Charity Case | Sam & Dean Winchester

Chapter Six: Drink Some Wine

A silk dress sat neatly on your curves. Lace up heels accompanying it. You had been sitting looking at yourself in the mirror for about thirty minutes now. Waiting for a call or a text. Your finger was lazily scrolling through Instagram.

In the back of your mind you wondered if the Winchesters had an account. Though you quickly decided not to bother looking for it, the two of them were so private in person why would they throw themselves on other peoples timeline. Just then, a heavy knock was laid on your apartments front door and you jumped. Making your way over to the sound you peered through the peep hole, expressing your slight annoyance through a glance at the back of your skull.

The man was turned around, but from the sharp jawline, you knew it had to be a Winchester. You opened the door shyly and smiled at Dean. He took a glance at your outfit and grinned back down at you. "I'm glad you're ready to go, hope I didn't keep you waiting long." He held out his arm for you to take and you did so hesitantly.

You came to the conclusion that he was the more intimidating of the two brothers so far. "Thirty minutes, does that happen often?" You said with a faux seriousness. He chuckled from his chest, brushing his fingers over his blazer and pulling it tighter around him. As he did so he jerked you a little bit closer, you felt it was intentional but he didn't mention anything.

"So where are we going to eat?" God, it was a hassle to keep him talking. Dean's bottom lip jutted out as he pondered your question, eyes casting down at you with some sort of amusement. He didn't answer before the two of you reached his ride, a handsome black vehicle with a beautiful tan interior, running at the edge of your drive way. You gasped, letting his hand fall from your side. "Wow. Look at this baby." You couldn't help the smirk on your face.

You didn't have much knowledge of cars, but with a mechanic for a father you knew your classic ones at least. "A beauty ain't she, and you already know her name." There was an expression on his face. One you couldn't pinpoint as he gazed at you across the hood. His shoulders seemed alot more relaxed as his palm glazed over the top of the black paint. His other hand picking at a small tree leaf that had fallen, stuck in the cracks by the windshield wipers. "Baby is her name."

You giggled, "Very cute." His small blush was something he had tried to hide but you caught it. Now you knew one of his soft spots. "How'd you find a Impala these days anyways?" You looked around for any indication of when Baby was made, and tried to remember what year this model came out. "I've had it for a while, it's a '67."

You were excited to get in it and look around, opening the passenger door and sliding in. You waved at him and raised one of your eyebrows. "What are we waiting for, I'm trying to ride around in her." You lightly tapped the dash board and sat back with your legs crossed. Dean hopping in not long after that.

While the two of you were driving you were silently admiring him. Mostly his hands. They made you weak in the knees and you were intrigued about how he used them. A watch sat on his wrist, clean with a unique design that sat in gold. He had the same cuff clip that Sam had at the Winchesters Cabin. The suit he wore was just a little tight on him, his broad shoulders showing a nice defined figure of his arms. You licked your lips before you met his face, a cocky smile laid there and as Baby rolled up to a red light he turned towards you. Catching you in the act of lustful gazing.

"I can't tell which one you like better, me or the car." You turned your head away from Dean me deep voice, quickly hiding your embarrassment . Before lightly clearing your throat and looking at the moving road in front of you. "Definitely the car." He let another chuckle escape his lips and the sound traveled down to your core.

You couldn't be in a confined space with him so it seemed. With no underwear and your dress would show how easily excited you got. Shortly after that the two of you arrived at a restaurant. Your features twisted into an expression of shock as a Dodge Charger came screeching to a stop beside the Impala. You saw Dean roll his eyes at the loud roar of the vehicle.

You could see Sam through the window, though he hardly acknowledged you. He climbed out from the driver seat. For how tall he is you were surprised he was able to fit in there. He took a moment to fix his suit jacket and when he was finished, with a devilish grin on his face, he opened your door for you. Lending a hand to help you out of the Impala.

"Good to see you again." All you could do was nod with a blush, letting him lead you up to the sidewalk.

They had reserved a private table in the back, as the host sat the three of you down you saw the way she looked at the Winchesters. You sat back and grumbled lowly, quietly trying to remind yourself this is only an arrangement not a marriage.

Her name tag had two letters on it, 'Jo'. A cute little blonde. That once you looked over at your companions, they were as infatuated with her as she was them. A pout came to your lips, but you suppose you cant be mad. What you hadn't noticed though was the side glances and smirks being thrown at you, as you completely ignored their conversation.

The three of them must know eachother. Before you knew it attention is back on you and a glass of wine is between your palms. 'okay relax Y/n, just drink some wine, you got this' You told yourself encouragingly, only having it not work. Forcing you to take another big gulp of your beverage.

"So where did you and Carmen meet?" You looked towards the older Winchester and cleared your throat. "I was going to college, got stuck in a rough time and he was the only one who was able to snap me out of it." You gazed upon Dean's facial features, "And how long have you known Dimitri?" His tone darkened and you swallowed. "About three years."

The two men looked at each other, almost like it was their own little secret language. Suddenly your mouth was dry and you picked up your drink. After a voice spoke to break the tension. "What'd you go to college for, gorgeous?" Sam asked as his long fingers played with the drink coaster he has yet to use. His hazel eyes cast on you, eager for any slight movement.

They were studying you, quite closely. You had no intention on telling them the whole truth. Yet as you opened your mouth to speak it had a mind of its own. "Journalism, I was pretty passionate about the truth when I was in college." It was silent and your tongue came to moisten your bottom lip. It wasn't until about ten seconds going by, did you realized their intense and slightly skeptical gaze on you.

"Alot of psychedelic hangovers in class though, so I didn't end up learning much." You laughed a little trying to ease the thick fog. Sam's mouth quirked up and his hand came to cover his amusement. While at the other side of the table Dean was looking at you with an intrigued smile and bubbly laughter.

When the food came you were surprised at the differences in their diets. Dean was pounding a triple meat home style, and the younger Winchester was nibbling at a vinaigrette salad with some unsalted fries. You settled for onion rings and a soup. "Do you mind if I ask you what you guys do?" You asked timidly.

Though the two of them faltered for a short second. You took a breath and held it unnoticeably. "We don't do much," The older Winchester sat up higher and straightened his over coat once again. "Exchange stock mostly, invest. Occasionally we buy properties."

Sam leaned back and ran his hand threw his hair. "Selling land, trading stock, it's the family business." His routine like smile had you filing the conversation in the back of your brain.

You pouted, "So when do you guys get a break from all that?" It has been a while now since the food was finished, Jo coming and grabbing the dirty dishes from the table. She spoke out as she was placing the check on the table, but the three of you were to involved to have heard her over the rest of the restaurant. "Whatever breaks we do get you'll hear from us." The vague not-answer left you with an urge to roll your eyes.

Trying to pry out their information is proving to be a lot harder than you first believed. Not to mention now you couldn't hold all theirs words as true, their knowledge of you being a journalist was not helping you in this case. So at the moment it's best not to try your luck. Quick ask something else, "A-and what would we do on these breaks huh?" You took a sip of your wine and it gave you more courage.

Sam chuckled, meeting eyes with his brothers once more. "C'mon, Y/n you look like a smart capable woman." Dean slipped a bill into the check book and stood. The veins in his hand popping out in the slightest as he adjusted his belt. Sam standing shortly after and loosening his tie, bottom lips between his teeth lightly. The elder winchester held his hand out to you and you timidly took it.

"Let me show you what we mean."