Dean had been fairly impressed with how Castiel handled the business aspect of the sales regarding Mystery Spot and French Mistake. Mystery was located in northern Virginia and French in Maryland, so Castiel organized meetings with the owners only a day apart. Dean hooked up the trailer and they took a few days to drive out there, leaving a detailed regiment for Gabriel and Charlie to follow in his absence. Castiel understood that Dean would be able to field a lot of the questions about the horses, but ultimately the sale would come down to him. The drive up had left plenty of time for him to lay down what the two colts were worth and how to haggle.

Castiel had managed to pay exactly what Dean had instructed; not a dollar more and not a dollar less. Dean found out on the drive back that Castiel had often dealt with private sellers in artifacts and had experience in the matter. It seemed that every day Castiel surprised him.

Mystery was a chestnut, very tall, and very ill-mannered. He wasn't what Dean would call mean, but he was...sneaky. Somehow, he felt that Gabriel and that colt would get along very well. Frenchie was a beautiful grey, and Dean had great luck betting on the greys. He was smaller and had a bit of a Napoleon complex. The colt was very proud.

Once the two colts had been given a few days to settle in, Dean began their training. As expected, they both exceeded expectations and gave him reason to believe they could both be winners. The topic of another jockey surfaced in the break room, much to Gabriel's dismay.

"I already told you I could ride more than one horse in the Derby," Gabriel stated. "It is completely unnecessary for you to hire on someone else."

Dean rolled his eyes in frustration. He had dealt with a lot of self-centered jockeys in his day, but Gabriel was by far the worst. "I'm not going to keep them from reaching their full potential just so you can ride all three of them. If more than one of them gets a post in a race, I promise to let you have your pick of who you ride.

Gabriel's arms were crossed so tightly around his body Dean thought he might cut himself in two. "Fine, but I choose who we bring in."

"Ah, no." Dean frowned. "That's not how this works, buddy. I'm the one who employs the jockeys around here."

"Then we don't have a deal."

"I don't need to make a fucking deal," Dean snapped, feeling himself reach the end of his patience rope. "I'm the trainer and what I say goes."

"Well you can take your other jockey and shove it up your-,"

"Gabriel!"

All heads whipped around to see an angry Castiel standing at the door with a frightful Charlie behind him. Dean guessed that the groom had just about had enough of the bickering going on between the two and fetched the only person who could deal with it.

"May I have a word?" Castiel asked, jaw clenched and body tense.

"Sure," Gabriel responded, but made no effort to move from his spot at the table.

"In private?" Castiel specified.

"You asked for a word, and I provided it," the jockey shrugged, the smirk on his face taunting them.

"Jesus fucking christ!" Dean groaned, throwing his hands in the air. He had had enough. With a fierce scowl he flung the door open so that it slammed against
the back wall and walked out. Castiel's voice called out to him, but he refused to turn around until he felt fingers wrap around his wrist and tug. Spinning around he saw Castiel standing here, eyes wide with fear behind the glasses.

"Please don't go," he begged, not releasing his hold on Dean's wrist. "I'm so sorry about Gabriel, please don't let him get to you like this!"

"Sweet baby Jesus," Gabriel groaned as he poked his head out of the break room towards the two gentlemen in the aisle of the barn. "I was just joking. I really don't care if you hire another jockey. You honestly think I was the only one Anna kept around this place? Please." He let out a sigh and ran a hand through his long strands of hair. "God, Cassie, you would have thought your boyfriend just broke up with you or something. Try not to look so pathetic next time."

Dean glared at Gabriel as the jockey strutted away and tried to make the anger within him subside. One look at Castiel's face managed to do just that. It was true; Castiel had looked mortified when Dean walked away. "Sorry, I...he's really irritating."

"Yes," Castiel nodded, snapping his hand back to his side. "I do apologize Dean. I would completely understand if you felt the need to fire my brother." Licking his lips Castiel lowered his chin and directed his gaze towards the dirt.

With a labored sigh and a rub to his temple Dean shook his head. "I couldn't do that. For one, the asshole is really good on the back of a horse. Two, he's your brother. He's family. He's just really, really, annoying."

Castiel hummed in agreement and finally met Dean's eyes again. "Lunch?"

Dean felt a smile creep on his lips at the offer, but his gut was falling in panic. The Impala would barely make it to the nearest gas station, and he wasn't slated to be paid until the end of the week. There would be no way they would make it to any kind of restaurant, but he still found himself nodding and responded with an, "Absolutely." Castiel's face lit up and Dean couldn't help but feel his heart sink further into some sort of pit. "I, uh, I just need to go speak with Bobby real quick about the horses and I'll be right out to the car, ok?"

"Of course," Castiel nodded with bright eyes.

Shit, shit, shit. Dean prayed Bobby was still in the workshop in behind the barn working on new shelving for the feed room. When he rounded the corner and saw the plaid clad older man, he breathed out a sigh of a relief. "Bobby."

"Dean," Bobby acknowledged without looking away from his work. "I could hear your argument with Gabriel from the next pasture over."

Dean ignored the comment and instead gave the man a pleading look. "I need to borrow some money. I don't need much, I just need like $10 to fill my tank. I get paid on Friday and I promise to pay you back-,"

"Boy," Bobby sighed and set his tools down so that he could reach into his back pocket for his wallet. "You ain't gotta beg." Pulling out a $20 bill he offered it to the trainer. "And I don't need you to pay me back, either. The way I see it, I owe you a lot more than that."

Dean hesitated, but he took the proffered money. "Thanks, Bobby. I promise I'm going to pay you back."

"That ain't for a bottle of Jack, is it?" His eyes narrowed accusingly.

"I wish," he huffed. "Castiel asked me to lunch again, and I have absolutely no gas left in my baby to get us there."

Bobby lifted a questioning eyebrow. "The two of you sure do spend a lot of time with one another."

Dean rolled his eyes as he pocketed the bill, "Business talks, Bobby."

"Son, I wasn't born yesterday," he responded. "I've got eyes and ears. Get goin' before I change my mind."

"Thanks, Bobby!" Dean waved as he darted back out and around the barn to his house where the Impala was parked. Castiel was patiently leaning against the passenger side door for him. "Sorry, I'm good to go."

"I was thinking a burger joint I saw off of Jillian's Trail, what do you think?" Castiel inquired as he settled into the leather seat. "I hear they have good pie."

A huge grin splayed out across Dean's face from ear-to-ear. "I love me some pie."

/*/

Gabriel let out a hideous belch as he finished the last swig of his drink causing the usual disgusted reactions from the barn crew. "That was good enough I think I need round two."

"You most certainly don't," Missouri objected. "You keep eating the way you do and they won't let you on the back of those horses come race day."

"Come on!" Gabriel whined, "Race season doesn't start for another four months! I've got plenty of time until I have to worry about it."

"I'm fairly certain the horses would disagree with you," Charlie smiled as she allowed Missouri to fill her plate with a second helping.

Gabriel scowled, "Bitch."

The red-head shrugged, "Hey, you're the one who chose to be a jockey. You should have been a trainer instead."

"Oh, yeah, then I could shack up with all my bosses," he gave an amused snort as he poured himself another drink.

"Those boys go off to lunch again?" Missouri asked. "I'm starting to think they don't like my cooking."

"Aww, Missouri, no one could ever hate your cooking," Gabriel purred. "They just need some alone time, if you catch my drift." The man wiggled his eyebrows and smirked.

"I think it's adorable," Charlie grinned, a twinkle in her eyes. "Our very own barn romance. It's like real life fan-fiction."

"If those idjits think they are being subtle, they've got another thing coming," Bobby huffed as he turned the page of the paper he was reading.

"Please, those two are too busy eye-fucking one another to even realize what's going on between themselves," Gabriel said as he swirled the liquid around in his glass thoughtfully. He was starting to think himself a god for practically calling this. The jockey couldn't help but tease them both the moment they set eyes on one another. He had always known Castiel's preference for men, and even he could appreciate Dean's good looks. There was absolutely no way, however, he could have predicted Dean would play ball for the same side. It was almost too perfect.

"And this doesn't bother any of you, the two of them?" Missouri asked with a raised eyebrow as she began doing the dishes.

"Nope," Gabriel responded simply. His brother had sacrificed a lot to come out there and be with them, despite the fact Gabriel had practical guilt tripped him into it. If rubbing dicks with Dean Winchester is what made him happy, then that was fine by him.

"I've known Dean a long time," Bobby began, "And if there's one thing for sure I know about that kid it's that once he makes up his mind it's game over, no matter how idiotic it is. And being involved with your boss is idiotic. I ain't condoning it, but I ain't saying anything against it either."

"Charlie probably wants to beat off to the sounds of them screwing each other," Gabriel grinned in the direction of the groomer.

"I thought you swung for the other side," Bobby frowned over the top of his paper.

"I do," she nodded, "But just because I don't want to have a dick in my vagina doesn't mean I can't heavily appreciate boys loving boys."

"Alright, enough," Missouri demanded. "I won't have this kind of foul talk in my kitchen. Gabriel, don't you have somewhere else to be then stinking up the place?"

"Consider this penance for not giving me seconds, woman," he responded playfully. Gabriel's favorite past-time was getting a rouse out of everyone he possibly could. The only person who had successfully turned him down was Charlie; the woman just seemed to turn everything right back around on him. Missouri gave him a cold stare that he felt to his bone, and decided maybe this time he would pass. "Oh, alright. I'm going."

Slipping on his shoes at the front door he ventured on out into the outside world once again. As he made his way closer to the barn he noticed the Impala parked once more outside Dean's house. Curious, Gabriel strode up towards it. There was no one in it. Peeking through the back window he noticed bunched up linens underneath the back of the passenger seat. Squinting, he tried to make out what it was until he caught the travel-sized pillow buried underneath. The realization hit him all too well. Dean had been sleeping in his car prior to being hired on here.

Gabriel had had to do the same thing when he was first starting out. Anna didn't have her business yet, and he had not made a name for himself. Yes, he knew it all too well. It wasn't really much of a surprise to him considering all the stories surrounding the trainer in the racing world. With a frown he scooted away from the car as to not get caught and headed back to the barn. Kansas needed to be breezed.

Dean had set a routine at the barn that Gabriel kind of liked, and the end of the week came in a blip. That afternoon as he finished putting his gear away he found Dean waving a piece of paper in front of him. "What's that?"

"Pay day," the trainer smiled and handed a check to the jockey. With a pat on the back he added, "Don't spend it all at once," and then he was gone.

Gabriel looked down and his golden eyes widened at the number presented in front of him. That wasn't right. That wasn't even close to being right. Heading towards the desk he grabbed for his binder where he logged all his rides and calculated his fees based on what his average pay was. Yup. The number on the check was exceedingly too much money.

"Hey," Charlie called as she walked in, staring at her own check. "Has Dean paid you, yet? This isn't right."

"He grossly overpay you, too?" Charlie walked up to him and handed him her check. Jesus. Gabriel knew what Castiel paid Dean - not because he was told, but because he's a nosy fucker - and he knew that with what he paid Charlie and himself, Den would have ended up with close to nothing.

"I even saw him try and pay Bobby," she mentioned. "I know I really shouldn't complain about extra money, but this is more than just a few dollars."

It was very rare that Gabriel ever felt guilt about anything, but he knew he wouldn't be able to escape the guilt if he took this money, especially knowing Dean's situation. "I'll go talk to him. Have you seen him lately?"

Charlie nodded, "He was headed back home."

"Ok, I'll go talk to him." Gabriel handed Charlie back her check and stuffed his own into his back pocket while he made a B-line to the house. With more gusto than he normally would have given, he knocked on the door.

Dean was prompt in answering, and there was a look of surprise on his face to see Gabriel there. "Is something wrong with the horses?"

"No," Gabriel responded, inviting himself in and brushing past his boss.

"Well, just come on in," Dean responded sarcastically as he shut the door behind him. "What can I do for you?"

Gabriel whipped out the check and thrust it towards Dean. "I think you need to check your math, Dean-o. It's not right."

Dean didn't even bother looking at the piece of paper as he handed it right back to Gabriel. "It's right."

Gabriel wasn't going to play this stupid ass game. "I'm going to cut right to the chase. I know what everyone here makes, including you. If it weren't for the bloodstock fees on Frenchie and Mystery, you'd make absolutely zero profit after you finished paying me and Charlie. What gives?" He had expected an immediate answer from the trainer, but it was obvious that Dean had not been prepared for anyone questioning their pay.

"Look, just-," he paused and swallowed. "Would you just take the damn money and not bitch about it?"

"No, I won't, because one; I like to bitch, and two; I know you have been living out of your car." Dean's shocked expression told him all he needed to know. "Castiel is far too naive to notice, but I did. I saw the blankets in the backseat and I haven't even been in your car. I also noticed you wearing the same clothes over and over because that's all you've got. I've been in your shoes, and I know what it's like to have nothing."

Dean's jaw clenched and his eyes hardened. "You have no fucking idea what it's like to be in my shoes."

Gabriel gave a snort, "We all have daddy issues, Dean. At least you had your dad in your life. Ours never gave two shits about us, and he sure as hell didn't show up to Anna's funeral. I knew everything there was to know about you before Castiel even knew your name, and I chose not to say a word about it," he admitted.

Dean rolled his eyes, "If you are wanting to hold it as blackmail over me, save it. I already told Cas about my dad and what happened."

"Oh, so he knows about your alcohol and gambling problems that have gotten you arrested and thrown out of some tracks?" Dean's face went red. "Yeah, that's what I thought. So, what? You thought by giving away all your money it would prevent you from placing bets and buying bottles of liquor?"

"Shut up," Dean growled threateningly, his fists flexing. "It's not that, Christ. Look, I'm not exactly great at showing emotions. I don't do chick-flick moments. Paying you and Charlie extra money is the only way I know how to show appreciation."

Gabriel blinked, caught by surprise. Then he pulled a face. "Ugh," Gabriel grumbled. "This is worse than I could have ever thought, then." All the UST between his boss and brother would just continue on at this rate. He might need to call in the cavalry for this one. "Look. I appreciate your...appreciation. But you don't need to take care of us. Castiel takes care of us, and you should let him take care of you, too. He will, if you just let him." Gabriel took the check and ripped it up into four pieces. "Write another check, and pay me what you owe, not what you think I deserve. Do the same for Charlie."

Dean nodded. "Gabriel?"

"Yeah?" The jockey asked, pausing in his reach for the door handle.

"Thanks. For not telling Cas."

Gabriel felt pity for the man in front of him. "It's not my place to say. You're a good trainer, Dean. Most trainers run the horses rabid just to make an extra day's worth of pay. The fact that you put their needs first is good enough for me. Just don't hurt my brother, Dean. I will not let you be thrown out of a track or shoved in the back of a police car in front of him." Not giving another word he opened the door and made his exit. He needed to talk to his brother.

Castiel was at the office desk as usual, with the biggest scowl on his face directed towards the computer monitor. "Did Anna have any sort of financial advisor?" he asked as Gabriel entered without a word and made himself comfortable. "These numbers are making no sense to me."

"Whoa, there, tiger. Don't hurt yourself," Gabriel chuckled. "Frank's number should be around here somewhere. That's usually who Anna went to for that sort of stuff. Look, we need to talk about Dean."

Gabriel did not miss the eye roll he got from his brother. "What has he done to upset you now, Gabriel?"

Propping his feet on the edge of Castiel's desk he threw his head back to stare at the ceiling. "He gave his entire paycheck to me and Charlie."

"And this bothers you?" Castiel's brow knit together in confusion.

"Yes!" He exclaimed. "It doesn't bother you?"

Castiel spun his chair so that he was facing his brother. "What Dean does with his money is none of my business, Gabriel."

"The guy doesn't have a selfish bone in his body. He worries far too much about other people and not enough about himself." He had swung his legs down and was leaning up against the desk.

"Gabriel, I do realize the concept of selflessness is foreign to you-,"

"He lived in his car, Castiel!" Gabriel blurted out. "How did you not notice the blankets and pillow in the back of his car?" Shit. Shit, shit, shit. "Fuck, I told him I wouldn't tell you…Thanks a lot for making me a liar!"

Castiel sucked in a breath, blinking rapidly, then looked away. "I suspected, but I thought it best not to mention. If it were me, that is not a fact I would want publicized."

"Jesus," Gabriel sat back and crossed his arms. "The least he could do is buy himself some new clothes." The sudden change of his brother's expression worried him. "What-No. You are not thinking what I think you are thinking."

"What size do you think he wears?" Castiel asked as he swerved back to his computer and began typing away furiously.

"Nope! We are not having this conversation!" Gabriel quickly pushed himself out of his seat and headed out the door. Those two were absolutely ridiculous.

/*/

Dean let himself fall back onto his bed with an accomplished sigh. The week was done and training had gone exceptionally. Mystery was the only one of the three two-year-olds that made a grand fuss over the starting gates. Lazarus was continuing to get faster and already Dean was making notes of what races to run her in come November. Charlie and Gabriel both bitched that their paychecks were still too high, but they accepted it without too much of a fight.

Dean sat back up and began shucking off his clothes when there was a knock on the door. Throwing on a t-shirt he walked over and opened it to reveal Castiel standing there with a stack of boxes in his arms. "Whoa, let me help you there," Dean grabbed at half of the stack and let Castiel come in. "What's all this."

"It's for you," Castiel explained as he set his stack down on the kitchen table. Choosing one of the boxes he handed it to Dean to open, "Here."

Dean was skeptical, but opened the top of the box to see several brand new polo shirts folded neatly. "Cas...what is this?" He pulled one out and unfolded it to see the farm's logo embroidered on the chest.

"I do realize that you are not exclusive to this farm, and should anyone else ask you to train their horses you are welcome to do so at anytime. However, as long as you continue to train my horses you will be considered part of this family." Castiel gave a warm smile, but it quickly turned upside down. "I do hope they fit."

Dean gave a muffled laugh as he bit down on his inner cheek to keep himself from crying. "Thanks, Cas. This means a lot."

Castiel's face radiated satisfaction. "Good. You'll join me for lunch tomorrow? Gabriel mentioned something about changing the design of our silks. He doesn't want another year of wearing pink and teal."

"Yeah, I bet," Dean gave an amused twitch of his lips. "Sure. Lunch."

"Tomorrow, then," Castiel nodded. "Good night, Dean."

"Night, Cas." Dean watched as Castiel made his leave. There couldn't be polos in every one of these boxes. As he opened each box he felt his heart clench tighter and tighter and a lump form in his throat. One box held various pastel dress shirts and slacks, while another held two nice sport coats. The last box had a few pairs of jeans and an honest to god leather belt. Laying on top of the slacks was a card for a tailor in case the items needed adjustments.

With a shuddered breath Dean took a seat on his bed in shock. A single tear fell from his right eye. No one had bought him anything other than Sam since he was little. Sam. Wiping the tear off his cheek he reached for his phone and pulled up his brother's number. It rang long enough Dean feared it might go to voicemail, but at the last second he heard the familiar voice.

"Dean?"

"Hey, Sammy," Dean responded, a small hiccup in his words.

"Sorry about that, I was finishing up a meeting."

Oh. "Is uh, now a bad time?"

"No, no! What's going on?"

"I'm in Kentucky," Dean smiled.

"Kentucky?! I thought you were in Virginia working with Rufus?"

"Yeah, I was, but I got another offer, and Rufus wasn't paying me shit anyway. You know how it is."

"Well, that's great, right? Do you like it?"

"I love it, Sam," he breathed. "The property is beautiful and the horses are awesome. I really think I might have a winner here, Sammy."

"Dean, that's great! I guess that means you won't be able to come out here anytime soon, will it?" There was definite disappointment in his brother's voice.

"No," Dean agreed, "but I swear if I make it to the Derby you and Jess will have a spot right there next to me in the stands."

"We wouldn't miss it for the world."

"You won't guess who else works here. Bobby."

There was a shuffling noise, like Sam had almost dropped his phone. "Wait, Bobby?! Are you joking? How is he?!"

"Great," Dean laughed, "Everything's just great. We, uh, we talked, you know? Everything's good. It's real good. The owner's name is Castiel, and he doesn't know jack shit about horses, but the guy has the biggest heart, man." Dean could feel his smile grow the more he talked, "He takes me to lunch almost every day, and he's always asking questions. He wants to learn. Oh, and get this - he used to work for the Smithsonian. The two of you could totally geek out."

There was a pause on the other end of the line. "Dean, are we talking about your boss or your girlfriend here?" The words were laced with amusement.

"Shut up, bitch," Dean scowled.

"No way, Jerk. I'm happy for you Dean, I really am. You sound so good. Uh, listen. I'm about to get in the car, I'll talk to you soon?"

"Yeah, yeah, of course. Drive safe." Dean ended the call and fell back to the bed with a smile. Yes, things were indeed finally looking up.