Chapter Text
You're the oldest and the sister. Never been too girly, but you dress up if need be. You're talented at being a hunter, you knew Bobby Singer and that's how you met the Winchesters.
"Y/N! Hey, it's time to get up, we have to go now. Alright?!" Your brother would not let you sleep even for a few more minutes. Today was important you had been chasing a vampires nest and were close to finding it.
"Damn it, can't I just sleep?! The vampires aren't even out in the daytime." You roll over away from your brother, pulling your pillow over your head.
Duh, you knew that's why you had to hunt them now, while they were inside their cabin.
"Jay, just stop it alright, I'm getting up." you growled as you got out of the comfort of the hotel bed. Jay looked at you as he was already dressed and ready to leave.
"Why don't you go get some breakfast?"
"Yeah, you buying?" figured he's the youngest, but he acts more 'grown up' than you do, until hunting down the demons and monsters of the day/week you're chasing.
You look through your backpack and fish out your change purse, you recently had stashed a few bucks from the other day. You grab the cash and hand it to Jay.
He looks at you and raises an eyebrow. "What'd you like?"
"anything with bacon... and maybe some pie!" Jay rolls his eyes as he goes to the door.
You step into the hotel bathroom and shake your head, today was going to be a kickass day.
---
Dean and Sam Winchester were at the diner near the hotel where you and your brother are staying. Jay comes in and sees the brothers.
"Hey. Sam, Dean." He shakes his head.
"Hey Jay, you wanna sit with us? We just ordered so it'll be a while." Sam suggested.
"Where's y/n?" Dean sidesmiled. He really liked you.
Your brother raised an eyebrow at Dean. He's just like y/n. Weirdos. He shook his head and smiled, he sat as a waitress came to the table.
"Hey," he looked at her nametag and back up to her. "Melanie, can I get a to go order, omelet with lots of bacon, large coffee, and a slice of pie? any kind of pie, probably chocolate or pecan. It's not for me, it's for my sis." she nodded at your brother suddenly blushing. "And what would you like sir?" Now it was Jay's turn to blush. He cleared his throat and scratched the back of his neck. "Surprise me, I like waffles pancakes or omelets... don't need no pie for breakfast. Thanks. Oh and an ice tea please."
Dean grinned. He forgot you liked pie almost as much as he did.
---
You were already finished getting a shower and getting into your 'hunting' attire. You spritzed your hair, trying to tame your unruly wavy curls. Damn frizz. The oldest Winchester was on your mind as you let the hair dryer go you sang a Kansas song, looking at the mirror outside of the bathroom door. Never hearing the door unlock or open you kept singing while drying your hair. You spritzed a few more hair spray and eventually turned the hair dryer off. You still hadn't noticed the 3 men in your hotel room. Someone cleared their throat. You jumped and went for your knife at your side.
Instinct was all you had, ever since you were 17 and were fending for your younger brother, let alone yourself, hunting was in your genes and your brother was the only family you had left. You were the oldest, you must protect him, he's your baby brother.
"Hey, whoa! I'm sorry y/n. don't kick our ass." Dean said holding up his hands, not once thinking you'd actually hurt him.
"Sorry..." You put the knife back in your side pocket of your jacket.
"Dean! Sam!" You hugged both of them tightly. "How are you guys? What's new besides that we are on the same hunt again?" your stomach rumbled. "Uh... Jay." You motioned for your breakfast as he handed you the bag. Wonder what kind of food he got today? You opened the bag and looked at the contents. A slice of pecan pie, and a kickass omelet with loads of bacon. You sniffed the pie. This was desert, you should wait and eat it after the omelet. Jay sat the cup of coffee on the table as you sat down, motioning for the three to sit.
"So you guys still are hunting together huh?" Dean asked as he watched you stuff a healthy bite of your omelet in your mouth. Man you were starving. When did you last eat? was it yesterday morning? You had been so busy, only had a poptart and an apple. You had went to sleep exhausted of the hunting research. Wait, sexy green eyes was talking, what did he say?
Your brother looked as you inhaled your food as Sam shrugged and looked at his dopey-eyed brother. They both shook their heads, Sam and Jay both knew you two were attracted to each other, yet too stubborn to act on it.
"I'm sorry Dean... pfffft..." You shrugged and wiped your mouth with your napkin. He was still watching you eat. Your cheeks heated as you looked down at your almost finished breakfast.
Jay and Sam sat on the couch and both acted like they were reading the newspaper, when actually they watched you two idiots.
Dean forgot what he was saying and side-smiled. "Hey did you ever meet Cas?" He said cheerfully. You sipped your coffee and shook your head. "Nah, that your girlfriend?" you said half jokingly and half serious. Of course this gorgeous man would have someone.
Sam suddenly snorted as he tried to hold in a laugh. Your brother looked at him, Sam whispered to him who Cas was. and your brother laughed lightly too.
"What's so funny, you two?" you frowned as you looked at them, then looked down back at your pecan pie slice. You got a big biteful and watched Dean's expression. He was smirking at you.
"No... I don't have a girlfriend no one at the moment."
"Yeah, I know you... you have a flavor of the week, each hunt you go to." you suddenly wanted to take that back. Shit, why did you have to say that? Damn it. You looked down at the table. and back up at him. "Sorry." you swallowed hard. "I... didn't mean to say it like that. I just know the gossip." You bit your bottom lip, your heart raced as you waited for him to say something.
The two at the other end of the room pretended to see something on the wall that was fascinating. You swallowed hard again, and tried to stop your heart from beating through your chest. This was why you were a virgin, you never said the right things, no one would ever love you, not like how you feel towards this lovely man who looked like he was deep in thought. You ate the rest of your slice of pie and drank your coffee, who cares if it burnt your tongue. You deserved to not be able to talk.
"Wow... um... well... er... yeah, I used to be that way, sure." He said suddenly looking deep into your eyes.
You had changed him. He couldn't think of anyone but you, so he hadn't been with anyone, not even for a makeout session, since he met you on that hunt months ago.
"Sammy... could you and Jay, let Y/n and me be alone for a little bit?"
Sam sat up and nodded motioning to Jay, who also got up looking uncomfortable and walked closer to the door. "sure, you want us to go and then you two will catch up?"
Dean nodded. "Yeah, I just wanted to catch her up on some things first." He smirked at you. You sighed and shrugged not knowing what the hell was even happening.
---
"So... why did you really want them to leave us alone?" you asked innocently.
Dean started shaking his right leg and biting his lower lip. He seemed oddly nervous. You don't remember him ever being nervous. His leg stopped shaking and he cleared his throat and licked his lips.
"Well, I just wanted to let you know the reason that..." he never finished as you looked at him bewildered as what the hell he was saying. what was he going to say?
"Okay, so this is awkward." You nodded your head at your own statement. You twirled some of your hair in your fingers.
"Alright, I'm just gonna say this quick... IthinkI'mfallingforyou" What the hell? Did he just say... what I think he did?
"Wha...?" you stammered.
"I can't stop thinking about you, the way you laugh, the way you love pie, almost as much as me, the way you still have hope in your eyes even with all you've been through. I think I'm falling hard for you. I haven't been with another woman since I met you on our last hunt together."
You shook your head in disbelief. Was this really happening? You knew that Dean was a 'seasoned' sex machine, but you never thought he'd stop his one night stands for anyone, especially you.
"Dean... I..." he looked at you and put his hand on your cheek while his other hand softly caressed you skin as he took some of your stray hairs behind your ear. He knelt closer and kissed you passionately on your lips. He pulled himself away. and looked at the door.
"Whoa... that was... wow." You smiled stupidly. Damn he was such a good kisser, no wonder he made woman slither out of their panties. {He was the man you'd trust to take your V-card.}
"V...what now?" He looked up at you with a confused expression.
Shit... shit... did you just fucking say that out loud?! Oh God, now you just wanted to crawl in a hole and die. Your face suddenly felt flushed with panic.
"Uh... I... said, that the kiss was very impressive?" it sounded more like a question as you knew it hadn't been what you said.
"huh. So. What now?"
"Now, we hunt." You stepped up to walk to the door when Dean grabbed your arm and brushed himself up against you. You felt his cock harden against your thigh. You gulped and looked up at him.
"Stay, y/n. I need you. to stay."
"I can't... you pushed him away. You don't... you can't..." you shook your head in disbelief. How the hell could this man become hard just for you?
Your face flushed and your palms grew sweaty. You'd never had sex before, but this man, he was in your dreams screaming your name in ecstasy, you of course screamed his as you would always wake up in a cold sweat, with your heart pounding. Your brother of course knew this but never said anything, as he knew you'd never admit to it.
"I'm sorry. I can't." you sobbed and pushed him away. "I'm not good enough for you Dean. you can't want me. I've never, been..." He held you closer to him, still hard. He combed his fingers through your hair and pulled you into a kiss that you couldn't say no to. You moaned into his mouth as he grazed his hand on your ass, picking you up and sitting you on the bed.
"Y/n, I've wanted you since the first time I met you. Will you let me take you through this? I'll be gentle I promise." He said, even though he just wanted to rip off your clothes and do you right there. He waited patiently for you to respond, you felt his chest, abs, thru his shirt. God he smelled so good. how could he be so amazing?
you closed your eyes tightly; breathing in his masculine/pine/leather, scent. He looked down at you, and realized he was being selfish.
He got up from the bed and turned. fixing his shirt, trying to ignore his hard-on.
He shakes his head, with his back still towards you. "I'm sorry, y/n. I just I don't want to lose you, but I don't want to force you to do anything you're not ready for."
You lay back on the bed and breathe in his scent.
"I'll be in Baby if you wanna come to the hunt, whenever you're ready." He still wasn't looking at you. His head was down, and he looked up towards the door. He started walking away. He closed the door. His hard-on was still feeling noticeable to him, so he covered it up with his leather jacket. Yep. Not too cold, I'll just hold this here so no one notices. He felt like a teenage boy having his first hard-on, all over again. He ran down the steps towards the impala.
"What the hell just happened?" you say to no one but your stupid-ass self. You felt hot and bothered and were actually in a bit of a shock. Dean Winchester basically said he loves you and that he only thinks of you and wants to do naughty things to you.
"Such a frickin idjit." you said to yourself as you close the hotel door behind you.
How long was the car ride to the hunt? Sam and Jay had taken your car and you had to go with Dean. This was gonna be awkward.