*Dean--Age Year and Six Months*
You got impatient to say the least. Your small hands on the handle of the crib. You decided that enough was enough and climbed carefully out of your crib. You toddled your way to the library, where Sam saw you with a curious look on his face. "Hi Y/n," he greeted you and picked you up in his arms. "Daddy let you out early today." He mentioned before you shook your head. "Did he not let you out?" You giggled and shook your head again. "Did you get out yourself?" He interrogated you before you finally nodded, still giggling.
That's when your dad walked in the room with a confused look, not even fully awake. "Sam, did you let Y/n out?" Dean questioned with grogginess in his voice. "Nope. She decided that she would let herself out today." Sam replied with a small grin. "Jail breaker, huh?" Dean joked and took you from your uncle's arms. "Did you escape from your little jail, you little trouble maker?" You only kissed his cheek. "I'll take that as a yes." He replied.
***Age 17***
You admired yourself in the simple blue dressed you picked out earlier in the month before you wandered the darkened halls of the bunker. Whether or not Dean or Sam didn't approved of the idea of you going to a party, you were going. You're friends messaged you that they were on your road before you picked up the pace of going through the bunker. You reached the top of the steps to the front door before taking a deep breathe, opened the door, and escaped the bunker.
***
You giggled drunk as you opened the door hours later. You were shocked to see the lights on in the main room. Your face dropped a little when you saw Dean sitting in one of the chairs, looking up at you dressed in nothing but the short blue dress that he more than likely would disapprove of. "Young lady," your mouth dried at the stern tone he gave off, "do you know what time it is?" Drunk you is honest you. "Around three-thirty, Daddy," you slurred sounding not so nervous as you were giggly drunk still while you continued to walk down the steps. "Why are you home at this time dressed like that?" He questioned, his tone getting rougher. You laughed a little, the hidden sober you kicking you for how you were acting and answering, "I was at the party with my friends." Dean's expression turned with slight anger, "The party? Is this the party I told you not to go to?" He interrogated as you reached the end of the steps. You put your finger up to your mouth, "Shh, don't tell anyone." Dean rolled his eyes. He knew he couldn't get much more from you. "Okay, let's go to bed." He sighed and helped your straggling feet to your room.
Dean put the trash bin next to your bed before pulling the blankets back on your bed. "I don't think I'll throw up again." You announced with a grin while you put on shorts, after stumbling a few times with your left foot then grabbing a loose t-shirt and unzipping your dress and watching it fall to the ground with ease. "How many times have you already?" Dean asked as you laid on the bed. You chuckled and held up two fingers. "Am I in trouble?" You asked, eyes big with curiosity and small concern. Dean gave a small sigh, "Considering you already threw up twice and it was your first time sneaking out, no. Next time, you'll be in big trouble." Dean answered. "Now, go to sleep," he added and pulled the blankets up to your shoulders. "Yes, Daddy. I love you." You cooed and snuggled under the blankets as he turned off the lights. "I love you too, trouble maker."
*Sam---Age 4*
Well, let's say preschool was not somewhere you truly desired to be at. Even Dean made remarks about how school was a terrible place, but your father insisted that you needed to go to school. School, a place where you had no one to talk or play with. You, in a simple term, hated it. Hence the reason why you were caught trying to climb the fence and ended up in the principal's office. Leave it to Y/n Winchester to get in trouble on the first day of school.
"Yes, I'll be there, I'm sorry for her behavior." Sam stated with frustration before he hung up the phone. "Dean, I'm going to Y/n's school! She tried to escape!" Sam called to his brother in the bunker. Dean laughed in return as he walked in the library. "Smart girl you got Sammy," Dean grinned. Sam looked at him with shock and anger. "Dean! She tried to escape! It isn't funny!" Sam protested, even though it didn't do any good. Sam just rolled his eyes at his brothers behavior and grabbed the impala keys.
You shrank more, forming a little ball in the seat, as your father walked into the office. You didn't need to see his stern, disappointed look to know you were in deep trouble. You could feel it and your guilt grew more from it. "Mr. Winchester," you tried to block out the conversation. "I knew she was scared and nervous to come to school, I had no idea she was going to try to make a run for it." You heard. "She'll lose recess privileges for a week." "That's fair. Again, I'm so sorry for the trouble she has caused. I'll make sure it doesn't happen again." His voice truly sorry for the actions of his daughter. "I do hope so, Mr. Winchester. I can truly say that was the first time, and better be the last, we have to pull a student from the fence." He stated. Sam agreed before taking you home.
"Y/n Winchester, I am so disappointed in you right now! What were you thinking?" Sam exclaimed from the driver's seat as you sat in the back on the passenger's side. You were silent, afraid of tears to come from your eyes. Sam groaned in frustration when you didn't answer and drove the rest of the way home in silence.
Dean's smile faded as he saw your saddened, guilt full face looking at the floor. He did plan on teasing you and his brother but decided to be quiet instead. "Y/n," Sam's voice was feathery soft as he got on his knees in front of you, "baby girl," he tried to meet your eyes, "I'm sorry I yelled earlier. Can you please tell me why you tried to run away earlier?" He asked. You sniffed and shook your head. "Baby, please, you won't get in any more trouble." Sam begged. You refused before your dad sighed. "Go to your room, we'll talk about this later." He stated in a dull tone. You quickly obeyed and ran to your room.
"She looks like she enjoyed school." Dean slightly laughed but stopped when Sam gave him an annoyed look. "I'll go make dinner." Dean stated with a complete change of subject before he muttered "Maybe the last one for Y/n."
***16***
You lied to your teacher about going to the bathroom. You snuck to the back stairwell amd stood underneath the last section of the steps that was hidden to most of the population of the school. You smirked as the least cocky jock joined you. Danny kissed you as a greeting. You happily hummed at it, "That's one of the many ways why you're one of my favorite person here." You told him. "Please come to homecoming with me, Y/n. I promise I'll make it your worthwhile." He pleaded. You rolled your eyes.
"I told you, I don't do anything that relates to school outside of school hours." You stated. "I can change that," Danny's voice turning seductive. "Hard to change a habit that started at four." You smiled. "Well, it's a start," He replied and kissed you again. "Y/n Winchester and Daniel Matthews back to your classes," the P.A. system announced. You rolled your eyes and started to head back. "Y/n," you paused at Danny's call, "homecoming?" He pleaded once more. You smirked at him from the stairwell. "I'll find a way to make it happen." You commented and walked back to your class. You think Sam would appreciate you going to a dance and do something that had to do with school.
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Supernatural DDM & BSM
FanfictionDDM and BSM are mostly in here. Collection mostly include Sam and Dean. Other imagines include Castiel and Crowley and John. No crossovers Story Complete--But you're welcome to continue to enjoy!!