Random Fandom Imagines 2

Teenage!Dean Winchester

The blaring sound of your alarm pulled you from sleep as you groaned loudly before violently slamming your hand on top of it thus shutting it up. You laid in bed for several minutes before pulling yourself to your feet as it was part of your normal Wednesday routine.
You got through all of your normal morning tasks with record speed before getting in your car and driving to school.
As you walked through the halls you were surrounded by giant poster boards and screaming girls as guys of all ages admitted their crushes in hopes of escorting them to the homecoming dance.
You had to admit that it did put a smile on your face. To be surrounded by happy couples who were asked out through cleaver rhymes and cheesy puns that the guy most likely found on the internet was an intoxicating feeling. Though on the other hand you couldn't help but feel a small twinge of jealousy.
Sure when you said small you meant small, like barley able to notice it was even there small, but nonetheless it was there. Dean had yet to ask you to homecoming and with it only being two days away you were beginning to doubt that he was even going to ask.
It defiantly wouldn't surprise you if he didn't ask you but instead just assumed the two of you were going together. Which of course wouldn't bother you, you had been dating him for quite some time and were more than happy to find yourself in his company, you couldn't deny the girlish fantasy that every teenager had of their crush asking them to homecoming with the very signs that lined the hallways, a fantasy that for some did come true.
You also couldn't help but wonder if this would be asking too much. It was still a shock to you that the eldest Winchester liked you for you had had a crush on him since the young age of twelve when you, his brother Sam, and he would sneak out of your houses in the middle of the night to watch the stars. Though you often found it boring, it's not like the stars were moving before your eyes, you were always more than happy to do it if it meant you could lay next to Dean, a thought that at the time you didn't know Dean knew all too well.
And so it was with this thought that you pushed all doubts away and swallowed all jealousy and walked to your locker with a high head. You were going with Dean to the dance no matter what, even if you had to drag him there in one of his flannel shirts.
With thimble fingers you quickly opened your locker not even noticing the small bear clutching a red heart in its paws at first. You put your books in accidently knocking over the bear. You caught it, however, before it could hit the ground.
Your eyebrows were scrunched up in confusion as you slowly turned around to see the entirety of the varsity football team standing behind you. Half of them holding up a giant sign the other half simply standing with their hands in their pockets and dumb grins on their faces as they looked at you.
You felt your cheeks heat up and a small smile cross your face as you scanned the team looking for Dean, who was nowhere to be found so instead you turned your attention to the sign. It read "I couldn't bear the thought of going to homecoming without you".
You bit your lip to stifle a giggle as you looked down at the bear in your hands, though it was a dumb pun it was incredibly sweet, which was weird considering Dean never let his guard down in front of others let alone the football team.
The kid on the end held up a single piece of paper, printed on it was a large arrow pointing to his right. Out stepped Dean Winchester in all his glory. You nearly laughed as you saw that his posture was uptight and rigid and the tips of his ears were pink. Clutched in his white knuckles was a bouquet of flowers which only caused your grin to widen.
"Dean Winchester when did you get so soft?" You teased causing the redness in his ears to spread to his face as the football team all went 'ooohhhh'.
"I mean if you don't want the bear I can take it back." He responded with a smirk on his face as he held out one hand.
"No no" You said as you hugged the bear closer to your chest as more and more people began to crowd around you. "It was a gift from my homecoming date"
It took a few seconds for everyone to process what you had just said before the entire hallway erupted into cheers. Dean strode towards you and engulfed you in a bear hug, spinning you around in a circle as you laughed.
Once he had set you down he placed a short soft kiss on your lips before turning back to the hallway and holding up your hand for everyone to see. "SHE SAID YES" He screamed only causing everyone to cheer louder as your face got redder.
"Ok well I've got to get my homecoming date to class" Dean said looking down at you with a soft smile that made your heart melt. Reluctantly the crowd thinned down so that you and Dean could walk to first period.
"You got the entire football team involved?" You chuckled as you watched them all mockingly 'awww' at you and Dean.
"Hey being the captain has it's perks." Dean chuckled as he let go of your hand and instead draped it over your shoulder. "Were you worried I wasn't going to ask you?" He smirked.
"I just assumed we were already going together." You shrugged, it was half true after all.
"So I didn't have to go to all of this trouble?" Dean asked in mock annoyance.
"Oh no please always go to all of this trouble." You giggled clutching the bear tighter "It was sweet."
Dean's smile grew as he stopped swinging you around to face him and then bringing his lips to meet yours for a longer more passionate kiss than before "My pleasure"
You smiled into the kiss before breaking it off as the bell sounded above you. Dean frowned slightly refusing to let go of your hand until the distance between you two got to be too great.
You gave him a small wave before spinning on your heel and walking off to class. Dean watched you leave only turning around when you had turned a corner unable to keep the dumb grin off of his face. He couldn't wait for Friday.
-
You sat in front of the mirror as you held the curling iron next to your head. You slowly unclipped it enjoying the way your now curly hair cascaded down over your shoulders.
You heard the doorbell sound, knowing it was Dean, yet made no move to answer it. You could hear the hinges squeak as the door was pulled open. Dean's name left your mom's lips in a high pitched squeal as she no doubt hugged him and your father clasped his shoulder. Your parents absolutely adored Dean.
You heard them all laugh loudly, no doubt at something Dean said, as you leaned forward to fix your make up one last time before beginning the walk down the stairs.
You watched with a smile on your face as you saw Dean's jaw drop. You knew from that simple slip up Dean had only won your parents over further.
You nearly giggled as you approached him, watching as he struggled to form complete words.
"Is that for me?" You pointed at the corsage in his hands.
"Uh-yeah-" He stuttered out looking down at the flower in his hands as if he had forgotten it was there.
You grinned and picked it out of his hands securing it around your wrist.
You quickly posed for some pictures before you were ushered out of the house. Your father not even bothering to remind you of curfew knowing that a you would be home by then and b that Dean would have you home well before then.
You walked around to your drive way stopping in your tracks as you saw the impala parked in it. "You got your dad to give you the car?"
Dean chuckled slightly "Yeah, cost me a week of dishes but only the best for you."
"Awwww" You teased him causing him to chuckle and roll his eyes.
"You know at this rate I'll just stop doing nice things for you."
You laughed and held up your hands in surrender as Dean held the door open for you, always a perfect gentlemen.
-
You nearly screamed as you heard the sound of your favorite song blast through the door. You gripped Dean's hand tighter and jumped up and down slightly causing him to chuckle as he gave your tickets to the teacher.
As soon as he was done you pulled him into the dance as fast as you could. In seconds you were on the dance floor bouncing along to the beat of the music. Dean stood back and watched you with a soft smile on his face.
"Come on Winchester dance with me." You grinned taking his hands and bouncing them up and down.
"Give me a second" He chuckled before walking further into the crowd of people leaving you to dance by yourself.
You bounced awkwardly by yourself as you looked at the people around you. Suddenly there was a stop in the music. You drew your eyebrows together as you looked around, a chorus of boo's surrounding you.
Suddenly the silence was replaced by a slow song. Couples all around you suddenly began to dance as everyone else immediately fled the floor. You searched in vain for Dean before deciding you had better get off of the floor before people started to stare.
You bit your lip and looked down at your feet. However before you could move you felt a hand grab your hand pulling you into someone's chest. You looked up to see Dean staring down at you with a small smile on his lips as he placed his hands on your hips.
Without even thinking about it you wrapped your arms around his neck and stared up into his eyes. You felt his hand leave your hip for a moment before he put it back. You took a quick look over your shoulder just in time to see the DJ shoot Dean a similar thumb up.
You chuckled and looked back at him to see him staring at you. "Did you do this?"
Dean only shrugged before pulling you in closer pressing his lips to yours. You dissolved into the kiss before pulling back and laying your head on his chest as Dean swayed your back in forth, every once in a while pressing a kiss on the top of your head.
All too soon the song ended and you were forced from Dean, a frown painted across his face. You offered him a smile and began to jump up and down slightly as the beat of the song picked up. Dean began to sink back towards the wall, never one for dancing.
You rolled your eyes before chuckling and walking up to him. Your grabbed both of his hands and brought him closer to you so you wouldn't have to yell. "How about we go get a milkshake instead?"
Dean raised his eyebrows in shock "Really? Are you sure?"
You grinned nodding your head "I mean I got to dance with you, what else could I want?"
Dean immediately grinned and pulled you in for a hug. You happily wrapped your arms around him as he placed a kiss on top of your head.
You smiled before allowing him to guide you out of the school, an arm wrapped protectively around your waist as the two of you fought against the crowd of people heading in.
You may have spent hours trying to get dressed up and look good but as long as you were with Dean you were happy.