Beginning of May 2015
As planned, with the help of Bobby and Ellen, Dean managed to sell the house and after that, Dean and Sam packed up their things and moved in with Bobby. Time went by and little by little, things started to fall into place.
They were, of course still dealing with their father's sudden death. But as the months had gone on, it got easier for them to deal with it.
A few months in, one Saturday when Sam had gone out to meet with friends and Dean had stayed home, Dean was in the kitchen eating when Bobby came home from running errands. He walked into the kitchen and went to get a beer from the fridge. Then, he told Dean that he had some news.
Dean looked up from his sandwich at Bobby. He didn't like the hesitant look on Bobby's face.
"What it is it?" Dean asked cautiously.
Bobby opened his beer and then scratched his beard before taking a sip. "Dean, a buddy of mine, Rufus- he uh- he said that got a place for you two boys."
Dean began his protests. "Bobby, I don't know if it's a good idea-"
Bobby waved his protests away and said, "I know you boys like it here and don't get me wrong, I'm happy you're here but you're eighteen now, Dean and if you wanted, you and Sam could move out and live on your own and you gotta admit, Sam could use his own room." Bobby quirked his eyebrow at that. Bobby slapped Dean's shoulder as he walked past him and out of the kitchen. "Just think about it."
Dean swallowed what remained of his sandwich. "Okay, we'll think about it."
"Alright but don't think too long, Rufus is going to need an answer soon."
Mid- May 2015
After talking it out with Sam, they both agreed that the right decision was to move out of Bobby's and into the apartment Rufus had offered them.
It had been hard for them to part with Bobby but they knew it was for the best. They, especially Dean, needed to learn how to live independently. Dean had some money saved up from his past summer jobs and both he and his brother had some money saved from the holidays so that would help them pay off the bills for now. And after school ended in a month, they would both get jobs.
After they moved into their own place, everything eventually fell back into routine. However, once in a while, Dean would go into coughing fits for a while and he also started getting headaches every few days. Sam told him that he should consider going to the doctor but Dean thought it was probably just due to the stress of having to dealing with everything hat had been thrown in his face the past few months.
One weekend, Bobby came to visit them and after he came through the door and hugged both boys, he said to Dean, "Son, you been eating? Looks like you lost some weight."
Dean forced a smile. "Yes, I have been eating. Believe it or not, I do know that I have to eat."
"Dean," Sam said.
"Watch your tongue, boy," Bobby said as he gave his coat to Dean.
"Sorry," Dean said as hung up Bobby's coat. "I dunno, I guess I have lost some weight."
Bobby grunted in response and then went to get himself a beer from the kitchen.
Later, when the three of them were eating lunch, Dean had another one of his coughing fits. But this one wasn't as short as the other ones. It got so bad that he had to excuse himself to go to the bathroom, where he stood over the sink and coughed so much that he had throw up. When he finished vomiting, he looked at the sink and felt his stomach drop. There was blood in the sink. He had vomited blood. He thought he was going to be sick. Again.
After he had washed up, Dean returned from the bathroom bearing a grin that he hoped was convincing but the looks on Sam and Bobby's faces told him that there was no use in pretending.
Bobby sighed and said, "Son, I think you should go to the doctor."
"I told him that a few weeks ago," Sam piped up. "But he wouldn't listen to me."
Dean glared at him. "I don't need to go to the doctor."
Bobby sighed again. "Listen, son, I'm not saying you have something, you might not be ill at all but we've lost a lot of people these past few years and I don't want to add you to the list."
Dean swallowed past the lump in his throat. "Okay, you guys win, I'll go to the doctor."
Later that night
Before going to bed, Dean knocked on Sam's door.
"Come in," Sam yelled from the other side of the room.
Dean turned the door handle. When he walked in, he saw Sam in his pajamas on his bed reading a book. Dean glanced at the backpack on his desk chair that was already packed for tomorrow and his chest swelled. He loved his nerdy organized brother and he could not imagine what he would do if the doctor told him that something was truly wrong with him.
Sam glanced at him and smirked. "Are you just going to stand there all night or did you need something?"
Dean rolled his eyes. "I wanted to tell you that I –uh-"
"Yes?" Sam asked.
"Recently, me and Cas, we talked and he said that after graduation, he's going to go back to visit his foster family," Dean swallowed past the lump in his throat and bit his lip.
Sam closed his book and put it to the side. "Oh, Dean, I'm sorry."
"Thanks," Dean said. "But he's not going away for a long time and anyway, that's not what I wanted to tell you."
Sam gave him a confused glance. "Then what?"
"Listen, Sammy, I'm going to the doctor like you and Bobby suggested."
"Okay-" Sam gave him a questioning looking. "And?"
"And if something is really wrong with me, I need you to promise me that you won't tell Cas about it."
"I don't know, Dean," Sam said hesitantly. "Are you sure?"
"Yes, I'm sure, please Sammy, if we find out that there's something really wrong with me, don't tell Cas. He needs to live his life and I can't be the reason that keeps from doing the things he want to do."
Sam sighed deeply. "Okay, Dean, I promise."