AN: Written for destielficletchallenge. Prompt: Person A is an undercover cop who is following Person B. (Doesn't matter if they're guilty or not.)
The guy was clearly struggling. The boxes he was carrying were way too big for him. Dean checked his watch. He still had half an hour before his meeting; he could skip getting a bagel to help the guy out.
"Need a hand?" He asked.
"Oh, god yes," the man replied. Dean took the largest box from the stack and could finally see the guy's face. He had dark hair and week-old scruff, as well as a pair of warm blue eyes. Dean realized he was staring and snapped out of it.
"Yeah, so, which floor are you on?" He hit the elevator button with his elbow and stepped inside, followed by the guy.
"Six." Dean managed to hit the button with his elbow without accidentally pressing any others. Score.
"My name's Dean, by the way. I'm on the third floor" The guy's eyes widened a bit, but maybe Dean was just imagining things.
"Nice to meet you. I'm Jimmy." The doors of the elevator slid open, and Dean followed Jimmy down the hall to his door. The apartment inside was full of boxes, all in various stages of being unpacked. "You can just put that down there, I can handle it from here."
"Awesome. Well, see you 'round Jimmy. Welcome to the building."
"Thanks." He shut the door. Once he was sure that Dean had gone away, he pulled out his phone and dialed.
"Hello?"
"Hey, Michael, it's Cas."
"Hey, Cas. How're you settling in?"
"Fine. I think I found him already." He could hear a low whistle on the other end.
"You sure?"
"Same name, same floor, matches the picture."
"Damn, Cas, you work fast."
"It was kind of an accident, to be honest."
"Whatever. You know what to do from here?"
"Yeah, yeah. Befriend the guy, get his trust, the whole nine."
"You sound like you've got this covered, Cas. I'll leave you to it."
"See you." He slid the phone back in his pocket, and went over to his computer, pulling up the file.
Dean Winchester. The picture matched, but the Dean he'd met didn't have a beard anymore. He looked nice clean-shaven, Cas mused to himself. Step one, find the guy. Check. Step two, get in close. That was where the finesse came in. Cas did love a challenge. He sighed, looking around at his empty apartment. No time like the present to unpack.
Cas (or 'Jimmy', as he constantly reminded himself) ran into Dean again that afternoon at the Starbucks down the block. He was standing there, waiting for his coffee when Dean walked in. He smiled when he saw Cas and gave a small wave. Cas grinned back. He grabbed his drink and sat down, intentionally facing away from Dean. He couldn't be too obvious. A few moments later, Dean slid into the seat across from him.
"Hey. It's Johnny, right?"
"Jimmy," Cas corrected. He was not about to slip up. "And you're Dean?"
"Yeah. Fancy seeing you here." He took a sip of his drink and Cas noticed that Dean had freckles. Huh. Those weren't in the picture. "How're you settling in so far?"
"Okay. I need to hit the grocery store, I've got nothing in my fridge."
"If you want, you can come to my place for dinner tonight. I've got a ton of food since I'm used to cooking for me and my mammoth brother, so it'd be no problem."
"Oh, you don't have to."
"I insist. Swing by at seven. You like pie?" Cas nodded.
"Alright, cool. Catch you later." Dean got up and left. Success. Cas actually did have to go to the grocery store, though. He finished off his coffee and headed out to the street.
Cas stared longingly at the razor. He'd grown out his stubble to obscure his face for the undercover work, but he didn't like it one bit. Maybe he could just trim it. "This is not a date," he reminded himself. "It's just two neighbors together for dinner." But he thought again about Dean's inviting face and damn broad shoulders. "Why does a drug lord have to be so sexy?"
He knocked on Dean's door at seven, sharp. He had changed into a clean pair of dark jeans and a white button down.
"Come on in, door's open." Cas stepped inside the apartment, shutting the door behind him. He followed the delicious smells to the kitchen where Dean was pulling a tray of potatoes out of the oven. "Perfect timing, Jimmy. Dinner'll be ready in-" he glanced at the timer on the microwave- "five minutes. Can I get you something to drink? A beer, maybe?"
"That'd be nice." Dean grabbed one out of the fridge and popped the top off for him. Cas took a sip. Damn, this drug lord had good taste. "It smells great in here."
"Thanks. I've been cooking since I was a kid. My dad was never really great at the whole parenting thing, y'know, so I kinda raised my brother by myself."
"Where's your brother now?"
"He used to live here, but he just got married. Her name's Jess, she's the sweetest. Right now they're on their honeymoon." Cas nodded. "You got any siblings?"
"No."
"Any family at all?"
"Not really. I have an uncle, but he's not that close." This was all true. In order to go undercover, you had to drop all your ties. And who better than Cas, who didn't have any to begin with?
Dinner tasted just as good as it smelled, maybe even better. Cas was so stuffed that he barely had room for the gorgeous apple pie at dessert. When he finally left for the night, he felt several pounds heavier.
Somehow or another, Cas ended up at Dean's every night that week. Dean always invited him: once while stopping by to offer a slice of leftover pie, twice when they ran into each other at Starbucks again, and the final time Dean called Cas's cell.
"How did you even get my number?"
"I'm a sneaky bastard, and you don't have a passcode." Cas mock-scowled into the phone, but in reality he was smiling.
"Point taken. Is there a reason you're calling?"
"You probably already know why. Seven, okay?"
"Could I ever say no to your cooking?"
"Probably not. See ya."
Cas was excited. Being with Dean was like all the best parts of being drunk. The atmosphere was warm and soft and so damn pleasant. Cas whacked himself in the head with his palm. "No. You are not falling for him. You know he's a criminal!" But it was still hard to save face the minute Dean opened the door to let Cas into the apartment. Dean stared at him for a moment.
"You look nice."
"So do you." They stood there for a moment.
"Ah, screw it." Dean reached out and firmly kissed Cas. After the initial shock, Cas found himself kissing back.
"What about dinner?"
"Screw Dinner."
That's when Cas sort of lost track. Somehow he ended up on the couch, lips locked with Dean's, and then the couch turned into the bedroom, and then Cas ended up having the best sex he'd had in years. He then promptly zonked out for the night.
It wasn't until he woke up the next morning in Dean's bed that he put it all together.
"Oh, shit." Dean was pulling on a t-shirt, and he looked over and smiled at Cas.
"Morning, beautiful."
"Shit." Cas said again. It wasn't that he wasn't gay or anything. His boyfriend in college confirmed that. It's just that this wasn't supposed to happen. He wasn't supposed to have sex with the drug lord he was following. He wasn't supposed to appreciate the curve of his torso as he stretched the fabric over his skin. He wasn't supposed to stare at those green eyes.
"What's wrong, Cas? Don't like what you see?" Did he just call him Cas? Dean laughed at his surprised expression. "The jig's up. I'm one hell of a detective."
"But…how?" Dean plopped down on the bed next to him.
"First of all, I never told you which apartment was mine." Cas mentally smacked himself in the head. "That meant you were either really good at guessing, or knew something about me. Second, your apartment has literally no personal items. That's fishy. Third, I found this in your wallet." He held up a folded note.
"Wait, my wallet? Were you trying to rob me?" Dean chuckled.
"No, but like I said, you knew something about me. I had to see what. Your fake stuff's really great and all, but if you've got a letter from your supervisor, it kinda blows your cover."
"He's dead." Cas said abruptly.
"Huh?"
"The supervisor that gave me this. Dead. It was the last thing I ever got from him. Figures it would be all about you."
"By the way, before you ask: no. I'm not a drug lord."
"Then why does every source say you are?" Dean sighed and leaned back against the headboard.
"My dad. He's the one who's in the business. He tried to get me in too, but I said no. I didn't have anywhere to go, so I ended up staying with him anyway. But the damn guy hit us all the time, always drunk. My brother was real smart, skipped out to become a lawyer, but I wasn't so lucky. Last thing my old man did before he disappeared was ask for a favor: he'd skip out, I'd be a plant."
Dean looked down at his hands. "I don't know why I ever said yes to that bastard," he choked out. Cas could see his eyes getting misty. Without a word, he put his hands over Dean's. Dean looked up at him, the hugged him hard. "Thanks, Cas," he whispered. Cas simply squeezed harder in reply.
"I'm glad you're not a drug lord," he said quietly. Then Dean started laughing. It got bigger and bigger until he had tears rolling down his cheeks. When he finally settled down, he looked at Cas.
"So, I know you've gotta protect the law or something, but what if we just skip out? You and me? I'm pretty good at disappearing."
"What? Why me? We've only just met." Dean shrugged.
"I dunno. Does there have to be a reason? You're nice, you're funny, you're a great lay," Cas blushed. "-you're also pretty easy on the eyes. If I can manage to find someone who's all of that, why wouldn't I want to be with them?"
Dean put his hands in Cas's. "The way I see it, the universe has dealt me a lot of shit. You too, no doubt, since you're doing fucking undercover work. But if a good thing, you, rises from all that shit, then I'd be an idiot not to take a chance." Cas nodded. "Worst-case scenario, it doesn't work out and we go our separate ways. You already know I'm no drug lord, so you've got nothing to lose. What d'ya say?"
"Alright."
"Alright? You mean it, Cas?"
Cas didn't say anything; he just leaned over and planted a kiss on Dean's lips.
"Come on then," he said standing up. "Breakfast isn't going to make itself. You owe me from no dinner last night."
Michael never really found out what happened to Cas. Sometimes he'd be walking down the street and swear he heard his voice. Some days he's look up and see Cas's face, but then he'd blink and it would be gone. He must've been going crazy.