Charity Case | Sam & Dean Winchester

Chapter Three: Personal Driver

The man you'd seen in the dress shop a few days earlier was staring down at your purchase. Or more so Dimitri's. His gaze never faltered and his eyes glinted every so often as he raked them up your appearance. Somehow you had liked it way better than when Andrew was doing it. He had removed his mask as he introduced himself. "I'm Sam, and you are?"

His breath smelled like the fruity punch on the serving table, but you didn't mind. You smiled shyly at him and reach out to shake his palm. "It's nice to finally meet you properly Sam, I'm Y/n." His smile widened and he brought your hand to his lips. "You have a very beautiful name." He was the taller of the two you'd seen and he had to bend in the slightest just to feel your skin.

When he was done you reached to remove your own mask, though before it could come off Carmen and your ride for the night came rushing towards you. Sam's face lit up in recognition at Dimitri. "D-tri! Long time no see."

The last part of his sentence was spoken lower than the beginning and Carmen had placed his arm around your shoulders as if to pull you away from some sort of danger. You furrowed your brow confused but as your eyes wondered Sam's outfit, you'd found a golden clip that folded on the cuffs of his sleeves. An imprinted 'W' in the middle.

As soon as you realized who you were speaking with your heart picked up speed. Only a few minutes into the conversation and you had already gotten his first name. You shook off the arm that seemed to weigh you back. "Oh! I didn't know the two of you knew eachother?" You said before you could stop yourself, hoping to confirm your suspicion of the mysterious man.

Sam towered over Dimitri, pulling him into a hug as if to show you how close they were. Though your friends sugar daddy didn't portray any enjoyment in his features for the former.

"Yes Winchester and I had met long ago on a uh- business meeting, and although I'd love to catch up I was just coming over to let you know we're leaving." You tried to hold your excitement back at the last name, then your disappointment at the statement. "Are you ready to go?" Dimitri gave you a look that screamed out a warning. Yet Sam was quick to answer back. "Is he your ride?" You nodded your head in genuine dismay. "Unfortunately yes, I-I wish I could stay but I don't have any other way back."

A scoff came from behind the tipsy Winchester and Dimitri stiffened his jaw. "Oh it wouldn't be a problem if we escort her home ourselves, would it brother?" A calloused hand made its way to Sam's shoulder and he shook his head. "Would you mind that Y/n?" You grinned naively, hearing your friend emit a low frustrated groan. You had a feeling this was Sam's older brother, he seemed more reserved and careful.

While Sam's breath wreaked of the punch, his brother had on an expensive cologne that had your mouth watering. "I would love that, thank you." Sam's brother had yet to remove his mask, and you were eager to remember the rest of his features. Sam waved the two you arrived with on their way, with a slight teasing wiggle to his fingers, before pulling you towards a table perched high on a platform.

You felt many eyes on you this time with whispers trailing not far behind you, ones that the Winchesters seemed to be oblivious about, or neglected purposefully.

They had you sit between them and all of a sudden the power balance had shifted; You were no longer in the conversation to collect information, they were. "Would you like something to drink, sweetheart?" The elder Winchester asked. You nodded your head reluctantly, deciding you needed a little liquid courage if they were going to devour you with their eyes all night.

"What made you decide to come here?" He had gotten straight to the point while Sam held up the waitress with his order and yours. "I was relying on my roommate too much with rent money and they suggested I come along with them here." He nods his head sitting back in the booth, "What brings you here?" You questioned back, struggling not to bring your nails between your teeth.

"Looking for rent to pay." He avoided the question easily and you tried not to deflate at the deflection. Sam was awfully quiet now sitting back and watching your interrogation, "I'm going to guess Carmen's your roommate?" The brothers share a look as you confirm, "Dimitri's a good guy, almost too good." Said Sam and the brothers chuckle and drink from their cups. "He is, he helped me prepare for tonight."

The smile never wavered in the older Winchesters face and he cleared his throat. "Have you ever had an arrangement like this before Y/n? Assuming you'd like an arrangement with us." You were hesitant to answer but as you looked back and forth from Sam to his brother they both have caught on to the answer already. "I have not, a-and yes." It's too good of an opportunity to let go. The younger Winchester moved to throw his arm above your part of the booth and asked a question of his own finally.

"I'm curious what you would expect from something like this?" His finger and thumb took a piece of your hair and twirled it between them. Your breath halted and suddenly you were very aware of the two attractive men that sandwiched you. Looking down at you with a sort of predatory gaze.

His eyes once again looked towards his brothers and it seemed to encourage the mask to come from his face. Sam's fingers tracing your own mask lightly, before slowly lifting it. Once it was done hiding your expression, you found it hard to keep their stare. Sam's rough hand caught your chin and rose your gaze to his. "What I expect isn't much at first, my brother Dean is the same way. Just don't get nervous on us now doll." He brushed your bottom lip and you involuntarily opened your mouth to let a breath slip through.

"I-I'm not." You squeaked, completely losing your original objective and turning into a blushing puddle. The two chuckled in unison and Sam sat back watching Dean scribbling something down on a small piece of paper. They looked to be numbers.

"I'd love to have a longer chat about having an arrangement, but unfortunately it's getting a bit late for me. And as I'm sure you've noticed my little brother has been drinking." The smile on Sam's face as he was mentioned had you carrying one yourself. He moved the paper your way, the younger Winchester leaning over the table.

"Call us, when your thinking about me." Sam winked and you couldn't help but chuckle above the new found heat on your cheeks. "Or me." Dean had thrown in with a husky voice. The younger Winchester didn't seem to like Dean's input, turning and motioning to someone a bit aggressively.

A large man came up to the table and the boys shuffled out of their seats. "Time to get you home." Dean reached out to assist you and you scooted out along after them. The piece of paper clutched tightly in your hand as a personal driver asked for your address.
When you told him, the older man gave both the boys behind you a long look before a sigh escaped his lips and he motioned for you to follow him.

His look was uneasy and beyond curious.