So, I know you guys are probably wanting to find out what Dean's plan is but first, a little background chapter.

CHAPTER ELEVEN: The One With The Background

Three years ago…

Kate waved at the bartender, nodding at him with gratitude when he placed another shot of tequila in front of her right next to two other empty glasses.

She had just downed the drink when she felt a presence next to her.

"Can I buy your next round?"

She looked to her right where a guy was standing there and she had to admit, he was smokin' hot. Whether or not that was the tequila talking, she didn't know.

"Well that depends." She began, the man raising his eyebrows questioningly. "Only if it comes with no obligations."

"No obligations?" He asked, seeming caught off guard by her answer. "What do you mean by obligations?"

She eyed him up and down, taking in the grease stained jeans and his red button up shirt. "Well, normally, when a guy wants to buy me a drink it's because he wants to get in my pants." She said bluntly, watching as his eyes widened in amused shock. "Like, you'll buy me a drink. Because you paid for my next shot, I'm going to feel obligated to ask you to join me and then we're gonna talk and you're gonna use some cheesy pick-up lines on me." The guy laughed out loud, clearly entertained by the scenario she was describing. "So, the night will either end with me telling you to take a hike and I'll have to deal with your bruised ego telling me I'm missing out. Or, I'll go home with you and sneak out in the middle of the night leaving you feeling abandoned."

Kate watched as he digested what she said before he shook his head with a smirk. "Well it sounds like you've got just about every guy in this bar pegged."

Kate shrugged, grinning broadly. "You can still buy me a drink if you want, but don't expect anything for it."

He considered it for only a moment before he motioned for the bartender to fill up her glass, laying down a twenty-dollar bill on the counter. "Enjoy your drinks." He said before walking away.

Kate was struck. He hadn't said it with sarcasm or malice. He had said it as if he actually hoped she would enjoy them and his twenty was definitely going to buy her more than just one shot.

With the tequila taking the wheel, Kate spun in her barstool to face his receding back. "Hey, grease stains!" He turned around, eyeing her with confusion and a hint of smugness. "What? Am I not pretty enough or something?"

The guy walked back over, now less amused and more puzzled. "Excuse me?"

"Am I not pretty enough for you to sit here and beg me to talk to you?"

He chuckled. Kate made a mental note that she liked the sound of it. "I don't like to bother women. Especially the hot ones."

Kate seemed to consider that thoughtfully before she turned this into a 'fuck it' situation. "Well now you have to sit here and drink with me. You passed the test." She waved at the bartender again, passing one of her shots to the guy now occupying the barstool next to her. "I'm Kate." She said before holding out her glass towards him.

His lips tugged up slightly as he took his shot, clinking it with Kate's before drinking it. "Dean."

….

Twenty years ago…

"Julian, I don't want you to be alone."

He looked down to where Peyton was resting her head on his chest, having just interrupted the comfortable silence between them.

"I don't want our kids to watch their mother die of old age." She continued, already predicting what her husband was going to say.

"So, what are you suggesting?" He asked, seeming wary.

"I want you to take me down to Hell so I can become a demon. Like you. Like our kids." She deadpanned, feeling as Julian's arms tightened protectively around her.

"There is no reason for you to become one of us." He stated, hoping to end the discussion right there.

Peyton moved so she could look him in the eye, cupping his cheek. "Julian, let me do this. We've been together for 5 years. I don't want a lifetime. I want an eternity."

Julian just nodded, in no way disagreeing with her.

….

Kate felt her back hit the wall of the bar's bathroom before Dean's lips were slamming against hers.

She had to admit, this was completely out of character for her. But, then again, she had downed five shots of tequila so this must be what drunk Kate was like.

It hadn't taken long for them to get to this point. To be honest, Kate wasn't sure she'd even remember any of this in the morning. Dean had introduced himself, they started talking about how great tequila was and how a few more shots would do them both some good. Next thing she knows, she's making out with a complete stranger in the unisex bathroom of a bar.

By this point, Kate's shirt was on the ground and she knew she'd have to wash it a good six times before she'd trust all the germs to be off of it but at the moment she really didn't care. Dean was in the middle of unbuttoning his when Kate grabbed his hands.

"One and done?" She said, her eyes roaming his half uncovered chest. She couldn't get involved with some random guy she met at a bar. That is not the type of story she wanted to tell her friends and family.

"No obligations."

That was all Kate had to hear to finish ripping his clothes off.

….

Eighteen years ago…

"Jake, come on!"

Jake Carter looked up from the picture he was in the middle of drawing to watch as Ash ran towards him.

"Can we play a game?" He asked, his pudgy child fingers pointing towards the swing set that was set up in their backyard. "We can play angels and demons! But I call being the angel." He shot his brother a toothy grin, excitement coming off him in waves.

Jake rolled his eyes but couldn't stop the smile from spreading across his face. "Fine. One round!"

Peyton watched from inside as her two boys ran out the back door to play. "You could go out and play with them you know." She looked down at Xavier who was standing by her side, watching with longing eyes.

"I don't want to hurt him again." He said quietly, eyes dropping to the floor with shame.

Peyton kneeled to be at his level and used her finger to lift his chin up. "Accidents happen. And look," She gestured out the window to show Ash laughing as Jake chased him. "Ash is all right. You just have to be careful, that's all." She tried to reassure him but he just shook his head.

"No mama, I won't take the chance. I will never hurt my brother again." Xavier swore, at the time meaning every word he said.

…

"Ah, the walk of shame."

Dean looked up with annoyance after shutting the front door to find his little brother staring at him with a smug grin on his face.

"I'm just thankful you didn't bring her here. I didn't feel like explaining why you 'suddenly had to leave.'" Sam quipped, making air quotes with his fingers.

"You know what, Sammy? At least I'm actually getting laid."

"Dude, I'm seventeen. That's not something that's high on my list of worries at the moment. I have two months before my college applications have to be submitted and they need to be perfect." He reminded his brother, turning and grabbing a gallon of milk from the fridge of their parents' house Dean had inherited when their father died.

Dean just shrugged and walked through their living room to get to the kitchen where Sam shoved a mug full of coffee in his hand.

"So, who was it this time?" He asked, watching as Dean sipped his drink gratefully. He watched as his brother smiled just the slightest. "Oh no, don't tell me you found someone you actually like?"

"Why the 'oh no'?" Dean asked, scrunching his brows.

"Come on. We both know every time you like a girl you date her for a couple weeks before you break her heart. Don't do it to another poor girl."

Dean rolled his eyes. "Sammy, I'm telling you, this one's different. But you don't have to worry. It was a one and done, no obligations type of deal."

"You told her that?" Sam questioned, seeming suspicious.

"No, actually, she told me that. It was the first sentence out of her mouth."

Sam seemed to accept it but he could see the disappointment written all over Dean's face.

"You know the one huge thing I remember about last night though?" Dean asked, running a hand down his face. "And it wasn't how good the sex was, I mean it was mind blowing-"

"Dude."

"But, I told her that..." Sam could tell his brother was embarrassed by the way he rubbed the back of his neck sheepishly. "I told her she couldn't handle what was under my jeans."

"You didn't." Sam said, horrified. "Exactly how drunk were you guys? Like is she gonna remember that?"

"I don't know. God, I hope not." Dean admitted, his cheeks turning red from the memory.

Sam glanced at the clock, his eyes widening before he shoved a piece of toast in his mouth. "mmm mmhhm hmggh."

"Sorry, didn't catch that."

Sam quickly swallowed, holding out his hand. "Can I borrow the car? I need to stop at the library to get a book for class."

"No problem. Can you fill her up while you're out?" He asked, sticking his hand in his back pocket in search of his wallet. When he didn't find it, he frantically checked all his other pockets and even ran over to the couch where he had set his jacket. "Son of a bitch…"

"It's okay, Dean. I can pay for it."

"No, it's not that. This girl's theme the entire night was 'no obligations'. If I left my wallet at her place, she's not gonna feel obligated to return it." He said, thinking about all the hassle he was going to have to go through to replace everything he had in it.

…...

Fifrteen years ago…

Mom was dead.

Caroline couldn't believe it. Her family had told her she wasn't needed so she could stay in Hell to finish up the rack she was working on. Even with all her begging, Julian had still insisted she stayed behind.

Now look what happened, Caroline had lost both her mother and brother all because Ash had been too damn stupid to not get caught in a devils trap placed by a fourteen year old girl.

Well, she would be damned if she let this affect her. Instead of moping around, Caroline picked up a blade and started chopping.

…

"Hey, Bobby. I don't think I'm gonna be able to head your way today."

Kate was sitting at her motel room's kitchen table and rubbing her temple with one hand and holding her cellphone up to her ear with the other. She was supposed to leave to spend the weekend helping Bobby organize all his books but with this bad of a hangover, Kate could barely get out of bed.

She could practically hear Bobby's eyeroll. "How many shots did you have this time?"

"I don't know. Probably like five."

"You got that high of a tolerance?"

"Bobby, I've been drinking since I was sixteen. I've had plenty of practice." Kate reminded him, standing up to go track down a bottle of Tylenol.

"Normally you don't drink that much when you're alone."

Kate found a bottle in her duffel bag and quickly popped two pills in her mouth. "That's because I wasn't alone." She said off handedly, hoping he wouldn't ask any questions.

"I hope you at least used a condom."

"Bobby! No offense, but that's not something I want to talk with you about." Kate said, sounding mortified. She walked out of her bathroom to go change her clothes but when she went over to the bed, she saw something brown sticking out from under it. Going over, she bent over to find a leather wallet lying there.

"Kate, I've bought feminine hygiene products for you. We passed boundaries five exits ago."

"This is not good." Kate cursed under her breath, opening up the wallet to the license of Dean Winchester. "He left his wallet here."

"So? Just return it." He offered, not seeing a problem.

Kate rolled her eyes. "Bobby, I spent practically the whole night telling this guy it was a one and done type of deal. I can't just show up! What if he wants more?" She said, although, the more she thought about it she really wouldn't mind a round two.

Now it was Bobby's turn to roll his eyes. "You've got yourself up on a high pedestal. Just return the damn thing, the man needs his wallet."

Even though Kate hated to admit it, she knew Bobby was right. She could talk a hard game about no obligations, but she wasn't going to make him replace everything just to prove a point.

….

"Mommy, why can't I go to school? Xavier and Caroline got to go."

Peyton looked down as Ash tugged on her pant leg, gazing up at her with disappointed eyes. "They only went for a year and that was before we realized how fast you guys grow."

"Why do we grow faster than everyone else?" Ash persisted, not quite willing to let it go.

Peyton sighed as she picked him up and went over to their rocking chair, setting him on her lap. "Honey, I promise, I will explain everything to you. But not yet, you're too young."

"I am not!" Ash roared, crossing his arms defiantly.

She shook her head, wishing that she didn't have to keep having this conversation. "Ash, it's too dangerous. You know how you and Xavier were playing that one time and he shoved you really hard without touching you?" She watched as Ash nodded, showing no signs of being traumatized from that incident. "Well you can do that to, remember? Now what would happen if you went to school and accidentally did that? It wouldn't be good."

Ash uncrossed his arms but the pout on his lips didn't move. "I wouldn't want to hurt anyone."

Peyton rubbed his back before kissing the top of his head, hiding the haunted look in her eyes. "I know, sweetheart. Sometimes you just can't help it."

….

Dean's head turned away from the TV at the sound of three sharp knocks on his front door.

"Can you get that, Dean? I'm doing my homework."

Dean got up, switching the television off as he did so before making his way to the door and opening it.

"Alright so I really went back and forth on if I wanted to return this or not."

Kate came in like a whirlwind, gesturing with her hands as she spoke. Dean could see his wallet in her right hand as shock took over his features. "What happened to no obligations?" He asked, leaning against the wall to his living room with his arms crossed where Kate had walked into.

She turned and gave him a crooked smile. "I'm not a total asshole. I wasn't going to just not give it to you." She rolled her eyes and handed it to him, trying not to focus on how hot he was. She noticed that this time, she didn't have alcohol fueling her thoughts, she had really wanted to see him again.

"You know, I am happy you stopped by. I wasn't really a fan of your 'one and done' policy." Dean admitted, shoving his wallet in his back pocket.

"Oh is that so?"

Dean leaned forward and brushed his lips against hers but when Kate went in for the kiss, he moved to her ear to whisper in it. "I hope you don't feel obligated though."

Kate chuckled and grabbed his face in both her hands, guiding him back to her lips before she whispered, "I only hope you can handle what's under my jeans."

"Get a room you two!"

Kate pulled back abruptly, staring at an embarrassed looking Dean.

"That's my little brother who doesn't know when it's a bad time to interrupt."

Deciding she didn't care, Kate shook her head with a grin before Dean pulled her close.

….

TBC