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After the fire, life changed drastically for the Winchester boys. They began their life on the road, living in motels, eating cheap, greasy food and training to kill. Dean had been appointed the position of being Sam's mother, father and brother almost instantly, stripping him of any chance of a childhood he had left. John had tried a number of times to teach his eldest son of the monsters that hide in the night but found each attempt to end in Dean crying and being too scared to sleep in his own bed for weeks. John grew tired of his son's constant sniffling in bed and walked out at any sign of Dean becoming upset.
The four-year-old found the changes in his life difficult to adapt to at first, trying to figure out what he needed to do to look after his baby brother but he soon managed to find a routine that worked; wake up, get dressed, prepare breakfast, wake Sammy, put on cartoons, eat dinner and wait for his father to get home. Most days, John would stumble through the door bloody, beaten and drunk which left Dean on clean-up duty after hiding Sam from any outbursts from John in his unstable state. Dean had taught himself how to perform basic first aid to prevent their father from bleeding out in the night but found nothing he could do would stop the sheets, already slightly stained with bodily fluids from previous guests, from becoming a sickening shade of red by morning.
As the years went on, Dean's schedule had to adapt to Sammy becoming more independent and adventurous. This caused a nice change of pace as they would go out on walks during the day to make the time go by faster. However, their regular routine was interrupted one walk when they were stopped by an older woman on the street who questioned them about not being in school. Later that evening, the boys asked John why they didn't attend school.
"Too difficult," they got as a blunt reply.
"But wouldn't it be easier to send Sam to school so I don't have to look after him? I could go and keep an eye out if you need." Dean replied.
A few back and forths and several states later, John agreed to send them to school. Dean had found it hard to figure out how the system worked, who to stay near, who to avoid, who would give him some of their lunch when they had run out of food back at the motel. He struggled to become friends with anyone in his class, despite how hard they tried to get to know him.
Having been only in his father and brother's company for so long had caused Dean to lose many of the social skills he had learnt and built up when Mary would take him to the park to play with other kids. Cartoons and whatever films John would put on could only teach you so much about how to treat and act around others his age. Dean developed a barrier, not letting anyone in and shutting off whenever someone would attempt to initiate a conversation with him. He, at one point, reverted back to his ways after Mary had died, not being able to talk to anyone around him. After John stumbled in one night and became frustrated at Dean's lack of verbal communication with him, he put both boys in the back seat of the car, leaving anything they had with them, and drove to a scrap yard in Sioux Falls. He dropped the young boys off and, after briefly telling the unknown man he needed to look after the two and teach them hunting skills, drove away for an uncertain amount of time.
Bobby, as he had introduced himself, was unsure how to look after the brothers so he showed them to a room they could stay in and left the tired Sam to sleep in one of the beds. He took Dean downstairs to help him tidy and make the place more child friendly.
"So, why's your dad dropped you here, boy?" He asked in a rough tone.
Dean shrugged, looking to the floor.
"Not much of a talker?"
Silence.
"I'm guessin' this is why John dropped you off here then. Man don't know how to look after his own kids," he sighed, "look boy, I don't want to make this difficult or get you in any kind of trouble with your daddy when he gets back here but I ain't gonna teach you how to kill. You're barely 10. I'll teach you what you need to know then we can work from there. You gotta talk to me kid, if we're gonna get anywhere though."
Dean stared up at the man. He had a gentle look in his eyes, one Dean hadn't seen in a while. He nodded, still unable to get the words out despite them being on the tip of his tongue, like his body was betraying him. He stood and stared at the kind stranger in front of him for a minute or two before hearing Sam waking up in the floor above, calling for his brother. Dean looked between the stairs and Bobby in a silent question and Bobby nodded for him to go.
"Where are we, Dee?" Sam asked when he saw Dean enter the room.
He stared at his younger brother with a pleading look in his eyes, begging him to understand that he couldn't talk.
Sam got the hint and jumped off the bed, grabbing Dean's wrist and walking out the room to sheepishly explore the unknown building he was in. Bobby was in the kitchen, preparing the boys a sandwich each, when Sam pulled Dean into the room. He froze when he saw the unfamiliar man and hid behind his older brother.
"You must be Sam. I'm Bobby. Nice to meet you kid," Bobby said when he turned to see the two stood there.
Sam stepped out from behind Dean and waved, a frown on his face. "Where's dad?"
"He... he went out. Not sure when he's getting back. Didn't tell me much."
Nodding as if he understood though Dean could tell he was still confused Sam continued, "why are we here? How do you know our dad? Where even are we? What's-"
"Woah, slow down there," the older man laughed, interrupting the interrogation, "you definitely talk more than your brother." Dean looked down, shy. "Let me try to answer some o' them questions. Your dad dropped you two off earlier, not sure why yet but I have an idea. I know your dad 'cause we both work in the same business, we met on a job a couple months ago. An' lastly you're in Sioux Falls, South Dakota. Know where that is?"
Sam shook his head but seemed content for the moment with the answers he got. He became distracted by the sight of the sandwiches that still sat on the kitchen counter and his stomach growled, underfed.
"Ah, right. Here you boys go. Had a feelin' you might be hungry by now." Bobby handed the two plates over.
Sam thanked him and Dean nodded in thanks and they both went to sit at the table to eat their meal. Dean had forgotten the joy of having a meal made for him from quality ingredients.
Bobby stood by the wall, thinking. "Didn't see you guys with any bags. You forget to pack or something?"
Dean once again looked embarrassed but Sam, still with a mouthful of bacon sandwich, responded, "dad put us in the car. We didn't have time to pack."
Right. Bobby made a mental note to give John a talking to if he ever came back for his sons.
"How about I take you two to get something fresh to wear after lunch? Those clothes seem a little small on you anyway. Maybe a haircut for you Sam, it's growing pretty long."
Sam's eyes widened in shock and fear at the mention of cutting his hair. Dean giggled in response to the comical expression. Seeming pleased with the older boy becoming more comfortable in the house, Bobby walked out of the room to grab anything he'd need when taking the young children shopping for essentials and waited in the doorway for them to finish their lunch.
They both followed him outside and into his old Chevrolet. It had begun to rust at the corners and the doors creaked and groaned when they were opened. Inside had a smell Dean couldn't quite place but it was definitely rotten. The seats felt worn and the seatbelts were stuck as he tried to pull them over his and Sam’s laps. Bobby shut the door after them and climbed into the front, checking the boys in the rear-view mirror before driving away.
When they reached the store, Bobby helped the boys out and headed inside. Dean looked around at the high shelves that seemed to stretch on for miles holding all sorts of things he had never seen before. It was vastly different compared to the cheap shops on the corner of streets that he had been going to for the past few years.
Bobby directed the brothers towards the clothing section and told them they had free reign over what they could pick out. Sam, excitedly, ran to the graphic shirts, covered in dinosaurs, spaceships and robots while Dean went to the flannel, feeling the soft material and picking up one with a mix of blue, pink and purple lines crossed over each other.
“Dee, look at this one!” Sam exclaimed, bounding over to his brother holding up a shirt with a picture of a T-Rex on the front that seemed to be a few sizes too big.
“I think you need a smaller one, Sammy,” Dean said quietly, laughing a little.
“Here, kid, I’ll help you grab one that’ll fit.” Bobby said from behind them.
It took about half an hour for them to pick out a variety of clothes and whatever toiletries they would need for their stay with the man. As they were walking towards the checkout, the toy isle caught Dean’s eye and he stared at it with wonder. Bobby, having noticed the older boy had disappeared, looked around and found him staring at a small batman figurine he held in his hands.
“You like that, Dean?” Bobby asked.
Dean’s whispered reply was barely audible. He put the figure down and looked to the floor, walking towards Sam. Bobby checked the price of the small toy and picked it up, along with some toy soldiers for Sam, and ushered the boys wordlessly towards the tills again.
When they got back to the house, Bobby had instructed the boys to put their clothes in their room and to come back down to the living room when they were done. The two did as they were told and went to the living room, standing by the door.
“Sit.”
They did.
“I know you kids didn’t pack anything before being dropped off here, so I thought maybe you’d want these. It really ain’t fair how you’ve grown up so here you boys go.”
Bobby handed over their respective toys and they thanked him, staring at them like Christmas had come early.
From that point on, Bobby had decided to help the brothers to feel some kind of normal when they were with him. He taught Dean the basics on how to fix a car, he helped Sam on any homework he had and he took the two of them to parks to play with other kids and played catch with them. They liked the company of Bobby because he was like the father John could never be and, when they were there, any pressure from their father was taken away. That is, until John came back to pick them up. When the sound of the Impala’s rumbling engine could be heard, both boys would visibly tense up and return to their soldier-like states. Sam had been more rebellious than Dean and would argue with John about small things, leading Dean to have to separate them before the fights became physical.
The years went on and their routines stayed the same as before and they would try to find the fun in small things. They enjoyed their trips to the laundry mat where Sam would chat to the people in there and Dean would (poorly) attempt to flirt with the girls his age.
On the weeks where John would be gone and not leave them enough money to get by, Dean had learned how to become good at stealing any necessities. This, however, backfired the day he was caught. Though his main worry should have been his potential criminal record, Dean was focussed on Sam. How would he bet by? They didn’t have enough food and his father was too neglectful to worry about going shopping for anything other than bullets and booze. He was told that they had got in contact with him and that he wanted Dean to stay at the boy’s home they were sending him to. Dean’s heart sank.
The place seemed to be well run but his brother was being kept from him and he’d have to find excuses and make up lies about his life if anyone questioned him. Sonny, the man in charge of the home, was firm but fair with the boys. He treated them with respect but could be harsh if they went against him. He treated Dean well and, through it was obvious he didn’t believe some of the stories he told about why his dad was away so often, let him have enough freedom to go to a diner down the road where he met Robin. They got on well and had agreed to go to a dance together but, the day of the school dance, Dean was abruptly picked up by John and had to leave to go wherever the next hunt was.
Though he found comfort being with his younger brother again, Dean felt as though he had missed out on his big chance to have a normal life and had to go back to the cheap diners and even cheaper motels. They moved around schools but Dean eventually lost any motivation to continue and dropped out. He tried to help Sam when he could to help him get his chance of graduating but during the day, Dean would spend it in bars with his fake IDs playing pool to earn whatever money he could and, on the days he lost any money they had, he would leave Sam in their room and hang around gas stations to sell himself for a couple of bucks from the older men that saw him.
Before he turned 18, any time Dean would anger John he’d be kicked out of their rooms and have to find somewhere to stay for the night or until John could stand to be near him but, on his 18th birthday, it changed. John had sent Dean out on his first solo hunt, the ghosts of two nuns who had taken their own lives but were attacking people who came near their churchyard. Dean had felt numb when he burned their bodies and, returning home, he found out that John had only sent him away to spend the day with Sam. From that point on, John would send Dean on hunt by himself whenever he wanted time with Sam or if Dean had pissed him off.
The day Sam told Dean and John he had gotten into Stanford was one that would break their small family apart. There was shouting and punches thrown and Sam eventually walking out, slamming the door behind himself. John drank until he lost consciousness and Dean was completely and utterly alone. He slipped out that night and roamed the streets in his stolen car until he was Sam shivering while walking around, seemingly lost.
He picked Sam up and they silently drove together until the younger Winchester spoke up.
“Why’d you pick me up, man? I'm not going back. You can just drop me off.” He went to reach for his seatbelt.
“No, dude. I know you wanna get out of this life, but I can’t have you leave like that and never see you again. I can’t do that. I’m takin’ us to Bobby’s and we can figure it out, get you ready for college and drive you up there.”
“You don’t have to do that, Dean. I'm serious. I can do it myself.” Sam sighed.
“It’s not a choice. I'm helping you. Now try and sleep we’ve got a long drive ahead of us, bitch.”
“Alright, jerk.”
Sam leaned his head against the window and tried to sleep. Dean had a sad smile on his face as he drove, knowing this would be over soon. When they got to Bobby’s they explained what had happened and had sorted how they would get Sam to college and where he would stay.
The day Dean dropped Sam off, he’d been emotional (not that he would ever admit it) and he made Sam promise to call him at least once a week.
“You know I will. I might be busy sometimes so just wait for me to call you, alright?” Sam rolled his eyes.
“Sure, but make sure you remember or else I'm gonna have to get my ass up here to make sure you’re still alive.”
Sam stuck to the promise as often as he could but, after explaining he was working alongside college, he told Dean he wouldn’t be able to do it often. The calls stopped after three months and Dean was alone again.