A/N: Managed to get another character in there. It's tough sometimes. Hate to be lame, but the chapter AFTER this is 90% likely to have more people/action. Ah well. Thanks for reading.
The three men had effectively abandoned their vigil around 5 AM, when a spastic kick on the back of his seat awoke Dean and he found that they had all passed out and left the guarding of Sam to the angels. He felt a surge of guilt as his eyes darted around the neighborhood. Everything seemed to be in order. It was just before sunrise, but looked more like twilight, the street lamps glowing orange through the otherwise bluish haze. Dean's sleep-addled mind wandered around trying to remember what exactly the color of the horizon was reminding him of. His eyes settled on Castiel's eyelids, and they opened with a start as if they could feel his gaze. Dean almost jumped, realizing that he had two drops of sunrise staring him down from only a couple feet away.
"Hello, Dean."
"Sleeping on the job?" He tried to look stern.
"Gabriel relieved me." He answered, defensively.
A little whistle from behind them made gave them both a start. Gabriel was sitting up straight, his eyes bright, with no pillow or blanket to be seen, which baffled Dean who had checked only moments earlier to find his eyes twitching under their lids. Gabriel's eyes were now trained on something, and he reached forward and grabbed their shoulders. They followed his gaze to see a long black Mercedes creeping down the road in front of Sam's house. They all three instinctively ducked as the car crawled past them, headlights suspiciously unlit.
Dean whipped around in his seat to watch as the car trundled away, trying to get a glimpse of the the two hatted figures in the front seat. It was a fruitless endeavor, and he sat back with a huff.
"Well that was odd." Castiel offered, in a gravely morning tone.
Sam awoke with a start as he heard his front door open quietly, then click shut.
"Dean?"
"Yeah, Sammy. It's me."
Sam sighed with relief, then stiffened again.
"What's wrong? What time is it? Are you alone?"
Dean inched into Sam's bedroom and smiled at the fact that his sasquatch of a brother was destined for a lifetime of ill-fitting pajamas.
"Yeah we kind of staked you out last night. I just sent Cas and Gabe home to get cleaned up. They're gonna meet us at the store at 9:00 AM. You have meetings all day, right?"
Sam rubbed his face in confusion.
"Don't they live on the other side of town?"
Dean jaw twitched and his eyes darted to the window.
"I sent them home with the Chevy."
Sam's jaw hit the floor.
"You let Castiel drive your car?"
"Yeah. Did we need it? Is something wrong with yours?"
"Um no. Something's wrong with my brother. You're letting a guy you just met drive around in your most prized possession without you. You do realize that you've actually told me not to look at your car before, right? And now there's some stranger in there molesting her and you're okay with that?"
"The man was in a war, for God's sake! He knows how to drive." Dean responded, choppily. "And you're my wealthy, successful little brother! I don't have much to lord over you. If I have to use my car, so be it."
Sam chuckled and shook his head. He swung his legs over the side of the bed, his long locks tickling his eyes. He stood and stretched and embarked on his morning routine, brushing his teeth and slicking his hair back carefully with a fancy pomade. He could hear Dean pacing around the house aimlessly, examining the trinkets and photos that Sam had collected now that he was on his own. Sam heard him sigh.
Finally he emerged, freshly suited and ready for a day of grueling shareholder meetings that he had absolutely no interest in, but was unfortunately competent enough to attend. After that he was going to be introduced to the men who were going to potentially buy his shares in the store. His chest knotted a little bit as he thought of the great things he was going to do once he was out of the department store business forever.
Dean was examining a postcard from Kansas when he noticed Sam standing in the doorway, ready to leave. He set the card down and gave him a grin.
"Ready to shake a leg, Samson?"
Sam rolled his eyes. Dean held him back when they reached the door together.
"Bodyguard first," Dean insisted, and led the way, scanning the street for the black Mercedes or anything else that might seem out of place. Sam locked the door and they walked over to his car.
"And Sam?"
"Yes, Dean?"
"When I get my baby back later today, if you so much as look at her funny, I will fight you."
Cas and Gabe miraculously arrived at Winchester's before Sam and Dean. The store hadn't opened yet, so they loitered outside, watching businessmen clutch their briefcases and rush to their prospective offices. Gabriel made sure to eye each one as if they were a potential threat, though they all looked nearly identical in their grey or tan overcoats and fedoras. Consequently, Gabriel was doing quite a lot of suspicious squinting.
"It's a pity the criminals don't dress in a manner different from the general populace that would make them easier to identify." Castiel stated.
Gabriel turned and gave him an earnest nod. Castiel just chuckled and chewed on a toothpick, absently.
"Hey, you two! What's the big idea?" The gruff voice of Crowley pierced through the hum of the crowd. He cut through the sidewalk traffic, and stomped up to the detectives.
"Hello, again Mr. Crowley. What a pleasant surprise. Just so you know, we're first in line for the big humidor sale. You'll have to get behind us." Castiel spoke evenly and gave Crowley a small smirk.
Crowley fumed, pulling his hat off to reveal that his head was literally hot with rage.
"Now you listen to me! I don't know what you're on about, but I'll not have you loitering in front of my store like beggars."
Gabriel dropped a dollar into Crowley's upside-down-hat, then pointed at Crowley accusingly. Crowley tipped his hat over and dumped the dollar out in disgust. He lunged towards Gabriel, but Gabriel had already zipped behind Castiel, who stood his ground calmly. This flustered Crowley, who hadn't been exactly sure what he was going to do once he got his hands on the nimble mute.
"Have we met?" Castiel reached out his hand and plastered a fake smile on his face. "I'm Castiel Bourbon, a seller of fine liquor. Or you could lick him with no ballyhoo from us. I'm utterly indifferent." Castiel shook Crowley's hand as Crowley shook with rage.
Gabriel pulled a pansy from his pocket and danced by Crowley, stringing the flower behind his ear.
Sam and Dean pulled to the curb with a rumble and immediately noticed Crowley looking a bit like he was going to explode. There was inexplicably a flower behind his ear and a dollar at his feet.
"Is everything alright here, Mr. Crowley?" Sam asked cautiously, knowing his brother hated the man and wouldn't initiate contact unless forced.
Crowley flicked the flower out of his hair and turned to Sam sharply.
"Fine, Mr. Winchester. I was just getting ready to call security." His demeanor morphed into the sickly smooth calm of a manipulative bastard.
"Call security on who?" Asked Sam, genuinely.
"On these charming fellows right here." Crowley nodded his head towards Castiel and Gabriel.
"But sir, these are my bodyguards. That's Detective Flywheel and his assistant Gabriel.
Dean grimaced. He hadn't wanted anyone to let on to Crowley that they were watching Sam. He just didn't feel like he could trust the guy. Castiel had seemed to understand this implicitly, but now Sammy had gone and blown their cover.
"Bodyguards? I see."
No one liked the croak in Crowley's voice, or the way his eyes darted and weaved along the ground in a calculating manner.
"Well then. Perhaps it was all misunderstanding." He turned back to face Cas and Gabe. "I apologize for the miscommunication. You are welcomed to the store when Sam is on the premises." Crowley turned on his heel and entered the building without giving anyone time for a response.
"Well that felt weird." Dean and Cas exchanged an ominous glance that they were planning to share with Sam until he was distracted by Jess approaching the store to punch-in for her morning shift.
When Sam made it to the executive offices he was immediately woman-handled into the boardroom by his temporary, but efficient secretary, Becky. Castiel and Dean followed, reluctantly until Becky whipped around and addressed them in a shrill voice.
"I'm sorry, where do you think you're going?" She was slight, and her long hair was knotted fashionably at the top of her head.
"I'm Castiel Flywheel, Sam's bodyguard." Castiel stood awkwardly for a moment, waiting to see if Becky would offer her hand for shaking. He cocked his head as he watched a flood of joy and relief flood her face and change her expression from completely collected to certifiably crazy in the course of one short second.
"Oh that's wonderful! I like to keep an eye on him, but I can't be everywhere. And ever since he got the plans for the conservatory he's been meeting with all manner of people and it's difficult to vet every single one of them, though I've cleared most everyone he's met with one-on-one. But with his performance at Chez Paree coming up I've been even busier because all those night-club people end up looking so seedy and every man could have a gun stashed pretty much anywhere, whereas I have to keep mine in my purse but then again the night club people just seem to like music and -."
Castiel reached out and grasped Becky's shoulders as gently as possible in an attempt to somehow slow the rate at which she was delivering information. Dean stepped in closer, entranced by the seemingly innocuous secretary and her vast knowledge of Sam.
"You've been watching Sam?" Dean asked.
"Uh. Well. I mean. I've been keeping an eye on him. Someone has to. He's going to be super famous, you know!" Becky looked from Dean to Cas, her eyes questioning whether they understood how imperative her mission was.
"And you have a gun in your purse?" Castiel narrowed his eyes at her, not letting that little detail slip by.
Gabriel popped up beside them with her purse, twirling a little two-shot pistol around his finger. He whistled a greeting.
"My gun!" Becky screeched. Castiel pulled her forward while Dean tried to cover her scream. The three of them were now nestled together in a startled knot.
"Shhhhh!" Dean chided.
Gabriel put the gun in the purse and placed it on Becky's desk with a guilty look. He backed up into a plush armchair and curled his knees up under his chin. Meanwhile the Becky sandwich had yet to move.
"Okay." Dean cleared his throat. "On the count of three we're all going to let go. Becky is not going to scream, and Gabriel isn't going to touch anything else that doesn't belong to him."
Gabriel put his hat over his face in shame. Dean counted to three and released Becky's mouth, wiping his noticeably moist hand on his pants. Castiel extended Becky an arm's length away then finally lifted his hands gingerly from her shoulders. Gabriel slid out of his chair, slunk up to her and returned her purse, which she gripped tightly.
Dean chewed his lip. Castiel gave Becky an appraising look. Gabriel gave her a daffodil, which seemed to win her over.
"Okay, Becky. We're going to leave you in charge of guarding Sam when he's in these offices."
Becky's eyes glowed and she looked like she might suddenly float away. Castiel grimaced momentarily, but seemed to resign himself to the idea. He stepped forward to speak in a lower tone.
"You also have to keep an eye on Crowley. I don't trust him."
"Sheesh. You don't have to tell me twice. That guy's a slimeball, and all the worst looking characters are always coming to see him."
Cas checked Dean with a glance that seemed to ask if leaving Sam alone with only a Becky to fend for him against Crowley was a wise plan. Dean mouth-twitched back a solemn grin which seemed to remind Cas that there were a lot of other people in the offices, and it was an unlikely place for a showdown. Cas nodded. Gabriel rolled his eyes and crossed his arms over his chest, looking very dramatically neglected.
"Wow. You guys make a great pair- uh- team." Becky couldn't translate the eye conversation that had just flown by her, but that didn't mean it didn't completely turn her on. Gabriel huffed. "Threesome," Becky spouted apologetically. "A great threesome." She laughed, nervously.
Dean shook his head and brushed his hands on his suit. Cas watched him out of the corner of his eye.
"Alright, boys. Let's go. If you need us, we'll be in the bed department."
He ushered Castiel and Gabriel out of the executive lobby and back over to the elevators.
"The bed department?" Castiel asked, quizzically.
Dean and Gabriel turned and gave him identical looks of disdain.
"What, you're not tired?"