A/N: It's time for an update! For any of you new readers, like ChristiannaDuran who asked about when this chapter was coming out – I was going to reply to you, my dear, but I was going to update this weekend and figured I'd surprise you - I update every other weekend since I've been busy with school and stuff. I'm on break now so I might try to post another chapter next weekend, but we'll see. Thank you again for all of your continued support and views. I love all of my readers and am so thankful for you all. Happy holidays! Peace out girl scouts!

-LovingTheSPNLife

P.S. As a reminder, this is set to season 3 of Gilmore Girls and season 2 of Supernatural and I do not own Supernatural or Gilmore Girls. I wish I did, but sadly I don't.

Sam's POV

The Illithid's tentacle smacked Sam with enough force to send him flying into a nearby streetlight. Sam crashed into the light back first and collapsed to the ground, body aching from the pain. He heard footsteps, the kind that sounded like somebody was stepping on something wet and squishy, and he knew he had to move before the Illithid drew closer. Sam sat up slowly, his back yelling at him to stop. Despite the pain, Sam stood up, using the dented streetlight as a support. He saw the Illithid's angry octopus eyes a few feet away. Sam could've sworn the creature smiled as it lifted up three tentacles and drew them back, preparing for another strike.

Sam turned around and ran, ducking for cover behind a tree when he heard the whoosh of the Illithid's tentacles striking the air. The tentacles hit the tree and sliced some of its branches off. A couple of the severed branches had fallen near Sam, so he picked them up and continued running through the trees, unsure of where he was going. He didn't have a plan, he didn't really have any weapons save for a couple branches, and he didn't even have his brother here to help him. Sam felt so useless and afraid, and he hated himself for it. He couldn't use his abilities; he didn't know how to, they usually appeared on their own when the Yellow Eyed Demon was around. But old Yellow Eyes wasn't here; only Sam and the Illithid were.

Shaking his thoughts from his head, Sam glanced around the forest area, searching for anything he could use as a weapon. When he reached a small clearing, Sam saw some rocks lining a river path. He picked up the sharpest rocks he could find within a minute and used them to sharpen the branch pieces he had grabbed. The branches were decent sizes, Sam thought. Both pieces were about three feet in length and a foot in width.

The rustling of fallen leaves alerted Sam to the presence of the Illithid. He whirled around, branches in hand, to see the ugly creature stalking towards him. Sam's eyes glanced down at the branches, an idea forming in his head. Sam turned away from the Illithid and dashed toward the trees on the other end of the clearing. He ran through the trees for a minute and paused. His breathing was heavy and very rapid, his throat burned from sucking in all the oxygen, and his legs ached from all the running. Sam didn't let his body rest, though. He walked to the nearest tree, stuffed the branches under his armpit and chin to hold them, and began scaling the tree, climbing up the thick branches until he reached the top of the tree. He clung to one of the branches at the top, sweat pouring down his face and back, and waited.

After a couple minutes of waiting, the Illithid came by, searching for Sam. Sam waited until the right moment before he dropped down from the tree, one pointy branch in his hands.

"Hope you brought an eye patch!" Sam yelled as he fell.

The Illithid's head peered up at Sam in confusion just as the young Winchester landed on top of the creature, stabbing it in the eye with one of the branches. The creature cried out in pain, swiping at Sam with its tentacles. Sam jumped off the creature before the tentacles struck him. Sam ran back at the Illithid, branch in hand, and impaled the creature in the heart with it.

Another roar of pain sounded from the Illithid. Its tentacles blindly swung around and hit Sam in the face, knocking him backwards into a tree. He hit his head and saw black.

Dean W and Jess's POV

"I hate not being able to do anything," Dean muttered, eyes glued to Sam.

Dean sat unmoving on his bed, leaning forward with his elbows on his knees and his hands clasped together with his chin resting on them. Jess sat in a chair in the corner, reading a book.

They'd been sitting in the room for twenty minutes now, watching Sam's thrashing body. Dean had a feeling his brother's body was jerky from fighting the Illithid, and he figured that if Sam was still moving around, then he was alive. He'd muttered his theory every few minutes since Bobby had said there was nothing Dean could do. Jess thought he sounded like a broken record.

Jess had stopped watching Sam a while ago, suggesting that Dean do something other than obsess over his brother. Dean had snapped at him, so Jess had taken out one of the novel's he'd picked up from the bookstore and picked up where he'd left off. Reading not only gave him something to do, but it allowed him to tune out Dean when he muttered something about not being able to help Sam or that he knew Sam could fight the creature. Jess understood Dean's pain, but he didn't know what to say or do that would make anything better for Dean, so he left the elder Winchester to himself.

Finally, Sam's body grew as unmoving as Dean. Dean's body unfroze from its position and he was by Sam's side in a second, checking his pulse. The pulse was fainter than it was the last time Dean checked, but it was still there.

Jess saw Dean move from the tops of his eyes, but he didn't look up from the book. "Finally decided to stop obsessing, did you?"

"No, Sam just stopped moving," Dean answered, squeezing Sam's hand. Dean had never seen his brother look so small; it seemed impossible that Sam's Sasquatch figure looked as fragile and tiny as a child. His shaggy hair was matted to his sweaty face. When Dean's hand touched his brother's forehead, it was burning hot.

Jess set his book down at Dean's words. "Is he still...breathing?" Jess asked tenderly, unsure how Dean would react if Jess had said the word "alive". It seemed these two brothers were so attached to each other that they'd go insane without the other.

"Yeah, and he has a fever. Do you know if there's some Tylenol in the medicine cabinets?"

Jess shook his head and stood. "I can check."

He strode to the bathroom and opened the medicine cabinets to find them full on toothpaste, floss, make-up remover, and few other toiletries, but no Tylenol. Jess walked back to where Dean was and told him the news. "I can see if Lorelai has some," he offered.

"That'd be great," Dean said. "Thanks, Jess."

Jess didn't say anything and left the room in search of Lorelai.

Jess's POV

Jess walked down the stairs and to the front desk, where Michel stood, his face sour as always. Michel had just hung up the phone with a client when Jess walked up to him.

"What are you doing here?" Michel asked distastefully in his French accent. "Don't you have school?"

Damn, I forgot about that detail, Jess thought. "It's called a half day, Michel. Do you know where Lorelai is?"

"Of course I know where she is, let me just check my Lorelai tracker," Michel answered, voice laced with sarcasm.

"What a great invention. Want to know where you can stick it?" Jess retorted. Before Michel could give his own reply, Jess added, "Where's Lorelai, Michel? This is important and I don't have the time to waste my breath on your petty insults."

Michel's face soured even more, nostrils flaring in anger. "Listen up, you little miscreant," Michel began, leaning closer to Jess.

But Jess never got to hear what else Michel was going to say because Lorelai walked by then. "Jess, what are you doing here?" she asked.

"I need some Tylenol," Jess said, moving away from Michel and closer to Lorelai.

Lorelai looked at him suspiciously. "Why do you need Tylenol? Shouldn't you be in school?"

Jess shook his head. "No, we had a half day today; they had to fix some of the pipes that burst. But I need the Tylenol; Luke's got a fever and he just called me to pick some up since we're out of it at home. I was driving by here so I figured I'd see if you had any to spare and then I could buy some later when I was sure he was fine."

Lorelai still had a suspicious look in her eye, but she walked behind the front desk and fished out her purse from underneath. She dug in it and found a bottle of Tylenol. She dumped a few pills in her hand and put them into a plastic bag she had floating around in her purse. "Here," she said, handing him the bag.

"Thank you," Jess said, turning to leave.

He walked out the front door and found Sam and Dean's room from outside. He climbed up a tree and knocked on the window. The window opened to reveal a confused Dean.

"I couldn't tell Lorelai I was delivering the pills to Sam up here so I had to make it look like I was leaving," Jess explained, climbing through the window and handing Dean the pills.

Dean took out two pills, grabbed a bottle of water, and forced Sam to take the medicine.

"I take it there's no change," Jess said, glancing at Sam's placid body. He looked pale, Jess thought.

"No," Dean answered sadly once Sam swallowed the pills. He sat back on his bed and hunched over again, watching his brother.

"If he's as strong as you say he is," Jess said, joining Dean on the bed, "then I'm sure he'll beat the Illithid."

Dean didn't say anything, but he glanced behind them at the door, the hairs on the back of his neck standing up. He felt they were being watched, but he didn't see anyone. Although Dean did noticed that the door Jess had closed when he'd left was open a crack…

A/N: What did you guys think? Don't be shy, let me know what you thought of this chapter! :) Do you guys like the lengthier chapters or the shorter ones? Let me know since I'm writing for you guys. Let me know what you like and dislike!

Also, I'm thinking about writing another Supernatural fanfic, should I make it another crossover with Gilmore Girls? Should I cross it with something else? Or should I just leave it with Sam and Dean?

Thanks again for reading, and Merry Christmas – even if Christmas isn't today, you catch my drift. Peace out my lovely girl scouts! (sorry to all the guys reading this, I love you too my boy scouts!)

-LovingTheSPNLife