A/N : I'm currently suffering from a severe case of flu, and this chapter tried to run over me so I had to cut it in two parts, this has not been my week at all. But no worries, I'll finish the next chapter as soon as I can.

Where Do We Draw The Line

Chapter 6

Castiel tiptoed to his black sling bag that he had owned ever since he was sixteen. He took out a small thermos filled with hot coffee and took filled a mug for himself and grabbed his leather jacket, before sneaking to the balcony and lighting a cigarette. He leaned to the railing and looked at the view beneath him. There wasn't much to see besides the city lights since the clock was closing on four a.m, but the cool air was soothing and the massive dots of light were beautiful in their own way. Castiel yawned and took a long sip from his coffee to fight off the tiredness he felt. He still had five hours to go before he would head back home.

Castiel glanced through the large window to make sure Ruby was still asleep on the large bed, he was glad to see she was, he really didn't need her to wake up. He cursed his inability to sleep during a job, even when it meant he would have to stay up all night doing nothing else but stare into the darkness of a room. Castiel finished his coffee and cigarette without any hurry and reminded himself that the paycheck he got was worth the tiredness in the morning.

After ten minutes or so Castiel sneaked back into the dim hotel room, put his jacket aside and crawled back to the bed. Ruby shifted slightly in her sleep and Castiel froze for a moment. He didn't relax until Ruby had settled back down and he had made sure she was still asleep. He stared at the ceiling and allowed himself to get lost in his thoughts. He wondered how his family was doing for a second, before quickly shifting his thoughts to the very slowly closing evening. Dean had promised to pick Castiel up from the 53rd street, before they would head to Gem's.

Castiel exhaled quietly, he wasn't sure if he knew how to go out with friends anymore. Not that he didn't have friends who liked to grab a beer with him, but Dean was a new acquaintance and Castiel really didn't want to blow the whole thing off by suddenly snapping into his professional mode. He used the other person he had created for work instinctively as a defense mechanism, and he didn't always even realize he had changed his behavior from Castiel to Angel and be what was needed, not who he truly was. This instinct had gotten Castiel suspended from college, where one of the older students had continually picked on him and pushed him around to the point where Castiel had finally snapped and broken his nose. When Castiel thought about that situation now he realized he had needed someone to help him and make the older guy stop and leave him alone. He had gotten what he needed, and now he hated it.

Castiel hoped everything would go well with Dean, and suspected he should probably stop worrying and just take the evening as it was, just a nice evening between friends, nothing else. Castiel frowned into the darkness, he wasn't quite sure why he was suddenly so nervous about all of this. It wasn't like he hadn't ever been out with someone he barely knew before. Ruby mumbled something Castiel couldn't comprehend, but it snapped him out of his ruminations.

Four hours passed very slowly. During those hours Castiel helped himself another cup of coffee and brushed his teeth after it, but finally Ruby started to wake up. Castiel turned to his side and fixed a pleasant smile on his face as Ruby slowly opened her eyes. She stretched herself like a lazy cat, eyes still half closed.

"Morning," Castiel said softly and brushed the unruly hair from Ruby's face. She smiled contently and buried herself deeper to the soft sheets, mumbling something that sounded vaguely like good morning. Castiel gave Ruby all the time to wake up as she wanted, but kept a rather close eye on the time because all he really wanted at the moment was to go home and sleep all the way to the next century. He refused to stay there any longer than necessary.

"You think I could get fries for breakfast?" Ruby's voice was muffled by the pillow, and Castiel had to take a moment to figure out what she had said before answering.

"I can call the room service and ask," he offered and Ruby turned to look at him with grateful eyes. She reached out and ruffled Castiel's already messy hair.

"I'd kiss you but I think I'd better brush my teeth first. But you're an angel, you know that?" Ruby said and Castiel smiled, holding back a comment that most definitely did not go well with the current situation. He got up and got Ruby the fries she so desperately wanted.

An hour later Castiel said his goodbyes to Ruby with a charming smile and a hug, before he grabbed a taxi and headed home to get some well earned rest. Castiel dozed off in the back seat of the taxi, and when he finally made it to his apartment he kicked his clothes off and jumped to the bed. He gladly closed his eyes and fell asleep within seconds.

Dean felt bad for Lisa, she had what she called the hangover of the century, and there was very little he could do to help her. Dean fought back the need to tell Lisa she should get a greasy pork sandwich or something similar. He was fairly certain he would suffer greatly if he did or said anything to make Lisa feel any worse she currently did. Dean filled a glass of water to his wife, grabbed his full coffee cup and headed towards the living room where Lisa laid on the couch. She looked miserable under the creamy colored comforter with her tangled hair and pale face. Dean offered the water to her and Lisa took the glass with slightly shaky hands and a grateful smile.

"You sure you'll be okay if I go out today?" Dean asked with a soft tone as he crouched next to his wife and petted her messy hair gently. Lisa drank the water before turning towards Dean and smiling slightly.

"I'll be fine in couple of hours," Lisa assured and Dean gave her a small nod before he got up and went back to the kitchen to get himself something to eat. He tries not to think the quickly closing evening too much as he scrambled through the insides of the refrigerator. Dean had told Lisa he was meeting up with some friends, it had seemed like a good answer, informative but still vague.

Dean quickly fixed himself a cheese sandwich and as an after thought grabbed the aspirin bottle from the shelf before going back to the living room to see if Lisa needed anything else. She shook her head and complained weakly about the smell of Dean's sandwich. Dean laughed a little at that, but left Lisa with her water, aspirins and the remote for the television.

Twenty minutes later Dean took a long shower and spent countless minutes trying to make his hair obey his will before he wandered to pick up the clothes he would wear. He tried to appear as though it didn't really matter what he was wearing as long as it was comfortable, when the truth was he was rather terrified of picking up something that didn't look good on him. Sam would probably tell him he was acting like it was his prom night, and Dean had to stop going through his shirts for a moment to wonder where the thought had popped to his mind. He quickly shook it off and decided to go with a simple dark shirt and slightly worn out jeans. He would grab his old leather boots from the closet in the hallway downstairs.

At two o'clock Dean stopped pacing around the house and picked up his phone. He dialed Castiel's number and went to check on the Impala as an excuse to get some privacy, Lisa was eyeing him curiously and he really didn't need the attention at the moment. Dean waited for what a rather long while before Castiel picked up. Dean raised a confused eyebrow when he heard ruffling followed by a heavy thud and some cursing before Castiel's clearly pained hello.

"You okay?" Dean asked, concern shining through his voice.

"Yes. I'm fine, you just woke me up, " Castiel said hurriedly, and Dean had a creeping suspicion that he had fallen from bed. He forced the amused grin from his face and concentrated on the conversation.

"Do you still want me to pick you up at four?" Dean asked after he had managed to get himself under control.

"Of course. I'll be ready by then," Castiel promised and Dean nodded before realizing Castiel couldn't see him.

"Okay. I'll call you before I leave so you'll know where I'm going," Dean said and Castiel agreed to this arrangement. They ended the call and Dean didn't even try to stop the wide smile making it's way to his face. He gently patted the hood of the Impala as he spoke to the car.

"We're going out today sweetie." Dean spent few moments checking the tire pressure and oils of the old car before going back to the house. Lisa was waiting for him in the kitchen, pealing an apple with a great deal of concentration.

"Who were you talking to?" She asked without lifting her eyes from the apple when Dean entered the room.

"No one. I think I'm gonna have to buy new oil for the Impala, I just checked the bottle I have and it's almost out," he said, quickly changing the subject. Lisa took a bite of the apple an regarded Dean with a serious expression.

"Sometimes I think you care more about that car than me," she said with a fake hurt in her voice, and Dean gaped at her in awe.

"How did you find us out? Was it the car wash we took or the new windscreen wipers?" He said with an exaggerated amazement. Lisa laughed and pulled Dean into a quick kiss. Dean wrapped his arms around her and buried his face in Lisa's dark hair. He did his best to let Lisa know how much he loved her without having to say the actual words. Lisa seemed to understand him as she squeezed Dean as hard as she could.

"Okay, I'm still not feeling all that good," Lisa said finally and dislodged herself from Dean with a final squeeze.

"You just rest today, okay? And remember that you can call me any time you want," Dean reminded Lisa with a stern voice and ran his hand tenderly through her hair. Lisa nodded in agreement and left the kitchen after giving Dean a chaste kiss simply because she could. Dean looked after her with a hint of a smile playing on his lips, before he shook himself out of his thoughts.

Castiel laid on the bed, rubbing his painful hip and waiting for his alarm to go off. He couldn't believe he had actually fallen from the bed, he wasn't even sure how it had happened. One moment he was turning around to answer the phone, and the next he was lying flat on the floor fully awake and in pain. The alarm went off seven minutes after the cll with Dean had ended and Castiel shut it with more force than necessary before he got up and more or less limped to the kitchen to make himself a late breakfast. Castiel fixed himself a sandwich while he waited for the coffee to drip.

Castiel quickly went over his plan for the day, he would get a shower, eat something, get dressed, and leave for the evening. It was an simple plan and Castiel liked it because of this. He didn't need any big and complicated plans for getting ready for a night out like he had heard some people did. Castiel poured himself a cup of coffee and drank it quickly, almost burning his tongue in the process, before he left the bright kitchen to grab a shower. Castiel didn't hurry as he took his clothes off and folded them carefully, before stepping into the shower stall and turning on the water. A cold steam hit Castiel's face and he started before quickly turning the heat up.

Castiel finished the shower quite quickly, shaved and battled against his unruly hair with very little success. Castiel gave up the battle after it came apparent he could not win. He put on his clothes and stretched his arms lazily. All he had to do now was to eat the rest of the risotto he had in the refrigerator. Castiel had never been one to brag, but if he had to pick one thing he was really good at, he would have picked cooking. The time had passed without Castiel noticing it, and soon Dean called to let him know he was ready to leave. Castiel told his friend he would get to their agreed meeting point.

The weather was a little more chilly than Castiel would've liked, and he pulled his jacket tighter around himself and hastened his step. He reached the street corner he had agreed to meet Dean earlier than he had anticipated, and he spent two minutes anxiously shifting his weight from one feet to another before he spotted Dean's car. Castiel felt a smile making it's way to his face, and he didn't bother to fight it as he climbed into the car and greeted Dean. Dean looked at him with a cheery grin on his face.

"How you've been?" Dean asked as he pulled the car back to the road Castiel settled in his seat.

"Okay. I had a little catching up at work to do but it's good now. And you?" Castiel answered impassively and turned his full attention to Dean, who considered his answer as he concentrated on driving in the busy street.

"Fine. My best friend tried to drag me to Vegas," Dean smiled fondly, and Castiel caught himself thinking how nice the smile looked on Dean. He shook himself out of his musings quickly.

"So what are we going to do now?" He asked lightly, making Dean shoot him a bemused look.

"Um, we could go for a coffee?" He suggested with a clearly hesitant undertone in his voice. Castiel was quick to nod in agreement, and Dean seemed to relax at this. Castiel told Dean to take the left turn on the next intersection and directed him to the same place they had been in the last time they had met. Dean parked the car while telling Castiel about his genius little brother with great deal of pride in his voice and Castiel found himself wishing someone would talk about him as highly.

"Shit, I'm sorry. I'm rambling, aren't I?" Dean apologized when they stepped on the sidewalk, but Castiel dismissed the whole thing with a wave of his hand.

"I like hearing about your family," he assured Dean and leaded them towards the café. Dean contemplated him for a few seconds with a small smile pulling at the corners of his lips.

"How about you. You have any siblings?" Dean asked offhandedly, making Castiel stumble slightly. He corrected himself hastily and gazed at Dean nonchalantly.

"I had a step-sister, there's really nothing to talk about it," Castiel informed Dean and wished he wouldn't push the matter. Dean studied him with a great deal of curiosity for a while, before dropping the matter with a nod. Castiel gave him a grateful, but barely there smile and reached for the door handle. He held the door for Dean and pulled his thoughts away from his sister and directed them all to Dean, since he was the one who would keep him company that evening. They ordered their coffees, and Dean insisted on them getting a slice of the apple pie on display. Castiel took one look of the determined manner Dean was staring at him and lifted his hands in a sign of surrender. He knew how to pick his fights, and this one was clearly one he could never win.

Dean took the pie and the coffee to his hands with a triumphant grin and sauntered towards the table they had sat the last time so that no-one else would get it while Castiel payed for his own coffee. Dean had tried to pay for his coffee too, but Castiel had stopped him. Their argument had earned them a disturbingly knowing grin from the woman behind the counter, and Dean had finally given to Castiel's wishes. The smile on the cashiers face never faded.

"I'm buying you a drink tonight," Dean declared the moment Castiel sat down. Castiel gave him a puzzled look.

"Why?" There was no other way for him to ask clarification for Dean's apparent need to pay for his share too. Dean stopped what, to Castiel, seemed to be a careful analyzation of the apple pie.

"Why not?" Dean countered and Castiel squinted his eyes in frustration. This was going to be difficult a conversation.

"Because you don't have to. I didn't ask you to and against that woman's believes we're not dating, so you're not obligated to do so," Castiel tried to throw a joke into his otherwise stern respond. Dean lowered his gaze and sunk his fork to the pie, and took a large bite out of it. Castiel got the impression Dean was trying to buy time for himself, so he took a long sip from his coffee and waited. Finally Dean gave up and faced Castiel's persistent stare.

"Just so you know, I hate chick flick moments," he warned Castiel, who only deepened his stare.

"I don't care," he stated bluntly, and Dean looked at him with surprise written all over his features. Castiel simply cocked his eyebrow to show how unimpressed he was at the moment. Dean shook his head and muttered something under his breath that Castiel didn't catch, before taking a deep breath and leveling his gaze with Castiel's.

"Fine, I feel slightly bad because it took me nearly two weeks to call you. I mean, I was the one who brought the whole 'we should meet again' thing to the table," Dean explained, and Castiel could see he was uncomfortable with the situation. For a second Castiel considered pressing the matter further, but decided to let it drop in the name of new friendships.

"Okay, explanation accepted. If it will make you feel any better you may buy me a drink later," He said with a light tone, earning himself a silent thank you from Dean. They sat in a companionable silence for a while. Castiel observed Dean as he ate the pie in front of him with closed eyes and a blissful expression.

"This is amazing," Dean managed to gasp between the mouthfuls. Castiel just smiled, feeling a sudden surge of affection sweep through him. He took a quick sip of his coffee to distract himself and lowered his gaze to the pie wondering if it was in fact as good as Dean let him think.

"Here, you need to taste this," Dean decided, snapping Castiel out of his thoughts. Dean offered Castiel a forkful of the pie with a spark in his eyes. Castiel wasn't sure if this was very good idea, but he leaned forward anyway and allowed Dean carefully guide the fork into his mouth, never breaking their eye contact. He didn't have time to put much thought to the intimacy of the whole situation before the taste of the apple pie forced him to choke a moan. Dean was grinning at him triumphantly as he finished the pie before Castiel could claim any more of it for himself.

"You're mean," Castiel finally said without actually meaning it. Dean chuckled and took a sip from his coffee.

"You're lucky I even shared my pie. that doesn't happen too often," he told Castiel, who did his best to understand just how important this whole situation was. He was fairly certain he failed at his attempt.

"How come you know almost everything there is to know about me and I don't know a thing about you," Dean said suddenly, looking rather baffled by the fact. Castiel felt a sudden rush of terror run through him as Dean regarded him with new curiosity. He quickly decided it was probably for the best to tell Dean something to satisfy his curiosity.

"I've studied art history, I have two friends, another is a writer, or at least he tries to be. And Pam is conducting a research on the psychological aspects of someones sexuality and how it manifests in their behavior, or something like that, she's a psychologist, one of those academic professionals, you know. She does some clinic hours too but right know she's concentrating mostly on her work," Castiel left out the part where Pamela had nearly tied him down and tortured him so hat he would answer her questions in the early phases of her study. Chuck had later offered Castiel a beer and told him he had had the same treatment.

"That sounds interesting," Dean noted and urged Castiel to carry on. When the younger man merely lowered his eyes to his nearly empty coffee cup Dean left out an annoyed huff.

"What do you do for living?" Dean asked patiently. Castiel contained the need to kick the other man under the table and went with the first answer that came to his mind.

"I'm self employed. Last year I spent two months in Europe as a sort of an assistant to this really big artist. We went from one art show to another and it all ended with the fashion week in Paris," Castiel was pleased with his answer, especially since it was true. He did, however, leave out certain parts, like how he had gotten his apartment in the deal, and how the particular french artist had a quirk for having sex anywhere but in the bed, unless light bondage was featured. Castiel smiled quite fondly at the memory.

"Got a girlfriend?" Dean's voice forced Castiel out of his reminisce. It took him a split second to realize what Dean had said, and when he did he sniggered and shook his head in amusement. Dean gave him a confused glance before he seemed to come up with an thought. Castiel looked at him with a hint of dare in his eyes, wanting to see if Dean would ask what Castiel thought he might. Finally, after what seemed like an hour, Dean collected himself and asked the question.

"Got a boyfriend, then?" There was reservedness in his voice, as if he was expecting Castiel to get mad at him.

"Not for a while, no. People don't normally stick around me for that long," Castiel told, without any menace in his voice. He was grateful Dean had had it in him to ask a question most people would probably find offensive. Dean nodded slowly and eyed him with an unreadable expression. Castiel almost expected Dean to bolt from his seat, but it never happened.

"Maybe if you weren't allergic to straight answers people would probably be asking you out all the time. I mean, pulling information from you is pretty damn hard," Dean remarked humorously. Castiel chuckled and decided to put double the effort to not blowing this whole thing up.

They ordered another round of coffee and decided to head to Gem's after they had finished their drinks. Castiel let Dean pay for both coffees and barely contained a smile when Dean straightened his posture slightly while giving his credit card to the cashier. When they had their coffees in front of them Castiel asked Dean to tell him more about his car. Dean bursted into carefree laughter and gave Castiel a mischievous grin, before reciting the whole history of the Impala with every single detail he could remember. They stayed there until the woman behind the counter announced they needed to close up for the day. Castiel was genuinely happy as Dean proclaimed he could drink Castiel under the table at any given time, and they set it as their goal to see if this was true right away.

A/N : Facts about this chapter :

1) I concidered writing an essay on psychological aspects of sexuality and how they manifest themselves in behaviour, but I drobbed in order to write about violent behaviour and its aspects and reasons.

2) Dean telling Castiel he's allergic to straight answers comes from Deans comment to Castiel in In the Beginning (04x03).