It was their last day in Florence and another day filled with Castiel dragging Dean to, he couldn't even believe there was more, art museums. He still didn't mind it, as long as Cas kept smiling he was happy. That night Balthazar took the family out to some fancy smancy restaurant, but Dean didn't complain. The food was good.

Once they were back in their room, Dean pulled out a shopping bag from under the bed and nodded for Castiel to come over.

Cas walked over wearily at Dean's mischievous grin, "What?"

Dean pulled out a bottle of wine from the bag, "Since, I was sick of this sweet cheap wine we keep drinking, I took it upon myself to buy some that was actually good."

Castiel laughed, "Dean, I don't think I would say the wine we've been drinking is cheap."

Dean shrugged, "Well, it taste like it."

Dean got off the bed and went over to balcony, "Come on."

Castiel followed him out and found Dean climbing on to the roof. There was an area that was wide and flat. Dean layed back on it. Castiel rolled his eyes at Dean's spontaneous midnight-drinking-wine-on-the-roof, but climbed up and layed beside him, nonetheless.

Dean took a swig from the bottle, "Yes, that is much better, not too sweet."

Castiel took a drink himself, "It's not too bad."

Dean shook his head, "You love it. Just admit it, Cas"

"Okay, Dean. I'll admit it, you have great taste in wine," Cas said sarcastically.

"See? Wasn't too hard," Dean turned his head and smiled at Castiel.

Castiel chuckled, "Dean, why are we up on the roof?"

"Wow, way to ruin the moment, Cas. I buy you nice wine, climb on top of the roof so we can enjoy the night and look at the stars, and you don't even appreciate it," Dean shook his head at Cas.

Castiel chuckled, "What? Are you trying to seduce me, Winchester?"

"Maybe," Dean winked playfully and if it wasn't so dark out he would've seen Cas blush.

They lay there in comfortable silence drinking the wine with Castiel occasionally pointing out constellations to Dean. The night grew cold, though, and they scooted closer to each other for warmth, their arms touching. At some point, Cas's hand had slipped into Dean's. Dean didn't comment, but Castiel saw the small smile. Again, Castiel was wondering when it had become so natural to do that, so casual, like they did it all the time, which is what it felt like now.

Castiel subconsciously started stroking his thumb across Dean's skin in soothing circles like he usually did when they held hands. Dean wondered if he even knew he did it.

"That's really comforting," Dean whispered barely audible without thinking.

Castiel didn't comment, but leaned his head on Dean's shoulder. His hair was tickling Dean's chin and Dean rested his head against his. Dean had never felt so content, even with the rough roof underneath him.

"Hey, Cas?"

"Hm?"

"Do you ever think about the future?"

Castiel shrugged, "Sometimes."

"What do you see?"

Castiel thought for a moment, "I see myself owning my own art studio."

"Oh, yeah?"

"And my best friend cooking cheeseburgers in the kitchen," Castiel added.

Dean grinned at that and chuckled, "I'm not some housewife, Cas. Why don't you ever make me burgers?"

"Because I'd burn the house down. Do you even remember the last time I tried?"

Dean snorted remembering, "Good point."

After a moment, Castiel asked, "What do you see?"

Dean pressed his lips together and in response to his silence, Cas lifted his head, "Dean?"

Dean was going to give him a witty reply, but he was taken aback by how close Cas's face was to his. He was only inches away. Dean could smell the wine off of his breath. He felt his heart rate pick up and could swear Cas could hear it. He glanced at Castie's lips and almost leaned in before he caught himself.

He hopped up and held out his hand for Castiel, "Come on, let's get some sleep. Early flight in the morning."

Castiel took his hand, still trying to process what had just happened, or almost just happened, again. They scrambled back into their warm room with the half drunk bottle of wine and passed out on their bed moments later.

Castiel woke up with a bolt and looked around the darkened room for what had jolted him awake. The moonlight shone through the open balcony, but there wasn't a breeze, so he wasn't awoken by the cold. He glanced at the sleeping Dean next to him and found his answer.

Dean was tossing and turning violently in his sleep. Cold sweat covered his face and neck. The bed sheets were in twist around his legs and Dean had the most pained and vulnerable expression Castiel had ever seen on him. It tortured Castiel to see Dean like that.

Castiel shook Dean's shoulder lightly, "Dean, you're having a nightmare."

Dean didn't wake, but he clutched onto Castiel's arm. Castiel heard him mumbling in his sleep. It was mostly unintelligible, but Castiel caught bits and pieces.

"It's so hot," Dean whispered, "The burns..."

"Dean," Castiel tried again, but Dean just gripped tighter on his arm.

"No, no, I have...go back. Mom,... please."

Castiel sighed, his heart aching at seeing Dean like this. It scared him a bit. What was he dreaming about? What haunted him so bad to make him in this state?

Castiel layed back down on his side and looked helplessly at Dean. He wasn't going to wake up, unless Castiel shook him awake and he didn't want to do that. He ran his fingers through Dean's hair soothingly with his free hand. It didn't stop Dean's pained expression or his inconsistent mumbling, but his body calmed and the grip on Castiel's wrist lessened. Castiel had an idea.

He pulled Dean into his arms where Dean rested his head on Castiel's chest. Castiel, then started to lightly stroked Dean's back. Dean's breathing eventually slowed and his pained expression eased. Castiel was thankful. Whatever was going through Dean's mind truly tormented him and Castiel wanted Dean to never think about it again. Dean wasn't one to show fear or cowardice, it's probably why it had frightened Castiel so much. Dean always put up a brave front, so Castiel didn't think Dean was afraid of anything, but obviously he had been being naive. Dean put up that wall for a reason, he wasn't born with it.

Castiel fell back asleep with Dean still cradled in his arms, worrying about for reasons he didn't even know. But with Dean so close to him, sleep came easily. Dean was right there, safe and sound.

Dean woke up with someone's arms wrapped around him. He willed himself to go back to sleep and didn't open his eyes. He nestled himself deeper into the other person and in response the arms tightened. There wasn't even the smell of sweat and sex in the air. It had to be best he had ever woken up. He was warm and comfortable. He didn't want it to end.

But at some point, Dean became a little more aware of his surroundings and where he was. He opened his eyes and peaked at the face above him. He was met with black stubble and dark sex hair that was tossed in every which way. It took a minute for his mind to register it was Cas and that it was Cas's arms wrapped around him. What? Had he crawled into Cas's arms in the middle of the night and Cas subconsciously held him?

Well, whatever had happened, Dean knew he should probably detach himself from Cas before he woke up and things got awkward real fast. But he really didn't want to. He stared up at Cas's sleeping face. He really was beautiful. Dean wondered how he hadn't noticed a long time ago. Dean rested his head back down on Castiel's cotton tee and enjoyed the moment a little longer. He was so damn comfortable, he contemplated just going back to sleep and dealing with whatever awkwardness occurred later. At the moment, it seemed kinda worth it.

But Dean didn't get to decide as the someone started knocking on their door. Castiel's didn't move an inch, though. But the incisive knocking would soon wake him up. "Dammit," Dean cursed under his breath before, regrettably, easing out of Cas's arms.

Dean tried not to be as grumpy as he was when he opened the door. But he couldn't help it. Whoever this was had interrupted a really good morning. Dean opened the door slightly as to not wake up Castiel.

"Good morning, Dean," Mrs. Novak greeted him, "Hope I didn't wake you?"

Dean plastered a smile on his face, "Oh, no, I was already up."

Rebecca grinned, "Good. Um, is Castiel awake?"

Dean glanced back into the room. Castiel was still in the same position he had left him. "No, not yet."

Dean looked back at Rebecca and she frowned. Dean asked her a little worried at her expression, "Is there something wrong?"

Rebecca bit her lip, deciding something in her mind. After a minute, she seemed to have decided something and she pulled Dean by his wrist into the hall. Dean was giving her a questioning look, when she nodded to the still open door. Dean closed it with a soft click.

"It's probably nothing to worry about, but..." Rebecca trailed off and her worried face was giving Dean anxiety.

"Just tell me what's wrong," Dean told her softly.

She sighed and shook her head, "I'm just being a worried mother. It's just that Anna went out last night and she hasn't come back. We leave in about two hours for Rome and it's not like her to be this late. I understand she's an adult but she's always been back early if when we're on vacation. But here it is nearly seven o'clock and she's nowhere in sight."

"Did you try calling her? Maybe she had too many bears and didn't want to drive, crashed at a hotel or something?"

Rebecca shook her head, "Anna doesn't really drink and she won't answer her phone."

"Um," Dean didn't exactly know what to do. Rebecca seemed like she was overreacting and Anna was an adult. But Dean knew his mom would react the same way if they were on a trip and he just disappeared. He tried to calm Mrs. Novak down.

"What if Balthazar went to go look for her? He knows the city pretty well," Dean suggested.

"Everyone went out for breakfast. I told Chuck I'd wait here for Anna. He replied by telling me I was being ridiculous, but..."

"Okay, what if - wait everyone left? What about me and Cas? You know we eat, too," Dean joked but still found it odd. Everyone usually went out together.

"Oh, um," Rebecca smiled a little, "Michael came by to get you, but you wouldn't answer the door."

"Oh," Dean replied not really believing it. What? Did Cas's family not like him after all and decide to ditch him along with Cas?

"Then," Rebecca continued, "Gabriel barged into your room and...well, he decided you guys looked...comfortable and didn't want to wake you. He actually said something else, but I'm not repeating it."

Dean blushed remembering the position he had woken up in. He was never going to hear the end of it from Gabriel. Rebecca didn't meet his eyes and actually avoided looking at him at all. Dean suddenly became aware he was dressed in just a tee and boxers. His blush deepened.

Dean rushed to escape the awkward atmosphere, "So, anyway, back to Anna?"

"Yes, I was actually hoping Castiel would go look for her. He knows the city better than I do."

Dean glanced back at the bedroom door with the adorable sleeping Cas behind it. He turned back to Rebecca, "Well, I could go look for her if you want?"

Rebecca looked at him with surprise, "Dean, I don't want to seem to be rude, but I don't know. You don't know the city that well. What if you got lost?"

Dean shrugged, "I know it well enough. Cas and I went out the other night and it feels like he's dragged me to every museum. I won't go that deep into the city, but it's better than sitting around worrying what happened, right?"

Rebecca gave him a grateful smile, "Do you want me to go with?"

"Nah, I'll be fine."

Rebecca pulled him into a hug, "Thank you, Dean."

Dean snuck back into their room and grabbed a pair of jeans off the floor, tugging them on. He grabbed his cell phone and with one last look over his shoulder at Cas walked out the door.

Castiel woke up to an empty bed feeling cold. Dean was no where in sight and the spot next to him wasn't even warm. Castiel checked the bathroom, but the light was off and the water wasn't running. Castiel got dressed and walked downstairs. He guessed Dean had gone down for breakfast and didn't feel like waking him.

But Dean wasn't there, no one was there. Where had everybody gone? Castiel sauntered around trying to find someone in this over-sized house. After what seemed like forever, he heard voices coming from the foyer.

"Come on, Balthzy, that waitress-"

Castiel turned the corner to find mostly everyone coming in, he assumed from breakfast. But he didn't see Dean. He looked for Anna to ask her, but she wasn't there either.

He walked over to Gabriel, "Is Dean with you?"

Gabriel looked at him puzzled, "Um, no?"

"Didn't you just come from breakfast, though?"

"Yeah, but he didn't come with us. You two looked so damn intimate this morning, arms wrapped around each other, I didn't want to wake you," Gabriel winked.

Castiel blushed slightly, but was too worried to really care what his brother had seen. Where the hell had Dean gone?

Gabriel caught on, "What? He wasn't there when you woke up?"

"No."

Gabriel thought for a minute, "Ask Mom, she didn't go with us. She wanted to wait for Anna."

Castiel looked at him confused, "Anna? Why? Where's she gone?"

Gabriel shrugged, "That's the thing, we don't know. She left after dinner last night, but hasn't come back. I told Mom not to worry, but you know how she is."

Castiel nodded and went off to find his mother. After she explained where he was, Castiel's worry grew more. Of course Dean would think a few days out on the tourist area of Florence would be good enough to run a search party.

"Why didn't you wake me to go look? Dean has the worst sense of direction and would never ask someone for directions. He's probably lost somewhere in Florence by now."

Rebecca waved her hand, "Castiel, honey, I'm sure he's fine."

"When did he leave?"

"Seven," Rebecca answered calmly as she folder clothes into her suitcase.

"It's nearly eight thirty!"

Rebecca gave him a confused expression, "Castiel, it's fine. If they're not back by nine, we'll just depart later. It's our plane."

Castiel rolled his eyes, "I'm not worried about the damn plane. How could you send someone who hasn't been in Florence for not even three days to go search the city for someone?"

Rebecca was taken aback by Castiel's tone, "He offered. He said he wouldn't go deep in the city. Castiel, I know you're worried, but I'm sure he's fine. Call him if you don't believe me."

Castiel pulled out his phone and dialed Dean's number. He probably was overreacting and if he was he was sure he got it from his mother. As it rang, though, Castiel's worry didn't lessen. The call went to voicemail. Something tugged at Castiel's stomach from inside and twisted unpleasantly. Something was wrong, he just knew it. Castiel tried Dean again. No answer. Once more. No answer.

"He's not answering," Castiel told his mother.

Rebecca looked up from her packing and looked worried for the first time. She walked over to Castiel, "Well, maybe he didn't take his phone?"

Castiel shook his head. It hadn't been on the bedside table when he left the room.

"Well-"

Rebecca was caught off by Castiel's phone ringing. He answered immediately with a wave of relief, "Dean, I was starting to worr-

"Castiel!" Anna's voice cried on the other line.

"Anna?" Castiel felt his chest constrict at her voice.

"Castiel," Castiel could barely understand her between her broken sobs, "I-I'm so sorry, Castiel."

"Anna, what's wrong? Did Dean find you? Are you okay?"

"He-he - Castiel, this is all my fault," Anna continued to cry on the other line.

"Anna! Tell me what happened," Castiel tried to remain calm, but he just couldn't, not when Anna was talking like that.

"It's Dean," Anna tried to stable her breathing, "He's in the hospital. Cas, it doesn't look good."

Castiel felt his heart stop and he was paralyzed as Anna spouted the address of the hospital. But as soon as she finished his phone fell to the floor and he sprinted for the front door. His mother called after him sounding panicked and asking what was going on, but he didn't stop. He found the keys on the table and not twenty seconds later he was pulling out of the driveway. He sped all the way to the hospital, probably breaking several laws. But he didn't care. All that bounced around his head was It doesn't look good. It doesn't look good. over and over. Tears threatened to pour over as Castiel tried to tell himself Dean would be okay. Because if he wasn't, how would Castiel ever be?

- Thirty Minutes Earlier-

Dean strolled down the sidewalk, wondering how he was ever going to find Anna in this big ass city. Dean didn't want to tell her mother, but maybe Anna had hit off with someone last night and was just having a slow morning. Dean almost gave up and headed back to the car, when he caught a glimpse of red hair.

He backtracked and looked through the coffee shop window again. There she was. In a coffee shop with her head in her hands. Dean chuckled to himself before walking in.

He walked over to her table, "I can't believe I actually found you."

Anna looked up startled at him and winced at the movement. She groaned and put her head back in her arms on the table. Dean knew the look. She was hungover.

He sat down in the seat beside her and decided to tease her, "Oh, Anna-banana, you look like hell."

She didn't look up but flipped him off, "How did you find me? What are you even doing here?"

"Your mom," Dean stated simply.

"I'm a grown woman if I want to stay out all night I can."

"Yeah, I know. She knows that, too. She's just worried."

Anna ungraciously lifted her head up and dived into her coffee. Dean chuckled at her smeared makeup and barely combed hair. She glared at him.

"Someone got lucky last night," Dean wiggled his eyebrows at her.

Anna smiled, "I wasn't even going to drink that much, but then I met this guy and we hit it off. Oh my god, he is so flexible. He could-"

Dean put his hand up, "No, no, no, I don't want a detailed story."

Anna laughed, "Then, don't tease me, while I'm hungover."

"Your mother said you didn't drink."

"Not that much," Anna shrugged and added with a grin, "Usually."

Dean shook his head at what that smile implied, "Don't want to hear it. You're my boyfriend's sister. I don't want to hear about your sex life."

Anna rolled her eyes, "I was going to order something to eat. Want anything?"

Dean stood up, "Sure, just get me anything. I'm going to call Cas. He should be up by now. He's probably wondering where I am."

Anna walked to the counter, while Dean stepped outside. The sidewalk was more crowded now and loud, so Dean hovered near the edge of the store near an alley. He pulled his phone out, only for it to be snatched out of his hand.

Dean looked up angrily, "What the hell!?"

He was welcomed with a hard shove against the wall. Dean barley had time to understand what was happening before two fist socked him in the stomach. He doubled over and dropped to the floor. He couldn't breath and there were voices above him screaming something he didn't understand. Gravel flew at his face as well as kicks that felt like they were being directed at his whole body. Dean was usually a good fighter and he could probably kick these guys asses if he hadn't been caught off guard, but he was and now he was starting to see black.