Dean x Shy!Reader: Best Friend's Brother

"Do it," whispered Sam, nudging you towards his brother. You groaned and slapped him on the arm. You looked at the older Winchester and then quickly looked away. Dean was currently on the couch, looking through newspapers for the next hunt.

You had a crush on him, you see. But of course, you were too shy to ask. Sam knew that right away since the two of you were best friends. You became friends really quickly when Sam moved into your high school and protected you from a couple bullies. You then told him that no one had ever done that and you would be glad to be friends. And from then on, you stuck by him and he protected your from any bully. He had told you that he had a few bullies that bullied him as well so he was glad to help you.

You were always a shy one. Especially when it came to Dean. But Sam had tried to make you talk to him, but you always ended up not saying anything or ending the conversation right away. But that didn't stop Dean from trying to start a conversation with you.

"How would you know that he doesn't like you back?" Sam whispered, turning around and walking into the other room. You followed, rolling your eyes.

"Because if he liked me back, you would have asked him to make the first move. You know how terribly shy I am," you whispered back, slumping onto the couch. "I can't believe that you would let me crush on your brother! Aren't you afraid that I'll break his heart or something?"

"You? Break his heart? Like you said, ___________, I think you might be too shy to do so," Sam laughed. "And I think Dean has a higher chance of breaking yours. And I wouldn't let him break your heart since you're my best friend. But of course, I'm not going to interfere. He's your 'one and only love'," Sam quoted. You threw a pillow at his head, him easily dodging it.

"Whatever, Winchester. I hate you. Go to hell," you mumbled, burying your head into a pillow. Sam chuckled.

"Already been there," was his reply. You threw another pillow towards him and he caught it in his hand and placed it beside him.

"Smartass. You know what I mean," you grumbled. You then hear footsteps entering the room.

"So, what are you two besties up to? Gossiping?" Dean asked, sitting on a chair, across Sam. You groaned loudly as you didn't move from your place. Sam laughed and shook his head.

"_____________ is just upset. Don't worry about it," Sam stated before you could say anything.

"Upset? Why would little ____________ be upset?" Dean asked. You sat up and stared at the older Winchester.

"Because Sam is being mean!"

"Why is he being mean, exactly?"

"Because he keeps pressurising me to try to tell you I like you!" You blurted out. The moment you realise that you said it, you covered your mouth. Embarrassed, you fell back on the couch, with your head buried in the pillow. You could literally hear Dean smirking right then and there.

"Aww, has the sweet little _____________ developed a crush on me?" Dean asked, in a tone that kinda irritated you. You just huffed and looked away.

"Why would you want to know?" You asked. You crossed your arms as you refused to look at Dean in the eyes.

"Because. I may or may not like you too," now at that statement, your head snapped towards the older Winchester with wide eyes.

"Don't joke with me, Winchester," you said with slight anger.

"Hey, hey, I'm only telling the truth," Dean said, holding both hands up.

You still didn't know what to say but you felt your heart squeeze as you rethought about him telling you that he liked you.

"O-Okay..." You started. "So what do you want to do about it?"

"You're asking me? You're the one that confessed first." Damn him and his stupid mouth.

"So do you want to..." You trailed off.

"Sure. We'll just head to my bedroom. Don't be so loud, okay?" Dean teased. You felt your cheeks redden and heat up.

"Shut up! I didn't mean it that way," you pouted. Dean chuckled as he scooted over next to you. "I meant... Do you want to go out with me?"

Dean gave a genuine smile as he leaned in and gave you a soft kiss.

"Sure," as he kissed you again. From across the room, you hear a distressed Sam.

"Oi. If the two of you want to get freaky, go to the bedroom. I don't want to see anything stained."