Charity Case | Sam & Dean Winchester

Chapter Four: Business Issues

The car ride was slow, tantalizing so. Luckily, the driver hadn't looked at you once in the hour but he didn't give off any weird vibes to begin with. The only thing that was really irking you was the soft noise in the background. Girls Just Wanna Have Fun, literally playing on loop. And the further you observed the driver the more you found out that he genuinely enjoyed the song this much.

But you weren't about to say anything, that'd be rude. Plus there's no room for you to judge. Your apartment came into view not much longer after that, the familiar beat of the song starting back up as you hurriedly grabbed your belongings.

You hardly had a moment to open the door and flee before the man was stopping you and turning down the volume of the music. "So you're the new one, huh?" You looked at him curiously and he huffed back. "You're the Winchester's new arrangement?" You shook your head a little, appalled that he went out of his way to be nosey. "Excuse me, and who are you? What's your name?"

He chuckled reaching between the partition and offering you a hand. "I'm Bobby Singer and I'm sure I'll be your driver from now on." He seemed to spit out his profession with malice. You reluctantly took his outstretched palm and shook it firmly. Your brows furrowing not much longer after your skin separated from his, and you open your mouth to leave a question.

"Then yes I guess I am the new one, how many arrangements have they had before?" Maybe you could get some information out of this guy, he seems to be apart of their everyday life. His face scrunched up with amusement and another breath of laughter left his lips. "You're expecting me to have been keeping count girlie?"

His head shakes and then he stares before him, "One thing I do remember," his eyes travel to the rearview mirror and they bore into yours with something heavy behind them. "Their last arrangement didn't end well." Bobby's hands runs down his face and he quickly jumps from his seat. That emotion in his eyes, it made you curious.

You'd probably remember it for a long time. Not but a few seconds later he opens your door and you jolt, questions filling up your brain so much they could leak from your ears. You step out and you inquire him one last time. "What happened?" He gazes at you with an intense warning, "Honey it's not really your business." He's quick to grab your upper arm firmly, leaning in close to your ear. "Nothing I said was your business, so keep it between us you hear?"

After that you watched as he hopped back in the driver's seat and sped away. You were lost in your thoughts as you made your way up the staircase, so lost in fact you hadn't heard the arguing in the apartment. As you opened the door however all conversation ceased and both pairs of eyes landed on you. "Y/n?" Dimitri said confused. "I-I wasn't expecting you back tonight."

It didn't take a genius to know that Dimitri had connections to the Winchesters. And you had to be an idiot if you thought that Dimitri liked the Winchesters. It was very clear he had a past with them.

"Well I'm here, why did you guys look so worried back at the cabin?" You get straight to the point. You've been learning a lot about these peculiar men, and you've only just started. "They're just a couple of men that I used to run a business with." Your eyebrow peaked in interest. "Oh really what kind?" You spoke. Though hoping to look nonchalant, you started unwinding after your night out. Setting your purse down, placing your keys in the proper places, ect.

He didn't have an answer for you. A half assed blowing off your question with a sound that's between and huff and a chuckle. His hand had even came out to the front of him, as if swiping your question off of his plate in distaste. "All you need to know is it made me a lot of money, but the Winchesters and I don't partner up like that anymore. We don't need to." He had a cocky grin on his face but you couldn't catch his eyes. There had to be something more to it than that.

Not to mention the disappointed and confused expressions on Carmen's face. "Anyways it's a long drive home I better get started, bye beautiful." He reached over to stroke your roommates chin with an air kiss before he maneuvered around you.

As the front door slammed and he floored his car down the street your apartment was silent. "You could feel my urgency tonight right? When we were telling you to leave with us." You just barely nodded bending down to take off your heels, placing the mask that once laid lazily across your neck not but seconds ago, on the kitchen counter.

"Then why didn't you walk away." He was looking at you like he was waiting for you to put the last piece of the puzzle into the picture. "I was just giving this whole sugar daddy dating thing, a real try." You paused shrugging. Although mentally you were praising yourself, that was probably a good enough lie for him to lay off a little.

"I just wasn't done yet, plus I saw them at the dress shop earlier and th-they were pretty hot." You tried not to blush but your body betrayed you, yet the little bit of truth you threw into the lie made Carmen scoff. "Fine." He paused with a pout, "Did you end up getting their number?" His excitement bubbled through the surface eventually and you smiled with a nod.

After a moment he shrugged, "I'm only worried because Dimitri is. It's not like him to act that way." You pondered up at Carmen with a frown. "It has something to do with those guys, but I hope its nothing cause you gotta get your bag." The two of you laughed lightly and went on your separate ways.

Your brows were furrowed as you were pulling your sheets from around the matress corners. The fact that they had left it up to you to call them, it was on your mind and making you nervous. You definitely wouldn't call tomorrow. That would be too soon.

You flopped on your bed with a heavy sigh, hopefully you didn't get yourself into something you wouldn't be able to get out of. You carded your fingers through your hair as you thought, tomorrow you needed to look up Dimitri, they obviously had more going on than what he had said.