig says honestly as he leans against the head board, his legs outstretched as he nurses his own glass. “What I do know, though, is that you’ll never get your answer unless you tell him how you feel.”

You smile warmly in response, the gesture not meeting your eyes. Sighing deeply, you shake your head, taking a gulp of the amber liquid. “No point, Tiger. He’s loved Tara all his life.”

“Maybe, but the cracks are showing baby girl, and now is your time to shine if there was ever one.” You deliberate the statement in your mind as you’ve done many times before, even though deep down, you know you’ll never tell Jax how you feel.

The door to Tig’s room gets thrown open, the action catching you off guard as you jump. Your eyes widen as you see Tara standing there, the look on her face telling you she’s heard the whole conversation.

“I fucking knew it.” she seethes, you pushing yourself to stand up, ready just incase she tries to attack. She storms towards you, your empty glass dropping onto the bed. “I’ve been trying to warn him about you for months, but he just can’t see it.”

“Are you for real right now? If there’s anyone he needs to warned about its you.” You see Tig get up out of your peripheral vision, giving you space to stand up for yourself but also ready to stop the two of you from clawing each other to pieces.

Her anger turns to humour as she laughs in your face, the cocky smile on her lips something you’re just itching to scratch off. “I’m only gonna tell you once, so listen up. Jax is mine, he loves me. You’re just a desperate, worthless bitch.”

You don’t even realise you’ve slapped her until you feel the sting on your palm, her hand flying to her cheek to cradle her reddened skin. Your eyes flicker to Tig, a proud look on his face as he winks at you.

You can’t rest for long before Tara delivers a slap of her own, you swinging a punch in return as she falls to the floor. Before you know it, you’re both on the floor, the two of you shouting in anger as you fight.

You’re too busy seeing red to notice Tig come behind you, only realising he’s there when he drags you off of Tara, Jax pulling her roughly off the floor as you both try to escape from your captors. “What the fuck is going on?!”

You stop resisting Tig as Jax shouts, a stressed and confused expression on his face as he looks between you and your opponent. You place your hand on top of Tig’s as it rests on your waist, knowing you’re going to need his support before Tara even speaks.

“She’s fucking obsessed with you, that’s what!” Tara shouts, shoving Jax away from her. You feel like you might puke as you stand there, your big secret out in the open. “I questioned her about it and she attacked me!”

“I wouldn’t say calling me a worthless bitch is questioning me, but whatever floats your boat.” you spit sarcastically, ignoring Jax’s burning gaze. She lunges for you again, your clenching fist unneeded as Jax grabs her swiftly, yanking her backwards.

“Out, now!” he orders, leaving no room for refusal. Tara stares at him in shock, unable to comprehend that he’s talking to her. She scoffs, shrugging his grip on her away.

“Fuck you, Jax. I’m too good for this shit.” You look down at your feet at her words, feeling guilty for being partly to blame for their argument.

“Give us a minute, Tig.” You swallow nervously at Jax’s request, Tig removing himself from you. He looks at you for reassurance, not wanting to leave unless you’re okay with it. “I’m not mad, (Y/N).”

Relief floods you, your attention flickering to Jax’s pleading eyes before you nod at Tig, squeezing his arm as thanks before he leaves the room, shutting the door behind him.

“Is it true?” Jax asks, breaking the tense silence. You stare at your feet as you nod in confirmation, a sigh leaving Jax’s lips. You watch as he sits on the edge of the bed, his hands running over his face as he tries to take in the new found information.

You shuffle on your feet awkwardly as he stares at the wall, brow furrowed as he thinks deeply. He shuffles over, tapping the space next to him, you complying as you shuffle over and sit down.

“Why didn’t you tell me?” You roll your eyes, chuckling humourlessly as you pick a loose thread on your jeans.

“What would’ve been the point?” you ask quietly, not being able to look at Jax as he sits so closely, his eyes watching you as he waits for you to continue. “All I am to you is Chibs’ niece. Plus, you have Tara.”

“Had. I had Tara. I ended it just before you went all Jackie Chan.” he teases, nudging your body with his. You smile, shaking your head as you nudge him back, enjoying the closeness.

“I hope you’re not expecting me to say that I’m sorry to hear that. No offence but I kinda hate her.” Jax laughs at your honesty, his sparkling eyes meeting yours, your lungs feeling empty at the little distance between the two of you.

You force yourself to be realistic, smiling sadly at the biker. “Don’t worry, you can save the whole ‘I wanna be friends’ speech. I wasn’t expecting you to return my feelings.”

You stand up quickly, walking over to Tig’s chair and retrieving your jacket, tears prickling at your eyes as you try to resist breaking down. “I should be going anyway.”

You spin around, your eyes wide in shock as you see Jax lean down, his hands grabbing your face as he kisses you. You don’t respond at first, not sure whether you’re dreaming, until you realise this is real life and oh my god Jax Teller is kissing you.

You let your eyes flutter shut as you kiss him back, his lips feeling nothing short of incredible as they move against your own. Your jacket is forgotten as you drop it to the floor, your hands moving to grip his biceps as his tongue slips into your mouth, your core tingling at the feeling.

Only when you’re completely breathless do you pull away, Jax resting his forehead against yours as the two of you struggle to breathe. You grip his shirt between your fingers, not wanting him to move and ruin the moment.

“We should do that more often.” you say, Jax smirking before he places his lips to your forehead, his arms wrapping around you as he hugs you.

“Sorry it took me so long.”

A/N - Wasn’t sure how I wanted to go about this but I’m pretty happy with how it came out!!! Thanks for reading, feedback is always appreciated ❤

4

Sam: Hey, Charlie did you know that Dean likes YN?

Dean: God! Don’t say that out loud! What if she hears you?

Charlie: She’d be extremely happy to hear that

Oops

Based off the song Oops by Little Mix feat. Charlie Puth

Word Count: 568

Warnings: Implied smut kinda. Fluff

A/N: This kinda turned into one of those drabbles where I didn’t actually define the pairing. So you can decide who you want this to be with. Dean, Sam, Cas, someone from another fandom, whoever you’re crushing on at the moment… All I know is that this song is absolutely adorable!!

Version en Español: Oops


Y/N and I are just friends.

Yeah. Friends.

That’s it. We tried the dating thing and both decided that we were better off as friends.

So yeah. Friends.

Then why do I keep waking up in her bed?

But we’re still just friends.

You know, the kind of friends who sometimes, maybe, every once in a while, no big deal, might backslide.

Keep reading

The Arrangement (Part 13)

Originally posted by yaelstiel

Summary: you head to the only safe place you can think of. A talk with your father gives you the courage to return to work, where Dean finds you immediately. But he’s not expecting your reaction. Charlie and Cas come to the rescue.

Pairing: AU!Dean x Reader

Word Count: 2,900

Warnings: Language, ANGST, general sadness, betrayal…

A/N: Bad to worse, kiddos. Buckle in for some serious angst. Please don’t hate me. I promise I’ll make it up to you…

Check out the Series Masterlist

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Sam Winchester Masterlist

Sam Winchester;

Cold heart- Reader is really confused when Sam starts acting distant and cold towards the reader.

Moose’s rugrat- Sam finds out he has a daughter.

Moose’s Rugrat Part 2-Sam finds out he has a daughter.

Goofy- Sam’s concerned for his girlfriend.

Miss-Reader gets a nervous stutter when she’s interviewed by Sam.

Family hurts- Sam is worried about the reader getting hurt when her father makes a promise Sam knows he wont keep.

Just a little blood- Sam comforts his gf when she has to get a shot.

Not the same- Sam’s gf comes back from a hunt but she’s hiding something from him.

Frozen plaid-Reader falls into an ice lake.

Broken wings- Angel!reader is scared to show Sam her broken wings.

Blood of a virgin- Reader gets attacked for her blood, Sam defends her.

The rules of dating Sam Winchester-Reader can’t seem to function without Sam.

Doll faces-Winchester brothers babysit the reader and their sister, only Sam can see the reader isn’t how a child should be.

Doll faces part 2-Winchester brothers babysit the reader and their sister, only Sam can see the reader isn’t how a child should be.

Doll faces Part 3-Winchester brothers  babysit the reader and their sister, only Sam can see the reader isn’t how a child should be.

Doll faces part 4-Winchester brothers  babysit the reader and their sister, only Sam can see the reader isn’t how a child should be.

The hands of a loved one-The reader knows she’s going to die soon but she didn’t expect it to be by the hands of her boyfriend.

stop hiding-Reader loves Sam but is too insecure to let him touch her.

Stop hiding part 2-Reader loves Sam but is too insecure to let him touch her.

Words-Sam writes a love letter to the reader

Not all stories have a happy ending-Sam left the reader to hunt with his brother back in college, only the reader went to hell after being kidnapped.

Not all stories have a happy ending Part 2-Sam left the reader to hunt with his brother back in college, only the reader went to hell after being kidnapped.

not all stories have a happy ending Part 3-Sam left the reader to hunt with his brother back in college, only the reader went to hell after being kidnapped.

Imperfections-Moments where the reader has done something that would be counted as embarrassing, but Sam finds it adorable.

Kill Sam Winchester-Sam sacrifices the reader in hope to get Dean back but ends badly when the reader comes back.

You lost me-Sam tries to get the reader back after cheating with Ruby.

Wedding from hell-Sam marries Becky, he leaves the reader but when he finally is out of the spell it’s to late.

Wedding from hell Part 2-Sam marries Becky, he leaves the reader but when he finally is out of the spell it’s to late.

Wedding from hell part 3-Sam marries Becky, he leaves the reader but when he finally is out of the spell it’s to late.

To share the Devils blood-Sam meets the Devils sister.

Heartbeat-Sam’s girlfriend (reader) can only sleep when her head is on Sam’s chest but on the left side. He notices she always does it.

Normal couple things?-Sam takes the reader on a date.

Accents-Sam adores the readers Irish accent.

Winchesters don’t do tents-Sam and the reader go camping.

Best friend’s sister-Sam finds himself attracted to Castiels’ sister.

Revenge-Charlie’s sister takes revenge on Sam after Charlie’s death.

Trouble in tattoo’s-The boys bump into another hunter at Bobbys, but this time Sam is the one who takes an interest to the cheeky hunter.

Trouble in tattoo’s Part 2-The boys bump into another hunter at Bobbys, but this time Sam is the one who takes an interest to the cheeky hunter.

Trouble in tattoo’s Part 3-The boys bump into another hunter at Bobbys, but this time Sam is the one who takes an interest to the cheeky hunter.

Trouble in tattoo’s Part 4-The boys bump into another hunter at Bobbys, but this time Sam is the one who takes an interest to the cheeky hunter.

Trouble in tattoo’s Part 5-The boys bump into another hunter at Bobbys, but this time Sam is the one who takes an interest to the cheeky hunter.

Just a child-Sam’s daughter has been hiding something from him.

Just a child part 2-Sam’s daughter has been hiding something from him

Angel code-Reader is dating Sam. She kisses him while Gadreel is possessing his body. Then, Gadreel starts to slowly fall in love with the reader.

Attached-Sam goes to Bobby’s house who is currently looking after a little girl who had lost her parents and gets attached to Sam.

Attached Part 2-Sam goes to Bobby’s house who is currently looking after a little girl who had lost her parents and gets attached to Sam.

Attached Part 3-Sam goes to Bobby’s house who is currently looking after a little girl who had lost her parents and gets attached to Sam.

A thing for Winchesters-Dean and the reader slept together before she dated Sam and she gets possessed by a demon and the demon tells Sam about it

Karma- Reader can’t cope when she finds Sam asleep in bed with Ruby.

Happy Birthday- Sam give the reader a surprise on her birthday.

Doll faces-Winchester brothers owe a friend a favour and babysit the reader and their sister, only that Sam can see the reader isn’t how a child such be.

The coffee shop girl- Sam is awe struck by the girl he see’s in the coffee shop but she turns out to be insecure and shy.

Mixed up love- Sam likes the reader and asks her friend to help him practice asking her out, reader mishears and thinks Sam loves her.

Where are the muffins- Reader and Sam cooking dinner for Dean and Cas in the kitchen.

In another life-Sam and Dean get sent into the ‘real world’ Sam find out’s that his wife is Ruby, but that’s not all he finds out. (Daddy Sam)

In another life Part 2- Sam finds the reader in his world. (Daddy Sam)

People change-Sam realises the innocent girl in college is now cold hearted.

People change part 2-Sam tries to get reader to stay with him and Dean.

Baby on board-Sam oneshot where the reader gets turned into a baby.

Smother-Reader refuses to let Sam love her.

Scars-Reader is insecure and Sam coax’s her into showing him her true emotions that she’s buried all these years. 

In every situation-Sam helps the reader on her period

Suicide-Reader pushes everyone away but Sam’s determined to stay

Beastly-the reader was born with a strange face and hides her face from everyone accepting she’ll always be alone until Sam Winchester turns up.

Here for you-Sam helps the reader when she has a panic attack.

Till death do us part-Sam’s wedding night with his virgin wife!

Daydreamin’-Reader see’s Sam ‘Agent Smith’ and immediately develops a crush

Daydreamin’ Part 2- Sam finds out the reader he saved is now a hunter.

Perfect for me-Reader is shorter than Sam and he finds it adorable.

Speak now-Reader is in love with Sam but she finds out he’s getting married.(Not the Becky episode)

Smitten-On a hunt Sam gets hit by a love spell which makes him fall for the first person he see’s.

To build a bridge-Reader is in love with Sam so when their on a hunt they each have to reveal a secret.

Let me show you-Sam and the reader are dating but the reader always feels to insecure. 

Shy Lovin-Reader is Sam’s girlfriend, who’s very shy.

Imagine being Dean's daughter and starting your period.

Being the only girl in a group of three men was not the ideal situation for a teenage girl. With so many changes going on in a teenagers life, having another female around was better for everyone, especially the teenager. She would have someone to talk to, ask questions, receive advice, and most importantly guidance. You, though, had to accept all of those things from three adult men who were terribly awkward around females to begin with.

Sam was the only one that wasn’t so awkward you could cringe. He used google and sent it through text message so you could read it while you were alone. Believing it was science and knowledge based helped through the uneasiness, but god, the pain in his eyes while looking at female anatomy was enough to make to the atmosphere around him turn sour.

Dean was the second worst, nearly tied with Castiel, even though he was your father. The mention of puberty and Dean was pale and sweaty. All that he wanted to do was change the subject as soon as possible, so he was never any help. And poor Cas was the worst. His knowledge of teenagers was so small that he didn’t even understand the change in hormones.

So, when you decided to stand up one early morning after breakfast for another delicious plate a pancakes, fear laced the little nerdy angel as well as the Winchester brothers. There on the back of your jeans was a small stain of blood.

“Holy shit, Y/n,” your father cursed standing up. “What happened?”

“What? What do you mean?” The paper plate bent as you flopped in two more pancakes.

“You’re bleeding!”

“What? Where?”

“T-The back of your pants…”

Warmth covered your hand as you felt around to find the wet spot. Eyes wide and heart pounding, tears began to fill your eyes. “W-What the- Dad! What’s happening!” He froze and looked over to his brother. “Uncle Sam?”

“You don’t know?” he asked dryly.

“Know what!” Oh, of course you knew about the menstrual cycle, but was it supposed to be that much blood? It was freaking Niagara Falls!

“A-About…uh…you know… monthly things…end of a sentence…?”

“A period?” you asked nervously only to receive a nod as a response. Frozen in place, realization hit you. God, now what! You had no pads, tampons, or panty liners to block the red flow and your Dad and Uncle were sure as hell not taking you shopping for those products. Screw being a woman, damnit!

“Y/n, hey, where are you going?” Dean asked as you bolted to the bathroom and locked the door. “Y/n, it’s okay!”

With much practice after all these years, it wasn’t too hard to ignore your father. This trait developed after all the times he freaked over stupid events, not to mention all the times he called your name to tell you to start cleaning. Honestly, it came in handy more often than not.

Shaking hands made it hard to call the only close female you knew, Charlie. Luckily, though, she answered on the second ring. “Y/n! What’s up?” Silence. That was all that filled the room. “Y/n, is something wrong? Where is your dad? Come on, answer me!”

“I-I…I-I started my period…”

“That’s what this is about…?” the redhead asked gently. “Babe! This is normal! You’re a girl! A teenage girl!”

“I know, but I don’t know what to do! Dad is freaking and Sammy is trying to explain it and-” A groan interrupted your train of thought and flow of words. Why the hell was she so excited? This shit hurt! Hot flashes, mood swings, cravings, and the constant fear of leaking was thrown at you without a single warning. Mother nature threw a curve ball your way yelling, “Watch out” when it was too late. Smack. Straight in the face.

“Just stay calm,” she giggled. “I’m on my way.”

“Thank you….oh…and one more thing.”

“Yes?”

“Bring ice-cream.”



Requested by: @mrsackles101

2

Truth or Dare, Princess

Summary: When the boys are stumped on a case he sends them to the reader. That one case leads to a more permanent relationship with the boys, and ultimately her falling in love with Dean…and Cas. There’s always been something about the reader they’ve loved and a game of truth or dare let’s them explore it. 

Word Count: 4816

Author’s note: SMUT SMUT SMUT!!!! I absolutely LOVE this one guys!! Just as a warning the plot doesn’t 100% follow along with the shows plot. Tell me what you guys think about this one!

You’d been hunting with Sam and Dean for the past year, your paths crossed on Arachne case. Bobby had referred the boys to you, you weren’t a hunter but you focused on lore. After telling Bobby how confused they were he sent them your way, but you never knew how important that one small decision would be.

Bobby had set it up so the boys would meet you at the library you worked at, it was a cover for you. The first and second floors were all normal books, but the basement was specifically for lore and hunters. You had hunters file in and out, and you helped them the best you could.

When Bobby had first suggested you to the boys Dean smirked, “She seems like just your type Sammy, nerdy”. Bobby just smiled to himself about Dean’s comment, he knew the second Dean saw you he’d be sold. Sure you were smart and loved books, but you were also incredibly beautiful.

Sam rolled his eyes, “Dean you of all people should know not to judge someone off of what’s said about them”. Bobby continued telling the boys where they could find you, and how he’d set up the meeting. The boys were in need of help so they didn’t mind. Bobby placed a call to you and then the boys were on their way.

It was closing time, which meant it was just you. You were excited but nervous, Sam and Dean Winchester were legends. Before you knew it you hear the sound of a bell, and eventually two men walked in. Taking in their descriptions you knew it was Sam and Dean.

They made their way over to the counter, and the closer they got the more you realized how incredibly good looking they were. Dean leaned against the counter, “Hey princess, you must be (y/n)”. You felt your cheeks begin to redden, “Yes I am, and you must be Dean”. Hearing him call you princess set butterflies a flight in your stomach.

He grinned, but before he could reply his brother cut him off, “ Thank you so much for even helping us, so is this whole library yours?”. Dean rolled his eyes, his brother was cockblocking him. You smiled realizing how beautiful Sam was too, “Yes…kinda…my aunt left it to me when she passed”.

You had always been close with your Aunt, and she was a hunter. She’d be good friends with Bobby and she was the reason you were even in this lifestyle. Sam forced a smile feeling bad for bringing up something so emotional, “I’m sorry, losing someone is one of the worst things to go through”.

Placing a stray piece of hair behind your ear you replied, “It is, but it’s good to have this place. It reminds me of her and hunters always come in telling me stories. I mean we all know death is never really the end..but enough about me how can I help you guys?”. Sam tried not to laugh but he found you incredibly cute, especially how you babbled on.

Dean licked his lips, he had about a thousand different ideas about how you could help him, “We’re having trouble figuring out what exactly we’re hunting”. You smiled, “Well I think I can help, follow me”. You started to lead them down to the basement while Dean let his eyes roll to the back of his head mouthing, “Oh my god” to his brother.

Sam shook his head in annoyance, he believed there was a lot more to you and didn’t want you to become one of his brothers flings. When you finally got into the room you pulled out your laptop and set it on the main table, “Okay what can you give me?”.

Dean raised his eyebrows, knowing exactly what he could give you but once again Sam intervened, “One of the witnesses said the creature had mottled skin and double sided irises”. You knew exactly what it was, but you were sad things were over so easily. Both brothers pulled a chair up next to you and you felt flushed being in the middle of such an attractive sandwich, especially with the way Dean was looking at you.

You pulled up the file, “I think what you have is an Arachne I know they’re only-”. Sam chimed in, “located in Greece”. Dean wanted to throw up, it had been five seconds and you were already finishing each other’s sentences. He placed his hand briefly on your knee sending shivers down your spine, “So how do we gank the son of a bitch?”.

You bit your lip trying to stop your mind from where it was going. You hoped Dean hadn’t noticed but he did, and he grinned realizing his effect on you. Turning to him you explained, “Decapitation is the only way they can be killed, and Sam I think ever since the apocalypse creatures have started appearing…it’s strange but-”.

Sam laughed, “Strange has become a regular adjective to describe our life”. Sam was amazed, it took you about a minute to know what the monster was and only with a few details. You got up, “I guess that solves things, I hope I was worth it”.

Dean got up too, “Oh trust me, you were so worth it”. You blushed again, obviously picking up on what Dean really meant. Sam added, “It was incredible how quickly you knew what we were hunting, thank you so much”.

Dean grinned, “You know we should get your number for future cases, you’re a lot easier to look at than Bobby” he finished his sentence with a wink. You laughed, “I don’t know Bobby does have this vibe to him…”.

Both brothers laughed but you finally said, “ I’d love to hear how the case goes, and I’d love to help out again”. You leaned down to write your number on a piece of paper and Dean raised his eyebrows to his brother again, signaling how good at this game he was.

That case started the relationship you had with the Winchesters. They called you to tell you how the case went, and then to ask for help on the next one, and then the next. Finally after a couple months you decided it would be easier to move into the bunker.

Bobby found someone to take over the library for you, a friend of his named Garth. You were happy to move in the Winchesters, the library had become the only family you’d had but at the end of the day it was just a building. It was a place filled with memories, but none that truly belonged to you.

Sam had become a close friend, while Dean had become somewhat of a love interest. Which meant; you were hopelessly in love with him but you weren’t sure how he felt. He flirted with you, but you never took it seriously because you soon learned Dean flirted with everyone.

On some cases you worked with their friend Charlie, she was similar to you. She loved fictional worlds, and shared your nerdy tendencies. A friendship soon formed, and you were thankful to not always be the only girl in the house. You told her everything, especially your feelings for Dean.

There was one other person you became close with, Castiel. You were working on a case about angels and Sam called him in to help you. From the moment you saw those piercing blue eyes you were sold, your heart confused at what you felt for both him and Dean. You justified what you felt with the fact that you didn’t even know how Dean felt.

You still remembered the first time you’d met him. You were in the library all alone when he walked in, a determined look on his face. His voice was low, “You must be (y/n) from Dean’s description but you don’t look hot you look of normal temperature for a human”. You laughed instantly, so this is what angels were like.

You stood up, “I’m guessing you’re Castiel-”. You lost your train of thought when you looked into his eyes, mesmerized by their intensity. Finally you caught yourself, “I’m sorry I’ve never met an angel before I-”. He smiled, “It’s okay, I haven’t met a human like you before” he said looking you up and down.

With the pressure of his gaze you felt uneasy, “Would you like to get started, I think we might be dealing with an archangel but I’m not sure”. Castiel sat down next to you and you couldn’t help but think about how close his body was to yours. Your mind started to drift so you tried to pull yourself back, but out of the corner of your eye you saw Castiel smirk.

You needed to bring your mind back, “What does this look like to you?”. Again Castiel grinned, but you just ignored it. He placed his arm over your chair and leaned forward looking at your computer screen, “I think your assumptions might be correct, but we need more evidence”.

You felt relieved that you knew what you were dealing with, until you realized your mind was drifting again. There was so many questions you had about angels; did they have sex or was that a sin, what can they really do with their grace, could angels even get hard?

You were too busy to notice the way Castiel was looking at you. The thing was you’d forgotten one essential thing about angels, they could read minds. Castiel heard every impure thought you’d had, and he was amused by them. On the outside you were so innocent, but he was starting to know how much your desires changed you.

This was something he could use to his advantage, you still thought he was innocent too. He rubbed your thigh lightly, “Are you okay (y/n), you seem distracted?”. You snapped out of your thoughts, but nearly went right back in when you realized how he was touching you. Trying to play it off you forced a laugh, “Yeah sorry, this has been a lot….the case”.

Castiel just smiled, you would be fun. From that moment on Castiel became very interested in you, but you never knew what he was really thinking. Could angels even flirt, could Castiel even flirt? You were in a constant whirlwind of emotions between him and Dean.

You were in the library with Charlie and Sam, obviously researching, when Dean walked in. Castiel trailed behind him, they both looked happy. Dean sat next to you, “Hey princess, what do you say we do something a little more fun?”.

Your heart started to race thinking about what fun could really mean so you missed the look Castiel gave Dean. After a second of letting you go crazy Dean added, “WE all could do something a little more fun”. Finally your heart slowed down, he was talking about everyone.

Charlie was excited, “Okay Dean what did you have in mind?”. The look that formed on Dean’s face sent shivers down your spine, he was up to something. He grinned, “We’re going to play good ole truth or dare….but sexual”.

Sam rolled his eyes, “Really Dean, what are we 16?”. You laughed at Sam’s comment, this did seem a bit juvenile. Dean put his hands up defensively, “Come on Sammy I think we’re all dying to know how innocent (y/n) really is”.

Suddenly all eyes were on you and you felt your entire face turn red. You smiled sheepishly, “Uh-”. Charlie cut you off, “ We’re in” she winked at you. You gave her a look but she didn’t care, she knew this might finally push you to do something with Dean.

Dean clapped his hands together, “Good, now who should go first…”. Again the whole room looked to you and you just shook your head. You rolled your eyes, “Okay, me I guess”. Dean looked to Castiel before looking back to you.

He grinned, “So truth or dare?”. You felt like you’d be screwed either way, “Dare”. Dean’s jaw dropped and the entire room cheered at your decision. Dean licked his lips, “I’ll start easy; I dare to tell you to tell me one of your kinks”.

Charlie started laughing and the rest of the gang became a thousand times more interested in what you were about to say. To the gang you were the innocent one, but if only they knew how you really were. You closed your eyes summoning up the courage, “Well you guys can’t judge me”. Dean had a weird look in his eyes, “I wouldn’t dream of it princess”.

Maybe it was because it was already extremely late, or the fact that you’d been thinking about Dean all day, regardless you told them the truth. For once you had the courage to let them know just how “innocent” you were.

You exhaled, “I like when people are really dominant…not just telling me what to do but just reminding me I’m yours..you know…like I better listen to….”. You decided to quit while you were ahead and you hid your face in Charlie’s shoulder. Charlie grinned, “Daddy…she was going to finish the sentence with daddy”.

You wanted to kill her, you weren’t embarrassed of what you liked it you were just shy. Dean tried to hide his excitement, he was so instantly turned on. Finally you looked up and you felt on fire between the looks Castiel and Dean were giving you.

Dean smiled, “Don’t be shy about it princess, to make things fair I’ll tell you one of mine”. You bit your lip in anticipation, there was no way to keep your thoughts pure now. He grinned, “We go hand and hand, I like being called Daddy and knowing I have a good little girl who listens to me”.

You squeezed your thighs together tried to stop the throbbing. Sam got up, “I didn’t need to hear that I’m gonna-”. Dean laughed, “Don’t act so pure Sammy we share a wall so I know what you’re up too”.

Sam looked from his brother to you and his whole face became a deep shade of red. He ran a hand through his hair, “Fine Dean, but I also don’t feel like hearing what gets you going”. Dean winked at you before saying, “Fine Sam, but I have a feeling the rest of the room is extremely interested”.

You felt yourself already getting wet, Dean was obviously talking about you. Sam rolled his eyes and excused himself. Dean didn’t skip a beat, “Alright princess, now it’s your turn to ask someone”. You decided that you wanted to ask Castiel a question. You grinned, “Castiel, truth or dare”.

Reading your thoughts Castiel knew picking truth would be a lot more entertaining, “I chose truth”. You tried not to blush, “Do angels have a sex drive or is that a sin?”. Castiel smiled, this would be so easy.

He looked to Dean and then you, “I have a sex drive, I may be an angel but I can be as sinful as I want”. Castiel looked you over while saying the second part, and the intensity of his gaze sent shivers down your spine.

Charlie spoke up, “Guys I know I don’t bat for your team but don’t bench me!”. Castiel turned to her and asked a question, “What is your favorite part of a woman?”. Charlie thought it over for a second before giggling.

She shrugged, “I’m a tits kinda girl I guess”. The boys both laughed and so did you. Somehow Charlie could make the most weirdest situations funny. She held up a finger, “I almost didn’t notice Cas but you didn’t ask me truth or dare, which makes that a clear violation. Which means you must now do what ever dare I chose”.

Cas nodded his head, he was a man of rules. Charlie giggled again, “Since you’re as sinful as you want I dare you to whisper the dirtiest sentence you can think of into (y/n)’s ear”. You jaw dropped a little, would you be able to handle that?

Castiel just nodded his head again and within a second he was next to you. With one hand he delicately moved your face towards him, and trailed the other up your thigh. You closed your eyes and felt his lips graze your ear, “I want you to be a good little girl for me and let Dean fuck that pretty little pussy of yours while you suck my cock”.

You bit your lip hiding a moan, you wanted so badly to say, “Yes daddy” but you remembered where you were. To your surprise after he was done speaking he kissed you below your jaw. Charlie and Dean were going wild.

Just like that he returned to his seat, leaving you wanting more. Charlie raised her eyebrows, “From how (y/n) is reacting I guess you weren’t lying”. Feeling all eyes on you, you were eager to divert the attention. You looked to Dean, “Truth or dare?”.

He leaned forward, “Dare princess”. You gulped, unsure of what to ask. You wanted to dare Dean to take you right there on the table, but you needed to control yourself. Smiling you said, “I dare you to tell me why you keep calling me princess”.

You figured that would be an easy question and that maybe the throbbing and desire you felt would stop, but you were wrong. He licked his lips, “I like how worked up it gets you, from the first time I called you it I saw what it did to you”.

You felt yourself beginning to blush again, unsure of what to say. Suddenly Charlie got a text and her entire demeanor changed. She sighed, “The bat signal has gone off guys, looks like my night is done”. You were sad that Charlie had to leave, and nervous that you’d be left with the boys.

She hugged you and everyone gave their goodbyes. Getting up you said, “Well that’s my night too, sorry to disappoint boys”. Dean looked up at you smiling, “You never disappoint princess”. You found yourself smiling but before you could walk out Castiel got up.

He reached out a hand, “The least we could do is walk you to your room”. That would be nice, and it seemed innocent enough so you agreed. They got up and gave each other weird looks, which made you rethink your decision.

Pushing it to the back of your mind you continued walking forward. It was a short walk to your room and before you knew it you were there. You opened the door and they both leaned on either side of the frame, “Well thanks guys, I guess I should go to bed”.

The truth was that you didn’t want to go to bed, you wanted the both of them like Castiel had suggested. You were too shy to act on it so for right now it just occupied your thoughts. They looked to each other and Castiel spoke up, “Your mind suggests otherwise (y/n)”.

You were confused, “My mind?”. They grinned now, a look of satisfaction on their faces. Castiel explained, “You’re a very intelligent girl (y/n), but you’ve been incorrect about the most fun part of being an angel; reading minds”.

There was no hiding it, your face turned bright red. You tried to remember everything you’d been thinking about, especially the dirtier stuff. Castiel laughed, “Yes, I’ve heard everything…you’re a dirty little thing”.

Now Dean chimed in, “I can’t believe I thought you were so innocent, I think it’s time we treat you like the dirty girl you are”. Your mouth just opened as you felt your desire growing, unable to respond.

Castiel got closer to you and again lifted your chin up with a finger, “Be a good girl and answer us”. Somehow you found the words and said, “Yes Castiel”. He turned to Dean smiling, everything was falling into place. They followed you into your room as Dean closed the door behind you.

Castiel added, “I want you to call me commander, think you can do that baby?”. You nodded your head but remembered what they wanted, “Yes commander”. Dean grinned, “Look how quickly she catches on, this will be fun”.

You just gulped, waiting to see what their next move would be. Castiel shook his head, “I can still read your thoughts (y/n), so eager”. Biting your lip you still waited to see what they’d tell you.

Dean looked you up and down, “I think I wanna play with her for a little while you watch, is that something you’d like princess?”. Your breathing became more rapid, “Yes daddy”. Dean lead you towards the bed, your back against the headboard.

He bit his lip, “Let’s get you out of those clothes”. You started to lift the dress you’d been wearing, leaving you in just your baby blue bra and panties set. Dean groaned, “Fuck Cas, look at how beautiful she is”.

By now Castiel had sat in your desk chair, lightly palming himself through his jeans, “Breathtaking…”. You felt yourself getting wetter with all the attention and anticipation. Dean turned your head towards his, “I’ve wanted to do this since the first day we met”.

He lightly placed his lips on yours while his hand cupped your cheek. The kiss ignited a flame of desire in your core, you wanted more. When it was over he slowly dragged down your bottom lip with his thumb, “Fuck you’re amazing”.

You were so needy, “Dean..I-”. He shook his head and brought his hand to lightly grasp your throat, “Daddy”. It made your breath hitch and your core soaked. You blinked, “Daddy, I need more”. He removed his hand and kissed your forehead, “Good girl”.

His hand trailed down your stomach and slipped under your panties, he slowly inserted one finger inside of you and you moaned. Dean took his finger out and sucked on it, “You taste so good princess”. You watched him with your mouth wide open, so turned on.

Dean moved down the bed, bringing himself closer to your core. He slowly took off your panties, “No need for these doll”. After that he spread your legs and you bit your finger unsure of his next move. He licked his lips, “So fucking beautiful princess”.

His praises were turning you on even more. Dean licked up your folds and you moaned at his touch. He flicked his tongue lightly over your clit, sending shivers down your spine. Looking to your left you saw Castiel was now fully exposed, stroking his shaft.

Seeing Castiel made you even more needy, he looked so good. Dean spread your folds with his two fingers, exposing you further. He started to trace patterns over your clit with his tongue, “Fuck daddy that feels so good”. Castiel groaned, becoming more turned on too.

You bucked your hips, needing more, but with his hands Dean held you down. You loved the feeling of having no control, your pleasure all up to Dean. He moved his head faster and you felt yourself getting closer, “Daddy please I’m-”.

Dean stopped what he was doing, “I know princess, but I want to feel you cum around my cock”. He moved back up next to you and called over Castiel. You felt the bed sink down as Castiel sat next to you.

He placed a stray strand of hair behind your ear, “You look so beautiful when you’re so worked up”. Before you could reply he crashed his lips into yours, his dominance surprising you. Castiel knew what he wanted and didn’t hesitate to take in.

During the kiss Castiel shifted your body, bringing you ontop of him. Dean now kneeled behind you, and brought your ass to press against him. Once the kiss was over Castiel said, “I want to see those pretty lips wrapped around your commanders cock”.

You nodded, “Yes commander”. Dean groaned, “She’s such a good little girl”. Getting on all fours your ass pressed against Dean and your lips hovered over Castiel’s cock. You licked slowly up Castiel’s shaft, swirling your tongue around his tip causing him to moan.

You felt Dean’s tip press against your pussy, “Please daddy”. He slapped your ass, “Not until you start to suck his cock”. You nodded your head and finally took Cas in your mouth. Finally when you took as much of Castiel as you could you felt Dean enter you.

You moaned against Castiel’s cock which caused him to buck his hips forward. Dean started to enter in and out of you, stretching your walls. Following his speed you started to bob your head up and down. Castiel got a fistful of your hair, pushing your head down lightly.

Cas moaned, “Fuck this feels so good”. Dean slapped your ass, “Damn straight”. You liked the slight tang of pain you felt when he slapped your ass. Dean placed his hands on your hips, thrusting himself deeper inside you. You moaned against Castiel’s cock again, “Fuck Dean, keep going..it feels so good when she moans against my cock”.

Dean went faster, “That’s it princess, you look so good with a mouthful of his cock”. You took even more of Cas in your mouth, the feeling of being completely filled so intoxicating. With your hand you started to play with his balls, making Castiel moan even more.

You knew you were getting close and Cas let Dean know, “Our good little girl wants to cum”. Both boys were just as close as you were, everything was so intense. Dean felt himself getting sloppier, “Fuck princess, I do too, cum when we tell you”.

Castiel started thrusting himself into your mouth, “You’re gonna make your commander cum all over those pretty lips”. Dean was thrusting so deeply into you he was hitting your g-spot every time. You felt like you were going to explode, and you didn’t know if you could hold on any longer.

Dean was moaning so loudly, “Shit this feels so good, doesn’t it babygirl”. Castiel was just as close, “Let’s let the good little girl cum for us Dean”. Suddenly both boys started thrusting even deeper, and you felt your senses become flooded.

Dean nearly yelled, “Cum for us princess, fucking cum for us right now, be a good girl and fucking cum”. That was all you needed, you let yourself go. Your body shut down, the only thing you could process was the pleasure.

It was like a bomb that went off in your core and shook through your entire body. All you could do was moan, but you mouth was filled. You moans sent vibrations against Castiel’s cock, and then he was cumming too. You felt his hot load shoot to the back of your throat, but you continued sucking.

Castiel moaned so loudly, “Fuck she’s still sucking…shit I’m so sensitive..fuck”. This was all enough to set Dean off too. He felt your walls clench against his dick and he thrusted even harder. The moans that filled the room caused his own orgasm.

He exploded inside of you, filling you up. You groaned as you felt him twitch inside of you. All the sensations were so intense, all you could do was moan. As he came Dean held onto your hips tighter. Finally you were left shaking, as both boys pulled out of you.

Castiel pulled you up towards him, placing a his lips on yours. You felt the bed shift again as Dean sat next to you both. When you were done kissing Castiel, Dean pulled you in for a kiss. Castiel laughed, “What about sharing Dean?”.

Dean smiled against your lips ending the kiss, “It’s just so hard when it comes to (y/n)”. Smiling aswell you finally spoke up, “ I am all for sharing”. Castiel pulled you so you were perfectly in between the both of them.

They each started to caress your body, sending shivers down your spine. Dean nibbed on your ear, “Fuck you’re so perfect”. Castiel whispered in your other year, “So incredibly perfect”. You sat there feeling the happiest you’d ever felt, in between two of the people you cared for the most.

Dean finally said it, “I love you princess, always have always will”. He kissed you again, preserving the moment with your bodies. While the kiss continued Castiel whispered in your ear, “I love you too (y/n), I didn’t know I could”.

When the kiss was over you were left panting, “I love you both so much”. They just smiled, just as content with life. They were incredibly excited for what your future together held, even for what rest of the night held.

Try to Understand (pt. 3)

Characters: Alpha!Dean Smith, Omega!Reader, Omega!Charlie, Beta!Benny

Word Count: 4575 (Not gonna bother apologizing, I like to use words)

Warnings: Language, A/B/O dynamics, mentions of sexual situations

A/N: Hi friends. So, yeah, this took me a while to get back to, but here’s the third part of my AU Alpha!Dean Smith A/B/O based on the song “Magic Man” by Heart. Once again, thanks to @dr-dean for hosting the initial challenge that started this whole story. So much gratitude to @roxy-davenport for being an awesome beta and helping me get this chapter where I wanted it!! As always, feedback and constructive criticism are welcome and appreciated! XOXO

Catch up here Part 1    Part 2    Part 4  *Reader’s thoughts are in italics.

Originally posted by dancewithmejensen


From Part 2:

“You want me?” he asks again, his fingers dancing on your skin, eyes dark and focused, lips parted as he breathes heavily waiting for your answer.

You lick your dry lips, the word coming out hoarsely, but clear nonetheless.

“Yes.”


He hums, satisfied with your response. You watch Dean’s eyes as they follow his fingers along the collar of your shirt. You stretch your neck as he drifts his fingers over the skin there, just barely tickling you and igniting a rush that makes its way down your body in a shiver. Your eyes roll back in your skull, and your head follows the movement, stretching your neck as your head tilts to the side.

His hand moves lower, his palm just brushing over your breast, grazing at the stiff peak of your nipple, making you jerk your head down as you gasp. Your body had never felt this sensitive, so amped up. He watches you respond to him, his jaw set as he focuses on his touch, a controlled hunger in his eyes. Never had you been with a man who had looked at you that way, like he could eat you alive.

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