3: Progress and lunch.
Even if Derpy wrote that she just taking a nap on the note she left on the kitchen, she actually overslept. She didn’t feel very good, what Tailmon told her was weighting in her mind, she knew deep down that all the digi-cat said was true to an extent.
She has been truth to her word and didn’t show any hint of kindness in her behavior, everything she has said has been mean and rude. Derpy tried to play it out has just being edgy, but the more she thought about it the more it downed on her that Tailmon was actually a ruthless individual with no compassion or empathy in her heart.
Maybe she shouldn’t have insisted Tailmon to help her. Derpy considered Tailmon’s words, and she thought like Tailmon said before she was being a hypocrite, it saddened her to no end to consider something so mean as the truth, but the evidence was there.
Maybe Tailmon would’ve been better with any other pony or even nopony, her hostility and the way ponies look at her made clear the incompatibility between them.
It is the same feeling Derpy herself gets from some ponies in occasions, she feels left out, empty and alone due to nopony understanding her and treating her differently just for something out of her control.
Derpy didn’t want to get up anymore, what was the point of it anyways? She would get out make her route, ruin somepony’s property by crashing into something or simply being yelled at for being her.
Yet nature made its call and Derpy had to go attend to her needs downstairs, she sighed and begrudgingly made her way to the bathroom.
It was late on the night so everything was almost pitch black in her way there, but it was strange, she didn’t step on as much trash as she usually does when she walks inside her house, something was off. But she shrugged it off as just being luck on her part.
While inside there, she wondered what did Tailmon do all day, was she even in the house anymore, has she abandoned her like all the other ponies have done before? Derpy could just wonder what ifs at this point, but she wouldn’t hold it against Tailmon if she did just that, Derpy doesn’t want to ruin Tailmon’s day anymore.
Stepping out of the bathroom she couldn’t help the sobs from escaping her, she knew feeling this way was wrong, but she didn’t want to be alone anymore. The only thing she wanted was somepony that would treat her like a normal pony, even if Tailmon was aggressive, she didn’t masked her words behind petty sentences, Tailmon was honest, truly honest, painfully honest with her. This was more than what she gets from other ponies, it was a silly thought to feel complimented by something like that, but this was the case for Derpy.
She smiled sadly at the darkness around her, “I really am an idiot aren’t I?” she whispered to herself as she made her way back to her room upstairs to sleep some more.
Meanwhile in the castle of friendship Twilight was asking Konata for some information about the individual her mother sent to watch over Tailmon.
“Sorry Twilight, I have no idea of who mom sent there, it could be anyone really, and white furry legs with three toed feet are not that rare around here I’m afraid,” Konata told to her friend crushing her hopes of learning anything useful for the current situation.
“Can’t you ask her to tell you?”
“Can’t do sorry, we asked her to give Tailmon a chance, she would not budge to any other request unless there’s something for her to gain out of it, and considering the situation I don’t see what gain she could get.”
Twilight’s mood deflated like a balloon, but she was still determined to get something out of this conversation, “in that case… can you tell me something about Tailmon?” she asked innocently.
“Why do you want to know?” Konata asked back not really understanding why she would ask something like that.
Twilight coughed into a hoof to clear her throat, and adopted a professional stance, “I would like to learn about her species, how do they operate and common likes and dislikes, it would help us a lot if we can understand how she functions.”
“Oh, then it’s better if you ask that to her instead of me,” Konata told her killing her chances of learning something once again.
“Why can’t you tell me?” Twilight asked with a little frustration.
“I don’t know that much about her Twilight, also if your objective is learning in general terms you can make Tailmon tell you, since it would be considered a request and Tailmon has to do them if she wants to get positive points,” after Konata said this Twilight regained some hope back.
“Really?” Twilight got a nod as response, “well, if you put it like that it makes sense, thank you for clarifying it.”
“You’re welcome, and I’m sorry for not being able to help you more Twilight but I have my hoov…erm… hands tied, jeez you guys rubbed on me way more than I anticipated,” Konata let out a light hearted laugh.
Twilight just giggled slightly in amusement, “sorry for that, and I know you just left this morning but we already miss you, especially Pinkie and Rainbow even if she doesn’t want to admit it yet.”
Konata just smiled at that, “well, Twilight it is nice to know that you learned how to use Magical Vision so fast you really are a good student,” she complimented getting a slight blush on Twilight. “Once again sorry for not being of much help, but now we are in a little bit of a busy time on here so I have to go for now, we’ll be in contact soon, I’ll be seeing you later.”
“It’s ok, thank you for the help Konata, and good luck,” Twilight waved with a smile before the communication ended.
Being left alone in the darkness of the throne room except Twilight began to plan on how to formulate the request for Tailmon.
Konata waved back as the transmission ended, she let out a sigh afterwards.
‘I’m sorry Twilight, but I can’t help you with this,’ Konata thought to herself.
A giddy giggle was heard behind her, “how does it feel to lie to your friend?”
“This is your fault mom, you made me lie to her,” Konata replied with some hostility.
“You can’t blame me for being fair, you wanted a chance for Tailmon to redeem herself, I’m giving you one, so deal with it,” this was Mihoshi’s reasoning behind this.
“But you just had to send her, didn’t you?”
“She was perfect for the job, and she proved it quite fast I admit.”
Konata couldn’t argue with that logic, yes the one who her mother sent was doing her job properly, but it still annoyed her, “whatever,” with that she turned to leave her room.
But her mother stopped her when she passed by her side, “you better calm down.”
“I’m calm, just make sure nothing happens to them, or things will get messy,” Konata got the hand of her mother off her and walked off.
Shaking her head disappointedly, Konata’s mother followed behind to go somewhere else, ‘kids these days…’
Next Morning.
Derpy woke up the next morning when she felt an inviting smell, rubbing her eyes she got out of bed and went downstairs.
With the light of the sun lightening the room her eyes widened at the scenery, the floor was devoid of trash; her sticky furniture had no remains of muffins or some miscellaneous food that she decided to eat at some point in time, the walls, the ceiling even the stairs were clean, not sparkly clean but at least the filth on them was no more.
She went to the kitchen, where the same thing happened. All the muffin batter and rests of food in the sink and on the corners of everything weren’t there anymore.
Tears were escaping her eyes, “who…” her voice cracked some but then noticed a note on the fridge.
She read it out loud, “Look, I accepted to help you in your house, and that’s what I’m going to do, you don’t have to thank me Gray. I’m no cook but I left you some tea and cookies so you don’t go to work with an empty stomach, if you see this note it’s because I’m getting rid of all the trash on the house. I don’t know what happened or care about it, but don’t go doing this again, or I’ll beat you up.”
“Kitty…” Derpy couldn’t believe her eyes; she left the note on the table just next to the tea Tailmon made for her. With a shaky hoof she took a sip of the tea, “it’s so good!” she exclaimed loudly, tears of happiness falling all over the cookies, but she ate them anyways, “these are salty, but still good!”
“They aren’t supposed to be salty, you’re crying all over them you idiot,” Tailmon said from the kitchen door.
Derpy stopped with her mouth full of cookies and looked at her, she tear up even more, “kbffity!” she spat out some nonsense and cookie crubs everywhere as she made her way towards the digi-cat where she proceed to catch her in a hug.
Tailmon took a couple of seconds before saying the following, “get off me! You’re getting crubs on my fur you idiot!” she yelled as she tried to pry off Derpy, but she wasn’t really trying too hard to do so.
Some hours after that, Derpy was in a very good mood and prepared herself to go to work, got her mailmare uniform on and was about to leave, but Tailmon called her.
“Gray,” Tailmon got closer, for some reason she was wearing a plain blue apron she had a little box in her paws, “here,” she held the box in front of Derpy so she could grab it.
“Huh?” Derpy was confused, “what is this? Kitty.” She asked while grabbing the box.
“Lunch,” Tailmon plainly said.
“Lunch?”
“Yes, lunch. For what I saw while cleaning this dump you have not being eating correctly for a while, so there you go, I will get in trouble if you go fainting somewhere when I’m supposed to be helping,” Tailmon explained.
Derpy smile heartwarmingly, “Thank you Kitty!” she gave Tailmon another hug.
Surprisingly Tailmon gave her some pats on the back, “alright, alright, enough hugs, go to work before I have to drag you there,” she said getting a look from Derpy, “I’ll do it even if I don’t know where it is.”
Derpy resumed her way to work, Tailmon closing the door behind her.
Inside Tailmon had a satisfied smile on her face and turned to go do something else, before suddenly stopping, “what am I doing?” she questioned, but shrugged it off soon after, “whatever, I’m hungry so off this apron goes,” she said tossing the apron in some random direction where it neatly landed on the couch.
Tailmon went to the forest to look for a certain something.
Twilight having finished her request for Tailmon to do was in her way to Derpy’s house, she was expecting the place to be some kind of ruin by now. But what she found was unexpected; it was very clean, even the exterior was cleaner than the houses next to it.
‘Strange, was Derpy’s house always this clean? I don’t remember it being this way before, but I never really visited her ever so I’m not sure,’ Twilight thought to herself.
She knocked at the door, but nopony answered, she waited there some more knocking every once in a while but still nopony attended the door.
Twilight just sat there, ‘maybe there’s nopony at home?’ then another thought crossed her mind, ‘or did something happen…? No, if something happened it would have been reported already by that one creature,’ she let out a sigh, ‘Calm down Twilight, don’t go into that dark place yet, Tailmon has to behave or else she won’t get what she wants, so she wouldn’t do something so reckless at least for now.’
Tailmon came back from the forest with the thing she went there to look for inside a plastic bag and saw Twilight at the door; a devious thought came to her. She went behind the house and with a jump she got to the roof, then she put a claw inside the bag until it was drenched with a red substance, she placed herself in just the right angle so her claw was on top of Twilight making the dripping of the substance fall directly on the unaware alicorn.
On the distance the mysterious figure wrote everything on her notebook, “Tailmon has done some progress, but she should learn how to behave at some point,” she murmured with disappointment.
I'm sure 101% of the people reading this has figured out who the mysterious one is, but I'll keep playing it out as mysterious just because is funnier that way. 
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I thought Kari's Japanese name was Hikari. And who is Rinna?
9383797
That is indeed Kari's japanese name, but you're assuming this Tailmon is the same Tailmon from digimon adventure, when it's not. As for who Rinna is, well she's the main character from this story's prequel "My Little Baker."
D'aawwwwwwwwwwwww, some more
This was both heartwrenching and heartwarming at the same time. You know how to capture Derpy's emotions.
Also, naughty Tailmon is so naughty.