Dean felt his weightlessness the moment after he had shoulder-charged the werewolf off the cliff. The last thought that crossed his mind was, "Oh, hell, this is going to hurt." Moments later his breath was ripped from his lungs as he hit a rock and began a wild roll down the hill. He didn't have time to gather himself at the bottom, however, as the second he landed he felt a crushing blow right below his ribs and he was sent flying until he hit a tree.
"Ugh," he groaned, stumbling to his feet and bringing forth a silver dagger he had conjured on the run over to the Whomping Willow. He was bruised, bleeding, and out of breath. And he was so exhilarated. This, this sort of situation was what he was used to. The werewolf snarled at him, rising onto its hind legs and roaring at him. "Come on then, you great big son of a bitch!"
The werewolf swiped at him, its claws aiming for his neck, but Dean ducked the blow and rolled out of the way. Already growing angrier by the second as its prey continued to evade it, the werewolf raised its maw in a howl. It charged him, on all fours this time, and he tried to dive out of the way again. He thought he had managed it when he felt a clawed hand wrap around his ankle and drag him backwards. He turned onto his back and kicked out at the muzzle of the werewolf, missing, and being dragged under the beast. The werewolf snapped at him, its teeth closing just centimeters from his neck. Dean, instinctively, went to shove the blade of the silver knife upwards and into the werewolf's chest, but he stopped himself short. Transformed or not, this was still Remus! He couldn't kill one of his best friends, could he?
"Come on, Remus!" Dean shouted, holding the blade horizontal in the werewolf's mouth as he forced the beast back. He saw that the silver was burning it, but it wasn't enough for it to back off from its assault. "Don't make me do this, Remus!"
Annoyed at the burning piece of metal between its jaws, the werewolf bit down on the knife and, with a vicious shake of its head, ripped the blade from Dean's hand and sent it flying into the darkness. Dean watched his lifeline go with a sense of dread and desperation rising within him.
With the werewolf's jaws bearing down upon him, he did the only thing he could think to do: he punched the beast in the side of the head as hard as he could from his prone position. It wasn't a good punch, no power at all behind it, but it served to further infuriate him.
When it looked like the werewolf's jaws were about to close around his throat, Dean suddenly felt the beast's weight disappear from him along with a loud series of growls and grunts. He scrambled to his feet and, to his equal gratefulness and horror, saw three slightly larger than normal wolves facing the werewolf with their teeth bared. "What the hell are you three doing?" Dean demanded, drawing his wand from his pocket. "Morgan, get those two out of here!"
"No, Dean," Morgan said, his snarl somewhat distorting the words more than usual. "We are already… what we are. His bite will not affect us, but you could still be turned."
"That's my problem!" Dean insisted. "You three are still just kids, get the hell out of here and let me deal with this!"
"Make us!" Star snapped, Dak growling his agreement.
"Dean!" Sam's voice, wildly out of place in this current group of beings, came from behind him. A moment later and the younger Winchester had joined his elder brother and his wand was extended towards the werewolf that was Remus.
"Sam, what the hell man?" Dean demanded for the second time in just a few seconds. "You were supposed to look after the kids!"
"I am!" Sam promised.
Dean glanced back, horrified at the prospect that Sam had brought the kids with him to face down a werewolf of all things. "Where the hell are they?"
"Back on the hill, with me!" Sam said, momentarily forgetting that Dean was basically clueless about the wizarding world still. At least, insofar as Time-Turners were concerned.
"You aren't making any sense!" Dean cursed, "Did you get hit on the head or something?"
"Nevermind," Sam said, "I'll explain later. For now we need to deal with Remus and then get back to the Whomping Willow."
Whatever Dean was going to say in response was lost on them as the werewolf rushed at them, the appearance of a second prey animal proving too much for its instinct to resist. Dak growled and bit at the werewolf and was promptly sent flying much like Dean had been moments earlier. "Son of a bitch!" Dean said, his protective instincts rising up as he saw one of his unofficial students being hurt. He reached for his wand and found nothing.
"Werewolves have a natural immunity to magic," Sam reminded him, tossing Dean a large branch. "We've gotta do this old-fashioned. We don't need to kill him, just scare him off."
"Sounds good to me!" Dean said, charging forward with the branch. The werewolf, momentarily distracted by Star as she bit at his leg, looked up a second too late as Dean brought the branch cracking across its skull. A splinter of what was, presumably, once a smaller branch caught on the wolf's skull and ripped at its ear. The werewolf howled in pain, the sound cut off when Sam's branch caught it on its throat. The sound of pain the beast made then was something of a kitten's cry. Morgan, Star, and now a recovered Dak, began to growl and snap at the beast's legs until, at last, it turned tail and disappeared into the forest with a piteous whine escaping it.
The forest was eerily still for a moment, all of those present straining their ears to listen for any signs of deceit from the creature. Only when Morgan visibly relaxed did Sam and Dean allow themselves to do the same. "I owe you guys," Dean said, sliding down against a tree and catching his breath. Now that the adrenaline was wearing off, he was uncomfortably aware of the pain coming from his ribs every time that he drew in a breath. "How did you know I was here?"
"Well, we heard a bunch of loud growls, the sound of someone falling down a cliff, and we thought 'Who else could it be?'" Star said, followed closely by their breathy laughter that was echoed by Dak and Morgan.
"We saw you leave the castle in a rush, so we thought that we should keep an eye on you," Morgan said honestly. "We saw you fall off the cliff and made our way here as quickly as we could."
"Well, you guys saved my ass," Dean said, extending a hand to Sam and using him to get back to a standing position. "Now, if you excuse me, I have some more kids to save."
"You may want to hurry," Dak said, cocking one ear to the sky and whining. "I smell something… something… cold."
Dean looked to Sam who nodded. "The dementors are coming for Sirius."
"Sirius Black?" Star asked, horrified. "No! We have to do something."
"Star, we can't do anything to them," Morgan told her. He turned his focus to Sam and Dean. "But you can. Sirius Black was a friend to us whilst he hid in the forest, I would ask that you two save him."
"We're on it," Sam promised, putting Dean's arm over his shoulder. "What's the fastest way to get back up to the Willow?"
"Well, that depends," Dak said, "Do you think Dean can ride?"
"Ride what?" Sam asked.
A few seconds later the sound of large wings came from above them and Buckbeak landed in the clearing before them. He cawed softly and, in a spectacular show of balance, Sam and Dean bowed to him unison. Buckbeak returned the bow almost at once and allowed them to approach. "Talk about good timing," Dean said, using Sam's cupped hands as a boost to throw his leg over the Hippogriff.
"No, I doubt that," Morgan disagreed. "Hippogriff's have a wonderful sense of smell and they are fiercely loyal as well as proud. He probably smelled you and wanted to come help you."
"I thought he was chained up waiting for the executioner?" Dean asked, glancing to Sam.
"No idea," Sam said, slapping Buckbeak's flank and sending the hippogriff flying to the air.
"Wait, Sam!" Dean shouted, looking back to see standing there watching him fly away. Morgan, Dak, and Star watched him go as well.
Unable to keep his balance while still looking back, he turned and wrapped his arms around Buckbeak's neck. The beast seemed to have some idea of where he was going and made a beeline for the Whomping Willow, making the journey in no time at all. However, now that Dean was in the air, he now saw that Dak had been right. The air grew unbearably cold seemingly all at once. Whether that was the reason that Buckbeak chose to land beside the Whomping Willow or that he recognized Harry was anyone's guess. Sam, the one who had been with the kids, breathed a heavy sigh of relief when he saw Dean slip off of Buckbeak's back and fall onto the ground. He helped his brother up, his wand extended at the rapidly approaching dementors.
"Hey hey hey! Dean! You still with me!?"
"Sam?" Dean asked, the pain from his ribs now pulsing throughout his body and clouding his thoughts. "How the hell are you here?"
"What?" He asked, confused. He dismissed his brother's sentence and dragged him over to where the students cowered. The first line of dementors were now less than fifty feet away, their initial hesitation gone and they approached eagerly. Only Sam's serpent kept them at bay and even that was beginning to fade. There were simply too many for one Patronus to handle. "Dean, I know you are hurting right now but I need you to cast a Patronus charm!"
"I don't have my wand!" Dean said, reaching for his pocket. He frowned when he felt the familiar smooth wood right where it hadn't been only ten minutes before. "Uh, never mind I guess."
"Professor!" Hermione screamed, covering his face when a dementor swooped in, presumably to administer the Kiss to what it saw as criminals. Sam directed his serpent back and the Patronus coiled and struck out at the eerie prison guard in an instant. The dementor screeched and flew several dozen feet into the air to escape.
"Happy memory… happy memory…" Dean muttered to himself. A moment later his impala bloomed from the tip of his wand and loped out to join Sam's serpent. The two Patronus formed a wall against the dementors, successfully keeping them at bay, but not causing them to retreat. "We've gotta do something."
"Potter, you have been practicing the Patronus with Lupin, right?" Sam asked, not taking his eyes off of the hooded figures. Several dementors, particularly daring ones, tried to move past the Patronus and were abruptly sent scurrying away. "If you want Sirius Black to stay alive and not Kissed, you are going to need to help us here!"
"W-what?" Harry asked, confusion written all over his face. Hermione grabbed him by the front of his robes and, in a voice too low for either Winchester to hear, gave him what they assumed was some words of encouragement. With his stance full of confidence, Harry got to his feet and drew his wand. He pointed it at the horde of dementors and shouted, "Expecto Patronum!"
A silvery mist blossomed from the tip at first, but the mist seemed to take form and solidify until a silver stag bounded forward and led the charge against the dementors. The guards of Azkaban scattered in terror now, the temperature quickly returning to normal levels.
"Potter, is Black conscious?" Sam asked quickly, striding forward.
"You aren't taking him!" Hermione, Ron, and Harry said as one, moving to guard Black with their bodies.
"He isn't a murderer!" Ron said, though his face was pale from the pain of his leg.
"I assumed as much when I saw Peter Pettigrew was alive and referred to Voldemort as the Dark Lord," Sam said coolly, stowing his wand in his robes. "However, until we get this sorted out, Black shouldn't be anywhere where he could be taken prisoner. You just saw what the dementors were like when they saw him, and I can't protect him once your Ministry gets ahold of him."
"So, what were you going to do?" Harry asked warily.
Sam explained his plan, which was pretty much the same as in the book minus a tower escape, and soon enough Sirius Black was astride Buckbeak flying into the rising sun. Sam made his way over to Wormtail's body and cast a Levitation spell on it, letting it bob before them as they made their way back to the castle. Ron, unfortunately, was left to be basically carried by Harry and Hermione as Dean was unable to lift him despite his best efforts. Soon enough they were all back in the Hospital Wing, a very unhappy Crowley attending to them.
"Truly, I ask you for one thing," he growled, checking Dean's bandages. "One simple thing. Don't make more work for me. Was that so hard? Apparently bloody well so!"
"Yeah, I love throwing myself off cliffs," Dean snapped. "First thing on the way down I think of is 'Wow, I can't wait to make more work for Crowley!'"
"Well maybe next time try falling head first, find out if you are a flying squirrel," Crowley said, pulling Dean's wrapping a bit harder than was absolutely necessary.
Outside of the Hospital Wing, Sam was speaking to Castiel in hushed tones. "And you are sure?" he asked the former angel.
"Very," Castiel nodded. "Time travel is a very precarious thing, the smallest change could have catastrophic consequences. Under no circumstances can you allow yourself to be seen by yourself."
Sam nodded and hurried off, following after Harry and Hermione.