Full Summary:
It might not have been his greatest plan but it had… it had been working. Step 1: stay far away outside of the village. Step 2: avoid everyone that he had ever hurt. Step 3: die on some desolate part of the continent without ever having to suffer the embarrassment of apologizing. Step 4: profit. Now if only Naruto had gotten the damned memo.
Here's the short and the long of it: Naruto, in his infinite wisdom upon ascending to the seat of Nanadaime Hokage, has assigned Sasuke an undercover mission in the Land of Waves, 15 years after Team 7's first mission there. It is routine almost to a fault, until Sasuke has the misfortune of meeting his backup: a man who has the very distinct misfortune of looking like one newly retired Rokudaime Hokage.
Note: For timeline, let's say Kakashi was Rokudaime Hokage for roughly a decade, starting about a year after the 4th Shinobi War. That would make Kakashi 42 years old and Sasuke 27 years old in this. Just as an FYI.
The Land of Waves has prospered in the intervening years between the initial efforts to construct the Great Naruto Bridge and now, some decade and a half later. If the land had not been one of the earliest memories seared into Sasuke's mind with Sharingan precision he might not have even recognized the village just on the other side of the bright. What had once been a misty ruin of a place is now lush with mangroves across the coast and a port town so large it can be considered a city, teeming with goods and people.
Unfortunately profitable trade meant now exactly what it had meant then. There had been word that various groups had been trying to establish trading monopolies ahead of the proposed construction of a second bridge, which would account for all the additional traffic.
Sasuke has been here for the past several weeks, under the guise of Yusuke, who is a wandering artist who has come to the village of Tosashimizu for Inspiration with a capital I. So far he has been unhindered by the formalities of Konoha missions: no genin team, no ANBU squad, no strict mission parameters. Just Naruto and his trust that when he tells Sasuke to deal with some that Sasuke will, in fact, deal with it. There were teething pains of course, what with Naruto being so new to office, but the arrangement as established under Kakashi's reign has worked well enough so far.
Yusuke has been around looking in all sorts of places for Inspiration. He had relayed his findings like the dutiful Konoha shinobi that he is, and he had been told that a contact had been dispatched to help deal with the situation. The Situation, being one so exceptionally similar to the one from fifteen years ago it was almost uncanny, with hired missing-nin and all.
Sasuke could have, of course, taken care of them himself, had he really wanted to. But that would have meant absolutely no subtly at all if he needed to pull out the jutsu that had been so thoroughly associated with him as a consequence of the Fourth War, and that would completely and entirely defeat the purpose of an infiltration mission in the first place. He was not going to waste all this effort he had put into carefully crafting his waffish starving artist persona, and his missing arm was really the cherry on top in selling Yusuke to the locals.
He might have sold Yusuke too well to the locals, and there was something deeply funny in how much they had believed in his disguise. It is perhaps over-stating it to call his appearance a disguise, especially when Yusuke really looks just like Sasuke, but to the left. Yusuke still has hair so black it looks blue, and he still has bangs covering his Rinnegan, but he has carefully grown it out such that it swings around his shoulders whenever he walks. Yusuke even wears the colors that Sasuke has been wearing his entire life, blue on top and white on bottom, but now it's all civilian clothes with their light-weight fabrics and their dubious stitching. Button-up shirts are, as he has found, exceedingly annoying, especially now that he has only one arm, and jeans… Well, the less said about them, the better.
This has all culminated in Sasuke standing out here on the Tosashimizu side of the bridge, offering to draw caricatures of whoever is willing to sit and pay him a handful of ryo. Whereas the Sharingan might have pushed him towards precision, had he been using it to look at whoever has the dubious pleasure of "commissioning" him, he takes delight in exaggerating whatever features he feels like exaggerating, and whenever a visitor goes to complain a local is quick to bring up Yusuke's situation. Unexpected benefits of being known as a starving artist that would never turn down a free meal he supposes.
Just as the sun seems to begin its trip down and the crowd starts to disperse, a hand taps his right shoulder.
Sasuke turns.
"Yo." A man with brown hair salutes Sasuke with his index and middle finger out in a V, and a tilt of his head. For some reason he has painted his eyelids a deep purple, and has streaked that exact same color half way down his cheeks. His eyes are an odd sort of muted green that are so dull they are almost gray.
Sasuke squints. If this is Naruto's idea of a joke, it's not a very funny one. He takes a fortifying breath. "Hello."
The man, who can only be one Hatake Kakashi, Former Rokudaime Hokage Extraordinaire, smiles and Sasuke sighs some more. "I couldn't help but notice that you're drawing portraits."
Sasuke could be the Land of Wind for all that this conversation has him sighing. "I was offering portraits but it is very late now, sir."
"I'll pay." The bill Kakashi waves in front of Sasuke's nose is several times more than anyone else has offered, and Yusuke of the Great Naruto Bridge would not possibly turn down such an award. Sasuke, intimately familiar with Kakashi's tendency to dine and dash, can only eye it with well-worn suspicion.
"If you insist," Sasuke demures. He turns the easel so that he can face Kakashi and keep the page away from the man's eyes, and he pulls out a thick black marker. Sai had suggested brushes and paints, after many, many comments about Sasuke being a dickless artless hack with not a single creative bone in his body. Maybe Sai's suggestions would have held water had Sasuke the chance and opportunity to use his Sharingan and the desire to paint something realistic. Chunky highlighter-like pens were not exactly useful for finesse, but Sai had looked like he'd swallowed lemons when Sasuke had shown off his art supply haul, and that had made the purchases all the more sweeter. He uses one now to outline the broad curves of Kakashi's unmasked face.
"Do you need me to pose?"
"You can just stand there."
Kakashi doesn't just stand there, but such is life. Of course he would pick the most annoying persona for this mission.
"How long—"
"Done."
Kakashi blinks as Sasuke rips the page out with a vengeance. They make their exchange, one portrait for Kakashi's bill, and Sasuke delights in watching the microexpressions on Kakashi's face. He wishes he could use his Sharingan.
"It's certainly…"
Sasuke smiles. "Certainly what?"
The portrait, which can only be called that by the most generous interpretation of the word, features buck teeth hanging over fish lips, and a delightfully hairy wart protruding out of the chin. Sasuke thinks it's a masterpiece, of course.
"Certainly unique." Kakashi secrets it away somewhere on his body, probably never to let that piece of paper see the light of day ever again.
"One of my best pieces, I assure you."
Kakashi grimaces before smoothing his face out into something more approachable. It might have worked on someone else, but alas. Sasuke has the unique displeasure of knowing the man, and trying to figure out his expressions through a mask. "Maybe I can take you out, as thanks for this wonderful work of art."
"My, how forward!" Sasuke titters behind a hand, and goes to push his bangs behind his ear. "I don't even know your name, Mister Stranger."
"How rude of me." Kakashi bows deeply, as if anyone is supposed to take that seriously. "I'm Sukea."
Sasuke tilts his head. "No last name?"
"Maybe if the first date goes well."
"As if I'd let you take me on a date, old man."
Sukea physically wilts, the stringbean of a man that he is returning to the earth now that he has been starved of the sun, and he clutches a hand over his heart. Sasuke almost has to look away. "Denied! And after you made me such a lovely portrait."
"I might be persuaded to give you my name in exchange for sushi." Sasuke says as he swings his bag over his shoulder, supplies safely tucked away.
The string bean returns to full force, growing with a second wind. "I've heard they have such fresh fish out here, on the coast."
"Stating the obvious now, are we?"
"You're so cruel to me, Mister Artist."
Sasuke demures again, showing off a half smile behind his curled hand. "A man like you likes a little bit of cruelty though, doesn't he?"
"It seems that I'm not the only one stating the obvious." The string bean seemingly takes no offense and ambles down the bridge, towards the evening bustle of Tosashimizu. He gestures a hand back at Sasuke. "Maybe we can get to know each other a little more as you show me around."
Most of the people on the bridge are ignoring them. Only a few watch on, those that have seen Yusuke for the past several days with his easel and pens, but they mostly continue on, returning home for the day. None of Sasuke's summons, hidden throughout the mangroves and the town, have reported anything back in a few hours. He can feel none of the signatures he has come to associate with the budding Tosashimizu mafia nearby, and once he confirms this with a subtle flair at Kakashi, Sasuke takes great pains to shrug elaborately, letting his bag fall down his arm.
"Sure, why not."