A/N: This is my first venture into the Supernatural fandom and it's Dean/OFC. Sorry guys, I don't write slash, I just read it on occasion. I've watched seasons 1 - 7, haven't watched 8 yet even though it's finally on Netflix and am now rewatching everything as a 'refresher'. The beginning is set during 98/99 when Dean was on a '5 days, 5 states' road trip supposedly. SPOILER ALERT: He was actually at Lisa's loft, which has been changed so technically I suppose this isn't canon-compliant as I removed Lisa from this and have no intention of putting her back in at any point.

Apologies in advance for Dean's OOCness, I'm working on it, promise.

Reviews are great, flames are used for baking cookies.

Pie

1998... or 1999

He had to of been about 19, maybe 20, but apparently nobody but her noticed because he was served the beer he ordered. Not that it would have mattered; her daddy didn't give a rat's behind about age, so long as you looked over 16 and didn't raise a fuss. And if the cops showed up as they were occasionally wont to do, he would quickly lie and spout off some bull crap about the underage drinker 'stealing' from the bottles.

Jane snorted, shaking her lowered head as she resumed sweeping the floor. It was nearing closing time, and daddy was already counting the till while mama was beginning the process of ushering out the drunks. She had just turned 18, that same day, and lucky her… she had spent her birthday in the bar. Serving drinks to the regulars and the strays, both varieties delighting in slapping her gray, cotton skirt covered behind.

"Janey, hurry up girl, I need you to wipe down the counters."

"Yes, daddy…" Sighing, she finished up, emptied the dustpan and stowed the broom back in the tiny little closet where her meager cleaning supplies resided. She grabbed the cleaning solution they used, a fresh rag and slowly ambled towards the bar. Daddy was moving away, probably to go run the money home and store it in the safe.

Another sigh, and she started wiping down the counter, listening to mama coaxing the last person –besides underage at the bar- out the door.

"Jane, you have him out of here in five, not a second later."

Jane frowned, looking up.

"I'm going to go make sure he don't try skimming any of that money. Five minutes."

And now it was her and him.

"They do that to you often?"

He spoke, and she simply shrugged her shoulders. "Often enough." She raised stormy gray eyes from the dingy counter she had been half-heartedly wiping down to meet hazel eyes, they looked green but she could see brown as well.

"They'd just leave you alone with a stranger like that?"

His voice was a bit rough. She kind of liked it, not that it mattered much.

"What if I'm a serial murderer?"

The corner of her pale pink lips curved slightly and she dunked down to grab the9 mm from beneath the counter. When she straightened, she was aiming it at him, safety off. "Are you a serial murder?"

He considered her, finally raising his half-empty glass and drained it. "Nope. Just a drifter." He set the glass down in front of her. "How much time do I have left?"

"A few minutes."

"That your daddy's gun?"

"No, it's mine. He has a sawed off."

"Good choice."

"Only for close range. Anything else and they're worthless."

"Fair enough. That why you use the nine?"

"Mostly, and it fits in my backpack."

"Backpack? You still in school?" He smiled gratefully when she set another glass down in front of him. "Since we're breaking rules, how about a whiskey chaser?"

"Sure, and that'll be seven bucks."

"Seven?"

Jane nodded, holding out her hand, gun now setting on the counter between them. "Sure. The drink, the chaser, and the fact that you are now out of time."

"Well hell Jane, I should at least get a slice of pie for seven bucks."

"There's a diner across town that's open 24/7 and no, I'm not in school. I just cart around the backpack because purses don't carry everything I need on me. What's your name?"

"Dean." He cleared his throat and winced, shaking his head slightly as the whiskey burned a trail down his throat. "Come on, I'll buy."

Jane froze, the coins he had paid her with dropping into the till noisily. "What?"

"Pie."

"You paid me in dimes and quarters."

Dean flashed her a very charming smile, one she was certain worked quite well for him. "So?"

"What'll you pay the waitress with? Nickels?"

"Is that a yes?"

"Let me grab my coat and lock up, I should probably put the gun away too..." She said finally, turning away in order to hide her own small smile.

"It'll be in pennies."

"I thought you were joking about the pennies." Jane had never been so mortified in her life. She had shifted in the booth, turning away from the waitress, and blushed like she had never blushed before when Dean had paid for two slices of pie… in pennies. What was worse, he had done it with a flourish and no shame.

"Nope." He was already forking pie into his mouth, smirking at her. "Come on now Jane, I just paid a hundred and fifteen pennies for that slice. Don't waste it now, sweetheart."

"Don't call me sweetheart." She scowled, lifting the fork. Why had she agreed to this? The silver lining was that the pie was delicious, rhubarb, she loved rhubarb. "You really a drifter?"

"Sort of." Dean spoke around the food in his mouth, fork tines scraping his almost empty plate. "Work keeps me busy, moving a lot. I'm on… a road trip, vacation type deal." He laughed. It sounded forced, even to his own ears. "Bar wench, huh?"

"That's me, the bar wench." She muttered, stabbing at her crust until it crumbled. "It's temporary, trust me."

"Sure, sure."

"I mean it. I'm not going to be there long, just long enough to-"

"Save up and leave town. Move to the big city, go to college, that sort of thing?"

"Yeah, sort of."

"Sounds boring."

"You're a 'drifter' who pays with loose change. How's that working for you?"

"So far so good, bought you dessert didn't it?"

"You can take me home now, Dean."

He was finished with his slice anyways, and stood up. Smirking, Dean leaned over to swipe his finger through what remained of her whipped cream, then popped the digit in his mouth. "If that's what you want, sweetheart."

Huffing, she stood up as well, tugging her sweater back on over the oh so lovely matching gray blouse she wore to match her skirt –complete with a black, pocketed apron. It was way past two, she was tired, her feet hurt, and- "Don't call me that."

Dean pushed open the door, gesturing for her to go first. "Ladies first."

Jane made a mental note to never accept pie, or rides, from strangers. Especially strangers like him.