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Title: Structured Clutter
Pairing: Dean/Castiel
Fandom: Supernatural
Rating: NC-17/Adult/Explicit
Word Count: 18k
Alternate Link: AO3

Full List of Kinks and/or Warnings: AU, master/slave, master!Castiel, slave!Dean, consent issues, spanking/domestic discipline, paddling, caning, bondage, blowjob, asexual!Castiel, aromantic!Dean, aromantic!Castiel

Setting: Master/Slave AU

Summary: Dean doesn't know what to expect when Master Chuck, the loving owner he and other family members had grown up with, transfers ownership of him to Castiel Novak, the black sheep of the family who doesn't want a slave, who doesn't know what to do with one, and who never asked for this.







Part 1

Dean squared his shoulders and confidently stepped out of the limo. Mr. Novak would be waiting for him, and he had no idea what to expect, but he sure as hell wasn't going to go in there with his tail between his legs.

The Novak family was known for being kind to their slaves. They bucked tradition, had for decades, and no one knew it better than Dean, who had been born at Master Chuck Novak's estate.

Dean had come of age in the home, but Chuck still hadn't sold him. He never would've because that's just the way the Novaks were. They treated everyone like family.

His parents had been taken care of, even after John had died years ago. Dean had been raised along with Chuck's children, eating the same food, learning from the same tutors, though when they'd all been released after school, Dean performed his duties instead of running off with the rest of the kids.

Even then, it hadn't been all work and no play. He'd been to parties, he was allowed to play with the kids when he'd finished his chores, and Dean had been happy. He'd been free to drive Chuck's vehicles, go into the city to run errands, and he even accompanied Chuck and his wife a few times when they'd gone out of the country.

But he didn't know what to expect of his new master. The Novak name was all well and good, but Dean wasn't naive. He knew there were traditionalists out there who, while not being cruel, wouldn't tolerate most of the freedoms Dean had enjoyed. And if Mr. Novak was cruel, well, Dean knew his life would be getting hard sooner rather than later.

He'd chosen his nicest pair of dark slacks and paired them with a dark green button down shirt. He wanted to look nice for his new master.

As far as he knew, Mr. Novak had never owned a slave before, at least that's what Chuck had told him. And when Dean had asked why he was being given to Mr. Novak, Chuck had said it was for Castiel's own good, whatever that meant.

"Follow me," Hannah said as she walked in through the front door of a rather modern-looking mansion.

Dean followed closely as she took him up the stairs and down a long hallway. She didn't bother knocking when she opened the door to what turned out to be Castiel's office.

"Hannah," Castiel said, smiling as he grabbed his briefcase and headed for her, arms out at his sides.

"Hey," she said as she gave him a hug, then stood back and turned to Dean. "This is Dean Winchester."

"Hi, Mr. Novak," Dean said, hands behind his back and standing just inside the door. If Castiel was more of a traditionalist, he wouldn't want his new slave to shake his hand, so Dean took the more cautious route.

Castiel sighed. "Hannah," he said as he turned to pout at her, "I told him I didn't want a slave."

Dean tried not to react, but Hannah was having none of it.

"Castiel!" she chided. "The paperwork is already done, his things are being sent, and he's standing right there."

Castiel grimaced as he looked Dean over. "I don't know what to do with him."

Hannah shook her head. "I'm sure you'll figure it out," she said, then walked out, throwing a sympathetic smile at Dean.

Castiel huffed. "I don't know what to do with you."

Dean didn't really know what to say, and he didn't know Castiel well enough to gauge whether he should just come right out and make suggestions. Chuck had thoroughly spoiled him.

Castiel looked down at his watch. "I'm late," he said, lifting his briefcase as if that would explain it all. "I-I've gotta go."

Dean rolled his eyes after Castiel left the room. "Well, that could've gone worse, I guess," he muttered.

*

Dean figured out fairly quickly why Chuck had insisted Castiel take on a slave. His bookkeeping was a mess, his office was a mess, his organizational skills were lacking from the depths of his closets to his filing cabinets and even his refrigerator.

He stopped organizing things around four o'clock so he could make dinner, but it boggled his mind as to why Castiel hadn't hired a few workers even if he hadn't wanted a slave. He'd managed to clean up Castiel's office a bit, had reorganized the master closet, and had cleaned out the refrigerator, but he still had quite a lot to do. It could all wait for another day.

Dean heard the front door open about quarter after six and adjusted Castiel's schedule in his own head. He'd prepared a meal that could easily simmer for a while if Castiel wasn't home by half past five when most people arrived home from office buildings. At least until Dean could figure out some type of schedule.

"Oh," Castiel said as he stood in the archway to the kitchen, eyes wide. "You're still here."

"Dinner's ready, sir," Dean said as he pulled a plate from the cupboard. "Would you like to eat at the table or someplace else?"

"Oh, um," Castiel said, frowning. "My office. I'll eat there."

Dean nodded. "I can bring it up to you if you'd like."

Castiel paused for a moment, then nodded. "Yes, do that," he said, then turned on his heel and walked out.

Dean smirked as he dished up the food and grabbed some silverware. Castiel was an odd guy so far, but he seemed harmless. Dean knew that could change at any moment, but it was a relief to see things weren't going to be doom and gloom at the very least.

As he made his way to the office, he heard a crashing sound. He moved faster, hoping Castiel was okay, but as he walked into the office, he froze, plate in his left hand and bottle of water in the right.

"What have you done?" Castiel yelled as he kicked a filing cabinet drawer closed. Castiel's face was red, he was panting, and his tie was crooked.

"I organized the office, sir," Dean said, only just then realizing it hadn't been a good idea.

Castiel sputtered for a moment, then threw his hands up in the air. "Why would you do that?" he asked, a mix of furious and perplexed.

"I... It looked like, um," Dean started, but couldn't really come up with a tactful way of saying the room had looked like a pigsty. "It looked as if the office needed some organizing."

"Organizing?" Castiel yelled, then he picked up his discarded briefcase and dropped it onto the desk. "I had everything right where I wanted it," he said as he opened the briefcase and started pulling out files. "I knew right where everything was. Now I'm going to have to find everything I need by tomorrow morning and hope that I still have time to get it all together in time."

Dean felt like shit. He'd only been trying to help, but he'd made the world's worst first impression on his new master. "I'm sorry, sir. Would you like me to help?" he asked, shifting from foot to foot.

"No," Castiel said, already rummaging through the filing cabinets for his papers. "You've done more than enough. Just go to your quarters or something."

"Would you like me to leave your dinner here?" Dean asked.

Castiel looked up at him, bewildered expression on his face, as if he couldn't begin to understand why Dean was asking him that. "Just leave it on the floor," he said, waving him off.

"Yes, sir," Dean said as he set the plate and water bottle down by the door. "I'm sorry."

Dean stood there for a moment, but Castiel was too focused on his filing cabinets, so he turned around and left. He wanted to go to the kitchen and clean up, but Castiel had told him to go to his quarters. He figured he'd done enough damage for one day, so he did as he was told.

*

Dean wasn't sure what Mr. Novak would ask him to do for the day, but he got up and showered the next morning and put on some casual clothes. Castiel hadn't even looked at his clothes the day before, so he probably wasn't one who cared for such things. A soft pair of sweats and a grey Henley would do until he heard different.

He started making breakfast a little after seven in the morning, politely ignoring the fact that Castiel was already in his office, or perhaps he had never left it. He assumed Castiel liked coffee, since there was a coffee maker on the kitchen counter, so he filled a plate with eggs, sausage, and toast, then topped off a mug of coffee before starting up the stairs.

Castiel was standing at the desk, his back to Dean. "Sir?" Dean said, hoping he wasn't going to startle the man.

"Hmm?" Castiel said, then turned around, frowning. Was he ever happy?

"Would you like to eat your breakfast here in the office?" Dean asked.

"Um, oh," Castiel said, looking around the room as if someone nonexistent was going to answer the question for him. "Just set it on the desk," he said, waving at the mess of papers and books covering his desk.

Dean grimaced as he approached, grateful that Castiel was too interested in his papers to notice the sour expression. "Sir?" Dean said when he couldn't find an inch of open space on the desk.

"Oh," Castiel said, then pointed to the shelving unit to his right. "Just put it there."

Dean waited until he was standing at the shelving unit before he rolled his eyes. "Is there anything you'd like me to do for you today, sir?"

Castiel looked up at him as if he'd forgotten Dean was in the room. "Oh, well, um. Yes. I'm going to the office downtown today," he said as he shuffled his papers around, "so I've arranged for you to spend your time at the daycare."

Dean flinched without meaning to, but he forced himself to remain calm and nodded even though Castiel didn't see him. "Yes, sir," he said, working very hard to keep the disappointment and fear out of his voice.

"Hannah brought a change of clothes for you," Castiel said, eyes glued to the book he was scanning. "She tells me they're required, so make sure you're changed and ready to go in twenty minutes."

Dean shivered. "Yes, sir. Um, sir?"

"Yeah?" Castiel said, not bothering to put his book down.

"I'm really sorry about rearranging your office," Dean said. "I didn't realize you had everything right where you wanted it. I was just-."

"Yes, yes," Castiel said, waving him off. "You were doing your job."

Dean opened his mouth to say more, but he stopped himself. He knew better than to question his master. If Castiel saw fit to punish him, then he deserved it. And even if Dean had only been doing his job by cleaning up the house, he really should've waited for instructions from Castiel instead of taking the initiative. He'd gotten so used to Chuck and how easy it was to work for the man. It was going to take some time to get used to Castiel.

*

The ride downtown was quiet. Castiel was reviewing a stack of papers, so Dean stayed still and didn't say anything. His leg bounced a few times because he was nervous, but he forced himself to relax. He'd never been sent to daycare before.

Chuck had never even threatened anyone in his house with daycare that Dean could remember. The only reason he knew what went on there was from second and third-hand reports and whispers. If a slave fucked up and the master was too busy to discipline them, a slave was sent to daycare for correction.

Dean could handle it. He'd fucked up. He knew he deserved it. But that didn't mean he wasn't scared. He'd heard horror stories.

The Novak family was known for their kindness, though, so maybe Castiel's daycare wasn't like that. It was located in the same building, so it would be difficult to abuse slaves and still uphold the family name.

He played with the cuff of the white long-sleeved shirt he'd been given to wear. It was light cotton to match the pants, free flowing and something Dean would never have chosen for himself. The boots were an odd contrast, but Hannah hadn't left any shoes along with the clothing, so he'd worn his own. Chuck had gotten them for him.

Dean exited the vehicle after Cas, keeping his head held high. His parents and Chuck had raised him right, and they'd all told him time and time again that a cowering slave was obviously an untrained and disobedient slave who was only pretending to be a good slave. They told him he should be proud of what he was, take pride in his work, and never be afraid to speak up for himself, at least around the house.

"The daycare is through those doors," Castiel said as he headed toward the bank of elevators.

"Yes, sir," Dean said, walking to the daycare.

His confidence faltered the moment he walked through the doors. There was a front reception area with a secretary, and Dean made his way to her.

"I'm Castiel Novak's," Dean said. "He sent me here for the day while he's working."

"Name?" the woman said, uninterested in him.

"Dean Winchester," he said, playing with the cuff of his long-sleeved shirt.

"Wait there," the woman said, then picked up the phone by her left hand. "Ellen, I've got an unscheduled slave here, but he says he's Mr. Novak's slave. Okay, thank you, ma'am."

Dean tried to keep still and not fidget while the secretary went back to filing her nails, ignoring him as if he wasn't even there.

"Dean," a woman said from a doorway to his right.

Dean turned. "Yes, ma'am?"

"Come this way," she said, then turned and headed off down the hallway, as if she had no doubt he would follow.

Dean hurried to catch up with her, then fell into step behind her. It seemed odd to him that she was wearing jeans and a comfortable-looking button-down shirt, boots much like his own. He'd expected something more professional, but he didn't dare mention it.

She opened the door to a room about halfway down the hallway and went in. Dean followed her, then came to a stop when he saw where he was.

The floors were stained and coated cement, an off white color that was obviously easy to clean. There were eye-hooks on the walls and in the ceiling along with a St. Andrew's cross to his right, a padded bench to his left, and a wall of cabinets and countertops directly in front of him. He didn't want to know what was in the cabinets, but he had a feeling he was going to find out.

"Strip," the woman said. "A slave earns his clothes."

"Yes, ma'am," Dean said, immediately doing as he was told. His hands were shaking, making it difficult to get the buttons undone on his shirt.

"My name is Ellen," she said as she walked to the cabinets and unlocked the first one. "You'll call me ma'am while we're in the daycare."

"Yes, ma'am," Dean said, his voice cracking. He tried to control his breathing, but he was having trouble with it.

He set his boots to the side, then folded his clothes and set them next to the boots. When he stood up, Ellen was standing by the padded bench with a paddle in her left hand.

Dean didn't bother waiting for her to give him the orders, he just walked up to the bench and started climbing on, figuring if he waited he might lose his nerve.

"Hold up there, sweetheart," Ellen said, wrapping her fingers around his left wrist.

Dean stepped back away from the bench and looked at her, eyes wide. "Sorry," he said, wincing.

"I'm not gonna use this on you if I don't know what you did," she said, waving the paddle back and forth.

Dean fought the urge to run and instead nodded at Ellen. "Yes, ma'am. I was left alone at Mr. Novak's home yesterday, and he didn't leave me with any instructions, so I organized his office and closet."

Ellen's lips twitched, as if she really wanted to chuckle, but had much better control than to just let out some laughter. "Is that everything?" she asked.

Dean grimaced. "He doesn't know I cleaned out the refrigerator too. He was mad enough about the office that he sent me to my room before I could tell him."

Ellen nodded. "From what I read in your file, you've never been reprimanded at a daycare before."

"No, ma'am," Dean said.

"Okay, well, to put your mind at ease," Ellen said, patting his arm, "I'll tell you what's going to happen. The room can be a little intimidating even for anybody who's been to a daycare before. We do offer sexual training, but that's a specialized service, and Mr. Novak hasn't requested it. So today we'll just be going over basics after we get your punishment out of the way. Nothing fancy. It'll just be all the shit I'm sure you already know."

"Thank you, ma'am," Dean said, feeling a little relieved.

"Have you ever been disciplined before?" she asked.

Dean blushed. "My mom and dad both had me over their knee at times over the years, and Chuck -- I mean Master Novak did the same. Oh, and the cook, Bobby, he got me a few times."

"Ever been paddled?" she asked.

"No, ma'am," Dean said. "Bobby used a wooden spoon on me a few times, but everyone else used their hand or a belt on me."

"Can you stay still for me or do I need to tie you down?" she asked.

Dean opened his mouth, but nothing came out. He really didn't want to be tied down, but he wasn't sure he could stay still. "I don't know, ma'am. I'd rather not be tied down, but every time I've been disciplined, it was over someone's knee and they held me, so I just don't know if I can stay still."

Ellen gave him a small smile. "Thank you for being honest," she said. "Here's what we're gonna do. I'm gonna have you get on the bench, I'll give you a warm up, and at any time, if you feel like you can't stay still for me, say something."

"Thank you," Dean said, so relieved he wanted to hug the woman.

"Okay, then get on the bench," she said, gesturing to the bench with the paddle.

Dean was still shaky as he climbed on, but he settled down, his knees spread fairly wide and his chest down on the padded top. He took hold of the handles and tried to relax.

"I'm going to start with my hand, then I'm going to use the paddle," Ellen said.

"Yes, ma'am," Dean said, closing his eyes.

Dean sucked in a breath as she laid down the first smack. She was stronger than she looked, and it began to sting pretty quickly. He forced himself to stay calm, stay still. He squirmed a bit, her hand working up a good burn.

"We're gonna start with the paddle now," Ellen warned, then gave him a good smack.

"Ah!" Dean yelped, his chest coming off the top of the bench.

"Settle down," Ellen said, a hand on his back pushing him down again.

"Sorry, ma'am," Dean said, leaning down.

"You come up like that again and I'll tie you down," she warned.

"Yes, ma'am," Dean said.

Three more smacks with the paddle and Dean was panting through clenched teeth. He tried to spread his legs a little to ease the pain, but it did nothing.

The next time the paddle landed, he let out a whimper. It felt so much different than when he'd been punished at Chuck's house. This was so impersonal. Before today he would've thought that it would make the whole thing easier, but it made it worse. He was scared and felt alone. Ellen was only doing her job and didn't give a shit about him. And he hadn't even meant to get in trouble. He thought he'd been doing his job, something he never would've been punished for at Chuck's house. In fact Chuck would've thanked him and given him a hug.

Dean's chest ached, his eyes burning as he felt a strong sense of homesickness. He'd never go back to Chuck's. This was his new home. And if he didn't learn soon, he'd be in here every day.

"Ow," Dean moaned, clenching his teeth and trying to stay still. "Please, ma'am, I'm sorry!"

"I know you are," Ellen said, the paddle still coming down on his naked ass.

He let out a sob, his vision blurring as tears welled up in his eyes. "Please, I d-don't think I can stay still!"

"You've got seven more to go," Ellen said. "You can stay still for seven more."

"Ah!" Dean cried out, flinching away from the pain.

"Dean," Ellen said, voice firm.

Dean turned his head so he could look at her. It was an awkward position, but he knew she wanted his attention. "Yes, ma'am?"

"You have six more to go," she said. "I know you can stay still. Cry out, wriggle around a bit, that's okay. But you're going to stay in position for me."

Dean nodded. "Yes, ma'am," he said, panting.

"Good boy," Ellen said.

Dean pushed his face into the padded bench and squeezed his eyes closed. He had to stay in position. The smacks from the paddle landed so fast that Dean let out one long scream of agony, tears running down his face as he lost his breath with the remaining smack.

He cried into the bench, his body tense and shivering with pain and humiliation. He flinched when he felt her hand on his back, but then he leaned into the touch, taking the comfort she was offering.

Once his breathing calmed to occasional hiccups, Ellen patted his back. "I want you to slowly stand up. Go slow or you'll land on your ass."

"Yes, ma'am," Dean said, going slowly and letting her guide him up.

She already had a damp rag ready and washed his face, gentle swipes that reminded him of when his mother had done the same thing.

"You did very well, sweetheart," Ellen said. "Now I want you to go put your nose in the corner."

"Yes, ma'am," Dean said, sniffling as he made his way to the corner.

"I'm going to wash up a bit here, then we'll continue," she said.

Dean cringed, resting his forehead against the wall. She'd told him he was getting punishment, and he really hoped the paddling was it. If there was more to come, the day was going to be really fucking long.

*

"C'mon over here, sweetheart," Ellen said.

Dean turned around and walked to the center of the room, where Ellen was standing.

"Normally what I'd do with you is run you through some exercises to see if you know your way around a house," she said. "But you grew up in Chuck's house, you've been around the Novaks your entire life, and I think you know what you're doing."

"There's always more to learn, ma'am," Dean said humbly.

Ellen smirked at him. "You don't have to sweet talk me in here. Be respectful, but don't blow smoke up my ass."

Dean chuckled. "Yes, ma'am."

"Now Castiel," Ellen said, drawing out Castiel's name as if he was a conundrum. Which he probably was. "He's different than the other boys. You know he comes from a big family, right?"

"I know there's at least three brothers," Dean said.

"Three brothers, two sisters, and more aunts, uncles, cousins, and kin than you'd care to meet," Ellen said, shaking her head. "He's the baby of the family, and as such he's a little more spoiled than the rest of them."

Dean frowned a bit. He didn't know much about Castiel, but spoiled just didn't fit what he'd seen so far.

"Now let me finish," Ellen said with a grin. "He may be spoiled, but that boy doesn't know it, has never acted like it, and is totally oblivious to the fact that his brothers and sisters would do anything for him."

"He works really hard. Doesn't he?" Dean asked, but it was more of a statement.

Ellen nodded. "He's a very hard worker. He doesn't like handouts, wants to do everything himself, and tends to get lost in his own little world."

"Yeah, I noticed the getting lost thing," Dean said with a smile.

"Cas is a brilliant man," Ellen said. "When it comes to business, technology, the sciences, he's a genius. But put him any kind of social situation or ask him to make a run to the grocery store and he's lost."

"Oh," Dean said, eyes wide.

"Yeah," Ellen said, nodding. "I love the guy, but he can be hard to get along with. Unfortunately for you, there's a steep learning curve."

"I already learned not to touch his office," Dean said with a wince. "Or his closets."

"Well," Ellen drawled, "here's the thing. He probably needs somebody like you in his life, which I imagine is why Chuck sent you. But Cas is going to not only fight it, he's not even gonna realize that you could be a huge asset to him."

"And in the meantime I get sent here?" Dean asked.

Ellen nodded, a sympathetic look on her face. "I'll try to go easy on you, but I think you're a perceptive guy. Watch him. He has plenty of tells, they're just not as big as the average person's."

"So instead of rearranging his office, what would you suggest I do to get on his good side?" Dean asked.

"Get him to step outside of his head," Ellen said. "I know that sounds daunting. And you have no idea how to get him out, nobody really does, but there's something about you, something I see in you that makes me think you'd have a better chance than most of us in pulling it off."

"Thank you, ma'am. I think," Dean said with a grimace.

Ellen chuckled. "You'll be fine. It's not gonna be easy, but you don't have a whole lot of choices open to you. Make the best of it. And until then, I'm going to let you do something, but only if you keep it a secret."

"Um, okay," Dean said, stomach clenching with nervousness.

"I'm going to let you come into my office and read up on Cas," Ellen said. "Nothing confidential, but if anyone found out I was sharing the info with a slave, especially about his own master, well, I'd lose my position here."

"You don't have to do this," Dean said, holding up his hands.

"Listen," Ellen said, crossing her arms over her chest. "I've watched that man trudge in and out of this office seven days a week for years. He never smiles. I've never seen him with anyone. I don't think he has any friends. Chuck's a smart guy, which you already know. If he thinks you're the answer to that hot mess up in the penthouse," she said, pointing up, "then I'm going to give you all the ammo you need to make this work."

Dean chuckled. "I think you're overestimating my abilities."

"Hmm," Ellen said, then shook her head. "Nope. I don't think I am. Now follow me," she said, then turned and walked out of the room.

"Do I bring my clothes, ma'am?" Dean asked as he hurried to the doorway.

"Yup," Ellen said, "but you won't be wearin' 'em anytime soon."

Dean sighed as he picked up his things and followed her. Chuck had never made him traipse around naked before. Had never insisted any of the members of the house do that. It was awkward, but Dean knew he shouldn't fret about it. It was odd to him, but not to the rest of the world.

*

Dean's neck was sore and the pillow Ellen had given him wasn't doing much to ease the ache in his ass, but he'd learned a lot.

"Okay, c'mon, kid," Ellen said as she poked her head in the doorway. "The cleaning lady just told me Cas is packin' it up, and there's always a chance he'll forget you're here, so let's get you out in the lobby so you don't get left behind."

Dean quickly dressed and followed her, his muscles protesting the movement after being cooped up in an office all day long. The elevator doors opened just as they made it to the lobby and out came Cas, and yeah, Dean had already started referring to the man as Cas after having been with Ellen all day. He hoped he wouldn't slip up and say it out loud.

"Good day up in the penthouse, Cas?" Ellen asked.

"Oh, Dean," Cas said, only noticing the two of them after Ellen had spoke, which Dean suspected was the only reason she'd spoken. "Ah, yes, it was a good day. I got quite a lot done, thank you, Ellen," he said with a bit of a smile.

"You boys get home safe," Ellen said, waving them both off.

"Thank you, ma'am," Dean said, giving her a smile that hopefully said much more than just 'see ya soon.'

"Goodnight, Ellen," Cas said with a head tilt, and then he was heading for the front door.

Dean followed, frowning when he realized it was dark outside. He glanced at the clock over the front intake desk and winced when he saw that it was eight forty-five. He really hoped Cas didn't stay this late all the time, but after everything Ellen had said and all the things he'd read, it was probably normal for Cas.

"Did you eat?" Cas asked when they got into the car.

"I had lunch, but I haven't eaten dinner," Dean said. "I can make you something when we get home if you'd like."

"Chinese?" Cas said. "I like Chinese. You want Chinese?"

Dean tried not to laugh, and he managed just a small smile instead. "I like Chinese."

"Clif," Cas said, loudly enough the driver could hear him. "Stop off at Wong's, please. Get enough for all three of us."

"You got it, Cas," Clif said.

Dean was taken aback by Clif's use of Cas' nickname, but he didn't say anything. Then he felt silly. Chuck's whole house referred to him as Chuck instead of Mr. Novak unless they were out in public, so why would it be a surprise that Cas was easygoing in the same way?

*

Dean carried the food inside after they said goodbye to Clif. He'd taken his own box and headed on home.

"Do you want me to set a place for you at the table?" Dean asked.

Cas blinked at him for a moment, then shook his head. "I'm really tired. I'm going to take it up to my room and go over some notes while I eat," he said as he took a box of food from the bag Dean was holding.

"Do you want me to do anything for you tonight, sir?" Dean asked, really hoping Cas would give him at least one thing to do so he could prove himself after fucking up so royally.

"No," Cas said, shaking his head. "Enjoy your dinner," he said, then headed upstairs.

Dean sighed as he set the bag on the counter and opened the remaining box of food. He ate, standing in kitchen, then went to bed after he cleaned up.

*

Dean showered and dressed in his everyday clothes the next morning, then headed downstairs to make breakfast for Cas, but Cas was standing in the kitchen, a pen in one hand and a pad of paper in the other.

"Good morning, sir," Dean said.

Cas startled and turned to him with wide eyes. "Oh, good morning, Dean," he said. "I'm making a grocery list for Hannah. Feel free to write down anything you'd like and she'll make sure it's all delivered by tonight."

"I could do the grocery shopping," Dean said, then winced when he realized how forward that sounded. Cas blinked at him. "I mean, I can if you want me to."

"That won't be necessary," Cas said, then did a thing with his lips that might've been a forced smile. "You'll be at daycare all day, so I'll just have Hannah give the list to the grocer."

Dean's stomach clenched. "Oh, okay," he said, nervously looking around for something to do. Cas was sending him to daycare again? Rearranging the office and closet had been such horrible things to do that he needed two days of correction?

Well, that was for Cas to decide. Dean didn't have a say in it. He really was sorry, but if Cas thought he needed the lesson reinforced, then that's what would happen.

"Would you like me to make breakfast, sir?" Dean asked, forcing a smile, and hoping he was better at it than Cas.

"I already had a bagel," Cas said as he wrote on the pad of paper.

"Okay, then I'm going to go change," Dean said.

Cas either never heard him or didn't give a shit, so Dean trudged back upstairs to change into his daycare clothes.

*

Dean kept his head high again. He was upset about being sent to daycare, but that wasn't enough to make him crawl in. He was Dean Winchester.

"Hi, ma'am," Dean said to the secretary, flashing her a smile.

"Again?" she said, then rolled her eyes. "New slaves," she muttered, then picked up the phone.

Dean stood back, waiting for Ellen, but then someone else came down the hallway. It was a man. Shorter than Dean, but his presence more than took up the entire room.

"Dean?" the man asked, his dark suit out of place for the daycare center, but strangely enough looked just right on him.

"Follow me," he said, then turned to the receptionist. "I'll take lunch at twelve forty-five today."

"Yes, Mr. Crowley," the receptionist said, her polite attitude stark contrast to the attitude she'd used with Dean.

Dean followed Mr. Crowley to a different room than he'd been in the day before, but it was set up much the same way. This room was painted a light blue instead of the off white and it had a massage table in the middle of the floor instead of a padded bench.

"Strip, put your things in the basket," Mr. Crowley said as he draped his jacket over a chair near the wall and unbuttoned the sleeves of his red button-down shirt. He rolled the sleeves up, then went to the cabinets on the far wall.

"Yes, sir," Dean said.

"Mr. Novak didn't send any records down for you," Mr. Crowley said.

Dean didn't think the man was looking for a reply, so he just folded his things and put them in the basket by the door.

"Care to tell me why you've been sent to me today?" Mr. Crowley said.

Dean walked to the middle of the room, next to the massage table, and clasped his wrists behind his back. "Master Novak didn't tell me why, but I'm assuming it's for the same reason he sent me here yesterday. I took the initiative while he was away two days ago and reorganized his office and closet."

"You've done nothing since then?" Mr. Crowley asked as he turned around, a clipboard in his left hand and a pen in the other. The whole scene, even down to the way he was standing reminded Dean of Cas earlier that morning in the kitchen.

"I don't think I have," Dean said. "Master Novak just said I was coming here again today."

"All right then," Mr. Crowley said. "We'll assume he wants you punished again. We'll start off with that, then later we'll work on your etiquette. You were obviously raised in a permissive house, and that stance and attitude simply won't do," he said, waving the pen at Dean.

Dean flushed and looked down at the floor. Mr. Crowley was wright. Chuck had insisted the members of his house hold their heads high, that they exude confidence and demand respect, even when they had to be quiet. Dean knew most traditionalists didn't like it, and it was obvious Mr. Crowley was a traditionalist.

"Put your hands on the table and spread your legs, arse out," Mr. Crowley said as he made more notes on the paper, then set the clipboard down on the counter top.

Dean got into position and waited. His skin had still been a little pink that morning when he looked in the mirror. He had hoped hoping Ellen wouldn't punish him again, but it appeared he was out of luck.

"Don't break position, boy," Mr. Crowley said as he pulled something out of the cabinet and swished it through the air.

Dean looked up and had to bite his tongue. Mr. Crowley was holding a cane. He'd never been caned before, but he'd seen more than enough of it on television to know it was very painful.

"You're getting ten," Mr. Crowley said as he walked around behind Dean. "Count aloud. If you miss a number, we'll start over."

"Yes, si-ah!" Dean yelped as the first strike landed. He whimpered, his nails digging into the padding of the table. He had known it was going to hurt, but the depth of the burn surprised him. It hadn't hurt at first, but after a second or two the burn came and kept coming, flaring until finally it started to die down again.

"Count, Dean," Mr. Crowley said.

"One," Dean said, then whined as another strike landed. "Two," he said, his toes curling. He hissed as the third strike sent a flash of pain through his ass. "Three."

"You're not well-trained," Mr. Crowley said, "which is why I'm allowing the fidgeting, but if it continues, you'll be tied down and receive another ten."

"Sorry, sir," Dean said, then bit his lip as the next strike landed. "Four!" he yelled, his thighs shaking uncontrollably.

Mr. Crowley smacked the cane down on the padded massage table, making Dean flinch. He turned his head to look at Mr. Crowley and cringed. The man was angry.

"Did I not just finish telling you to behave?" Mr. Crowley said, voice eerily calm.

"Yes, sir," Dean said, nodding. "I'm sorry. I'm trying to hold still. I'm really sorry."

"I gave you a little leeway because you're untrained," Mr. Crowley said. "Then you proceed to yell at me."

Dean's eyes widened. "I didn't yell at you, sir," he said, shaking his head. "I was saying I was sorry. I didn't mean to raise my voice."

Mr. Crowley stepped forward and grabbed the back of Dean's neck and leaned in close. "Do not tell me what you did or didn't do. It wasn't your apology that was shouted, but rather your counting. This is a punishment. It's supposed to hurt. You take it, you control yourself, then you respectfully tell me what number the strike is."

"I'm sorry, sir," Dean said. "I didn't know."

"Climb up on the table," Mr. Crowley said, letting go of Dean's neck and patting the table with his left hand. "I don't think you'll stay in position and I'm sick of dealing with your attitude."

Dean's bottom lip was wobbling, but he did as he was told. "I'm sorry, sir," he said again. He knew without asking that Mr. Crowley was going to give him another ten strikes.

Mr. Crowley strapped him down to the table with four strips of padded leather. There was one at each knee, one at his lower back, and one at his upper back. Dean put his forehead down on the table and told himself to keep quiet. Or at least keep whatever came out of his mouth down to noises. He didn't want to know what would happen if he swore around Mr. Crowley.

"No need to count," Mr. Crowley said, then laid down the first strike.

By the time Mr. Crowley's cane delivered the fourth strike, Dean was crying, and by the eighth, he was squirming and kicking, unable to control his legs.

"I'm sorry!" Dean yelled, even though he'd told himself he wouldn't. "I'm sorry, sir! I won't do it again! I'm sorry!" he screamed as the last two strikes were laid down, then he sobbed into the table.

Mr. Crowley released the bindings, then dropped a hand towel on the table near Dean's head. "I'll be back in five minutes. Don't move. When I return, we'll start with your training."

Dean put the hand towel over his face and allowed himself a few minutes of crying, feeling sorry for himself. He missed home. He missed knowing exactly where he was in life and what he needed to do. He missed Bobby and Lisa. He missed Chuck, missed Missouri. His missed his mom. He missed getting visits from Sam when Sarah brought him along to discuss business with Chuck. He missed driving himself places and feeling like a responsible adult. He missed knowing what was expected of him.

*

Dean's nose was in the corner for the fourth time. Apparently the answer to "what's for dinner?" wasn't "what would you like?" That's what got him sent to the corner. Corner time was so he could think about what he did wrong, but Dean had no clue what he'd done wrong, and Mr. Crowley was going to come back to the room soon, which meant Dean had to think fast.

"Front and center," Mr. Crowley said, voice stern and really too loud for the room they were in.

Dean was moving before Mr. Crowley was done speaking. He walked with urgency, but didn't run. That was what got him sent to the corner about an hour earlier. When he made it to where Mr. Crowley was standing, he kept his eyes on the floor, put his hands behind his back, and kept his voice calm and respectful.

Of course he still had to think of something to say. "Um, I've prepared a steak and mashed potatoes, sir," Dean said, suddenly remembering a seemingly meaningless comment Mr. Crowley had made a few hours back.

"I knew there was an intelligent man somewhere in there," Mr. Crowley said.

Dean blushed. It was the most praise he'd received from Mr. Crowley all day, and he felt like a fool for soaking it up as much needed attention, but he couldn't help it. He was starved for it.

"Now get your clothes on," Mr. Crowley said. "Mr. Novak is heading down the lift and he'll want to leave right away."

"Yes, sir," Dean said, so relieved he felt like crying.

He'd lived. He'd spent the entire day with Mr. Crowley and he'd lived. Now he could go home and try to prove to Cas he'd learned from his mistake and Cas wouldn't ever need to send him back here again.

Cas looked tired. His tie was already loose, there was a stain on the left side of his jacket, and his hair was even messier than when he'd left that morning. He looked debauched in a way that made Dean's cock twitch. Okay, so that was new. He hadn't realized Cas was hot before.

"I'm too tired to wait for something," Cas said as they walked out of the building. "I called the pizza place down the street from the house and it should be there a few minutes after we arrive."

Dean hadn't eaten lunch, and his stomach growled the whole way home. At first he was worried Cas would notice and give him a hard time for it, but then he remembered Cas never noticed anything. He was too busy reading over something on his tablet.

Dean could barely sit still. The welts from the cane were still sore, but when he'd used the restroom earlier, he'd taken a look in the mirror. Mr. Crowley was very good. There was no blood, just painful lines of red, raised skin.

"I'm going to eat in my office tonight," Cas said as he grabbed a beer from the fridge and one of the boxes of pizza. "I'll see you tomorrow."

Dean really hoped that meant the second pizza was his. He took the box and a soda from the fridge and made his way upstairs, his clothes rubbing painfully over his sore skin. He ate on his stomach, spread out on the bed with a book in front of him.

Hopefully Wednesday would be a better day.

*

Dean held his head high yet again as he walked into the daycare center. The secretary snorted when she saw him.

"Really?" she said, then rolled her eyes. "You aren't too fast on the uptake, are you?"

Dean didn't bother replying. He just stood to the side and waited for his caretaker. He really hoped Ellen would walk down the hallway, but it was Mr. Crowley.

"Come," Mr. Crowley said impatiently.

The only reason Dean was able to follow Mr. Crowley was because he was too afraid not to.

*

Friday morning hadn't come soon enough. Dean didn't even bother changing into his regular clothes, but instead came downstairs in his daycare outfit. He was never going to organize anything of Cas' ever again. He'd volunteer to un-organize things if he could.

Cas wanted to leave early, so they didn't even have a chance to eat before they were leaving.

"Damn, boy," the secretary said, shaking her head.

Dean got the feeling the girl had started to feel sorry for him instead of just disgusted.

"Hey, sweetheart," Ellen said from the hallway before the secretary even had a chance to call.

"Hi, ma'am," Dean said, trying his best to not get his hopes up. Just because she was standing there, it didn't mean she was going to be his caretaker for the day. Dean found that out Thursday when someone new came down the hallway, but they'd been on their way home, Mr. Crowley walking out only seconds later.

"Rough week?" she asked as she waved him back.

"Yes, ma'am," Dean said, his eyes burning with tears.

Dean came to a stop at the room he knew to be her correction room, but she kept on going, so he hurried to follow her. He was a little nervous, but when she opened the door to her office, he relaxed.

He didn't bother waiting for her to ask him. He just started undressing. He folded his clothes and put them next to the door, then stood in the middle of the room while she pulled out his chart and looked it over.

"All right, c'mon over here," she said, gesturing to the floor in front of her. She pulled out some surgical gloves and put them on, then grabbed a tube of something from the drawer. "Turn around and put your chest down on the counter."

Dean's eyes widened, and he tried to see what she was holding in her hand, but then she chuckled, and he looked her in the eye, blushing.

"Mr. Crowley tends to be very thorough in his punishments," Ellen said, then held up the tube. "This is to help with the pain."

"Sorry, ma'am," Dean said, the blush spreading to his ears and neck.

"It's okay, sweetheart," Ellen said, patting his arm.

Dean leaned over, resting his chest on the counter top and relaxing as she walked around behind him.

"A pillow isn't gonna do a damn thing for this," Ellen said.

Dean hissed as she started applying the ointment. He bit his lip and closed his eyes. It didn't hurt that badly, but the whole situation had him on edge.

"Did you talk to him yet?" Ellen asked.

"No, ma'am," Dean replied. "He's always busy."

Ellen snorted. "Yeah, he's always busy. That was my point the other day. He's never going to not be busy. Which is why you've gotta take the initiative."

"Like I did when I organized his office?" Dean asked, then winced when he realized he'd been kind of snarky.

Ellen finished putting the ointment on and took off the gloves, dropping them in the garbage. "You have to know what you're allowed to do and what you're not allowed to do. He's never had a slave before, and because he's too stuck in his own head, he never learned how to treat one properly. He probably doesn't even know he's supposed to tell you what to do. And if he does and he's just testing you, then talking to him is gonna get you there faster. Hiding from it isn't going to solve the problem."

Dean stood up. "My ass hurts," he complained. "If I try to get him to talk and he doesn't like it...," he said, then trailed off.

Ellen chuckled. "That's a risk, but so is leaving things the way they are."

"Yes, ma'am," Dean said.

"Okay, we're going to do things a little differently today," she said. "I'm not going to punish you."

Dean opened his mouth to protest, but then closed it. He'd been about to argue with a caretaker.

"I get to decide what happens to you while you're here," Ellen said. "If he doesn't like the way I handle you, he can do it himself or request a different caretaker."

Dean's stomach clenched. That wasn't what he was worried about. He was worried about Ellen getting fired. He like Ellen. And if she was gone, he'd probably be handled by Mr. Crowley.

"You're gonna help me rearrange the storage room," she said, then walked out of her office.

Dean followed her, nearly tripping over his own feet. By the time they made it to the storage room, he'd half convinced himself she was joking. But then he saw the room and changed his mind. It was a mess.

"Is this a punishment?" Dean asked, looking around the mess of a room.

"This," she said, putting her hands on her hips, "is so you can feel like you accomplished something really great this week."

Dean's eyes started to burn again. She must've known that's all he wanted, was to do something he knew he should do, work hard at it, and be able to say he'd done something well.

"Thank you, ma'am," he said.

"Or maybe it's just an excuse to get you all sweaty," Ellen said, shrugging.

Dean let out a bark of laughter when she smirked at him.

Part 2

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