This is a first attempt at a fan fiction story.

Sam and Dean are obviously not characters created by me, but I hope I've managed to stay somewhat true to how they are with how I've written them.

The OFC was named Chuch (the nickname of a wonderful friend that allowed me to use for this story) in the 2009 version, but as of 2021 and coming back to hopefully finishing this story finally, I've switched it to Church. A big thank you to Chuch for entertaining the idea back in the day, letting me use her nickname, listening to the rambles and giving input numerous times by being a beta reader.
This all started as a joke, and I found it fun to write at the time. So many years later I still think it's probably a tad cheesy. But I've come back to clean it up and edit things to, I hope, make it a little less awful and cheesy and terrible. Of course, most of it is still the same all the same story with some editing. It may be shorter in the end as the chapters were slightly reworked as I went through everything and started to post it over on ao3. Yeah, you can find it over there too, if you prefer that site or reading the more adult language used at times. Please bear with me as I post the updates to all the existing chapters one at a time here.

It still serves as sort of a prequel to the other stories I wrote for Dean and another OFC since they were always supposed to meet in this one. Feedback still welcome and appreciated!

It had been over a week since the last job, and it wasn't like they ever got much of a vacation, but this was as close as it got to one, and both Winchester brothers were growing restless.

Sure, Sam and Dean had each said they wanted out of this life numerous times, but when they weren't hunting down something of the supernatural kind it was like twiddling thumbs for them. Dean had never really known anything else, and all the traces Sam had of a short-lived normal life had faded away in the past few years.

Cruising along highways and back roads, Sam and Dean had come to this town on a whim hoping a job would surface. They had arrived a day earlier, followed a few leads from the local paper but those turned out to be dead ends. Dean figured they'd stick around for a few days, hustle a few games of pool to make some cash, and that he'd at least pick up a woman or two and have a little fun. Sam could tell Dean was itching for a hunt, he was too, but they couldn't exactly find one. It wasn't for a lack of trying. Even if there was an upcoming war on the way, somewhere weird was going on. The world they knew was too quiet, which usually meant one thing… a crap load of trouble was on its way and it was only a matter of time till it surfaced.

[ - ]

That night Sam and Dean were out at a hole in the wall of a bar. They'd finished playing their games of pool, won a fair amount of money off two men who probably would have won against anyone else. The men had been good players but neither had been on the same level as Dean by himself, never mind when it became a brotherly effort. The boys had learned with to hustle with the best and worst of them thanks to their late father and spending a lot of time in such dives like the one they were at.

Sam was now sat at a table nursing a beer, searching the usual websites for even the hint of a job on his laptop, but there was nothing on the wires. Even Bobby had called the other day to say things were quiet for all the other hunters and it troubled all of them with what must be brewing.

Shutting down his laptop, Sam quickly spotted his brother at the bar. Dean was talking to a woman who was buying into whatever story he was feeding her about himself tonight. Sam knew it was only a matter of time before his brother and his next conquest left. He was surprised they hadn't already. It never seemed to take Dean very long to seal the deal.

He watched them for a moment. It still amazed him how natural his brother was at this even though he'd watched his routine too many times and how easy it was for Dean to pull chicks in with the flash of a grin and a cheesy line to hook them. Sam had to admire it even if it wasn't his style. His big brother was just that kind of guy, and it never seemed to fail him. Only about two months since he'd gotten out of Hell now, and Dean was back at it like he hadn't missed a beat.

Sam's eyes scanned the bar as he finished his beer out of force of habit. He figured he could leave Dean to have his fun and head back to the motel room for the night. Maybe stop in the diner across the street from the motel like he'd done the night before. Researching things and keeping his mind sharp seemed to go by faster sometimes when the coffee kept flowing and he didn't have to listen to Dean's snoring or bad dream murmurs from across the room.

He gave Dean the nod, started to gather his stuff together. Sam saw Dean excuse himself for a moment and then head over to him.

"Bailing already, Sammy?" Dean asked with a slightly sour tone.

"Yeah, Dean," Sam said.

"You know, you could try sticking around a little longer, maybe have some fun. Uh, Crystal, or is it Shauna? No, uh, it's… Jenna, she has a roommate she's willing to set you up with."

Sam sighed. "Don't worry about it. Have fun. See you in the morning."

Dean shook his head. "Fine, Sam. But you're going to miss a hell of a time, they're college cheerleaders. Go team." Dean grinned.

Sam gave Dean look that said it was typical. "And what your angle tonight, Dean?"

"I'm a music video director, working with an up and coming hot star, looking for some talent and you're my assistant." Dean chuckled.

Sam laughed. "Sure. Later, Dean."

"Have fun sleeping alone, Sammy." Dean headed back to the bar and the girl.

Sam picked up his stuff and headed over to the door. Before he left he heard Dean loudly say he'd just fired his assistant and was now free for the night.

Some things never changed, and Dean's tactics certainly fit into that category. But the same could be said for Sam as he was on his own again while his big brother got lucky once again.

There was Ruby he sort of had a thing with sometimes, but even now it had been a awhile. It had definitely been a bit longer than the two weeks of searching for a hunt. And it was starting to get to him. While he wished he could be more like Dean who often never felt nothing more than a physical connection, he just wasn't built that way.

Sam walked out of the bar and down the road back towards the motel. It was a ten minute walk at most, but it was just enough time to feel his loneliness set in and pain from the past over lost loves. When he was feeling this way, the younger Winchester knew he was in for a long night.

As Sam got closer to his destination, his eyes shifted between two neon signs. He had a choice, spend some time in the diner or sit in the room that was almost identical to the nearly every single motel or hotel room they'd ever stayed in. Eyes on the open sign instead of the vacancy one, the choice was easy - the diner it was.

Sam settled into a booth and watched as a waitress appeared almost instantly. It never took long in these places, especially at this time of night. He ordered a cup of coffee which took the waitress all of a minute to get to him. It wasn't busy by a long shot, but there were at least six other stray customers scattered about.

Taking out his few books and laptop, Sam got to work. There was always more research to be done and he didn't mind doing it. Sure, Dean liked to refer to him as some nerdy encyclopedia of weird knowledge, but it had saved their asses more than a few times on the job. It never hurt to stay on top of lore or learn something new, so he drifted back into the world he knew all too well - one of evil and supernatural things and beings.

Two hours and three cups of coffee later, Sam took a break. He'd been caught up in translating some Latin text that had to do with demons and their activities or lack of from time to time. Not the most fascinating stuff to read, but it might explain something about what was going on lately.

He hadn't noticed that the place was pretty much empty now. Besides him, there were only three other customers left. Two men sat in one booth whispering across the table at each other. There was a woman in another booth hunched over a book. Sam had seen her in here the night before doing the same thing. They'd exchanged a few glances last night, he'd noticed that she had been looking at him and scanning the room just as he had. Yet, tonight she seemed lost in whatever she was reading. There was something about the way she was sitting there though that reminded him somewhat of himself, on alert and guarded while deeply consumed in the material before her. It crossed his mind that she could be a hunter, but the chances of that seemed slim. They always were. It happened from time to time, but usually meeting another hunter by chance just didn't happen.

Whoever she was, he noticed she was attractive. She was thin but fit, had dark shoulder length hair, an olive complexion, and had some sort of mysterious vibe going on that made him look at her a little longer than he normally would at most women. She'd smiled briefly at him last night, and had at least seemed friendly enough even if they hadn't exchanged words.

Sam decided he'd wait a few more minutes and then pass by her booth on his way to the men's room since she was sitting in the last one that was located closest to the restrooms and probably another exit. He'd also try to get a look at what she was reading to see if he could break the ice with that. Or maybe he'd just go ahead say hello for the hell of it. Dean was right; he could try to have a little fun sometimes.

Heading towards the restroom area, walking casually by and passing the woman in the booth, Sam peeked at what lay on the table before her. A few old books were stacked on the corner of the table, but one lay open before her as she wrote down in a notebook. Sam could see faded text that looked a lot like Latin on one page, well from his upside down view anyhow. There was also a demonic portrait on the opposite page. He continued to walk to the men's room and now wondered just who the hell this woman actually was and why she was reading about demons.