A/N:

First try at a five things piece. I have no idea when it supposedly takes place, soooo. I hope that it's okay! (Also, I would totally love a beta reader!)

Disclaimer—

I don't own any of the characters. If I did, Sam and Dean would stop fighting and love each other and Destiel would be cannon.

The Five Times Cas Experienced Love, and the One Time He Realized It

Cas had a problem that he had no idea how to deal with. He had feelings. Or more accurately, he had begun to notice he had feelings. It was very unsettling. (The fact that he could feel that was even more unsettling) His recent involvement with humans had forced him to notice the signs of having emotions. It made him realize that when his chest hurt, it wasn't just his vessel becoming sick. Or when his body felt lighter, it wasn't just his mind playing tricks on him. Those little things he had brushed aside for thousands of years suddenly had meaning.

To be honest, he didn't really mind having feelings. It made his life much more exciting, and he enjoyed guessing at what human emotion he had experienced. Happiness, sadness, fear. Confusion, anger, joy. He enjoyed feeling all of them. It was all new to him, and it was exhilarating.

His problem though was that there was one emotion that he didn't understand, that always left him feeling extremely confused. One he only seemed to feel at the strangest of times.

(1)

The first time he felt it was late one night, after spending a few months in heaven. Everything was falling apart, and it broke his heart. His brothers had realized God was gone for good. It was a fight to see who would take over. They were creatures of habit, the angels. And they couldn't seem to learn that they could function without one leader. That they could co-exist peacefully.

It hurt that they would resort to violence so quickly. Cas hated the killing, and was absolutely sick at the thought of slaughtering even more of his brothers, even if it was self-defense.

He knew that he shouldn't leave in a time of such turmoil, even for a few moments. He should've been up in heaven, working to diffuse the tension. It was his duty as an angel to serve heaven after all.

But he couldn't resist.

While it had only been a few months on Earth, it had been many months in heaven time. Months filled with blood and heartbreak. He hadn't seen a friendly face in nearly a year. So he decided the only true friends he had.

As he thought about it, he was quite annoyed with himself for losing the cell phone Dean had gotten him. It definitely would've saved him some trouble. After spending an hour searching half of the most seedy motels in America, he decided to check one the few places the Winchester boys were comfortable. Sioux Falls.

So he flew as fast as he could, hoping that they weren't in one of the few motels he hadn't searched. He had no more time to waste looking around and this would have to be his last stop.

A few seconds later, he was standing, invisible, outside Bobby Singer's house.

He glanced around, into the darkness. He had failed to notice that it had gotten so late when he was trying to think of where to find his friends. At this time of the night, even they were most likely asleep. Should he go in and risk taking away the only few hours of sleep that they ever got?

It would be cruel to bother them with something as silly as wanting to say hello. They had dealt with the Apocalypse, and still come out on top. He knew that his tiredness was nothing compared to how two humans must feel. Maybe he could just…look at them. He would technically still be seeing friendly faces, they just wouldn't know it. That was okay.

He closed his eyes and appeared in Bobby's guest room.

And he sighed.

His heart sank as he stared the untouched bed in front of him. He had been positive that this was where they were staying. He was sure he had felt their souls' presence.

He was quite upset. The whole trip had been for nothing. He would go back and deal with a full scale Civil War, with no one knowing if he was alive or dead. He wouldn't get the comfort of having a friend. He shut his eyes. Having emotions could be painful.

Just as he was about to fly away, the door creaked behind him. His eyes shot open. He turned immediately pulling his angel blade out of his sleeve.

His eyes widened.

Dean was standing in the doorway with his double barreled shot gun aimed straight at Cas' heart. He stared for a moment taking in the scene before him. Shock washed over his body, stiffening his limbs even further.

Slowly, Cas put his weapon back into his coat. He felt relief flood through him. His heart lifted and suddenly he felt like there were a thousand tiny wings flitting around inside him. He was so happy to see him—he could hug him for hours on end. It if it weren't for this feeling. It was… weird.

"Cas?" He asked. There was something strange about him that Cas couldn't put his finger on.

"Yes, Dean." He replied, confused by the question. Who else would he be?

Quickly, shock and confusion morphed into anger. "Where the hell have you been? We haven't seen you in nearly a month! You've ignored our calls…Cas, we thought you were dead!" Dean shouts, some of his words slurring together.

Cas understands now what's off about Dean, and he's honestly surprised he didn't smell it the moment the door opened. Dean reeks of alcohol.

He stands still for a moment, trying to think of what to say next. He hadn't thought that Dean may have been worried about him. It had never even occurred to him. He had just assumed that Dean would have known that he had to return to Heaven to sort things out. As for the calls, he had lost that phone he had gotten him.

He scrunched his eyebrows together. The feeling in his stomach had not yet gone away, and he noticed that his heart was beating much faster than usual. What was wrong with him?

opened his mouth to respond, "I'm… sorry if my absence has caused you and Sam any fear. I've been in Heaven. Things haven't been going well ever since the Apocalypse." He pauses to look into Dean's eyes, "I'm sorry."

Dean stares at him for a moment and closes his eyes. He shakes his head, as though trying to get rid of a nasty thought. He closes the distance between them and pulls him to a rough hug. "I've missed you, man."

And the feeling is back, though now it's stronger than ever. His heart is beating a mile a minute and he has no idea why. So, he brushes it away and says, "I've missed you as well." He stops, but then realizes he should also add, "And Sam too, of course."

Dean stares at him for a moment sadly, and gives him one last squeeze and says, "Yeah, of course." Cas notes that he sounds slightly disappointed. "So I guess you have a lot to tell me then."

Cas pauses, because usually Dean doesn't want to talk very much. He figures that it must be the liquor, and he's grateful for it. He desperately needed someone to confide in.

They talked for the rest of the night, and Cas never had a single impulse to ask where Sam was.

(2)

The next time the feeling came back, it was brief.

He was at a bar with the Winchesters after helping them with a case involving a real trickster, barnyard animals, and many traumatized teenage boys. He supposed that it could found be amusing, because Sam and Dean made quite a few jokes about the situation. Maybe at some other time he would've enjoyed their banter, but currently he was feeling an unshakeable sadness and he was quite confused about why. He was with his friends after a successful hunt. Why would he feel like he had been punched in the stomach?

He glanced up at the bar at the two blonde girls staring straight at Dean and giggling. They were attractive he supposed, and they were identical, for the most part. He knew how human men (and some women) felt about twins, but he couldn't see why. What was so extraordinary about two people having similar physical features? All that truly mattered were souls, and theirs were quite dull. They didn't have any hopes or dreams that didn't involve removing their clothing, or filming strange explicit things.

As he watched them watching Dean, he felt his heart ache even more.

Minutes later, Sam voiced his thoughts. "Dean, those girls are totally into you. Normally you would have been over there five minutes ago." Questioningly, he raised his eyebrows.

He looked over to the bar with a quick grin and a wink. Before answering, he picked up his beer and took a deep swallow. "Not every night is about sex, Sammy. Why can't I just spend time with people I actually care about?" His eyes darted over to Cas at this point.

He moved his gaze up from Cas' lips and up to his eyes. "Plus, Cas is here and that doesn't happen as much lately. They can find some other guy to screw." Castiel's hear sank when he thought of how little time he had spent with his friends, but quickly lifted when he realized how much Dean cared about him.

He quickly changed the subject to avoid talking any more about his feelings. "So, that kid was pretty into that cow before the trick wore off. Anyone else find kinda creepy how easy it was for that nut job to get him to think it was a chick?"

Cas looked down at his burger and smiled. His stomach was light, and he felt like he was flying. His heart pumped quickly. The feeling was back, but he was too happy to care.

(3)

The next time Cas felt the feeling, it was most definitely a peculiar situation. Dean was sleeping on the ground by his feet at the time.

Sleeping being a loose term. (Dean would later be quite angry about how this came to be)

Dean had been separated from Sam during their raid of a vampire's nest. He had single-handedly killed five or so, but not without injury. He was a mess. So, he shut his eyes and prayed that Cas would come. He knew he wouldn't have long without help.

Cas appeared seconds later, hoping he wasn't too late. By the time he reached Dean, he had fallen to his knees. He was cut all the way from his waist to his neck, and the cut was very deep. Blood seeped out of it, soaking his shirt. His nose also appeared to be broken. Cas hadn't ever really experienced pain like humans, but he could tell that injury was causing a lot of it. So, he moved his slightly trembling fingers and pressed them to Dean's forehead.

As the wounds gradually faded away, Cas grew dizzy from the loss of power. He had been weakened already from a fight with what humans might call 'communist' angels, who wanted all angels to leave Earth forever. With the way he was feeling now, he knew wouldn't be flying anywhere for a while.

Dean groaned and began to try to stand up. He must've been exhausted, Cas thought. Even though his wounds had sealed, he had just fought his way through half a nest of vampires.

So, Cas decided to help him. (or so he thought) He reached down to a protesting Dean and touched his forehead again, although for a different purpose.

Dean collapsed to the ground, out cold.

Cas looked him over. He was covered in blood, some of it his own, some of it the vampires'. His nose had healed and was once again set properly. However, he looked different, Cas noted. His face was much more relaxed, and he had the child-like innocence that humans got when their guards where let down. Quite simply, he was adorable.

Cas smiled lightly at the thought of what Dean might say about him calling him adorable.

For a long stretch of time, he stared. Every moment as he stared his heart beat faster and he felt an uncomfortable moisture on his hands. He shivered deeply. The pit of his stomach was filled with millions of tiny wings.

He sighed. At what point would he figure out what these things meant? Emotions were difficult for him, and he had no idea who to turn to. What if it wasn't a normal feeling for humans, and his vessel was falling apart? It had never happened to him before, so he couldn't rule it out as a possibility.

A few moments later, Cas began to hear shouting from far away. He realized that he hadn't considered the wounds Sam might've gotten, and he hoped desperately that he was okay.

"Dean?! Are you alright? Dean!" It was Sam. Cas exhaled a breath he hadn't known he was holding. If Sam was up and searching for Dean, then he was in good condition.

Cas appeared in front of him, "Dean is alright, Sam."

The feeling gradually faded away.

(4)

Dean was devouring his slice of cherry pie, until he realized that a certain angel wasn't doing the same. "Cas, you gotta try it. It's awesome."

They were trying to convince him of the joys of food. He stared uncomfortably at his plate. Eating human food had never been a pleasurable experience for angels. They put so many chemicals into everything, and Cas knew that if he took a bite he would be able to taste every single one.

"It's not bad, man." Sam said laughing at the angel's obvious discomfort.

"C'mon. If you hate it you can stop." Dean said imploringly. As if to prove that Cas would have to like it, he cut off a piece with his fork and lifted it into his mouth. He groaned, causing Sam's eyebrows to shoot up. "See? It's great."

The sound made the feeling in Cas' stomach explode, and he felt slightly dizzy. He could barely breathe. Suddenly, his clothing, mainly below the belt, felt too small.

Slowly Cas picked up his fork. He sawed it through the crumbly crust and the gooey cherry filling until he had one, teeny tiny piece. Dean nodded encouragingly.

He slid it into his mouth quickly as he could. It was disgusting. The taste of cherries soaked in sugar mixed with the acrid taste of chemicals and butter was something he never wanted to taste again. He knew though, that Dean was just trying to share something he loved with him, and for that he was grateful.

He forced something he hoped would resemble a smile, and swallowed thickly. "You were right. It was quite delicious."

"I thought you'd like it. Who doesn't like pie?" Dean said grinning. If he noticed anything strange about his friend's reaction, he said nothing.

"Yeah," Sam said looking at the angel strangely. His eyes darted between Cas and Dean.

However, Castiel didn't even notice Sam's curious glances. He was smiling back at Dean, and trying to remember how to breathe. He felt like he was floating on air.

(5)

The next time, his friends didn't even know he was there.

He had come intending on visiting them, but they were deep in conversation about a case. He decided to wait, invisible, and let them finish.

Sam…looked upset. Not angry-upset, but cracking-under-the-pressure-upset. They had lost a fellow hunter, an old friend, that weekend.

"Sammy, obviously you're a little screwed up right now. So how about you just chill around town tomorrow?" He paused at Sam's conflicted look.

"Dean, I'm fine, I can help."

"Just…take a day off. God knows you could use it. I can handle the case, it's pretty amateur." Dean lied. From what Cas had heard, this case was most certainly not 'amateur'.

Sam hesitated before sighing. "I want to help…But I think you're probably right. I could use a some extra sleep…But—"

"Sammy."

Sam stared into his eyes like he was searching for some sign of a trick. Castiel could tell that he didn't understand why Dean was trying to help him, especially after all he had done to him.

"Sam, if you don't stay, I'll make you stay."

Sam ran his hand through his hair, and after a moment, said, "Fine. But this won't happen again. I need to hunt."

As he watched Dean continued trying to shield Sam from getting hurt more even after everything they had been through, his heart swelled. What he felt ran deep through him, down into his non-existent soul. It reached through every part of him, and his heart pounded in his chest.

He realized that the feeling he had been struggling with for so long may not be a bad one like he had thought. For the first time, he strangely enjoyed it.

After Sam had left, Cas appeared to Dean. He told him that he would gladly help him on the case.

(realization)

Castiel knew that he wouldn't be able to figure this out on his own. He had never had to worry about feelings until recently, and he was out of his league. So, he called Dean (with his new phone) and asked where they currently were staying.

"Avondale, at the Motel Six. Room 5."

Half a second later he was there.

Apparently, he had not measured the distance correctly because he had shown up very close to Dean. Inches, actually. He remembered the times that he had done this in the past. It had been awhile. Dean's eyes were even more beautiful up close.

"Hello, Dean." He stated somberly, loving the way the light in the room made his green eyes luminous.

He cleared his throat. "Cas."

"I…need help." He said sheepishly.

Dean looked at him with those bright green eyes and the feeling hit him harder than ever before. His knees were weak, his heart pounded, and the butterflies in his stomach had comeback with a fury.

"What's up?" Dean asked, sounding slightly…nervous? Dean moved slightly closer, causing Cas' breath to hitch. They were even closer in proximity, after all.

And suddenly Cas understood the feeling. Love. There was no other explantation. It was exactly how people described it; wonderful, and beautiful—but also very confusing. And sometimes painful. It was the most coveted human emotion, the one everyone wanted to feel. He totally got why.

He breathed out a tiny, "Oh."

"Cas?" Dean asked quietly. He had slid even closer, their faces a couple of inches apart at the most. He felt like his pants were going to burst. He desperately hoped Dean didn't notice.

He was so close. So close that Cas could kiss him, and for the first time in his life, he actually wanted that with someone—with Dean. He had never done it before though, and it was quite nerve racking. He knew that Dean most likely didn't reciprocate the feelings. He had been with many, many women, and had never shown in interest in men. Silently, he cursed himself for choosing a male vessel.

"Dean, I-" Cas noticed that he seemed even closer than before. His eyes flitted down to Dean's full lips. He could just lean forward a little bit…

"I've been having a strange feeling lately." Cas ground out, trying to focus.

Dean quirked his eyebrows, "Oh?"

"I don't know what to make of it and I—" Dean cut him off and smashed his lips into Castiel's and he swore he saw tiny stars burst behind his eyes. He began to move his mouth with fervor.

Dean pulled back looking surprised with himself. "I…uh…I've been having a ….strange feeling too."

He looked at Cas nervously. This was uncharted territory for him. He never felt anything so deep, and especially not with another dude. He knew that it was worth giving a it a shot, though, even if it was a strange new experience. He tried to steady his breathing. No dice. "I'm not really good at this emotional stuff, Cas. But we'll, uh, figure this out together. It…it could be good, you know?"

After a minute, Cas smiled when his brain finally processed what was happening. Dean wasn't repulsed at the idea of being with him—he wanted it too. He had never been more happy in his long, long life. It would be—

There was a loud crash and they both looked up. "Holy…shit." Sam whispered, looking shocked.