The Unrequited (Dean x Male Reader)

Just Us

"Well, that was one hell of a dinner," Dean said as he closed the door behind him. You sat down on the bed with a sigh. You had come to meet a family friend of the Winchesters' and were staying at their place. While Sam and John had adjusted in the living room, the guest bedroom had been given to you and Dean and even though you felt a bit guilty, you shoved it off and thought you at least deserved a bet to sleep in after having gotten a gun pulled on you.

You didn't say anything as you rested your back and just closed your eyes, thankful for the silence. Just as you had gotten into the house, you had pretty much been surrounded by everybody and boy did they like asking questions. This continued throughout and having had John keeping a close eye on you, you had held Dean's hand almost throughout and had kissed him a couple of times and once on his cheek when the others were busy in conversation, though making sure they saw you.

"You tired?" Dean asked as he took his shirt off and put it over the chair in the room. He still had his undershirt on. 

"Yeah, that was a lot." You said. "I don't think I'll be able to sleep though," You said as you adjusted on the uncomfortable mattress.

"Yeah," Dean chuckled. "You were out throughout the ride on the way here." He said and walked across the room to look outside the window. "It's pretty breezy outside," He said after a while. You opened your eyes and saw him standing there, staring out of the window. He looked at you and your eyes met for a brief second before you awkwardly shifted your glance to the other side of the room and realized you hadn't even looked at the room properly. It wasn't much and felt like an untidily kept room that was only quickly fixed for you. "Say, you want to hop out for a ride?" Dean asked and when you looked back at him, you saw that he actually seemed nervous. 

"Okay," You said before you thought it through, mostly out of guilt seeing Dean actually try with you. Dean grinned and grabbed his jacket, putting it over his undershirt. You got up and took your jacket as Dean walked to the door of the room, "Wait, won't Joh-" You stopped, "Won't dad say something?"

Dean looked at you but didn't say anything for a minute. He thought over it, Dean was sure that John would probably be happier if anything to see you go out with him and wouldn't say much but did he really want to see that 'nod of approval' again? He was tired of it, tired of the act, tired of being forced into a dynamic that he was supposed to act a certain way in and prove to his dad that he could be good. "Want to sneak out?" Dean asked with a raised brow, nodding towards the window on the other side of the room.

"Um," You looked at the window and back at Dean. You had snuck out a lot of times before but the picture of John's gun did make you want to ask John first. 

"Oh, come on," Dean's grin was back as he walked towards the window and opened it fully. It seemed wide enough for both of you to climb out of and you'd only need to climb down as you were on the first floor. 

"Alright," you finally said and followed Dean. Though still a bit unsure, you couldn't help but smile. It felt exciting, especially since this time you weren't sneaking out because of frustration, and also that you had someone to sneak out with. 

Dean hadn't sneaked out much, except when his dad was with them. He had always been the elder brother and had to stay at the motel with Sam to keep a watch growing up, especially after that one time when a Shtriga had attacked Sam while Dean was out when they were younger. "Wait, I'll go first," Dean said and climbed out of the window as he carefully got down and then signalled for you to come. You looked back at the door of the room and then climbed out, closing the window but keeping it slightly open so you could open it when you came back. You carefully descended as Dean grabbed you and helped you down.