The next morning you woke up feeling content with your head resting on something warm. You slowly opened your eyes to see that you were using Sam's chest as a pillow. Instantly the blood rushed to your cheeks as you quickly sat up, fully awake.
You looked around the room to see Dean sitting at the table giving you the biggest grin.
"Oh shut up" you mouthed before chucking your pillow in his direction. He caught it and tossed it back. It landed on Sam, effectively stirring him from his slumber.
"Wha- What was that?" Sam asked groggily wiping his eyes.
"Nothing for you to worry about" You said patting him on the chest before sliding out of bed.
Much later, you found yourself back at the bar having lunch sitting at a table across from Dean. Dean glanced at his phone for the tenth time since you sat down.
"Still worried about Richie?" You asked.
He looked up from his phone towards you and you could see the brief traces of worry cross over his face before he masked them over. At that moment Sam walked up to the table with three beers in his hands. He handed one to you and Dean before taking his seat next to you.
"You do realize there is red meat within striking distance, right?" Sam inquired looking at his brother.
"How many times I got to tell Richie he's gonna get himself in trouble?" Dean snapped a bit.
"Dean, you're assuming he's missing. I mean maybe he just bailed." Sam suggested.
"He's a moron. He's a sweet moron, but he's not a coward. He wouldn't just bail. I got to go find him." Dean announced with a determination, standing up.
"Alright, meanwhile I think I'm gonna trail this Trotter guy" Sam replied.
"Yeah?" Dean confirmed.
"Yeah I mean something about the way he looked at me last night. Maybe there is something going on here" Sam debriefed.
"There is something going on with him. Might not be our kind of thing but It's worth checking out." You added.
"Alright then. You two take care and let me know if you find anything" Dean commented making eye contact with the two of you before stalking off on his mission to track down Richie.
You looked up at Sam before slightly bumping him with your shoulder. "So what are you waiting for? Let's go find Trotter" You grinned.
It hardly took any time to find the man, as you followed him into what must have been his office. After following him for a little while around town you hadn't noticed anything deemed odd, at least yet. The two of you were hiding around the corner from Trotter's office when Sam's cell went off.
Looking panicked Sam quickly answered the phone in a whisper with, "Dean." There was a moment's silence followed by, "Yeah, hey I can't talk right now."
You could see in your head Dean freaking out wondering if his little brother was in trouble.
"Yeah I'm fine. Just meet me at the bar in 20 minutes okay" Sam said, pulling the phone away from his ear and closing it.
You had to cover your mouth to keep your giggle from slipping out and giving up your cover. The look of panic that came over Sam was just too cute and funny for you not to react. Before you could think about it anymore, Trotter and his buddy left the office.
Quickly the two of you snuck into the office, with you standing on guard in case they should return.
You heard the ruffling of papers and the opening of drawers indicating that Sam was going through the desk. You chanced a glance, looking around the office to see if you could spot something obvious. However, in the moment of distraction you heard a gruff "Hey" and you quickly turned yourself around only to be faced with Trotters buddy.
You quickly moved to get away when the man tried to grab you, but you evaded the attempt and threw a punch making him stumble back slightly. Enraged he came forward and threw another punch, just barely hitting his mark causing you to stagger into the desk.
Sam then launched into the fight and tackled the man. Just as you were regaining your balance you saw Trotter walk in with a gun and he took no time pointing it at Sam, while the other man made a break and held your arms behind your back halting the fight.
"What are you doing here?" Trotter asked pressing the gun into Sam a bit more.
"I think, maybe you know" Sam replied. You could tell that he was working on the best way to get out of this situation.
"Yeah? Well I think I'm calling the cops" Trotter responded. Cops? Not a demon, then.
"Cops?" Sam asked a look of confusion passing over his face.
"Breaking and entering, assault - you're in a peck of trouble, and so is your accomplice" Trotter continued to speak.
"Uh, well I think I- we- could probably explain it." Sam replied. As soon as the words left his mouth Sam twisted around, grabbing the gun in the process. You took that moment to make use of your legs and kicked back into the man holding you catching him off guard and sliding free from his grip.
"All right back up! Get back" Sam commanded the two men.
"Money's in the safe! Take it and go" Trotter sounded scared.
"I don't want your money. I just got to be sure" Sam said while reaching into his pocket pulling out his flask of holy water. He twisted off the top before splashing Trotter on the face.
"What kind of psycho are you?" Trotter asked looking both confused and enraged.
"Oh god" Sam mumbled. "Uh, I'm sorry" He raised his eyebrows and let out a small chuckle. "I think this was just a minor misunderstanding. Yeah okay." Sam reached out and pulled you behind him towards the door, getting ready to leave. "How about I just leave cause… you know I'll take these…" He unloaded the gun into his hand. "I'll uh leave this for you. Uh have a nice day?" Sam said turning around and walking hurriedly away pulling you along.
After making your escape from the building in a rush, You and Sam found yourself at the bar once again. You had been there for about fifteen minutes, looking amongst the crowd for Dean, when you noticed a woman with dark curly hair looking intently at Sam while sipping on her drink. Even though you knew nothing would happen you couldn't stop yourself from feeling slightly jealous. You took your spot next to him and grabbed his hand looking up at him. He looked down at you then glanced to the other woman before returning his gaze towards you and wrapped an arm around you. You smiled up at him before asking, "See Dean anywhere?"
"No" He tensed up and glanced around the bar one more time.
"You look kinda tense. You know, I know a surefire way to relax" The woman with curly hair spoke up, ignoring you.
In response he just gripped you tighter and pulled you in the opposite direction towards the bar, approaching the bartender.
"Hey. Hi" Sam greeted.
"What can I get for you?" The Bartender asked giving you a once over.
Sam cleared his throat gaining the man's attention again. "Um, you remember the guy I was with last night? We sat right here."
"The big hero who jumped on Reggie" The bartender smirked. Oh sure, Dean gets all the credit for being the Hero.
"Yeah, yeah the big hero. Right. Have you seen him around at all today?" Sam asked.
"Maybe. Depends." He vaguely answered.
"Depends on what?" Sam asked, looking confused. The bartender just grinned without saying anything else. You rolled your eyes before Sam spoke up again, "Oh my g- does everyone around here have their hand out?!" He pulled out his wallet anyways and handed the bartender a $20 bill.
"He left with Casey about an hour ago" He replied while putting the cash in his pocket.
"Any idea where they went?" You asked.
The bartender turned his gaze towards you before he responded in a sarcastic manner, "Her place, for bible study."
"Alright, you got an address?" Sam continued the conversation.
"Whats wrong with you?! You think I'm gonna give you a co-workers address. Just so you can go over there and get your freaky peeping tom rocks off?" The bartender said with a slight smirk.
You decided you would give it a shot and came closer to the bartender and with the flirtiest voice you could muster you spoke, "You know it would be a great deal of help for us if you would do me this favor." You also slightly place your hand on his arm making eye contact and throwing a wink.
He smiled at you before, he unwaveringly answered Sam's question. "Corner of Piermont and Clinton. Have fun. And if things don't work out for you sweetcheeks, I'll be here" He then gave you a wink before walking away.
You let out a shiver before turning around to see Sam with a tense jaw. You looked up at him, gave a smile, and grabbed his hand before leading him out of the bar. "I don't think I ever want to do that again" You told Sam once you were free from the crowded bar.
He looked down at you with a small smile before he pulled you into a quick hug. "So what do you say we go check out her house" Sam asked.
The two of you arrived at her apartment in another fifteen minutes. Sam stepped forward first with you trailing behind. You made eye contact before he knocked on the door. Apparently the door wasn't locked because it slowly opened up.
You both walked in cautiously holding your guns out for protection. "Dean?" Sam called out, echoed by you. You had made some progress into the house without seeing anything when the sound of a squeal surprised you. You looked forward to see that Sam had stepped on a pink pig slipper.
You let out a light giggle and quickly finished your sweep before re-holstering your gun. The two of you began to take a closer look around the room. Sam picked up a picture and found a small pile of sulfur behind it. "Hey Y/N, check this out" Sam announced. You shared a look of concern before deciding to head back to the bar to see what you could figure out.
The two of you arrived back at the bar and Sam pulled out his phone to give a call to Bobby. After leaving a message the two of you walked back up to the bartender from earlier.
"Hey excuse me, they weren't there" Sam said.
"I guess you got to catch your jollies another night." The bartender replied while grabbing a shot glass. "Here, why don't you have a drink and relax." He filled the glass.
"I don't want to relax. What is it with the people in this town?" Sam glanced at you sounding aggravated.
"Suit yourself, princess." The bartender said before taking the shot himself.
During their conversation you spotted the preacher sitting at a table on the other side of the bar. When Sam finished the conversation, he turned to you as pointed out the preacher, suggesting he might be helpful. He nodded and the two of you made your way over there.
"Father?" Sam approached him.
He looked up and replied with a "yes."
"Can I talk to you, for a sec?"
The father looked at Sam and then glanced over at you before giving a welcoming hand gesture. "Who's your friend?"
"This is Y/N." Sam introduced.
"Nice to meet you" You responded with a polite smile.
"Likewise." The pastor grinned.
"So, uh the bartender the other night, uh Casey. You know her pretty well?"
"Since she was in pigtails." The father gave a small smile.
"Well, she and my brother they, uh, they left tonight together." Sam awkwardly shared.
"Ah. Not that I approve, but they are consenting adults." He responded.
"Right."
"I'm sorry you said brother. I thought you were insurance investigators." He asked with slightly raised eyebrows.
"Right, right, well we are. It's like a family business you know. Anyways, I went to Casey's apartment, and they weren't there. I just have this feeling that they - that they might be in trouble." Sam told the father, looking down at his hands. You reached over and place your hand on top of his trying to comfort him.
"What kind of trouble?" He looked concerned.
"Just trouble. Please father I need your help. Is there anything you could tell me about Casey? Any place she'd go, maybe.?" Sam inquired.
The Father thought about it for a second before responding, "Yes, there is a place. Let me get my jacket."
"No wait, wait Father I don't want to put you out. We can handle this." Sam replied with a slightly panicky voice.
"Son. If Caseys really in trouble, then there's nothing to talk about." The father responded while standing up and pulling his jacket on. "Shall we go?"
You found it a bit odd how eager the pastor was to tag along on this adventure, but decided that it could be helpful. Sam placed one arm around your shoulders and exited the bar.
Taking the pastor's car you were on the road, Sam in the passengers seat and you in the back sitting in an awkward silence.
"So insurance investigating" The father stated, hoping to start a conversation.
Sam just murmured a yes.
"You enjoy the work?" He asked.
"Yeah. Yeah I like being able to help people" Sam replied shooting you a quick smile through the rearview mirror. You smiled in return.
"Ever think about doing anything else?" The father continued.
"Like what?" Sam seemed intrigued.
"Anything. You seem like a pretty smart kid. Somehow, I see you out in front of the pack. You could do some great things."
"I don't know. I like what I'm doing, I guess" Sam responded turning his attention towards his hands.
"Well it's your life. Does, um Dean?" The pastor began to ask but then wanted to clarify the name.
"Yeah Dean" Sam confirmed.
"Does he find trouble often?"
"Yeah. Yeah Dean finds his fair share" Sam chuckled a bit.
"Well it's a good thing he has you. His brothers keeper." He smiled towards Sam.
After that the car pulled up to Casey's house. "Dean?!" Sam shouted, heading towards the door. You reached up and knocked on the door. After hearing no response, the three of you decided to split up. You and Sam going one way, and the father going the other.
You hadn't walked too far when you heard Dean's voice shouting out, "Sam!"
"Dean?" Both you and Sam called out trying to detect where his voice was coming from.
"Sammy, down here! The basement caved in." Dean replied from some place a few feet away. Sam ran ahead of you and found the vent through which Dean was looking out of.
"Dean. Hey hold on, we're coming." Sam announced.
"The Father gave us a ride" You spoke up from behind Sam.
Dean glanced towards Casey before saying, "Sammy, Y/N, be careful."
The two of you shared looks before pulling out your guns. You carefully made your way back towards the driveway, where you saw the father standing in the driveway. He smirked when he saw you and Sam before he began walking in your direction. You stood your ground preparing for a fight when the sound of a gunshot rang through the air. The bullet shattered a statue by the front door. You turned your head to see Bobby holding a gun aiming it at the pastor.
With a flick of his wrist the pastor flung Bobby across the yard. He then looked back at both you and Sam. He flung Sam on top of the car and flung you in the opposite direction toward the wall of the house. You felt pain as you landed on the ground. You were glad you landed on the grass, although you were sure to have some bruises. You groaned out as you slowly tried to raise to your feet.
When your mind stopped spinning, you saw Sam kneeling down by Bobby, while Bobby handed him a gun. Must be the colt.
Sam looked a bit confused, but then a blonde woman directed Sam to go. You were curious to find out who she was but you didn't have any time to linger as Sam ran over to you. "You okay, Y/N?" He helped you complete your movement and place you on your feet.
"Yeah, I'm fine. Go save your brother, I'll be right behind you" You answered urging Sam to continue. He gave you a small smile and a quick peck on your head before rushing into the house. You picked up your gun from the lawn and limped your way into the house. Once you got inside, it was clear which way to head based off of the clamour of voices.
Upon arriving in the basement, you were greeted by the sight of the pastor dead on the floor. Dean was slouched on the floor by the wall, while Sam was pointing the colt at Casey.
"Sam, wait," Dean calls out, almost pleading.
Sam's gaze didn't waver in the slightest as he pulled the trigger, dropping Casey to the floor.
The tension seemed to fill the air, at least until Sam turned around and pulled you into a hug. The three of you made quick work of cleaning up the mess, grabbed Bobby and headed back to the motel. During the trip back Dean had explained what had happened. Once you were back it didn't take long for Dean to pack his bag and walk out the door to go chat with Bobby outside.
"You did a pretty good job today" Sam complimented you.
"Thanks, you didn't do so bad yourself" You replied with a smirk. "Although this wasn't the way I had planned my life to go, I've been enjoying it" You confided in Sam.
He smiled, "I'm glad."
"Alright, well I'm gonna go put my bag in the car, meet you out there" You ended the conversation. He nodded in response before you walked out the door.
"Leaving so soon? We haven't even had a chance to celebrate." Ruby's voice stirred Sam from his thoughts.
"Yeah, well you can celebrate without me" He replied in an annoyed manner.
"You're not gonna get all pouty on me now, are you?" Ruby persisted, but was met with only silence. "Come on! You killed two demons today." She smiled.
"Yeah, well maybe you don't care, but I killed two humans too." He snapped.
"Sam you know what happens when demons piggyback on humans." She said while taking a seat on the other bed. "They leave them rode hard and put up wet. Chances are those two would have died a slow, sticky death. You probably did them a favor."
"Did them a favor? You're a cold bitch you know that?" He turned around to continue packing his bag.
"Yeah and this cold bitch… has saved your ass a couple of times now."
Sam didn't want to listen to her anymore, so he slowly reached for the colt.
"Some respect might be nice. Especially, if you want me to help you out with Dean's little problem" She continued.
Sam quickly turned around and with a raised voice said, "You know what, you keep dangling that, but last i checked Deans still going to hell."
"Everything in its own time Sam, but there's a quid pro quo here. We're in a war."
"Right, but for some reason you're fighting on our team. Now tell me why is that again?" He sounded like he couldn't care anymore about her.
"Go screw yourself thats why." She retaliated. "I don't have to justify my actions to you Sam. If you don't want my help fine then give me the gun and and I'll pass it on to someone who will use it."
She stands up to the bed just as Sam aims the colt at her. "Maybe I'll just use it on you" He remarks.
She scoffs before replying, "Go ahead, if that makes you happy. It's not gonna do much for Dean though. So whats it gonna be?" She holds her head high open to being shot.
Sam reluctantly lowers the gun.
"That's my boy. This won't be easy Sam. You're gonna have to do things that go against that gentle nature of yours. There'll be collateral damage...but it has to be done."
"Well I don't have to like it."
"No you wouldn't be Sam if you did. On the bright side i'll be there with you. That little fallen angel on your shoulder." Ruby smiled.
"I don't need you to be there with me. I've got Y/N. All I need is for you to help me save Dean" Sam snapped before picking up his bag and leaving the room.
AN: Feel free to give me critiques, I struggled with this chapter. I think it might have been because I wasn't thrilled with this episode, but I appreciate any thoughts. :)