Note: I do not own Supernatural of any of its characters.
Castiel frowned as he looked down at the other angels in his garrison. Today was the day that all of them had been waiting for since the time they were born. Today was the day that they finally learned how to fly! It was what every little angel dreamed of; learning to fly like their big brothers and sisters. Castiel had been no exception. One of his earliest memories was of being carried through the air in someone's arms. Sometimes, he could still feel the wind on his face and hear a voice (he could never remember whose) telling him that he would grow big and strong, just like his siblings. But the day had finally arrived. And Castiel was too scared to do what was necessary to learn this coveted skill.
He had been fine up until a few moments ago. He had completed all the tests that proved his wings had the strength necessary to hold up his little body. He had flexed his muscles to make sure nothing cramped up. And then it had come time for the final step. The angels were supposed to launch themselves off a cloud, flap their wings, and use the wind to direct where they flew. One by one, the angels in his garrison had done this. But when Castiel had approached the edge of the cloud, he had made the mistake of looking down first. It was so high up! The little angel could see the tips of the mountains, like spikes, on the Earth below, and the grass, not nearly soft enough to break an angel's fall. If Castiel succeeded in flying, the Earth wouldn't be a problem. But if he failed (which wasn't unheard of) it would mean at least an hour of unimaginable pain, while he waited for an older brother or sister to find and heal him. Of course, Anna should be there to catch him, but there were over fifty angels in the garrison. She couldn't possibly keep an eye on them all, and if she took her eyes off him for just a second…
So, here Castiel was. Standing on the edge of the cloud, watching his brothers and sisters play beneath him. He could see Uriel and Balthazaar playing tag. They hadn't noticed he was missing yet, so caught up were they in their joy. But they would soon. The trio never spent long outside each other's presences. How was Castiel supposed to explain to them that he was too scared to take the final leap?
There was a rustle of feathers behind him and Castiel winced, thinking it was one of the members of his garrison. Turning slowly, he tried to prepare an explanation of why he was still on the cloud. Then, he relaxed. It was the archangel Gabriel. While no less embarrassing to admit his fear to, archangels were usually too busy to play with. Chances were, the next time he saw Gabriel, Castiel would have already learned how to fly, making this moment just a memory.
"Hey, little guy." Gabriel greeted, beaming at Castiel with his ever present smile. "Whatcha doin?"
"Hi, Gabriel." Castiel forced what he hoped was a confident smile. "How're things higher up?"
The archangel avoided his eyes for a moment. "Oh, Mike and Luci are fighting. Again. So I decided to check up on my little sibs." Gabriel ruffled Castiel's hair. "So, whatcha doin? Why aren't you down there? Learning to fly?"
Castiel frowned and looked down in shame. "I…I…I'm too scared. It's so far down!"
"Well, yeah," Gabriel laughed, "That's why you flap your wings! So you don't fall."
"I know! But...I just…I…what if it doesn't work? What if I…what if I fall?" Castiel trailed off, expecting to be ridiculed for his lack of courage. Instead, a finger tilted his chin upward and Castiel found himself looking into gentle, golden eyes.
"Well, that's why you've got Anna looking out for you." Gabriel told him.
"I know, but what if she looks away and then I can't hold myself up and then I end up falling and then I get hurt and-"
"Whoa , there kiddo!" Gabriel held up a hand. "You worry, too much! Look, why don't you try it while I watch? That way, if you fall, I'll catch you?"
"Really?" Castiel's eyes widened with renewed hope.
"No." Gabriel rolled his eyes. "I just said that so I could make you feel bad."
Castiel bit his lip and looked down. "Oh. Of course-"
"I was being sarcastic!" Gabriel sighed, draping a wing over the little angel's shoulder. "Of course I'll look out for you! It's what big bros do! Now, you just go to the edge of the cloud, jump off, spread your wings, and flap."
"Thank you, Gabriel!" Castiel squealed and dashed to the edge of the cloud.
With an archangel helping him, he'd be flying in no time. Castiel cast a glance back at Gabriel who gave him a reassuring nod. Not needing any more encouragement, the little angel threw himself off the edge. The wind filled up his wings, holding him up. Laughing, Castiel flapped his wings and rose higher.
"There you go!" Gabriel cheered him on. "You're a-"
Castiel didn't get a chance to hear what Gabriel would have said. A powerful gust of wind blew the opposite direction from which the little angel was flying and knocked him back. His focus and balance disrupted, Castiel cried out as he hovered and then plummeted.
"Gabriel!" Castiel screamed. He could see the ground getting closer. It was still far off but-
"Gotcha!" Gabriel's voice said, as strong arms enveloped the little angel. Castiel gave a sob and buried his head into his older brother's chest. "Easy, little guy." The archangel soothed. "I've got you. Nothing bad can happen to you while I'm here."
"I-I fell!" Castiel cried.
"Yeah, but I caught you. Just like I said I would." Gabriel rubbed his brother's back. "And before that, you were doing pretty good."
"I-I was?" Castiel peered up at the archangel, blinking away his tears.
"Best first time flyer I've ever seen." Gabriel assured. "Look, why don't you try again?"
Castiel bit his lip and looked away. "I want to but…"
"You're scared." Gabriel finished. "I get it. It's okay."
"Thank you, big brother." Castiel rested his head again.
"But, you know, you need to try again sometime. Why don't we take a break and try later? There're these cool new things called fish I could show you."
The little angel hesitated. "Will you be there? If I fall?"
"Of course." The older angel laughed. "I'll always be here to catch you."