Two months later

"Dean I'm telling you right now that they'll notice!" Sam hissed at his brother.

Dean squinted as he looked into the restaurant through the large window. "No they won't, I'm getting better at this."

Sam crossed his arms; he didn't want to get into a fight while there were people all around.

"You're going to fall or end up in the wrong spot and everyone is going to freak out. Then we'll have to make a run for it."

Dean turned his temporary green eyes at Sam. "Don't have any faith in me Sammy, huh?"

"I do but just last week you fell in that fountain and almost gave that lady a heart attack!"

Dean rolled his eyes, yes he had missed the park bench he was aiming for but it had been right next to the fountain. It wasn't his fault that the lady had sat down on the bench right before Dean went to teleport. He had panicked and that was why he ended up in the fountain.

"You know that wasn't my fault Sam! I might not be able to teleport anything but small distances, but I've got this under control now. Just watch."

Dean stared at the empty table that the busboy had just cleaned. He focused in on the seat to the right and a few seconds later he felt that rush of air he always experienced while teleporting. It was kind of scary but exhilarating at the same time.

Dean looked around and smiled when he saw that he had teleported so he was sitting at the table, exactly what he had been going for.

Hah, take that Sammy. His little brother owed him one.

Dean heard a loud gasp and he turned to see one of the young waiters staring at him in shock and confusion. Oh boy, this would be fun.

Dean sent the kid an annoyed glare. "What are you staring at, kid? How about having some manners and asking me if I'd like something to drink? The service here sucks."

The boy, still staring at Dean in total unbelief, simply nodded. "Uh…y-yeah, sir. Wh-what would you like t-to drink?" he stuttered.

Dean leaned back in the booth and crossed his arms behind his head. "I want the most expensive beer you have. And it better be quick or I'll be having a talk with that manager of yours."

The kid's hands were shaking and as he nodded and turned, he ran right into Sam, who was coming over to sit at the table. He floundered and dropped his notepad. As he looked up to see who he ran into, his eyes widened at the sight of Sam's muscles and height.

"I'm…I'm so sorry sir!" The kid was clearly panicking now. He grabbed his notepad and quickly began to skirt away as Sam sat down.

"Hey, kid! Hey!" Dean called out even as Sam glared at him.

The waiter jumped and turned quickly but reluctantly. "Yeah, sir?"

"Are you going to ask if my little brother is thirsty at all? Or are you just gonna run into the guy?"

"Dean!" Sam hissed and turned kind eyes on the boy who was now hurrying back.

"I'm so sorry! Is there anything I can get you, sir?"

Sam sent a sweet smile the boy's way. "It's no problem. Just a water is fine with me."

The kid nodded hurriedly and then practically ran towards the kitchen.

Sam immediately turned his angry eyes on his brother. "Dean! Are you tormenting that poor kid? He looks scared out of his mind!"

Dean shrugged. "Hey, he was already freaked when he saw me magically sitting here out of nowhere. I figured I may as well have fun with him."

Sam knew he was lucky that Dean wasn't killing or hurting anyone, just messing around and being obnoxious. But it still got on his nerves sometimes. "At least you teleported where you wanted and didn't land on the table like at Bobby's."

"I told you I could do it, you so owe me for not believing in me."

Sam rolled his eyes. "Yeah, I was wrong. But I won't owe you anything if you keep acting like a jerk to this…"

"Hello boys."

Sam jumped and even Dean looked a little taken aback by the sudden appearance of Crowley sitting next to Sam.

"What the hell are you doing here?" Dean asked. He noticed how Sam scooted closer to the wall to get further away from Crowley. "You always make us come to you most of the time or you call."

"Yes, well I figured I needed to tell this to you two imbeciles face-to-face to make sure you understand. I've located Samhain and found out about his plans since you two are too dense to figure it out yourselves."

"Really?" Dean asked, intrigued. "Then where is he?"

"If you let me finish, I would have gotten to that part, you bafoon," Crowley hissed. "Lilith had him laying low for a while. But now she sent him to a small town in Kentucky to kill all the citizens there. It was her idea to have him go from town to town destroying everyone to draw you two out."

"Do you think she's going to be there?" Sam asked.

"Of course not! She's drawing you there so Samhain can kill your pigheaded brother. She thinks that if he kills Dean, you'll want revenge and kill her, thus freeing Lucifer...blah blah blah..."

"Of course he wants to kill me, what else is new?" Dean rolled his eyes. "Okay, when do we have to be there?"

"Oh, tomorrow night...around midnight."

"Tomorrow?" Sam asked with wide eyes.

Dean shook his head angrily. "We can't do it by then! He's bound to have a bunch of demons with him and we'll need backup! We haven't been able to get into contact with the angel for weeks!"

"Then it's a good thing I knew you two would be incapable of doing anything by yourselves. I came prepared with backup for your incompetent selves."

Dean shook his head yet again, his eyes determined. "We're not working with one of your random demon cronies. Remember that one that tried to kill me in your mansion?"

"Relax, you fool! I've got someone you've already worked with. She's not too thrilled about helping out but it's a better alternative than me killing her."

Sam looked over at his brother who looked just as confused. "She?"

Crowley snapped his fingers and suddenly a very familiar blonde young woman appeared beside Dean.

Dean turned, just as startled as Sam. "Ruby?"

Ruby folded her arms over her chest and glared at Dean. "Obviously. Why don't you state the obvious some more, Dean?"

"I'd shut your mouth if I were you, bitch," Dean shot right back.

Crowley clapped his hands once and smirked at Sam's uncomfortable face. "Great, glad you're getting reacquainted. I'll be going now, and I better hear some good news in two days time." The demon shot Sam a menacing glare that caused him to shiver and then, the seat next to him was empty.

"Oh right, 'bitch'," Ruby was talking to Dean. "That's so unique. Can't think of a more clever insult? Why don't you use your brother with the college education, he should be able to come up with something to add to your limited vocabulary."

Sam saw the waiter appearing again out of the corner of his eye. "Guys, shut up!"

The waiter approached the table, looking confused as he placed Dean and Sam's drinks down. "There was man here…Where...where did he go?" The boy stuttered, looking around for Crowley. He looked even more spooked at the sudden appearance of Ruby next to Dean.

"He left. What took you so long?" Dean narrowed his eyes.

The boy took a cautious step backward and Sam glared at his brother. "I….well…I accidentally spilled the first drinks…."

Dean rolled his eyes and sighed over-dramatically. "Of course you did."

"I…I'm really sorry sir…I'll give them to you free of charge."

"Now that's more like it. Good, now I won't have to report you to your manager," Dean said and Sam had to bite back an angry retort. The kid gave Dean a doubtful look and Sam didn't blame him, Dean had been acting like an ass.

Dean held his hands up. "Hey, I just like messing with people. Now why don't you ask us what we want to eat and get her a drink? I'm starving, and you're taking forever."

The kid seemed more relaxed now that he knew Dean was just a jerk and not some crazy person and he quickly took their orders.

As soon as he left Dean turned back toward Ruby. "So you managed to get out, huh? That's a shocker. Or did Crowley pull your sorry ass out?"

"Oh, you mean like how he helped you get out? No, he didn't. I got out all by myself before he found me and dragged me here. I can actually do things on my own, unlike you."

"Really?" Dean leaned closer to her. "You got out all on your own, huh? I seem to remember you getting a little help…and I think that demon that helped you was me. Don't tell me you forgot the fun times we had downstairs…"

"Oh, believe me, I haven't. If there's one thing you're actually good at, it's sex."

Sam held his head in both hands and groaned loudly. "I don't want to hear about how you two…did it. Can we please change the subject?"

Ruby turned her attention away from Dean finally and smirked across the booth at Sam. "Almost forgot you were there Sam. You look better than I thought you would. Dean-o here was spazzing out down in Hell, worried sick about his little brother, and thinking up all kinds of scenarios of horrible things that could have happened to you."

"Shut up," Dean growled, clearly embarrassed.

"Just saying it as it is," Ruby shrugged and then turned to address Sam again. "Gotta say, I'm impressed with you two. Dean, for somehow keeping that same dedication for you and therefore keeping some bits of humanity intact. And you…" Ruby shook her head in awe at Sam. "You were so reluctant to become involved in anything with those powers of yours. And here you are, gladly accepting your demonic brother and from what Crowley's told me, you're even drinking his blood."

Sam shrugged once more. "I trust Dean to keep me safe. You should know that. We've got this blood thing under control."

Ruby nodded. "I can see that, you're not all strung up and bursting with power like I thought you'd be. The power's there all right, but you've got a handle on it, it's brewing under the surface but it's not taking control on you."

"That's because I'm an awesome brother and I know what I'm doing," Dean spoke up as the waiter came and placed down Ruby's beer and quickly walked away. "Now stop interrogating my brother."

"I'm not interrogating him Dean. Do you even know what that word means? Oh wait…"

"Enough!" Sam sighed and ran a hand through his hair. He was going to have his hands full with these two. "I know Crowley sent you here, but why can't you just leave? Dean said you wanted to stay as far away from this mess as possible."

"Why do you think? Crowley is keeping watch on me. If I don't help out, he's going to track me down and kill me. So we're going to find this demon and send it to Hell, and we're going to do the same as Lilith. We all want the same thing and we're going to have to work together. We can't make the same mistakes we did last time." Ruby pulled down her shirt sleeve to show a body-lock symbol, the same mark that Dean had branded all over his body, right on her upper arm. "Lilith isn't going to possess me this time. Not that it matters much for you two, you can both see my soul now so you'd be able to spot that it wasn't me right away."

Ruby paused and looked at Dean. "Which, speaking of souls…I can't see yours Dean. Nice trick there, if I didn't already know you were a demon, I wouldn't have a clue. I was a witch and I haven't even heard of this one. You're going to have to tell me that spell."

"Not in this lifetime, sweetheart." Dean smirked.

"Oh, how sweet, and here I was thinking that our sexual adventures didn't mean anything to you. So glad I was wrong."

Sam cringed and wished he had the power to make demons shut the hell up.

Both Dean and Ruby slept for most of the ride, much to Sam's delight. When Dean wasn't sleeping, he was driving and there was unusual awkward silence between the brothers. It wasn't based on being uncomfortable with each other, but from having a tag-along demon riding in the backseat.

When they arrived at the city Samhain was set to destroy, they chose a motel and booked two rooms. There was no way Ruby was going to stay with them.

"I wouldn't want to stay in a room with you two pigs anyway." Ruby rolled her eyes as they stepped out of the lobby.

"And I wouldn't stay in the same room as a bitch." Dean glared at her and Ruby stared right back.

Sam was confused as he watched the demons simply stare each other down; he didn't really get what was happening before it was too late.

Ruby cocked her head to the side, Dean smirked in response and then in a flash, she was on Dean, her tongue in his mouth and hands in his hair.

Sam backed away quickly, mouth open in both confusion and disgust. Dean slammed Ruby into the brick wall as he continued to make out with her. Her hands went to his butt and Sam turned and ran, almost running into the pop machine that was near the wall.

He glanced down at the key, feeling grateful that he had been the one who had grabbed it. There was no way that he would have been walking over to the two demons and asked Dean to please give him the key.

Sam walked quickly, eyes darting at every door he passed until he finally came across room 15. He unlocked the door quickly; hoping that Ruby's room wasn't located next to theirs. He really didn't want to hear his brother go at it with her.

The next morning Sam woke up to see Dean asleep on his bed, spread out on his stomach and lightly snoring.

Sam chuckled and left a note stating that he left to get some breakfast because he knew Dean would freak out if he woke to find Sam gone. When he returned, Dean opened sleepy black eyes and Sam smirked.

"Have fun last night?" he asked.

Dean let out a long, loud yawn. "Oh yeah rough demon sex is always fun. It also doesn't hurt that Ruby really knows what she's doing..."

Sam held his hands over his ears. "Gross! Enough Dean!"

Dean shrugged as he climbed out of bed. "You asked and you get an answer."

Rolling his eyes, Sam tossed his brother a sausage biscuit which he immediately ripped open.

There was a knock on the door and Sam immediately pulled out his gun. Dean froze and stared at the door, food spilling out of his mouth.

"Relax, I know you two have your weapons out. Now put them down and let me in."

Sam placed his gun on the table and opened the door to let Ruby in. He broke the salt line that wasn't there when he went to sleep. He had left the door unsalted so Dean could get in the room last night. His brother must have salted it himself before he went to sleep. Sam was glad that Dean's adventures with Ruby didn't cause his mind to go foggy and forget.

Ruby stepped into the room and smirked at Dean. "Hey lover boy."

Dean was in mid-chew, so he simply gave Ruby the middle finger.

"You should feel lucky. You know, if you weren't still in that pretty body of yours, I would probably not be banging you, no matter how good you are."

Dean swallowed loudly. "I wasn't so pretty down in the pit and you didn't seem to have a problem."

Ruby narrowed her eyes. "No one is pretty in hell Dean." The atmosphere in the room completely changed. "Besides, you looked better than me."

Sam knew what Dean's soul looked like, Ruby's was probably worse. Even though Sam figured most demons wouldn't care, it seemed that both Dean and Ruby had a hard time with their actual appearances. He actually felt kind of bad for Ruby.

Dean on the other hand, just smirked. "Damn straight I did. I'm the most human looking thing down there." Then as an afterthought he added, "But you didn't look nearly as bad as all those other bitches down there."

Ruby sighed. "I don't know which version of you I hate more. The human one or the demon one."

"They're both pretty obnoxious actually," Sam added in, causing Ruby to burst out laughing and Dean to scowl.

"Don't you dare take her side!" he growled.

"I'm just stating the truth Dean," Sam smiled.

Ruby suddenly walked over to the table and peered into the bag of food Sam had bought. Geeze, these demons with their damn food.

"The bagel's mine, yours is the other sausage biscuit."

Ruby took the food but eyed Sam warily. "You bought me food?"

"Yeah, consider it a thank you for helping us before."

"Well, then… next time you better remember to get me fries. I love those things like that freak over there loves pie." She pointed her thumb over her shoulder to Dean, who was already finished eating.

"Stop trying to rile me up." Dean walked over to sit across from Sam at the small table. "Let's take a look at what's going on in this town and try to figure out where this Samhain is hiding out at. I love how Crowley gave us no information."

"Oh yeah, that's right, I almost forgot," Ruby said, picking at her breakfast sandwich. "He told me Samhain would be hiding out in a church probably, he's going to be reciting some ritual to destroy everyone in the town or something."

"Thanks for withholding that important information." Dean rolled his eyes. "Then me and Sammy are going out to try and locate him. You go back in your room."

"What? Why can't I come too?"

"Because he can sense you, darling," Dean said in a sickly-sweet fake tone that caused Ruby to growl. "Later on tonight, he'll be with a bunch of demons like Crowley said, so it's not like he'll notice the addition of an extra demon around. But right now, he could be alone and I'm not taking a risk of him sensing you and having him kill us."

Dean then walked into the bathroom to get ready, effectively ending the conversation.

After the brothers finally convinced Ruby to go back in her room and salted her in there – which wasn't easy- they got into the Impala and Sam pulled out the list of church addresses he had looked up and wrote down. He pulled out the GPS and typed the addresses in.

"There's one four blocks from here actually…let's check out that one first." He clicked on navigate and the GPS told Dean to go right.

"Man, it's nice to get some peace and quiet." Dean pulled the Impala out of the parking lot. "She was driving me nuts."

Sam didn't argue with that. "You think we can trust her?"

"We kind of have to," Dean admitted. "Anyway, she hasn't really shown any indication of lying to us, Lilith hates her guts too, and we're fighting for the same thing. Trust me; I wouldn't be sleeping around with her if I thought she was a back-stabbing bitch."

Sam smirked at that. "I know you wouldn't. Anyway, if she wanted one of us dead, she could have done so already."

Dean hummed his agreement. "I don't think I have to ask this anymore, but you did take the blood kool-aid this morning right?"

"Yep, had it before breakfast."

"Good." Dean pulled the car to the side of the road. Sam saw that there was a small church across the street. "I'm not sensing a damn thing, you?"

Sam focused in on his powers and sensed nothing other than Dean. "Nope, we've got three more. Next one is about a five minute drive."

Dean followed the GPS's instructions to make a U-turn. "Hopefully Ruby will agree to help us with Lilith. We'll need a bunch of fucking back-up. Bobby's probably gonna be in, Crowley won't come within a thousand miles of the place, and who knows where the angel is."

"He said he was trying to distract the angels so they go after him and not us."

"Yeah, well I have a feeling that's not gonna last for long, I think we'll probably have a run in with those feathered asses sooner or later, it's been too quiet."

Sam didn't want to think about the possibility of the angels coming for them so he decided to change the subject. "So, what did Ruby really look like? You know, in Hell?"

Dean cocked an eyebrow at Sam. "Random. Uh, well…you couldn't really make out what she used to look like under all the scars and injuries. I mean, you kind of could, it was easier to make out what she looked like rather than the other demons. She probably used to be hot. Whatever hair wasn't burned off her head was blonde, I think she chose a similar looking girl to possess, although she looked shorter and had a thinner face than the vessel. A lot of demons do try and pick a vessel that looks like them, that is, if they can remember what they looked like."

"What do you think made her remember what it's like to be human? I mean, she didn't sell her soul for someone. She sold it to become a witch."

Dean shrugged. "I don't know. Maybe she was a really good person and it was tough to really break her. Or maybe she was just really stubborn. Maybe there's more that she remembers that she's not letting on…hey, this is it."

Sam immediately shook his head. "I don't sense anything." He saw Dean motion his agreement. "What if he skipped town?"

"Well, that might be good because he wouldn't kill any of these people, but bad because then we lost him and he'd just kill another town. But we still got two more, put in that next address."

Sam did as he was told and they drove off again. He couldn't keep his mind from wandering. "Dean?"

"What?"

"Do you ever…dream about Hell?"

Dean's grip tightened on the steering wheel. "What the hell is up with these random questions, Sammy?"

"I'm just thinking. And I wanted to ask you for a while, but was scared you'd scream at me."

The look Dean gave Sam looked a little sad. "I would never scream at you for asking me a question, you idiot."

"I know that now. I thought of the question back when we first got reunited and I was still getting used to you being a demon and crap."

Dean nodded and was silent for a moment. Sam almost thought Dean either forgot the question or wasn't going to answer.

"I don't dream, Sammy."

This shocked Sam. "You don't dream…what about Hell, or at all?"

"I don't dream at all…ever."

"Well…" Sam was at loss of what to say. "I mean, that's good that you can't dream of Hell. But…it sucks that you can't dream of anything good either."

Dean shrugged one shoulder. "I don't mind it. It makes it seem like I don't get enough sleep though, that's what I hate. Even though I don't really need sleep like you do…"

Dean trailed off and Sam figured that was the end of that conversation. That was, until his brother surprised him once again.

"I do think about it though. When I'm not keeping busy. The things that happened to me, the things I did. That's why I'm always being an annoying ass and I don't shut up or I mess with you, the more I keep busy, the less I think about it. Keeps me sane and focused."

Sam swallowed, not trusting his voice to not crack. "You don't ever have to shut up if you don't want to. Play as many pranks on me and aggravate me as much as you want. I won't ever complain again."

Dean rolled his black eyes. "Nah, that would really get on your nerves and you might actually use your powers on me and send me back to Hell to have some peace and quiet." At Sam's glare Dean chuckled. "I'm kidding Sam. But that's why I go out to bars and sleep around with women and irritate waiters and bang Ruby. I keep occupied without having to constantly get on your nerves."

"I get it, I do," Sam told his brother. "And I know I said this before, but I'm saying it again. If you ever want to talk about what happened down there, or just about anything…I'm here for you Dean. I'm always willing to listen."

Dean huffed. "I know that, no need to keep repeating yourself."

Sam huffed right back in response.

"And thanks," Dean added suddenly and quickly. Before Sam could respond he felt something…a demon…and a strong one at that. He looked in the distance and saw the big church they were approaching.

Dean locked eyes with Sam. "I think we've found our demon, Sammy."