Taking a Chance

Meeting Sam Winchester

As I lay on the dingy motel bed I think about dad and how he'd much rather sleep outside under the stars. He hated having to move around from motel to motel, but we made a commitment after mom was killed by that blood sucking vamp.

I just finished going after a witch who hexed a few men who were known cheaters, justice if you ask me. Sometimes I wonder when these monsters actually kill other bad guys, maybe I'll let this one go, let him take care of some more scumbags, but then I remember that they don't always do that.

A few days ago Sam Winchester was calling around asking hunters to help him find his brother, but he was only calling the ones he knew he could trust. He called dad's old cell. I answered and informed him dad was gone.

"I'm sorry to hear that. Are you his daughter?" He asks. "Yea. Can I help you?" I spit out wanting him to hurry. "Well maybe, you can help. My brother Dean went missing and I need help finding him." He ends his statement. "So you're asking if I wanna help find your brother?" I ask. "Yes. I need all the help I can get. I didn't catch your name?" He states. "I didn't give it." I hear him chuckle lightly, "Ok well sorry to have wasted your time." I can hear my dad now telling me to be nice and you always help a fellow hunter in need. "It's Olivia. I'll help you." I hear him let out a sigh of releif, I think maybe I'm the only one who has agreed to help him. "Thank you. I'll send you everything I have from where he's been and maybe in a few days we can meet up and discuss what we found." Within seconds I get an email from Sam. "Ok see you then."

That was two days ago, we're meeting up at the diner across the street. I've heard the rumors about Dean becoming a demon, but if he was I don't think he'd still be alive. His brother is a Winchester, I'm sure he would have killed him.

My phone goes off, I roll over and grab it from the night stand. It's Sam, time to meet a Winchester. I throw my long brown hair into a ponytail and slip on my red plaid shirt over my white tank top and run across the street. I walk in and immediatly spot him in the back corner. His medium length brown hair tucked behind his ears on either side. I knew it was him because he has the look that all hunters have when they have seen too much. He has his head down reading a paper, I stand beside his table, "Anything good in there?" I ask taking a seat across from him. He looks up and gives me a warm smile, "Hi. Olivia your're not what I had pictured." His remark confueses me for a moment, "Well sorry to disappoint." I say with some laughter. He waves his hands in the air slightly, "No, no, no disappoinment. It's just your very girly. I was expecting Curtis Schaffer's daughter to be a little more... I don't know tom boyish I guess. Sorry if I offended you." I shake my head, "None Taken. Lets get down to business shall we."

Sam brings out his laptop, and I think he needs to update. I in turn pull out my iPad, we start sharing our findings. Sam found a spree of bar fights in Texas, No one can find the man who started it, But they all describe Dean. "Well maybe he's in Vegas." I say and I see Sam tilt his head. "Why Vegas?" He asks. I shake my head, "Well I don't know your brother all that well but it seems he's been moving from the east to the west. Along the way he's stopped at every bar, casino, and strip joint along the way. So I'm no genius but my guess is he could be headed there next." Sam nods his head and smiles knowing I'm on to something. "Ok lets head to Vegas." He says gathering his things, "Whoa wait a minute. I said I'd help you not go on a road trip. I don't hunt with other people." I explain. His shoulders deflate and I stand to leave but instead I feel his hand grip my elbow. I spin around to face him and realize he's much much taller than I. I finally reach his eyes, which are a nice green, I see the sadness and worry in them. "Ok fine jolly green giant. I'll go, one condition if we find your brother and he is a demon I'm killing him." I see him gulp and nod.

We head to my room to gather my things, which isn't much. Dad always taught me to pack light so we can head out quickly. Sam stands by the door waiting for me, "So how long has he been missing?" I ask zipping my duffle before slinging it over my shoulder. Sam opens the door and let's me out before answering, "About a month." He says with despair in his voice.

I feel bad for him, he seems so lost without Dean. Dean must be some brother. "We'll find him Sam. I usually find my target." I say trying to reassure him. Sam's phone goes off and he kindly smiles before answering, "Really? Well that's actually on the way to where I'm going. Pick you up on the way." He grabs a pen and paper listening to voice on the other end, "Ok got it see you in a couple hours." He hangs up while getting in his car. A 76 Camaro, I quietly admire the midnight blue metal.

"Who are we picking up?" I ask turning into the interstate out of Denver he looks at me as if he's not sure if he wants to tell me. "Mine and Dean's friend Castiel." That name sounds familiar, "Is he a hunter as well?" Sam keeps his eyes toward the road and chuckles lightly. "No." He says. Oh Castiel, their angel friend who rebelled for them. "Cas your angel friend. I've heard of him." Sam glance at me, "Yeah that's him but his grace is fading so hence us picking him up." I nod as we continue our drive to Pueblo to pick up Castiel.

I wake up and see a motel sign lighting the inside of the car. I see Sam at the front desk and a smaller man beside him in a tan trench coat.

I exit the car and stretch as they walk out and make their way over to me. "Olivia this is Castiel. Cas this Olivia she's agreed to help us find Dean. She has an idea of where he could be heading." Castiel simply nods at me with a serious look on his face. "Are we staying here?" I ask. Sam nods and hands me a key to my room, "Your room is 27 next to ours. I figured you'd want your privacy." I take the key grabbing my duffle from the gun lined trunk. "Thanks." We head into our rooms, as I'm getting ready to lay down there's a knock at the door. I open to see Sam. "What's up?" I say letting him in, he sits at the small table by the window. "How much have you heard about us?"

I join him at the table, "Well you guys are the freaking Winchesters, descendants of the Campbell's. I know you guys kick started the apocalypse but also saved humanity from it. I also know you guys were supposed to be Michael and Lucifer's meat suits. You both took a trip to hell, although you came back without a soul. And Dean has the mark of Cain. Sound right?" I say proudly. He looks surprised but nods. "Yeah pretty much. I wanted to say thank you for helping me." I sit back crossing my legs, watching as he nervously tucks his hair behind his ears. "No problem. I just finished a hunt and had nothing else planned anyway." He smiles standing up and opening the door, "Well goodnight. We're leaving around 8." I nod and close the door as he leaves.

I toss and turn as usual, I haven't slept a good nights sleep since mom was killed. I sit up knowing all to well I'm not going to be able to sleep tonight. I grab the iPad and start tracing some of the numbers Sam gave me.

At 7am I give up tracing the numbers and the license plate on Dean's car. Nothing at all popped up, I change my clothes real quick, and go outside to soak up some sun. I walk around the parking lot for about an hour and start making my way over to Sam's room, unconsciously I stand there adjusting my boobs. The door opens and I look up at a red faced Sam. "Um what were you doing?" He asks. I brush past him, "Fixing myself clearly." Castiel is sitting on the edge of the bed near the bathroom. "Does he ever take that trench coat off? It's hot outside." Castiel eyes me curiously. "I stopped trying to figure him out a long time ago. We ready?" Sam says, and I nod as Castiel stands up I look at him, this time really look at him. He's has kind eye's, very blue kind eye's. He has some scruff on his face, that makes him look rugged.

As we enter the car, I claim the back, Castiel asks, "Where do we think Dean is?" Sam looks back at me, I assume that's my cue to tell the angel my findings, "I believe he's headed to Vegas." Castiel just nods and looks out the window. It's another long and quiet ride to Vegas. A 12 plus hour drive with a former soulless, demon blood drinking, bitch to Lucifer Winchester and a grace losing fallen angel. Dad would be proud.