A/N
This is my first AU fic, and the first I am posting on here.
1 Ryo = 10 yen, roughly 1p, so go from there.
And Sai is 20, Yamato 28, Kakashi 32, and then their generation's ages are also changed to suit this.
Pairings: Based on YamaSai, but others will feature in the background or for plot devices.
Warnings: Well, as I said, Sai's a prostitute, and it's not detailed to feature every goosbumb, but more than just stating what happened. Warnings for sex, drugs, drinking, swearing, fighting and general unpleasantness.
I own: Nothing.

"So what is the article on?" Asked Sai
"Oh just all the Christmas bullshit we have to put up with" Answered the writer of the cultural section, Kakashi Hatake. "Pretty much the same rant as was featured last year. Could just have re-submitted the same thing again" He sighed "But Jiraiya would pick up on it. Anyway, I guess for an illustration, just something generically festive would do. But it's your call"
Sai smiled back and excused himself after taking the article copy from Hatake. Sai was the in-house illustrator for the Konoha weekly; the city's 3rd biggest newspaper. However, there was only three, and they had become a bit of a laughingstock.
It didn't pay well. At all. It was more of a part time job, if that, and now the paper was in financial trouble, they cut down so each section was only a page big, and if there was in important article, it might be blessed with a double page, thus the room for illustrations had declined, as did the work, and the pay.
However, the work itself wasn't too bad.
Mostly working with Hatake in the culture section, and the occasional caricature of a sportsman for Gai Might, in the sports section.
Sai sat at the bus stop, fortunately it had a bench and a shelter to keep him out of the early November drizzle. He lit a cigarette as he waited.
16:37
Inbox [0]
Email [0]
Was worth checking. Seven minutes to wait for the damn bus. Hopefully, in a few years he would have saved enough to buy a car. But going straight into industry rather than getting a degree, according to one of Hatake's previous articles; he would have to work another 7 years before making even the minimum that a graduate made.
Hence why even when he did get hired by Jiraiya, he didn't stop taking on clients in the evening.
It brought in money. He didn't care that he was selling himself. It was a way to make money, and he could do it, so why not? It helped get him though school, before he finished, he managed to keep it away from working at the paper now, so why should he stop? He didn't care what he got called, prostitute, rent boy, whore, slut, dirt. It paid.
Inbox [1]

Oakwood Inn
8pm. x
Sai laughed. He was predictable. He'd been a client for a year now. The ones who kept coming back were always better than the sudden pop-up perverts.
At least paid for hotels, rather than having Sai mould himself around the back seat of the man's car.
He got home, and the normal routine set in, shower, bit of food, get dressed, go out and work.
The illustrations for Hatake could be done in a few hours, quick generic festive image, do it when he got back in, when he was buzzed up and more creative.
Setting aside his shirt, sweater and smart jeans getup he wore to the paper, he put on his clothes for working the night.
It was almost like a costume. Black jeans that were tight enough to be another layer of skin, as was the raw-edge low-cut purple t-shirt. The eyeliner went on, he ruffled his hair into a mess before grabbing his leather jacket and heading out.
Inbox [1]
Iwate Endo
Bridge Street, ASAP.
He text back an agreement as he walked down the stairwell. It wasn't a nice apartment block, it was the sort of place you would expect to find junkies, rent boys and those involved. In fact, he recently figured out that the apartment below him was being used as a meth lab.
Bridge street.
Iwate was sat in his car. Typical banker. He took his wedding ring off when Sai was there, but the indent remained, as did the greying hair and dark rings around his eyes from keep up the straight act to his family.
"Hello" Sai smiled as he climbed into the car.
"Need to be quick" He ordered as he climbed into the back to join Sai.
Sai's jeans were around his knees in a few moments. Iwate was very eager, and didn't even let Sai prepare himself. His nails dug into Sai's lower back, releasing and digging in each time he forced himself on the boy.
He was a regular, but completely impersonal. Didn't kiss, hardly touch Sai as he fucked him, finished quickly, paid, and then ordered the boy out of the car.
That was the easier type of client, where Sai didn't have to talk, to pretend to be swept of his feet.
But he could. Better than most actor's he'd seen.
He walked down to the corner he frequented, and stood, and waited for the people to come up to him and want something.
And now, there was one. Tall build, tanned, beard, wedding ring and neat clothes. Sai shifted and smiled at the man as he came over.
"Hello" Said Sai.
"Have you seen this girl?"
Shit, police.
"No" Sai answered, instantly.
"You didn't look at the picture"
Sai pretended to glace at what he was holding up.
"No. Never"
"How about her?" The policeman brought out another photo.
"No"
"Fine" The man looked his up and down with a disapproving look. It didn't take and minute to figure out what Sai was doing on the street corner, hence why he often got dirty looks from people. "Well they were both prostitutes, went missing five minutes from here. So be careful"
"Alright"
The man left and continued down the street.

Sai got to Oakwood in at 8. It was a rundown hotel, at its best, it was ranked 3 star, but that was decades ago.
Getting to 's room, he was greeted by someone in pretty much the same situation as Iwate, but he was a nicer man. He would want more than a shag; A kiss, a bit of foreplay, a fuck then a bit more kissing. He knew Sai's rates and paid for it all, with a tip, which covered the cost of Sai's acting.
"Hello, Sir" Sai purred, as he wandered over to H.
"You look sexy as ever tonight, Babe"
"As do you, Sir"
H pushed him back onto the bed, slipped his hand up Sai's shirt and tenderly started kissing him.
"Do you want to fuck me, Sir?" Sai asked when the kissing stage was done.
"Not yet" H smirked "Strip"
Sai did as he was told. Once naked, straddled H and rubbed his cock through his suit trousers. "What do you want now, Sir?" He pouted. H held back a moan and Sai could feel the older gentleman's manhood growing hard.
"You know what I want to do now" H laughed. It was routine; what they did. Sai didn't have to ask.
"Can you fuck me with your hand, Sir?"
"Of course" H slipped a finger into Sai's ass. Sai squirmed a bit. Iwate had left him sore. But he managed to make the squirm look like he was enjoying it. He didn't get pleasure from it, he never got hard when he was with his clients. He had a lie about a pretending medical condition which prevented him from getting erections, which was why he let people fuck him, because he couldn't fuck them, and the clients brought it. But of course, if one of the clumsy idiots managed to hit his prostate, it would shock his nervous system, but that was pre-programed into his body, and now, after being fucked so much, it took a lot to get him off, so when they fucked him, he would act like they were the best he had ever had.
"Oh!" Sai moaned. H unzipped his trousers and pulled his cock out, then took Sai's hand and wrapped it around before pushing another finger into him.
"Maybe- ah" H groaned "I'll try fisting you sometime"
"Cost 15,000Ryo" Sai said, automatically. It had happened before, left him too sore to work for a week.
H laughed "would you moan?"
"Yes"
"Would-ah- you cry"
"MMhm"
"Would I get to see your perfect little face as I did it"
Sai faked another moan "Yes- oh!" He could see H pondering the idea, before he lent forward and bit on the boy's nipple. "Sir! Oh! Fuck me!" He faked it again "Please!"
"Suck me"
Sai climbed down off the bed.
"Wait-, pass me my trousers" H ordered "Okay now suck"
As Sai's plump lips wrapped around H's cock, he watched the other man check the notes in his wallet, then grinned as he laced his hands in Sai's hair and thrust into Sai's mouth.
He then pulled Sai off, ordered him onto the bed, rolled on the condom and lube and started fucking the boy.
But before he came, he stopped, and pulled out.
"Sir- please don't stop!" Sai protested. Clients seemed to enjoy it when he begged, H especially. As Sai had figured a few months ago, H was infatuated with him. Begging and acting got him tips. You could pay, for dirty talk, H sometimes paid Sai an extra fee, so that he could phone if he were away they boy and talk to him. "Please- Sir- I need you inside me" Sai cried.
"Then you can have me inside of you, you perfect little slut" H whispered into Sai's ear as he pushed two fingers back inside his toy.
"You want to -urgh- to fist me then, Sir?"
H forced his tongue into Sai's mouth.
"What do you think, sexy?"
"It's your money, Sir-Ohh!" H pushed in a third finger. He grabbed Sai's hand and directed it to start pleasuring his cock.
"Oh you're a good little slut aren't you?" H asked as he began stretching Sai more.
"Yes, Sir"
"You want me to put my whole hand in?"
No.
"Yes! Oh! Please! I want you to put it in!"
H picked up Sai's left leg and placed it over his shoulder, then quickly forced his full fist into Sai's ass.
Sai, at that point, stopped giving his body orders. One hand was clinging to the cheap bed sheets, the other squeezing H's cock.
"Oh my god!" It hurt. H started moving his fist at the same rhythm Sai moved his hand at. Sai felt something wet roll down his face as he moaned in the pain, barely able to make it sound erotic.
"You're my whore aren't you? Mine." H moaned "Fucking look at you- urghhh- you can't even- mmhhmm- speak- oh- Oh! Sai!" H came, then slowly pulled his hand out of the boy.
H didn't move for a few minutes, just watched Sai as he recovered.
"How much?"
"40,000" Sai groaned and started pulling on his shirt "How much longer have I got the room for?"
"An 20 minutes. This place has a ton of prostitutes, so they do by the hour" He gave Sai the contense of his wallet "Here"
"Get out"
H left. Sai painfully pulled on his jeans. For a moment, he considerd doubling his rates, but H would pay, anything.

Sai made his way home. After dealing with , he always found himself in a foul mood, even why he didn't try and rearange his internal organs.
A few minites from home, and he spotted a crowd. Outside his arrartment block. Two police cars, and a firetruck.
He staggerd up to one of the officers stood outside.
"What happened?" He asked.
"There was a fire" The officer replied, he was old, tired, and wanted to go home.
"I erm- Live here"
"Oh" The officer sighed "Well, come in with me"

Sai followed him in, making his way to his appartment was like one of the longest moment of his life.
The walls got blacker and blacker and the damage done increased.
When he went to open the door, he found there, was no longer a door to open, but all he saw was a black, burnt room with remnents of objects.
"Have you got somewhere to stay?"
"What happened?" Was all Sai could answer.
"That lab in the flat below you. I don't know the details as of yet but- Have you got insurance?"
"No"
The officer laughed "good luck" and left.
Sai walked about, examining the damage. There was nothing left. All his artwork, clothes, books, everything had been eaten by the flames.
He left the building, there was no point staying around, he had nothing but his wallet and phone.
Sifting through his contacts on his phone he found more clients than anyone from the real worl.
He didn't have any friends who would let him in, the only person he knew from school was Shikamaru Nara, and only because they shared the same smoking spot on the school roof, and spoke there. Sai hadn't heard from him since he left school, and his father was on the local concil, and was opposed to solicitation, and could spot a slut out miles away. That was a no go.

Kakashi Hatake. When Sai first started working with the paper Hatake had said 'If you ever need anything, you can ask me'.

He got to Hatake's door. Rather than phoning him, Sai just walked over and tried to think of something to say, but he realised that he was in shock, and logicial thought was impossible. Kakashi opened the door and gave Sai a quick up-and down look.
"Hateke, Sir- See there was a fire and- My appartment-" Sai stumbled over the words.
"You look like shit" He deadpanned.
"Yeah…" Sai sighed.
"Come in" Kakashi placed a hand on Sai's shoulder and lead him in "Oh and, don't call me 'Hatake' or 'Sir', just Kakashi alright?"
"Hm" Sai starred at the floor.
"Oh erm, this-" Kakashi to the man sat with a drink at the table "-Is my friend, Yamato"
"H-hello" Sai stutterd.
"Take a seat" Kakashi indicated to the sofa, Sai complied.
"Is everything alright?" Asked Yamato. "Shall I?" He indicated toword the door.
Sai took in a jittery breath; "Stay, if you want"
Kakashi and Yamato exchanged a few looks, Yamato went to the kitched and put the kettle on.