Requested by @Person1125023
Skylar lays on her bed back at the bunker sniffling as she tries to not cry. Skylar's bottom lips quiver as her heart tightens from the loss she is currently feeling.
Three days ago, Skylar, her younger sister, and the two Winchesters went on Wendigo hunt up in northern Minnesota. You weren't that worried going into it because you knew you and your sister were good hunters almost on the same level as the legendary Winchesters you were with. The Wendigo seemed like it was taking two people per week at least that's what you can tell from the papers since that is how many people have gone missing after hiking up here. So in order to stop the supernatural creature, you guys hiked up the mountain ready for what was supposed to be an easy hunt after dealing with demons and angels for so long.
The four of them had made it up to a nice spot for the four of them to rest before in the morning their group continued to trek to where there was a cave perfect for a Wendigo to stay.
Dean finished drawing the protective circle with symbols to keep the Wendigo out while Skylar and her sister finished putting up the tent the two of them would share while Sam finished putting up Dean and his.
"Okay, I'm ready to hit the hay how about you guys?" asks Dean with a smile and a clap of his hands even though he was smiling Skylar could tell how exhausted he was from the long uphill hike
"Uh, Sam and I are going to go check around the area. Make sure there are no unaware civilians wandering around. So we will be back in a bit." says Skylar's sister even though the park rangers had stopped letting people come into the park last week and the only reason they let four of you in was because they used fake game wardens badges
Skylar's sister, who Skylar send thumbs up at discreetly knowing about her little crush on the younger Winchester which made her blush, and Sam head off into the woods both of them carrying their flamethrowers.
Dean sends Skylar a smile as he sits down right next to her.
"Well, I guess it's you and me now." says Dean patting your knee
"Yeah, I guess it is." Skylar said with a smile
A few minutes went by in a peaceful silence as the two of them wait for their younger siblings to return. Skylar though noticed as the minutes go by that Dean was having a hard time keeping his eyes open and he was obviously ready for sleep to take over.
"Dean, it's okay, you can go to bed and I can wait for the two knuckleheads to return." Skylar said breaking the silence causing the Winchester to look at her
"Thanks, Skylar, but I think I should stay up just in case you happen to fall asleep, you big sleepy head." teased Dean trying to play off the real reason he wanted to stay up which is to make sure his brother gets back eagerly and Skylar knew this
Skylar rolled her eyes jokingly before she nudges the man playful even though a smile stayed on her face.
Despite Dean's wishes to stay up, he drifted off to sleep seven minutes later. Dean ended up somehow in a position where his head was resting on the brunette's lap five minutes after he fell asleep and was leaning on Skylar. Skylar looked down at him with a soft smile finding the sleeping and peaceful looking Dean adorable.
"Pretty Skylar." mumbled Dean in his sleep making the blue-eyed girl's cheeks heat up
Like her sister, Skylar has feelings for a Winchester though instead of the large moose like one she likes the one nicknamed squirrel. Skylar can't exactly pinpoint the exact time she started to have feelings for Dean, they have been friends for a long time since they both spend a lot of time together at Uncle Bobby's as kids. Skylar and her sister joined the Winchester's side as hunting partners a while ago then moved in with at the bunker. Skylar hasn't told the Winchester about her feelings yet but she has been trying to work up the courage to do so.
An hour later, Sam and Skylar's sister had not yet returned from their little search which caused Skylar to grow worried. Though a bloody and bruised Sam emerging from the tree line obviously out of breath made Skylar's nerves only grow more.
"What happened?" asked Skylar with fear clear in her face as she stands up causing Dean to jump awake
"I'm awake. I'm awake." repeated Dean looking around before his eyes land on Sam
"What happened?" immediately asked Dean as he jumped up
"We-we got attacked. We were wrong there isn't just a Wendigo there are two. They-they got her. We were ambushed I somehow killed one of them but by the time I did the other Wendigo and her were gone." responds Sam making the color drain from Skylar's face
The group that day ended up killing the Wendigo that took Skylar's sister but the time they did it was too late, she was already gone. They held her hunter funeral the same day.
Skylar grips her pillow tightly as she still sniffles while wondering how she is going to live her life with the one person that has always been by her side and that means the most to her.
The next morning a worried Dean and Sam stand outside Skylar's bedroom door. They knew that the brunette is hurting even if they drove the ride home to the bunker yesterday in silence with her sleeping most of it.
"You think.....we should go in there?" asks Sam in a hushed tone to Dean
"I don't know...I mean how do you think she is going to grief? I mean she might just want to be alone or-" starts to answer Dean until the bedroom door opens to reveal Skylar who looks perfectly fine now no signs that something emotionally devastating happened.
"Oh, hey guys." Skylar says surprised to find the two Winchesters right outside her room
"Hey." they both say in unison
"You doing okay?" asks Sam softly looking at the blue-eyed girl with concern and sympathy the same emotions in Dean's eyes
"Yeah, I'm fine." answers Skylar with a shrug and scoots pass the two men heading down the hall
"Do you guys want pancakes for breakfast?" calls Skylar looking back at the boys who nod yes but hold confusion in their eyes
"Well, that answers that question. Skylar handles grief like you handle you do. She tries to bottle it all up and pretend everything is okay." says Sam looking down at Dean, who then rolls his eyes, before the two head towards the kitchen following after Skylar
The boys walk into the kitchen to see Skylar getting the ingredients out to make pancakes and the two boys look at each other trying to figure out what to say to the grieving girl.
"Skylar, we know you aren't okay. You just lost your sister it's alright and normal to need some time to grieve." says Dean
Skylar lets out a sigh but doesn't bother to look at the two men behind her.
"Guys, I'm fine. I knew this day would come sooner or later. We are hunters and we all know that everyone in this business dies bloody it's a matter of time. I'm just glad she got a quick death and is in some place better." Skylar says as she grabs the pancake mix and the bag of chocolate chips
The two brothers share a look not sure if they believe Skylar's statement but don't know if they should press her any farther.
"Okay, if you say you are fine then...I guess you are okay." says Sam hesitantly as Skylar finally turns to them
"Now that we have that done with, you guys want chocolate chips in your pancake or not?" Skylar questions with a forced smile
The week continued like this with Skylar pretending she is fine and the Winchesters being concerned mainly, Dean. Both boys continuously made sure to check in on the brunette to make sure if she needs someone they are right there so she was almost never alone except for at night. Dean though still though would walk by Skylar's room at night and made sure to slow down so he could make sure she was okay and not crying her eyes out. Once he was sure she was fine, he would continue on his way. Which turns out was a good idea because if he hadn't checked in on the girl tonight she would have made a very big mistake.
Dean starts walks down the hallway to do his nightly check on Skylar wearing his sleepwear. Dean starts to head down the hallway until he hears a door opening makes his movements stop.
Dean though still hides his body and peeks his head out to see a darkly dressed Skylar exiting her room and obviously is trying to be quiet as she shuts her door. Skylar looks around which is when Dean moves his head out of Skylar's view and waits a few seconds until he looks down the hall to see Skylar heading towards where the bunker's entrance is.
Where is she going? Thinks Dean confused and curious before he decided to follow after Skylar
Dean follows Skylar down the hallways staying a bit far behind her so he doesn't get caught. Once the two make it to the entrance of the bunker notices a certain object tucked under her arm that makes his heart stop.
A small silver tin is tucked under her arm giving Dean all the information he needs to know where Skylar is going.
Skylar starts to slip on her shoes on until a voice makes her freeze.
"Where are going?" calls out Dean as he leans up against the wall looking at the brunette with a raised brow
Skylar freezes and internally cusses before she turns around making sure to hide the shiny box behind her back.
"Just...just was hungry and thought I would go out and treat myself to a donut." Skylar lies but Dean pretends as if actually he believes the lie that came out of her mouth
"Then why are you hiding something behind your back?" asks Dean as he makes his way to the ocean blue-eyed girl
"Uh, I'm not." again lies Skylar taking a step away from the Winchester in an attempt to stop him seeing what is behind her back but Dean is too quick for her
Dean grabs Skylar's hand that is holding the box and moves her hand so the box is in both of their line of vision.
"Just going to get donuts, huh?" asks Dean sarcastically causing Skylar to look down
Dean takes the small box from Skylar's hands before he throws the box across the room.
"What were you thinking? You can't sell your soul Skylar." says Dean softly
Skylar's bottom lip quivers as the tears she has kept in for a week now fall down her face.
"I-I wasn't I-I guess. I just miss her so much and I just want her back." says Skylar as sobs rake through her body
Dean sighs before he pulls the girl into a tight hug with his hand stroking her hair while his heart breaks at the sound of her sobs and her sadness.
It hurt Dean to see the girl he has over the years fallen in love with seeing so heartbroken.
"I know, I know, but everything will be okay. It...it will just take some time but I'm here, I'll always be here." assures Dean softly
The rest of the night was spent with Dean holding Skylar as she cried letting out the sadness she has kept in. Dean whispering soft assuring and comforting sentences to her. The two of them ended up falling asleep together that night.
Even though Skylar felt slightly better after that night she was still grieving and Dean kept his promise of being with her through it. A few months went by and even though Skylar misses her younger sister dearly she has finally finished the grieving process and feels better than she has in months. Which is all thinks to a certain green-eyed hunter. Without the help from the Winchester Skylar doesn't know how she would have gotten through this. Dean was always there for her making sure she is okay and Skylar couldn't be more grateful for everything he has gone.
Skylar and Dean lay on the new lazy boy sectional Dean bought for his Dean cave watching a movie on their new traditional weekly movie night. This being Dean's turn to pick the movie so the two of them are currently watching a western movie. A bowl of popcorn sits in between the two of them and when Dean goes for some popcorn so does Skylar causing their hands to touch. The two adults in the room instantly blush like sixth grades before they both quickly move their hands out of the bowl. A few minutes pass by in silence before Skylar breaks it.
"Dean.." starts Skylar softly looking at the Winchester causing Dean to look at her
"Yeah." says Dean looking into Skylar's green eyes
"I just want to say thanks....you know for everything." says Skylar softly who like Dean isn't the best at showing his emotions
A smile forms on Dean's face at Skylar's words.
"Yeah, I know what you mean and it's not big deal." says Dean with a small shrug
"To me it was." says Skylar honestly placing her hand on Dean's arm
Dean looks down at her hand that rests on his arm before his other hand reaches over and takes Skylar's hand in his. Dean gives it a small squeeze as his eyes wander off to look at the tv screen in front of him.
Dean watches as the brave cowboy does something quite courageous before he decides to do something brave.
"You wanna go on a date?" blurts out Dean before he could lose this sudden burst of courageousness
"Huh." replies Skylar quite startled by the sudden question before what Dean said sunk in
"You-you aren't just asking me because of-" starts to question Skylar softly
"No, I'm not. I swear." interrupts Dean firmly with a shake of his head and Skylar could tell the man wasn't lying causing a huge smile to grow on her face
"Then sure, of course, I would." Skylar answers happily causing a grin to form on Dean's face
Excitement rushes through Dean before he jumps out of his seat pulling the brunette up with him before he promptly picks her up. Skylar squeals and laughs loudly as a certain Winchester carries her out of the room heading ready to go out on a date with the beautiful brunette.
Skylar's sister smiles as she stands next to Castiel looking at her sister and Dean from outside the small diner where she has been watching the couple for a while now.
"She looks happy." states Skylar's sister with a smile happy that her sister and Dean finally got together after years of them both pining after each other
"She does." says Castiel with a nod as he looks at the happy couple who are smiling and laughing with each other
"You ready to go back now?" asks Castiel after a few moments go by in silence
Skylar's sister thinks over his question as she looks at her sister. Castiel had been taking her on visit down to Earth and she had been there through it all. She has been there through her sister almost selling her soul and through all the grief. Skylar's sister then wasn't ready to not leave her sister and Castiel would have to drag her away but now she is ready to leave, she is ready to let go. Even though she knew that Dean could and never would replace the place Skylar has in her heart for her but she wasn't worried about her sister being alone. Worried that her sister wouldn'f have anyone there for her but now she knows she is does and that Skylar will be okay.
"I'm ready."
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Lowkey kinda proud of this one. What is your guy's favorite imagine I have written?