Hey, Cheerilee, Cheerilee!

by JimmyHook19

Rating: teen
Tags: Random, Sex, Human, Cheerilee, My Little Pony: Friendship is Magic, Comedy
Length: 1056

Get your bottles ready...

After the pepper incident, Jimmy has mostly returned to normal. However, things are about to get crazy once again...

Published 2019-02-11 22:20:01 UTC
Last updated 2019-02-11 22:20:01 UTC

Classroom Antics

It was just another day on Roanoke Island. A typical, quiet day out of the ordinary. In the town square of the largest settlement on the island, the town of Manteo (or City, as Americans call a settlement that even only has two people living in it a city), two townsfolk were having a discussion.

“Well, Monday has rolled around again,” said the first one. “Hopefully it will be a lot quieter than last week.”

“Indeed,” said the other. “Last week was very fiery.” Only a week earlier, the town had hosted a contest as to who could eat the hottest peppers, culminating with a Cayenne. The winner, a Mr. Jimmy Hook, had then vanished off somewhere, and had then gone missing for a few days, before reappearing, exactly as normal, a few days later. This, in and out of itself, was not entirely surprising. Jimmy Hook was constantly appearing and disappearing, and those disappearances usually resulted in a pony appearing for a few days. However, reports of a white unicorn with a reddish-purple mane and tail had been dismissed as nonsense, especially considering the person who had reported the sighting had been drunk at the time. What had not been dismissed as nonsense was the week earlier, where Jimmy had been sighted changing into a character from the hit TV show My Little Pony: Friendship is Magic. It had made news bulletins, but Jimmy seemed totally unaware of this when he appeared a few days later, apparently no worse for wear.

“What do you think happened to that fellow?” the first asked, putting his hand to his chin. “That...James fellow!”

“Oh!” the second replied. “Jimmy Hook! I haven’t seen him all day.”

“Well,” the first finished, “it has been a week since we saw another pony wandering around the town, let us hope we can go two weeks.”

He had no idea how wrong he would be...

Jimmy sat in the living room of his home, looking through a photo album of his. It mostly consisted of pictures from his time at school, which consisted of memories both happy and not quite as happy. He sighed as he scanned over the images, a younger version of himself looking back from behind the protective wallets.

“What fun days those were,” he said. “I wonder what it’s like on the other side of things?”

By ‘the other side of things’, Jimmy meant what it was like for the teachers. He had a friend in the UK who had briefly worked in the profession, and had heard enough about British schoolchildren to want to avoid that avenue of employment altogether. Indeed, it had seemed rather unpleasant to him, based on what this fellow had said. He decided that enough was enough, and put the book down and flicked on the television.

What should happen next but an episode of My Little Pony came on, Hearts and Hooves Day if Jimmy recalled correctly.

“Hey!” he said. “This one has Cheerilee in it!”

Like many bronies, Jimmy adored Cheerilee, the friendly schoolteacher of Ponyville (even if her reputation had been soured somewhat by a certain fanfiction). Her episodes tended to be a real hoot, even if she was usually relegated to crowd shots. Not surprisingly, Cheerilee was in Jimmy’s list of favorite MLP characters, as was everyone else. Currently clocking more than 1,348 entries, it would take a very long time to read.

Suddenly, the screen flashed a deep purple, which caused Jimmy to cover his eyes. When the light had cleared, he saw that all was normal, and things were running as they had been earlier.

But things were not normal at all, as his entire body suddenly felt itchy. Checking himself over, he suddenly saw a coat of purple fur sprout from under his skin, causing him to look like a purple abominable snowman.

“What in the-?” he asked, as he suddenly became aware of his hair flopping downward into his eyes. It had changed to a two-tone pink shade, which also grew down the back of his neck, stopping at where his shoulders were. It was clear to him what was happening now.

“Am I Cheerilee now?” he asked, before stopping, as his voice had changed to be exactly identical to that of Cheerilee’s voice in the TV series.

And then, his feet shifted into hooves, followed by his legs getting larger. This tore his socks open, followed by his hips shifting which forced him down onto all fours. Jimmy could predict what was becoming next, as he suddenly became a she. Her hips then widened slightly, followed by her chest growing larger as it morphed into that of a pony, which tore her shirt to pieces. Her shoulders shifted and moved to form front legs, followed by the joints changing to make the legs bend backwards. This was followed by her fingers becoming stiff, then merging together to form a pair of hooves.

Her neck then began growing longer, looking like that of a pony, as her ears shrank into the side of his head, followed by a pair of pony ears growing out of the top of her skull. This caused her glasses to fall clean onto the floor and shatter, which would have happened even if they had stayed on her face as her mouth and nose merged together, then grew out of her face to form a muzzle. Her eyes also went from blue to a grayish harlequin.

Finally, a symbol of three smiling flowers appeared on her flanks, followed by a tail of the same color as the mane growing out of her back. Two...things appeared between her legs, and with that the transformation was complete.

Cheerilee looked around her in almost total bewilderment. “Where am I?” she asked in confusion. “This doesn’t look like my home!” She set off toward the door, and opened up the door in front of her, trotting out onto the smooth cobblestones that marked her path, past her garden which had caused so much consternation in the past, and off toward the Ponyville schoolhouse, where another day of teaching and fun awaited her.

Just she might need a stiff drink afterwards...

Author's Note

1 of Two Cheerilee stories this month. The 2nd one will be revealed next Monday :raritywink: