Author's Note/Disclaimer: Tried for an angsty piece as my first fanfic. Feedback appreciated :]
I do not own Naruto nor am I in any way affiliated with Kishimoto Masashi.
It hurts. He will never admit it, not to the village, not to his teacher, especially not to his god-awful, obnoxious, childlike pupil who is stronger and more full of hope than Jiraiya ever could have been.
But it hurts.
When the black blades jab into his skin, and he claws at his throat but cannot cry out for the Sannin, for Tsunade, for everything he once lived for; when he can only taste the red running down his lips—blood, not wine—it hurts him more than anything.
He thinks then of Orochimaru, the one he could not save from the darkness, running away from the harshness of the light to seek comfort in the shadows. Ill-suited for the life of a shinobi, Jiraiya has often thought scornfully during the era of Team Hiruzen when Orochimaru is hailed as a prodigy while he watches indignantly from the sidelines. It is only afterwards, when what remains of the snakeman is mere hushed whispers spinning tales of his silhouette, that Jiraiya realizes he is his closest friend.
Too late. Everything he does is too late; too late to save the third Hokage, too late to save the fourth. It is too late for him to become Hokage himself, but some nights when he has had too much to drink he looks up at the faces and pictures himself up there, beside his teacher and his pupil. He knows that the power will lead him astray just as it did Orochimaru, that it will corrupt him inside until he loses control. He knows, and that is why he persuades Tsunade to come back. But on those nights, drunk and lonely and growing old, Jiraiya regrets.
It is too late now for even his desperate fantasies. Hoping against hope, he has wished that she would come to him one day. Jiraiya has watched as Tsunade fell in love with Nawaki, fell in love with his dreams of becoming Hokage and his impossibly bright smile. Jiraiya has watched as Nawaki's death broke her, and then watched again as she found comfort in Dan, giving her unwavering support for the goals that her brother was unable to achieve. Jiraiya is not able to watch when Dan is killed and Tsunade has left, even more broken. He only hears of it from his teacher when he returns to the village after his stay with the three orphans; he has come back, only to find Tsunade gone and Orochimaru fled. Too late.
In vain he runs after Orochimaru, but now Jiraiya regrets not following Tsunade. When he is sent to search for her with Naruto alongside him to offer her the position of Hokage, he hesitates, because he knows that she will fall in love again while he stands by, forever unnoticed. He goes anyway, and for the final time he watches as Tsunade falls in love with his student. Perhaps if he had become Hokage, she would want him. Perhaps if he had been there to support her after losing Dan, she would realize. But as always, he is too late.
Those nights when he drinks himself to sleep, when his mouth tastes bitter with ash; on those nights, regrets spiral together into a whirlwind until it breaks him.
So instead he loses himself in women, allows himself to indulge in such pleasures as he forgets his mistakes for even a moment. With the help of a bit of sake, he is able, too, to forget that the women he frequents are tavern whores. But only for a moment. When the magic has wore off, it all comes back to him, and he wishes it were Tsunade.
His biggest mistake stands before him, spiraled eyes dizzying Jiraiya's dwindling vision. Nagato. For long Jiraiya has believed them to be dead; the three children that he had once trained, so long ago. Now he knows that one is, and the other two aren't children anymore.
His failures weigh him down, or maybe it's the black blades crushing his back that make him fall to his knees. The white tears mix with the red ones and spill across the ground, staining the soil with that rosy hue. Before dying, Jiraiya remembers that pink is Tsunade's favorite color.
It hurts, so he closes his eyes and hopes it will be over.