This story starts in episode 18 of season 1, when something goes wrong in a small town and kids are sick, including the one you promised to look after–Asher. Two strange men, Dean and Sam Winchester, appear and then you realize life isn’t as black and white as you thought.
Dean x Reader
The bell rings in the motel lobby and Michael gets up to answer
it. You help Asher with the food for supper, since their mother is out and
about at her other job. You don’t mind helping out the boys, in fact, you love
them like little brothers.
“King or two queens?” He asks a little rudely, you think.
A deep voice answers and you pause. “Two queens.”
“Oh, I’m sure.” Michael murmurs. You hear him from the other
“Asher, don’t touch anything yet.” You whisper to him and he
nods, sitting down in his chair to finish watching his cartoons. You walk over
to the lobby and wipe your hands on the knees of your jeans. “Michael, honey.
Don’t smart mouth the guests.” You warn him.
“Ah, he’s okay.” The man smiles. You look up at him and
notice the look in his eyes. He looks friendly enough, but you also know what
comes with that. “Just a kid.”
You place a hand on Michael’s shoulder. “Why don’t you go
finish helping Asher with dinner?” As you say this, you gently push him into
the next room, hoping he will just go with it and leave the guests alone. Their
mom would not be happy to know they left because of Michael’s remarks.
Michael rolls his eyes. “Fine, fine. They want two queens
and maybe a box of—“
“Michael!” You turn around and shoot him a glare. He holds
his hands up and walks into the next room, continuing the dinner you started.
You look back up at the gentleman. “I’m so sorry. He never learned how manners
The man waves his hand in the air and smiles at you. “That’s
alright. Kids will be kids. Yours?”
You laugh and shake your head. “Hell no. I’m just a nanny,
basically. I watch them when their mom has work. So two queens?” You grab a
sheet of paper and jot that down.
“Oh yeah, for me and my brother out there.” He jabs his
thumb to the door. You spot the other man leaning against a car and looking around,
perhaps a little nervously. “Been a long day.”
“I bet.” You glance back to make sure Michael is doing okay.
Of course he is, he didn’t have anyone but his mother until a few weeks ago. He
barely needs you at all, but she was worried sick about them. “Card or cash?”
“Card.” He hands you a credit card and you slide it into the
system. It accepts and you slide his card back to him. He has a blank stare on
his face as he looks passed your shoulder. You glance behind you and see that
Michael and Asher are sharing food, giving each other what they don’t like
because usually, the other one liked it. You glance back at him.
He jumps a little and looks down at you, those apple green
eyes searching yours for a second. He clears his throat. “Sorry, just reminds
me of…” He stops himself and you understand.
“You and your brother?” You ask, shifting your gaze back out
to the man on the car. He’s looking inside now, waiting for his brother to come
back to he can get some shut eye.
The man nods again. “Yeah… Exactly.” He chuckles. “Thanks….”
He trails off and purses his lips.
“Y/N.” You tell him your name and give him a little smile.
It must be hard to go through what Michael and Asher are going through. You
wouldn’t wish it on anyone.
“Dean.” He smiles at you and grabs his card and the keys. “Thank
you.” He motions to the keys and takes a few steps back to the door.
You giggle and wave at him, watching him smile and relax his
shoulders. He can’t be so bad.
“Oh you’re in love.” Michael coos when you walk back over.
You playfully kick his shin and take a seat at the table.
Asher looks at the two of you, confused. “You, eat.” You point to the plate of
chicken nuggets and mashed potatoes on his plate. “Gross.”
“Maybe if you learn to cook.” Michael shrugs and bites into
a chicken piece.
You throw a dish towel at him and he catches it, causing
Asher to laugh hard. You smile, gladly accepting his laughter. Anything to make
these kids laugh makes you happy.
It was awful. Joanna rushed Asher to the hospital this morning
and had to call in sick to her diner shift. You told her you would stay and man
the motel for her, and watch over Michael since he didn’t want to go.
When he finally crawled out of bed, Michael told you he was
going to sit outside until Joanna called and gave news on Asher. You let him,
checking on him every few minutes. Poor thing, he’s had such a bad time lately.
After the call with Joanna asking you to bring some of Asher’s
things and a bag for her, you walk outside with your hands loaded and see Dean
squatting down and talking to Michael with his brother right beside him. They
all look up the moment the door closes.
“Michael, I’m only going to be gone an hour or so. Please
don’t do anything rash while I’m gone.” You look at him.
“I want to come.” Michael stands up and looks up at you,
You sigh and shake your head. “Your mom wants you to stay
here. Denise is covering rooms and all you have to do is turn on the no vacancy
“Please?” Michael’s eyes are glazing over but you know
Joanna’s reasoning for making him stay here.
You hurriedly shove the bags into the car, shaking a little.
You are worried for Asher and Michael. Michael blames himself and worries that
Asher will die because of him. He cried all night, never falling back to sleep.
“Whoa,” Dean walks over and helps you as you try to shove
them in the backseat of your car. “hey, let me drive you. It’s the least I can
do.” He looks down at you, those green eyes searching yours again. You don’t
know what he’s looking for.
He opens the passenger side door for you and you look over
at his brother. “Sam will watch after Michael. You can trust us.” Dean
smiles and nods a little.
Thinking it over quickly, you decide they are better than
half the men in this town. You climb in the seat and let Dean shut the door for
you. He shares a look with his brother before he walks over and gets in,
starting the car up and backing out of the spot.
The ride is silent with nothing but the faint sounds of the
music on the radio. You stare out the window, wishing more than anything that
you would have checked Asher’s room last night, wishing that you could have
saved him, but something does feel off about this whole thing. How exactly did
that healthy little boy get so damn sick?
Dean clears his throat and messes with the air, turning it
up and then down again. You feel his eyes on you as he stops at a light and
shifts in the seat. You can hear the fabric of his jeans scoot against the
leather and it sends a chill down your spine. You raise your head and look over
“What?” You ask plainly.
Dean looks away quickly, noticing the light is green and
drives up to the hospital. “You care so much for these boys and they aren’t
He would wonder about that. Everyone does to the point you
have even told them Michael and Asher are yours just to shut them up. You shrug
your shoulders and play with a piece of skin that’s peeling away from your
nail. “You should have seen them before I came along. Michael was keeping
Asher, playing both mom and dad. He’s so young and his mom can’t keep up with
bills and being their mother. Joanna tries. Two jobs just don’t cut it
sometimes. So one day I came into the motel and asked for a room and Michael
was there, giving me the rundown of the place. I offered to watch him and his
brother until their mom came back and since then… I have been taking care of
“Wow.” Dean turns the wheel and lands perfectly into a
parking spot. He looks over at you and smiles. “You’ve done a great job. Both
“Michael still does most of the work.” You shrug and look up
at him. “I just make sure he stays out of trouble and that Asher….” You trail
off, not wanting to talk about it just yet.
“Come on.” Dean gets out of the car and walks over to your
side, pulling the passenger side open for you to climb out of. For a second,
you pause and wonder how he looks so handsome, acts so perfect, yet he suddenly
finds himself in your life. This, mixed in with all the kids being sick, doesn’t
Dean grabs most of the bags, only letting you carry in the
pillows Joanna asked for. He opens doors for you and even refuses to let you
press the elevator button. He chuckles at your mention of this and just shrugs
it off, though you wonder if he’s really this generous or if he’s the type of
guy to work a lady up until he can sleep with her.
Inside the hospital room, there’s a nurse hooking Asher up
to a few machines. You aren’t good figuring out which machine does what, so you
let the nurse continue her job and turn to Joanna, who is weeping on the couch,
rocking back and forth.
You walk over and put the pillow behind her, kneeling down
so you can look up at her. “Shhh. He’s getting help.” You tell her over and
over again, hoping that will calm her down.
Smoke On The Water echoes around the room and Dean’s hand
flies into his coat pocket after he lets go of the bags and sets them by the
closet. He glances at you, his lips mouthing a ‘sorry’ your way and turns as he
One of the doctors walks in and he checks up on Asher,
checking his sheets and then turning to Joanna. “We’ll what we can.” He assures
You see Dean hang up his phone out of the corner of your
eye. He shoves it a big too harshly in his coat and looks over at the doctor,
his eyes narrowed in on the old man. You tilt your head some, wondering what
all that is about.
“I’ll be back to check in on you in a little while.” The
doctor turns and sees Dean, his eyebrows shooting up and his smile to widen
some. “Ah! Detective, discovered anything yet?”
Did he just say detective?
“You’ll be the first to know when we have.” Dean doesn’t
take his eyes off the old man.
“Who is that?” Joanna looks up and wipes her eyes with a
tissue and runs a shaking hand through her dark hair.
“Dean. He’s staying at the motel and he offered to give me a
ride.” You explain, watching as he stares at the floor. His facial features
have changed somehow, gone dark. You stand up and walk over to him. “What was
He’s gaze shifts to meet yours and he shakes his head, his
lips parted some. “Nothing. I have to run, but let me know how the kid is.
Please?” He looks into your eyes again, making you feel like a special woman.
You suspect he does this a lot.
“Dean, you drove me here. Let me drive you back.” You slip
your fingers into the pocket of his coat and dig around for your keys. You feel
the cool metal touch the tips of your fingers and clamp them around the keys,
pulling them straight out. “Maybe explain to me on the way?”
“I can’t explain this.”
The bell on the front door dings, indicating that someone is
walking into the building. You have been back for a little while, helping
Michael watch over the place and playing cards with him. Coming from such a
poor family, Michael and Asher have very little to do, so they always make up
their own games and have fun any way they possibly can.
“Go get the desk, Michael.” You nudge him to the door and
lay out on the floor, resting your eyes for a moment and listening to the music
softly play in the background.
You don’t pay attention to the voices coming from the lobby
at first, not until you think you hear Michael say something about calling the
cops. Your eyes fly open and you sit bolt upright, looking out the door and
seeing a familiar brown leather jacket leaning across the desk. He doesn’t see
you, but you can tell that by the look on his face, something is seriously wrong.
“Sometimes… nightmares are real.” You hear Dean say as you
walk through the door. When he spots you, he stands up straight and rolls his
shoulders back, eyeing you down as if you just caught him trying to sell candy
to Michael. “Y/N…”
Sam is standing behind Dean, his hands shoved into his coat
pockets and looking around. He catches your eye and he pales a little, quickly
avoiding your stare and he tries to find some interest in a plant over in the
corner of the room.
“What are you telling him?” You dart your eyes between the
two men, wanting an answer now.
“The robed thing I saw, it’s real. He saw it too.” Michael
looks over at you. It’s the nightmare he told you about last night, the one
that woke him up and had him run to you, telling you in gruesome details what
You look over at Dean. “You’re telling him ghost stories?”
“I’m only telling him that the thing he saw is real.” Dean
holds up his hands, spreading his fingers out and the seriousness of his tone
never changing. “Look, he’s in a bit of trouble. We need him.”
“No.” You say quickly.
Michael looks from you to Dean. “You would do anything for
your little brother, right?”
Dean nods his head, his eyes shifting over to Sam for a
split second. “I would. I love him.”
“Then whatever it is, I’ll do it.”
“Michael!” You wrap your fingers around his arm. “No, I
He looks up at you, tears filling those beautiful, big eyes
he has. “He’s my little brother, and I have to make this right.”
Not able to say no that face, you take a long sigh and pinch
the bridge of your nose. “What does he have to do?”
It doesn’t take long for Dean and Sam to explain the
situation to you. As Dean settles Michael in his room, setting up a night
vision camera and making sure he knows the steps to take, Sam goes a little
more in depth with you, making sure you know what you are about to witness.
You decided you wanted to help, not sit back and do nothing.
If Michael is stuck in this, you want to know exactly what’s happening.
“All of them. Real?” You’re sitting on a couch near the boys’
room. Sam checks the laptop and he sucks his bottom lip between his teeth. “Shit…
And here I am, thinking people are the worst.”
“Some of them are.” Sam looks at you.
You look at the camera, seeing how well Dean treats Michael.
He looks at him the way he would any adult, which is exactly what Michael
wants. He’s never wanted to be treated like a kid. There’s just something about
Dean, though. Maybe it’s the way he sits proudly, the cockiness in his voice
any time he talks to you, or that dazzling smile he gives you. “What about him?”
“Dean?” Sam raises an eyebrow and then he chuckles. “He’s an
idiot, but usually he means well.”
Dean gets up and walks into the living room, shutting the
door behind him. He stretches and walks over to the second chair that’s facing
the laptop and leans his head back, far enough that you wonder if it’s about to
snap off. “Man, what a fuckin’ day.” He rubs the back of his neck and sits up a
little, spreading his legs out in front of him.
“Tell me about it.” You don’t want to sit far away and not
able to see Michael. You have to make sure everything is okay. You stand up and
take the few strides over, standing between Sam and Dean as they glue their
eyes to the screen.
You stand there for nearly an hour, watching the screen,
waiting for something to happen. No one says much and nothing but the wind can be
heard outside. Nothing happens, which you can’t tell if that’s a good or bad
Dean looks up at you after a while, blinking several times
after looking at a screen for so long. “Take a seat, doll. We got this.”
“I’m okay.” You say.
You feel warm fingers touch your elbow and guide you over to
the right. Dean pulls you down so you’re sitting on his knee and he keeps his
arm firmly around your waist.
Another couple of hours roll by with nothing happening. It’s
nearing three in the morning and Michael is still staring at the window. You
haven’t moved from Dean’s lap and he hasn’t made you yet. In fact, your
shoulder is pressed to his chest now, comfortably sitting with your arms around
his neck. You can’t remember changing into this position, but you certainly
aren’t going to complain about it.
“Hey,” Sam points to the screen and grabs his gun from the
table. A shadow with long spindly fingers pops up. The twig-like fingers slide
open the glass and Dean taps your thigh, silently telling you to get up before
you are thrown into the floor.
You stand up just in time for the boys to jump to their feet
and rush inside, guns going off almost the second the door is open. You jump,
this being your first time hearing a gun this close. That’s when you realize
you forgot to cover your ears, just as Dean instructed you to do several hours
When the shooting stops, give it a few minutes before you
hear Dean’s panicked voice calling for Sam. You rush into the room to see Sam
on the floor and that creature lying on top of him.
“Hurry!” Michael runs out of the building and rushes over to
his mother. “Where is he? Is he alright?” He asks quickly.
You follow not far behind and see Dean is throwing bags into
the back of his Impala. He glances up and sees you standing there, fingers
through your belt loops. He gives you a warm smile, it’s crooked, but that
makes it even more charming.
“Thank you two for keeping an eye on him.” Joanna looks at
both the boys and smiles brightly at them. “Asher is going better and he’ll get
to come home in a few days.” She shrugs. “It’s some kind of miracle.”
“Can we go see him?” Michael asks, bouncing on the balls of
Joanna giggles and points to her Jeep. “Go, get in and we’ll
Michael excitedly runs over and jumps in the front seat of
the Jeep. He bounces up and down, waiting for his mother.
Joanna waves Sam and Dean off and makes her way over to her
son. It’s nice to see them so happy for once, even with one of them still in
the hospital, this means that everything will be okay soon. It’s a great
“Guess this is goodbye.” Sam looks down at you.
“Does it have to be?” You ask, squinting from the sun as you
look between the two of them. “What you two did was amazing. I want to learn.”
“No.” They say in unison, then give each other a look.
“I’m never going to be able to sleep now, knowing that there
are so many… things out there in the dark. I want to come with you.”
“And what about Michael and Asher?” Dean asks.
“Michael has never needed me. And Joanna says she’s going to
quit the diner job after this anyway, to spend more time with them. I need a
break. Train me to do what you do.”
“This ain’t a picnic in the park.” Dean looks down at you. “This
is serious work. It involves guns and a lot of dirty work.”
“Then teach me.” You know you aren’t giving up, and
something in Dean’s face tells you that he knows that. You two have known each
other for a very, very short time, but all you can think about is riding in the
Impala with him, singing along to songs by day and chasing these creatures at
“Dean, don’t even think about this.” Sam stares at his
brother, open mouthed.
“Just my kinda girl.” Dean smirks and offers you his hand.
Life on the road is great. Leaving the boys, Michael and
Asher, it did hurt a lot, and they were sad to see you leave. You promised you
would come back and see them sometime, when it was a good time. You couldn’t
predict how long you were going to be with the Winchester’s, but you know it
will be quite some time before you return to a normal life—if you can.
It doesn’t take long to learn what these two men are about;
sleeping in motels most days, driving most nights, and stopping at bars along
the way. There is no case that just falls into their laps, they have to
investigate and find any abnormal happenings in the towns they cross through.
In between towns, Dean takes you out, off the road, to learn
how to aim and shoot a gun. You aren’t too comfortable with it at first and he
tells you to take it easy. Guns aren’t for everyone and you certainly feel like
they aren’t for you.
“it’s okay.” He assures you after one particularly stressful
session with the weapon. “Let’s head to the bar and grab a drink, hm?”
Dean leads you through the trees and back to the bar, where
Sam was inside, doing some research. He always has his head stuck in a
newspaper or in his laptop, if there’s internet around. Dean keeps his hand on
the small of your back as you two walk inside and look around, spotting Sammy
just a few tables down.
“Found somethin’ yet?” Dean leans across the table and grabs
the beer that’s sitting beside all of Sam’s work. He takes a long sip of it and
smacks his lips, glancing around the floor.
You slip into the seat beside across from Sam and pull a
newspaper away from him, reading the front cover. It means nothing, really.
Just a dog rescuing a cat or something along those lines. You set the paper
back down and steal the beer from Dean’s hands, taking your own sip and setting
it down on the table. Dean is a drinker, and he will drink all night unless you
pull him away.
“Maybe.” Sam lays out the paper in his hands. “A couple was
found in their home last week. Throats were slit but there were no hand prints
and no signs of a break in. Dean?” He looks up from his paper.
You glance over your shoulder and realize Dean has been
staring down at you this whole time, his eyes wide and his mouth slightly open.
When you turn to face him, he vigorously shakes his head and takes an interest
is something over at the bar. “Go on.” His voice breaks a little.