A/N: Well friends, here it is! I'm so sorry I was unable to finish For a Horse With Wings, but I really feel that Into the Hollow is everything that story should have been. I'm so excited for this story and I know that we can finish it together! Come ride with me, everyone!

A dense layer of fog blanketed the acres of Kansas farm land, the horses that stood in the pastures completely masked from view. Dean's breath left his mouth in a wisp of white, the cold air causing him to draw his coat tighter around himself. His head turned slightly to the left to acknowledge the old screen door creaking open. A hand holding a steaming cup of coffee reached out towards him and Dean took it with a nod of gratitude, "Thanks."

"Last one is leaving this morning," Jo mentioned casually, wrapping her arms around herself.

Dean's jaw clenched tightly and he swallowed hard. "Yeah." He lifted the edge of the cup to his lips and took a small swig of the black liquid. It had been six months, two weeks, and four days since the fire. It had been an accident – a faulty wire. He had been at the barn with the horses. To say Dean didn't have survivor's guilt would have been a flat out lie. His parents hadn't been able to get out of the house before it burnt to the ground.

"You can stay here, you know," Jo said simply, sensing what was going through her friend's mind.

There was a small twitch of a smile, but Dean shook his head. "You and your mom have done enough as it is. Besides, I know you all don't have enough money to pay me and I need money."

"She can't pay you," Jo agreed, "But you have a free place to live and free meals. That has to count for something."

Dean did smile at that. "It does, and it has." The insurance money and selling off the horses had managed to pay Sam's college debt from Stanford, but it had left nothing for Dean.

Jo tilted her head in thought, "You could start riding again."

Dean let out a scoff, "Yeah, with what horses?"

Jo shrugged, "You still have Baby."

Dean had refused to let go of Baby. He had been there when she was born, and the pure black mare had become his favorite mount. Ellen had offered to let Baby stay at their farm, and Dean quickly agreed to it. Baby had won him money in many cutting competitions, but he had sold all his tack and he no longer had a truck or trailer. It was too much to ask of Ellen and Jo. "Nah…I think that part of my life is over."

Jo hummed thoughtfully as she took a seat in the rocking chair next to Dean. "So, what are you gonna do?"

"No idea," Dean admitted, his green eyes watching as the fog slowly started to part to show the backs of the horses in the pasture.

"Well," Jo let herself begin to rock back and forth and she took a sip of her own coffee, "maybe Bobby can help you find something."

Dean gave her a questioning look. "Bobby?" Bobby had always been more of a father to him than John, helping the family out with their farm. His new job had kept him busy in Virginia, and Dean had not talked to him since the funeral.

"Oh, Mom didn't tell you?" Jo asked in surprise. "He should be here in a few hours. He was finally able to take a few days off and wanted to come visit."

"That's because he wanted to surprise you," Ellen spoke from behind and she stepped out onto the porch with her own cup of coffee.

"Whoops," Jo cringed apologetically.

Bobby was coming. Dean couldn't help but smile. It would be good to see that cranky old bastard again. "He driving in?"

"Hell no," Ellen said with a smile. "Not all of us are terrified of flying like you."

Dean gave a scowl, "Flying death traps."

Ellen gave him an amused pat on the shoulder. "I've got to head out soon to pick him up. The horses all fed?"

"Yeah," Dean nodded.

"Good. I need you to fix the fence in the east pasture then while I'm gone. Ruger busted it again. Grass is always greener," she mumbled in irritation as she stuck her hand in her pocket.

Ruger was a handful. He had a lot of talent as a reining horse, but he was always getting himself into mischief in the pastures. This would be the third time he had fixed that fence this month. With a groan he stood and took another swig of coffee. "Alright. I'll grab some grub and head on out there."

"Good," Ellen smiled. "Shouldn't take you long. "

Dean grabbed one of the frozen breakfast sandwiches from the freezer and popped it into the microwave as he grabbed his work gloves and shoved them into his back pocket. Naturally, Ruger liked to break the furthest fence away, so Dean saddled up Baby and packed his repair supplies in a saddle pack to ride out to the fence. He let out a groan as they approached the destroyed panels. "Stupid horse," he growled as he dismounted and secured the reins around the horn so Baby wouldn't step on them while she began to graze. Shrugging off his jacket knowing he would quickly warm up he grabbed his supplies and set to work.

By the time he finished the fog had cleared and some of the clouds in the sky had began to part. It would turn out to be a great day. Wiping his brown he placed his foot in the saddle and mounted back up on Baby to head back to the barn. Ellen's truck was in the driveway of the house as promised. Dean made quick work of untacking Baby and ensuring she was brushed off and cooled out before turning her out and heading for the house.

Bobby had been in conversation with Ellen at the kitchen table, but he instantly stopped mid-sentence when Dean entered the front door. He was instantly out of his chair, "Dean!"

"Bobby!" Dean grinned, taking Bobby into a tight hug. Bobby gave him a few pats on the back before giving a final squeeze and releasing him. "You look good, you son of a bitch."

"Back 'atcha, son," Bobby smiled, his eyes watering. "How have you been?"

Dean gave a small shrug of uncertainty, "As good as I can be. Ellen has been making sure I'm well taken care of."

Ellen gave a scoff, "Yeah, so much so he's eating me out of house and home. That boy can put them down."

"Some things never change," Bobby smiled. "Well, come on boy, I know you have work to do around here, so let me help ya."

"Aren't you supposed to be on vacation?" Dean asked in surprise as Bobby pulled on his coat.

"I'm away from my boss. Trust me, that's vacation enough," Bobby assured him. "I don't mind the work, and it'll give me a chance to catch up with you."

Dean certainly wouldn't mind the help with the barn chores, and even if Bobby just stood there and watch he'd appreciate the man's presence. "Alright, then."

"Come back in at noon. I'll have some lunch for you," Ellen called out as they headed out the door.

Bobby helped Dean gather supplies for the stalls and they began to work making mostly small talk until Bobby decided to take the conversation a bit further. "How have you been, really?"

Dean dumped the load of stool into the wheel barrow and paused in his work. "Honestly? Shit." He leaned up against the handle of the rake and sighed. "I lost my parents, I lost my house, and I lost all my horses except for Baby. How else am I supposed to feel?"

"You're supposed to feel like shit," Bobby agreed, "But I know you, son. You like to keep it all bottled up and eat atcha. I'm surprised you even admitted you're feeling that way."

"Yeah, well," he used his foot to get the rake below the clumped up shavings, "half a year is a little too long to keep up the charade, I guess. I'm also unemployed, and the funds for Sammy are going to run out by the end of the year. Going to school is the only bit of normalcy the kid has had since all of this shit happened. I don't want to ruin that."

Bobby nodded and rubbed at his beard thoughtfully. "Well, it's not ideal, but I do know my boss is hiring. He's a pretty big dick, but the money ain't half-bad if you can put up with him."

"Yeah, doing what? Repairing fences for the rest of my life?" Dean asked with a little bit more bite than he meant. He really was grateful for what Ellen had done for him, but doing regular barn chores for the rest of his life really wasn't what he was looking for. Of course, he had helped out at Winchester Farms, but his parents had hired Bobby for that so that he and his father could concentrate on their horses.

"I ain't out to give you my job, boy," Bobby fired back accusingly.

Dean lifted an eyebrow, realizing he really didn't know what Bobby was even doing these days in Virginia. "Fine. Doing what?"

"I work for the man that goes by Castiel Novak and his sister, Anna Milton. They've got a big farm, lots of money. They have two barns with apartments above them. It wouldn't be much privacy, but there's room enough for a pull out bed in mine."

Dean nodded as he took in Bobby's words. He needed a free place more than he needed privacy at this point. "Ok, and what would I be doing?"

"Castiel can't seem to keep a groom around longer than a month. He's one of the top riders in the US right now, so he attracts a lot of people, but scares them away just as easily," Bobby explained.

"Never heard of him," Dean mentioned as he lifted the wheel barrow and moved it back out of the now clean stall.

"That's because he ain't a western rider," Bobby said simply.

Dean straightened with a frown. "English? I'm not working for a stuck-up English-riding douchebag."

Bobby rolled his eyes and set his rake against the stall wall. "Boy, the doucebags aren't limited to English riders. Yeah, he's bit of a dick, but if you can just brush him off for a few months he gets a lot more tolerable. And he pays well. You need money, don't you?"

"Bobby, I don't know the first thing about English riding!" Dean argued, throwing his hands up in a defeated motion.

"So learn!" Bobby argued back. "Despite it all, Castiel does like me and his sister loves me. If I recommend you, I know they'll give you time to learn. Most of those kids that want to come in and work for Cas want to become some sort of apprentice and learn from him. Cas has students for that, so he never pays a mere groom much mind. You aren't worried about that. You can concentrate on the job, and that's what he needs."

Dean swallowed nervously, rubbing at the back of his neck in confusion. English. It might as well have had nothing to do with horses it was so different. The horses were different, the tack was different, the clothes were different. He'd be driving blind into this. "So you want me to go all the way to Virginia to be a bitch-boy for an asshole who rides something I know nothing about?"

"That's exactly what I'm saying," Bobby said with crossed arms. "You got any better options right now?"

No. He didn't. With a defeated sigh and slumped shoulders he asked, "How much we talking?"

Bobby gave an uncertain shrug, "Don't know exactly what he pays the grooms, but I know I make forty a year, and they give me paid time off. It won't make me rich, but I often times don't even have to work 8 hour days depending on the days. And I live rent free."

Forty-thousand just for barn chores and maintenance? Jesus. There's no way he could turn that down. Surely he could just suck it up and deal with this Cas guy for that kind of cash. "Fine, but I'm not flying."

/*/

That night, Dean opened up his laptop and did a search on his hopefully future employer. Castiel Novak, part-owner of Lazarus Equestrian Center in The Plains, Virginia, was currently the fourth ranked rider in the United States in Eventing. The man was only a few years older than him with dark unruly hair and blue eyes like Dean had never seen before. His jaw was chiseled beneath a dark stubble. Dean had to admit the rider was very attractive, but he could see the attitude Bobby accused him of having in his demeanor even in photos. Anna was the complete opposite. She had firey red hair and a bright smile. She used to ride Eventing until she got in an accident and now competed at the Grand Prix level of Dressage.

Curious about the facility, he Googled Lazarus Equestrian Center and clicked on the link that lead him to the website. His jaw dropped instantly at the photos that came in and out on the screen. The facility had hundreds of gorgeous green acres with multiple arenas, galloping lanes, and a full-fledged cross-country course. The indoor arena was completely enclosed with windows and the barns were so extravagant that he wouldn't mind renting a stall to live in. It was incredible. He'd seen some pretty pimped out farms in his day, but they were nothing compared to this. Dean wondered if Bobby's living area was this extravagant, too.

Dean wondered why Bobby hadn't talked it up more than he had. Did Castiel really have his head stuck so far up his ass people couldn't tolerate it for this? Dean just didn't believe it. "I can't believe I'm going to drive 19 hours for a job I don't even know if I have yet." He closed the lid to his laptop with a sigh and pulled out his phone, scrolling down to his brother's name.

It rang several times without an answer, and he was sure that it would go to voicemail, but at the last second his brother answered.

"Dean! Hey!"

Dean smiled at his brother's voice, "Sammy! How's it going?"

"Good! Sorry, I couldn't find my phone under all the freaking paperwork on my desk."

"Just checking in," Dean spoke casually as he stood and began pacing around his room. "Wanted to see how you were doing."

He could almost hear the smile in his brother's voice. "Uh, I'm good. Real good. The job's tough, but good."

"I know you'll have your name up on the door before you know it," Dean smiled, happy that his brother was doing what he always wanted. He loved horses, but that life had never been for him. "How's Jess?"

"She's good. She's really enjoying her job at the museum. We don't see each other as much as I'd like right now, but it'll get better. What about you? How are Ellen and Jo?"

"Good, they are both good ," Dean responded as he stopped his pacing and took a seat at the edge of the bed. "Bobby came to visit."

"Bobby? Wow, how is he?"

"He looks good. He's got a sweet gig out in Virginia at a fancy English barn," Dean explained, his right leg bouncing up and down anxiously. "He uh…wants me to go work with him out there."

"At an English barn? What would you be doing? You don't know anything about English," His brother said, clearly surprised.

"Yeah, yeah I know," Dean agreed, rubbing his hand across his face. "But it pays and, Jesus Sammy, you should look at the photos on the website."

"Well, I guess if you are just doing barn work that you don't need to know anything about English."

"Yeah, about that," Dean flinched. "The job opening is for a groom."

"Dean, not to be the bad guy here, but do you really think they'll hire someone for that job who doesn't know anything about the discipline?"

Dean gave an absent shrug, "Yeah, I said the same thing when Bobby asked me, but apparently the head rider is somewhat of a douchebag and no one can stand working for him more than a month. Bobby thinks I'll be able to handle it and that'll be enough for them to hire me."

"Why don't you just stay at Ellen's place and help them out with the horses? You can help Jo show," Sam suggested.

"Ellen can't afford to pay me anything right now, and as much as free lodging and food helps, it doesn't pay for clothes or gas or anything else. I need money, Sam," Dean growled, trying not to sound frustrated.

"Ok, ok," Sam said. "You know if you ever need money you can ask, right?"

"I'm not taking your money," Dean stated firmly. "DC is expensive, and if I know anything about you and Jess you'll probably having to support another human being before you know it. I'll do some research between now and the trip and just learn as much as I can. Besides, who can resist my perky nipples?"

Dean could practically hear his brother rolling his eyes. "Well, good luck. Let me know how it goes, ok?"

With a sigh Dean agreed, "Yeah, sure thing. I'll talk to you later."

"Yeah. Bye, Dean."

Dean hung up the phone and held it to his lips. Looks like he was headed to Virginia.

/*/

Bobby – the sneaky bastard – hadn't even bothered booking a return ticket, hoping Dean would agree to go back to Virginia with him. For the first hour of the drive, Dean had ignored his surrogate father, but he couldn't stay mad at the man. He was only trying to help. As they drove through Kentucky, Bobby had Dean pull off the main highway. Dean watched as they came up to a massive farm with a sign that read: Kentucky Horse Park.

"Turn in here," Bobby instructed.

Dean put the turn signal on in the Impala and did as instructed, but still asked, "Why?"

"You want to see what you're getting into, don't you? This place hosts a lot of different events, Western included, but the biggest Eventing show in the US is held here every April. An old buddy of mine works here and he said I could bring you around."

Dean drove up the long driveway, looking around in awe at how big the park was. There were several barns and an arena off to the left, but none of that is what caught his eye. It was the stadium that stood tall and proud in front of him. "The hell?"

"The Rolex Kentucky Three Day Event, or better just known as the Rolex. Brings in tens of thousands of spectators that weekend and riders from all over the world," Bobby explained as he had Dean park the car outside one of the barns. Both men got out of the car and Dean followed Bobby up the road towards the stadium. "Eventing is basically a triathlon. Day one is Dressage, day two is cross-country, and day three is show jumping. Dressage and show jumping are held in the stadium, and cross-country is any green grass you see."

None of it made any sense to Dean. "What do you mean any green grass?" Bobby motioned for him to follow him off the road onto the grass and took him towards a giant log that was just randomly lying in the middle of the way. As he looked around, he noticed it wasn't the only obstacle lying out there. "What are these?"

"Jumps," Bobby said simply. "Most of the jumps the y can move and store away during the off-season, but a few stay out here all year long."

Dean's eyes widened, "The horses jump that?" The obstacles were huge. No way Baby could ever make it over one of those.

"Sure do. And that one's pretty small compared to some I've seen Cas jump. It takes a lot of courage and strength for the horses. A course at this level is usually about six miles." Bobby continued on the walk up the hill, mostly in silence, as he let Dean take it all in. After a good ten minute walk they reached a far corner that seemed to be the edge of the park with a huge hole in the ground with jumps. "They call it The Hollow. The horses have to jump up hill with a huge drop at the other side down into the valley, over another jump, and then back up the hill with a jump that comes up real quick on them. It's one of the most challenging questions for a horse on this course. Causes a lot of problems for some riders."

Dean could sympathize. He felt like the fire had been the drop on the other side of that first jump. He hadn't seen it coming. "So this is what Cas does, huh?"

"Yup," Bobby nodded, taking in a deep breath of the crisp Kentucky air.

The Horse Park was beautiful in the early daylight. Part of him wondered what it was like for Castiel to gallop on his horse through these fields at a show. Western certainly didn't have anything like this. "Does he even know I'm coming?"

Bobby let out an amused huff. "Not a chance. I let Anna know, though. She's definitely the more reasonable out of the two. I've told her a lot about you, and she agrees that you are what he needs."

Dean didn't even know what to say to that. His green eyes looked down in the hollow again, his mind racing. "I don't even know if I want to work with horses anymore, Bobby. Too many memories."

Bobby placed a comforting hand on Dean's shoulder. "You love horses way too much to give them up, son. You are just reminded of it because it's too similar. I really think being at Lazarus is going to be enough of a distraction while still being around what you love. Plus…" Bobby looked down at the ground solemnly. "I need you to do this for me, Dean. It's selfish, I know, but after your Daddy died I should have taken care of you and I didn't. This is my way of trying to redeem myself."

"Bobby-," Dean tried to protest but Bobby cut him off.

"You and Sam are like sons to me. Always have been. I shouldn't have up and left, but I did, and I regret it. If I can make it right by getting you a job, let me."

Dean had never blamed Bobby once for anything. When he and Sam were still too young, it was Bobby who watched after them while John and Mary went off to show. He'd always been more of a father to them. Deep down there was a part of him that wanted to take Sam's advice and just stay back at Ellen's farm, but he knew he'd regret it. He couldn't live out the rest of his life like that. "What if I turn out to be a fuck up and they blame you for it?"

Bobby smiled, his eyes starting to water. "Son, you could never be a fuck up at anything involving horses. I don't care what discipline it is."

Dean cast another glance towards the stadium casting a shadow on the course. "Well…let's go meet Castiel."