The Unrequited (Dean x Male Reader)

The Winchesters

"You've got your things packed?" Your Dad asked. You nodded, keeping your eyes down. You were surprised when he hugged you, "It'll be okay, I'll see you soon. Just do what they say. I love you."

You didn't say anything to him and just stood there, not looking at his eyes even once. It'll be okay? You wouldn't exactly give your dad the father of the year award but he had just stooped to his lowest level. What he even thinking? He had offered John Winchester his son, you, to pay off all the debt and things he owed him. Well, that's what your Dad told you anyway. You were well aware of the debt and how it was bothering your dad so much but to sell you off as help to just some family? Nonetheless, you felt a relief that you'd finally be getting away from this place. 

You had spent almost all your life either locked in your dad's car or some shitty motel if God decided to have some mercy on you. He wasn't even a good hunter, just drove around different towns and cities to investigate and hand over the case to some other hunter nearby only to then retort to some old bar while you spent the night in the car. Your mom had always been the 'My kid won't be a hunter like us." person and had left your dad with a promise to keep you away from hunting when she died. So instead of actually doing something for you, he just dragged you around with him not letting you out of the car or the motel while he "did all the work".

Your dad smiled at you, almost apologetic but it really just looked pathetic on his face. He opened the door walked out as you followed behind after he broke the embrace. 

"Ah." You heard a man's voice and looked up to see John Winchester smiling brightly as he greeted your dad. You didn't have to look too far to see another man, probably in his early twenties, leaning over a car. You looked at the car with awe and how well kept it looked, considering it had to be vintage from judging its style. His eyes were fixed on you and you looked back down again when your eyes met.

"You can keep your bags in the back." The man said as he opened the trunk. Probably John's son, you guessed. You nodded and walked up to him, keeping your bag in the trunk like he had said. On your way there, you overheard a bit of John's conversation with your dad.

"Don't worry, my son will take good care of him."

"That's all you got?" The man asked and you looked up at him this time. He was fairly taller than you and looked genuinely happy as you judged from his smile, which made you wonder if it was really a hunter family or not, though the Winchester name was quite famous. You hadn't seen a hunter in your life smile as much and both John and Dean had smiled at you. You nodded and he closed the trunk and looked at John who was still talking to your dad before turning to you, "I'm Dean." He said with a smile.

"Y/N." You said. Your face was blank and you just kept looking at Dean's face. You weren't used to people smiling at you, let alone a hunter. 

"How old are you?" He asked. You told him about your age. He was a bit surprised, saying you looked younger than you were but didn't tell his own age. Though he seemed only four to five years older than you were.

"Getting together well?" You heard John's voice and turned to look at him. Then your eyes shifted from him to your father who was nowhere to be seen, how typical of him, you thought and sighed. "Come on now, let's hit the road," John said and patted your back, guiding you to the backseat.

You took your seat. John took the driver's and Dean had shotgun. "You can drop me at Bobby's for a couple of hours. Take him around the town for a while, get to know each other. Yeah?" John spoke to Dean.

"Yes, sir." Dean said. You couldn't help but scoff in your mind. Guess it ran in the hunter's tradition, the whole "sir" business. It both frustrated and amused you how the world's most broken families were pretending to have their shit together just by keeping some idiotic southern traditions going on.

"So... Y/N, you like my son so far?" John asked you, looking at you through the rearview mirror.

You wondered what John meant by the question but went along, "Um, yeah. I mean I do, Sir."

John chuckled at that. "Good, good. I see James taught you some manners alright." You knew John had meant it as a compliment and it came from his heart but it still disgusted you, to even think just you calling someone "sir" made your dad a good father out of the blue. "But you can call me dad." John added.

"As you say, si- I mean dad." you said. It felt weird but you had to do as they said, so your dad had told you and it didn't look like you had any other chance. The man was miserable with his debts and the last thing you wanted was an angry hunter at your trail for the worth he didn't get for the money he paid.

The rest of the ride was silent. John stopped in front of what looked like a small house surrounded by tons of cars and got out. He told you to come to the front as Dean took the driver's seat and you did as he said. Dean drove off once John walked inside. "Bobby is an old family friend, great guy. You'll love him. Everybody does." Dean said, looking at you with a smile.

You merely nodded. He stopped in front of a diner after a while but didn't get out. So you kept sitting there as well, looking out of the window. You rummaged the area which honestly seemed rather deserted. When you looked back at Dean you noticed he was looking at you as well, as if he had been waiting you to look to his direction. Suddenly Dean leaned in and kissed you, leaving you confused and a bit rattled. But didn't say anything. Dean got out of the car after that and so did you. You followed him into the diner and took a seat across from him in a booth. He ordered for the both of you.

"You don't talk a lot?" he asked with a smug on his face.

You shook your head, "Dad taught me not to."

Dean gave an apologetic smile, almost as if he understood it quite too well. "Well, you can talk all you want now." he said. "Got any questions?"

You gulped and hesitated a bit but decided to speak up anyway, "Why'd you kiss me in the car?" you asked.

Dean only chuckled to that, "Right. Are you a virgin?"

You narrowed your eyes to the question, "I- no, I'm not." You answered.

Dean smiled and nodded, "How do you like it then? Not that we have to talk about it all just now, we can always fine out later."

You opened your mouth to say something but didn't. You didn't know what you liked (you had only had sex twice and were still unclear about what you really liked) or why he was asking so in the first place. So you just nodded.

"Alright, I'm sorry. Whenver you're comfortable, we can talk about something else if you want. Oh, and don't worry. I won't do anything until after the wedding. Strict orders from dad."