A/N: Hi! Thank you all for your nice comments! I'm aiming at wrapping this up in a happy ending at around five or six chapters, so almost there.

Possible trigger warning: panic attacks

"I swear my family waits until the last possible minute to get packed." Castiel groans. He, Charlie, and Dean were in the living room with all their luggage waiting for the Novaks.

Dean checks his watch. "Jess and Sam aren't even here yet. Sam knows I like getting there as early as possible." His leg has not stopped shaking since taking the seat on the floral couch.

"Chill. We still got two hours until the flight leaves." Gabriel stumbles down the stairs with his suitcase that is on the verge of exploding.

Dean takes a deep breath, fidgeting with his hands.

"Its okay, Dean. I too like having ample time to prepare for boarding." Cas pipes up.

"Agita, again?" Charlie frowns rubbing soothing circles on Cas's back.

"I'm fine once I actually board the plane."

"Ugh, can we not mention that word. I like to pretend I'm not close to doom." Dean looks at his watch again.

Just then the front door swings open and Sam and Jess come in with Sam carrying a duffle bag and rolling a suitcase behind him.

"Ah, Sam, Jess. Looks like we're all ready to go." Castiel's mom strolls in from the kitchen, carrying a backpack presumably with sandwiches for the entire family.

Cas rolls his eyes.

"Cars all good, let's go pack it up." Castiel's father emerges from the garage.

Two hours later the Novaks and Winchesters are comfortably seated in the airplane.

Chuck and Becky found it necessary to have Gabriel in their row so they could keep an eye on him. Alife insisted he sit next to his older sister, so that made up a row of Alfie, Jess, and Sam. That left Cas, Charlie, and Dean in another row.

"It's only an hour, Dean. We'll be on the ground before you know it." Charlie smiles comfortingly towards Dean.

Cas pulls down the shade. "Look, you can pretend it's the Finding Nemo submarine at Disneyland."

Dean breaths deeply, "That ride makes me claustrophobic."

"Well I get claustrophobic on airplanes, so you're not alone." Cas states grabbing onto Charlie's hand as he suddenly feels the walls of the plane closing in on him.

"Yay a flight with two people who have anxiety flying. This is going to be so much fun." Charlie yelps slightly as she feels her other hand being gripped with the might of a thousand suns. "Okay, close your eyes, both of you. Think of Scarlett Johanson in Iron Man 2…or Gwenyth Paltrow…or Robert Downey Jr. Now put your headphones in and enjoy the view."

Both of them do as she says. Soon she hears relaxing sighs from both of them and a lessening of grip on her hands. And then the plane hits turbulence and Dean abruptly yanks his headphones out.

"What the hell was that?"

Cas with his headphones in and eyes closed doesn't notice.

"Just a little air, no big deal. See we're fine." She nudges Cas for help. He lazily opens his eyes and pulls out one headphone.

"He's freaking the fuck out." She mumbles into her shoulder so only Cas can hear.

"Oh great, fuck. Now I have to pee." Dean grumbles.

"Can you hold it for another…" She glances at her laptop that has the arrival time. "45 minutes?"

"I think the desire to not stand up on a swaying unnatural gravity defying device far outweighs the urge to pee."

"It's probably anxiety pee." Cas speaks.

Deans look at him with a wtf face. "A what pee?"

"An anxiety pee. Right now your body is experiencing a complete imbalance of hormones. A side effect is the feeling of having to pee, but not really having too."

"Ooh look now only 44 minutes left." Charlie points at the laptop screen.

Dean groans. "I need alcohol."

"Unfortunately on such a short flight, they don't offer beverages. I could give you a blowie to calm you down?" Cas jokingly offers.

"Cas, now is not the time to flirt with Dean." Charlie speaks, frowning from the increasingly constricting grasp on her hand.

Dean grunts, pulling down the lap desk in front of him. From Cas's angle the plastic tray hid nothing and he saw a rising in the jeans. Score.

The rest of the flight is spent in silence, except for the audible deep breaths from Dean.

"Michael said he and Adam were coming to pick us up. Castiel can you call him, please?"

Cas did as his father asked and dialed Michael's number.

By the time they had gathered all their luggage, Michael and Adam had found them in the airport.

"Welcome to Chicago, family!" Michael said after giving each one of them a hug.

They divided up into two groups; one would travel with Michael in his SUV to the house, and the other group with Adam in his 4Runner.

Charlie and Cas sat together in the very back of Michael's car, squished next to two suitcases.

"So, who's Adam again?" Charlie asks.

"Michael's roommate."

"Oh."

"Adam has a cute sister. She's twenty and an undergrad at NYU." Cas says suggestively.

"Hmm, and will we get to meet said sister?"

Cas laughs, "Yeah, she's helping my mom with her new blog."

"So, I guess we don't really have to enact any plan to get you with Dean, huh? Since you two are moving in with each other next month." Charlie changes the subject, not so delicately.

"So, you spent a month contemplating a plan and didn't really come with anything did you?"

"Hey, I came up with an awesome plan. And then a week later, you told me you both had decided to become roommates."

"Yeah, just roommates. He's still dating Bela."

"Oh come on Cas, have you seen any movies? It's a classic scenario. I give you both a week before you're jumping on each other."

Cas rolls his eyes at his over optimistic friend.

A few minutes later they are pulling up to the Novak vacation house. Michael's car runs over the gravel, causing Cas and Charlie to bump up and down, Cas's hair grazing the roof.

As soon as the car is in park, they all flood out of the car.

Cas leads Charlie to their designated room. They both set their suitcases down and make their way downstairs, dodging the rest of the family claiming the different rooms.

Dean looks around the hallway with his duffle bag hanging from his shoulder and an overwhelmed expression.

"First room in the left hallway on the right has a great view, and its own bathroom." Cas whispers to him pointing towards the hall. "If you want to come along me and Charlie are going to the lake right now, to avoid my mom's schedule meeting."

"Thank you." Dean smiles. "Yeah I'll meet you guys down there."

Cas and Charlie continue down the stairs, making sure to avoid the kitchen where Cas's mom was sure to be herding family members. Cas never understood how his mom felt every minute of vacation should be planned. He and most of the other family members ignored her pleas until she gave in and let everyone do their own thing. And besides the whole family knew she just wanted to spend time with her husband, she just liked organization.

"Wow this never stops being gorgeous." Charlie gasped as they walked to the end of the dock.

"Remember that one time you tried to take a picture of it and Gabe knocked you and your camera into the water?" Cas asked sitting down on the end of the dock.

"Yeah, little bastard. He was what like five and being a torment?"

"Wow." Dean whistled.

Cas turned around to see Dean strolling over to them. Cas's eyes followed him as Dean settled next to Cas.

"My dad would have loved to draw this." Dean says, planting his hands behind him.

"It would make a very beautiful drawing." Cas's eyes returned to the rippling water, the sun just hitting the horizon of the water. He imagined the blending of an orange colored pencil with a red one, merging just with a light blue.

"So, the city today!" Charlie exclaims, brushing a comb through her hair.

"I think I might just stay here. I'm not really feeling very well." After the past couple of days of non-stop activities like fishing and visiting several museums, his body had grown tired and decided to give him an ugly stomachache.

"Oh, that's not good. Do you want me to stay here with you?"

"No, its fun going into town, you have to go. I've been several times. I'm fine. Just gunna watch TV." He mumbled tasting something acidic in the back of his throat. He climbs off the bed to make his way downstairs to give Charlie privacy to get ready.

He curls up on the huge couch and turns the TV on. He leaves it on TNT, and finds his eyes fluttering closed.

"Anything good on?" Sam walks in, sitting next to him on the couch.

"Some marathon." Cas mumbles into his arm.

"Ooh, you don't look so good."

"Stomach not feeling well."

"Oh, you want some medicine? A bucket?"

"I'm fine, thanks." Cas sits up, getting the rare subsidence of pain in his stomach.

"Hey, can I talk to you about something?"

"Sure." Cas had only remembered Sam asking him that once and that was when he was asking how he should propose to Jess.

"What do you know about Bela?"

"Um, not much I guess. She went to high school with Jess, that's about all I know."

"Yeah, but she was close friends with Jess in high school. You must have been around her a lot. What was she like?"

"Honestly?"

Sam nods his head.

"She was pretty terrible. She was nice to Jess I suppose. But for some reason she just has a terrible vendetta against me. You know how you taste a horrible food and you feel like everything is about to come up at once? That's how I felt every time I heard her voice."

"Ah damn I'm sorry man." Sam leans in to hug Cas, but leans back again remembering he was ill.

"That pisses me off so much like what a fucking bitch."

"Why are you asking?"

"I didn't already get a good vide from her. And now that she's dating Dean…"

"I get it. I have a plethora of siblings I care for."

"I'd much rather he be with you, to be honest."

Castiel felt this conversation had just become much more uncomfortable. He'd much rather have left it at talking about his childhood bully who was now dating his sister's brother-in-law.

"I remember he would always tell me and Jess how every time he talked to you, you would get flustered. He thought it was cute. And then at Gabe's party he felt it necessary to make commentary on how you were a grown ass man now and it was intimidating. I don't know ever since I met you I always just pictured you as an adult. You are way ahead of your age. Or maybe it's just your vocabulary. Anyways, I better go get Jess. We're supposed to leave in a few minutes."

Sam gets up and the view of such sudden movement sends Cas's head spinning. And then his stomach. He lurches forward, hurling into the trashcan he had set in front of himself.

Sam pats his back, while avoiding looking at the mess.

"Hey, you know what, Dean's not going into the city. I'll go get him. He can watch over you."

Before Cas could protest, Sam was out of the room.

Dean walks in, when Cas is in the middle of emptying his stomach.

"Oh, geez." Dean rushes over to the couch, placing a hand on Cas's back, rubbing in a comforting manner.

The hurling seemed to take a pause and Cas sits up a bit.

"I'm going to go get you a cold towel. And some water?"
Cas only has enough energy to half shake his head once.

Clasping the trashcan, he realizes the container won't hold much more and panic sets in. That is until Dean returns with another bucket, switching them out. He places the cool water soaked towel on Cas's neck.

From his crouched position Cas can hear a water bottle being opened.

"Here take a small sip."

Cas angles his head slightly to accept the tilted water. "Thank you." He mutters.

"No problem. You need anything else?"

"No, thank you. I actually feel significantly better. I think I got it all out." He leans back slowly, fearing any quick movements will return him to the bucket.

He feels a hand on his clammy forehead.

"You're hot as hell. Let me go get you another towel." When Dean leaves the room, Cas removes the other towel from his neck. The heat emanating from his body had already claimed the towel useless.

"Here you go." Dean pats the towel across Cas's forehead before setting it there. "You maybe want to watch some TV?"

Cas nods his head.

Dean grabs the remote and finds something slightly more entertaining than what's on. He finds shark week and turns up the volume a bit.

"Aw yeah. Friggin' sharks are badass." Dean says smiling as an animatronic shark bites down onto a couch. "Hey, I've seen that guy on Youtube. PhillyD, yeah. You ever see any of his videos?"

Dean turns to look at Castiel who has his whole body stretched out on the couch and ottoman, fast asleep.

Dean laughs and grabs his hand, holding it reassuringly. Dean feels the clammy hand tighten its grasp. He smiles and returns to watching Shark Week, holding Cas's hand in his own.

Dean proves to be a good nurse, because it only takes Cas one day to recover. The next day he takes it easy again and stays home to watch movies with Charlie.

The day after, though, he is fully prepared to go on a boat trip with the whole family.

He relishes in the comfort of being surrounded by family. Charlie is sitting next to him, talking all about how her OTP would love to be in a kayak here, and she's pretty sure she's actually read a fanfiction of something with that story line. Gabe, Michael and his dad are at the end of the boat, fishing. Sam, Alfie, and Dean are in the water swimming around the stationary boat. His mom and Jess are slathering on tanning oil and lounging at the front of the boat, with drinks in hand. He feels a certain serenity in this moment, being surrounded by all the people he loves and the water that instantly relaxes him.

After an hour, the sun is going down and the family becomes tired and hungry, so they head back to shore.

After they've scarfed down their hamburgers and hot dogs, its starts raining. They make their way inside to gather around the fireplace and have inside s'mores.

"So, Michael you got promoted at work? What do you do in your new job?" Becky asks after they've all gotten settled into seats.

"Its basically the same job, except I assign projects and I get to choose my own projects."

"Well that's good. So you've taken more of a boss position." Chuck comments.

"And how about you Jess. Are you excited for another new year teaching?"

Oh no, the moment Cas had dreaded. They were going down the siblings by age. He was next. He didn't want to dredge up his panic about moving away from home and having to become a full-fledged adult. He had been fine casually bringing up the move and making important decisions about it, but until now it hadn't felt real.

"I am excited. Sam just made me the cutest calendar to keep track of birthdays."

"So, you're only teaching half the year, right? And then taking the rest off?" Becky asks.

"Yes, that's the plan. I'm going to have a TA the entire time I'm teaching, and then she's going to take over."

"Eek, how exciting. Baby Winchester is on their way." Charlie squeaks.

"Oh speaking of which, we have some news regarding Baby Winchester." Sam speaks up from underneath Jess sitting on his lap. "It's a boy." His full grin reveals all of his pearly whites and all of his excitement.

"Bobby John?" Dean looks over at Sam; Sam and him laugh at the inside joke.

"We're a little ways away from choosing a name." Sam responds.

"That's a lie. We just can't agree on any." Jess laughs.

"And you Castiel, you're moving out! New school. New town. Are you excited?" Cas's mom's eyes finally settle on him. The words send an alarm to his brain and he can feel his lungs constricting.

"Yes, very exciting." He hopes they can move on quickly and ask Gabe about high school.

"And you're moving in with Dean. That's gotta be a relief, right?" She continues, trying to make the life altering experience seem better. It doesn't seem to help because he can now see spots. He imagines having to go grocery shopping by himself. Being away from his family, his best friend. Having no friends, except for Dean. He gets up too quickly and his whole body sways.

"I need some air." He stumbles to the door. He hears mumbles of concern. "I'm fine, carry on, just need air." He steps out on the patio feeling a blast of cool air on his face. He breathes in the cold air. The coldness steadies him just enough that he can walk to the dock. He sits down in the rain and tries to go down the list of things that help when your having a panic attack that his therapist had told him. One. Breath. He tries to breath deeply, but can only breath in quick short huffs. Two. Excerise. The panic can't catch up to your body. He tries to pick himself up to do some jumping jacks, but falls back down from his shaky legs. Three. Realize that it is anxiety. Sometimes identifying helps stop it. He labels his reaction as anxiety in his mind, but it only just reminds him that he is having a panic attack and that scares him more. Four. Cry. He feels warm droplets dropping from his eyes. It seems he had concealed them for a while, because a downpour of tears roll down his cheeks. It seems to be helping him breath and fight off the dizziness, although now his body is trembling from his sobbing. He's thankful the weather decided to be shitty, because the cool rain is making him feel better while wiping away the tears.

He takes a deep breath, when he feels a hand on his shoulder.

"Hey, can I sit here?" Cas turns to see Dean peering down at him. He nods his head and turns his head away, trying to conceal his splotchy, panicked face.

Dean slides an arm around Cas and pulls him close.

"Hey, man, its fine to be scared of moving out. I mean I balled in my room for two hours before I left for school. I couldn't imagine leaving Sammy and Bobby for a school that was across the country."

Cas couldn't seem to calm down, his sobs sent tremors through his body, despite the comfort he felt being in Dean's arm.

"Okay, tell you what. I'll sit here and talk, and at any time you want to chime you can?"

Without a response, Dean continues, "You know, before this vacation is over I think we need to prank Sam. I mean last vacation we went on, he thought it would be funny to cut holes in the ass of my swim trunks. I still haven't gotten him back for that." Dean pauses, allowing Cas to speak up.

When he doesn't, Dean continues. "Your sister, she's one badass chick. I've never told Sam, but I'm so proud of him for finding her. I'm so happy for them. And because they got together, I got a whole new family. I'm so grateful for your family. I love them all to death. But I think I love you the most. The way you jump at any opportunity to help any of your family members. You have so much love, and it shows in how you are with your family…and your friends. Charlie's damn lucky to have you."

"I can't do it." Cas turns to finally face Dean, rain and tears muffling his vision of him. "I can't move out on my own. Like fuck, I had a full panic attack just thinking of moving out." Dean pulls Cas to his chest. Through the already soaked flannel shirt, he can feel the hot tears drip from Cas's face onto his chest. He uses his other arm to wrap around his front, keeping Cas close to him.

"Of course you can. Dude, I just saw you jump off a sketchy looking rope into sketchy looking water earlier. The way I see it, you're braver than me. I wouldn't even touch that rope."

"It's not even the moving out. I lived in dorms the past two years. It's just moving so far away. And I'm going to have to do all this stuff on my own. I can't even go grocery shopping by myself, because of my anxiety."

"Hey, you're not doing it on your own, I'm going to be in the room next door. How about we make a deal? I'll do all of the grocery shopping for the first couple weeks while you get used to the town, and then maybe after you can come with me? And we'll work from there?"

The racking sobs had subsided and Cas can finally feel air pump in and out of his lungs without any hitches.

"That sounds okay."

Dean took Cas's face in both his hands and looked in his eyes. "Good, because I am not moving without you. This is our new adventure." They sit staring at each other, through the pounding of the rain and through the pounding of their hearts.

In Cas's mind he hears the beginning of Ed Sheeran's Bloodstream. Torturously, incrementally they lean towards each other, building sounds of Ed Sheeran's voice and complementing music. Cue tell me when it kicks in and a guitar riff accompanied by influx of drums. Dean leans all the way and hesitantly positions his lips on Cas's, waiting for Cas to back away. When he doesn't, Dean continues. He kisses Cas adoringly, in a chaste way, until he feels Cas nip at his bottom lip. He opens up enabling Cas to smoothly glide his tongue in.

Cas thought if every time even the largest of panic set in, this would be the best way to distract him and calm him down.

"Well that makes moving with you a much more exciting prospect." Cas says as he pulls away.

Dean laughs, rubbing his thumbs under Cas's eyes, trying unsuccessfully in the rain to wipe away any remnants of tears.

Cas looked down at Dean's wet clothes clinging to his body.

"We should probably go inside and dry off."

"Good idea, but first." Dean draws Cas's face in again and kisses him much more enthusiastically and needy. When he pulls away he lets out a breath, Cas is left with his eyes blissfully closed wanting more. "Okay, come on." Cas flutters his eyes open as Dean picks him up.

He can't help but feel so much better with Dean's arm wrapped around his shoulders and his arm wrapped around Dean's waist. Screw moving and going to school, Cas was ready to take on the whole damn world.