"Immortality from time looping is not all that the fox said it would be,' Naruto thought as he opened his eyes and looked around. He turned out to be 13 this time. At least he did not have to live through potty training again.
Each time the fox sent him back to relive his life he ended up at a different point. He stopped counting after it had happened one hundred times. Each life was different from the last but always after the fox had been sealed into him. He had awakened once to hear his parent's last words to him and even once he had awakened as an old man who died seconds later. It got quite boring living the same thing over and over so he tried to make each life into something unique.
He had been with every girl he had ever known at one point of another. He had even bagged Tsunade once or twice. One of his more favorite incidents of all his lives had been when he had awakened the morning the Sand Siblings first arrived in Konoha. Temari had turned her nose up at him when he just snapped his fingers and a perverted jutsu he had learned a few dozen lifetimes earlier found a use. Her panties suddenly were teleported off of her and into his hand. The 'eep' and blush of the blonde teen was the sole bright spot in that very brief lifetime. Gaara had crushed him to death seconds later.
As the cycles grew in number he eventually learned more jutsu than Orochimaru could have ever dreamed of and most he really didn't care for. Jiraiya alone had developed over one thousand that he knew and each lifetime the pervert surprised him with creating new ones. Heck, he could make any girl his willing love slave with a single touch behind the right ear and applying of the right frequency and amount of chakra. He had done that to all the girls in his graduating class once. The loop after he had learned it, he was fed up with the cries of 'Sasuke' the fan girls would chant. But explaining to the Hokage three months later why nearly a dozen 12 and 13 yr old girls were calling him 'Naruto-sama' while pregnant with his children was something he did not want to repeat.
Beyond girls, he had a decent relationship with most people he cared to know over his lifetimes. All of the people except for Sasuke. He had done more to help that ingrate in any life than he had done for himself. He had saved Sasuke's family from Itachi countless times, prevented the curse seal, stopped the defection. But no matter what Naruto tried, the boy simply refused to have a decent and happy life. In spite of aiding Sasuke, the boy ended up working for Madara more often than not. It was always this or that issue cropping up. Naruto had finally just left the Uchiha alone to be miserable each time.
He looked at the date on the calendar over his bed. This time he woke up on the morning before Jiraiya would take him on his training trip. He could at least make it a lively morning as he put himself on autopilot to prepare the things he would need from his limited supply on hand.
He chuckled lightly. This time he would turn back at the last moment and kiss Hinata instead of look at the monument of his dad. Maybe whisper something about how he loved strong girls and that he hoped she would be able to defeat an S ranked ninja upon his return while hitting her with an orgasm jutsu. Hinata always surprised him after his trip when he did things to inspire her before leaving.
He picked up his pack and headed for the door to make the best out of this next lifetime of his repeating immortality.
Comments: Just a short take on an isolated scene Naruto could have by looping back into his own lifetime. Consider it an omake and it is not going to be continued. Also writers could consider the idea of Naruto looping back to a random point in canon each time instead of to a consistant point.