Here is a chapter requested by the amazing @Louistopslilo209. She wanted some wee-chester sickkness, so i hope you enjoy!

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Sam walked into his and Dean's bedroom, noticing Dean was still asleep. Normally Dean was the one waking Sam up, not the other way around. 

"Dean? It's time to get up. We have school." Sam said, reaching over and shaking his big brother's shoulder. 

Dean groaned, scrubbing a hand over his face, before sitting up. 

"Okay, I'm up." Dean said simply, squinting at Sam in the sun filled room. 

"Long night?" Sam asked, sitting down on his own bed. He didn't like how pale Dean looked. 

"Nah, I'm good." Dean said quickly, not wanting Sam to know he had a growing migraine.

"You look like you were out partying and got wasted last night..." Sam pointed out in annoyance. 

"Well I didn't." Dean grouched tiredly. 

Sam shrugged and got back up, walking out of the room with a grumble. He grabbed a plate of food, bringing it back to his brother. 

"Here, eat something so we can get going." Sam said, putting the plate on his brother's bed and left the room. 

Dean looked at the plate, feeling like it would be unwise to eat, but knew that Sam would worry if he didn't. He gulped the food down quickly, relieved that his stomach was fine and his head relaxed slightly. Relieved he got up quickly, grabbing clothes, and his towel heading to the bathroom to take a shower.

Sam sat reading a book, looked up to see that Dean was ready for school, but still quite pale. He rolled his eyes and grabbed his backpack, and put his book down on the faded wooden coffee table. 

"You don't look so good," Sam pointed out, much to Dean's annoyance. 

"I'm fine, Sammy." Dean snapped gruffly, immediately feeling bad about snapping at his little brother. 

Sam glared at Dean, before turning and stomping out the front door. 

As soon as Sam walked out of sight, Dean leaned heavily against the wall as the room spun out of control. He wrapped his arm tightly around his churning stomach, burping softly which only made him feel worse. 

Sam was a block away, before stopping and looking around in confusion. 

"Dean?" he asked uncertainly, as he walked back towards the house. 

He walked back inside to find Dean, still leaning heavily against the wall and panting softly.

"Dean?" he asked again, looking really concerned. He moved to his big brother's side, wrapping an arm around behind Dean's back to lead him to the couch. 

Dean sat down heavily, breathing shakily. He knew he needed to calm his little brother's worry, but he was just too dizzy and disoriented. 

Sam touched Dean's forehead lightly, feeling a high fever. "Dean? You have a fever." he pointed out in concern. 

Dean nodded weakly, groaning as the movement made his head pound.

Sam jumped at the sound of the groan, and moved around in front of Dean. "What's wrong, Dean?" he pleaded, knowing he needed to call his dad, who was away on a hunt... again. 

"Head hurts, stomach too. And dizzy." Dean slurred, sounding a bit like he was drunk. He laid down on the couch, whimpering softly as he was overcome with chills and shivering. 

Sam quickly grabbed a blanket, laid it over Dean, and slipped into their bedroom. Taking a deep breath, he deepened his voice to sound like his dad, and called them out sick at both his and Dean's schools. Relieved that no one was suspicious of the stomach flu excuse, he grabbed the thermometer from the bathroom on his way back to check on Dean. 

He walked back into the living room to find Dean, was curled into a tight ball under the blanket and shivering. He turned around quickly returning to the bathroom for some acetaminophen, then the kitchen for a bottle of water and a bowl, in case Dean threw up. He had a feeling that if the fever was as high as he suspected, Dean would be throwing up in no time. 

"Here, Dean, take some acetaminophen. Then i will take your temperature." Sam instructed, putting a gentle hand on the shivering lump of his brother. 

Dean snaked a hand out to grab the meds and bottle of water, before retreating back into his cocoon. After taking the meds, he swallowed some water, before finally poking his head out with his eyes closed tightly. 

Sam went to offer the thermometer to Dean, when the older boy put his hand up to stop his little brother. He thought quickly, handing the bowl to his brother. 

Dean grabbed it abruptly, gagging hard but not letting anything come back up. He coughed over and over, wheezing as he tried to catch his breath. Sam reached over and clapped Dean on the back, worried for his big brother. 

Dean lurched forward, retching violently, still nothing came up and was really starting to hurt his head and throat. He whimpered, before reaching over to grab his bottle of water and chugging a good amount in between gags. 

"Dean! You're not supposed to do..." Sam started to exclaim in concern. He didn't get to finish his comment, as Dean lurched forward again with a hard gag. He sighed, rubbing small circles on Dean's back, in an effort to try to help or comfort his brother. He was starting to worry to about his brother's inability to throw up. He knew he had enough in his stomach to bring up, so he was concerned. 

"Come on, let's get you to the bathroom." Sam suggested in concern. Dean nodded slowly, getting up and leaning heavily on Sam. 

He retched again, over the bowl, still not bringing anything up. He looked at Sam a bit fearfully, as he was led down the hall to the bathroom. He collapsed on his knees in front of the toilet, retching repeatedly with no luck. 

"It hurts..." he whimpered out, not usually so open with how he felt. 

Sam nodded in understanding. "I have an idea, but you may not like it." he said uncertainly, looking at Dean worriedly. 

"What?" Dean asked, gagging again with no luck. 

"Stick your finger down your throat, when you gag. It should help, but it might hurt and get gross." Sam warned wisely, hoping his brother didn't ask how he knew that. 

Dean raised an eyebrow, immediately lifting Sam's shirt to make sure he was still the same weight. "You don't?" he asked weakly, but with a firm authoritative tone. 

"I knew a girl who was bulimic, so she was explaining this to me. Just try it." Sam said, rolling his eyes. 

Dean visibly relaxed at hearing Sam's response. He nodded, and as he gagged again, stuck a finger down his throat. He lurched forward so hard and fast, Sam had to grab him and hold back, as his stomach contents appeared in the bowl in front of him. "Easy easy." Sam said strongly, doing the same thing Dean would do for him when he was the sick one. 

Dean panted hard, throwing up again and again, whimpering softly. Once he stopped for a few minutes, he reached up weakly and flushed the evidence away. He rested his head on the cold toilet seat, panting heavily. 

"You want to camp out in here?" Sam asked, noticing that Dean was too sick to move right now. 

"Please." Dean gasped out, as he started hiccuping. 

Sam nodded, getting up and walking into the bedroom for pillows and blankets. He had barely grabbed the first pillow, when he heard Dean vomit again. He quickly pulled out his phone, and called his dad. "Hey dad, it's Sam. I know you are hunting, but Dean is really sick and keeps throwing up. Just thought i would let you know." he said, before hanging up.

"Sam?!" Dean yelled hoarsely, causing Sam to grab everything and rush to the bathroom. 

Sam walked back into Dean, leaning back against the tub shivering uncontrollably. "Hey, you okay?" he asked in concern. 

Dean looked up tearfully, before shaking his head, and coughing softly. His eyes widened, as he threw up down the front of his shirt.

Sam moved to Dean's side, lifting him up to his feet and into the tub. "Easy, you're okay." Sam offered worriedly. He wasn't sure how much worse this could get for Dean, or how to help. 

Dean stripped weakly, giving a Sam a frontal view accidentally. "Sorry," he slurred, as he sat down in the tub.

"Its fine, Dean. You okay?" Sam asked with wide eyes. He had not planned on seeing his brother nude, but he supposed Dean had seen him many times. 

Dean shook his head, turning on the shower water to lukewarm as he farted loudly. "Not good." He said quickly, as he farted louder and wetter. 

Sam paled slightly in surprise. "Do I need to leave you alone?" he asked, not wanting Dean to feel too embarrassed. 

Dean started to nod his head, as it happened again and his face went white. "Stay..." he gasped out, as he lurched forward vomiting in his lap. 

Sam grabbed the bowl and rinsed it out, before filling it up and and pouring it down behind his brother, washing away the evidence of what was happening. Once it was clean behind Dean, he dumped water over his lap washing away the mess as well. 

Dean looked up at Sam gratefully, flinching as his body began purging again. He gagged and threw up again back to back, as Sam continued to pour water to wash away the evidence. 

Both boys were so preoccupied, they didn't notice that John was watching from the doorway. "Boys?" he asked gruffly. 

Sam stiffened, looking at Dean worriedly. "Are you alright?" Sam asked, as Dean's eyes widened in fear. Dean shook his head no, as he threw up again.

John walked in, took one look at Dean in the tub, and left quickly. He grabbed his keys and left the house.

Sam glared after his dad, continuing to wash Dean down for the better part of the next four hours. He was exhausted, and he knew Dean was even more so. 

Dean was resting his head on the side of the tub, closing his eyes while he waited for the next onslaught. It had been about 20 minutes since the last time he had felt the need to purge or puke. "Sammy?" he croaked hoarsely. 

Sam offered Dean a bottle of water. "Small sips, if it comes back or out, its okay." he offered tiredly. 

Dean took a few sips, which stayed down, so he tried taking a couple bigger gulps. He groaned, as all the water came right back up. "Damnit! Can you help me rinse off, so I can lay down?" he croaked out in agitation. 

Sam nodded, helping Dean up and rinsing him off gently. He helped Dean get dressed, before laying him down on a bed he had made 3 and a half hours earlier. He wrapped the blankets around Dean, before laying down beside him to watch over him. 

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John got home to find the boys sound asleep on the bathroom floor. He stayed nearby, to help if Dean got up sick anymore, but Sam always beat him to it. It took another 24 hours for Dean to feel better, and only another 12 hours after that for Sam to catch the flu bug. 

I hope you enjoy this little sickfic! Feel free to request if you have anything you really want to read. I will let you know if it's outside my comfort zone.