Dean Winchester Imagines

Knight in Shinning Armour

You were screwed. Almost 10 years ago you got out of the life. You had sold your soul to a demon because there was no other way. Every single demon you had exorcized was after you so you sold you soul to the king of Hell Crowley. 

Crowley made a few exceptions. He said two months before your time was up a demon would come and hurt you badly enough to put you in the hospital or in a coma. You agreed but you said that you wouldn't kiss him so you had to sign this really long contract that you had to read all the way through to make sure you weren't getting yourself into something you weren't ready for. 

The time came, the demon was already barged into your place and charging at you.  All of a sudden 2 men wearing plaid and ripped jeans busted through the door with shotguns. The taller one started chanting in latin while the shorter one pulled the trigger releasing a shower of salt.

Black smoke came out of the man's mouth as the taller one finished chanting. you don't think that they even noticed you were crouched down in the corner of the kitchen. 

The shorter one with lighter brown spiky hair looked at you and his eyes filled with worry with the quick glimpse you got before he came over to you.

"Are you okay?" He asked. His voice deep and handsome. You were fairly shocked. 

"Yeah, I-I think I'm okay." You replied shakily. 

"Com'on Sam," the man in front of you said to the taller one. 

Sam came over to you two and put his arm around your side and helped you up. Your knees fairly weak due to the scare you just had. Your knees buckled and you fell into the shorter one. 

"Dean, you got her?" Sam asked the one holding you upright. 

Sam? Dean? Those names rang a bell in your head.  You shoved yourself off of Dean and up against the wall you were against just a few moments ago. 

"Sam and Dean?" You asked with wide eyes.  "The famous Sam and Dean Winchester?" 

"Yeah, that's us. If you are talking about the ones who hunt monsters and everything." Dean said with a smirk. "Wait, how do you know who we are? Are you a hunter?"

"Yes, I'm a hunter, well ex-hunter. Kinda hated the life and sold my soul to get out of it." You said fairly embarrassed. "That's the reason why the demon was here. To remind me that my time is up in about 2 months."

Sam nodded. Dean then said. "Don't worry we have a love-hate relationship with Crowley, we will work something out."

You felt so grateful for these boys, even though you just met them, and they barely knew you besides your greatest mistake. "Really?" They nod. "I guess that means I'm back in?"

"Your choice," Sam said. 

~3 Years Later~

For the past few years you have been living, and hunting with the Winchesters. You've gotten to know them on a professional level and personal. They may seem a tough and all on the outside but in real life, they are just big goofballs. 

But also for the past few years, but it all started when the boys saved you, other feelings besides friendship and a blood bond have blossomed. Dean Winchester being so charming and flirtatious he is etched into your thoughts permanently. No matter the situation. If you are on the verge of death you are constantly worried about Dean, if he is okay, or if he has figured a way to save the day.

Little did you know that he has also been thinking about you. When you were looking through the bunker's library and you tried to get a book on the top shelf and couldn't reach it because you were a fair amount of inches shorter than Sam and he even had to reach to get to the top shelf. Dean just so happens to have walked by and saw your struggle. He ended up helping you but in the process, he was very close to your side and only wearing his black shirt, his boxers, and his robe. Your heart jumped in your chest when he intervened. Being that close to a man who had that type of effect on you made keeping a straight face without having your cheeks flush pink was very tricky. You didn't have a good poker face then but you are still slowly learning.

Personally, he thought it was cute because you were in shorts and a fitted t-shirt that hugged all the right curves, it is your favorite for that reason. But he never took action to the feelings he had. Since you came to live with them, he hadn't slept with any girl from any bar since then. He makes sure that you are safe and ready before you all go out to hunt. He has also become very attracted to the way you always have an opinion for everything and the reason behind it. 

But then the awkward talk in your room happened that set off flairs between you two.

You were just in your room sitting on your bed on your computer watching YouTube when you got a knock on your door. 

"Come in!" You yelled loud enough to where they can hear through the door. But who you thought was Sam asking for some lore about some monster and where to find it since you went through all the books in the library and rearranged everything based on different monsters. You have to admit, you are kind of a book worm. But instead of Sam, it was Dean. Your heart jumped to your throat. "Dean, what can I help you with?" You said nervously, hopefully not very prominent.

"Um..." Dean looked around your room. His eyes falling on an old antique jewelry box sitting on your nightstand that your mother had given to you before she passed away. "Where did you get that."

"My mom gave it to me. She was diagnosed with ovarian cancer about  25 years ago, unfortunately, she didn't make it." You said smiling, you hadn't talked about your mom in a while, it was good to feel that someone cared enough to ask about something like that. 

"Oh, I'm so sorry." Dean shuddered. 

"No need to be ashamed, she was a very brave, proud woman. One day I hope to make her proud." You look at him and his eyes seemed frantic. "What's on your mind Dean bean?" You started calling him that when he called you Y/n the prancing book worm since you prance around the bunker when you are bored. 

"Um, it's just uh," he paused. "I've been thinking about this for a while now."

"How long is a while." You injected quickly. 

"A year." He paused then continued. "I was wondering if you wanted to catch dinner with me some night?"

This caught you way off guard! A date? With Dean Winchester? Holy crap! "Are you asking me..."

"On a date, yes." Dean finished for you crossing his hands. You were silent for a moment. "You know what, never mind. This was stupid."

He went to walk out of your room but you grabbed his hand turning him back around. "Wait! I haven't given my answer yet." You laughed brightening the mood. "Yes, Dean. I will go on a date with you. No need to be so pessimistic." 

His eyes widened with disbelief. His mouth parted with a smile. "Uh, okay then. Uh, I'll start making reservations."

"Reservations huh? So fancy?" you raised an eyebrow at him.

"Fancy, for a special lady," Dean said walking out of your room and closing your door. 

Oh, this is going to be fun.

I want to start getting a little perspective of where everyone is from. So starting with my home country, comment if you are from America.

Okay, so this one was requested by  I hope you like it! I think this may be my longest one yet. Thank you sooo much for reading.  I have decided to start posting on Fridays so that you can read them over the weekend. Please send in your idea I love hearing what all of your ideas! Love you all.