DISCLAIMER: This is a work of fiction using characters from the Supernatural/Pretty Woman universe. I do not claim any ownership. This work is solely for entertainment purposes and is not considered film or tv canon (not by a long shot).

Dean stood in front of a guy selling knock-off watches from a card table. There were half a dozen of them within any given block – all peddling crap. Dean sighed. He wondered if he wasn't doing the same thing. Gabriel suddenly bristled and Dean looked up to see him walking toward a dark-haired woman leaning against a tree close to the curb.

"Yo, Rachel," Gabriel said, none too kindly.

"Yeah?" the woman said with a bored expression on her face.

Gabriel gestured at the sidewalk. "You see the stars, babe?"

Rachel glanced down. "Yeah, so?"

"Well, me an' Dean-o, we work Bob Hope, we work the Ritz Brothers, we work Fred Astaire - we work all the way down to Ella Fitzgerald. You need to move on, babe." Gabriel said. His shorter stature didn't make him any less intimidating when his ire was up.

"Pardon me ... I was just takin' a rest here," Rachel said. She looked over at Dean. "Besides he's new."

"Yeah, well I'm old so go rest up on Monty Hall or Esther Wilson ..."

"Williams," Dean supplied as he moved to stand behind Gabriel, one hand on his shoulder.

"Williams – where you belong!"

Rachel snorted. "Back off, Gabe – you're gettin' to be a real grouch." With that, she turned on her heel and sauntered away.

Gabriel turned and looked up at Dean. His expression was concerned. "Am I really a grouch?"

Dean could have laughed but he held it back. "Yeah, you are." When Gabe's face fell, Dean added, "Just sometimes, though."

Gabe sighed and dug one of his ever-present lollipops out of his jeans pocket. "It's just 'cause I've got low blood sugar."

Dean chuckled. A red mustang full of what looked like frat boys drove by yelling the usual insults and catcalls. Gabriel made a rude gesture and returned the insults.

The parts of the street he and Gabe worked tended to cater more toward those interested in the male body – be it a woman looking for some company or a man who didn't really want anyone to know his predilections. Dean dealt with more of the latter, although he had a couple of regulars of the female variety. He sighed and straightened his jacket.

"Lookin' pretty slow tonight, Gabe."

Gabriel nodded absently. He pulled his sucker out of his mouth and looked at Dean. "You know ... Alastair really digs you. He's got a lot of connections ..."

Dean was shaking his head before Gabriel could even voice his thought completely. "Nope. Then he'll own us and he'll take our money. No way, Gabe."

Gabriel nodded. "Yeah, you're right." He looked at Dean. "We say who, we say when and we say how much."

A squeal of tires pulled Gabriel's attention back to the street. A large smile split his face. "Yo, yo, yo Dean-o ... catch this!"

A white car turned the corner and drove jerkily past them. Dean winced as he heard the gears grinding. "Yikes ... that's a Lotus Esprit, Gabe."

"Nope, Dean, baby – that's rent! Go get 'em tiger, you're looking exceptionally pretty tonight!" Gabe said, pushing Dean in the direction of the car which had come to a screeching halt. "Don't take less than a hundred. Call me when you're through, take care o' you."

Dean looked at the car and then looked back at Gabe. "Yeah, alright ... take care o' you," Dean said, bumping fists with Gabe. It was corny, but Dean still liked the feeling that he and Gabriel watched out for each other. Every john was a potential disaster waiting to happen – if the worst did go down, at least there would be someone to identify the body and let Sam know what had happened to his moron of a brother.

Turning, Dean pulled off his jacket and swung it over one shoulder while he walked down to the car. He grinned when he heard Gabriel's whistles behind him.

Leaning over at the open passenger side window, Dean found himself looking a rumpled, harried-looking businessman in a very expensive suit. The man was mumbling to himself about first gear. Dean smiled.

"Hey sugar, you lookin' for a date?" Dean said in what Gabe called his 'sex growl'.

The man looked over at him and Dean was pinned by what had to be the bluest eyes he'd ever seen. "No. I am trying to locate Beverly Hills. Can you provide me with directions?"

Dean grinned. "Sure thing, man ... for five bucks."

Castiel looked at the young man leaning into the car. He was struck by the green – or were they brown – eyes set in what Castiel had to admit was a very handsome face. Still, his demand for payment threw Castiel off-balance. "What? Ridiculous."

Dean shrugged. "Price just went up to ten."

Castiel's eyes narrowed. "You cannot charge me for directions."

"Wrong, bud. I can do whatever I want – I ain't lost." Dean said with a smirk. He stood and turned his back to the car, knowing his ass was level with the window. And Dean knew it was a fine lookin' ass in the jeans he had on.

Castiel regarded the young man's back pockets for a moment. He debated the wisdom of what he was about to do and decided that the risk was outweighed by the return.

"Fine. Alright ... you win, I lose. Would you have change for a twenty?"

Dean gave his best broad smile as he got into the car with a wave towards Gabe. "For twenty, I'll show you personal. I'll even show you where the stars live." He plucked the bill from Castiel's fingers and tucked it into his pocket.

Castiel sighed. "No thank you ... a kind gentleman digging in the trash told me the way to Sylvester Stallone's house."

"Great," Dean said. He glanced behind them and motioned forward. "Down the street, make a right."

Castiel fought the gear shift and somehow managed to get them moving without stalling the vehicle. Dean cleared his throat as he looked forward.

"Uh ... lights ... lights would be good here," Dean suggested. Castiel looked around and finally managed to find the switch.

Dean looked around the interior of the car. He was like a kid on Christmas morning. "This is an awesome car!"

Castiel shrugged. "It's a little ... temperamental."

"Yours?"

"No."

"Stolen?"

"Not precisely."

Dean rolled his eyes. Making conversation with this guy was like watching paint dry. He turned his attention back to the road and listening to the engine. Castiel cleared his throat.

"What is your name?"

Dean put on his best flirt gaze. "Whaddya want it to be?"

Castiel pursed his lips and gave Dean a pained look. Dean sighed. "Dean. My name is Dean." He smiled at Castiel's pleased look. "So, what hotel you stayin' at?"

"The Regent Beverly Wilshire, Dean," Castiel replied.

"Down the block, right at the corner." Dean directed. He tried not to hear the gears grinding ... again. He ran his hand over the dash. "Man ... this baby must corner like it's on rails."

"I don't understand that reference," Castiel said.

"Well ... come on, man! This is the new year model – it's got a turbocharged 5 liter V-8 from a Lexus IS F! This puppy can go from zero to 62 in 3.4 seconds!" Dean explained enthusiastically. He winced as Castiel shifted.

"You know about cars, Dean ... where did you learn this?" Castiel asked.

"Back home ... dad was into American heavy metal – Mustangs, Corvettes, you name it. Bought 'em cheap and fixed 'em up – I paid attention when he'd let me." Dean said. "So how is it you know so little about cars?"

"My first car was a limousine." Castiel said bluntly.

Dean's eyebrows went up. "Oh."

"So," Castiel said, fighting his way to the next gear. "Where is this heavy-metal home?"

Dean, who was sitting in the passenger seat with a pained grimace on his face, muttered, "Lawrence, Kansas – you know, man, I think you left your transmission back there! You're not shifting right."

"I have no idea how to shift correctly," Castiel complained. "Dean, have you ever driven a Lotus?"

Dean looked at Castiel as though he might have grown another head. "Uh, no."

Castiel nodded. "You are about to begin now."

"You're joking."

"No. You are on my coat and this is the only way I can get you off of it." Castiel said drily.

Dean blinked and then laughed. "Cute."

When Castiel had managed to pull the car over and park, Dean eagerly switched places with him. He settled in and adjusted the mirrors to his liking. Dean could feel the vibration from the powerful engine. He looked over at Castiel who was slipping on his seatbelt.

"Buckle up – you're about to get the ride of your life. I'm gonna show you what this baby can do! You ready?" Dean asked with a broad smile.

"I am ready."

"Alright, here we go!" Dean said as he pulled out from the curb. He shifted smoothly and Castiel was amazed to feel how swiftly the car traveled. He talked while he drove to ease some of the nervousness he was feeling. "This has pedals like a racecar ... kinda close together. It takes a little getting used to – usually it's easier if you have smaller feet but that doesn't really matter. Hey, did you know your foot is a big as your arm from your elbow to your wrist?" Dean held his arm out to Castiel who stared at it and then him in succession. "Just a little bit of trivia."

Trivia? What the hell is wrong with you, Winchester? Dean thought. He was never this nervous with a client. Even a nerd client like this one.

"Tell me, Dean," Castiel began as he straightened his coat. "What sort of money does a ... young man like yourself make? A ballpark figure."

"I can't take less than a hundred dollars."

"A hundred dollars a night?" Castiel asked with a considering expression.

"An hour."

Castiel blinked. "An hour? You make a hundred dollars an hour and your jeans are almost faded white and you wear work boots? You must be joking."

Dean frowned at the tone in Castiel's voice. "I don't joke about money."

"Neither do I, Dean." Castiel said quietly. "A hundred dollars an hour ... rather stiff."

Dean reached over and slid his hand between Castiel's legs. He grinned over at the man. "Nah, but it's got potential."

Castiel gave him another pained look. Dean sighed and retracted his hand. Nothing was going to happen with this one, it looked like.

Too bad, Dean thought. This one was at least good-lookin'.

Parking the car in front of the hotel, Dean got out and stood awkwardly beside the car. Castiel draped his coat over one arm and smiled.

"So ... here ya go," Dean said, pointing vaguely at the hotel.

"Yes. Thank you, Dean," Castiel paused. "Will you be alright?"

"Who me? Yeah, I'll just uh ... get a cab with my twenty." Dean replied. "See ya."

Damn. All the way back home with only a twenty to show. Fuckin' waste of a night. Dean thought, walking over to the bus stop. He sat on the bench and sighed, hands tucked in his jacket pockets.

Castiel regarded Dean from a distance. He'd never been attracted to a man before ... it was ... unsettling. Dean's eyes were so bright and when he talked about the car, his enthusiasm had been infectious. Castiel had started wanting to actually hear more. He certainly wasn't difficult to look at ... well-built and the faded jeans definitely did show off his backside to its best advantage. Castiel frowned and then made a decision. He walked over to Dean.

"No taxi?"

Dean smiled. "Nah ... I like the bus."

"Dean ... I was curious – did you really say a hundred dollars an hour?" Castiel asked lightly.

"Yeah, I did."

"Well, Dean ... if you don't have any prior engagements, I would be very pleased if you would accompany me into the hotel."

Dean's smile made Castiel's heart pound. "You got it!" He swung his legs off the bench and moved to walk beside Castiel with his usual strut. "So what's your name?"

"Castiel."

"Castiel? That's a mouthful," Dean said.

"My father was ... religious. I am named after the angel of Thursday." Castiel explained.

Dean's expression was priceless. "No kidding? I'm actually bein' picked up by an angel? Awesome." Dean bumped his shoulder against Castiel's companionably. "This is fate, Cas ... that's what this is."

Castiel blinked. Cas?

As they approached the door, Castiel unfolded his coat and began to place it across Dean's shoulders. Dean looked at him, confused.

"Um, what's up, Cas?"

"This establishment does not rent rooms by the hour, Dean. Your attire ..." Castiel flushed, not wanting to be overtly insulting.

Dean nodded. "Gotcha, Cas. No sweat." He pulled his arms into the beige overcoat and happened to glance upward. What he saw stopped him in his tracks. "Wow." He looked around and noticed that he was woefully and wrongly dressed for just the lobby of this hotel. The patrons looking at him made Dean feel as though a spotlight was landing directly on him and displaying every detail in sad relief.

"Dean," Castiel's deep voice sounded next to him. He took Dean's elbow and began to guide him toward the elevators. "You'll be fine, Dean. Stop fidgeting."

Dean was busy studying the pattern on the tile floor when they paused at the main desk. He wished Castiel would just hurry up and get them to the room. Dean couldn't stop the blush that crept into his face but when he reached the elevators with Castiel he noticed only one other couple there. An older couple who regarded him primly. Dean's defenses went into overdrive. The moment the elevator opened, he swaggered past the attendant and shouted.

"Well color me happy there's a sofa in here for two!" Dean said loudly.

Castiel looked at the couple. He sighed apologetically. "First time in an elevator." He explained.

The couple nodded and Castiel entered the elevator. The attendant, a young man, smiled to himself as Castiel looked at Dean with that pained expression Dean was beginning to hate.

"Sorry, Cas ... couldn't help it." Dean said with a laugh.

"Try," Castiel said. He smiled, though, so Dean didn't feel too badly.

The elevator stopped and the attendant announced, "Penthouse."

Dean blinked and looked at Castiel with raised eyebrows. "The penthouse?"

Castiel watched Dean walk to the door of the suite and he sighed.

What have I gotten myself into?