Dean Winchester One Shots

By neahann

62.6K 1.4K 399

Cute short stories about Dean and Reader. They are mixed with sad and fluffy. [Requests Open] More

All Wrong
Defensive At The Motel
I Wouldn't Mind
The Moose Knew
A/N: 300?!?
Oh, The Cold Snowflakes
The Man In The Impala
Breaking Up In A Small Town
High School Love
Sweet Perfume
Forgetful
Man Down
Q&A? 1 Year Anniversary?
If You Love Me Let Me Go - Part 2
It's For The Better
Pictures Contain Many Memories
Goodbye Dean Winchester

If You Love Me Let Me Go

2.6K 60 28
By neahann

~Dean and the reader are teenagers~

It's your first day at your new school, and you are nervous. Will the kids like me? What are they like? Where are all of my classes? What is RTI? Oh no.

You walk down the halls looking down, trying not to make eye contact. You look up for a quick second and you see a couple of girls walk towards you.

"Hello, I'm Kady!" The girl with the long brown hair yells at you.

You internally groan but politely respond, "Hey I'm Y/N!"

"Nice to meet you, do you need help getting to your classes? It's really confusing here,"

"Yeah, yeah that'd be nice," You smile. At least you have a friend, well, maybe.

Kady showed you all around, the building was huge but it was very nice. You both had all of your classes together, even your favorite class.

Once you both went to lunch in the huge common area with kids that yell at each other over the noises of the kitchen. As you sat down one boy was looking over at you. He was very attractive, well that's not even a good word to describe his beauty. He has dirty blonde hair and bright green eyes, he had a nice flannel shirt on and plain dark denim jeans. He looked pretty clean unlike the other boys in the school.

"Who is that?" You ask Kady.

"Oh, that's Dean Winchester,"

"He's pretty cute," You shrug trying not to sound like a fan girl.

"Yeah I guess, he's been in this school only for a month. Nobody really knows much about him, only that he takes care of his little brother and he drives an Impala '67 all over the place,"

"Oh," You say quietly and look down, ending the conversation about the mysterious Dean.

After lunch was over you walked to your locker to get some books for your English class as you feel a tap on your shoulder.

"Hey, miss what's your name?"

You turn around quickly to see Dean right next to your face, "Oh hey, um"

"You don't have a name huh?" Dean chuckled.

"Oh sorry, I'm Y/N" You smiled shyly.

"Well Y/N, how about going on a date tonight?"

"What?"

"I said, you me a date tonight?" Dean laughed.

"Oh yes, sure," You stammered a bit shocked, but happily agreed to the date.

"See you tonight Y/N," Dean winked and waved goodbye.

You stood by your locker shocked, that was awkward but hey you got a date.

~Le time skip to date~

"Y/N, can you guess where we are going?"

You looked out the Impala's window for a while before answering, "I have no clue,"

"Good," Dean smirked before pulling down a back road.

You watched him, he smirked as he drove. He'd whistle to his old rock music and sing along.

"So, what's your back story?" Dean asked.

"Oh well, I don't really have one. My parents got a job out here, so we were forced to move. I was raised in a small town, there wasn't even a fast food place there or really anything. It was quite boring and the people there were, well you know, pretty much assholes to me. I wish I could've brought my best friend," You looked down remembering your best friend.

"What were they like?"

"They were the best person you could ask for, they would listen to me when I was down and supported me when I needed it most. They would always make me laugh with their stupid jokes and puns, even though I acted like they weren't funny oh hell they were. They weren't like the other people, they were talented in art and writing stories, like fan fiction you know? We used to hang out a lot, because I was moving and we didn't have much time, but it was fun. It was hard to say goodbye to them because it was going to be hard for both of us in school without each other. I really didn't want to say goodbye because it never is,"

"Wow, they seem like a good friend,"

"They were," You looked down, saddened at the thought of being away from them, "How about you Dean? What is your background?"

"Well, I can't top that speech," Dean chuckled, "Well, my mom died when I was little so my dad raised us. It's usually just my brother, Sammy,  and I but we are fine with that. Dad's just really busy all the time,"

"Oh, I'm sorry about your mom,"

"Oh here we are!"

Dean pulled into a nice park that was filled with little kids. It had a walking trail you both went on, it was beautiful. Trees lined both the sides of the road and it had a dirt trail.

You both talked about your lives to each other and found out you both had the same interests. You guys got along pretty well for strangers. After you were done walking the trail Dean took you home.

"Dean, thank you for the date, it was really fun we should do it again,"

"Yeah we should," He did the smile that make his lips curl and showed his teeth.

~Le time skip after many dates~

Dean and you hit it off pretty well and fast. Dean was the first to confess his love for you and then you confessed too. After that he became your boyfriend and you guys went on many cute dates. It was an amazing relationship. Well it was fun while it lasted...

Dean and you were hanging at his house in the living room. You both were sitting on the couch just looking at each other quietly and murmuring pointless things. Then it got serious.

"Y/N?"

"Hm?"

"Can I talk to you about something,"

"Okay, go ahead,"

Dean grabbed your hands, "Y/N, I am moving in less than 3 weeks,"

You were shocked and couldn't take it so you ran out the door. You didn't realize what you were doing but you didn't care. The warm air suffocated your lungs, but you kept running until you got into the middle of the street then you collapsed on the ground. Your whole world was shattering, the man you loved was leaving you like how you left your friend but your the friend this time. You kept sobbing and screaming, you felt a pair of hands pick you up and hold you close. You sobbed into Dean while he held you in the middle of the street with no cars in sight.

~Le time skip~

You did what you exactly did with your best friend, spent a lot of time with him. You both still went on dates and had as much fun as you could but the days came quicker and quicker until it was the day. The day that you wouldn't see Dean Winchester ever again.

You watched as Dean carried the last two heavily packed suitcases to the Impala. He looked at you and did a tiny smile as he threw them inside.

"Y/N, I am going to miss you. I love you and always will, don't forget that. You have brightened up my days that seemed so dark. You helped me through so much and I can't ever express how much I love you with just words. To keep it short I love you,"

"I love you too Dean, you helped me through so much too. There's so many things I want to say to you but there's not enough time. Goodbye Dean Winchester, I hope you have a good life,"

"Remember Y/N, it's never goodbye," Dean kissed you for the last time.

"Goodbye," You whispered as the Impala drove off carrying your soul mate away from you to who knows where.

~Le time skip, Dean and reader are adults~

You were working at your dream job, you didn't have a husband and definitely didn't have any kids. It was rough after Dean left, you never dated after him and you mostly stayed home not wanting to do anything with your friends. They always worried about you but you told them you were okay and don't worry about it. Things got better when you graduated college and got a job. You never saw Dean Winchester after he left when you were a teenager.

You were walking home after you got off work when you heard a familiar sound of a car come down the road. You looked up as the car stopped next to you with a dirty blonde, green eyed man looks at you.

"Hello, Y/N,"

"Hello Dean,"

A/N: I hope you enjoyed the story! This is dedicated to my best friend ray____chulllllll I hope you like it as well. I would also like to say thank you for 6K! That's amazing, you guys are amazing as well. Thank you again :)

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