A Playful Pup's First Anal Vore - by Darkest Enigma

Not too long ago, in the Unova region, a certain Charmeleon named Charem traveled with his master, Guan, on a quest to beat the Unova Gyms and, eventually, the Elite Four. Sometimes, however, they become sidetracked because of a certain ‘meleon’s voracious appetite and the many ways he had to tame this great hunger of his. Not that anyone had complained about this too much, of course. A Pokémon has to eat, after all.
Sometime during this journey, perhaps around Lostlorn Forest, or maybe around Nimbasa City, a stray Houndour began to follow them, cautiously at first, then, warming up to them, came up to them and they quickly became friends. Sometimes, after a Gym battle, or when they were just staying in one place for a day or two, the dark Pokémon, who they came to know as Enigma, would mess around with Charem, from singeing the green grass and lazily watching it spiral upwards, to helping Charem catch his “food,” though he himself had yet to experience being the Char’s snack himself.
Eventually, Enigma became used to their regular habits and traveled with them happily. Though not officially a pet or Pokémon of Guan himself, the little Houndour might as well have been. He had even battled alongside them on occasion, and was still with them when they beat the Elite Four!
One day, a little bit Charem, Guan, and Enigma arrived at White Forest for the first time, they were messing around, chasing the Starly, when Charem’s stomach growled. Guan and Charem both smiled at the sound.
Guan, still grinning, said, “Why don’t you two go and find something to eat? I’m sure Charem would love to.”
“I definitely do!” said Charem, a hungry look appearing on his face.
“Ok!” said Enigma, who always enjoyed helping Charem find something to eat.
“Ok then,” said Guan, “Don’t get anything too big, Charem!”
Hearing the joking tone in his master’s voice, Charem replied, “Ok, Master Guan! I won’t!”
With that, the Houndour and the Charmeleon went deeper into the forest.
They went deeper and deeper into the forest, passing by all the Seedot and Whoopers, until, eventually they came across a rare and beautiful Ninetails. The two smaller Pokémon hid behind a large tree, Enigma understanding Charem wanted this one as his meal, got into a pouncing position, and, instead of pouncing, used Sand-Attack, a move that, however low leveled, helped him and Charem hunt.
The Ninetails, suddenly frightened and blinded, frantically tried to swipe the dirt from it’s eyes. That was when Enigma pounced on the bigger Pokémon, who, being caught off-balance, was knocked to the ground.
Quickly, Charem came out from behind the tree and bound it’s limbs with a vine he had found behind the tree. After that was done, the dust was wiped from the Ninetails’s eyes and, upon seeing the two smaller Pokémon, relaxed somewhat, safe in the knowledge that they weren’t predators that would hunt bigger Pokémon like it for food. Oh, how wrong it was.
After examining the Ninetails, Charem said to Enigma, “I feel like the back door today.”
Enigma nodded, knowing full well he wanted no help with this.
Charem turned around, facing the opposite direction of the Ninetails, pulled his cheeks apart, revealing the well-practiced pucker, and slowly sat on the hind legs of the Pokémon.
The Ninetails, unaware of these events, staring at the sky, suddenly became aware of a warmth slowly up it’s legs. It looked down, and it’s eyes widened at what it saw; It’s own hind legs being pulled into the chubby Charmeleon’s voracious rump. The Ninetails began to struggle, but this only succeeded in increasing the volume of the murring of the smaller Pokémon ,but still, the Ninetails wriggled and squirmed, only succeeding in sending himself deeper into the Charmeleon’s 
After a few minutes, the only thing left of the Ninetails out of Charem’s rump was the head of the uselessly struggling Fire-type was it’s head and that, too, was soon swallowed up.
Charem, bloated somewhat from the Ninetails, decided to rest in the sun filtering through the trees, his friend, Enigma, deciding to lie next to him, stared at the struggling gut, which slowly calmed as the Ninetails grew tired and fell asleep. Charem noticed this and, as the little Houndour’s stomach growled, as his own did earlier, the Charmeleon came up with an idea.
“Hey, Enigma?” Charem asked. “You wanna try something?”
“Sure, “ replied his friend, “What is it?”
“Oh, you’ll see,” said the mischievous Fire-type.
“Ok. What do I have to do?” asked the Houndour, thinking of all the things it could possibly be.
“First, sit like this,” Charem said, having him lean against a tree and exposing his pucker.
“Ok?” said Enigma, who was slightly uncomfortable in such an exposed condition, as he was not used to it, but was going with it, “What do I do now?”
“I’ll do the rest,” said Charem, lowering his head until it was near the Houndour’s sphincter, “You just relax.”
“Um, Charem? What are you doi-,” Enigma cut off as Charem pressed his snout into the Houndour’s rump, slowly but steadily, pushing at the Houndour’s back entrance until it opened up, the Charmeleon’s snout going deeper into the slightly wincing, slightly panting Houndour’s bowels. He didn’t stop there though! The eager ‘mealeon continued to push deeper into Enigma’s behind, until his head was completely inside the wincing, panting wolf Pokémon’s rear. 
Charem, having stopped for a moment, asked his friend, his voice slightly muffled by Enigma’s insides, “Like the feeling?”
The only answer he got in return was the low murring of a contented wolf.
Charem smiled at this and continued to push deeper, this time with Enigma pushing against him, moving Charem ever further into his depths.
Eventually, it got to the point where Charem couldn’t push himself anymore, as his legs had been crushed together by the Houndour’s tight pucker. This, however, wasn’t a problem, as that meant that all the Houndour had to do now was point his rump skyward and let gravity finish it for him, and that’s exactly what he did.
Having a little trouble, as Charem was a bit bigger than he was, and therefore, making it harder to move with the pleasantly squirming Char in his bowels, the infatuated Houndour tilted himself so that Charem’s legs were pointed skyward and simply waited for gravity to do it’s work.
As Charem became entirely encased in the little Houndour’s bowels, he squirmed a little to get comfortable, while simultaneously earning a small, pleasured growl from the exhausted Dark-type.
Charem laughed a little, as his eyes began to droop. “It’s been a long, but fun, day. Now it’s time for a nice long nap, don’t you think, En?”
Charem was answered by his companion’s soft snoring. The Charmeleon chuckled once more as he closed his eyes and soon fell asleep along with his friend.