Fluttershy's Lessons in Friendshipping

by juicebox

Chapter 2: Good Night Moon

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“Oh, you’ve been a naughty filly indeed…” Luna said, knowing that Fluttershy wouldn’t hear her. She trotted down one of the halls of the Canterlot castle toward her quarters. She wasn’t going to let such …talent… go to waste. Especially on her sister. Luna couldn’t understand what the white puffball wanted to know about sex, that was HER realm. The princess of the night, nopony had sex during the day, except for the strange ones. Even her very own sister shrouded her exploits in the cover of darkness.

She was going to have her. Sex was not something which the darker sister took lightly. If she didn’t have Fluttershy, no one would. She readied a few things before taking off, unaccompanied, towards Ponyville.


Fluttershy had just returned from a long day with Rainbow Dash. Fluttershy didn’t mind helping Dash practice flying, especially when Dash was rather affectionate on breaks, but it took a toll on the yellow Pegasus. She just couldn’t keep pace with Dash. Normally, she would just sit there quietly until Dash crash-landed or something. Today, however, Dash seemed distracted, she made mistakes even Fluttershy wouldn’t have made.

Tired would have explained how the Pegasus had felt if the morning after her most passionate lovemaking session wasn’t replaced by cheerleading duty. As the timid pony went back to her house, she had to force her hooves to leave the ground. She could have fallen asleep at any point, but she knew that the animals needed their food. Angel would be so worried …er angry. As she approached her home, she noticed that all of the animals were staring at her, Fluttershy knew they weren’t stupid, but how could they know? She put out their food before entering the house, but all of the animals avoided it until she went inside. Fluttershy thought nothing of it.

The mare passed by the damp area on her floor, still slightly smelling the intoxicating smell of Dash. She shuddered both in shame and longing. She was embarrassed by their passion, but wanted more. She would clean up the mess tomorrow, maybe. Tonight she needed some rest, and that was just one set of stairs away. She climbed the stairs and approached her room. The door was cracked open. Usually it was tightly shut; Fluttershy wouldn’t want the animals to see some of the more …interesting devices… that the bedroom hid. A mare had to get off somehow, and there was no way that she could have asked some stallion, not that she didn’t appreciate their appeal.

As she mused on how unlikely it was that Angel had found her carrot-shaped vibrator she failed to notice one key thing as she entered her room. Instead, she was caught off guard by the open window. The curtains fluttered in the moonlight. Fluttershy groggily approached the window and was caught in awe when she looked out over the night sky. How dark it was, an enveloping, tangible darkness. How each of the million stars seemed to reach out to her with its own song.

And then she saw the moon. She always loved nature, but there was something about tonight, and definitely something about the moon. It’s as if it was staring back at her. It wanted to talk to her. It wanted her. Fluttershy shook off the strange feeling and started to turn around.

“I feel the same way, Fluttershy,” said a strange voice, “I spent a long time on the moon, and I still can’t get enough of it.”

The tired yellow Pegasus was shocked by the sudden voice, yet held entranced by it as well. Needless to say, she was speechless as she slowly turned around to see the Princess of the Night lying on her bed.

“It’s intoxicating. I take one look at the land that imprisoned me for a thousand years, and even in the face of my loneliness I can’t help but be taken aback.” Luna said, her voice soft and lulling, “There is a reason why ponies reserve intimacies for the night. It’s an erotic time, it fills you with all of these feelings that are normally manageable during the day.”

Fluttershy was still incapable of speech, she was captivated by the princess’ monologue.

“You know exactly how that feels, don’t you?” Luna inquired, rhetorically. “Yes, I would definitely argue that as consumed as you were with your little Dashie, my night was to blame. Or would that be to thank?”

“Hha?” Fluttershy squeaked, as her most private, intimate secret was ripped from inside her and publicized.

“Don’t worry. Conversely to my sister’s attempts to convince you otherwise, you are no naughtier than any other pony. My sister may have stolen your innocence, but she hath not made you a pervert,” the Princess replied, “That, I should say, will be my job.”

Another similar squeak escaped Fluttershy’s mouth, although this one was much quieter, and was followed by a slight shiver of her hindquarters.

“Yes, I would conjecture that you could become a great and powerful pony of the night. But you will need a much more capable teacher than my diurnal sibling. Her whole reason to teach you was because she thought you were cute. Of which you should be insurmountably proud,” Luna paused, “But nonetheless, you should seek more …educated… counsel.”

Luna, lounged on Fluttershy’s bed, drank in the scent of the many nights of self-pleasure that her new protégé had enjoyed while the timid pony herself just quivered at the implications of what had been said. Luna slowly got up and walked over to the shaking pony and brushed a solitary hoof along her mane to calm her. Luna moved closer to Fluttershy’s ear and whispered softly “Tonight, you are mine, and if you are faithful to me, I will reward you greatly. So what do you say, will you be my student?”

“W-What about Celestia?”

“Oh, you needn’t leave her love unrequited. It has been a long time since a pony could handle her, and after my training, you will be most equipped to handle her sometimes strange desires.”

“T-Then… I guess it’s okay.”

“Oh, no. You need to be more confident than that. I’m not going to go through the effort unless you can convince me that you really want it.”

“I… I…” Fluttershy stuttered, she didn’t know how to be confident, but through the haze that her mind had descended into she began to get an idea. The princess wouldn’t see it coming at all. She knelt on her front legs so that her flank was sticking up in the air, flagged her tail to the side, and put on the most needy tone she could manage, “Mistress Luna… Take me!”

“Oh ponyfeathers!” Luna cursed under her breath. As a mistress of the night, that was an offer she was powerless to refuse. She felt a familiar tingle well up inside her as she tried to fight the compulsion to oblige Fluttershy. She shuddered as the tingle became overwhelming and centered in her hindquarters. She held back her magic as it attempted to escape its cranial imprisonment; the situation, like gravity, pulled her towards the yellow seductress, who was still shaking her rear at the princess.

Fluttershy, caught in the moment (and possibly affected by the awestruck alicorn’s lack of action) decided to take it upon herself. She backed towards Luna until she was a mere inch or two away. She wiggled her flank in the princess’ face, realizing how compromising it was. Her body chose then to perform its instinctual attractant – she felt her lower anatomy tense up and a copious amount of her pheromone-laced love juice dribbled out. Luna, this time, took the hint.

The princess threw all royal mannerisms to the wind and lapped at Fluttershy’s entrance as her conscience lapsed. Magic flooded forth and bound Fluttershy to her, holding her in a tender blue aura that was simultaneously there and not. Fluttershy summoned all of the stamina and courage she possessed and pressed back on the princess.

Luna’s head was now covered in Fluttershy’s juices and her magic was growing more and more out of control. The blue sparkles turned inward on her and threatened the applicability of the former pronoun. She found herself with a (albeit temporary) set of male parts that were sure to please any mare. Luna loved her magic but sometimes it was her undoing.

As Luna reared up, Fluttershy suddenly realized what was happening. “Wait.” She said softly, feeling the unnaturally hard member pressed against her. The princess missed her warning and attempted to press forward. Fluttershy yelled “WAIT!”

Luna froze. Fluttershy shrugged the princess off of her and turned around. “I-I’m sorry… I just don’t want that y-yet. Um… I w-want to p-play with it before you put it away, though.”

Luna hadn’t even thought. Probably the largest object Fluttershy had ever taken was a carrot or two. Very small compared to the larger-than-life member that swung awkwardly between her quivering legs. “Oh, I hadn’t considered your reservations. Please do forgive me.”

“No problem.” Fluttershy said softly, wearing a cute smile as she lowered her head between the princess’ legs to lick at her navy and black speckled stallion-parts. Luna shuddered with the first lick. She had tried this before with mixed results, but Fluttershy was the first to be so… proactive. Even Fluttershy herself knew not where this courage came from, but she liked it. She felt powerful, the epitome of these kinds of acts was speechless and bucking her hips at the meek yellow Pegasus. That was power.

“Ah, that feels wonderful, my little pony.” Luna moaned, starting to realize that her resolve was considerably less in this state.

Fluttershy, who had started suckling on the princess’ unnatural member pulled off with a loud slurp and a trail of wetness. “Ah, but princess… I believe right now you are in fact my little pony.” Fluttershy pulled away enough to make eye contact and wink before going back to business. She wanted badly to finish off the princess and prove her superiority. Now that she thought of it, she had no idea where any of this dominance came from. Maybe Dashie was rubbing off on her… Oh wait, that happened last night. Now the princess was rubbing off on her too.

Luna was getting close, which for her was still a ways off. The princess had taught herself great stamina at this stage such that she could remain in unspeakable bliss for the longest possible time. Oh wait, she definitely wasn’t going to make it much farther. Fluttershy was taking a good 14 inches at the time, and the princess’ hard member was prodding at her throat. Fluttershy could feel the head of Luna’s stallionhood beginning to flare and she pulled it out slightly so she could play with the tip using her tongue.

“Oh, For the love of Equestria!” Luna yelled as she felt her release imminent. A moment later, her white, sticky stallion cum welled up in her stallionhood and flooded out in gigantic half-cup squirts. One shot down Fluttershy’s throat, another painted her face, and yet another covered her hair and forelegs. The princess shuddered and backed away slowly, her softening member dripping a string of her juices and swinging between her legs, stained like Fluttershy’s with the fruits of the pegasus’ labors.

Fluttershy wiped some of the sticky goo off of her face, and tasted it, since the seed shot down her throat was of such force that she had not had a chance to savor it. It was not impressive in taste, but the sheer quantity of it made Fluttershy shudder in pleasure. She had made a princess cum in her mouth, and she could probably do it again.

“Want more princess?” Fluttershy inquired. She wiggled a little, seductively, and the princess appreciated the gesture. Her libido had been entirely removed by the orgasm she had just experienced. This was why she disliked playing the stallion. It was always one and done.

“In any other circumstance I would. But it seems you finished me off very well. So I’ll make this wager with you.” Luna began. “You were quite assertive tonight, which I know is not in your character. It was my moon that made you so brazen; it was also why you tried to dominate your friend last night and why you had the ‘creative’ idea of impaling yourself on my sister’s horn.” Luna had regained her seductive voice by now, and was spinning a deal that ‘shy wouldn’t be able to resist. “I’ll come back in one week. Seven days from now. I will not go lightly on you, and I would advise you don’t go easy on my either. Here’s the wager: If you make me come first, I will be your faithful little slave whenever you want. I will please you however you want whenever you want, as long as my royal duties don’t occupy me, which they never seem to. I would call you whatever you want; Mistress Fluttershy, maybe even Princess Fluttershy…” Luna began, “But if I make you come first, I will make you my eternal slave; you will bend to my will and call me Mistress. I would let you live with your Ponyville friends still, but I would need you to visit Canterlot very frequently.”

“I-I’m not sure… T-this whole thing was really fast. I-I just want to um… be more sensual.”

“Oh, come on, be a good sport. At least give me a chance. I’m a very kind mistress, if you must know… I will rather like to hear your screams of adoration as I please you.”

“This really sounds like a bad idea… But I can’t exactly say no to a princess…” Fluttershy said… “So I suppose so… Um… If that is okay.”

“Yes, my little pony. I do hope you put up a good fight,” Luna said, “Because in one week, I will make you mine.” Luna said, perching on Fluttershy’s windowsill before alighting into the night sky.

“I will make you mine yet, my little pet” Luna said to the empty night sky as if Fluttershy were listening.

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