-A/N: Even though I've only seen Pretty woman once and really long ago, some inspiration is obvious, hopefully put into good use

Warnings: Prostitute!Dean, no slash except explicit Wincest, though. They're also unrelated in this story. And there's nothing dark in it.

I hope you'll enjoy reading this and leave a comment, when you leave-

Disclaimer: The boys and nothing of the Supernatural show belongs to me If you recognize some characters or dialogues from the show, then I confess, I borrowed a little.

Thanks to Kinthinia for her help.

Chapter 1

Dean was released from hospital after the attack just yesterday and Riddley was already forcing him to go back on the streets. Riddley was the "owner of the street" and he wasn't that bad. He would look after his 'investments' as he would call the prostitutes (he did pay for Dean's three days vacation in the hospital after all). But according to him, three days were enough, so here Dean was.

Thanks to his looks, Dean had the luxury of being able to choose between his customers most of the time, so he figured if he stayed out of trouble, he should be fine. But then again, you never know you're in trouble, until it takes you home. Dean had found himself in situations, that left him rather bruised and sore a couple times before, but he'd heard stories and seen things that made him consider himself lucky that was all it was.

First potential customers were arriving and choosing their 'caretaker' for tonight. Dean was just leaning against the wall, eyeing the newcomers curiously and deciding whether he would reject them or go with them if they asked. That was one of the few rules of this street: Don't ever approach a customer, let them choose you. Dean was 'lucky' enough to be picked almost every night he was offering himself.

He watched a man in his mid-forties approach a girl he knew as Lily. She giggled and batted her lashes. The man leaned to her ear and whispered something. Lily's eyes widened in surprise and then she smiled and waved on a girl with blue hair standing nearby. She walked toward them, all three of them shortly discussed something and then the man was walking away with both girls on his arms.

Dean spotted a guy on the end of the street that somehow stood out above others. He was freakishly tall, shaggy hair, soft features. Dean caught himself wondering what a guy like that would be doing here, since considering his appearances, he shouldn't have any trouble getting laid. His clothes screamed 'money'. Dean couldn't recall ever seeing anyone like him down here before. Young spoiled brats usually got off in clubs; the customers here usually came out of despair, unhappy marriages or to 'try something new'. And they were definitely older, poorer or uglier.

Dean wasn't the only one to notice him. All the hookers, both male and female were watching him and showing themselves off to be picked by this guy. Dean could understand why. He was a pretty young thing and if he was rich, it meant a good place to spend the night. Men with money usually had a certain level of standards and picked hotels and rooms according to it.

Dean could see the women winking and blowing kisses as the man walked past, pushing their breasts out, showing more of their already not very covered figure, while the men smiled seductively and flexed their muscles.

Even Dean pushed himself off the wall and adjusted his shirt, so that his bruises weren't showing. He was pleased to notice, that the young man was looking at male prostitutes only, and hadn't stopped to talk to anyone yet. The attention he was getting seemed to make him uncomfortable. He was concentrating on the concrete beneath his feet, clutching his hands nervously and looking up only to do a quick once-over and then he quickly went on.

As he was getting closer, Dean had a chance to look at him properly. He was taller than Dean, that was for sure. His body was lean and lanky. Not as muscular as Dean's, but not scrawny either. His skin was olive-tanned. When he looked up, Dean could see the proud line of his jaw and perfect cheekbones, but before he could take a proper look at his face, it was covered in the dark mop of his long hair again.

Then he finally looked up to check out Dean, too. He seemed even younger from the closer distance, early twenties was Dean's best guess. There was something in the way he looked at him, almost as though Dean was exactly the one he was looking for, as thought he already knew him. But Dean would remember meeting someone like that before.

The guy went straight to Dean, ignoring all the other men on his way, but when he finally reached him, he looked down at the ground again and his voice came out forced.

"I, uh, would you...come with me?"

Then he looked at Dean, smiling shyly. Dean actually thought it was cute. If he wasn't expecting something from the people, that came here, it was bashfulness. He wondered if this was the first time the man found himself on a place like this, because his behaviour sure seemed that way.

Dean loved first-timers. They didn't know what they were allowed to demand or want, so Dean could pretty much have it his own way and that was how it suited him the most.

"Sure thing, sweetheart," he winked and he could have sworn he heard the jealous hisses and growls of his rivals. He also noted that the guy blushed. It made him look even younger, like a child lost on his way from school. A really overgrown child, but still very out of place.

He quickly glanced in the direction, where he knew Riddley's boys were hidden behind the corner and nodded to confirm, that he was leaving with this guy. As said earlier, Riddley was looking after them. His guarding dogs, as they were calling them, were there 'just in case'. For example, if someone decided to rob a prostitute of any money they might have. It happens. It happened to Dean. Too bad, he was too far from the street for Riddley and his dogs to see, when the muggers attacked him. His fault for taking the shorter route home to his apartment, he should have known better. That was how he ended up in the hospital three days ago.

They walked to the guy's car -a nice and expensive looking Chevy- and when they were on the road, the man finally spoke again.

"Uhm...this is gonna sound really weird, but I was wondering if it was possible to buy you for...like a week, maybe?"

Dean raised his eyebrow. He got used to being treated like a thing rather than a person long time ago, so the sound of 'to buy you' didn't really offend him. He just didn't expect it from this guy. Maybe he wasn't as innocent as he made himself look.

"Dunno, darlin'. Gonna have to check with my boss first," he said and opened his phone to text Riddley.

"Tell him that Wesson's paying. That should chase away any doubts he would have about if I can afford it," the young one said with a smile.

Dean froze. Wesson, shit! He should have known! Of course, a young good-looking man picking him up with no hesitation? Shit, he should have known better than to think that he got lucky.

Everybody knew the name Wesson. The face of Don Wesson was everywhere; he was an owner of some big company and made an unholy amount of money. This was probably his son, nephew, or something. And rich boys always meant trouble.

The only time they pick hookers from a street is, when they want to beat them, cut them and tear them to pieces, possibly without killing them. And they always pay enough money to both the hookers and their pimps, so that nobody ever complains. Why today?

Young Wesson wants to buy me for a week. U okay with that? Dean texted Riddley.

Try not to get into hospital this time, have fun and take care. Was the reply he got.

"Okay, it's official, I'm all yours this week," he tried to sound excited, but he was feeling a little sick.

He studied the man's face. Wesson never let his eyes off the traffic and when Dean had told him he could have him the whole week, he smiled. Dean was looking for something evil in it, a grin, a twinkle in the eye, maybe, but the smile seemed genuine. It was more relieved than anything else, as though he expected to be denied. As if anybody would say 'no' to a Wesson.

When they reached Wesson's place, it was nothing like Dean expected. There was no driveway, no fountain in a large garden, no servants running to see if their master needed anything. Okay, maybe Dean didn't really expect servants, but what turned out to be Wesson's house was so ordinary, it was almost disappointing. You could walk right past that house, not giving it a second thought. It was white, one floor, stuck at the end of a street full of similar white buildings.

Inside of the house, it wasn't much different. There was a door to the right, a room right in front of the main door, that was both kitchen and living room. It was mostly white and clean, but from the glimpses Dean got at the furniture, it was some fine designer's work. And to the left there was a long corridor with more doors. Wesson walked to one on the end of the corridor. Dean followed him, because what else was he supposed to do?

Wesson opened the door and held it for him. The room looked like a guest bedroom.

"Make yourself comfortable," the guy said. "Oh and my name's Sam," he smiled and reached a hand towards Dean. Like they had just met in a bar and exchanged pleasantries. Like they were equals.

"You've never done this before, have you?" Dean laughed.

Sam frowned sheepishly.

"You can call me Antonio," Dean shook his hand.

Sam grimaced at the alias Dean was using, but said nothing.

"When you said 'make yourself comfortable' you meant..." Dean tried to find out what it was that Sam wanted from him.

"Right, uh, I don't know, there's a bathroom," he pointed to a door on the other side of the hallway, "take a shower, if you like? And then go to sleep, I guess. It's late."

Dean blinked.

"Sleep? Like peacefully sleep by myself? Are you sure? You have to pay for every night I stay here, not just the ones, when we...you know. When I'm working."

Sam just shrugged and looked at him helplessly.

"You were right, okay? I've never done this before," he sounded a little like he was pleading with Dean not to laugh at him.

Dean smiled. Maybe he was going to cut his beaten body some slack, at least for a day or two more.

"Okay, look, here's the basic rules: I do not kiss on the mouth. You can either pay me on the end of the week, but then you gotta cover my expenses, or you can pay me on the end of every day, up to you. Also, please, either show me a signed paper from a doctor that you're STD free or use a condom. I got myself checked last week and I'm still clean. And I had an accident last week, so I'm all bruises and stitches, so if I could ask you to either be gentle or wait with the hard stuff for a few days, that would be great."

Sam's eyes widened.

"H-hard stuff, no, I don't-"

God, this boy was either too sweet for his own good or a really great actor. The really rough guys were usually assholes and Dean allowed himself to hope, that since they were already here and Sam didn't have any obvious reasons to keep pretending, this might actually work out pretty well for him.

"Hey, it's okay, sweetheart, alright? I'mma go take the shower now and I should be ready in like 30 minutes or so, if you want to come," he smiled seductively at now dark red blushing Sam.

"No, not today. Just get some rest."

And with that, Sam just walked away leaving a bewildered Dean behind.

Well, Dean was certainly not going to look a gift horse in the mouth. He walked into the bathroom and he heard Sam in the kitchen, but he didn't pay much attention to him. Dean closed the door behind him and looked around with an opened mouth.

If this is where all the money from buying a house went, then I get why he couldn't afford anything bigger than this, he thought.

The bathroom was about the same size as the apartment Riddley was providing him. There were a bath and a shower, sinks for two people, shelves with bottles of all possible shapes, sizes and contents. There were towels, too. White and soft like Dean had never seen before, let alone used. Dean slapped his forehead when he remembered that he didn't bring anything with. No clothes, not even a toothbrush. He could try out Sam's seeming kindness and ask him to buy him one.

He still didn't know what Sam was up to and it was unnerving, because Dean always thought himself as capable of reading people. It was fundamental in the life he was living.

Well this is going to be an interesting week, Dean thought as he stepped into the shower, that had six heads instead of one, and many tempting buttons, that Dean was curious about and for the next thirty minutes he allowed himself to forget about what was yet to come.