On behalf of Princess Celestia of Equestria, your presence in Canterlot for an audience with Princess Celestia of Equestria is requested. Travel has been arranged for today at Noon.

“O-Oh My! What could this mean?” Fluttershy asked herself, looking the immaculate handwriting over for a third time. She couldn’t believe that the princess wanted to meet with her. Maybe it was to ask her to tend the Canterlot Gardens, or to ask her to take care of Philomena while the Princess was off on diplomatic business. No, it was probably to punish her for ruining the garden during the Grand Galloping Gala, or to scold her for somehow hurting Philomena. Oh well, at least she knew that the Princess was fair… if that was in fact a good thing.

Fluttershy began obediently packing her things, and trying to imagine what the Princess had in store for her. Her thoughts flip-flopped between positive and negative outcomes, but she couldn’t figure out which one was more likely. She had a natural talent for gardening, but so did a lot of other ponies. She had done a lot of things that the Princess might have found annoying, but she didn’t do anything that Pinkie Pie or Rainbow Dash hadn’t bested, or is it worst-ed? She visibly shrank as the chariot pulled by two burly royal guards appeared.

“Are you Fluttershy?” the closer of the two guards asked, his voice far louder than necessary.

“I… Um… Y-Yes… If that’s okay, I mean.” The yellow Pegasus pony said, shying behind her hair

“May we take your baggage?” the second guard asked as the first pulled out of his harness.

“N-No… I can get it, I mean, if that is um… I’m sorry…” Fluttershy mumbled, the guard picking up her two bags anyway. He placed them in the chariot and ushered her into it wordlessly. She followed his instruction and sat in the lonely, roomy interior.

The trip was a fairly long one, for a trip to Canterlot. The Ponyville weather ponies had been preparing for a large storm, and the guards had to fly at low altitudes to prevent any disturbances. When they arrived, Fluttershy had worried herself into a fitful state. She was shivering with worry as she dismounted the carriage, and she walked cautiously through the spacious halls of the castle. She was told to meet the princess in one of the castle’s tower-suites. It was a long walk through the desperately lonely halls; the only creatures visible were the ever-present royal guards that seemed to be in front of every other doorway. Every time a pair of them set their steely gaze upon her, she instinctively sped up. She reached the suite, which was surprisingly unguarded, and walked up the long spiraling staircase. She reached the top and entered to see the Princess of Equestria herself relaxing on the bed as she read some royal correspondence.

“Hello, Fluttershy. I’m so glad we could meet.” The princess said, in a tone neither happy nor sad, simply a tone indicative of her earnest appreciation of their meeting.

“U-Um… H-He… Hi,” the meek little pony said.

“I bet you wonder why brought you here.”

“Actually, um… before that… If it’s okay… I’d like to apologize for whatever I did… if I did something. Did I do something?” Fluttershy stumbled, her reaction eliciting a chuckle from the Princess. Celestia rose from the bed and walked over to the pony, who accidentally fell onto her forelegs and began quivering.

“No, my little pony. You did nothing that requires apology.” Celestia said, watching Fluttershy go from panic to mild intimidation. “Yet” she finished, smiling. She paused for a second, some sadistic part of her enjoying the panic she was causing until her conscience compelled her to set the record straight. “Don’t worry. I was just kidding. I've brought you here harboring no ill intent, my little pony.”

“T-Then did I do something g-good? Or okay? I-I'm sorry... I'll be quiet now."

“Among the myriad of wonderful things you have done, I actually am meeting with you to ask of you one more deed of kindness.” The princess said, circling Fluttershy. Her motions would normally intimidate someone as meek as Fluttershy, but the way she carried herself seemed to be calming in a way the smaller pony didn’t understand. “I have a very special job for you, and I know that you are the perfect pony for the task.”

“I-I am?” Fluttershy asked excitedly, a small blush spreading across her face as she realized she had unconsciously been staring at the princess’s flanks, her vision unconsciously focusing on the area between her thigh and tail with every circle.

“Yes. Because you are a very mature pony, and I know that there are things that are happening to you that you don’t understand. I know why you have been staring at my rear like that…” the Princess said, almost seductively

“Princess! I have no idea what you are talking about.” Fluttershy exclaimed, hiding her face behind the forelock of her mane.

“I’m sorry. I didn’t anticipate that my bluntness would have that effect on you.”

“Oh, I um… I blush a lot. I’m sorry. …a lot of things embarrass me. I-I'll try not to be so embarrassed, if you'd like” Fluttershy said, trying her best at a smile, despite the rose shade of her cheeks.

“I didn’t mean that, my dear.” Celestia said, smiling and meeting the pony’s gaze, “I was talking about your absolutely adorable wings…” Fluttershy craned her neck around to find her wings at full attention, something that had only happened once before to the now terrified pegasus.

“A-Ah! I’m so sorry. T-That’s so embarrassing. Rainbow Dash told me that this means that you want to ...to," she froze momentarily, assembling all of her courage, what little bit remained, "…have sex.” Fluttershy explained, her lower eyelids twitching with the first signs of oncoming tears.

“It’s entirely okay, my dear Fluttershy. There is a time in everypony’s life where things like this happen. Trust me, I’ve seen worse happen.” Celestia mused, “Like the one time that colt drop… Never mind that, it’s a story for another day. Anyway, I want to make sure that someone will have the preparation to deal with the other ponies’ problems as they come of age, and seeing as you are the eldest in your group…”

“Y-You want me to do this?” Fluttershy asked, nudging toward her wings.

“No, there is a little more than that to it…” Celestia said, “Let me show you, if you don’t mind,” her voice almost seeming to playfully mimic Fluttershy.

“Well… um…” Fluttershy said before the Princess reached out and applied pressure to the axillaries of the timid pegasus’s wings. “Oh princess!” Fluttershy exclaimed, entirely forgetting her previous thoughts. Her brain went crazy. This feeling was better than anything. Better even than being with her friends. “W-What are you doing?”

“I’m merely showing you what I want you to learn.” Celestia explained, her hooves working out kinks in the pony’s spine that only years of low altitude flying can create. “Oh my, you are so tense. Let me work some of these out.” Fluttershy felt years of cramps and soreness melt away at the princess’s touch.

“Oh, Princess. This is magical!” Fluttershy said, her once meek and quiet voice abandoning her for a loud and almost confident variant, gears inside her clicking into place as a long-dormant part of her psyche was put into action “Could you do more of this, if it’s okay with you, that is?” Fluttershy felt all of the pleasure she was feeling converted directly into confidence, creating a feedback loop of power that left her feeling ten feet tall.

“Certainly. I have to give you at least some training myself. Who knows what those crazy ponies in Ponyville would have you doing, especially that Rainbow Dash one.”

“Oh, Um. I suppose.” Fluttershy said, silently excited, her wings stretching as much as their membranes would allow as the princess finally moved away from them.

“Now what I am about to do is something that you can’t do to everypony. This is something you should only do with ponies that you like very much. Of course I am just demonstrating so…”

“Do you like me very much?” Fluttershy asked optimistically. The princess paused, somewhat confused. She was about to answer when she looked into the smaller pony’s eyes and saw the pure unbridled hope therein.

“Forget this stupid ruse! Yes I like you. Why do you think out of all of the ponies in Equestria, I chose you to teach how to please a mare?” The princess said, her own wings flaring out as she eyed Fluttershy’s damp plot longingly. “I’ve seldom met a pony, let alone another mare, that has really caught my eye like this. It's taken a considerable amount of resolve to establish this somewhat weak pretext before having my way with you. I have no idea why I feel like this”

“Why no other ponies make you feel this way, or why I do?” Fluttershy asked, beaming.

“The second. There have been two other ponies that have caught my eye in similar ways. My sister Luna has a special place in my heart as only a sibling can, and my dear student Twilight Sparkle never ceases to show her devotion to learning. But you give me this feeling deep down, ever since you apologized to me after the Grand Galloping Gala… It was in your voice. And then it was in my dreams, and for months I couldn’t keep you out of my mind! I've seldom felt this desperate.”

“O-Oh My. Really, Princess?”

“Yes, my dear. Now let me please you! I’ve been waiting for this for almost a year. I apologize if I'm a little overzealous, but even I need to let go sometimes.”

For the next several hours and into the night, the entranced princess gave the little pony the most extensive education on all things pleasurable. Fluttershy, emboldened by the princess’s lust for her begged the princess to stay with her, despite their collective exhaustion. Celestia agreed, and they slept in each other’s embrace.

“Good morning, Princess!”

“Ah, Good morning, Luna…” the princess said, opening her eyes, “Wait. Where am I?” she asked, realizing that she was not in her royal chamber with her sister. Her gentle smile instantly disappearing as she froze momentarily, even her mane static for several long seconds.

“I-I’m not Luna… But if you um… if you want, I could pretend…” said the smaller pony, already awake and staring down at the most royal of countenances, still emboldened by her previous engagements.

“Oh, Fluttershy. That won’t be necessary.” The princess said, grinning, “I was really hoping all of that hadn’t been a dream.” The yellow pony looked away and stiffened a little.

“Well… um… Princess, I-It was very real…” Fluttershy mumbled, her tail swishing back and forth idly as she tried to maintain her composure.

“In that case, I do believe that you do deserve to be thanked.” The princess said, entranced by her total recall of the last night. She gently escaped her sheets and rose to her hooves.

“But I barely did anything! I-I would prefer to earn my thanks… I-If you don’t mind.”

“I’m not sure I’m going to be able to handle more of that just yet.” The princess said, taking a deep breath. “You gave me the best night of my life. Of the hundreds of encounters I have had of a sexual nature, you are of the very few who have satisfied me, of the even fewer who kept pleasing me after they were satisfied, and the only one ever to well… I’ve never used my horn that way.”

“Princess, I only did what you asked… until the horn part that is… It just um… seemed right.” Fluttershy explained. “If anyone deserves thanks, I think it should be you… I learned so much… and I have never felt so good…”

“Well, I think I may have more to teach you if you wouldn’t mind coming back sometime to spend… a week or so here?”

“A-A week? As in like seven days? T-that would be a long time. I’m not sure if I would be able to take that much…”

“I would like to try it sometime. If that is okay with you…” The princess said meekly, playfully imitating her new student.

“Anytime, my princess.” Fluttershy promised, giggling to herself at the role reversal.

“But I regrettably will have to leave you. I have a sun to raise, and a very busy day. I hope that I am not leaving you too abruptly.”

“N-Not at all, Princess. But if you wouldn’t mind, Would you maybe... I mean... could I possibly get a... g-goodbye kiss? Please?” Fluttershy asked, feeling that confidence from earlier starting to wear away.

“It is the least I can do.” The princess said, walking over to Fluttershy and placing her muzzle against the smaller Pegasus pony’s. The world spun for Fluttershy as she watched the princess walk slowly away. She was issued one final command as her lover and teacher left. “I expect you know what to do when you get back to Ponyville…”

Author's Note

Now rewritten a little bit. Hopefully this will iron out/explain some of the previously unprecedented character dynamics, and hopefully establishing Flutters' sexual confidence in a more concrete and acceptable way.