A/N: So this is my first fan fiction that I've ever uploaded, and I'm sorta nervous, so please, give me feedback about how I should update my writing style. Thank you!

Also, side note: You'll notice the names Adam and Mackenzie Winchester. Adam is in fact Adam Milligan and Mackenzie is an OC from my AU, which is where I pulled this little snippet from. They aren't really important to the story, but just know that that's who they are if you are confused.

Enjoy!

Hark! The Herald Angel Sings

It was the twenty-fourth day of December, Christmas Eve, as humans called it these days. Castiel, of course, knew that the day that they celebrated the birth of Christ was inaccurate. Jesus had actually been born sometime in the fall, August perhaps, on a warm evening, not in late December. But then again, the blue eyed angel thought as he stared out the frosty edged window of the Winchester Impala, humans in this day and age generally didn't get much right when it came to their creator and his workings.

Nevertheless, it was on the occasion of Christmas that Castiel had joined Dean, Sam, Adam, and Mackenzie in the black '67 Chevy automobile. They were driving through the Midwest of the United States, on their way to Bobby's house in Sioux Falls, South Dakota so they could "be merry and bright," as Dean had phrased it.

The thought of Dean speaking, his voice deep and melodic, yet gruffly full of affection for his family, caused the dark haired angel to cast his eyes over to the left, where the eldest of the Winchester hunters was expertly navigating his car over the icy road through the falling snow. Although it was late into the night, the dark haired man looked as awake and alert as ever, his bright green eyes attentive as watched the road. Castiel found himself studying his companion, admiring the curve of his jaw and cheek bones, and subtle stubble that lined his chin. His hair was as messy and disheveled as ever, but the angel found that endearing, rather than unattractive.

"You're staring at me," Dean said in a matter-of-fact tone.

Castiel felt his face go beet red. He was thankful that the three younger Winchesters in the backseat were all sleeping peacefully, snoring together in a soft harmony. Dean didn't sound upset that the angel had been looking at him, more slightly curious, and possibly even amused.

"You're an interesting person to look at, Dean," Castiel said quietly, partly because he didn't want to wake up the sleepers, and mostly because he didn't want Dean to hear how his voice shook every time he spoke to the hunter. There was a reason the Castiel only ever talked softly, or with little emotion. It was because he feared that if ever he were to do anything else, Dean would figure out how he truly felt about him.

Dean chuckled softly. "Thanks, Cas. You're not so bad to look at yourself."

Castiel felt his face once again feel heated as he blushed. How could Dean so easily slip into that flirtatious state of mind? He made it seem simple, effortless, but whenever Castiel tried to copy that sort of example, he always overthought it and ending up feeling awkward and foolish.

"Thanks," Cas said softly before slumping back awkwardly in his chair, feeling mildly dejected that he couldn't be so good at conveying his emotions through his verbal actions. Out of the corner of his vision, he watched as Dean's brow creased into a slight frown, obviously disappointed that Castiel hadn't responded back in the same flirtatious way. But quickly the expression was gone, as the hunter broke into a playful smirk and reached for the radio dials.

"I dunno how good the signal will be in the snow, but..." Dean muttered, fiddling around with the buttons and dials until he came to a Christmas station.

The song was just ending when the signal stopped being fuzzy. "-mas and a happy New Year!" Then the station went right onto the next song, which went something like this:

"Hark! The Herald angels sing

Glory to the newborn King!"

Castiel tipped his head in curiosity as he listened to the music. "How is that these singers knew about that happening?" he asked in confusion. "It is not possible that any of them could possibly have been alive at the time Christ was born."

Dean glanced over at him, clearly startled. "What the hell are you talking about, Cas?" The eldest hunter looked confused, as if he didn't have a clue in the world what the angel was talking about.

A frown graced Castiel's delicately dark eyebrows as he cast his clear blue gaze towards the hunter. "The song, of course. They're telling the story of all how all the angels chorused as one the night that the virgin Mary gave birth to the Son of God."

"Whoa, whoa, wait, you sing now?" Dean asked in surprise, momentarily taking his eyes off the road to glance at his angel friend.

Cas winced slightly, suddenly wishing he hadn't brought up that topic. That night hadn't been exactly a good one for him. "Not really," he shrugged nonchalantly, praying that Dean wouldn't press him for further details.

"So you were really there when Jesus was born. You sang to Jesus?" Dean asked incredulously, not noticing the tension in Cas, obvious in the stiffness of his shoulders and slight clenching of his jaw.

"Of course. All the angels were called to witness the incarnate of God being birthed," Castiel said in a clipped voice. However, Dean, as clueless as ever, was in too much excitement to notice that Cas was uncomfortable with the topic.

"Well, tell me about it!" the hunter urged.

Castiel sighed softly. "Really, Dean, I don't particularly have any desire to speak of that night. It not really a...good, memory for me." Cas found it hard to look at the hunter, as he sensed his heightened emotion of excitement drop to disappointment before morphing into...what was that? Sympathy? Compassion, perhaps? Maybe even a hint of regret?

"God, I'm sorry, Cas. I didn't mean to push you or anything," Dean said apologetically, his voice soft and caring. Taking one hand off the wheel, the young hunter reached over and rested his hand on Cas's leg, just above his knee. The touch of the human sent Castiel's nerves and senses into a frenzy of excitement, but it was dulled as he thought about that terrible night so many centuries ago.

"If you don't want to talk about it," Dean continued, "you don't have to."

Castiel slowly turned his gaze to the hunter, who was looking at him gently, all the while driving the Impala and not even swerving the car in the slightest. Cas knew instantly that his friend's words were sincere. The angel knew that the hunter cared about him, and would tell him anything that he asked, and after all the secrets he'd kept from the Winchesters over the years, he suddenly felt a strong sense of obligation to share his most embarrassing moment with Dean. Hell, God knows that Dean had done plenty of embarrassing things in front of him!

Taking a deep breath, and finding comfort in Dean's casual, yet intimate touch, Castiel began his story of the night that the herald angels sang.

"We, the angels, I mean, were all supposed to gather together in one heaven so that we could join our voices together to sing for the child. I was there promptly, of course, because punctuality is an important concept in heaven. I was much younger back then, mind you, still growing into my wings as you might say-"

"Wait," Dean couldn't stop himself from interrupting. "Are you saying that angels go through puberty?"

Castiel looked thoughtful for a few seconds before nodding. "Yes, I believe that's a good way to put it. We start out as small thought-forms, mere essences of our Father's mind. As He begins to think of us more, we eventually become more solid, more adult-like. We become soldiers for heaven. The time between the first time God thinks of us and the time that we become fully-um, developed-is actually much like the teenage years of a human.

"Anyways, when the kings were presenting the child with the three gifts-frankincense, myrrh, and gold-the angels joined in a chorus of Hallelujah, to praise the child. Then, each angel was to sing a blessing of their own to the child, meaning that we all had to sing...what do you humans call it? A solo? Yes, well every angel had to sing a solo. I was one of the last to sing, being the only halfway to soldierhood. I was not the youngest, but I was close to it.

"When it came to my turn to sing, I followed the example of my brothers and let my voice ring out loudly. And it was going well, until about halfway through my part, my voice cracked. And it was not just a small crack," said Cas with a sullen expression, "it was terrible and everyone heard it.

"Then the worst part was that the child started to cry." By this point Cas looked absolutely distraught, as if he were talking about a puppy that he'd had since before he could remember had gotten hit by and truck and killed. "I was so embarrassed that I did not even finish singing I just stopped. Luckily the next of my brothers in line quickly started to sing, but the baby didn't stop crying. Later my brothers tried to tell me that it was not my singing that caused Christ to weep, but I'm not stupid. And since then, I have never sang again."

(Switching to Dean's POV until the end)

Cas was quiet after his story and for a few moments, Dean didn't realize that he was finished talking. In total and complete honesty, if anyone else had told him that story, Dean would have busted out laughing. But this wasn't just anyone. This was Castiel, his friend, best friend, really, and Dean didn't find the story at all humorous, especially when he saw the look on the angel's face, the years of built of shame and embarrassment that were reflected in his eyes.

God, those eyes. Dean felt as though he stare into them forever and never, ever, get tired or bored with doing so. They were like crystalline pools full of barely suppressed sorrows and doubts, in himself and in others, but behind that was so much more. There was loyalty, and friendship, and perhaps even something more than that when the dark haired angel looked at Dean.

Dammit, Dean, cut it out, the hunter scolded himself mentally. Cas doesn't feel that way about you. Stop pretending and getting your hopes up. Besides, even if he did feel that way, it could never happen. Because everyone that you care about ends up dead or worse, so why even bother?

Pulling himself from his thoughts, Dean moved his hand from Cas's leg up to his shoulder, and gave it a reassuring squeeze. "Hey man, don't worry about. Voice cracking happens to everyone in puberty. I'm extremely guilty of it, in fact. And between you and me, Sam's voice still cracks sometimes." Dean smiled, trying to break through Cas's sullen expression.

It seemed to worked, at least a little. Well, he went from looking like he was about to cry from looking like he just dropped his ice cream cone on the ground, which Dean supposed was an improvement in a way. "And, Cas," Dean continued, "believe, it's probably not as bad as you think. It gets cold in the desert at night, maybe Jesus needed another blanket or something. I know that it wasn't your singing that caused him to cry. And even if it was, which it isn't, it's nothing compared to what would have happened if I had tried to sing to him. I probably would have made the poor kid want to crucify himself early."

Somewhere in the back of his brain, Dean knew it probably wasn't the best idea to joke around about Jesus, especially with an angel, but Cas did crack a small smile at his words. "I highly doubt that Dean. God would not have allowed that to happen, no matter how terribly people sang to him."

Dean couldn't tell if Cas was being serious or not, but he decided to play it and assume he was. "Ya, well, anyways. I don't think you should feel bad about it. It happened like 2000 years ago. Like a wise person once said, you gotta put you past behind you."

Cas was silent for a moment, looking insightful before he smiled. "You know, I don't think I do feel embarrassed about it anymore."

"I'm glad," Dean smiled, and he truly was. He was glad that he could help his friend get past a memory that had been haunting him for such a long time. Surprisingly enough, because Dean understood that Cas trusted him enough to tell him about his most embarrassing and deeply buried moment, then maybe Dean could trust his angel with some of Dean's own secrets. The thought made his grin grow brighter.

"Thank you, Dean. I appreciate that I could confide in you, without having to worry about you making me feel worse," Cas said quietly, before doing something that surprise both of them. The angel leaned over and wrapped his arm around Dean's shoulders and squeezed, giving his friend a one armed squeeze. Of course, the two had hugged before (in a very manly way, of course), but this was different. Cas didn't remove his arm after the hug, but left it casually laying half of Dean's shoulders and half on the back of the seat. Dean didn't make any move to push him away. Instead he just smiled softly, and thought to himself, God. I'm in love with an angel. What are the odds?

He glanced over at Cas, who had returned to staring out the frosted window pane of the Impala. A small, knowing smile had graced the angel's lips, as if he was able to tell exactly what Dean was thinking. And he was happy about it.

Maybe I can make this work. Perhaps there is something worth trying for here... Dean though, a flame of hope igniting in his previously dim heart. And if there is, then I swear to God, I won't fail Cas like I've managed to fail everyone else. I'll do anything to keep him from the fate that everyone else I know has had, if it's the last thing I ever do.

The End.