Supernatural Imagines 2

{39} Dean

Requested by: BabyDino1

Imagine: Dean and Sam's best friend and one night you wake up and go and sit on top of the roof and Dean follows you. Soon you both confess your feelings for one another.

It had been seven long years since you reconnected with the Winchester brothers. You had known them when you were all kids. Your dad had been hunting partners with their dad. You were two years younger than Dean, two years older than Sam, and you all got along amazing. 

You stayed with the Winchesters for a period of time and had even begun to develop feelings for the eldest brother. But then, one day, they all just disappeared. You were fourteen at the time. You didn't hear anything from them or about them for the next decade of your life. 

You tried getting in contact with them, but no one claimed to have ever seen them. You gave up after a few years, figuring that if they wanted you to find them, you would have already. You distracted yourself with hunting, and that worked, for a while. 

You believed you had actually forgotten about the Winchesters. That was until one day on a hunt, you ran into them. You remember that day so clearly. 

~

It was a Friday afternoon. You were just leaving an Alabama police station. You were gathering information for a case. You were pretty sure it was a couple of werewolves. You were walking down the sidewalk, towards the hotel when a strong arm pulled you into an alley.

You let out a small gasp before your instincts kicked in and you began fighting the thing in front of you. It immediately fought back until it pinned you to the ground, straddling your hips. You looked up and locked eyes with the one and only Dean Winchester.

"Hey, sweetheart," he said, his charm ever-present. "Dean," you breathed out. He got off of you and helped pull you to your feet. "Wanna get a drink? Catch up?" he asked, his classic smirk resting on his face. 

"Did you really think that was going to work Dean? Disappear for a decade and then make it up with a drink?" you asked, looking at him in slight disbelief. Dean's smirk faded as he looked down at his feet.

"No...I just. I missed you," he replied, reconnecting his eyes with yours. You let out a small sigh and silently debating your course of actions. "Sammy's at the bar too, you know. He'd really like to see you," Dean told you, in hopes of convincing you.

You looked at Dean and hesitantly agreed. Dean tried to hide his smile as he led you to the bar. When Sam saw you, he immediately embraced you in a hug, telling you how much he missed you.

The three of you spent hours in that bar just catching up and you didn't realize how much you missed them, and how much they had meant to you. Unfortunately, that also meant you didn't realize how much you had fallen for Dean Winchester.

Talking him to him that night, it brought back all of your old feelings for him. You didn't mind it at first until you realized that it was only a matter of time before you had to say goodbye. Knowing that you decided to leave the bar right then and there. The sooner you said goodbye, the better.

But, that plan failed when Dean and Sam asked you to help them with the hunt. You agreed and after the hunt, they even asked you to come with them. After much thinking and hesitation, you agreed, knowing you wouldn't be able to say goodbye to either of them again.

~

You had been with the Winchesters since that day and had only grown closer to them. You knew that every day you spent with Dean, you only fell for him harder, but you knew he never felt the same. Why would he? You were nothing compared to all the beautiful women he picked up at bars. 

It had been a while since Dean had hooked up with a random woman. You all moved into the Men of Letters Bunker and since then Dean's been more focused on other things. Hunting things. You couldn't distract yourself from Dean with hunting though.

You tried to, but nothing worked. 

You were in your room, laying on your bed, thinking about these things when you decided you needed to be somewhere else. You had no idea where the Winchesters were, but there was one place in the Bunker that you absolutely adored -- the roof. 

The Bunker had a secret staircase to the roof, and you have always loved going up there. It was peaceful and quiet. You began walking there, unaware that a certain Winchester was following you. 

When you got to the roof, you sat down, letting the cool air relax your muscles. "Don't you dare jump," Dean said sarcastically as he came closer to you. You smiled up at him a little before looking back at the view in front of you.

"What are you doing up here?" he asked as he sat down next to you. "Getting away," you replied. "From?" he questioned. "Everything. This is a good place to just forget it all," you responded. Dean nodded his head, letting you know he understood. 

Sitting there with you, Dean couldn't help but stare. "What are you looking at?" you asked with a small chuckle. "You," he replied, making you lock eyes with him. "You're beautiful," he told you. A blush crept onto your cheeks, and you looked down, trying to hide it.

"Dean...I," you began, wanting to tell him everything, but his friendship meant too much to you. "What?" he asked, sounding hopeful and desperate as if there was something he wanted you to say. Something he needed you to say.

"Nevermind," you replied, looking at down at your feet. You couldn't tell him. It would ruin everything. Dean let out a small sigh of disappointment and there were a few moments of silence.

You looked back up at Dean, but before you could say anything, he locked his lips onto yours. You were taken aback for a moment, but quickly responded to the kiss, moving your lips in sync with his. Dean placed his hand your cheek, pulling you closer. 

After another moment, you both pulled away, breathless. "I love you," you blurted out. Dean looked at you for a moment and your heart was skipping beats as you waited for Dean's response. "I've been waiting to hear you say that since he was fourteen," he told you pulling you into another kiss. A kiss that felt so right. "I love you too," he told you and the grin on your face said the exact emotion you were feeling. Pure happiness and bliss. And on Dean's face, you saw the exact same emotion.

Hello my little monsters,

Thank you all so much for reading. I hope you all enjoyed. I love you all and all of you are amazing!

Always Keep Fighting!

~Caela

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