Naruto first saw him the day of the infamous bell test which marked his first true day as a Shinobi of the Leaf. The boy couldn't have been more than nine years old, and most embarrassing, they both were about the same height. Someone had somehow managed to tie the boy to the post next to his and leave without him seeing them.
They both struggled with their bonds for a while before the other boy noticed he was there. After he got over what seemed to be shock at not being alone, the other boy started laughing over the fact that they both were in the same predicament. They both laughed together as they struggled to be free. Apparently, the people who tied them to the stumps had done a very good job, and neither of them had picked up the rope shredding technique at the Academy.
Eventually Naruto got loose. He stood up to stretch, and when he turned around to free the other boy, the other boy was gone, apparently having freed himself and left while he wasn't looking.
Naruto saw the boy several times afterward. For some strange reason, the boy would come running up to the team meeting place anywhere between fifteen minutes after the day's training was supposed to start to about a minute before Kakashi arrived. Sasuke and Sakura never seemed to notice him even though he was loud and apologized for being late before looking slightly puzzled, turning around, and leaving.
The strange thing was, every time he apologized for being late, he gave the exact same excuse for his tardiness that Kakashi-sensei gave when he was confronted for his tardiness when he arrived later.
Naruto ran into the boy once or twice while he was on the road, but the boy was always too busy to talk to him because he was on a mission. Knowing how missions could get, he wished the boy luck before he ran off only to disappear before Naruto could reach the corner the other boy had run around.
The last time Naruto saw the boy, he was sixteen, and the boy thirteen. He'd just gotten back to Konoha after his training trip, and had been wandering around in order to reacquaint himself with the village. The boy asked him what what sort of present you would buy for a Jounin, and he'd asked which Jounin. When the boy replied that it was Hatake Kakashi, he replied "Oh, that's easy..."
&!&!&!&
Hatake Kakashi had just become a Jounin that day. His sensei Minato gave him a special kunai to celebrate his promotion, and Rin gave him a medical kit.
When Kakashi reached out to Obito for his Jounin present, he turned around and rummaged through his pack until his hand found the wrapped gift. He almost hadn't gotten it, and then he'd almost left it at home, but fortunately he'd remembered it at the last moment and raced back to get it before the team left the village.
"I couldn't find the series by Jiraiya that the blond boy was talking about." Obito said as he handed the gift over "But, the guy at the bookstore assured me that this one was good."
Kakashi stood there staring at the present he'd just unwrapped as if it were the most horrifying thing in the universe. Rin and Minato ran over to see what it was that had so shocked their teammate/student.
"I don't believe you Obito!" Rin yelled. "You gave Kakashi PORN? !"
&!&!&!&
Author's Note: Flareose wanted something with Naruto and Obito in it. This wasn't exactly what she wanted, but hey, it's got Naruto and Obito.