#deanimagine

Beau Arlen was working on a case with Jenny when he got a call from his daughters school. „Sheriff Arlen speaking“, I heard his voice answer the phone. „Yes Sheriff Arlen, here is the schools principal speaking. Its about Emily, would you be able to make it to the school. Don’t worry she isn’t hurt or anything.“ I was waiting for his answer. „Oh um yeah, sure, Ill be on my way right now.“ 

——

Shortly after that a knock could be heard on my office door „Come in“, I say and the Sheriff makes his way into my office, eyes landing on his daughter sitting in front of my desk. „Sheriff Arlen, thanks for coming on such a short notice. Please take a seat.“ I gesture towards the free chair next to Emily. „What seems to be the problem?“ He asks. I turn towards Emily with a sympathetic smile „Emily would you please tell your dad yourself?“.

Sheriff Arlen turns towards his daughter, with an expecting look on his face. Emily looked up at her dad for a moment, then nodded „I- uhm, I accidentally broke a window in class.“ She says, looking at her shoes. Sheriff Arlen looks at her. „Accidentally?“ He raised his eyebrows slightly. „How does one accidentally break a window?“ He replied. „I was throwing a ball with my friends, it was an accident!“ Emily protested. „I swear! I dient do it on purpose.“ Beau just sighed, running his hand over his face. „What am I gonna do with you?“ He asked, not expecting an answer. 

Emily huffed. „Im sorry dad. I really am, I didn’t mean to.“ She said, looking genuinely sorry. „Well, we believe you Emily, but still the window needs to be replaced“ I speak up. Beau nodded. „Right.“ He grumbled, digging through his pockets, pulling out a leather wallet. „How much?“ He looks at me expectingly. I smile at him sympathetically „The school will send you the bill, Sheriff.“

„Alright.“ He said. He then looked at his daughter. „You’re gonna be working for me all summer to make up for this.“ He said sternly. Emily groaned, her head dropping. He didn’t care, she had to learn her lesson. „You got that?“ He asked, raising his eyebrow at her.

„Yes sir.“ She grumbled. Beau nodded and then looked back up at me. Im still sitting by my desk and watch the interaction between him and his daughter. „So, we all good now?“ He inquired. „Thats all from me“ I smile at him. „Okay.“ He returned the smile, then nodded. „C´mon Em.“ 

He gestured at her and she rolled her eyes, standing up and following him out of the principals office. They went out into the parking lot, Beau walking to his truck. He unlocked it, opening the passenger door for Emily, waiting for her to get in. Emily got into the car and sat down, crossing her arms, still frowning and looking unpleased. Beau roll his eyes slightly and sat down on the drivers seat. He closed the door and looked at his daughter. „Whats with the attitude?“ „I just-„ Emily cut herself off and huffed. „It really was an accident. I dient mean for the glass to break.“ She muttered. Beau nodded. „I know, but you still broke it. You should’ve been more careful, Em.“ He said, starting the car.

„And you're still gonna make me work with you all summer, right?“ She huffed annoyedly. Beau just grinned at her and Emily knew, that yes she would have to work for it. 

Later that day, still in my pencil skirt and blouse, I was at the grocery store grabbing some vegetables. Completely focused on my choice of vegetables I didn’t notice, that Beau was also there t the grocery store, shopping for some food. He was still in his sheriffs uniform. He was looking at the fruits and vegetables, picking up a tomato and inspecting it. He looked down at the tomato and placed it in is basket. And just then, his eyes caught a hint of my form in the corner of his eye. He looked up, realizing it was me. „Oh… uh, hey.“ He said as he looked at me, a small bit of surprise in his voice. Just as surprised I look up and recognize him, I offer a soft smile. „Oh hello sheriff.“ Beaus heartbeat quickened just a little when I smiled at him. He returned the smile, nodding. „Hey, didn’t expect to see you here.“ He simply said. „Why not? Do you think a principal doesn’t need food too?“, I smirk at him. He let out a soft chuckle, smirking as well. He shook his head. „I guess I didn’t think of that.“ He replied, his emerald green eyes looking at me. 

There was an awkward silence for a moment as he looked at me. He then looked down at my shopping basket. „So, what are you buying?“ He asked, breaking the silence. „Just some stuff for dinner“ I shrugged. „Oh, what’re you making?“ He asked curiously, his glance going down to my basket again. „Veggie soup“ I smile at him. He nodded. „Sounds good.“ He said, genuine smile on his face. „I don't cook much when I’m at home. Im more of a take-out kinda guy, but I know how to cook. I just don’t have much time for it.“ He said with a casual shrug. I smile, more to myself, but I kind of think its cute how he is rambling. But I need to stop thinking so, he is still a father of a student. „So what are you buying then? Doesn't look like take-out to me.“ He chuckled softly, looking at his basket of food. „I’m just grabbing something for me and my daughter.“ He said, then added jokingly „Who is still in trouble for breaking that window.“ „Don't be so hard on her, Im sure it really was an accident. And all in all she is a good girl.“ I tell him, and its true. Emily is a good student, Im not just her principal but also her math teacher and she really is a good kid. He sighed softly and nodded. „Yeah, I know. But I still want to teach her her lesson. Thats parenting, I guess.“ I chuckle „Well, as her principal I appreciate that.“ He let out a soft chuckle, his smile widening a bit. 

He looked at my shopping basket again. „So… just cooking for yourself?“ He asked, curiously. Is he flirting with me? No im sure he isn’t. „Yes, just for myself.“ I tell him. He nodded. „No partner?“ He inquired, raising an eyebrow. I just shake my head at him, holding eye contact. He nodded again. „Why not? Someone like you should have someone.“ He said truthfully, although he didn’t mean to be so honest and blunt with me. He was just saying what he thought. „Someone like me?“ I chuckle. „Yeah.“ He said simply, his emerald green eyes looking at me. „Youre a beautiful and smart woman … You deserve somebody to love.“ I get a bit flustered. „Oh well Sheriff. Thank you very much … but its a bit more complicated than that.“ I answer honest, because it really is more complicated. Beau picked up that I got flustered, and smirked as he chuckled softly. He raised an eyebrow, curiously. „ Why would it be more complicated?“ He inquired, leaning against the aisle lazily. „Well as a principal I don’t really hav much time to … to date.“ I feel my cheeks heat up a bit. Beau scoffed. „Oh cmon, I don't believe that. You cant tell me that every second of your life is spent working. You have free time.“ He said with a bit of disbelief, chuckling softly. „I do yes. But I also am freshly divorced… so…“ He raised an eyebrow then, looking at me more curiously now. He wasn’t expecting that. „Oh you are?“ He inquired, tilting his head to the side a bit. He took a small step in my direction. 

I bite on my lip, a bad habit, and slowly nod. „Recently divorced, huh?“ Beau continues to ask, the small smirk still on his face as he looks at me. He leaned against the aisle again. „Can I ask why?“ 

I look up at him a small chuckle escaping my lips. „Oh thats a long story sheriff.“ 

And just then, Emily comes into the aisle. „Oh hello Emily.“ I smile at her, catching Beaus reaction as he turns around to see his daughter. „Hello“ is all that comes out of the teenager, a normal reaction to students meeting their principal outside of school. Beaus attention is still on me, still with that smirk on his face. „Oh Ive got all the time in the world.“ Emily catches the vibes and looks between us. „Wait, are you guys flirting?“ She asks a bit curious and weirded out. Beau immediately looked at Emily, clearing his throat as his face flushed a bit red. „N-no.“ He said, hoping his voice sounded normal. He looked back at me, still a tiny bit flushed. I try to safe the situation and escape it by saying „ No we’re not Emily.“ I smile at her and then up at Beau „well, I wish you two a good evening“ and with that I turn around and go on into an aisle where I absolutely don’t need anything, but Im happy that I could escape that awkward situation. 

Beau nodded, his eyes following my form as I left. He sighing softly as he looked over at Emily, who gave him a cheeky smirk. Beau just rolled his eyes at his daughter. „Quit it, Em.“ He said as he continued shopping. „I didn’t notice you were such a player, dad“ She said with a taunting voice and a mischievous look in her eyes. Beau scoffed. „Oh shut it.“ He said with a hint of annoyance in his voice. He was still focused on his grocery shopping, grabbing a pack of cereal and putting it in his basket. Emily chuckled, clearly enjoying teasing her father. She walked a few steps ahead of him, turning around so she could walk backwards and face him. „You were totally checking her out, dad.“ Beaus ears turned red at her comment. He looked at her, still walking and rolled his eyes. „I was not“ He died to deny it, but even he knew it was a bad lie. Emily raised her eyebrows, a smirk on her face. „Oh you so weever. You were looking right at her butt, when she left.“ Beaus face flushed an even deeper shade of rad at that. He let out a soft huff, rolling his eyes yet again. „I was not looking at her… butt.“ He denied it, but was doing a terrible job at it. Emily crossed her arms, a teasing grin on her face. „Come ooon dad, admit it. She’s totally your type.“

“Shhh, there could still be more.”

“PLEASE HELP MY HUSBAND!” You nod to her and move on to the next room where you find a vampire. Now something really feels off- you don’t remember running into him. He turns and you expect to see the husband but instead you see Dean, all bloody, looking at you with glassy empty eyes. “NOOOOOOO! You scream.

With a start you sit up in bed. Thank god. It was only a dream. You turn over in bed only to be greeted by bloody dead Dean. “Its all your fault. I’m dead because of you.”

You wake up screaming and fall out of bed with a loud thump. You hear footsteps running down the hallway and Sam runs into the room with his gun drawn. Oops. You forgot you and Sam share a wall so of course he would be the one to arrive. Part of you wishes it were Dean. 

“Y/N?! What’s wrong?!”

“I’m so sorry Sammy, false alarm. Just a bad dream, I didn’t mean to wake you up…”

“What was it?”

“I saw Dean. It was my fault he died and there was nothing I could do to save him…”

“Hey- it’s okay, it was just a nightmare.”

“Hey Sammy?”

“Yes Y/N?”

“Do you mind sitting here for a little bit so I can fall asleep? Please?”

“Sure, I- uh- of course.” Sam stutters through his sentence.

“And Sammy?”

“Yes?”

“Please promise me you won’t tell Dean about this… I don’t want him to worry or think I can’t handle hunting with you guys.”

“Y/N…”

“Promise!”

“Okay. I promise.”

“Thank you.”

Months pass and the night terrors continue. Always varying but the ending always the same- Dean dying and it being all your fault. Sam was there through all those late nights, keeping an eye on you, always making sure you were alright after waking up screaming. Through all those months he never told Dean about the dreams and for that, you were so thankful. Unfortunately, your team’s latest encounter with Crowley left everyone on edge. He knew how to get into everyone’s head but loved toying with Dean, especially. Minutes felt like hours with Crowley watching him tear down Sam and Dean. When Crowley turned to look at you, you could feel your heart beat start to quicken and you knew he could hear.

“Nervous are we?” he chuckled darkly.

“Screw you.” 

“Haha oh my dear, you’ve been keeping secrets. Does Dean know?”

“Know what?” Dean growled

“This pretty little huntress has been having night terrors. *pause to turn to Dean* About you. I personally find them quite entertaining to watch. It does get too soap opera-ey for me though every time Sam rushes in.” 

With a whoosh Crowley disappeared into thin air. 

“Dean- “ Sam and you both started, but he had already started out toward the Impala. The entire ride back to the bunker was quiet, high tension in the air. The only sound was coming from Dean’s favorite ACDC mix tape. He brings the Impala to a slow stop on the gravel driveway with a familiar crunch which would normally be comforting but is now deafening. Without a word, Dean gets out of the car and walks inside, you and Sam trailing behind him like puppy dogs. Once you’re inside the words start to gush out from both you and Sam.

“Dean-” Sam starts- “listen, I wanted to tell you, but it wasn’t my place to say anything.”

“Its fine Sammy.” Dean snaps. “You can go. I need to talk with her alone.”

Sam turns to leave but not before you see his expression- the one he makes before Dean loses it. You gulp and turn to see Dean staring right into your eyes. Did he get closer? Or am I just nervous? 

“You should have told me Y/N.”

“I know but-”

“How long has this been going on?”

“Dean- “

“HOW LONG?”

“.....Since the night all those months ago when me and Sam went on that vampire hunt that went bad.”

Dean closes his eyes momentarily to pinch the bridge of his nose but then he goes right back to staring into your soul with those eyes of his…

“I wanted to tell you but I didn’t want you to stop me from hunting with you guys. I’m so sorry Dean-” tears started to form “I don’t want to lose you, Dean, I-”

He cuts you short, cupping your face in his big hands, his warm plump lips pressed against yours in a gentle kiss…

“You would never lose me Y/N, and you have no idea how long I’ve wanted to kiss you. I’m scared of losing you too, every time we go on a hunt. It’s part of why I’m so hard on you, I just want you to be careful. I love you Y/N.”

Your eyes tear up at his words, the waterworks getting closer to spilling over with every passing moment in this beautiful jewel of time.

“I love you too Dean.” You smile, your hand now cupping his as you enjoy his embrace. 

“How about you sleep with me tonight, Y/N?”

"Mornin' Apple-Pie!" Dean's cheery voice echoes through the small motel room, magnified by the side-splitting headache you have.

"Ugh. How long was I out?" You ask, sitting up while rubbing your head, willing the pain to go away. Dean pushes you back on the bed before you manage to make it into a sitting position, though.

"No no no, you gotta stay down. That bitch got you real good. Sliced your side right open. And don't worry, you've only been out since last night. I do gotta say, you were a real pain-in-the-ass to get in the car."

"Sorry," you mumble.

"Why'd you head back? You should've kept running." Dean looks at you curiously.

You can feel the blood rising in your cheeks. "I thought I heard you and Sam in trouble. Figured if I didn't come back you'd kill me." You try joking your way out of it.

"Yeah, well you're just lucky the chihuahua on steroids didn't kill you first. Cas should be here soon to heal you. If we can talk him into it, we're gonna head down to that karaoke bar you wanted to check out a couple of towns over."

You mumble an "okay" as you lay back down and start to drift off.

You wake up to a warm heat coursing through your body. You open your eyes as you see Castiel withdraw his hand from your side.

"Thanks, Cas." You say, standing up. "We going to that bar?" You question them. When you see Dean nod, you race to grab your duffle bag and hop in the shower.

Once finished, you push the sleeves of your AC/DC shirt up to your elbows. You quickly straighten your hair and apply your makeup before walking out to grab your combat boots.

Looking around, you notice all the boys have left, you assume they went back to the Winchesters' room.

You slip your shoes on with ease and grab your wallet, then you're out.

You arrive outside Sam and Dean's door, only to be met with arguing in hushed whispers.

"No, Sam! It's not happening. You know the closer we are to someone, the more danger they're in. Why would you want to do that?"

Confused, you knock on the door. "Hey guys, you ready to go?"

You hear one of them shushing the other and rushing to get the door.

Dean greets you with his warm smile. "Yeah, Apple-pie. We're ready." He hurries past you and hops in Baby, leaving you to shoot a questioning glance towards Sam, who just brushes it off.

The drive to the bar was filled with classic rock and you and Dean having a "who's singing can irritate Sam more?" contest. You ended up winning, much to Dean's dismay.

When you finally got to the bar Bertha's, you ran inside as fast as you could, grabbing a table in the back. The boys soon followed, Cas having met them outside.

"Heya, Cassy-boy." You smiled.

"Hello, Y/N. How is your side feeling?"

"I'm great. Takes a little more than some mutt to keep me down." You chuckled.

"Well, Imma go get us some beers," Dean said, walking up to the bar.

"So," Sam turned to you. "You gonna sing tonight? Or did you just drag us here to listen to the other drunks?"

"I want to sing..." You said, turning away.

"But...?"

"But I'm kinda scared." You mumbled towards the floor. You heard Sam laughing when you said this. You whipped your head around to face him. "What?"

"Nothing. I'm just a little surprised that Y/N, one of the most badass hunters I know, the girl who's afraid of nothing, is scared to sing in public."

"Who's scared of what?" Dean asked, walking back to the table, setting the beers down.

"Y/N's scared to sing on stage." Cas piped up, joining the conversation, flinching when you slapped his arm.

"You're scared? Of what? They're just a bunch of drunk morons." Dean said.

"It's nothing. Don't worry. I'm sorry I made you guys come here. We should have just gone back to the bunker. "

"Come on, Y/N." Dean placed his hand on your shoulder, causing you to look at him. "What if I sing something too? Will you get up there then?"

Thinking it over, you decided that if Dean got up there and embarrassed himself, you could too. "Yeah. I guess."

"Great. Let's go sign up." Dean grabbed your arm and led you to where you signed up to sing. Once he was registered, you had him go back to the table, telling him you had to take a minute to pick out a song.

You knew what song you wanted to sing. It had been stuck in your head for weeks after a late night watching random youtube videos. The only problem, besides stage fright, was that the song was everything you wanted to say but were too afraid to. You headed back to the table after a few minutes, taking a long drink of your beer.

"So, you decide on a song?" Sam asked. You just nodded yes, feeling your face flush at the thought of actually getting on stage. "What'd you choose?"

Setting your beer down, you smirked at him in hopes to play it off. "You'll just have to wait and see Sammy-boy."

They seem to accept that and you guys spend the next half hour listening to the people on stage before Dean's name gets called. He shoots a wink at you before heading up there and it takes all you have to fight the blush. This is Dean we're talking about. He does that all the time. It means nothing.

For someone who says he hates to sing, he owns the stage like he was made for it. If you didn't live the life you did, you definitely would've pushed him to be on one of the singing competition shows. That's stupid Y/N, if you didn't live this life you wouldn't have ever met him.  

Tennessee Whiskey by Chris Stapleton starts playing over the speakers. Huh, why would he choose this? Dean always acts like he hates country. He starts singing and it feels like your insides turned to soup. You'd never let anyone else know it, but Dean's singing is always something that calms you. When you have a nightmare or after a hunt gone wrong, Dean would come to your room and just sing to help you feel better. If you guys were in a motel with Sam, he's just hum and try to take your mind off of whatever's bothering you. It usually ended with you drifting off during it, and afterward, you two would have an unspoken agreement to not talk about it.

The song finishes way too soon for your liking. Dean joins you guys back at the table and you just smile and listen to Sam tease him about his choice in music. Then comes what you've been dreading all night. Your name gets called to come on stage. You look between the boys with wide eyes as they all but push you out of your seat and towards the stage.

You take the microphone and close your eyes as the music starts.

I never thought that you would be the one to hold my heart But you came around And you knocked me off the ground from the start

You put your arms around me And I believe that it's easier for you to let me go You put your arms around me and I'm home

You opened your eyes and looked over at your best friends, seeing Sam and Cas with huge smiles watching you. Dean, however, had a much smaller smile on his face. He looked almost wistful. He nodded at you to continue, giving you the encouragement you needed. Little did he know you were singing to him.

How many times will let you me change my mind and turn around I can't decide if I'll let you save my life or if I'll drown

I hope that you see right through my walls I hope that you catch me, 'cause I'm already falling I'll never let a love get so close You put your arms around me and I'm home

You thought back as you sang, to all the times Dean's been there for you. All the late night whispered conversations in motel rooms as Sam slept. All the trips to bars together after successful hunts where you two would celebrate. All the nights where he found you crying after losing someone.

I hope that you see right through my walls I hope that you catch me, 'cause I'm already falling I'll never let a love get so close You put your arms around me and I'm home

The world is coming down on me And I can't find a reason to be loved I never wanna leave you But I can't make you bleed if I'm alone

You think about how you aren't good enough for him. He deserves someone who could give him the perfect life. A life with no monsters and no worries about if today's gonna be his last day. Someone who can give him kids and a house to come home to every day, not some secret underground lair for monster hunters.

You put your arms around me And I believe that it's easier for you to let me go

I hope that you see right through my walls I hope that you catch me, 'cause I'm already falling I'll never let a love get so close You put your arms around me and I'm home

You know Dean though. Even if he found someone to get out of the life for, he would never do it. He'd never even consider being with someone. He's so convinced that it'd only end bloody. Guess that's another thing you have in common. You would never tell him how you felt. There's no chance he'd feel the same, and even if he did, you couldn't handle being the reason he gets hurt.

I tried my best to never let you in to see the truth And I've never opened up I've never truly loved 'till you put your arms around me And I believe that it's easier for you to let me go

I hope that you see right through my walls I hope that you catch me, 'cause I'm already falling I'll never let a love get so close You put your arms around me and I'm home

You put your arms around me and I'm home

The song ended and you brought your hand up to your face. You didn't realize a tear had fallen down. Well shit, that's not gonna seem suspicious. You make your way back over to the table and immediately the boys have you wrapped in a hug, telling you how good you sounded up there. You brush them off and pick up your beer.

You guys leave pretty soon after that and start heading back to the bunker.

You all got back to the bunker around 1 am. You decided to just head straight to your room with claims of being tired. You weren't, but they didn't need to know you just didn't feel like being out there with them right now. You managed to avoid questions about your song choice on the way home, but you didn't want to risk anything else tonight. Surely they'd forget about it by tomorrow morning.

In your room, you throw on a tank top and some shorts that are way too short for your liking, but they're the only thing you can find right now and you don't have the energy to keep looking. You get out your laptop and look up Tennessee Whiskey on youtube. You didn't bother with headphones, instead just setting the computer down on your nightstand and lay back.

You have your eyes closed, just listening to the music. You didn't hear the soft knock at your door, or it cracking open when you didn't answer. Dean walks in, a small smile tugging at his lips as he looks at you.

"Hey Y/N" he softly says. You shoot up from your bed, instinctually looking for the threat. When all you can find is Dean, you smile. "I, uh, wasn't quite as good as the original, huh?" He laughs dryly.

"I was actually thinking the opposite. Little upset I had to settle for this." I motion to my laptop and pause the video. "Would you maybe sing for me?" I ask quietly, avoiding looking at him.

Without saying anything he comes over to the other side of the bed and climbs in. You join him and lift the covers over you like you've done so many nights before. He pulls you to his chest as he leans against the headboard and starts singing like he does whenever you're scared. You start drifting off to the vibrations of his chest as he finishes Tennessee Whiskey (which you've now decided is definitely your favorite song.) You're just about asleep when a tiny voice catches your attention.

"Do you think I'm stupid?" Well, that has you awake.

"You are the smartest person I know Dean. Why are you asking that?" You don't move your head from his chest, instead, you subconsciously rub small patterns with your fingers.

"I know why you chose that song Y/N/N." You still, not sure you can say anything. Does he really know?  "Aren't you gonna ask why I chose the one I did?" When it becomes apparent you aren't going to say anything, he continues. "I've spent years trying to drown myself in alcohol to forget all of the bad we face every day. If I wasn't hunting, I was drinking. I knew it wouldn't make me forget completely, but I could at least drink until a new hunt came along. But then you joined us. I always had to protect Sammy. My whole life I've known nothing else. He always came number one. But when you came along and joined our little crappy makeshift family? Well, things didn't seem so crappy anymore.

"Ever since my mom died, it was like my family wasn't complete. It always felt like we were searching for something. But meeting you was like the search was over. Like all this shit me and Sammy have been through was just leading up to meeting you. And damn sweetheart, if you weren't the best reward anyone could ever ask for. After that, it's like I didn't feel the need to drink my nights away. I'd rather be sober and stay up all night talking with you. You are the best damn alcohol I've ever had."

You stayed silent for a while, fearing that your voice would give way. Although the tears soaking through his shirt probably did a good enough job on their own.

"Please Apple-Pie, say something." He sounded almost scared. Like saying all of that was gonna push you away.

"I'm scared, Dean." You admitted. "What if something happens to you because of me? We don't exactly live the safest lives? And what about if something happens between the two of us? I wouldn't just lose you, I'd lose Sam and Cas. And not to mention I can't give you the apple pie life with two kids and a picket fence?" He cut off your rambling by grabbing your face and pulling you towards him in a slow kiss.

"Y/N. You think I haven't thought of all of that? First of all, nothing will happen between us. And even if it did, Sam and Cas would definitely choose you." He laughed. "I don't want that apple pie life, I just want my Apple-Pie with me every night. And the risk of putting you in danger is the only thing that's kept me from saying all of this the day I met you. I love you, Y/N. And I want to spend however long we have in this screwed up life with you by my side."

You looked up at him for a long time, your face still in his hands. Maybe things can work out in your favor. You love Dean. If you have the chance to be happy, however fleeting, maybe it's worth the risk to take it.

You’ve decided to try babysitting for some extra cash and you were about to give up hope and stop sticking up your number around town to babysit. You made over one hundred bright pink flyers, each one with strips of your number on the bottom.

You had been hanging up flyers for the past month now, but who in their right minds would hire a stranger to babysit their kids?

You thought maybe babysitting was a good idea for the extra cash. You were currently attending school at some nearby college and still lived with your parents because let’s be honest, it’s hard to take classes, work and live by yourself. 

But living with your parents with no job meant that you were always broke. Want to go eat? Broke. Want to go shopping? Broke. Want to go somewhere nice? Broke.

You were tired of it. You wanted your own money to buy yourself your own things instead of having to ask your parents, and also to maybe help your parents with some overly-priced bills.

It was getting dark and you decided that hanging up seventy flyers was enough for the day and that you will just continue to hang the rest tomorrow. You got home and your dad was home from work, and your mom was cooking.

“Honey, dinner is almost ready!” Your mom shouted to you as you began walking upstairs to your room.

“No thank you, mom. I ate just before I left. I’m just going to head to my room.” You said back to her.

You continued to your room and threw your bag on the floor and flopped yourself onto your bed, another unsuccessful day.

Your bones cracked a few times as you laid yourself flat on your bed and you sighed. You’re not getting any younger and you wished you could flash forward to when you had a stable job and your own home.

You began to drift off into a slumber when your phone began to ring, making you jump quite hard.

You ran to your bag on the floor and quickly unzipped it, taking your phone out and answering the unknown number that was calling.

“Hello?” You grimaced at the sound of your disgusting scratchy voice, caused by your almost sleep a few seconds ago.

“Yes, hello. My name is Dean Smith and I’m calling about this babysitting service that you posted up on this flyer?”

The voice almost made you wet your pants. The man’s voice was so deep and sexy that you already wanted to see what this man looked like and who he was.

“Yes, that’s me! What can I help you with?” You asked with a voice that you tried to make it sound like you were purely business, but you were failing miserably.

“I was wondering if maybe you can come to my house tomorrow so I can ask you some questions about yourself? I want you as a babysitter for my kids but I just want to get to know you before allowing you to watch them. Will that be okay? At around three in the afternoon?”

“Sure thing!” You replied a little too embarrassingly loud.

“Okay then, it’s settled. Do you text? If you do, I’ll just send you my house address.”

“Yes I text.” Was all that you said, and you felt like you should’ve said more.

“Okay then! I’ll just text you. Good-bye!”

You said bye back and you both hung up. You waited impatiently for the man to send you his address. When he did, you quickly put the address into Google maps.

“Holy cow!” You couldn’t believe where this man lived. He lives in the Beverly-Freaking-Hills! What the hell would this man want with a person who needs to put out flyers to find a job rather than finding some professional?

Honestly, you were now intimidated. This man, his wife and his kids probably have it all.

You put your phone on your charger and got back into bed. You closed your eyes to fall back asleep and your dreams were filled with nothing but that voice on the other side of the phone and guesses on what the man looked like.

::

You hadn’t done anything all day because you were nervous to meet this man.

“This man lives in Beverly Hills, mom!”

“Well maybe he just wants to help someone out. Plus, maybe he will make you his girlfriend in the long run.” Your mom winked your way, making you blush at her words.

“Doubt it. He has kids, so that must mean he has a wife, right?” You asked your mom as you picked at your salad.

“Not necessarily. The mom might not be in their lives.”

You thought your mom was right. If two adults, one man and one woman, needed a babysitter, you would think the woman would call. But you guessed you would find out soon enough.

It was time to leave so you got into your small 1967 red Chevrolet Malibu, and you made your way up town.

Half an hour later, you made your way into a huge community filled with homes that you never seen so big. You were amazed by the way these homes looked. They all had to be at least three stories high.

Your driving came to a slow halt as you found the house with your GPS. You parked your car on the street, right outside the big white home, and walked up to the door.

You nervously rang the doorbell and waited impatiently.

A man no later than his late thirties, in a nice white shirt, opened the door and smiled widely at you. “Hello, come in.”

You walked in and the house smelled like cleaning product, as the house looked completely spick and span. Not a single dirt spot anywhere. 

The man lead you to an office room that was on the second story of the house, and gestured you to sit at a table right next to him. He looked up at you and the sun shining in from the window within the room, made you fall in love with his eyes. His eyes were rainforest green and you couldn’t believe how green they were. Yet, here you were with boring Y/E/C eyes that more than half the world has.

“So to start off, can I get a name?” The man asked you. You began to speak and his cologne lingered into your nostrils, making him sexier now that he smells good too.

“My name is Y/N.”

“Okay, Y/N, tell me about yourself.” The man stared at you and your heart began to beat against your ribcage and you felt like the man could hear your heart beats.

“Well I’m twenty-four years old. I’m currently attending a college within my hometown with a major in English. I am the second child out of four within my immediate family. I love children. I’ve volunteered numerous times at elementary schools and at summer camps.”

The man smiled, satisfied with your answer. “Do you have any children of your own? A family of your own?”

You were quite embarrassed at his question. Should you have had a family by now? Did he have a family by the age of twenty-four?

“Uh, no, I don’t.” You responded.

“Any boyfriends or husbands that I should know about?” He asked, looking straight into your eyes.

“No, sir.” You replied simply.

He continued to smile and it began to make your hands sweat.

“Please, call me Dean,” He started. “So it looks like I’m going to hire you. I was thinking maybe I could pay you $50 per hour?”

Your eyebrows raised in amazement. You were only going to ask for $50 per day.

“You’re right, that’s not enough. How’s $75 per hour?”

You began to laugh because Dean clearly took your expression the wrong way. “That’s more than enough. What times would you need me to babysit?”

“Okay now don’t be mad, but I’m going to need you to babysit overnight. From seven in the evening to seven in the morning. I’ll be home by then and I’ll be able to get the kids up and ready for school, so don’t worry about that.”

Jesus Christ! Twelve hours! You thought if you would ever be able to sleep in your own bed again if you took this job.

Your hesitation to say yes to the job made Dean continue to talk. “I have several guest rooms in here, but unfortunately only one of them is fully equipped. It also has a restroom within the room, and that’s where you will be staying. The room is between my room and the kids room.”

Would it really be so bad to take the job? Maybe you can sleep at home on the weekends and on weekdays stay here. So that means, you would have to come to his house straight after school, considering you get out of school at six in the evening. Not to mention, that’s $900 for every time you babysit!

“I’ll take it.” You stated.

Once again, Dean smiled and it looked like his eyes became greener. He bent over to you and took you into his arms in a big hug, which surprised you only a lot.

You hugged back, patting his back and he continuously thanked you for taking the job.

He pulled away and got up. You got up as well and he stopped in the doorway. “Come meet my kids.”

You both walked down the stairs and into the living room where a huge t.v. screen played Spongebob.

“Kiddos, I want you to meet someone!” All the kids ran to their dad as you made a head count of how many children you would be watching. Three kids, not too bad.

“Sam, John and Mary, meet Y/N!” Dean said happily to the kids.

All three kids smiled at you and ran to you in a big hug. You made a slight oomph, as the children squeezed a little too hard.

“They’re so cute and loving. I see they’re huggers too. Get it from their dad?” You laughed.

Dean laughed too. “Sorry about that hug. Ever since their M-O-M left a few years ago, it’s been hard to take care of them and run a company.” He stated.

Your eyes widened as he mentioned his occupation. “You run a company? No offense, but why in the world would you want to hire someone who isn’t all that experienced whereas there’s professionals everywhere that would be more than willing to take your money?”

Dean hesitated to answer and you could tell he was thinking before he decided to answer you. “You’re right. But unfortunately, professionals keep everything strictly professional. I would much rather have a family person who needs the money and loves family just as much as me. Family means everything to me. I was once a struggling kid in college and I know you are as well, otherwise you wouldn’t have taken a job caring for three little maniacs.”

You and Dean both laughed as he called his kids maniacs.

“One more thing, let me show you around the house.”

Dean showed you the whole house and it was practically a work out. The kitchen was as big as your room and you couldn’t wait to cook in it. He had several living rooms, although in your opinion you thought that was useless. He had three bathrooms downstairs as well as three bedrooms. Up the stairs, he showed you the theater room which astounded you, and he showed you his office room as well as the master bedroom, the fully furnished guest room, the laundry room and the kids rooms. On the third story, there was a huge storage room as well as several other rooms that Dean said he was too lazy to show you.

You both walked back down both flights of stairs and he took you to his backyard patio. He showed you the huge pool and jacuzzi as well as the tiki bar and the giant game room that was to the left.

“So I was wondering if maybe you could start tomorrow? You are more than welcomed to eat whatever is in the fridge. I have a maid that comes over so she will be here when you get here. She usually makes dinner for the kids, cleans, does laundry, and then leaves.”

You nodded in understanding.

“Okay it’s settled then. You are welcomed to stay and get to know the kids or me, maybe.”

You looked up at Dean and he was blushing, but he stared into your eyes to make it seem like he was being totally normal.

“I actual have to get home and help my mom with dinner. But I just want to say, thank you so much Dean. For this opportunity. I was really hoping for someone to call me back. I’ve tried for a long time now and you’re the only person who needed a babysitter.”

“No problem, Y/N. I will walk you out.”

He walked you out as you stepped out of his home and he walked you to your car.

“Have a thing for classic cars, I see?” Dean gestured towards your car.

“Yes. They are my weakness.” You smiled at him as he practically drooled over your car.

“I actually have a black ‘67 Chevy Impala in my garage along with several other cars, but my Chevy is my baby. I need to show you them, but that’s due for another day.” He smiled.

You decided to walk up to him and hug him. He smelled so good and you felt his big muscled arms wrap around you and for a second, you thought he ran his fingers through your hair.

You got into your car after you thanked him practically a million times, and you drove back home, happier than ever that you found a place that would pay you good. Plus, the dad is hot and the kids are sweet.

::

Four years later and you finally saved up enough money and helped your parents pay enough of their bills, that you decided it was finally time to move out.

You got yourself a nice small apartment, not too far from your old home, that was surprisingly cheap. The environment around the apartment was peaceful and quiet and the little porch outside of your sliding door windows received enough sunlight for your daily reading. You finally graduated with your degree in English, feeling accomplished.

You still continued to babysit Dean’s children. Although, they were so much more older now. Mary is now twelve, John is eleven and Sam is ten. Crazy ages.

Now that Mary was getting older, she was developing a major attitude now especially towards Dean. But for some reason, not unknown to you, she always vented to you about the latest gossip in her middle school and who was holding hands with who.

John is such a game nerd, but he sure does have an infinite amount of knowledge when it comes to technology. You recently got a new phone and didn’t know how to work the camera, but John quickly became acquainted with your phone and helped you out. He even showed you how to use it step by step.

Sam on the other hand, he was such a quiet kid but super sweet at the same time. He loved to read books. What you decided to do was bring him a new book every two weeks, since he reads them that quickly anyways. The new books that you bring always light up his face like if it’s Christmas.

You grew to love these kids. You seen them everyday that they became family to you. It would be unusual if you didn’t babysit them that day, like if something was missing.

“You know, Sam, Mary and John are getting older now.” Dean said softly before he left to work.

You nodded your head in agreement as you watched the kids do their homework. You were chewing on a carrot stick that you originally pulled out for the kids to munch on.

“They’re getting old enough to watch themselves now.”

You finally knew where this was going. You stopped chewing and looked at Dean. He had a sad expression on his face.

“What are you saying, Dean?” You wanted him to be straightforward, but that was definitely something you learned that he was not well at doing over the course of four years.

“I’m sorry Y/N. But unfortunately, these kids are getting older and I won’t have a need for a babysitter anymore. Mary is going to be thirteen in a few months and she is mature enough to be alone and take care of her brothers.”

He was whispering now, and you knew he didn’t want the kids to hear. You knew they would be heartbroken if they knew you weren’t going to babysit anymore.

“You’re firing me?” You began. Tears started to flow and your throat was burning from trying so hard to hold back tears. “Dean please. I love your kids. Don’t do this please. They are my family. You are my family.”

Dean looked doleful, but you knew he meant what he said and he wasn’t going back.

“Today will be the last day. I have to go to work now.”

And then he left. Just like that. Clearly he didn’t realize the attachment you had with his kids. Or maybe he just didn’t care?

You didn’t know what you were going to do and you were becoming scared. Of course you still had your parents and your brother and sisters but unfortunately for you, your brother and sisters lived in other states and you know your parents love being alone now that you’ve moved out.

Once Dean left, the time seemed to pass by quick. Mary spoke to you about school and you hugged her a little longer after her discussion about school. You played games with John a little longer than usual, knowing that it will be the last time. You talked books with Sam, expecting to miss what a smart kid he was about everything because of the many books he’s read.

Night came by and the morning came quicker. Dean walked into the guest room to wake you of your slumber.

“You can go home now. I left your last paycheck on the counter.” He whispered.

You looked at his face, but he was blank. Nothing showed across his face and it made you feel worse. You remembered last night. You cried yourself to sleep knowing you won’t see these kids anymore. Or Dean.

You knew you were going to miss Dean a lot as well. He was so kind and generous to you. He’s even taken you out on a few dates as well when he didn’t have work and when the kids were at school. You thought being fired was your fault, but you couldn’t remember doing anything wrong.

You left the Smith residence quickly, not wanting Dean to see any tears fall from your face as you exited the house. You got into your red Chevy and drove home.

It was quiet. But now, it was too quiet for your liking and you didn’t like to be alone with your thoughts. You kept thinking maybe you said something to the kids and they repeated what you said to Dean. Or maybe it was that time that you forgot to throw away the trash that the kids left on the counter. Or maybe it was that time you let the kids go in the pool when it was cold, but they kept begging.

You realized now, that you had to go out and get a real job. Thank goodness for your education.

Quicker than you could register, you found a decent paying job being an editor at some magazine company in Los Angeles. Of course it was quite a travel from your home, but your hometown was the country and not the city.

You weren’t feeling the hype of being an editor. You made some friends outside of work and they always became thrilled when you told them that you were an editor at Los Angeles Magazine. Literally all you did was edit people’s journal entries for the magazine, and that was it.

You missed babysitting. You tried getting them and Dean off of your mind, but everything you did reminded you of them.

Whenever your friends gossip, guess who it reminded you of? When you passed by the many billboards of new video games, guess who it reminded you of? Guess who it reminded you of when you tried to read on your porch?

Worst of all, guess who you remembered working at a company owned by one of the most wealthiest men in L.A.?

You hated it but you were helpless. You couldn’t do anything. You tried calling Dean to at least talk to the kids, but he changed his number which made your heart break. Before he changed his number, he even told you not to come back to his house.

Months passed by and you were still unhappy with your job and everything that surrounded you. Your mom insisted you move back in with them if you hated your job so much. But you couldn’t do that to them. They struggled trying to feed three people, you didn’t want to put them through that again.

Your routine was always the same. Wake up, go to work for an eight hour shift, have dinner with yourself, and then go home and clean up your house or maybe do some laundry. It was lonely and you didn’t feel this way before. The quiet turned into an annoying silence that was driving you insane.

Today was the same thing again. You separated your clothes and put them into the washer and then walked back to your apartment. The bad thing about the complexes were that you had to share a washer and a dryer.

You walked back to your apartment with you hamper in your hand when you seen a man squatting down with his head in his hands, right in front of your door.

The man was wearing grey sweats and a blue pullover sweater, but you knew he wasn’t homeless because he was wearing clean Nike shoes and his clothes were clean.

“Um, sir? Do you need something?”

You heard the man sobbing as you walked closer to him, but stopped when you spoke. He looked up and those eyes were the same ones that drew you in the first time you met him.

“Dean? What are you doing here?” You became frantic when you assumed something was wrong if Dean was at your front door, crying.

Dean got up from his position and walked to you and pulled you into a hug. The calming smell of him suddenly pulled you back into your memories and you began to hug him back. You rubbed his back until he pulled away first.

“I’m so sorry.” Was all he said as he was shaking from crying so much.

“It’s okay, Dean. Tell me, what happened?”

“I need you back. The kids need you back. We all miss you so much. I’m so sorry I fired you. I never should have told you to leave.”

You brought your hand up and wiped the tears from Dean’s soft face, your other hand going to his shoulder.

“Dean it’s oka…”

“It’s not okay! Okay? I fired you because I’m a sissy that couldn’t tell you my real feelings for you. So I pushed you away thinking it would make things better but I only thought of you even more!”

You were completely startled by his sudden rush of honesty of his feelings for you. Your hands dropped to your sides as you tried to process what Dean just said.

He has feelings for you. Do you feel the same? Of course you do, otherwise you wouldn’t have felt so depressed from the time he fired you.

“Dean, I…”

“Please, if you don’t feel the same way, just say it. Don’t hold back.”

“Dean, I love you Dean. I love your kids too. So much. I’ve loved you for a long time but I never thought you would want to be with me because I thought you were always just too busy to be with someone. But then, if you have feelings for me, why did you fire me?”

Dean turned his back towards you as you waited patiently for his answer. A few seconds passed and he turned back around to answer you.

“At first it was just a friendly relationship that we had. I loved how happy you made my kids and that made me happy. A year passed by and I noticed I was becoming attached to you. That’s when I started inviting you over even on your days off. Two years passed and I realized my feelings for you were way more than just liking. I was starting to love you and it was scaring me. So I began to work later shifts. I would come home later than usual and I made the kids go to school later. Finally, I just couldn’t handle it. You were constantly on my mind, so that’s why I did what I did.”

Dean was fidgeting and swaying side to side nervously, but continued to talk.

“At first I told the kids you found a new job and you were too busy to babysit them. I got a new babysitter but it just wasn’t the same. At night, I would hear the kids go to bed crying. There wasn’t a day I didn’t think of you, Y/N.”

You were so mesmerized by what he said that you grabbed him by his big shoulders and smashed his lips to yours. You had to do it. The urge was becoming too strong and you had a feeling he wasn’t going to make the first move any time soon.

Your arms wrapped around his neck and his arms wrapped around your waist as your lips and his lips molded and became one. His lips were soft and felt exactly the way you imagined it would and you had the feeling in your stomach that you imagined you would get if you ever kissed him.

But this was it. You were kissing him and holding him and you didn’t want to let go. You’ve never loved a man as much as you loved Dean Smith.

::

“Mom, can I go out with some friends tonight?” Mary asked you.

“Of course sweetheart. Just don’t be out too late. Call me if anything happens and you know I’ll be there.”

“Mom, can we go to the library?” Sam asked coming out of his room.

You nodded and smiled as he smiled widely and excitedly.

“Mom, I want this game. Can you get it for me when you have money?” John asked so nicely.

“Sure. As long as it’s not a violent game, I’ll be more than happy to.” You replied.

“Hey sweetheart.” Dean came up to you and kissed you on your temple as you were making dinner. Dean finally cut his own hours to spend more time with his family. You and him. Yours and Dean’s yearly income was way over the top and you two didn’t have to work so much. You also didn’t have to travel as far, so you kept your job in Los Angeles now that you lived in the rich community of Beverly Hills.

“You know I love you right? And the kids love you?” Dean said as he massaged my shoulders.

“Of course Dean. I love you guys too. So much.” You continued to cut vegetables to make some soup that your mom was more than happy to share the recipe with you.

You dunked the vegetables in the pot and turned towards Dean. He wrapped his arms around your waist and you wrapped your arms around his neck. Dean looked down and smiled, caressing your stomach. He lowered himself and placed a soft kiss on your tummy.

“I especially love our upcoming special addition to our family.”

You pecked Dean on the lips as he got back up and you pulled away from him. He wrapped his arms around you from behind and began to rub your eight month big tummy.

“Yes. I especially love our little Cassie that will soon be joining us.”

"I thought that was a given?" Sam smiles back, chuckling.

"Ha ha ha," Dean rolls his eyes. "Now that we've had our little love fest, why don't you leave us alone, so that I can spend time with my girl?"

My girl, you think, smiling. A shiver runs through your body. You'll never get over the feeling of being his. Dean Winchester's girl.

Sam held up his hands in defense, turned, and walked to the bedroom. Dean grabs you into a hug once more, this time closer and more loving. He'd never show Sam this affectionate side of him. Dean would believe himself to be "less masculine," if anyone saw it. You thought it just made him more of a man, and truly revealed how much love he possesses in his heart.

Dean took in a huge breath, his chest expanding against yours. He seemed to feel relaxed in your arms. After a job as hard as his, he absolutely needed to feel loved and wanted. You lean your head against him, your hand gently stroking the back of his neck and the bottom of his hairline.

Suddenly, Dean's body tensed up. Almost every muscle tightened.

He pulled away, walking to the kitchen. He opened the refrigerator and grabbed a beer, quickly popping it open.

You're taken back at how fast he moved away, and knew that something was bothering him. "What's wrong?"

He looked down, avoiding your eyes. He took a swig of beer and sat down at the kitchen table. "Nothing, babe. Long day."

"And?" You cross your arms, making your way towards him.

"And," he says mockingly, "I'm tired."

"And hurt." you add.

He quickly looked up to you, and for a second you could see the pain in his eyes. He looked down again, taking another swig of beer.

You sit down and put your hand on top of his. "You can tell me, Dean. Was it about me?"

He shook his head.

"Was it about Sammy?"

He shook his head.

"Was it about your mom?"

You could see his breath hitch. You had hit a nerve. Squeezing his hand, you plead, "Tell me about it. Please. I want to help you."

He was silent for a while. You decided not to push him, and waited in anticipation. Finally, he took in a huge breath, exhaled slowly, and said, "It was the demon we ganked tonight... It brought up my mom."

"What did it say?" You run your fingers over his hand softly, knowing that it calms him.

He took another minute before he answered, and you could tell that whatever the thing said, it had really hurt him.

"It said that he enjoyed torching my mom, and... That he had a lot of fun with her down in hell." Dean finally admitted. His hand clenched into a fist, and a vein began popping out of his neck. He bolted out of his chair and to the sink, pouring out the rest of his beer. He threw the bottle into the sink, shattering it. He put his hands on the counter and put his head down, trying to calm himself.

You get up slowly and walk over to him. You lay a hand on his back to see how he would react to your touch. When he didn't do anything, you wrapped your arms around his stomach, hugging him tightly from behind. The two of you stayed like that for a long time. Not saying a word. Not moving. Just being together, letting thoughts wonder and roam.

After a while, he turned around to face you, still in your arms. His eyes and cheeks were red, and tears streaked his face. His emerald green eyes gleamed with sadness. Up until this point, you hadn't seen him cry before.

You wipe his face with your hand. He closed his eyes, comforted by your touch. You rest your hand on the side of his face, feeling so much love for the broken man who stood before you. He buried his head into the crook of your neck. You begin stroking the back of his neck again, this time more soothingly and purposefully. His hands were gripping your hips tightly, because he was afraid that you would leave him. You whisper, "I will always be here for you, Dean. Forever."

His muscles relaxed even more, as if he needed to hear that. He straightens back up and looks into your eyes, brushing your hair back behind your ear.

You smile up at him and say, "Listen to me, Dean Winchester. I will keep you safe. I will be here for you. I will protect you. You understand?"

His eyes light up as he takes in your promises. You could see that he was stunned.

He doesn't say anything, and grabs you into another hug, holding you so close to him that you could hear his heartbeat.

You didn't need him to say anything. His reaction was enough. You knew he had understood and appreciated you. You knew that his whole life has been about protecting people, no matter how close they were to him. You knew that he would give anything up to keep someone safe. You knew that he wondered if anyone would do the same for him, besides his brother. You knew he was lonely, and felt unprotected.

Your words comforted him beyond anything you could ever imagine.

Because that's all that Dean Winchester needs.