So I meant for this to be a two shot, but it may end up being more. I'm going to talk to aloggedinreader who wrote the prequel. The ending will be posted around Christmas however, with a slim chance of an epilogue.

It was said that Cas in nothing, but a trench coat and Gabe in nothing, but Sam's clothes hanging off him were the best things. So I put both at once. ^^

Unedited, sorry for any mistakes I am in different modes when writing and editing, but I was determined to get this posted today for the anniversary of Mary's death.

Confused? You probably need to go back and read aloggedinreader's An Aimless Witch chapter 1

Castiel wasn't exactly proud of it, but he had been following the older Winchester almost as long as Gabriel had been following the younger. It was actually when Gabriel first declared he found his witch and showed their brothers that Castiel found his or at least, he hoped. He had found himself drawn to Dean Winchester the moment he laid eyes on him, Castiel just knew that was the man he was meant to guide and connect with. He was as sure as Gabe seemed to be about Sam. There was one little problem, at the time of this revelation for the familiars, neither of the Winchester brothers had been proven to have any magical properties about them. While their mother was a witch, their father was mortal making it only a 50/50 shot.

Castiel sighed from his place on the window sill. He sat stark still in his bushy cat form watching his witch-to-be. The loyal familiar would never admit it, but he was a little jealous of his older brother. Oh yes, Sam proved to be magical a couple years ago, giving Gabriel a one-hundred percent assurance that his connection was real, leaving poor Cas alone to wonder, miserably. A familiar was meant to find their witch and stay with them forever, a witch and their familiar shared a profound bond that no one else could really understand. There were a few rare familiars who jumped between witches, guiding without bonding with them, but every familiar had a witch they were meant to connect to someday. Castiel was sure he found the person he shared that bond with, but it was fruitless if the man never proved to have abilities.

Dean chugged down another beer and Castiel watched helplessly, he wanted nothing more than to go in and comfort the green eyed man. It was the anniversary of what he thought was his brother's psychotic breakdown and the beginning of a downward spiral. On top of that, the younger brother nearly over-dosed on sedatives just over an hour before. Dean was finally relaxing once more, ignoring the doorbell and noisy kids behind it, in favor of watching a movie about a dead man in a hockey mask with a machete. Neither of the Winchester brothers particularly liked the holiday, it was the beginning of the end for them, so to speak. Not to mention, the anniversary of their mother's death being only two days after.

The young familiar found himself admiring the human in front of him even more for his ability to hold it together. It really was pretty miraculous, losing a mother so young and trying to help his father raise his little brother when he's barely past infancy himself. Then only to deal with losing a father and trying to financially support a brother in early college who's also grieving. That alone was a lot to ask of anyone, but he did it with a smile for his little brother and kept that smile even when he was worried out of his mind when he thought his brother was losing his own. Castiel just sighed to himself and was about to head home for the night when something caught his eye, Dean reached into a bag of candy that had been long empty –he watched the Winchester push the red bag full of wrappers aside in favor of a brown bag instead- but in his exhaustion and slightly drunken state, he aimlessly reached into the red bag and pulled out a handful of miniature Kit-Kat bars.

It was enough. Castiel now just had to figure out how to convince the older brother –who already believed his younger brother crazy because a familiar tried to make contact with him- to accept him as his familiar.

Dean was honestly still trying to wrap his head around the raccoon thing while getting into his Impala. Seriously, did Sam even get that thing checked for rabies first? Was this another part of his schizophrenia? Dean would have to talk to the doctor about how to approach the new situation, but he'd talk to Sam first to at least get his perspective before anything. Dean had just turned on his engine, when he sneezed.

He really hoped he wasn't coming down with something, after Sam's episode yesterday, the last thing he needed was to be sick and cause himself to be less attentive and able in making sure Sam was okay. Revving the car, he looked up and jumped in his seat. Laying on the corner of his dash board was a scruffy black cat with bright blue eyes that seemed to stare at him curiously.

"Damn cat! How'd you even get in here?!" Dean cursed with a huff. No wonder he'd been sneezing, Dean was allergic to most furred animals, dogs and cats especially.

The cat just tilted its head like it actually understood what the human had just said. Dean rolled his eyes at the thought -obviously some of Sam's crazy talk was starting to rub off on him- and dismissed the idea before glaring at the cat. "If I find any claw marks in the leather I'm turning you into Chinese takeout."

The cat stared back at him and tilted it's head again like it was confused and Dean ignored the strange feeling of being understood that he was getting from a god-forsaken cat! He leaned acrossed the car and opened the door on the passenger side, pointing to the now opening. "Out Cat, I can't have you in here. I'm probably already going to be sneezing for days because of you, now shoo. I already have a brother and a raccoon to deal with, I don't need a cat too."

The cat just broke eye contact, straightening before he walked out of the car stiffly, almost as if it lacked typical cat-like finesse. Dean pulled the door closed once more and let out a breath. He would never admit it, but besides just the allergy thing, cats had always made him a bit uncomfortable anyway. They seemed to stare straight into your soul and the bushy black one that just left seemed to have a particular knack for it.

"Good riddance." Dean declared with a huff, sitting up in his black leather seat. He turned and put down the emergency break to look up and meet blue once more. The same cat perched on his dashboard, staring straight at him through the windshield! Could the thing not take a hint?!

"Hey!" Dean yelled, after rolling down his baby's window. "Get off you mangy cat!"

The frustrated man revved his car still geared in park, in a weak attempt to scare the animal away. The damn cat didn't even blink. Dean was torn between a state of impressed and frustrated. He groaned and unbuckled the seat belt before exiting his precious car. The stupid cat was going to scratch her, he just knew it! Stepping on the rock of the driveway, Dean was careful to leave the door open after not turning off the car. All he had to do was brush the cat off the car and be on his way. Looking around for fluffy black fur-ball, the older Winchester came up empty. The damn cat had disappeared.

"Problem solved." Dean said out loud, trying to stifle his own doubts -it was a forsaken cat for god's sake- the thing was probably just looking for food or something. He was just being paranoid.

Getting into the impala once more, the door shut with its usual satisfying click. Dean took a breath, trying to re-achieve some sense of calm. He was okay, really. He was Dean fucking Winchester and he would hold it together. Damn everyone who doubted or pitied him, he could hold it all together like he always has.

Turning to finally put the car in drive, the older Winchester yelped in his seat as a fluffy black cat was curled up on his passenger seat silently looking up at the green eyed man before him.

"You!" Dean exclaimed dramatically, pointing at the cat who only flicked his tail anti climatically. "How-?!" He closed his mouth and opened it again, not at all sure how to respond to this situation. He was honestly just outsmarted by a cat. His pride was a little damaged. Dean turned to the cat with renewed determination.

"You. Out. Now!" Dean said, ready to open the passenger seat once more. This time, he wasn't getting out, he'd just go and hey, if the cat didn't move it would be road kill clean-up's problem. He honestly tried the humane method, but now this cat was just trying his patience. The cat sat up and just nuzzled his arm as he tried to reach over.

"Stop it." Dean ordered, thinning his lips. He would not give in! The man pulled his hand away in all refusal to give in and pet the animal. The cat just sat up and looked at him with its big blue eyes, the animal flicked its tail back and forth for a moment and looked like it was trying to decide something before standing and reaching a first paw onto the gear shift.

"Oh no! No! I am drawing a line here cat." Dean exclaimed watching as the cat took the first few steps towards the human. After getting both front paws planted firmly on the smooth surface of the gear shift, the cat used its front legs and leapt forward onto the humans lap. It quickly settled on Dean's lap in a ball, leaning against his torso and giving off content purrs.

Dean stared down exasperated and put his arms up awkwardly not sure what to do with them or make of the situation. The older Winchester sat there for a moment contemplating what he should do, when he could see his brother running up in the distance. He must have only taken a short run, it was probably for the best since he had hardly been out of the house in several months. He was a little out of shape in both social and physical ability, not that it showed at all. The younger Winchester just switched to mainly muscle training when he decided leaving the house was a bad idea. While his outer appearance hadn't suffered –if anything he became even more toned- his lungs had. Dean rolled down his car window as the princess was about to head inside.

"Hey!" Dean yelled, getting his brother's attention. Sam looked at his brother questionably and jogged over to the car, surprisingly enough he still had that damn raccoon on his shoulder. Dean had half hoped it would jump off midway and go to its own home instead of trying to invade theirs. He was having the worst luck with animal invasions lately.

"What?" Sam asked his brother while jogging slowly in place as a cool down.

"This is a problem." Dean said pointing down at the cat in his lap. "How do I get rid of it?"

"Have you tried telling it to leave?" Sam asked with an eyebrow raised staring at his brother bewildered.

"Yes I've tried telling it to leave! Sam the damn thing was in my car! Then when I got it out, it just went on the win shield."

"Okay." Sam said with an eyebrow raised. The raccoon crawled up from hanging on the tall man's shoulder to sitting on it. If Dean didn't know better it would have almost looked like the thing was whispering to his brother. Sam shook his head as he tried to repress an amused smile. "That doesn't exactly explain how it got on your lap."

"When I got out to get it off the car it ninjaed back in then decided my crotch was a good resting place Sam!" Dean said frustrated. He just wanted it gone.

Sam wrinkled his brow in disgust at his brother's crude way of putting things. The raccoon seemed almost like it was laughing though and the cat-. Dean could hardly believe it, but the cat had jumped off him and looked almost, embarrassed? It was a really strange sight to behold.

The cat and the raccoon shared a long look before the cat slowly crept over and rubbed against Dean's side affectionately.

"Do you see what I mean Sam? You're the animal expert. This thing needs to go. I'm going to be stuffed up for days and it's getting all over me!" Dean said clearly frustrated.

"Aw, but Dean, I thought you liked pussies." Sam said cheekily. His little companion almost fell off his shoulder. Giving one last toothy smile Sam left his brother as was to go.

Dean just glared at his brothers retreating figure and sighed. "Fine, you win cat. Ya happy?" Dean said, awkwardly picking up the cat under its stomach with one hand. It couldn't have been very comfortable, but the cat looked okay with it anyway. Dean took the cat and headed inside the house. Stepping just in the front door the man set the cat down and pointed a finger at it.

"You. Stay." Dean ordered, glaring down at the cat. "Do not follow me. I have to go to work and there cannot be any cats in the shop. I will deal with you when I get back."

The cat gave a slight nod and Dean wondered for a moment if he should ask Sam for one of his antipsychotics. Something weird was seriously happening.

At that Dean shook his head, leaving the house once more.

"Alright Cas, you can come out. You're not breaking any rules now little brother." A short man, dressed only in a shirt that was much too big for him. It hung just a few inches over his ass. He stared down at the cat with his arms crossed waiting for an explanation. Sam stood a little to the side looking excited and a little fearful. This was still all new for him too.

The cat stared at Sam, who found himself a little shaken by the animal's intensity.

"Hey! Eyes over here Cas. That's my eye candy- I mean, witch." Gabe said giving the younger Winchester a wink before turning his attention now to a tall, dark and handsome man in nothing, but a trench coat.

"What do you want Gabriel?" The dark haired man asked, stony faced.

"Wow." Sam muttered from his little corner. It was cool when you didn't think you were completely crazy.

Gabe narrowed his eyes looking between the blank stare Cas was giving Sam and the amazed gaze Sammy was giving Castiel. Uncrossing his arms he trudged over to stand in front of his ginantor.

"Mine." Gabe declared, digging his heels into the ground. Sam just blushed embarrassed.

"I have no intention to take your witch." Castiel said blankly

"Then what are you here for exactly? Got done with following the rules and stalking from a distance?" Gabriel asked putting his hands on his hips, slightly patronizingly.

"Dean Winchester has finally shown." Cas said tilting his head slightly at his brother's strange behavior. Gabe had always been enthusiastic about the younger Winchester, he's never seen him so protective before.

"So Deano has magic too? Man Mary really fucked up on the Just-in-case-I'm-not-there guide." Gabe said smiling at his own joke. Neither of the other men in the room were amused.

"That's my mother you're talking about!" Sam declared slightly annoyed. It wasn't as if he ever knew her, but she was still his mom.

"Well it's true!" Gabe defended, smiling anyway because he was still in a state of euphoria over the fact that Sam had finally said yes.

Sam glared down at the short man, who was still standing in front of him in a guarding manner. He wasn't really mad, but the blond familiar could be exasperating.

"It's a family trait!" Gabe said and grinned up at tall witch.

"Huh?" Sam asked confused looking down at his familiar.

"Remember Sambo, open connection between minds?" Gabe stated with a wink at his witch who now looked embarrassed.

Castiel just watched the two men banter longingly. He wanted that. He wanted a connection, but he wanted it with Dean Winchester. After a few more moments, Gabe finally turned his attention back to the interrogation at hand.

"So what are you going to do? Just hang around as a cat until Christmas?" Gabe asked amused. Finally, someone else was going to experience the Winchester stubbornness.

"Why Christmas?" Sam asked curiously. He was itching to get his hands on some books and read up on all of this just so he could keep up in a real conversation.

"It is not actually Christmas. Gabriel is referring to Yule, which takes place between the twentieth and the twenty-third of December depending on the year. This year it is on the twenty-first. Familiars can only make contact on Sabbats or particularly magical days, so to speak. There are eleven days a year we can make contact, only eight are on a Sabbat." Castiel explained to the taller man.

"That's what I said!" Gabe huffed.

"I'm sure that's what you meant brother." Castiel said slightly sarcastically. Castiel never felt completely comfortable with human social standard, cats were much simpler. He could however, pull off the occasional sarcasm. Gabe just gave off his own version of Sam's a famed bitch face.

"Is that why you were able to talk to me on Halloween?" Sam asked the short man.

"Samhain, yea. It actually starts the Wiccan calendar. It means the end of summer Sambo. Figures you would finally say yes on a day with your name in it." Gabe said amused.

"Can't you just turn human and tell him to accept Cas?" Sam asked, forever the problem solver.

"I'm not allowed to interfere while a familiar is trying to make contact with their chosen witch." Gabe said, giving Castiel an apologetic look, even though he knew this already.

"Alright, so that means we have a little under two months to somehow convince Dean to accept Cas, neither of you can actually talk to him and I'm considered crazy. Peachy. Your rules suck."

"Tell me about it, why do you think it took so long to get you to accept me?" Gabe asked, his golden eyes twinkling up at his witch.

"Yes. I must agree. The rules do…suck." Castiel said slightly awkwardly. He didn't want to put Dean through the same thing Gabe had Sam. He wouldn't give up, but he was determined to find another way.

"Can't you at least turn into something Dean's not allergic to, like I dunno a bird?" Sam asked the dark haired man. The two familiars shared a look before turning their attention back to the human.

"Sambo, he can't." Gabe said, slightly pitying his brother. It did figure though, that the human Castiel chose would be allergic to him.

"Not all familiars can change forms the way Gabe can. Most only have a single animal form. There are only four familiars alive today that have the ability, also known as my brothers." Cas said slightly ashamed. He was always expected to have the same abilities as his brothers, but alas it seemed not meant to be.

"Okay…" Sam said trying to process all the information that was just thrown at him. "I do have one last question though."

"Shoot gorgeous." Gabe said openly flirting now. The serious conversation was cutting into his making up for lost time.

"Cas just transformed, in clothing... sorta. So why were you undressed when you transformed in my room?" Sam asked blushing. In fact, Gabe had just transformed in Sam's shirt. Gabriel just wiggled his eyebrows at the tall man.

"Transforming in clothing isn't always considered the most comfortable thing. It can feel confining and often overheating, especially for familiars who have fur. It's like having an extra restricting layer that cannot be seen. Familiars are often nude if they are not claimed and wear light clothing if they are." Castiel stated.

"Yeah and by light he means scantily clad and sexy. Like when Balthazar first got claimed and refused to wear anything more than a g string, but Cassy here's always in that coat. Some weird attachment to it." Gabe said grinning at his brother who just glared back.

Castiel just shook his head, his brother obviously had his mind on other things at the moment. He would seek Gabriel's assistance later when he could focus again. Until then, he shifted back into his cat form and just patted toward the window laying in the sun, with a perfect view to see when the older Winchester would come back.

Dean kicked the door open with his foot, groceries in hand at half passed ten. He was honestly dead tired in the barely standing sort of way. That last car took forever to fix. Dean was surprised to find the black cat, standing at the entrance way, seemingly waiting for him.

"Not right now." Dean said to it, walking right passed to put groceries away. On his way to the kitchen an apple fell out of one of his various bags. Dean heard it hit the ground when he was already a few steps away. Turning back to somehow grab it with his hands already full of bags –after refusing to take more than one trip out to the car- he found he didn't have to because the cat was already rolling it along to the kitchen with its nose.

"Not bad, you're a smart for a little fur ball." Dean said putting the bags on the counter. "But we can't keep you. We'll find somewhere else for you tomorrow."

The black cat just rubbed his face against Dean's legs, mostly staying out of the way when the human moved throughout the room putting the various food items away.

Dean headed straight for his room right after, stripping to his boxers before laying on his bed. He never understood his brother's weird need for sleep clothes. It seemed like extra, unneeded laundry to the older brother.

The cat followed quietly, Dean didn't even notice until it was suddenly laying on the pillow next to his head.

"Seriously cat?" Dean asked. Was it the cat's goal or something to make him constantly stuffy from his allergies? He was much too tired to fight it though and just sighed closing his eyes. "Night ya ninja."

The cat just gave a content purr in response, nuzzling his neck.

Dean's not exactly sure how it happened, but he was currently in the car, his brother in the passenger seat with a raccoon and a black cat in the back seats, on the way to his parents' grave stones. Sam had a bouquet of flowers, some white and some blue. Even the raccoon had two wild daises in its claws. Sam acted like it was completely normal, which to Dean made the whole situation even weirder.

Parking the car, Dean turned off the engine and pulled the keys out, pocketing them after rolling down the window. Sam got out in his full suit, flowers in hand and a raccoon in tow. He was used to his brother's resistance to actually visiting their parents' graves. He trudged on with Gabriel while Dean waited in the car.

Castiel was actually ready to follow the younger Winchester, when he noticed the older wasn't. Instead, Dean reclined his chair and closed his eyes. He looked like he was about to take a nap instead. Castiel jumped to the front seat and stared for a moment, waiting to see if he had just misinterpreted. When there was no change, Castiel pawed the human's leg, but the Winchester ignored him. Castiel proceeded to jump on his lap and got up on his back legs, pawing the human's face gently. Dean just swatted the paws away lightly, not even opening his eyes.

Castiel gave a quick questioning meow and Dean was surprised enough to open one eye and look at the cat curiously. It was the first sound Dean had heard the cat make in all his handling of it. The cat looked out the window toward the graves.

"You can go, I'm staying here. I know Sammy likes it, but the whole concept's stupid. They're dead. That means they're gone. It's not like visiting some stupid grave that doesn't even have either of my parents' bodies actually in it is going to change that."

The cat meowed once more, tilting his head to the side. The Winchester just closed his eye again and continued to ignore the creature. Castiel moved carefully before grabbing the keys out of the humans pocket with his mouth and taking off through the window.

Dean cursed, a lot, before almost ripping off his seatbelt, fixing the seat so he could get out and locking the car behind him, all of which gave the already quick cat a sizeable head start. The cat made it to the graves in no time flat, with the human in the distance running after him and trying to catch up.

Sam looked concerned and Gabe looked amused as the cat dropped the keys off in front of Mary's grave. Dean was still too far to hear so Cas took a chance.

"I apologize for not bringing a gift of reconciliation, but I did bring your son. I hope that is enough." Cas said still in his cat form, before straightening his back and bowing his head.

It was only a few moments before the older Winchester caught up. Looking at the scene in front of him, there were flowers on each of the two graves -his keys mixed in with the white flowers- the raccoon sat dead center between the two while Sam knelt down in a prayer a hand on each of the grave stones, the cat next to him with his head bowed as well. Dean was respectful enough to wait until his younger brother looked up before addressing him.

"Did you put him up to this?" Dean asked nodding to the cat after retrieving his eyes.

"Dean, are you asking me if I told the cat to steal your keys?" Sam asked, just clarifying his brothers thought process.

"You tell me. You're the one who talks to animals Sammy." Dean said rolling his eyes at his brother. Okay, maybe it did sound crazy, but there has been a lot of crazy the last couple of days!

Sam gave him his best bitch face. "No Dean, I didn't tell the cat to take your damn keys. Maybe it just thought you should come visit your parents' graves for once like I've been telling you to do for years! Maybe it thinks you don't have to pretend you're not hurt all the time!" Sam exclaimed letting out a frustrated huff.

"Whatever." Dean said, thinning his lips and turning away from his brother. The cat immediately started to rub against the older Winchester's ankles, trying to calm him.

"Yeah, whatever." Sam responded. Gabe climbed up his back, hugging him gently around his neck, trying to comfort his human. They all stayed like that, silently for a moment.

"I'm going back to the car." Sam declared, not looking at his brother. Dean bringing up the fact he found his brother crazy was uncalled for, especially when it was untrue. Sam walked away, leaving his brother and the cat at the graves alone. Dean knew better than to follow yet.

After Sam was out of sight, Dean looked down at the two graves in front of him. He sighed and knelt down. "Hey ma, dad. You must think I'm a pretty crappy son for not coming to visit sooner. It took a cat stealing baby's keys to come out here."

Said cat just jumped on his knees, nuzzling him, trying to do his part to make the situation a little easier on the human. Dean found himself absentmindedly petting the cat for the first time since it showed up.

"I'm sorry. You know, for not visiting. Dad, you always taught me to be strong, for Sam. I have to protect him you said and I have. Coming here made me weak though. How could I stop Sammy from crying if I couldn't stop myself?" Dean asked, a single tear running down his face.

"It wasn't fair to you though mom. I'm sorry. I'll try to be better. I'll try to hold it all together better so Sam can have the life you always wanted for him. I have to go. I will come back soon mom, dad, I promise." Dean said standing up, the cat jumping off his legs as he moved.

Dean was about to turn away to leave when he took one last look at his mother's grave before him. He reached down and traced his hand over the top. "I love you mom."

The older Winchester turned away, wiping the tear from his face. "Let's go home ninja."

What he didn't see as he turned away, was just a moment after tracing his hand over the grave, the letters in Mary Wincheter's name for an instant, glowed a soft blue.