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What a Long, Strange Trip it’s Been

Summary:

Just as Sam was settling down, just as life was beginning to look normal… that’s when everything happened.
When Jess was taken, when Dean had shown up.
Now they had to start from scratch, take it from the top.
to find what killed Jess and their mother in the most organized way possible.
to make it look as “normal” as it could get.
Let’s call it a road trip.

Notes:

hi! I’m a bit new to the Fan Fiction scene so this fic might be an absolute disaster, or it may come out perfect. I also think I should profess this by saying that this fic takes place during the first season of Supernatual, so if some of the references are outdated or some characters that you enjoy (Castiel, Crowley, etc.) are not present, that is why.

Chapter 1: Prologue

Chapter Text

-LAWRENCE, KANSAS, 20 YEARS AGO-
“Come on, Dean. Let’s wish your brother a goodnight.” Mary Winchester carries her 4 year old son, Dean, cooing to him softly as she crosses the threshold of her youngest son, Sam’s nursery. Her white nightgown brushing the floor like a bride’s dress. “Mommy, it’s cold in here.” Dean’s voice babbles tiredly from where she was sporting him on her hip. “Yeah… that’s weird, isn’t it?” She asks the rhetorical question, the tired Dean just nods and rests his head back against her side as if holding it up for too long was too much work. The baby, Sam, blabbers from his crib as he looks over at his mother and older brother. Mary sets Dean down on the soft plush carpet, much to Dean’s Dismay. However, the sheer sight of Sam immediately melts all negative feelings away from him, and he leans over the crib and presses his lips to his baby brother’s forehead. Mary leans over as well, doing the same before whispering, “goodnight, love.”

“Hey, Dean!” A burly voice calls from the doorway. Dean immediately perks up, recognizing the voice as his father, John. “Daddy!” He cheers, smile evident in his voice. “Little chilly in here, don’t you think?” John explains, a soft chuckle leaving his lips before he turns to the thermostat on the wall. It read 68°F. “Dumb thing must be broken.” He murmurs to himself, giving it a faux angry shove before scooping up Dean. “Let’s get you to bed now, alright, Dean?” He asks, looking down at the boy he’s cradling, but he seems to already be dozing off.

Mary drifts past John, leaving the room, turning to look fondly upon her eldest, then up at John. “You sure you’ve got him?” John just nods as Mary walks down the hallway, cutting a corner and disappearing out of sight. She moved a bit faster than usual, like something was following her. John doesn’t take notice and hugs Dean closer, whispering a quick goodnight to Sam before shutting the door, leaving Sam engulfed in darkness aside from the purple glow of a small nightlight in the corner of his room. The ticking of a coo-coo clock on Sam’s nursery wall gets louder, and louder. Sam watches and babbles on with curiosity. The glow of his nightlight seems to get more intense, as if something in the room was also possessing that light.

Mary stirs madly in her bed. Shuddering with tremors that she’s only experienced when underdressed in the wintertime. She eventually gives up on sleeping and pushes herself upright against the headboard, rubbing her eyes as they adjust to the darkness of the room. The baby monitor on her nightstand shrieks with static before a thick, steady *tick-tocking* noise becomes evident through the speaker. Mary turns, noticing that John isn’t in bed with her. Her stomach flips, she shifts uncomfortably, getting an overwhelmingly bad feeling about all of this. Getting up, Mary tugs nervously at the hem of her nightgown. She inches towards her door and opens it before quickly, and quietly making her way to Sam’s nursery.

Through a crack in the doorway, Mary sees a silhouette standing over her son and she presumes it to be John.
“John?” She calls in a hushed tone, as if not to wake anyone else in the house, including Sam.
The figure turns its head to her, still unable to be seen in the dark room other than a dull, purple aura that emanates from it. It brings a long, slender finger to where it’s lips would be and breathes out a long, harsh.
“Shhh.” Mary, confused but not willing to argue with John turns around with a shrug. The sound of the TV drifts blissfully up the stairs, pulling Mary from her temporary terror. “How many times do I have to tell you John, turn the TV off before you come to bed!” She calls playfully up the stairs before reaching the bottom.

Her eyebrows knit together on her forehead as she realizes that John is here… asleep on an armchair without any idea of the unknown person in Sam’s nursery. Mary is frozen in place for a couple of seconds before turning and bolting up the stairs again, painfully careful her feet don’t catch on her long nightgown.

“Sammy!?” She calls up the stairs and pushes the door of his nursery open with brute force, stopping short when she sees no one there, and Sam fast asleep in his crib. “What?” Mary’s voice drops a few octaves as a chill runs down the length of her spine, hearing deep breathing sounds behind her. She ignores it, it’s probably just the house settling, after all. gently picking up Sam, Mary spins around quickly, overly ready to bolt directly out of this god forsaken room.

She stutter steps as she comes face to face with the thing that had been terrorizing her for weeks. It places its hand over her head before she can shriek, but it seemed to have forgotten the baby. Sam stirs in his mothers arms as he feels her go completely stiff. Whatever this creature was startled him to no end and he wails, screams and squirms in her arms.

John sits upright in his armchair hearing Sam howl from upstairs. “Sammy?” He calls. “Just a second, bud!” He shouts again before getting to his feet lazily and moving as quickly as he can up the stairs and into Sam’s nursery where he finds his wife physically frozen, choking and gasping for air with Sam in hand.
“Mary?”
He chokes out, completely confused as to what he was witnessing.
“Mary! Come on, wake up!” John pries Sam away from her and watches as she crumples on impact, as if the sheer taking of Sam destroyed whatever life was left in her. Just as John bends over his lifeless wife, a small flame is set to the hem of her nightgown.
Dean gently knocks on the door, causing it to open slightly.

“Daddy?” Dean asks sleepily as he assesses the situation.

“Listen Dean, I need you to take Sammy outside as fast as you can. I’ll be out in a second..” Dean, eager to follow his father’s instructions nods and shuffles as quickly as his little legs could go.

John notices the flame and his eyes widen, trying to stomp it out as quickly as he can, but it doesn’t seem to extinguish. “What the hell..” John murmurs to himself, his eyebrows furrowing as he stomps harder.
The flame grows, engulfing Mary, and whatever was left of Sam’s crib
“No!” John barks as he stumbles backwards, willing to do anything to try and retrieve mary, but he knows deep down there was no use now.

He makes his escape, finding Dean carrying Sam outside. looking up through Sam’s window, the crackle of the fire can be heard from down here and the curtains whip wildly from the window, allowing the outside to view the harsh orange and gold hues bursting from inside.

-STANFORD UNIVERSITY 20 YEARS LATER-
“Come on, Sam! Just come to this one thing with me. You barely get out of this apartment.” Jessica whines. Her eyelashes flutter as she looks at Sam peeking around the doorframe behind her in the mirror of her vanity. “You know how I feel about Halloween, Jess.” He replies, letting himself step out from behind the doorway. “It’ll be fun!” Jess adjusts the hat of her poorly made nurse costume in the mirror before getting up and spinning around elegantly to face her boyfriend. “You already agreed, and where’s your costume!” She nags playfully. Sam lets out a soft chuckle and shoves his hands in the pockets of his heavy pleather jacket. “I haven’t worn a Halloween costume since I was 5.” He replies, his face twisting into a look that screamed ‘are you serious?’ “You’re impossible.” Jess shakes her head, her wavy blonde hair fanning over her shoulders as she rolls her eyes.

Sam walks behind Jess as she pushes open the heavy wooden door to a run-down bar just off the side of the road. “You’re sure this is where this big ‘party’ is at?” Sam asks warily Jess flashes him a look over her shoulder that told him to stop worrying about everything. “Got it…” Sam replies, nodding his head as he forces his lips into a tight line.

The look of the bar was like any other. Gross, dark wood tables and seats with the seat covers peeling back scattered haphazardly across the floor, lights flashed from overhead and music blared from every direction. It looked like the furniture in this place was picked up at an estate sale. The smell of cigarette smoke infiltrated Sam’s nostrils immediately and he chokes back a cough.

“Here’s to Sam!” Jess’s voice booms proudly as Sam collects himself from the attack on his senses that was this bar. Jess hands Sam a shot glass full of an unnamed liquid. “And his awesome LSAT score… trust me… he’s going places.” Jess explains, beaming with pride that her boyfriend can’t even stomach. “Oh.. it’s not that big of a deal.” Sam raises his glass lazily as everyone clinks with him. “Quit trying to act all humble. You know your score was scary good.” Sam seems more worried about the hair at the nape of his neck, messing with it and avoiding eye contact. “So… you’re like… the golden boy of your family, huh? How’s it feel?” A boy from across the table asks, his head animatedly tilting to one side. “Oh, my family doesn’t really know.” Sam shrugs, taking a sip from the beer bottle he actually paid for. “What? No way. Stop lying dude, trying to remain humble for so long is gonna get boring.” The boy explains, clearly not buying whatever story he thinks Sam is trying to sell. “I mean, we’re not exactly a picket fence family, y’know. Enough about that, anyways. I have an interview on Monday. I hope it goes well, they say I might have a real shot at a full ride.” Sam gives a smile, changing the subject swiftly before it becomes too uncomfortable for him. The boy scoots back on his chair, causing it to scream beneath him as he goes back up to the bar for more rounds.

“In all seriousness, Sam, I’m proud of you. You’re gonna kill it on Monday.” Jess tugs him in by the collar of his plaid button up and he gives her one of his many forms of awkward smile. “I hope so.” He lets his voice drop a few octaves before pressing a quick peck to Jess’s lips. “I know so.” She replies, flashing him a reassuring smile before letting go of his shirt and turning to talk to one of her other friends.

It had been a long night, and as soon as Sam and Jess had gotten home from their outing, they immediately passed out in bed. It was a nice, calm October night one of the many Sam was getting used to.

or… one of the many Sam THOUGHT he was getting used to. Just as his body was beginning to truly relax
*Clatter*
Sam’s eyes shoot open, his body stiffening as he realizes he’s just heard a window open in the other room. Jess shifts beside him, allowing him to easily slide away from the bed without bothering her.

He crosses the threshold of their bedroom into the kitchen, the curtains from one of the two windows available were strung ajar from the breeze showing Sam that the window he could have sworn he shut earlier had been open as far as it could go. He hears the creeks of the floorboards while he isn’t moving. Footsteps getting closer. He ducks behind a cabinet before the man enters the room. It’s dark aside from the light cast on the ground by the full moon outside.

Sam waits patiently like a puma waiting to pounce. As soon as the man gets close enough Sam lunges forward, grabbing the man by his shoulders. He could feel the cold leather of the man’s jacket beneath his hands as the man aims a strike at Sam’s elbow, knocking his arm away from the man’s shoulder. He then aims a quick jab at Sam, Sam ducks quickly out of the way coming back up, ready to throw a punch before the man grabs Sam’s arm and swings him around shoving him backwards. Sam uses his legs to kick at the man to which both attempts are blocked easily.
“*Who the hell is this?*”
Sam thinks to himself as his heart rate increases, and not just because he’s fighting. Panting, Sam lays one more Hail Mary into the man, the man catches his arms and shoves him to the ground, pinning him successfully as the light catches both of their faces.

“Dean?” Sam asks in horror and confusion. Dean, hysterically laughing at something that Sam clearly did not find funny in the slightest, lets go of Sam’s arms, allowing him to shove his shaggy fringe out of his face to get a better look at his brother.
“This isn’t funny dude you scared the crap outta me!” Sam’s eyebrows were furrowed and set heavy on his forehead, showing Dean just how serious he felt about the matter.
“I think you mean.. you’re scared. I could tell you were getting a bit tired there.” Dean scrunches his nose, teasing his brother like no time had passed between them at all.
Sam grabs deans arm and twists it, bringing his heel up to kick him over and pin him to the hardwood beneath him, still panting.
“Maybe I was wrong…” Dean murmurs under his breath. “Now get off of me.” Dean demands. Sam rolls off and pushes himself to his feet, holding his hand out to help Dean up.
“What the hell do you think you’re doing here, Dean.” Sam crosses his arms, his eyebrows haven’t relaxed since he woke up. “Well I was lookin’ for a beer.” Dean gives him a sarcastic, tight lipped smile before grabbing Sam’s shoulders and squeezing quickly before pushing past him.
“I’m serious, Dean. What the hell are you doing here?”
“Alright, okay. Yeah. We gotta talk, Sammy.” Dean replies, turning to face him again. Sam is giving him a look of utter disbelief. “We both have phones you jerk.” He huffs out his nose like an angry Bull. “If I would have called… would you have picked up?” Dean replies, his quick wit clearly knocking Sam down a few pegs.

“Sam.. is that you?” Jess flicks the light on, tugging at her boy-shorts before looking up. The sight of the two boys clearly pulls her right from sleep as her eyes go wide immediately. Sam looks discouraged, like he could have gone without having this conversation with Dean right now, but considering he has to, he wipes a hand over his face and steps aside. “Dean, this is my girlfriend Jessica.” Sam tries to ignore the way Dean rakes his eyes over his girlfriend. He seemed to have a habit of doing that. “Hey, wait, your brother Dean?” Jess’s face scrunches up in confusion, her eyes set on Dean, flashing him a soft smile before flicking back over to Sam. Sam nods in return, his hair slightly flopping into his eyes. Dean steps forward causing his boots to clink rhythmically against the floor. “Y’know… I gotta tell you… Jess. You are way out of my brother’s league.” Dean explains, ignoring his brother’s indifference.
Jess gives a soft pity laugh as she backs up “let me.. go put something on.” She swipes her hair over to one side, messing with it instead of looking at Dean.
“Oh no, there’s no need for that. Seriously.” Dean spins on his boot heels to face Sam, who’s already giving him an unamused look. “Uh… listen, I gotta borrow your boyfriend for a second… got some… family business we need to discuss.” Dean pauses, turning back around and gesturing to his brother. “It’s very private stuff.”
Jess nods, seeming to be perfectly okay with leaving the two alone to talk about whatever they need to talk about. “Sure.” She backs out of the room and disappears behind the doorframe and down the hallway.

Dean plucks Sam up by the collar of his shirt and pulls him out into the apartment stairwell. “Cmon’ Dean, really? I’m not 10 you can let me follow you without dragging me like a dog.” Sam grumbles as Dean lets his collar go.
“Listen, dad’s on a hunting trip and he hasn’t been home in a few days. He hasn’t called, texted, nothing. I need you to help me.”
“Dean, you can’t break in in the middle of the night and expect me to just pack up and hit the road. I have a life here.” Sam puffs out a dry laugh, crossing his arms as a draft from the upstairs blows through, causing the two to quiver a bit. “What so you wanna live some apple pie life. Be normal all of a sudden?” Dean’s eyebrows knit together as if he’s never even stomached the idea of trying to be normal after their mother died. “I swore I was done hunting. Im not trying to be normal. I’m playing it safe.” Sam explains. He gestures inside. “I have an interview on Monday, dad told me that if I was gonna go.. I should stay gone. Maybe you should find him. He would want you, not me.”

Sam turns, the socks on his feet making it easy for him to glide back inside.
The warmth of the apartment hugged him quickly, but already he felt weird. A shiver runs down his spine as he looks back the hallway. A bright purple glow bounced off the walls of his bedroom, and he can feel a heavy, cold draft emanating from there. He walks back the hallway hesitantly, trying to ignore the sound of his blood pumping in his ears.

“Jess?”
He calls quickly, his feet picking up their pace when she doesn’t respond.
“Jess?!”
He barks out again as he pushes the door open. The glow dissipates and there lays Jess. Frozen in place, choking on air. Sam rushes over.
“Jess? Hey. Wake up.”
Sam shakes her, but it’s like a force is trying to keep him away from her, and her body goes limp. He shakes her again.
“Jess? Jessica. Hey!”
He steps back just as a small flame starts at the edge of their bed and grows rapidly
“No..!” He howls. Dean rushes through the door, skidding to a halt as the red and orange glow of the fire swallows what’s left of Jessica.

“Come on Sam!”
Dean announces, pulling him back and shoving him out the door with his body, Sam puts up a fight as long as Dean lets him, which was pretty long considering how unassumingly strong Sam was despite his appearance.

The fire department came pretty quickly, it wasn’t long until the fire was extinguished Dean spoke to a few officers and firefighters but after that, he walks back to find Sam staring down into the trunk of Dean’s Chevrolet Impala. Dean’s eyes flash between his brother’s mask of anger and vengeance and the shotgun he’d just tossed into the trunk.
“Let’s get this show on the road.”
Sam growls, slamming the hood of the trunk down, and getting into the passenger seat.