Shelby Winchester's Backstory...

By Ziehmer28

56.7K 1.4K 85

What if Dean and Sam had a sister? When Dean, Sam, and there little sister Shelby were kids Shelby was taking... More

Pilot Pt. 1
Pilot Pt. 2
Sister Pt. 1
Sister Pt. 2
Family Ghost Pt. 1
Family Ghost Pt. 2
Sammy! Pt. 1
Sammy Pt. 2
Sammy! Pt. 3
Sammy Pt. 4
Wendigo Pt. 1
Wendigo Pt. 2
Wendigo Pt. 3
Dead In The Water Pt. 1
Dead In The Water Pt. 2
Dead In The Water Pt. 3
Phantom Traveler Pt. 1
Phantom Traveler Pt. 2
phantom traveler Pt. 3
Bloody Mary Pt. 1
Bloody Mary Pt. 2
Bloody Mary Pt. 3
Skin Pt. 1
Skin Pt. 2
Skin Pt. 3
Hook Man Pt. 1
Hook Man Pt. 2
Hook Man Pt. 3
Bugs Pt. 1
Bugs Pt. 2
Home Pt. 1
Home Pt. 2
Home Pt. 3
Asylum Pt. 1
Asylum Pt. 2
Aslum Pt. 3
Scarcrow Pt.1
Scarecrow Pt. 2
Scarecrow Pt. 3
Faith Pt.1
Faith Pt. 2
Faith Pt. 3
Route 666 Pt. 2
Route 666 Pt. 3
Nightmare Pt. 1
Nightmare Pt. 2
Nightmare Pt. 3
The Benders Pt. 1
The Benders Pt. 2
The Benders Pt. 3
Shadow Pt. 1
Shadow Pt. 2
Shadow Pt. 3
Hell House Pt. 1
Hell House Pt. 2
Hell House Pt. 3
Something Wicked Pt. 1
Something Wicked Pt. 2
Something Wicked Pt. 3
Dead Man's Blood Pt. 1
Dead Man's Blood Pt. 2
Dead Man's Blood Pt. 3
The Truth and The Consequences Pt. 1
The Lie and The Consequences Pt. 2
Salvation Pt. 1
Salvation Pt. 2
Devil's Trap Pt. 1
Devil's Trap Pt. 2
Devil's Trap Pt. 3
Discontinuing Story.... Sort of?

Rout 666 Pt. 1

389 15 0
By Ziehmer28

Shelby

Sam is standing next to Dean's car, looking at a map that is laid out on top of the car while I lean on the car next to him. Dean is on the phone talking to who knows who. "Ok, I think I found a way we can bypass that construction just east of here. We might even make Pennsylvania faster than we thought" Sam said. "Yeah, well if I was driving then maybe we could get there even faster" I said. Dean lowered his phone and looking thoughtfu0 "yeah, problem is, we're not going to Pennsylvania" Dean said "we what" Sam asked?

"I just got a call from an, uh, old friend. Her father was killed last night, think it might be our kind of thing" Dean said. "An "old friend"" I said "believe me, she never woulda called, never, if she didn't need us" Dean says and gets into the Impala "come on, are you coming or not" Dean says to us. I sigh and throw my jacket in the backseat before getting in myself while Sam gets in the passenger seat.

We cruise down the road, fields on one side, a lake on the other "by old friend you mean" Sam started "a friend that's not new" Dean says as he drives. "And by not new friend you mean hooked up with someone" I said in the backseat and Dean glared at me threw the review mirror. "Anyway, so her name's Cassie huh? You never mentioned her" Sam said "didn't I"? There was a long pause as Sam looks at Dean expectantly "yeah, we went out" Dean said.

"You mean you dated somebody, for more than one night" Sam asks "and you didn't tell m, where was I when all of this was happening" I asked poking my head into the front seat. "Hell" Dean said and I nodded "am I speaking a language you're not getting here? Dad and I were working a job in Ohio, she was finishing up college. We went out for a coupla weeks" Dean said to Sam. "And" Sam asked making Dean shrug slightly "look, it's terrible about her dad, but it kinda sounds like a standard car accident. I'm not seeing how it fits with what we do. Which by the way, how does she know what we do" Sam asked?

Dean is silent "you told her. You told her, the secret, our big family rule number one. We do what we do and we shut up about it. For a year and a half I do nothing but lie to Jessica, and you go out with this chick in Ohio a coupla times and you tell her everything" Sam asks mad. Dean just stairs straight ahead "Dean" Sam says mad "yeah, looks like" Dean said and continues staring ahead and put's his foot down. I roll my eyes and slump into the backseat. "For your sake, sh better be nice" I said.

We head into an office to see two men talking to a girl. "Jimmy, you're too close to this. Those guys were friends of yours. Again, Cassie, I'm very sorry for your loss" a guy says and leaves the girl that I was guessing was Cassie. She sighs and turns around, looking straight at Dean. She looks slightly apprehensive, Dean nods at her and grins. "Dean" she says in a soft voice "hey Cassie" Dean says. They stare at each other for a long moment, not speaking. Sam and I watch smiling to ourselves. I clear my throut pulling Dean out of his thoughts.

"Um, this my brother Sam and my sister Shelby" Dean says and Cassie smiles at us and we smile back at her. Her gaze returns to Dean "sorry bout your dad" Dean says to her "yeah, me too" she says and they keep staring at each other. We head to Cassie's house and sit in the lounge room. Cassie carries in a tray of tea and cups "my mothers in pretty bad shape. I've been staying with her. I wish she wouldn't go off by herself. She's been so nervous and frightened. She was worried about dad" Cassie said.

"Why" dean asked as Cassie pours some tea "he was scared. He was seeing things" Cassie said "like what" Dean asked "he swore he saw an awful-looking black truck following him". "A truck, who was the driver" I asked as she hands us a cup of tea "he didn't talk about a driver. Just the truck. He said it would appear and disappear. And, in the accident, Dad's car was dented, like it had been slammed into by something big" Cassie said.

"Now you're sure this dent wasn't there before" Sam asks? Dean and I look at the tea before setting in on a side table. "He sold cars, always drove a new one. There wasn't a scratch on that thing. It had rained hard that night. There was mud everywhere. There was a distinct set of muddy tracks leading from dad's car, leading right to the edge, where he went over" Cassie says and bows her head, getting her emotions under control. "One set of tracks, his" Cassie said.

"The first was a friend of your fathers" Dean asked "best friend, Clayton Soames. They owned the car dealership together. Same thing. Dent, no Tracks. And the cops said exactly what they said about dad. He "lost control of his car"". "Can you think of any reason why your father and his partner might be targets" I asked? "No" Cassie says "and you think this vanishing truck ran them off the road" Sam said.

"When you say it aloud like that, listen, I'm a little skeptical about this ghost stuff or whatever it is you guys are into" Cassie says. Dean huffs "skeptical. If I remember, I think you said I was nuts" Dean says "that was then" she says and they stare at each other again. "I just know that I can't explain what happened up there, so I called you" Cassie says. The sound of a door opening, a middle aged woman enters. Sam, Dean, and I rise to our feet as Cassie goes to take her mom's arm. "Mom, where have you been I was so" Cassie starts.

"I had no idea you'd invited friends over" Her mother stops Cassie. "Mom, this is Dean, a, friend of mine from, college. And his brother Sam and his sister Shelby "well I won't interrupt you" Cassie's mother says. "Mrs Robinson, we're sorry for your loss. We'd like to talk to you for a minute if you don't mind" Dean says. "I'm really not up for that right now" she says and leaves the room. The next day we end up going to a filed where another accident has happen.

"Close the main road, the only road in and out of town? Accidents do happen Cassie, and that's what they are. Accidents" the mayor says as Dean, Sam, and I approach and stand behind Cassie. "Did the cops check for additional denting on Jimmy's car, see if it was pushed" Dean asks? Mayor looks at Cassie "who is this" "Dean, Sam, and Shelby Winchester. Family friends, this is Mayor Harold Todd" Cassie says. "There's one set of tire tracks. One, doesn't point to foul play" the mayor says "mayor, the police and town officials take their cues from you. If you're indifferent about" Cassie starts "indifferent" the mayor says.

"Would you close the road if the victims were white" Cassie asks "you suggesting I'm racist Cassie? I'm the last person you should talk to like that" the mayor says "and why is that" Cassie asks? "Why don't you ask your mother" the mayor says and walks away, leaving us standing in the field. Sam, Dean, and I head back to the hotel that we're staying at and Sam and Dean get some suites. Sam is in trousers, shirt and tie, picking up a suit jacket while Dean fixes his tie in the mirror. I walk out of the bathroom, wearing black pants, black boots, a purple shirt while a black button up jacket is over it.

"I'll say this for her, she's fearless" Sam said "Mmhmm" Dean says and Sam looks at me and we both grin. "Bet she kicked your ass a coupla times" I say as I sit on the bed "what's interesting is you guys never really look at each other at the same time. You look at her when she's not looking, she checks you out when you look away. It's just a, just an interesting observation in a, you know, observationally interesting way" Sam says. "You think we might have more pressing issues here" Dean asks and looks at Sam.

"Hey, if I'm hitting a nerve" Sam says "lets go" Dean says and turns away. "I think you did hit a nerve" I said to Sam who laughs. We head to the docks and walk down a pier, a few people are fishing. We approach two older men having lunch "excuse me. Are you Ron Stubbins" Sam asks and one man nods. "You were friends with Jimmy Anderson" Dean asked? "We're Mr Anderson's insurance company, we're just here to dot 'I's' and cross 'T's'" Dean says.

"We were just wondering, had the deceased mentioned any unusual recent experiences" I asked? "What do you mean, unusual" Rom asks "well visions, halluinations" I say "it's part of a medical examination kind of thing. All very standard" Dean says "what company did you say you were with" Ron asked? "All National Mutual. Tell me, did he ever mention seeing a truck? A big black truck" Dean asked "what the hell you talking about? You even speaking English" Ron asks? Ron's friend speaks "son this truck, a big scary monster looking thing" he asks?

"Yeah actually, I think so" Dean says and Ron's friend nods "what" I ask "I have heard of a truck like that" the man says. "You have, where" Sam asks "not where, when. Back in the '60s there was a string of deaths. Black men. Story goes, they disappeared in a big, nasty, black truck" the man says. "They ever catch the guy who did it" Dean asked "never found him. Hell, not sure they even really looked. See there was a time, this town wasn't too friendly to all it's citizens" Ron's friend said. "Thank you" Sam says and we make our way back down the pier to the Impala.

"Truck" Dean says "keeps coming up doesn't it" I say "you know, I was thinking. You heard of the flying dutchman" Dean asks "yeah, Pirates Of The Caribbean" I said "well, it's a ghost ship, infused with the Captain's evil spirit. It was basically part of him" Sam said and Dean nos. "So what if we're dealing with the same thing? You know, a phantom truck, an extension of some bastard's ghost, re-enacting past crimes" Dean says. "The victims have all been black men" Sam says.

"I think it's more than that, they all seem connected to Cassie and her family" Dean said. "All right well, you work that angle, go talk to her" Sam said "yeah I will" Dean says. "Oh, and you might also wanna mention that other thing" I say and Sam smiles. We stop "what other thing" Dean asks and I look at Sam "the serious, unfinished business" Sam asks? Dean remains silent as Sam laughs "Dean, what is going on between you two" Sam asks?

"All right, so maybe we were a little bit more involved than I said" Dean says and Sam stars at Dean, waiting for his next answer "ok, a lot more. Maybe, and I told her our secret, about what we do. And I shouldn't have" Dean said "ah look man, everybody's gotta open up to someone sometime" Sam says. "Yeah I don't, it was stupid to get that close. I mean, look how it ended" Dean said and Sam and I smile at Dean "would you two stop" Dean says. Sam and I keep staring and smiling "blink or something" Dean says to us.

"You loved her" I said "oh god" Dean says and turns to the Impala. "You were in love with her, but you dumped her" Sam says and Dean is silent. He stares at the ground, glances at Sam and I, then looks back to the ground. "Wait, she dumped you" I said "get in the car" Dean says and he gets in himself "get in the car" Dean say again, mad. He heads to Cassie's but not before dropping off Sam and I at the hotel. "How much do you think Dean and Cassie are kissing right now" I told Sam.

"Well, that's not what I wanted to picture" Sam said with a laugh. "So, what about you" I asked Sam and he looked at me confused. "Do you have anyone besides Jessica that you really loved" I asked sitting on the bed and taking my jacket off. "No, not really, just Jessica" Sam said "you"? "You mean besides the guy who tried to kill me" I asked referring to Trevor. Sam laugh and so did I "no, not really, I mean there's guys that I've liked in my lifetime but never got as series as I was with Trevor" I said.

"I've never heard you fully talk about him, what was he like, I mean when he wasn't trying to kill you" Sam asked breaking into a smile. "He was nice, sweet, cared so much about me" I said. "Did you ever tell him our secret" Sam asked "he knew, I had met him on a case so he knew. I wish I could of told him more but now I'm just happy I didn't" I said. Sam nodded and started to grab his clothes to get changed "hey Sam" I said and he stopped and looked at me "why don't you ever ask me about hell, I mean, Dean use to, aren't you curious" I asked curious. "I'm dame curious, but your not talking about hell and I'm not pushing" Sam said.

I smiled to him and he smiled back before heading into the bathroom to change while I did the same before going to bed.

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