Hindsight: A Supernatural Fanfiction

By: Storychan

Summary: Cas sees how depressed Dean is. He can't change the tragic past, but he can change who was there to witness it, and maybe that will change the future. This is how an ordinary girl winds up thrown into the world of Supernatural – she knows every bad thing that is about to happen to the Winchesters. She can't tell them what the future holds. But the bigger question is, can she stop it? Hindsight is 20/20, and Kelley sees all, even if she doesn't want to. Dean x OC. Self-insert.

Chapter 1

Castiel's POV – Takes place directly after the events of 9x10 "Road Trip":

"Come on man, can't you see, I'm poison. People get close to me they get killed, or worse. I tell myself I help more people than I hurt and I tell myself that I'm doing it all for the right reasons and I believe that. But I can't - I won't drag anyone anybody into the muck with me - not anymore."

That was the last thing Castiel heard Dean say before Sam told him to "just go", before he just….left. Dean just got in his car and drove away, leaving Cas and Sam by the side of the road, surprised, but not surprised at the same time.

Cas felt he should have seen this coming. Dean had always tended to blame himself for things, even if they weren't his fault. Cas didn't think everything that had happened recently was all Dean's fault, at least. Some of the blame fell at Cas' own feet. He was the one who had caused all the angels to fall to Earth. Not Dean.

It was his fault, then, not Dean's, that the angel Gadreel had appeared when Dean prayed for somebody to save his brother's life. His fault that Gadreel had tricked Dean into letting him possess Sam. His fault that Gadreel had turned out to be working for their enemy, had killed their friend Kevin and then took off in Sam's body, leaving Dean with nothing.

They'd exorcised Gadreel from Sam, finally, but by now the damage was done. Sam couldn't trust Dean anymore, and Dean couldn't forgive himself for letting this happen.

But Dean still couldn't just….leave, could he? Just decide that he didn't deserve to be around people, and cut his ties with everyone?

"He's going to come back, right?" Cas asked aloud, turning to Sam and coming back to reality.

"I don't care," Sam snapped in reply, then turned away.

"I can see that you are angry with your brother," Cas noted. "But when has separating ever worked out for us before? You can't just let him punish himself like this."

"Dean can do whatever the hell he wants, Cas," Sam insisted. "But me? I'm not going to waste my time worrying about him. I'm going to go back to the Men Of Letters library and work on finding a weapon that can kill Gadreel once and for all. I'm more worried about the fact that he's still out there than I am about this little….I don't know…tantrum, or mental breakdown, or whatever, that Dean is having. You can help me, or you can leave. What's it going to be?"

Cas frowned. He had looked down on Sam and Dean from Heaven long before he'd actually met them in person. He knew they fought all the time now, but he also knew that it hadn't always been this way. Those two boys, at one point, had trusted each other more than anything else. But right around the time Cas had come into the picture, everything changed. Dean spent a year in Hell. Sam sought comfort with a demon woman and became addicted to the power he gained from consuming her blood. Both boys had become….darker. And though Sam had been cured of his blood addiction, and Dean had stopped having nightmares about Hell, years ago now, the boys had never regained the relationship they once had.

Or, had it even been perfect before that? If Cas had to pinpoint it, Dean's breakdown into a person who was just….done with life had begun years before that, when his father, John, had sacrificed himself to save him. Dean had blamed himself, and undergone radical emotional change. He'd even taken a tire iron to his beloved '67 Chevy Impala.

Yes, Castiel realized. Dean had been a mess for quite some time now. When given the option, a year after John's death, to die in order to save Sam, Dean had jumped at it so eagerly, as if he didn't enjoy the thought of living another year. Dean had such low self-esteem that he believed his own life was worth nothing, that if he were to give up his life, it wouldn't have mattered much in the grand scheme of things.

He had been very wrong. Castiel was proof of that. God had sent him to bring Dean back from the dead after the aforementioned sacrifice had proved unavoidable. Dean had a destiny, or so his Father had told him. He was going to be the vessel for Cas' older brother, the Archangel Michael, and he would then defeat Lucifer in battle and bring about the End Times.

But Dean had said "screw that", and proceeded to save the world, on his own terms. Things had seemed so simple back then. The enemy was clear, as was the quest. But now? They were dealing with angelic civil war, working with demons to further their objectives and wondering, constantly, if the ends justified the means.

Dean couldn't stand it. If he couldn't stand John's death, Sam's death, or his own destiny, he certainly couldn't stand what they were dealing with now. When Cas looked into Dean's soul, he saw a man who had seen enough battles and enough death. A man who would rather be alone than watch another friend die.

But we need him, Cas realized. We need him to be strong, to be able to pull himself together and keep fighting before my brothers end the world with their squabbling…again. But as it stands now, Dean will not speak to, or trust, Sam or I. And we're the only people in his life who are still alive.

Then Cas remembered something. He remembered how he had sent Dean back to the 1970s once, to meet younger versions of his parents, Mary and John Winchester, before Dean was even a glimmer in their eye. He hadn't allowed Dean to change the past, or to prevent the demon Azazel from making a deal with Mary that would eventually lead to her tragic demise in 1983. Changing the past could lead to nightmarish butterfly effects, and as an angel Cas couldn't allow it.

So, he figured, he couldn't go back and stop Dean from losing John, from dying to spare Sam's life, or to stop any of the other tragic things that had led Dean into the depression he was sinking into today.

But, Cas recognized, even though I cannot change these destined events, I can find a way to make them more bearable for Dean. What if there was another person in his life, besides Sam or I? Someone who had never betrayed him. Someone he would never betray.

What if putting one more person into Dean's story….could change how the story ends?

Kelley's POV – Somewhere in Appalachia

Hey. I'm Kelley. I'm your average Supernatural fangirl. OK, maybe I'm an above-average Supernatural fangirl. Not only have I watched every episode of every season of the show, I've also read all the tie-in novels and the comic books and seen the anime adaptation. I have two official merchandise shirts and an unofficial anti-demonic-possession sigil necklace that, around here, keeps getting me mistaken for a Satanist (Not that I mind – Freaking judgmental old people out is fun). So it's no surprise that on a Monday night, instead of doing my homework like I really should be, I was texting my friend about how much I love Dean Winchester.

I don't ship Destiel tho, I told her. Or Wincest. I guess that makes me weird in this fandom.

Who DO you ship with Dean, then? My friend replied. Before I could reply, she sent me another message. Let me guess: Dean x Yourself! You wish that you lived in that world, don't you?

I blushed. Shut up lol, I texted back. I get that he's fictional.

But you want him anyway, don't you? My friend teased.

Well… I thought for a minute about how to explain this. It's just…Dean's been through so much. I just want to hug him and tell him everything's ok.

You say you get he's fictional, my friend pointed out. But the way you talk about him, it's just like you care about him, like a real person.

I shook my head. Come on lol. It's not like that. I know the difference between fantasy and reality. I'm not Becky haha.

I was about to remind my friend of the hilariously meta episode that introduced Becky, the Wincest fangirl parody that reminded me so much of some of the sillier fans I found on . But then I heard a loud thud from my living room.

Son of a bitch, I thought. Did my roommates break something?

I set down my phone and left my room for the living room, prepared to give the girls I lived with at my college a piece of my mind. But when I stepped into the room, I found that nobody was there. However, the TV was slightly crooked.

Did it fall over? I wondered. I walked over to it and grabbed it, trying to put it back where it was. But then suddenly it….shocked me. I looked more closely at it, and that was when I saw something I couldn't explain. I knew that the TV was off…but a picture was displayed onscreen anyway, of a cluster of buildings I didn't recognize.

What…..the hell?! I thought to myself, then reached out a hand to touch the screen. My hand went straight through it! In shock, I dropped the edge of the TV, which I'd been supporting with my other hand. Then suddenly I found myself falling forward… "Whoa…what's happening?!"

Suddenly I was falling, like Alice down the rabbit hole. Then, everything went black.

I woke up to sunlight radiating at my eyelids.

What a weird dream, I thought groggily. I thought I was….falling through my TV?

That's it, I told myself. I need to stop watching weird shows before bed.

Now, it's time for me to open my eyes and try to get ready for math class without waking up my roommate, just like every day.

But when I opened my eyes, I wasn't in my bed, in my dorm. I wasn't even indoors. I was outside, lying on a park bench beneath a shady tree. "Where am I?" I muttered. Had one of my friends taken me out of my bed and dropped me in the middle of campus as a prank?

But when I sat up, I saw that this wasn't my campus at all. It was definitely a college campus, but not one I could ever recall seeing before. "Where am I?" I cried again, this time getting really scared. A newspaper blew into my face on some capricious wind, and the first thing I saw was the date: October 31, 2005.

"That's….not possible," I told myself. This had to be the set-up for an elaborate joke, right? "Seriously, what is this?"

It was then that I heard a feminine voice behind me. "It's Halloween! What's the matter, are you drunk or something?" I heard a trilling laugh. "It's ok. I'm about to go do some drinking myself. I think that's what everyone here at Stanford is planning on doing tonight."

"Stanford?" I repeated. "Like, the university? In California?"

"Wow, you must be really out of it," the voice replied. "Do you need me to help you back to your dorm? I mean, you're a student here, too, right?"

"No, I…." I finally looked at the woman who was speaking to me. When I did, my heart almost stopped. Wavy, beach-blonde hair. Tanned skin. And a sexy nurse costume. This woman looked exactly like Jessica, Sam Winchester's girlfriend, looked in the pilot episode of Supernatural, in the scene where she was…..Going drinking with Sam. On October 31st. At Stanford.

No, there's no way. I thought. It can't be. Maybe she's a Supernatural fan, cosplaying Jessica. That would make sense…right? But why would there be a cosplayer here? Why was I here? And how was I supposed to explain the newspaper, that claimed the year was 2005 instead of 2014? A misprint?

Then I looked at the other buildings in the area, behind this woman who…..couldn't be Jessica, right? Of course she couldn't. Jessica was a fictional character. Supernatural was just a show on…

TV! Suddenly, I remembered the dream (It had to be a dream, right?) that I'd had about falling through my TV. I remembered on the screen had been buildings. The buildings I was standing in front of now looked exactly like those buildings.

"But…..this is…."

"Hey, Jess!" I heard a male voice call, and then I turned around and saw….What? Was that Jared Padalecki, the actor who played Sam Winchester on Supernatural?! No way! What could he be doing here?

"Jess, who's this girl?" he asked. "Is she a friend of yours?"

He was calling the woman Jess. As in, Jessica. Was this a live reenactment of the pilot episode? Some sort of promotional performance art? Why would Jared….

But then I realized….no, the man standing in front of me couldn't be Jared. Jared's hair was long and fluffy, and from the last Tumblr .gif I saw, he was growing a bit of a beard. But this guy….he was clean-shaven, and his hair was cut short, with boyish bangs. Bangs like the ones the producers of Supernatural had made Jared cut off after season 1 to look more mature. This guy….he also lacked Jared's mature face. He looked…younger. To be specific, he looked exactly how young Jared looked when he first played Sam on season 1 of Supernatural. The facial features, the body, the voice, all screamed Jared. But Jared hadn't looked like this for nine years.

"Who are you?" I asked, having an idea but immediately discarding it as crazy.

"I'm Sam," the man-who-could-not-be-Jared replied with an easygoing smile. "Sam Winchester."

"No…" I shook my head. "No, no you can't be. Sam….Sam doesn't exist."

"Excuse me?" said the man, looking at me in bewilderment. "Of course I exist. I've existed since May 2, 1983 to be exact," he said with a chuckle.

May 2, 1983, as I'd known, as a Supernatural fangirl, for the longest time, was Sam Winchester's date of birth. But that would mean….

"No. No. There's no way this is real. You're not real." I was standing up now, backing away. This was a dream. It had to be….right? I wound up backing right into the bench, knocking it over and tumbling to the ground. It hurt when I hit the sidewalk. I noticed my scraped hand was bleeding.

You can't hurt and bleed in dreams. But that would mean….this was reality.

"You're really Sam Winchester?" I asked, still internally wondering how this was possible. "As in, the Sam Winchester?"

"I'm sorry," Sam said with a quizzical raise of his brow. "Do I…know you?"

"No," I said quickly. "But, uh, I know you. Well I don't really know you, but, you know what I mean…Oh, wait, of course you don't know what I mean. Because this makes no sense. How are you real? You can't be real." Then I looked at Jessica, and my heart sank. "If you're really her, then….oh no. Oh my god. You have to get out of here, tonight!"

"Get out? What are you talking about? Who are you?" Jessica said, starting to get agitated.

"That doesn't matter right now," I said. "What matters is that you're going to die!"

Dean, Sam's brother, my not-so-secret fictional crush (who….might not be so fictional after all?) was going to come to Sam's apartment tonight and tell him that their father, John, was missing. Sam was going to go with him to investigate, and when he came back, he was going to find…..Well, it was one of the most iconic scenes in the whole series.

Jessica, pinned to the ceiling by unseen forces, her stomach slit and dripping red blood as, suddenly, she screams and bursts into flames. And dies. Oh crap. Jessica was real, and she was about to die. I had to warn her!

"Did you just say I'm going to die?"

"Yes!" I cried frantically. "You're in danger!"

"You're insane," Jessica dismissed me. "Insane, or just really wasted. Either way, you don't know what you're talking about."

I suddenly realized how I must sound to her- a stranger she found passed out on a bench, suddenly rambling about her imminent death. I sounded like an absolute lunatic. But I knew I was right.

"Sam, please, you have to listen to me," I begged. "Come on, we both know you've been having nightmares for a week in which you find Jessica dead, on your ceiling, and…."

Sam's eyes widened. I knew he was probably wondering how I knew that. Sam's psychic abilities wouldn't be completely explained until later in the season. He himself wasn't aware of them….at this point, he'd assumed that the dreams were just that. Dreams. He'd later blame himself, told himself he should have realized earlier that they were actually warnings.

But apparently, despite what I'd just said, he was still in denial. "Get away from my girlfriend." he told me coldly. "Get away from me. You're a really sick person, you know that, whoever you are? Walking up to people you don't even know and telling them they're going to die. What the hell is the matter with you?"

"Sammy, please," I pleaded. "You know I'm right."

Sam's eyes narrowed. "Nobody calls me Sammy except my brother."

"Sam, listen to me…."

"I'm going to say this one more time," Sam growled. "Go. Away. Or so help me, I'll call the police. Come on, Jess," he said, and walked away with her towards the bar.

Unbelievable. This was not happening. He wasn't going to listen to me. Neither of them were. Well, I can't do anything to help him if I'm in jail. I decided. So I walked away and wandered across the campus until I found a building I recognized as Sam's apartment.

"I guess I'll just wait here then," I chose. I hid in the bushes for what must have been hours until I saw Sam and Jess return from the party. I stayed hidden, watching the lights go out inside the house as they went to sleep. I knew that Dean would show up soon, waking Sam up, telling him that their father had gone missing.

Oh my god, I thought. Dean. If this is reality….that means I'm actually going to meet him. The character I've squeed over for almost ten years now.

But it wasn't as if I could just run up and hug him, I realized. In this world, I might know everything about him, but he had never seen me before. Heck, he'd probably shoot me if I tried.

I still wasn't sure if I was ready to except that this was real. But if Dean showed up right when I expected him to, how would I be able to deny it anymore?

I'm not sure how, but somehow, as I was waiting for my hero to show up and for my entire concept of reality to change, I fell asleep. I only woke up when I heard the sound of a car pulling out of the driveway. The car was a Chevy Impala….Dean's car. I only caught a glimpse of the driver as it sped away, but….Holy. Crap. It looked exactly like Dean.

OK, I decided. I guess that's it, then. I'm living in the world of Supernatural.

That was hard enough to digest. What was far harder was the realization that the boys had just left on a hunt…and I'd missed them. There was no way for me to catch up to the car now. I was stuck here. All I could do was wait for them to come back tomorrow.

Tomorrow. I realized. Tomorrow, Jessica is going to die.

Before I even knew what I was doing, I was banging on Sam and Jessica's front door. "Jessica, open up!" I cried. "I have to warn you!"

Jessica opened the door, eyes narrowed. "You again," she barked. "Seriously, who the hell are you?"

"My name's Kelley," I explained. "And, listen to me, if you don't leave town before tomorrow night, you're going to be murdered."

"Is that a threat?" Jessica shrieked.

"What?" I gasped. "No!"

"Are you saying you're going to kill me or something?"

"No, that's not what I'm trying to say at all!" I protested. "You're going to be attacked by a….a…."

"A what, exactly, you fruitcake?" Jess grumbled. She looked like she was getting ready to call the cops on me. Not that I didn't understand why. But how was I supposed to explain what I knew was going to happen to her? I couldn't just say that demons were going to come after her. Even if it was the truth. Because then I'd really sound like a nutjob.

There was no way I could get her to believe me, I realized, feeling sick. There was no way I could get her to leave the apartment where I knew she was going to get killed. "I….I'm sorry," I stammered, before turning and running in the other direction. I was choking back tears. This….couldn't be.

I knew what was going to happen to her, and it didn't look like I'd be able to do anything about it. I had no proof.

But what if I could get some? I wondered, and headed to the campus library. I immediately began looking for books about demons, some piece of evidence I could show Jess to make her get the hell out of dodge. Maybe a text mentioning that thunderstorms and cattle mutilations, both of which had been in the news lately, were harbingers of demonic activity. Maybe just a book on how to protect yourself against demons, so I could draw a protective sigil on the apartment without her knowing. I kept looking and looking, only stopping occasionally to eat and nap. I kept finding a bunch of nothing.

Then, suddenly, I woke up with a start and realized I'd fallen asleep in the library at some point during my demon research. Hoping to find a clock tower that could tell me the time, I started wandering down the street. I found myself in front of Sam and Jess' apartment again. I hid in the bushes again when I heard voices coming closer.

One belonged to Jess. "Yeah, I'm afraid Sam's out of town right now," she was explaining to…someone.

A male voice replied cheerfully, "Ah, that's ok. I just need to come inside for a minute, so I can look for the textbook I think I left here when we were studying the other day."

"I can go in and get it for you. Bring it out to you," Jess suggested.

"No, I'd rather come in and look for it myself," the man insisted.

"OK," Jess finally agreed. "If that's what you want, Brady."

Brady?! I remembered that name. It was the name of one of Sam's friends, who a demon had possessed. Specifically, the demon that was supposed to kill Jessica.

Don't let him in, Jessica! I wanted to scream. I wanted to do something, anything, to save this innocent woman, but I just stood there in my hiding place, shaking. I'd seen what demons could do. I was terrified that if I revealed myself, Brady would kill me, too.

When I heard the door of the apartment slam shut, I took off running. I ran down the street, through the Stanford campus, and then out, out into the road. I don't know what I was thinking. Maybe I was thinking that if I could find Sam and Dean, they could do something to stop this from happening.

I spotted the unmistakable Impala at a gas station down the street, and my hopes soared. I started running towards the car, but then I noticed: Dean was sitting at the pump by himself. Sam wasn't with him. That meant Dean had already dropped Sam off. Frantic, I started running back towards Sam's apartment. I'd seen Dean twice from a distance and still hadn't been able to meet him. I guessed I'd have to wait a little longer. My sneakers slapped against the pavement as I ran towards Sam's place.

When I got there, it was too late. The building was already on fire. And that meant Jessica Moore was already dead. I sunk to my knees, not caring that they'd surely get scraped. I hadn't been able to change anything. I was a coward. Pathetic. Why was I here? What had brought me here, and for what purpose? Just to torture me and make me watch as all my favorite characters died?

Suddenly Dean was rushing past me into the burning building. I don't think he even saw me. His sole focus was on his brother. I continued to sit there, sobbing, unnoticed, for what seemed like forever.

Then suddenly Dean emerged again with a struggling, screaming Sam. "Jessica!" he was crying, over and over. "Jess! No! NO!"

We were all standing there when fire trucks surrounded the building.

Then, Sam's eyes fell on me. "You!" he cried. He recognized me! He must have remembered how I'd tried to tell him yesterday what was going to happen. "I…I tried to tell you, Sam," I sobbed. "I'm sorry. I'm so sorry. I tried to warn you…."

Now, Dean was looking at me. "Sammy, who is this chick?" he asked.

"I….I don't know her name," Sam choked out in between hysterics. "She came up to me, she told me yesterday Jessica was going to die….Why didn't I listen to her?" He looked at me again. "Why didn't I listen to you? What are you, a clairvoyant? Do you see the future?"

"Uh…" This was a far easier explanation than 'You're a television show, and I'm your biggest fan, and now suddenly you exist and I'm living in season 1, which I've already watched so I already know what's going to happen', so….I went with it. I found myself nodding. "Yes, I see the future."

"This girl told you this was going to happen?" Dean blinked in shock, looking from me to Sam, then back to me. "A girl walks up to you and makes a prediction that your girlfriend is going to die…You think that's something you may have wanted to tell me, Sammy?"

Sam looks at me, and I can tell, amidst his grief and shock, he's wondering if I'm going to tell Dean that he'd been having dreams about this same event. I don't.

Instead, I look into the eyes of the boys I have idolized for so long, and I say, "My name is Kelley. I think I was sent here to help you."

"Help us?" Dean repeats. "Help us how?" I can tell that he's suspicious of me. It's IC for him, but it hurts.

"Sam wants to hunt with you now." I reveal. "He wants to find Jessica's killer."

Dean looks back to Sam. "Is that right, Sammy?" he asks.

"Yes," Sam confesses miserably. "Yes, that's what I want to do."

"OK, Psychic Girl," Dean says, looking straight at me. "Predict me this: Are we going to gank this son of a bitch? If we start looking for this thing, are we going to find it, and if we do, are we going to win?"

"Yes," I nod.

"Well, then," Dean decides. "Since you know so much about it, you better come with us."

My heart skips a beat. "Are….are you serious?"

Dean nods, and I watch Sam, desperately angry, throw a shotgun into the trunk. He doesn't even look at me as he says that famous line that I already know ends this episode:

"We have a lot of work to do."

I know this line. But I never knew that it could be possible that in this world, or hallucination, or nightmare, or whatever it is I'm living in right now– that that work would become mine to do, too.

But now I'm here. And, in hindsight, I'm starting to think maybe I never should have wished to be part of this world, after all.

Then, it suddenly occurs to me that the most vital part of the "work" ahead, in Dean's mind, is going to be finding their dad, John. But I also know that by the end of the season, John Winchester will be dead.

I have a million questions, but the one most pressing on my mind right now is How the hell am I supposed to tell him that?

END CHAPTER 1

Author's Note: I've never written a self-insert before. Normally, I think they suck. I've tried to make this one as realistic and un-Mary Sue as possible. This chapter was almost 5,000 words…I think that's a lot more effort than most self-insert writers usually put in, don't you think? Lol How do you think I'm doing so far? Don't forget to review and let me know! ^_^

Until next time, may you always have enough salt.

-Storychan