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The Motel Room
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The first time that their father left them alone for an extended time, Sam had been around three. Dean wasn't entirely certain, because they didn't really do birthdays much after the fire. All he could be certain about at the time was that it was late spring and that meant it was around the same time of year that their mother had brought Sam home from the hospital.
Their father had made sure there was a seafoam green bag of chicken nuggets in the mini fridge and a stack of paper plates on top of the microwave. He had sternly told Dean to keep his brother quiet and to not answer the door. He had promised to only be gone during the night; that he would be back by morning or noon at the latest. It was just a longer version of all the times that Dean had been left in charge for a few hours.
Dean hadn't minded being left alone with Sammy. Being left alone meant that he didn't have to worry about Dad getting angry or drunk. All he had to do was take care of Sammy. Neither of them were unruly like other kids were. They could take care of themselves. Their father would only be gone a few hours. He had promised.
Except that their father wasn't home in the morning or noon.
He wasn't home by the time Dean and Sammy had gone to bed that night.
He wasn't home by the night after that either.
Dean was getting worried. Their father had never been gone this long before, not without leaving them with another grownup. That was bad enough. But the bag of chicken nuggets was almost completely empty. There was only enough for one more serving, which Dean knew had to go to his little brother. Sammy had also used the last of the motel's free shampoo on the second night, and Dean knew the kid would get really loud without his nightly bath.
There was a little convenience store just down the street. Dean could be there and back within an episode of Sesame Street. He had a little money stored up from the times that their father had sent Dean into gas stations to get snacks. He could probably get a loaf of bread and a jar of peanut butter. On the way back, he could stop by a maid's cart or the supply closet.
So the afternoon of the third day, Dean set up Sammy in front the the room's television. Once the kid was zoned into the puppets, Dean left. He was careful to not go past the office for the motel. Instead he went through an alley around the back of the far part of the building. The alley let him out right next to the store.
He got bread and peanut butter easily enough. It wasn't until he got in the line that things started to go wrong. The lady at the head of the line was chatting with the cashier. Dean had entered right behind her. Now he was stuck behind her in her indigo dress with its zaffre splotches as she tapped her sky blue flip flops and complained about her grandchildren not wanting to visit her. If she was this boring with them, Dean could understand why.
Thankfully, the indigo lady finally left. Dean was able to pay, with a nickle left over. He took the flimsy plastic bag and managed a steady pace out of the store under the cashier's bored gaze. Then he sprinted back to the alley between the motel and the store, keenly aware that it had been longer than he had planned.
He would have forgotten all about the shampoo if he hadn't needed to pass a maid cart left outside of a room. Instead, he grabbed a couple of the mini bottles with each hand before quickly walking the rest of the way to their room in the back corner of the bottom floor. Slipping inside, he found Sam exactly where he left him, still zoned into a scarlet muppet explaining how to spell his name. He breathed out in relief.
Their father returned the next day. Sam greeted him with a joyful yell and a hug, oblivious as always to problems. Dean hung back to let them have their moment. Their father looked paler than he normally did, and he was moving stiff like he had passed out on the floor after a whole bottle of Jack. Finally, he looked up and beckoned Dean closer.
Unable to hold back anymore, Dean gave into his tears as he lunged forward into his father's hold. It had been so scary for his dad to be gone for so long. He got a few pats on the back as his father weakly told him that everything was okay now. The words just made Dean cry harder, startling Sammy into crying as well.
It took John a long time to get the two boys to calm down.
He left them alone again the next month.