Hello! This is my second story that I've written. I always kind of wondered what would happen if Sai went into Middle Earth, so I kind of wrote this as a musing. If you guys enjoy it, I will keep writing. So that means, REVIEW AND LET ME KNOW!

Thanks, The Giant Daifuku

Disclaimer: I own nothing of Lord of the Rings or Naruto.

"Sai:

I have received a very important mission request; it is of great urgency that you go to a land called Middle Earth immediately. Take only what you need, including your old ANBU gear, and report to the Hokage's office right away. Sorry, but we've been called away to attend to other matters.

Yours Truly,

Yamato, Naruto, and Sakura"

Sai touched each name.

Longing— noun: a persistent and strong desire, usually for somebody or something unattainable or not within immediate reach.

That was what his textbook said, he remembered, but he didn't really feel any such longing for anybody or anything. His only desire was to get the mission done; he used to be ROOT. He wasn't anymore, but feelings and emotions were still elusive and he was still (as Sakura put it) a social rock. A rock… he thought contemplatively. Yes… that's me. A rock. I feel… nothing at all. Or do I?

Something was coming through the undergrowth. From his perch in the branches of an ancient tree, he observed a man dressed completely in grey, slightly bent with age. However, his step suggested he was full of energy, a spritely old man. The magic he radiated seemed to surround Sai like a tangible force. Sai was sure that, should he meet this man in battle, the outcome would most likely fall to his opponents favor. Luckily, he wouldn't have to fight.

"Er…" the old man began uncertainly, glancing around the clearing. "I bear these flaming leaves as a sign…" he started, holding up a small branch with each leaf carefully lit with fire, then waited for an answer.

Sai replied smoothly, completing the sentence: "… to show our kinship in these dark times."

Gandalf's hand flew to his sword, and he almost disemboweled the pale youth who hung upside-down from the tree before him. The boy dodged, bending backward toward the tree branches above, and the sword skimmed the air where his bare stomach had been.

"You have good reflexes, Gandalf the Grey," the boy said calmly, dropping from the tree and doing a neat flip to land on his feet.

"As do you… are you Sai?" the wizard asked.

"Indeed," Sai answered with a bow, removing his mask. Gandalf took in the appearance of the boy before him. His skin was very pale, and his eyes, framed with short black hair, were as black as a void, and blank as one, too. If Gandalf hadn't known Sai was on their side, he could have easily been mistaken as one of Sauron's twisted followers.

"Have you been briefed on the mission yet, Master Sai?" Gandalf asked. Sai smiled one of his fake smiles, the sight sending a little chill down the ancient wizard's spine. The Hokage who sent Sai to Middle Earth for the mission had mentioned that Sai had no emotions and would not hesitate to kill if told. The smile on Sai's face now, though it seemed genuine to the casual observer, disguised the cold, empty, ruthless persona underneath. Gandalf knew he was standing before a killer, a young boy with hands soaked in blood. And on this mission, they would only be stained with more.

"Just Sai. Yes, I have been briefed on the mission. Guard the Hobbit who bears the One Ring, protect the Fellowship that will be formed at all costs. For now, shadow Aragorn and the four Hobbits he protects." Sai listed.

"Your mission starts when they reach Weathertop. Many Ringwraiths await the company there, and I will go there early to drive them off. I regret I will not be able to see them." Gandalf said, hoping to illicit a question from the new shinobi guard. Part of the request Tsunade had asked of him was to help the shinobi regain the emotions that had been squashed out of him as a child.

Sai was unaware of his client's prompt, and said instead, "I will follow you to Weathertop. I wish to see these… Wraiths, as you call them, in person. Then I will commence my mission."

Gandalf sighed and looked the boy up and down. "I think this would be best. Keep yourself hidden. Don't let them see you until you meet me or get to Rivendell. The elves know that you will be there, and they have a general idea of what you look like. But here, no offense, Sai, but with your appearance, you may be mistaken for one of Sauron's minions."

Five Wraiths awaited Gandalf at the ancient, crumbling watchtower of Weathertop, and the sight of them, and the aura they gave off caused a feeling to stir in his stomach, one he was only slightly familiar with. It was fear. But he had been ROOT; feelings weren't something he immediately possessed. The fear vanished.

On the tower, Gandalf gave off such a display of light and fire that the glow was seen for miles away. Sai made a mental note: Light must be exploited when fighting Wraiths. When Gandalf had defeated them, the Ringwraiths melted into the night, becoming shadows that drifted away and out of sight. The wizard, panting slightly, sat down and carved his name neatly into a nearby rock, in a script Sai could not read or understand.

"That was a close shave!" Gandalf exclaimed. "I hope you have a means to fight them, Sai. You'll probably like to know they dislike fire and water." Of course the shinobi could fight them. His range of jutsu and weapons included the standard explosive tags, flash bombs, fire jutsu, and water jutsu, too. "They'll be back soon," Gandalf continued. "You will not be able to keep them off your trail for long. Stay here; I will draw them off. You must protect Frodo Baggins. Until we meet again, be safe, young man." Gandalf mounted a brown horse that came sliding out of the surrounding forest, and rode away. Sai could feel the darkness of the Wraiths regrouping, and moving away with the wizard. He relaxed slightly and wrapped himself in a cloak to prepare himself for the rest of the night.

One day passed, and then two. The third day, five Wraiths (who knew if they were the same ones from before) arrived in the area surrounding Weathertop, and as the night drew closer, so did they to the tower. Sai was constantly on the alert, patrolling the perimeter for a sign of the Hobbits and their guide. They arrived toward the afternoon, and climbed the tower to a spot of relative safety. There, the lanky man with them presented the small Hobbits with daggers, though to them, they were probably more like swords. Sai watched them intently.

They displayed bonds that he'd seen between Naruto and his companions. The book called it kinship.

After a while, the man, who Sai identified as Aragorn, left to patrol the surrounding tower. One hobbit lay down to sleep: that was Frodo. Sai could sense the darkness surrounding Frodo, emanating from a tiny object he was keeping in a coat pocket. That must be the Ring; what an evil chakra… Sai thought. The other Hobbits lit a cooking fire and began to cook. An hour or two had passed before the Wraiths began their advance, homing in on the fire. By that time, Frodo had woken up and, screaming in horror, stamped out the fire. The Wraiths screeched and advanced even more quickly. The Hobbits scrambled to the top of the tower, and Aragorn was still nowhere to be seen. Sai cursed; he might have to step in on this!

On the watch tower, it was getting bad. The Wraiths had dismounted their evil steeds and were climbing the tower on foot. They reached the top with their long swords drawn, and finally began their attack. Two swept aside the Hobbits who had formed a protective ring around Frodo. Pumping chakra through his feet, he sprinted up the side of the tower. The Wraiths were advancing on the helpless hobbit. Suddenly, Frodo's chakra levels, which been slightly below that of a normal human's, skyrocketed. Sai cursed again. He must have put on the Ring, he thought.

Vaulting over the low stone wall surrounding the tower he was just in time to see the wraith sink a dagger into the air. There was a scream, and Sai assumed that Frodo was there. The words mission failed flashed through his mind, until Frodo was suddenly visible and moaning in pain. Still alive. Sai concealed himself behind another wall, rolling a single light bomb into the midst of the Black Riders. It would stun the hobbits and keep them from doing anything stupid, and it would chase away the Wraiths, killing two birds with one stone. Or one bomb.

The bomb exploded. Even with his eyes closed against the glaring light, when he opened them again, spots danced in his vision. The Ringwraiths, shrieking, fled, retreating into the safety of the shadows, while the hobbits lay prone. Frodo, on the other hand, was gasping, making short agonized sounds, while grasping his shoulder.

Aragorn returned from his scouting mission almost as soon as the light had faded. "Frodo!" he shouted, seeing the blood flowing from the hobbit's wound. In a bound, he was at Frodo's side. Aragorn picked up the remains of the black knife used to stab the hobbit. Runes and sigils ran up and down the blade, and there was a notch missing at the tip. Sai, from his vantage point behind the stone wall, watched with interest as the knife turned to smoke and blew away, leaving only the handle.

"He was stabbed with a Morgul blade." Aragorn snarled. The other hobbits were beginning to move again. "Tell me everything, quickly! What was that light shining from the tower?"

"We don't know." Merry said, rubbing his eyes. "At least I don't. What about you, Pippin?"

"No." the youngest hobbit shook his head fervently. "My eyes hurt…"

Sam stumbled to his feet. "Instead of bickering about the light, let's get Mr. Frodo some help!"

Aragorn picked Frodo up, having a care to the hobbit's injured shoulder. "It drove the Black Riders away, at least. This wound is beyond my skill. We'll have to get him to Rivendell." They moved away from Sai's position and down the steep sides of Weathertop. Clambering down himself (walking down the side of the tower) Sai once again melted into the night. It was as if he was never there, and only the memory of the light that flashed above Weathertop remained.

Done with the first chapter. If people like it, I'll keep writing. Also, check out my other story, Protecting Harry Potter, if you are a Naruto/HP crossover fan. Characters include Gaara, Naruto, Temari, and Sakura, and obviously, the Golden Trio. Please review!