• Published 15th Sep 2018
  • 692 Views, 21 Comments

High School Teaching Misadventures - Even Evil Has Standards



A history teacher slash soul can unwittingly takes a job at an all female high school.

  • ...
8
 21
 692

You're hired!

Louis Terwilliker shifted in the back seat of his car as his...servant was driving him to his new workplace. Perhaps "servant" doesn't do her justice, but "slave" and "henchwoman" are a little harsh...then again, she wouldn't object to either.

Emerald is a 20 year old dragon with dark green scales, sea green eyes, and G cup breasts. She was garbed in blue jeans and a crop top that was a regular shade of green. She was loyal to Louis and an avid, cocky fighter. More often than not, this was the reason she lost to him during their sparring, particularly their first fight when he rendered her and her sister half naked. But enough about her.

Louis was a 25 year old man with sandy yellow hair, dark blue eyes, one of which had miosis, or a shrunken pupil, and was wearing a black pinstripe suit. He alternated between twiddling his thumbs and breathing heavily, trying to calm himself down from stressing about his new teaching job.

"Master, we're here," said Emerald, but Louis didn't hear her for he had seen the campus; it was a fairly average looking building with the usual number of side entrances, a soccer field, a jogging trail, a statue out front, etc. Emerald reached into the console and pulled out a small, starry green Lego piece on a string. "Don't forget your good luck charm." But Louis didn't answer, so she opted to throw it at him instead. "Master!"

The piece bounced off his head and he jumped. "What?!" He looked around wildly before finding the piece in his lap and laughing sheepishly. "Sorry, I'm a little nervous." He picked it up and began tying the string around his neck. "I don't know if I'll get it or not."

"Just relax," crooned Emerald, "you'll do fine. You passed the exam with flying colors. They'd be crazy not to accept you." She leaned over and gave him a peck on the cheek. "Good luck."

"Thanks," said Louis. With that, he stumbled out of the car and gallavanted up the sidewalk. Somehow, the noise of Emerald driving away made him feel more nervous. As he walked up the sidewalk, he could hear a Gary Oldman esque voice:

"You know, it won't be so bad if the nurse is hot. Or maybe a librarian..."

"Shut up, Vortech."


To say that Louis was expecting the hallways to be loaded with ponies, griffonesses, dragoness, and other creatures would be true. But to say that he was expecting the hallways to be filled with females was another thing. Everywhere he looked, nothing but dames, ranging from A to G cup. It didn't help that the whispers were a little off putting.

"Oh look! A male!"

"What's a male doing here?"

"He looks cute!"

"I wonder if he's single."

"How do you suppose he is in the sack?"

Louis was starting to wonder if they had ever seen a guy before.

"Probably not, but we can fix that, can we not?"

"Will you please-?!"


Have you ever been looking so hard for something, only to realize that it was right in front of your nose? Well Louis went through just that; he was so desperate in trying to avoid any advances from the students and any potential migraines from that voice in his head, that he passed the door twice.

"I blame you for this, Vortech."

"Tsk tsk, now you know that talking to yourself is the first sign of madness."

"Touche," sighed Louis as he went pass the door. There was a desk with a name plate that read 'Raven Inkwell' right next to the doorway he came through with the way to the actual office still some feet away. Louis was briefly reminded of The Maltese Falcon.

Seated at the desk was appaerntly Raven herself, a middle-aged, light grey skinned mare with her dark brownish gray mane tied up in a bun, a tail that was the same color, glasses over her orange eyes, and wearing a white suite with a black pin of a pen in an inkwell, although her E cups were straining fit to burst, and black shorts that hugged her rear end. Louis cleared his throat. "Excuse me."

Raven looked up and her eyes widen as if the tenth wonder of the universe was right before her.
(Dumbo was the ninth; King Kong was the eighth.)
There before her stood a male, and he didn't look like any pony, hippogriff, changeling, dragon, griffon, or yak that she ever saw. He looked like a Minotaur except his face didn't look close to bovine, more simian. "May I help you?"

"Louis Terwilliger," said he, "I'm here for the job."

Raven looked at him as if he'd grown another head. "What?"

"The job," said Louis, his anxiety fading a little bit, "the job that was advertised in the paper," and to prove it, Louis reached into his pocket and pulled out a newspaper clipping he had Emerald's sister cut out. "'History teacher wanted, must have experience and license, come to Ponyville High.'"

Raven stared again, this time with uncertainty. "It doesn't say anything about it being female as one of the requirements?"

Louis studied the clipping again. "Nope."

"Hmmmm," Raven folded her arms, inadvertently bunching her fancy cans together. It didn't help that the shirt she was wearing was transparent, nor did Vortech.

"We can see that her bra is black and we like black bras, do we not?"

Louis pulled a face as he mentally yelled "SHUT UP!" Luckily, he was saved by another mare sticking her head out the door. She was a light fuchsia and grey alicorn, with a mane and tail that mixed the light shades of cerulean, turqoise, and cobalt blue with a pale shade of heliotrope, eyes that were a mixture of gray and magenta, purple shorts, and a goldenrod jacket shirt with a white undershirt that had a golden sun pin that showed off her G cup. "Is there something wrong, Raven?"

Raven started to say something, but Louis stepped forward. "Are you Celestia the principal?"

"I am." Louis showed her the clipping and she took it. After reading it, she looked at the man. "Would you step into my office, please?" He obliged, leaving the secretary very confused, and a little miffed.


Celestia showed him into her office where there were four desks: hers, the vice principal's, the dean's, and the assistant dean's. Right now, the latter desk of the former pair and the former desk of the latter pair were occupied.

(Make of that last sentence what you will)

The mare occupying the vice principal's desk was a dark blue alicorn smaller than Celestia with cyan eyes, a mane and tail that had a blue shade of sapphire contained by a grayish Persian blue outline, navy blue pants, and a light violet vest shirt over a white polo with a black patch of a circle with a crescent moon sewn on the collar that still showed her G cups.

The mare occupying the dean's desk was a light grey and cerise alicorn that was the smallest of the three with light purple eyes, a violet mane and tail with streaks of rose and pale gold, a blue miniskirt (emphasis on "mini"), a baby blue T-shirt over her F cups, and a dark blue blazer with a crystal heart pin.

Both of them stared at the human for awhile before the vice principal spoke, "Sister, why is there a male on the premises and in the building?" Celestia showed her the clipping. "Why doesn't it say anything about the feminine requirement?"

"Let me see that." Now it was the dean's turn to see it. "Well, it does say that the applicant must be experienced or have a license if first time experience so..."

"Uh, sit down please," said Celestia. Louis obliged by sitting in the chair in front of her desk. "Now you want to apply for the job, yes?"
"Yes."
"Any experience?"
"Nope."
"Well then," sneered the vice principal, "I guess you're at a dead end, yes?" Louis responded by pulling out a scroll and presented it to Celestia. She unrolled it, looked at it for a moment, then passed it to her sister who grumbled while passing to the dean.

"Seems legit," said the dean. "Are you sure you want to teach here?"

"Just one more thing," said Louis, "where are the guys and why is being female suppose to be a requirement?"

"Ah," said the dean, "that started out due to the male-female ratio, three females to one male. This building was originally a boarding house for ponies. Most ponies didn't have any homes, so they were allowed to stay. Over time, other species were invited, and it was decided that this place would be a home for every creature to live and learn, to coin a phrase."

"But," continued Celestia, "there was the little matter of the heat." (Louis winced at that one.) "This place isn't exactly what you called a safe house, but it does keep the students and faculty from sneaking out and coming on any stallion."

"Besides," finished the vice principal, a little smugly, "if you take the job, you'll have to put up with every single female in the vicinity, and some can be quite vociferous."

"Not quite, Luna," said Celestia, "some females can control themselves, like the chemistry teacher. But I digress, do you think you can handle it?"

Louis pondered this awhile, sat back and scratched his scalp, and said, "I live with two dragonesses, and I helped them with their heat hundreds of times, so it can't be that bad." But deep down he was nervous: tending to only two dragonesses in heat is very different from tending to God knows how many creatures that were not only dragonesses, but also ponies, griffonesses, changelings, and any other species he didn't know about.

"That also means may you have to live here for awhile. This place does have dorms so we can find a room in the teachers' dorm building." When Louis nodded, she said, "then it's settled. Cadance will show you around," she nodded to the dean, "then you can decide on the conditions of your classroom." Cadance got up from her desk and showed Louis out. Celestia turned to Luna. "Is the misandry really necessary?"

Luna snorted, "Well, he's asking for it. Walking around single file and stupid, making those cocky little hills, ganging up and walking our cakes off the picnic blanket."

Celestia gave her a look. "You're sure you are not thinking about ants?"

"Of course not! I just don't want him to hurt any of our students."

"Right. Still, you have to admit, he is easy on the eyes.

"Sister!"


Cadance showed Louis around the campus. There were classrooms for mathematics, home economics, culinary arts, chemistry, music, biology, geology, and carpentry...or wood shop. Then there was the auditorium for drama, the gymnasium for gymnastics (pfffft), and the cafeteria. Cadance saved the intended history classroom for last.

It wasn't that bad: desks in a row, white board, big desk for teacher, plaster ceiling, bookshelves, the works. Louis studied the board before turning to Cadance. "Do you think a SMART board would be acquirable?"

Cadance stroked her chin. "Maybe. They are expensive, so no promises. But I'll see what we can do. In the meantime, I'll show you where the nurses station is." But they didn't get far when they crossed paths with another female.

She was a black changeling (or very dark grey*), a dark cerulean mane and tail, harlequin eyes with dark greyish and black pupils (different shades), a sickly green miniskirt, and a cerulean button up polo that was open a bit at the top, showing her F cups for all the world to see. When she saw Louis, she licked her...lips in a sensual way. However, she gave Cadance a cold look after the dean coughed forcibly. "Cadance," she said in an oily voice...not unlike George Carlin's Diesel voice...in fact, it might as well be a genderbent version.

"Chrysalis," said Cadance in a tone that matched her look.

Chrysalis turned backed to Louis and her smirk returned. "And who is this handsome young man?"

Louis tugged at his collar and blushed. "I'm the history teacher.

"Ooh, and how did Tia come to hire such a strapping specimen?" Louis felt the heat rise to the point where he could only stutter. Luckily, Cadance came to his rescue.

"Well may you ask," growled Cadance. "The ad in the paper asked for one, although it just so happens that said ad lacked the part about the teacher being female. Do you know anything about that, Chrysalis?"

Chrysalis looked aghast and put a hand over her heart, bunching her melons together. "Why Cady, you're not accusing me of tampering with the paper just so we can get a male in here to sate our desires, are you?"

Cadance's stern look began to falter. "Uh..."
"Surely you don't believe that this place has only acquired such a stud because I supposedly messed with the paper?"
"Well-"
"And if me doing what you accuse is true, then it would be I who should give our dear history teacher the personal tour."

"Oh no you don't!" snapped Cadance, who for some reason drew an arm around Louis, "Principal Celestia asked ME too do it!"

"Oh please, Tia chooses you for everything. She might as well make you vice the principal and Lulu the dean."

"That's not true, and you know it," growled Cadance. While the two argued, Louis struck up a mental conversation with Vortech.

"Isn't it exciting to have two gorgeous creatons fighting for your affection?"

"They're not fighting for my affection, they're just arguing about who should lead me through the tour."

"Keep telling yourself that. Fret not however, for I have a way to dissolve this."

"It better not involve a duel where the loser is banished to Foundation Prime."

"One, I'm not strong enough to do that; two, you see that pile of cord over there?"

"Sure."

"Well, you try and break up the argument with a gesture that will land the piece you're wearing as a necklace on to that pile."

"Okay." Not sure what else to do, Louis unhooked the string from 'round his neck as quietly as he could, slid off the LEGO piece, and flicked it so that not only did it hit Cadance on the horn, but it also landed on the target that was the pile of chord. Out of the corner of his eye, he saw the cord began to twitch, but disregarded this as had both women's attention. "Now ladies, let's not split hairs over something that trivial. Since I'm the one that's being shown around, I'll decide who gets to lead me to the end of the tour. Now we're going to close our eyes, I'm going to move my hand back and forth until I reach the end of a poem. The one my finger is pointing to will be the winner. Alright, close your eyes." The 2 rivals glanced at each other then reluctantly obliged. Louis did the same then extended an index finger and moved his hand back and forth rapidly.

"Rrrrrrringspot! One-sa, two-sa, zig-zag-zav, poptie, gimmega, tin-lie, tav, harem, scarem, moychan, tarem, tare, tore, BUCK!"

Louis uncovered his eyes and saw that he was pointing to an empty space. "Huh," he said, "I guess you win by default Chrysalis."

The assistant dean cooed. "Well then, Buck, where were you two on the tour?"
"The nurse's office."
"Let's go then."


The tour to and from the nurse's office, while informative, was a bit harder for Louis take in. That was because Chrysalis spent most of it either making lewd comments, fondling herself, and pinching Louis in the behind. It got to the point where Redheart, the nurse on duty, actually fainted from the sight of Chrysalis dragging Louis into her chest rather than the fact that a guy was on campus. A red faced Louis was speed walking to the campus exit, when he heard Chrysalis say, "What's this?"

He turned to see her bending over to pick up his LEGO piece. "Don't!" he yelled, but he was too late. Chrysalis had picked up the piece and was engulfed in a bright light; when it cleared, Chrysalis was still standing in her school attire, but her arms were bound in rope long enough to mummify her crooked horn and to trap her in the underarm rope gag. Louis picked up the piece, reattached it to it's string and told her, "it's sensitive to being touched by anyone that isn't the owner. You should be considering yourself lucky that it didn't spark a more humiliation defense."

Chrysalis gave a muffled reply, but then they both heard another one, albeit less muffled. They turned to see Cadance, mummified from her hooves to her mouth in the cord Louis had been told about, with the plug having just been shaken off her horn. "What the hell happened?" asked Louis.

Cadance's horn lit up and encased the plug her magic and began unwrapping herself. As soon as she was ungagged, she said, "I had closed my eyes, I felt something wrap around my waist. I was able to uncover my eyes to see that it was the cord, but it gagged me before I could speak. The plug had rested on my horn and for some reason, every time I tried to move, I'd get a shock. I had no choice but to stay here." She had finished freeing herself from her cord bond/gag and stretched before continuing, "I have no idea why I was able to get free now." (Louis didn't know how to react to that one, but he could hear Vortech laughing.) Cadance finally saw the changeling and smirked. "You know, I think I like you better this way." Chrysalis snarled at her.

"What's with the beef between you too?" asked Louis.

Cadance's smirk faded a little. "She can shapeshift. That's all you need to know." She cleared her throat and her smile became sweeter. "Anyway, why don't you come over a few days before the start of semester? We'll get you settled in and you can be better prepared to meet your colleagues and students."

"Sure," said Louis, "but can you teleport me to the main entrance? I'd like to celebrate real soon."

"Wish granted," said Cadance, and with that, Louis found himself outside. "That was your plan? Tie up Cadance while the assistant dean and I had a little 'break' from the tour?"

"Oh, something like that. You know we like trussed up mares and the like."
"Oh puh-lease. Anyway I'm going to need you to start playing some music."

"Evard Grieg?"
"Yes, but wait until I finish a call." Louis pulled out a cellphone and dialed a number. At his home, Emerald answered her own.

Now I want you to visualize the phone conversations from the cartoons of the old days: one line down the middle of the screen, splitting it in half, with each side occupied by both callers. Something like that.

"Hello Master," crooned Emerald, "How'd the interview go?"

"I got the job!" shouted Louis excitedly. "I got the job!" He could hear Emerald squealing excitedly on the other end. "Now we can actually pay enough debts to be in the black again! I'll be heading there on foot so hold down the fort till I get there."

"Ok Master," responded Emerald. "I'm really glad you got the job. We'll celebrate," she said "celebrate" in a sensual tone, "tonight." With that, she hung up...and felt the blade of a guandao touch her throat.

"In my own way," said a voice. "Crap," she thought.

Meanwhile, Louis slid his cellphone into his pocket and started on his way. "Alright Vortech, start the music!"

"Commencing Evard Grieg's greatest masterpiece in 3...2...1 now!".

Louis proceeded to beatbox and do a little dance to the music. He thought the tuba sounded a little bit realistic, but he brushed it off.


Louis eventually made it to Everfree Row, a dismal place that was reminiscent of New York's Chinatown...or was it Little Italy? Anyway, it was not a good idea to peruse its streets at nighttime, unless said idea was a death wish, because that was like doing a police raid without any Kevlar: it's practically an invitation saying, "Here I am, come and do your worst." But Louis was careful and no one dared to break into his two story house; the last one to try had her goose roasted by the dragonesses, figuratively that is. His house looked more like an oversized shed with more windows, a garage on the bottom level, and a pantry, 2 bedrooms, a bathroom, and a kitchen right next to the living room (in fact, you could say that the kitchen was part of the living room) on the top level.

When Louis entered the house and got upstairs, he found an interesting sight: Emerald was on the floor, muzzled, her wrists and ankles bound, and another dragonesses looking over her with a guandao aimed at her midriff.

This dragoness was smaller than Emerald and was a lighter shade of green mixed with yellow, a black and dark olive green bra top over her B cups, and a pair of shorts the same color. Louis cleared his throat. "Peridot, what are you doing to your sister?"

The dragoness called Peridot immediately threw down her guandao. "Boss!" she cried. "I had no idea how long you'd be, so I, uh, figured we pass the time," she laughed nervously.

Louis placed his palm on his forehead. "Untie her" was all he could say; it was all he had to say to get Peridot to release her sister. When she was done, the dragonesses turned to face him. "Now, as you know, I do have the job, but it may require me to be living in a dorm over there."

Peridot raised her hand. "But Boss, if you stay there during that 'special time of the year,' you'd be wiped out."

"She's right, Master," said Emerald grudgingly, "we're two females; who knows how many female students can even control theirs?"

"That's why I figure that you two need to help me hatch an escape plan," said Louis, "but work on that over the semester. Peridot, you prepare dinner, Emerald, you see if the bed is up to tonight's after dinner part of the celebration, and I'll freshen up."

"Yes Master/Boss!" said the sisters eagerly. While Louis and Peridot went off, Emerald sniffed the air. There was a scent that she didn't recognize, a scent that was out of place in this neighborhood. She prowled out of the house to find the owner.

Louis hadn't seen this because he was in the bathroom, taking a shower. When he came out in a white bathrobe, his damp hair askew, he noticed that she was gone. "Peridot, where did Emerald go?"

The dragoness looked up from her cooking and smirked seductively, "I don't know Boss, but she won't know what she's missing."

Louis gave her the same look Heath Ledger gave Christian Bale approximately 10 years ago. "You didn't truss her up and lock her in one of the closests, did you?"

Peridot spluttered, "Of course not Boss! I was here the whole time! But," she saw a weird shape outside, "that might be her."

Louis followed her gaze and saw that she was right: Emerald was out there...and it looked like she was hog-tying someone. Louis brought his palm to his head again. "I swear, if I was a few decades older, you two would be the cause of my high blood pressure!" Before Peridot could say anything, Louis stormed out.


Emerald had just finished securing a red bandana when she footsteps and a metallic clunk. She looked up and saw her Master walking towards her, clad in nothing but a bathrobe that was... barely doing its job at the bottom. Oh it covered what it was suppose to, but barely. Anyway, he was clutching a long wooden walking stick with the the end on the ground being a metal tip that was emitting the clunk. She got up, her wings twitching; she could hear the inhale her prisoner breathed, meaning she saw him too. Emerald started to speak, but Louis hoisted his stick up so that the metal tip was aimed at her throat, then knelt down to the hogtied pony.

She had a light gray, artic blue coat, brown tail and mane, light heliotrope eyes, a white jacket topped with an F-clef pin covering her C cup chest, and grey pants. There was a sousaphone near by, although he didn't know what it was for, but if he had to guess, this pony knew how to play it. He unwrapped the bandanna from her muzzle and said, "Now what are you doing way out here?"

She looked around nervously before saying, "I was just minding my own business after a quartet rehearsal when I saw you dancing and muttering gibberish to yourself-" (Emerald snickered; Louis hefted the stick closer to her throat and told her to raise her hands) "-then I heard some strange music in the air. Before I knew it, I had my sousaphone out and was playing along to it while you watching you shake your...posterior. When I was able to stop, we were already in this atrocious neighborhood."

Emerald couldn't deny a little growl at that, although it was ambiguous if it was that she considered the mare's words an insult or if she agreed with her. Louis, meanwhile, slowly brought his finger tips to his forehead. "I thought the bass sounded a little too real." He could hear Vortech laughing, but decided not to comment, so he looked at the mare. "What is your name?"

"Beauty Brass."

(Yes, she's canon. See?)

She wasn't having her "best night ever."

"Well, Beauty Brass, you may find this hard to believe, but you are in the company of the only decent inhabitants of this 'atrocious' neighborhood. Out there," he gestured to the gloomy street, "is full of misty...micey...mice gin...miss gin...sexists-" (I can't say it either) "-who would take advantage of you, and do unspeakables to you."

Brass whimpered and clung to her sousaphone, "Is it ok if I spent the night with you? I don't mean to impose, but-"

"But of course!" Emerald was right in front of Brass in an instant, shaking her hand. "We rarely get any visitors around our humble abode."

"Now now, Emerald," chuckled Louis, "give her some space. We only just met her, after all." With that, they escorted the mare inside.


Peridot was ecstatic to have someone visit, but Brass didn't like the smirk on her face...for that matter, neither did Louis. But it passed, and the four settled down to eat, and oh, what a feast: meatloaf for Louis, chicken a la king for the sisters, and Caesar salad for Brass. Eventually, it was time to turn in for the night. There was a bit of a problem. "There's two beds and four of us," said Peridot. "The Boss usually sleeps with one of us while the other sleeps in the other bed. There is one of the couches, though-"

"Well, thanks for volunteering to sleep there, Peri," interrupted Louis and he snapped his right fingers.

Peridot could only register the sound as well as that rare name before she felt her feet being tied together. "Now wait a minute, Boss, can't we talk about this? I mean, I didn't tie you up." A coil of rope appeared and secured her hands together. "If this because of what happened with my sister, she won't accept apologies because those are overrated. Wait a minute." Before she could rethink that statement, a third coil of rope appeared and wrapped itself through her mouth, then her muzzle. The now bound and gagged dragoness tipped over and began squirming, only stopping when Louis picked her up, plopped her onto the oddly shaped couch, and head into the master bedroom.

Brass caught a glimpse of Louis without a shirt on before he closed the door and blushed. Emerald saw this and smirked. "He punishes us by trussing us up and not 'riding' us, as it were. It's not a fate worse than death, but it does feel like it, especially during that 'special' time of the year." Brass' face went redder than ever as Emerald escorted her to the guest room.

Emerald was a little late coming to bed, because she was holding her machete and cutlass to Peridot's throat and belly; she stopped after catching sight of an underwear clad Louis and following him into his room, leaving Peridot to struggle against her bonds and gag while the Lego piece sat on nightstand, the voice laughing as if its owner could see her futile resistance.

Author's Note:

*NOT a reference to The Lego Movie, more towards the wiki page that says her chitin is very dark grey.

Peridot's apparel was inspired by this lady.

Louis' last name is a reference to this guy.

Join our Patreon to remove these adverts!
Join our Patreon to remove these adverts!