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Part 1 of The Sometimes Terrible Life of Crowley's Secretary
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Published:
2025-05-05
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2026-02-28
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6/?
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The Terrible Life of Crowley’s Secretary

Summary:

There comes a time in anyone’s life where they seriously consider selling their soul for money, but don’t do it. It’s not worth it.

Working at night raven college has been nothing but a nightmare for Asper who only took the job because no one else would hire him. Now he has to deal with an incompetent headmaster and a troublemaking set of students. Will he make it to the end of the school year? Or will he forfeit life because we all know Crowley won’t let him quit?

Chapter 1: Prologue 1

Notes:

This is my first fic that’s seeing the light of day, so if there’s anything I can improve on please let me know! The idea for this fic popped into my brain when I was trying to find something to read involving twst and a secretary but I couldn’t find exactly what I was looking for so I decided to write it myself. If there are any fics like this PLEASE TELL ME SO I CAN READ. I crave dopamine and this is the only way I can get it at the moment.

(See the end of the chapter for more notes.)

Chapter Text

I regret applying for this job, and I would like to apologize to everyone who told me it was a bad idea. I was very wrong.

At the ripe age of 23, I was severely broke and needed a job, so I went for the highest-paying one: working as a secretary to the principal of Night Raven College. When I say I regret this decision with all my being, I mean it’s only been 5 years, and I already look forward to the day I retire.

First of all, my boss is a lazy dickhead who always pushes everything on me. EVEN THINGS I LEGALLY CAN’T DO. Secondly, the students are way too aggressive and get into trouble too often for me to handle. The last three years have been especially bad. All of the dorm heads have crazy issues. I wouldn’t be surprised if Crowley suddenly made me get a degree in therapy, because something is seriously wrong with these kids.

I can only hope this year will be better. Or I’ll die and be able to finally rest. Ha ha ha…

 

____________________________________
ENTRANCE CEREMONY, MIRROR CHAMBER

“Hello, Dormheads,” I said without looking up from the clipboard I wrote on. I may hate my job, but I still begrudgingly spoke to everyone in a kind tone, even if I didn’t always look at them while I spoke. “You may find your seats off to the side. I have sectioned off the area so students will easily be able to navigate to their dorm’s section after being assigned by the Mirror. Once the ceremony is over, please go to your respective sections and proceed as previously explained,” I continued, only briefly looking up, then making myself look busy by doodling.

“Thank you very much, Secretary,” Dormhead Rosehearts bowed. He’d always been the most polite out of the other dormheads, but I heard he’s pretty nasty to his students. Still, it’s nice for someone in this school to respect their elders for a change.

On the other hand, a certain dormhead seemed to completely lack the ability to respect anyone. As I was drawing a duck on my paper, my clipboard was forced out of my grip.

“My, my Secretary. Is this what you do with such a serious face?” I didn’t even have to turn around to know who was behind me. The high body heat of a beastman and a lazy, amused voice could only mean Leona Kingscholar. With his chest pressed against my back, he hummed as he looked over my drawings some more.

“Kingscholar, this is highly inappropriate behavior,” I said with a strained smile. “Please return to the task at hand.” ‘And get the fuck away from m,e you creep,’ is what I wanted to say, but the employee in me prevented that from leaving my mouth.

“Oh? And I could say the same to you,” Leona leaned into my ear even more at my discomfort. “By the way, these doodles are pretty bad. Good thing you’re a secretary,” he laughed.

“Leona! Unhand Secretary Asper!” Riddle’s face grew red in anger. This is just another reason why he’s such a good kid compared to the rest of the dormheads, because everyone else was either laughing to themself or not paying attention at all.

Glancing at my watch and realizing time was running out, I swiftly grabbed Leona’s arm and pushed it behind his back, pushing hard enough to start hurting before I let go. In his confused state, I grabbed my clipboard out of his loosened grip and backed away.

“Ooo feisty. Who knew you could actually fight back?” He mocked before heading to his designated seat, where everyone else besides Riddle had already migrated.

“Sigh,” I rubbed my eyebrows, a habit I gained after only a month working this job.

“Secretary Asper, I sincerely apologize on behalf of my fellow dormhead,” Riddle bowed deeply.

“Please don’t apologize on behalf of Housewarden Kingscholar, you are not at all responsible for his actions,” I patted Riddle’s head without thinking, immediately retracting it when I realized what I was doing.

Riddle bolted up at the affectionate touch I figure he’s never received in his entire life, with the trauma he probably has. His face was red again, but this time not with anger.

Turning around, I returned to the tasks at hand. There was too much time wasted, and still lots to do before new students could arrive.

 

____________________________________

 

As the fresh meat filed into the large chamber, I realized one was missing. Walking up to a blissfully unaware Headmaster, I leaned in and whispered to him.

“Sir, we appear to be missing a student,” I said, hiding my face from the crowd with my clipboard. “Would you like me to look for them, or–”

“No, no, I’ll go hunt him down for I am so benevolent,” he exclaimed a little too loudly, running out the doors. At first glance, you may be thinking it really is kind of him to search for the student instead of making me do it, but in reality, he didn’t want to have to tell a crowd of feisty children that they have to sit still for a while.

Sighing, I went to the dormheads one at a time and explained the situation to them, hoping they would be able to tame the children themselves.

Standing in an empty corner, shaking my leg and biting my nail, frequently checking the clock, I waited for the headmaster to come back, but it was taking way too long.

I was so worried, I didn’t even notice when Leona approached my side, shirking his duties of keeping his new students under control.

“What are you doing here, Kingscholar?” I said without a hint of kindness in my tone, finally realizing he was standing next to me after a few minutes.

“Too loud over there,” he yawned in typical Leona fashion.

“You chose to be a dormhead, so you have the responsibility to care for your ‘subjects’ as you like to call them– shit,” I quietly interrupted myself when I bit my cuticle so hard it started bleeding.

“Hm,” he hummed, sniffing the air and glancing at my finger without emotion.

Before he could say anything, the Mirror Chamber’s doors swung open with a loud clang. Beside him was what must’ve been the missing student, and in his arms was a… tanuki? …cat? Whatever it was, it could only mean bad news.

Leaving Leona and forgetting about my bleeding finger, I practically sprinted towards Crowley. Once I was next to him, he handed me the tanuki without any explanation. Feeling resistance from the creature, I held it tightly. Who knew what could happen if this thing went loose.

Facing the confused student, Crowley said, “Step up to the mirror to be assigned a dorm. My secretary will watch your weasel.”

The creature growled at that as Crowley pushed the unwilling child forward.

“State thy name,” The dark mirror echoed.

“Yuu…”

“The nature of your soul is… unclear to me.”

Fuck. Of course, something went wrong from day one. The mirror continued that they sensed no magical power from the child or something, but after realizing what hell awaited me this year, I couldn’t pay attention. That is, until I felt flames burn my skin.

Releasing my grip, I realized the tanuki got away and started causing a scene. *Sigh*, this was going to be a lot of paperwork.

Ignoring the severe burn on my arm, I approached the disastrous scene. There was fire everywhere in an instant, and Crowley tasked Riddle and Azul with the capture. It was almost painful to watch them run around trying to catch the thing, but I couldn’t be bothered to interfere. Though adrenaline was still kicking in me, my arm was starting to hurt, and I didn’t want any further injury to hinder my ability to quickly complete my upcoming paperwork. I figured I wasn’t going to be getting any sleep that night.

Eventually, they were able to capture and eject the monster while I got rid of the fire in the room. I was basically moving on autopilot at this point. Everything went so horribly wrong that it broke me on the inside. It took so long to put all of this together and try to account for anything that could ruin the ceremony. Apparently, I didn’t take into account a magicless alien and a speaking cat that breathes fire. Sue me.

After the poor, confused child was denied access to their home, Crowley came up to me, who was instructing the ghost janitors.

“Asper, I have taken it upon myself to do the very kind deed of helping this poor youth find a way home in the library,” Crowley put his hand on his heart. “Paperwork’s on my desk,” he continued without any of the previous benevolence. There he goes again, taking the easy task and giving the hard one to me. It wasn’t as if I hadn’t expected this, so I was already mentally prepared to pull multiple all-nighters.

Only staying long enough to see a quick nod from me, Crowley dragged the alien away.

 

Due to the workload, I took some time before going to the office to get a cup of coffee. The kind of coffee that would kill anyone over the age of 65. I lost count of how many shots of espresso were thrown in there, but if it kept me awake long enough to get through this, it’s worth it.

With my new cup of liquid death, I started the trek from the kitchen to the Headmaster’s office, where I spent more time than the actual headmaster.

On the way, I ran into a very busy-looking Crewel. All the teachers and staff (except Crowley) were incredibly busy preparing for the new students. What shocked me was that despite this apparent busyness, the teacher approached me.

With only the dim light of magic-powered torches, we were both prevented from seeing the extent of each other’s tiredness, but we both knew we were exhausted.

“Hello, Asper, has Crowley given his tasks to you again?” Crewel started the conversation in a kind tone. Out of everyone on the staff, Crewel is my favorite. If I suddenly decided to quit, the only one who could convince me otherwise would be this man.

“Haha, yup,” I replied. “The entrance ceremony was a complete train wreck, so of course it’s my job to push it under the rug. I swear I have so much practice doing that from this job that I would fit perfectly into an illegal gang,” I joked without a joyful tone. While I’d never been completely myself around anyone in this building, Crewel is the one I’ve come closest to doing so. If I were less worried about making him continue to like me, I would do just that.

“I swear, puppy, you never know how to say no,” He interrupted my thoughts.

“Haha, if I do that, who knows what kind of blackmail he’ll pull. He’s worse than Ashengrotto when it comes to that.” I may have sounded like I was joking, but I wasn’t. He has pulled that shit on me before. Two years ago, I asked to quit, and he said no while sliding a thick folder in front of me. After that, I haven’t even tried to refuse what he tells me to do. Who knows what he has in his stockpiled blackmail on me? If there’s information on certain times in my life, I might as well be done for, because I would lose everything.

“If you ever need any help, let me know. I’m not afraid of the crow like you are,” He patted me on the arm, earning a harsh wince. It seems I had forgotten that a layer of my skin was seared off. Crewel took in my reaction and looked closer at my arm. The sleeve of a jacket supposed to be there was mostly gone, leaving my skin exposed. Even in the dark, it was easy to see the burn.

“Puppy,” Crewel continued in a stern voice. “Explain.”

“Oh, uhm… It’s a long story, but basically a monster got in with an alien student and the mirror chamber went up in flames…” I replied, trying to keep an ounce of the previous joking tone. If I actually explained the entire situation right now in detail, it wouldn’t be pretty, and I would lose the little bit of Crewel’s trust I have.

“Hahhh,” he sighed, rubbing his eyebags. “We’ll discuss exactly what you mean by that later. For now, let’s get you to the nurse's office. You can go back to work after that.”

 

My new bandages made work a bit more difficult, but there was nothing I could do about it. Crewel and the nurse would collectively beat my ass if I even thought of taking them off, so I lived with the strain.

 

____________________________________
HEADMASTER’S OFFICE

“Pardon me,” A voice could be heard past the knocking on the headmaster's door. When there was no answer for a few minutes, the voice, along with the group he was with, entered.

“How irresponsible of Headmaster Crowley to not answer, despite the scheduled meeting,” Another voice was heard as the door opened.

What they saw when they entered was not an empty room nor a negligent Headmaster, but a desk stacked with papers, almost completely hiding a passed-out secretary.

“Oh? It seems someone never went home last night,” A voice among the group sounded, who was obviously Leona.

“Ug,h that sleeping arrangement is terrible for his skin,” Vil complained, approaching my exhausted self. “Come up, now. Don’t forget we have a housewarden meeting.”

“Yes,” Riddle approached my other side. “Please awaken, Secretary Asper, lest we fall behind schedule.”

The loud voices caused me to stir until I finally opened my eyes. Blinking out my sleep and adjusting to the light, I looked at everyone, confused.

“Huh…?” I grumbled. “Why are you all…”

“Ahem,” Azul interrupted. “Due to how painful this is, I will explain. We arrived due to our scheduled meeting with the Headmaster, but the one we found instead was you, who seems to have fallen asleep in the midst of paperwork.”

“Yes, it is rather unsightly,” Vil handed me a handkerchief. “Please wipe the drool from your face.”

I did just that while processing the information. After getting past the haze of sleep, I sprang up, finally properly aware of the people around me. ‘This isn’t good,’ I thought, ‘how dare I let myself be seen in such a vulnerable state by these people?’ I gathered my papers and started to walk towards the meeting room.

“My apologies, dormheads. If you would please follow me, I will begin the meeting. Headmaster Crowley will arrive shortly as he had previous business,” I sai,d regaining my composure and polite tone. Before I could walk far, a well-manicured hand grabbed my shoulder and forcefully turned me around.

“At least button up your shirt all the way if you want us to forget this happened,” Vil scolded with a slight smirk on his face, making fun of me.

“Oh yes, *cough*, my apologies.” I turned back around to lead everyone to the meeting room, hiding my embarrassment.

Out of my sight, the dormheads smirked at each other at this new, indispensable memory that they shared.

 

____________________________________

 

To make it short, Crowley never ended up coming to the meeting. It wasn’t the most important meeting, but it was still frustrating. So far, the day was going horribly, which wasn’t a good sign.

Today was orientation, where new students would go to their classes to get a brief overview and to get comfortable with their schedule. The students were to go to shortened classes to make a half day, and then get a tour of the campus by the staff. The number of students meant we did not have enough living teachers to lead the tours, so I was put in charge of a group. In the group I was leading, there were a few standout students.

The first one I noticed was a small, incredibly pretty boy who could only belong to Pomefiore. However, despite his looks, his mannerisms were quite rough. ‘Poor kid,’ I thought, ‘Vil’s going to rip you apart.’

In reality, this kid probably hates being called cute or pretty, just like I did when I was younger. Nowadays, though, the overwork has done away with most of my charm, so it’s not an issue.

The other student I noticed was a massive beastman who must’ve been the second-tallest person in the school. There was no doubt he was from Savanaclaw with how burly he looked.

During the tour, I put on my usual kind facade. Out of every staff member in the school, I was the one who had to do that the most. I wasn’t from any excellent family or was a world-renowned scholar, so if one of these kids complained to their parents about me, I would be done for. Plus, it’s always nice to practice my acting skills and pretend to be the only nice person in the school. It’s really good for the main character complex, y’know?

Luckily, since it was still only the first day, there were no real troublemakers in the group, other than some people trying to wander off. I may be pretending to be nice, but I will never act like a pushover to the students of Night Raven College, or they would eat me for lunch, so of course, I stopped anyone from leaving the tour.

 

“Alright, everyone. That will conclude our tour. If you have questions or concerns, feel free to ask any of the staff members or your dormheads. If you ever wish to speak to me specifically, ask a staff member to lead you to the secretary's office,” I spoke as I rehearsed in my head. “For the rest of the day, you are all free to roam the campus until curfew.”

My mouth hurt from smiling, and I was being weighed down by the 2 hours of uncomfortable sleep I got. I was so ready to book it and relax alone in my office, but I was stopped by the pretty freshman I had noticed earlier.

“‘Scuse me, sir,” a harsh accent said. “Name’s Epel Felmier n ah was wonderin’ if ah could switch dorms.”

“Hello, Mr. Felmier,” I smiled, “May I ask what dorm you’re currently in?”

“Pomefiore. And ah wanna be in Savanaclaw. Ah don’ fit with them pretty boys in my dorm,” He answered. Oh yeah. He was definitely going to have his soul ripped out by Vil. I would want to switch too.

“I see. It is possible for students to switch dorms, but it is required that you spend at least 2 weeks in your current dorm. After those 2 weeks, if you still wish to change dorms, you’ll need a signature from your housewarden and the housewarden of the dorm you wish to transfer to, along with mine and the headmaster’s signature as well,” I said, ruining the poor child’s hopes and dreams. ‘He won’t get very far with Vil as his housewarden, which is good for me.’

“Oh…”

“Now, if you’ll please excuse me.” Finally, I was out of there. It may have been annoying to be interrupted, but my mood brightened at the sight of such a dejected child. There’s no better delicacy than seeing someone’s confidence wither away. I would’ve laughed right in Epel’s face if I had less self-control, but I’m supposed to be a kind and polite secretary.

Wait. What?

 

____________________________________

 

Back in my office at last, I lay down on the couch I purchased with my own money last year. Actually, almost everything in this office was bought with my money. When I first entered this position, the crow placed me in a room a few doors down to his office. At the time, all the room contained was a lone desk and chair dead center. The walls were bare, and so was the floor, but at least the large windows on the side wall made up for the lack of decoration.

Nowadays, the room is slightly more comforting. My sofa and coffee table are relatively new additions, but are both items I couldn’t live without. They face the window so I can gaze outside and forget I’m in my own slightly fancy prison cell. There is a large rug under the sofa to separate that area of the room from the other half that holds my desk and documents. The desk is further back in the room and to the side, so it’s no longer dead center. Behind the desk, lining the entire wall, is a bookshelf that holds reports, important documents, and books I read during breaks.

 

As the cushions of the soft couch sank me in, I couldn’t help but close my eyes under the warm sunlight. I had a blanket close by due to the many nights I opted to sleep here rather than trek to my room on campus, but I was already asleep before I could think of getting it.

It only felt like a second passed when I heard my door slam open, waking me immediately. Seeing as the wonderful sunlight blanketing me was no longer there, more than a few hours must’ve passed, but that wasn’t enough time for me. Without trying to kill the Crow with my glare, I sat up.

“What?” I said with a nasty tone. Working closely with the Crow for 5 years means he’s the only one I don’t have to fake a smile around. Of course, I still do as he says, but I don’t look happy. After he slid that blackmail folder to me years ago, I lost all will to hide my personality from him. At this point, I’m sure he’s dug up enough that he knows who I am better than I know myself.

“Calm yourself, Asper~ remember who pays you,” He replied. He may be attractive under that mask, but I’m crowphobic, and this triggered me.

“Yeah, better give me overtime pay ahead of time based on this ‘exquisite’ entrance from your ‘benevolent’ self. Answer my question.”

“Haha, of course, of course. Well, a few students caused some mayhem, and now I would like for you to write up their expulsion letters!”

“That’s not as bad as I expected. But what exactly did they do to warrant expulsion on their first day?”

“They broke one of the magic powered chandeliers in the cafeteria…” He trailed off, knowing that the detail he left for last was the worst one and would piss me off the most.

“There it is,” the actual workload. I stood to follow Crowley to his office, making a list of everything that now had to be done and adding up hours on my workday. So much for sleep.

 

____________________________________

 

“We did it, we have the mage stone!” Three freshmen slammed open the headmaster’s office and ran in. Dirt and a little blood were noticeable on their clothes and skin, along with a strange, dark ink that looked like it would stain for weeks.

Knee deep in paperwork, I looked at the three without expression and slowly turned my head to Crowley, subtly glaring at him, knowing there was something he hadn’t told me.

He avoided my piercing gaze but was also surprised by the freshmen’s entry. “Wow, you actually found one? My secretary was almost done writing your expulsion paper!”

My glare became stronger as I lost the willpower to save face in front of three strangers. “Crowley, what did you make them do?” I said without respect.

The trio looked at each other, watching the drama before they went on to explain.

.
.
.

The number of times they spoke about almost dying made my grip on my pen so strong that it snapped by the time they finished.

“OHHHH THIS IS SO WONDERFUL,” The crow screamed, putting on an act of wiping tears that weren’t there, making me and the children wince. “NEVER IN MY YEARS HAVE I SEEN MY STUDENTS WORK TOGETHER!!!!”

“STOP YELLING,” I cracked. My ears were especially sensitive due to my desperate need for sleep, and I couldn’t take it anymore. Usually I’m able to hold back my nasty personality in the presence of other people, but the trio were obviously glad I told him off, because I saw their relief when their eardrums no longer got harassed.

“You, Yuu, must be a beast tamer!” He continued…

While that whole encounter meant I didn’t have to finish the expulsion paperwork, due to this ‘beast tamer’ quality, he decided to officially make Yuu and his cat, Grim, a student. And you know what that means… More paperwork for me! Of course, I still had to finish figuring out costs for the chandelier because that’s my job for some reason. Seriously, what even is Crowley’s job?

He sent the kids off after his long spiel, and after a while of silence after the door closed behind them, he spoke again, gathering his things, “Wel,l look at the time, I'd better get going! Be a dear and finish that paperwork in your office. I don’t want to come back to a mess tomorrow. Ta~ta”

“Wait–” he vanished before I could stop him. I finished the paperwork in his room just to spite him and to make sure I didn’t give up before finishing. I was determined to sleep in my bed at least once this year.

 

I speedran that paperwork fast enough to drag myself to my room at 12 am. Making it outside, I bumped into the most terrifying person on campus, Malleus Draconia. Unlike most people, I’m not so scared of his powers, but I am afraid of his status as the next king of Briar Valley. When he first arrived at the schoo,l I figured I wouldn’t see him much because he’s a recluse, but since I’m the secretary and Malleus is never at meetings, I’m in charge of relaying information, so we’re more familiar than I would want.

Bumping face-first into his chest, the laws of forces did me dirty because I immediately started falling backwards. I was ready to fall on my butt until I felt a tight grip on my shoulder from the man in front of me.

“Are you alright, Secretary?” He said in a somewhat concerned voice. While I would usually be a nervous wreck interacting with him, I was too exhausted to even process that the whole thing wasn't a dream.

“Hm? Oh. Sorry, Mr. Draconia,” I slurred, rubbing my eyes and looking up, not noticing how he still didn’t let go of my shoulder.

“Why are you walking at this hour? It is much too late for you, children of men, to be outside. Lilia told me children of men get kidnapped at this time,” He continued as I unconsciously leaned into his cold grasp as I dreamed of sleep.

“Don’t worry, men don’t usually get kidnapped, and we’re on campus. I’m walking back to my room after finishing work.”

“Lilia said that as well, but your appearance may be deceiving in that regard.”

“Haha, with the amount of sleep I’ve been getting? Kidnappers would be scared away just by looking at me,” I joked, trying to finish the strangely long conversation so I could finally sleep.

He looked at me with disbelief, “If you wish to believe that, then I will not stop you.”

“Oh, right, I have to fill you in on what happened at the housewarden meeting today…” I began with my eyes half closed, almost leaning half of my body weight into him now.

“You may do so another day, Secretary. You are too tired as you are right now to do so with a clear mind,” his voice softened. “Pardon me,” he said before green specs swarmed around us, and I was suddenly lying on my bed, Malleus nowhere to be seen.

Notes:

If you made it to the end, thank you! I fully do not expect anyone to actually read this. My ultimate goal is to write the story then completely forget everything that I’ve written and then read it as if I’m not the author.

If there are any real people reading this then I want to apologize because there’s no chance that this will have a steady update schedule. Depression hits hard.