The Student's Freedom

by E11imist

First published

When Spike falls ill, Twilight is delivered a letter which will have some big repercussions.

When a letter from Celestia urges Twilight to be her own pony and find love, she begins to see and experience things that she never knew were there.

Chapter 1

View Online

Derpy awoke with the sun streaming through the window. It seemed like it would be a beautiful day, but then again the weather service had said it would be. The grey pegasus began her morning routine of a muffin followed by a quick sip of water, she absent-mindedly checked her appearance in the mirror and glanced at the clock.
The clock on the wall showed 8:15.

She was already 15 minutes late! The boss would not be happy, although he had seemed to be generally okay with the fact that she had dropped a piano on Ponyville's most magical unicorn, so he probably wouldn't make too much of a deal out of this. Derpy remembered the day so well; when she had first noticed Twilight Sparkle and started to watch just what she was doing, first out of curiosity, then out of an odd fascination. She had seemed like such a nice pony, having just moved here from Canterlot she obviously wasn't very familiar with all the earth ponies and how this small town functioned. She didn't seem to enjoy the time at the party much, even less so after Nightmare Moon had showed up, but that was completely understandable.

Derpy had wanted to go and introduce herself, and offer Twilight a tour of Ponyville, but she was very self-conscious about her eyes and wasn't exactly sure how much Twilight would like the idea of being hanging out with somepony like her.
As time wore on, Derpy's interest in Twilight grew as she saw all the really awesome things that she had accomplished. Defeating Nightmare Moon, getting rid of the Ursa Minor and the list went on.

The grey pegasus blushed as she remembered her first encounter with Twilight Sparkle, and thought that it really wasn't a good first impression to accidentally drop heavy objects on the purple unicorn's head. Derpy could see just fine, she had just gotten distracted while watching Twilight in her wheelchair/mobile-sickbed.
The eyes were usually the first thing most ponies noticed about Derpy, and that was a big factor in why she didn't have too many friends. This was also why Derpy was a mail carrier; there wasn't a whole lot of personal time with other ponies and it seemed to work well that way.

Derpy arrived at work and apologized to her boss and went about her job as she always did. However today was going to be different, she just had this feeling it would be.
And wouldn't you know it, on her third delivery for the day she notices that she has a package for Twilight Sparkle! Derpy chuckled as she realized that sounds like a line from a bad adult movie. "Get your brain out of the gutter, Derpy." She remarked to herself.
She arrived at the big library in a tree, and knocked on the door. The library didn't have a post box so she had to make sure Twilight got it personally.
The purple mare herself answered the door. "Morning, Twilight!" Derpy said, almost a bit too enthusiastically. "Oh hi…" Twilight replied, trying to think where she knew the mare from. "Derpy Hooves," the grey mare completed. Twilight tried not to stare at the mare's eyes, wondering which one she should look at when talking to her.

"Anyway I have some mail for you," Derpy said, "Strange that you don't usually get mail."

"Yeah, Spike has been sick and it has made corresponding with Princess Celestia quite difficult. So now we just use the post until he's better."

"Oh, well I guess this is from the Princess then." Derpy said, flipping the letter over to see the return address.

"Indeed, thanks for bringing this by, Derpy, I'll see you around."

"See you, Twilight."

Twilight closed the door, thinking about how strange it was that she had never spoken to Derpy before, "Perhaps she's self-conscious about her eyes?" Twilight wondered. "I sure would be." Still, she supposed the mare had a sort of charm to her, like somepony who was happy with life, and didn't care that she was different.
Twilight looked around the library, surveying the chaos that had been steadily building since Spike had gotten sick. The place was a disaster; it looked like Rainbow Dash had hit it while attempting to land. She sighed and went to check on Spike.

She hesitantly opened the door, not wanting to disturb his sleep. The little purple dragon was sleeping like a rock, and snoring like a landslide. She sighed and let him sleep, things were difficult without him, and Owlowicious wasn't of much help when it came to packing away hundreds of books.
Up the stairs she went, to her room. She levitated the letter in front of her and opened it in the air. She recognized the writing of her favourite teacher and started reading.


My faithful student

I am sorry to hear that Spike is still sick and I wish him a speedy recovery. While I am glad that things are otherwise well, I have been thinking about your stay in Ponyville and when you first decided to live there on your own. This brings me to my point.

You have told me about your experiences concerning the magic of friendship dutifully ever since you have moved to Ponyville. I feel you have learnt much about friendship, and I am completely content with only hearing from you every now and then, so please, Twilight, feel free to send me letters as frequently – or infrequently – as you see fit. It is no longer necessary for you to tell me about your adventures, but I will still welcome your reports as I always have.

This is not an easy letter for me to write, Twilight, but I feel you have grown up so much ever since you have left Canterlot and I want you to be free to experience everything the world has to offer. I specifically encourage you to find love and happiness with another pony, for there are few things as magical as love, and I wish for you to discover this for yourself.

Forever your loving teacher
HRH Princess Celestia


Twilight dropped the letter in disbelief, choked back her tears and read the letter again until she completely understood everything that her teacher had imparted upon her. This was more than just a shock to Twilight, this letter was life changing, she realized. She couldn't remember a time when Celestia hadn't been there to talk to her about… well anything!

Wait, Twilight thought, this might not be all that bad! She cringed inwardly as she remembered her mental breakdown involving the Want-it Need-it spell. That surely wouldn't happen again. In an academic sense, Twilight had graduated! So many emotions where whirling around in her head, sadness and joy and freedom and possibilities. She needed to do something to help her relax.
She immediately started to write down a plan she could carry out concerning the Princess's new suggestion of finding love.

Operation TwiLove:

1.Find somepony I am interested in.
2.See where it goes. If I find love, great, if not, well then we try again.

Twilight immediately saw a problem with her plan. "There is nopony I am interested in!" She thought aloud. With increased worry she realised she had never been interested in anypony, nor had anypony ever been interested in her. This did not bode well.

She needed a friend's advice, someone more experienced in this area.

"Rarity!" She exclaimed, while Spike thought the same thing, far off in his dreamland, only not nearly with the same intention that Twilight had.

Chapter 2

View Online

Out the door, down the street, off to Carousel Boutique. She passed that strange looking purple pony with the loopy eyes who always had her hoof in her mouth, usually just twiddling her lips and making foalish sounds.

“There’s one in every town…” She said to herself.

It wasn’t long before she reached the Boutique; she peered through the windows and saw Rarity lying on her sofa with a glass wine levitated next to her. She was obviously distressed. Twilight to the rescue!

Twilight burst through the door, making Rarity leap off the couch and almost forget about her wine.

“Twilight! You startled me! I was umm just taking a break!”

“Rarity, don’t you think it’s a bit early for wine? I mean even for you…”

“I have no idea where you find the proof for your ungrounded implications Twilight, but I assure you I am far from an alcoholic! I just needed to relax a bit, to take my mind off work.”

“Oh, I suppose everypony needs a break.”

“Yes, now not to sound rude, but what are you doing here?”

“I have some very interesting news.”

“Ooh! Please, sit down and tell me everything.” Rarity said, now interested in the potential gossip.

“This morning I got a letter from the Princess, telling me that I don’t have to report on friendship anymore and that I should go and find happiness for myself, with another pony.”

“Wait, the Princess told you to go out and meet someone?”

“Well not exactly, it was more of a suggestion… She just wants me to be happy.”

“And you came to me because you thought…”

“I don’t know, I thought you would have some advice for me.”

“I find it flattering that you would think of me Twilight, and I do find myself free from work at the moment, so please, feel free to ask me anything.”

“Great!” Twilight smiled, happy that she had such a good friend.

“Okay, so the Princess said that I should find love with another pony, but I don’t think there’s anypony that I like, and I seriously doubt that somepony likes me.”

“Well, Twilight, perhaps you should lift your head out of the books more, I’m positive that there are more than a few ponies in this town who would simply love to go on a date with you.”

“Really?” Twilight blushed.

“Oh absolutely darling! Applejack recently mentioned that Caramel mentioned how simply breathtaking you looked the other day when you walked into Sugarcube Corner.

Twilight blushed a deeper shade of crimson. “Really, Caramel? I always thought he had a thing for Applejack… Also Caramel used the phrase ‘simply breathtaking’?”

“Well I may have paraphrased just a bit, I believe he used the words ‘hot damn’ when you entered.”

“That’s good I guess? I wasn’t even trying to draw anypony’s attention that day…”

“Well Twilight you have to be careful. Not everypony out there is like you see in films. Oh! The horrible dates I’ve had!” Rarity exclaimed as she melodramatically raised a hoof to her head, as if to keep herself from fainting. “Also watch out for the ones who seem too perfect, they may just be acting so nice to get you… well… in the sack; and then the next morning they are gone without so much as a goodbye.”

“Relax Rarity, no-pony said anything about getting in the sack. I just want to find somepony I like and who likes me back, maybe go on a date; let’s not worry about that sort of thing just yet.”

“I suppose you’re right Twilight, although I really cannot help you if no-pony piques your interest.”

“You’re right, thanks for the chat Rarity, I think I have a better idea of what I want now.”

“I’m always happy to help Twilight. If you need any advice, you know where to find me.”

“Thanks Rarity, I’ll talk to you later.”

Twilight left the Boutique, now with a much better idea of what she wanted. “I’ll just make myself more approachable from now on.” She thought to herself. “I mean how hard can it be?” On her way back to the library she trotted past Lyra and Bon-Bon walking flank-to-flank. “They seem so happy, and yet they are both mares… I haven’t really considered whether I like mares, stallions or both. Can you even be interested in both? Is there someone in Ponyville who swings both ways?” The questions continued as she carried on back to the library. She needed to rethink her strategy, and figure a few things out.

“Spike! I’m home!” Twilight announced as she entered the library. Spike comes running down the stairs, obviously much better since this morning, “I wasn’t sleeping!” He loudly says in his own defence. “I didn’t say you were but thanks for clarifying that. I’m glad you’re back on your claws again. Could you make me some tea please? Thanks.” Spike grumbled something about how dragons never worked like this in the old days and if he were just a few years older he wouldn’t even be able to hold something so small without breaking it in his hands.
Twilight went to her room and added to her plans.

Operation TwiLove:

1. Find somepony I am interested in.

2. See where it goes. If I find love, great, if not, well then we try again.

Addendum: In order to find somepony I am interested in, I should find out what kind of pony I like. (Mares and/or stallions?)
How do I find out? I suppose I’ll just have to try both!

“Seems like sound logic,” Twilight thought. “Only I don’t know where to begin… ARGH!!! Why does this stuff have to be so complicated?” Twilight shouted at the ceiling, throwing a book at her nearest bookshelf.

“Uhm, Twilight can I come in?” Spike asked, as if he were dealing with volatile explosives. “Oh, sure Spike, just set the tea down there by the bedside table.”

“I know this may not be my business but you’ve been acting kinda weird since that letter Derpy delivered yesterday.”

“Well Princess Celestia basically told me to go live my own life and that I no longer have to send her letters.” Twilight grumpily admitted.

“You don’t sound happy with your freedom…”

“I don’t think I am, Spike. Things were simple last week. Suddenly I have to figure out so many different things I barely noticed before.”

“You’re smart Twilight, you’ll figure it out, you always do. And you always have a number one assistant and 5 great friends to help you.”

“Thanks Spike, but I really don’t think this is something you can help me with. I’m probably just making too big a deal out of this anyway.”

“I think you should consult your books. I mean it’s not as if you’re the first pony to struggle with, well whatever it is you’re struggling with.”

“Oh Spike you always know just what to say. Thanks for being such a good friend.” Twilight said as she pulled the little dragon into a hug. “Go relax for the rest of day, I have a few things to sort out.”

“Thanks! I think I’ll go visit Rarity.”

Twilight didn’t say anything, not wanting to shatter his dreams; it made sense that he’d figure it out for himself eventually and Rarity wasn’t the type to be cruel.

Twilight lay down on her bed, not realizing how tired this day had made her until now. She easily slipped off into her dream world, where things were always better.

Twilight awoke to the sound of somepony knocking on her window. She got up to go see who was so secretive not to use the front door. Two strangely pretty yellow eyes and a friendly “Hey Twilight!” met her. “Hey Derpy, why are you here?” “Oh I was just wondering if you wanted to make out.” “Huh?” Twilight stared at the grey pegasus in confusion. “You know, like this.” Derpy said, then settled onto the window ledge and pulled Twilight closer. Twilight was powerless to resist as Derpy held her in her legs and began softly kissing her. The purple unicorn just went with it, kissing back without restraint as it started to grow more forceful until they were joined at the muzzle, exploring each other’s mouths.
Twilight loved every single moment of it, and she started to pull Derpy towards her bed, her blood running hot through her body.
Derpy looked at Twilight with a seductive smile and then whispered in her ear, “Wake up, beautiful.”

Twilight’s eyes snapped open to find that she was still in her bed and that her window was closed, the early morning sun streaming through with no grey pegasus anywhere. She felt wetness between her haunches and a hot feeling in her face. “Well that was…” She paused as she tried to think of a suitable adjective. Amazing, arousing, alarming… “I guess I am more than partial to mares,” she thought to herself. “And apparently I have latent feelings for Derpy…” She mumbled as she got up.

There was a knock at the door and Twilight walked downstairs whilst combing her hair.
She opened the door to find the same pony she had been making out with just minutes ago standing at the door with a letter in her mouth.

“Hey Twilight!”

Chapter 3

View Online

Twilight stood frozen in shock. She considered the possibility that this might be a dream again and kicked herself lightly. Nope. This was real. Twilight was bright red by this stage and desperately thought of something to say. “Uhhh hey, Derpy, who… what’s goin’ down?”

“I don’t know, what?”

Twilight cringed inwardly as she realized the second meaning of her question. It was a stretch, and you’d have to be a real gutterbrain to make the leap, so she considered herself safe. Also she silently applauded herself for sounding so “street” as ponies say. Her composure almost regained she spoke more comfortably.

“Oh nothing, just uh, well yes nothing.”

Derpy was oblivious. “Well I don’t have mail for you today, but wanted to ask whether you could recommend any books about heterochromia?”

“I think I might have one, do you know anypony with it?”

“Well I recently bought a parrot, and I wanted to know whether the whole 2 different eye-colours thing could be relevant to his health.”

“I don’t think so, but it wouldn’t hurt to find out. Come in and I’ll see if I can find it.”

“Thanks Twi! Can I call you Twi?”

“Uhhm, yes.” This is so great, she thought, nicknames mean familiarity right?

Twilight located the book and levitated it over to where Derpy was standing, staring at all the books. “So many books…” she thought aloud. “Well it is a library.” Twilight responded. “So uhh Derpy, I was kind of wondering…”

whatamIdoingwhatamIsayingwhatisthis

“Yeah Twi?”

“If you wanted to…”

shutupdontdothisyouareinunfamiliarterritorySparkle

“Uh huh?”

“Come with me to Pinkie Pie’s party this weekend?”

whathaveyoudoneTwilightthereisn’tevenaparty

“Sure! Pinkie has the best parties in town! So I’m your plus one?”

“Yeah… something like that.”

“Great! I’d love to go with you, Twi!”

“Fun, so uhm I don’t know the details yet, but I think it’s this Saturday.”

welldoneidiotnowyouhavetogetPinkietothrowapartyintwodaystime

“Cool, I’ll just go ask Pinkie about it.”

“No wait don’t! Uhh, I’ll just tell you tomorrow, you can come see me again in the morning on your mail route.”

“Sweet! So I’ll see you tomorrow then?”

“Yeah, I’ll just go talk to Pinkie about the party. See you Derpy.”

“Bye Twi!”

Twilight closed the door behind her and threw herself on the couch. “That was possibly the stupidest thing you have ever done.” She spoke to herself. Despite the fact that she had just lied her way into a party that didn’t exist, (yet) she felt sort of proud that she had actually asked out a mare she liked. “Wait, do I like her?” She thought, “Well duh! I mean I did just ask her out…ish. I don’t think a party counts. Anyway, I have to go convince Pinkie to throw a party.” She chuckled as she realised that that certainly wasn’t the hardest thing to do.


------------------------------------


She quickly left the library and trotted off to Sugarcube Corner, Pinkie Pie was usually working this time of day, if you could call eating one cupcake for each one she sold working. Still Mr Cake certainly didn’t seem to mind; he probably liked to see a little bounce when Pinkie walked away. Slightly perverted tangent aside, Twilight reached Sugarcube Corner and entered with the hopes of turning her dumb idea into a party, surely there was nopony more qualified than Pinkie to do just that.

The bell above the door rang as Twilight entered and alerted Pinkie of the visitor’s presence. A big grin spread across Pinkie’s face as she saw her friend. “Hey Twilight! What are you doing here? Do you need muffins, cupcakes, pies, cakes or any other sort of baked deliciousness?” She was clearly happy to see her. “Uhh hey Pinkie, nothing like that today, I actually wanted to ask you a favour.” “Ooh! Let me guess, you want me to bake you a cake for a special occasion, wink!”

ohsweetCelestiasheknows

“Wait what? How do you even? No, I just wanted to ask you if you were going to host a party this weekend; and if you weren’t, to persuade you to do so.”

“But of course I will silly! I hadn’t planned on it, but a party this weekend sounds like the bestest idea ever! There’s gonna be punch, music and streamers and the whole thing is gonna be a blast!”

greatshedidn’taskwhy

“So why do you want to have a party this weekend? Besides the obvious fun we’re gonna have.”

damnyourstupidsupernaturalpowers

“No reason! Any excuse to party, right? Also could I bring a guest? If it’s not too much trouble…”

“Sure, this is a party for everypony! Who do you want to bring? Is it Colgate? I bet it’s her, she has this really great smile and she has a cool mane and…”

“No Pinkie, it’s Derpy Hooves, or Ditzy Doo, or whatever her real name is. She just seems kinda lonely and I think it would be a good idea for her to meet some of our friends.”

“Oh sure! I’ll invite Colgate anyway.”

“Okay, it’s your party… So Saturday? Around 7ish?”

“Perfect, I’ll get started on the preparations. What am I saying, I’ll just break out the party cannon! It’s such a blast at parties!”

“Indeed, thanks so much Pinkie. I knew I could count on you!”

“I would never turn down a party Twilight! I’m so super happy to have helped you out! So I’ll see you Saturday at 7 sharp, and don’t forget to bring Spike, even if it’s just for a few hours.”

“Great, I’ll see you then Pinkie. Thanks again.”

“Bye Twi!”

Twilight left the confectionary with a smile; she was so lucky to have such awesome friends.


------------------------------------


Back at the library Twilight found a book that seemed to fit her situation perfectly. Crushes, Dating and the Single Young Mare: Everything you wanted to know about dating but were afraid to ask.
Twilight had dismissed it as sensationalist stupidity at first, but then sadly admitted that she really needed all the help she could get.

-Introduction-

You are probably reading this because you need advice. You also probably have a crush on somepony, if you doubt whether or not that’s true; you need to ask yourself:

Does this pony make your heart beat faster?
Do your words run out around this pony?
Do you find yourself constantly thinking about this pony?

If you answered yes to one of these questions, you probably answered yes to all of them. You have a crush, and you would like to date this pony, wouldn’t you? Well this is just the book for you, together we’ll cover everything from dating etiquette to kissing to the happenings in the bedroom.

Twilight read on until the sun was far in the west, and the night started to creep in. She fell asleep with the book by the side of her bed and she dreamed of dating, kissing and happenings in the bedroom. All of this featuring her favourite grey pegasus with bubbles on her flank.

Chapter 4

View Online

Time flew faster than the neutrino particles Twilight had been reading about. She had casually told Derpy about the party at Pinkie’s and that she would meet her there at 7. Derpy had seemed very happy to hear the news and had told Twilight that she “can’t wait for Saturday.”

Saturday afternoon at 5 PM Twilight looked in her mirror. A nervous and cute purple mare looked back at her with a queasy smile. This wasn’t something to be worried about, but she still couldn’t help it. What if she makes a complete idiot out of herself? Scenes of the Canterlot Garden Party flashed through her mind. Her dancing had seemed like an ultimate form of upper-crust repellant, but they did end up having a lot of fun that evening. Twilight hastily consulted her copy of Crushes, Dating and the Single Young Mare: Everything you wanted to know about dating but were afraid to ask.

Confidence is a single mare’s best friend.

“Hmm, well that’s a very concise way to put it,” Twilight thought aloud. She supposed she would just have to fake it and hope for the best.

---------------------------

Meanwhile among the clouds, Derpy had been preparing for the party too. It wasn’t a big deal, but she had really started to enjoy her morning conversations with Twilight. Even when there wasn’t much to talk about Twilight always had some random and funny fact to throw out there.
Derpy hadn’t read too much into the invitation, but for a mare that rarely socialised outside her 5 friends, it probably wasn’t easy to ask someone as optically challenged as herself to a party.

---------------------------

Pinkie was an energy bomb that exploded whenever the doorbell rang. Twilight would have to remember to tell Fluttershy that it was indeed possible to explode twice.

“Hey Twilight! How are you? Are you excited? Cause I’m excited...”

“Pinkie! Yes I am very excited! Who else is here?” Twilight knew where this conversation usually went so she had learnt by now that it was a good idea to simply interrupt her enthusiastically.

“Well Gummy is here, but he seems kind of overdressed, don’tcha think?”

Twilight looked over to the toothless alligator in his tuxedo. She suppressed a laugh and looked back at Pinkie, who seemed to think this was the most normal thing in the world. Loud dubstep was thumping inside and she could see lots of lights and ponies dancing.

“See, Twi! He thinks this is a fancy dress party! He’s so random sometimes...”

“Uhm, yeah I guess so... Is anypony else here?”

“Yes! Rainbow Dash has been here since 5, she really seems to like it here. But where are my manners, come in and meet everypony!”


Twilight walked in and saw that Pinkie wasn’t lying when she said “everypony.”
There was a barrel of cider suspended above the punch bowl, which Twilight suspected had basically become a cider bowl. EuroBrony was playing loud on the speakers and even Vinyl Scratch had even showed up to DJ. Twilight scanned the crowd for Derpy, and found her grooving slightly offbeat and waving her hooves in the air, which reminded Twilight a bit of her own style. She did her best version of hybrid dance-walking towards Derpy and playfully bumped her with her flank. Derpy fell over on her face in a very unceremonious manner and managed to pull Twilight down next to her. But rather than seem angry, she seemed pleasantly surprised.

“Hey Twilight! When did you get here?” She screamed - while still lying on the ground - over the music into Twilight’s ear.

“Just now!” She screamed back, “I couldn’t help but see you dancing so...” Twilight frantically searched her vocabulary for a semi-appropriate word. “energetically.”

“Hehe, thanks I guess, by the way was it you who knocked me over?”

“Uhm, yes.” Twilight confessed while she hoped that she wasn’t blushing visibly.

“It’s okay, do you wanna get up and dance some more?”

“Sure!” Twilight smiled.

They both continued to dance in their own weird, spastic way. To an outsider it must have seemed something like a fun and coordinated epileptic fit. Finally, when they were both too tired to gyrate any more they retired to the cider bowl.

Berry Punch was passed out next to the table in the recovery position. They both carefully stepped over her and poured some cider. Derpy led Twilight outside by the hoof, where they sat down next to the bakery.

“So Twilight, what convinced you to invite me to a party before it was organised?”

“What, what, where did you even?” Twilight fumbled for words as she nervously scratched the back of her head.

“It’s okay Twi, Pinkie may be the best secret keeper, but she’s also the best non-secret teller. She told me when I delivered her mail that Twilight had just the great idea to have a party this weekend. This was after you invited me, so I guessed that Pinkie didn’t know about it when you invited me. Also you confirmed my guess when you blushed like a tomato just now.”

Twilight chuckled nervously, “Yeah, well I guess I did.”

Derpy turned to look deep into Twilight’s eyes and said: “Well I’m very glad you did.”

Twilight turned a redder shade of crimson, but held her gaze.
“...” words were not forming.

“Twilight.”

“Yes?” She swallowed nervously.

“Do I have to wait for you to kiss me or am I gonna have to do it?”

In a moment of sheer unprecedented impulse Twilight took the lead and grabbed the strange grey mare and kissed her like she had been wanting to since she had woken up ever so disillusioned from that dream starring the same wall-eyed pegasus.
This is what the book was talking about, everything melted away until all that remained was her and the pony she was kissing, locked together in total infatuation.
The kiss lasted both forever and no time at all, and when it was over Twilight was feeling both exhilarated and filled with longing.

Nopony spoke for a while, until Derpy broke the silence.

“Wow, just... wow.”

Twilight gave her an eager smile and said: “Shut up Derpy.”

They kissed again and again, until their mouths hurt and their tongues were tired.

Derpy finally broke the kiss and asked:
“Do you want to date? See where this crazy chemistry takes us?”

Twilight nodded stupidly and said,
“Only since the moment you knocked.”

To be continued