Equestrian Heroes
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Naruto x ?
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Story Start
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Naruto was beginning to wonder if there was any truth to the rumors of Celestia having an all-seeing orb that she used to spy on her subjects? It was the only logical explanation for how she could know so much or could pop up at anyplace at a mere whim. That or she had a ton of spies.

Well okay, maybe the more logical explanation was Luna got nervous about their impending date and turned to her big sister for advice, but he liked his explanation better, which reminded him he really needed to get back at Celestia with a prank of his own. Her reign of trolling was going on for far too long.

As he was led into Celestia’s private study and freed from his confines he walked in. There she was, sitting behind her desk scribbling something or another on some sort of document. Her hair flowing with its usual ethereal glow and as always she was dressed in her royal negligee. He was about ready to let her have a piece of his mind when she looked up and with that warm motherly smile of hers spoke two simple words, “Thank you.”

Evil. Celestia truly was one of the greatest evils he had ever faced. Obito, Madara, and Black Zetsu combined did not have an ounce of her cunning or her ability to simply confuse the shit out of him. “What?”

“When Luna approached me about your proposal she was happy. Well extremely nervous more than anything, but happy. “ Celestia explained then proceeded to place down her quill and stood up.

It was moments like this Naruto kept forgetting just how tall the regal mare was. “Well Luna is my friend; I’d help anypony who is a friend.”

Celestia gazed down at the blond. “And a friend is what Luna considers you, but have you ever thought about maybe being more than that?”

Naruto raised an eyebrow at that. “Wait a minute…are you asking me what I think you’re asking me?”

With a nod Celestia began speaking. “I want to know if you have any intent on courting Luna?” From having formed a friendship with the blond Celestia knew that when it came to romance Naruto was rather daft. More than once one of the maids or daughter of a noble had flirted with the blond and he seemed to miss the cues completely.

“W-What?” He stammered, almost falling over as he tried to process what he had just been questioned. “I don’t have any plans to court Luna. She’s a rather nice mare, but this seems so sudden. Also wouldn’t it cause some sort of political turmoil?” Naruto quickly recovered and simply fell into the role of the Seventh. He was no stranger to the politics thanks to his tenure as Hokage and one of the more messier aspects was the whole aspect of romance and courting that played deeply into politics. Lords know he heard about it quite a bit from advisers during his time of Hokage when it came to his children dating or at least being rumored dating common people.

“Come now Naruto, you know I have no interest in following protocols to the tee. Quite simply I wish what’s best for my sister and making sure she has a successful first date is one of the ways I want to make sure everything is perfect.”

“But its not a date. Its just a gathering with two friends, alone, possibly enjoying confectioneries.” He explained as a coy smile formed on Celestia’s lips.

“Oh no, I insist. I’ve already sent for the tailor to begin working on a dress for Luna. I just wanted to make sure that you will be showing my sister a good time is all.” She explained as Naruto realized what was happening.

“In other words…” He trailed off as Celestia finished the line of thought he was going on.

“I wish for you to take Luna on a proper date.” She finished his statement then continued her line of thought. “By no means am I trying to coerce you into forming a relationship with Luna. At the moment she is still rather emotionally vulnerable and pushing forward into something like a relationship is the not the thing she needs right now, but if such a thing were unavoidable I would like her first experience with such a thing be positive. I am fully well aware that after the nation is addressed about my sister’s return there will be those who will treat her with hostility open and other wise. There will even be those who see her as a tool to get to me or hurt me and if they do not fall into that category they will see her easy to manipulate to get laws passed that I have rebuked or to increase their status, something I know you are vehemently opposed to.” With that she opened the door. “Walk with me will you.” She requested with him as she began heading to the dining area.

Naruto trailed behind as new questions were beginning to pop into his head. “You seem rather prepared and accepting of this."

"When Luna told me about this I do admit I was rather surprised. Regardless I wish for nothing more, but to see to it that she is happy." She explained as they continued down the long hallway. As they continued their journey there were all assortments of maids and servants hustling and bustling throughout the castle. There were delegates transporting letters and delivery ponies bringing in anything from books to crates of food.

“Your Majesty!” “Your Highness!” “Greetings Princess!” They would all greet with a bow as their eyes held as Celestia walked by. With a smile and a greeting of ‘My Little Ponies’ she never broke her stride as she kept her graceful pace.

“It all started from the moment I laid eyes on Twilight’s Cutie mark I knew she was the one. From that moment I spent the next fifteen years of whatever free time I had in preparation for Luna’s return. What would have taken years of bureaucratic maneuvering dealing with the fallout of Luna’s return and the damages I have been able to plan ahead and have all the laws and solutions ready in these few short months. By the start of December the legal side of everything should be finished. Even the formation of Luna’s very own squad should be dealt with soon, even if politically the move will be seen as unfavorable.”

“Because of Luna?” He asked as a look of sadness took reign of the Princess's gentle face.

“Because of Nightmare Moon.” She answered. “If you recall a race of ponies, the Theastrals, commonly known as Negasi are fiercely loyal to Luna regardless of her state currently including during her possession not too long ago. The Theastrals were once ponies from the three tribes which mostly consisted of Pegasi. Dark magic was used to transform them into their current day image. Discrimination against them was rampant during the banishment and it lasted for centuries. Despite my attempts to help them, they rebuked any olive branch I extended out to them. They were brainwashed into near fanatical loyalty by the magic that transformed them. As time passed the tale of Nightmare Moon had become a fairy tale and the discrimination lessen until the Summer Sun Celebration reawakening the magic within them. Now that Luna has been returned to her true self the spell has gone dormant, but their loyalty to my sister has not. She is their goddess in name, blood, and magic. Unfortunately the Cloudsdale incident has reawakened the discrimination against them.”

“Cloudsdale incident?” Now that he thought about it, he knew nothing about the incident in the other cities besides criminals busting out the increase of bandit activity in the country side.

“Cloudsdale if you remember is a Pegasi city so most of the Theastrals were sent to take it over. I had Cadance stationed at the city during the time of the Festival. She and Captain Armor were there to repel the attack.”

It was beginning to make sense now. Why Celestia had her personal captain in Ponyville and where the rest of them were during this event. Celestia had divided her forces in preparation for such an event and considering reading the mind of every pony citizen was probably a feat even beyond Celestia there was no telling who could have been a Nightmare agent so trying to warn anypony could alert them.

“And let me guess, the list you have of things you prepared for just goes on doesn’t it?” Naruto asked as they finally entered the dining room.

A smile formed on the Sun Goddess’s face. “I have been at this for over two Millennium. If I didn’t have a contingency plan or two for such things I would be a rather disappointing Matriarch and leader would I not?“ With that they took a seat the table. “Now would you rather have me give you the protective sister speech now or before the date?” Naruto promptly groaned and face desk. “I’ll take that as a yes for now. “

---

The promise day had long last arrived. Luna was a bit nervous. When she was informed that this was going to be a formal date instead of outing like initially conceived Luna was quite confused. She sat aptly as Celestia informed her that while mares courting stallions were still rather common place stallions courting a mare was now something that could happen. Luna now found herself having to be the courtee instead of the one doing the courting.

“Sister you must hold still. Your fidgeting makes it difficult for the maids to finish their work.” Celestia said as Luna shot her a look.

After all it was Celestia who insisted that she lend her aid to her sister. As such several maids were working on making sure Luna was looking perfect. They worked on her mane, polishing her hooves, tending to her nails as well as her coat. “Tis is not the most comfortable situation sister.”

“Nevertheless it is only my wish you enjoy yourself this evening. It would do you good to get out of the castle and see more of Canterlot. Naruto will prove to be a fine companion.”

“Yes, he is indeed easy on the eyes,” Luna then sent her sister a coy look. “We are surprise that thou hasn’t snatched himself up for thyself sister.”

A giggle escaped Celestia’s lips as she recalled fleeting thoughts from her youth. Those were the days, so carefree and joy yet reckless. “Yes, I suppose back in the old days that would sound like something I would do, but no, Naruto is a friend.” Which was what she needed. No politics. No money. No worship or being in awe of her. Just a friend. A stallion who was a friend. One who did not notice she was a mare besides the first time they had met. Celestia had to suppress a sigh. When was the last time she had a genuine friend prior to Naruto? Three, maybe four decades? While Celestia had positive memories of ponies she had considered friends, losing Luna had hurt her so deeply that Celestia took care not to grow that close to those who were mortal to avoid that sense of loss and other immortals merely looked at the alliances for their political and economic values instead of the possibility of developing friendships.

There were moments in time where Celestia did take up a lover for particular annoying heat seasons or when being in her bed felt lonely, but those never lasted long. It was times like this she cursed being an Alicorn, if it wasn’t for the stamina then it was her status and stature that made her unapproachable to many. The sound of Luna calling her brought her out of her memories. “Sorry Luna, I supposed I started thinking about the last time I went on a date myself. It has been a while I have to admit.”

“Well since you were so intent on seeing us have a good time we shall enjoy the companionship with our friend tonight.” Luna then grinned saucily. “Who knows we might even bring him back to our personal bed chambers to give him the proper thank you he deserves.” Of the two sisters Luna was the saucier of the two.

The maids in question began to blush deeply at what the Lunar Princess was insinuating. The maids had expected Celestia to begin scolding her sister for such improper talk of one of her status and station was surprised by the fact Celestia giggled.

“Oh sister, I’m not sure he’s quite ready for something like that, but if any mare could get through to him then it would be you and your direct methods.” It was moments like this Celestia missed dearly. Luna’s salacious humor while at one time was something Celestia would have scolded her for using in company was merely welcomed. “Just handle things a bit delicately sister as you must be restrained with your usual advances. Remember the courting culture has changed from how it was a thousand years ago.”

“Of course sister.” Celestia after all had only spent the last three days drilling it into her head.

Finally after what felt like forever Luna was dressed in ready. She stood in front of the mirror and looked herself over.

At first she was a bit nervous and opposed to showing so much skin, but Celestia assured her the styles were a bit more lax than they used to be. Luna remembered when showing one’s shoulders were considered risqué.At the very least she was finally coming into her form. She had a delightful amount of weight now embracing her hips, giving her much larger, firmer flanks and a pair of shapely half-moon that equaled if not surpassed her sister's. Her chest was fuller as well as not to mention her over all form, especially her legs and wings gaining muscle tone from the exercising she had managed to fit in during her recovery.

“You look wonderful Luna.” Celestia complimented as she placed her hands on Luna’s shoulders.

“Thank you Celie.” Luna responded, suddenly filling the flittering of butterflies in her stomach. She hadn’t felt this way since she was a filly.

---

Naruto was waiting by one of the castle’s secret entrances. It was normally off limits to anyone not part of the castle staff. This part of the castle of course was connected to a path that led to Canterlot. A convenience for when Celestia wanted to leave the castle and not be mobbed by other equines. He made his way in his latest suit. A navy hue and a four-button vest three-piece suit. The shirt was a light pale-gray dress shirt with black tuxedo dress shoes and Flat-front slacks.

A servant then walked out, dressed in a fancy Etalian suit. “Presenting her majesty Princess Luna!” He announced as he caught sight of something walking down the stairs.

That was when he saw her, the room, normally dark was a lit by the glow of the moon thanks to a little sent nudge. There in his sight stepped her majesty Princess Luna, wearing a dark black-blue dress reminiscent of the night sky with white sparkles reminiscent of the stars itself. The skirt swirled around her legs and clung to her figure. On her head she wore a small crown, less formal then her usual royal armaments. Her on her feet were also heels with the same shade of coloring her mane.

“We admit, at first we were uncertain about our look, but the bustle of the old times could be unbearable at times, along with flounced skirts. The added movement is also a plus, we hope that thee finds this outfit pleasing to thine eye.” She spoke as a hint of shyness pass acrossed her face.

“You look absolutely lovely fair princess. Even the stars pale at your beauty.” He spoke out to her in near breathless tones.

“Thine appearance is also rather ravishing." She admitted as she gave him an appreciating look over. "Are those for us?” she asked, indicating the Bouquet.

“Indeed,” He said, undoing the wrapping at the top and presenting them to Luna.

“Night Cactuses,” She whispered their name. “Where did thee find these?” She added as her expression gave away that she was quite surprised.

“In the Everfree forest." He answered her and then began to explain how he came across the plant." I stumbled upon them while gathering resources with Fluttershy and she told me they meant, Queen of the Night. So I thought you would like them.”

“It pleases us greatly.” She responded with great enthusiasm as she called over a servant and with a order to place them in a vase in her room the two of them were ready to leave.

Celestia then made her presence known. “Have fun you two, try to stay together and…” She lingered her gaze on Naruto. “…Naruto I sure that I don’t have to tell you if you hurt Luna I will lock you in a dungeon and then banish you.” She finished with a stern look at the stallion who was trying to figure out if she was playful serious or serious serious. It wouldn't be the first time Celestia had him thrown in the dungeon after all.

“Sister, I am a grown mare. I can take care of myself.” She argued with an annoyed huff as she resisted the urge to respond in a matter that suggested otherwise.

“Trust me Luna, she teases me with that comment like once a month whenever I pull one over her." He explained to Luna before he turns his attention back to Celestia. "Don’t think you’re off the hook yet Princess Celestia. I’m going to get you back for your latest string of jokes.” He promised as Celestia nodded while on the inside sporting the biggest grin imaginable.

“I will be waiting for when you wish to make such a move.” Which was fancy for ‘bring it’. As an afterthought she added. “Do try to be home by when the sun is to be raised.”

“We shall try sister,” Luna said, as she turned to Naruto a with a salacious grin. “Tis all depends on Naruto and his plans.”

Naruto couldn’t help it as a faint blush formed on his cheeks. If Luna and Celestia ever decided to tag team him it would be all over. Such a team would be invincible, as no stallion could handle all that cunning, charisma, beauty, and salaciously enough booty.

---

They made their way to the city of Canterlot and Luna was surprised by what she saw. So many happy ponies were up and about. Shopping, conversing, and eating. While Luna had heard rumors of a more active night light she wanted to witness such things for herself before she made a decision.

The brief moment of happiness she felt came tumbling down when she realized said ponies paid little attention of mention to the arrangement of stars she made earlier this evening and all the bright lightning from the streets made it difficult to see her creations.

Soon many ponies were pointing and conversing. Suddenly flashes of light went off. Ponies began crowding around them firing question after question.

“Princess Luna why have you decided to come down to the city?”

“Who is that stallion with you?”

“How come you have never come out to address the citizens before?”

“Is this a date?”

Luna tried to answer when she was bombarded by pony after pony. She found herself unable to answer as she was trying to keep up.

The tone of the questions slowly began to change.

“How did you convince Celestia to let you out of the castle?”

“So when is the next time that you and your kind are going to try and take over the city?” The stallion in question found himself promptly dropped, his camera broken.

Naruto drew back his hand as the crowd glanced down from the stallion and looked up at the blond in shock. “Her majesty isn’t answering any questions!” He said as he grabbed Luna’s hand and began leading her away. Sure enough several guards showed up and began making the hecklers and crowd back off. The temporary night guard were assigned to keep their distance and to only step in to keep order.

Accusations were being hurled. ‘Nightmare Moon’ ‘Negasi Lover’ ‘Hellspawn’ It caused a painful knot to form in the pit of Naruto’s stomach. For a moment he had considered this was a good idea but dismissed it.

“Forget those idiots Luna.” He said as he turned back to face Luna who seemed stuck in the middle of indecision. “There are those of us who care about and know the real you. Princess Celestia. The Elements. Me.”

His words brought Luna out of the funk she was threatening to slip into. “Indeed, we shall not let some loud mouth hecklers to deter us from this evening. After all we do not wish for all this preparation to be for naught.” They arrived to the restaurant only to walk passed it. “We have passed the restaurant.”

“I know,” he replied as suddenly the two of them disappeared in a swirl of wind. Teleporting to a new location the two of them had arrived in a crystal cavern of sorts. Luna gazed around in awe at the brightly lit cavern as there was a blanket with many comfortable pillows and a basket were placed upon a chiseled platform near a glittering lake attached to a shimmery waterfall.

Every so often wind would blow, striking some of the holes in the cavern causing an echo of a note. The location had to be centuries if not millenniums old as much of the rock and cavern contained old ores and minerals that would have long been mined. “I hope you can forgive my deception. I think a first date without big sister’s eyes and ears would be more enjoyable.” A chuckle escaped Naruto’s lips along with a soft grunt. “There’s going to be Tartarus to pay. She’s probably going to accuse me of planning this to sneak away with you.”

An idea promptly formed in Luna’s mind. “Oh?” She asked as she began to walk over towards the block. Careful steps with a sexy sway of her hips. “Was that not your intent? To get us alone with thee.” She placed her hands on his chest. “We have no objection sir Naruto.” She finished with her best sultry tone immediately flustering the blond. Soon a rich and heartfelt laugh erupted from Luna’s lips. “Sister was correct, thee is vulnerable to our kind of humor. Thine reaction as better than we expected.”

“Uugh, I should have known,” He finished with a pout. “One Celestia is enough.” He grumbled to himself a bit louder than he attended.

Luna soon began to calm herself down after Naruto's unfavorable mention of her sister. “Does sister ruffle your fur that much?” She decided to ask him, curious about the relationship between the two.

“Yes, very much I guess ,because I just see Celestia for well…Celestia instead of her crown. I don’t see the crown, wings, and horn, just a white mare that enjoys pulling pranks on me every chance she gets. She's also one of my oldest and dearest friends in this nation. I respect her, the wisdom she holds and the tough choices she has to make, but that doesn't mean I'll take her lightly during our battle of the greatest trickster. ”

“We assume thee return the favor often?” she asked as Naruto nodded. Remembering the meal he hopped over to the platform and extended his hand, helping the princess up.

“Not as often as I would have liked lately though. I hope you don’t mind, but I made us a meal. Not the most lavish of meals, but any rube can go to a restaurant or make a spectacle in terms of finding a needlessly complicated meal, but I wanted to make us a simple spread. There’s a bowl of salad, some sandwiches, potato salad, some strawberries and an apple Pie for desert. For our drinks I brought a cooler filled with a selection of sodas or, he stamped his foot on the ground causing a bucket full of ice with wine in it to rise. “…or some Wine if that is more your taste.”

“We are indeed impressed. What went from a simple outing between friends is more reminiscent of how a mare would use her cooking in an attempt to woo a stallion. If this is how you wish for the nature of our relationship to go, I have no problems with that.” Luna began teasing him again only for her to be surprised when Naruto merely grinned.

“So you wish to be my sugarmare? I have no problems with that.” He said as grabbed the cooler. “Wine or Soda?” He offered as Luna looked between the two and thought about it.

“If you have any confectionery in the grape flavor I will enjoy some. I wish to save the wine for desert.” She finished with a wink and sure enough Naruto laughed it off. “We must say, it appears thee is loosening up.”

“Yeah well, we can’t enjoy ourselves if I’m flustered by every moment you make now can I? Besides, its all part of my grand master plan. If mares don’t think I was easily flusterable they won’t stop their little jokes and displays of playful affection which of course ends up as a win-win for me.” For the most part he was just joking.

“Aah quite the devious one.” With that Naruto led Luna to the arrangement of pillows he had made for her to sit on and opened the basket. The food was then spread out among the blanket. “So Naruto, from whence comest thee, Ponyville or maybe thine place of origin is another town?”

“I come from the outlands. My curiosity about the world and magic itself brought me to Canterlot which led to me meeting your sister.” Naruto paused, realizing he skipped a chunk of what happened between his arrival to this world and heading to Canterlot. “Actually, let me correct that. I happened upon Ponyville first, tired and injured and being attacked by dark creatures when I was saved by Rainbow Dash. I spent a good deal of time in Ponyville and then I came to Canterlot.”

“And of your profession?”

“I haven’t established a career yet. I am actually in the midst of opening my own dojo to teach the local populous how to defend themselves. Most of them are civilians, but considering we live near Everfree Forest it couldn’t hurt for the ponies of the town to learn how to defend themselves. For a time I did work on Sweet Apple Acres before becoming an assistant to Rarity for some time. I even help Fluttershy gather herbs and plants by making trips into the Everfree Forest.”

“My, it appears thee has quite the relationship with the bearers. We are surprised thee hasn’t been besought requests to form a herd.”

Naruto chuckled. “I have had a mare or two approached me, but I wasn’t interested at that time. I have decided to put myself on the market recently though. There is a list of mares I am willing to date, but I need to have one date with them before I consider anything more.”

Luna nodded, “Old-fashioned, respectable.”

“I glad you think so.” He remember one mare got rather angry and accused him of being a colt cuddler. Just because someone didn’t want to date you, didn’t mean you had to be belligerent and started insulting them as if that was going to get him to change his mind about wanting to go on the date.

“Would Generosity not be disappointed that thee will be lacking a report on the dinery?”

“I think she’ll be okay,” he responded as he closed his eyes and softly exhale. He open then and set his gaze down on Luna. “I’m sorry, I should have known there would have been ponies who were going to act like…” Naruto paused, almost using the term asses before remembering donkeys were citizens in this world. “…out right bastards.” When he finished he noticed Luna give him a confused look consisting of a raised eyebrow and an expression that read ‘explain’ on her face. “The term has a second connotation on it for modern day insults. Its more commonly used as a modern day curse against colts or stallions who are mean or you have contempt for.” He explained.

“Oh,” Luna mouthed out, understanding what he meant now. “Tis not your fault. We rather be hither than there. The populous would tarry and gawk at us like some spectacle and would detract from the atmosphere. Shall we forget about them and continue enjoying the rest of the evening.”

“Indeed.” He said as they began to dig into the meal. As enjoyable as the date was it had to sadly come to an end. It was going around four in the morning by the time the two of them were making their way back. Singing a sea shanty Luna had thought him as they made their way down the path way.

“Thy must give Honesty our compliments. While simple the Applepie was an enjoyable treat.”

“I’m sure hearing that will make her week.” Naruto replied as the two of them came to a stop at the doorway. Their gazes lingered for a moment.

“We…really enjoyed ourselves. Thank thee. We simply wished it could have lasted a little longer.” She brushed a strand of her hair out of the face. When they had regale moments of battle from their past the hair style Luna had come undone during the demonstration. Now it flowed and hung loose instead of the fancy do the maids took an hour to put together.

Naruto felt something when he noticed the expression on Luna’s face. Disappointment. Sad that their time together came to an end. He didn’t…he didn’t want it to end. “It…it doesn’t have to be a onetime thing.” He suddenly found himself say as Luna looked up at him in surprise. Hell, he was surprised himself. Where did that come from.

“It does not, does it?” Luna wondered. She wasn’t sure how she felt about the stallion yet, but she knew it was positive. It was just…she wasn’t ready for courting. There were still some things to sort out, but maybe when she knew how she felt a little more. “We do hope to spend more time with thee. We bid you goodnight.” Luna said as she leaned over and placed a tender kiss on Naruto’s right cheek.

“Night Luna.” He answered his voice in a dazed whisper. He watched her trailed up those stairs and found himself adding one more name to his list.

Princess Luna.

When Luna returned to her room she not surprised to find Celestia sitting in a chair in the corner of the room. If she had been anypony else she would have been frightened, but she was used to her sister’s antics. “Hello Tia? Shouldn’t thou be resting?” She asked as a grin formed on Celestia’s face.

“Sleep is for the weak and dead sister.” The Sun Goddess replied, doing a passable imitation of Luna’s voice, quoting a comment Luna had once made when in their younger sisters the eager sister had insisted on bugging Celestia whenever she tried to go to sleep.

Luna took notice of an empty cup of tea and an empty plate on the table. “Speaking of memories Sister, seeing as you have kept up your snacking habit we are surprised that over the Millennia thou’s hindquarters have not grown to match the size of our charge.” As she finished this she was hit in the snout by one of her pillow’s courtesy of Celestia.

Another thing Luna would always tease her sister about. The size of Celestia’s rear, which to be fair was rather quite large, but in a size sort of way if you asked just about anyone with a working sex drive and good tastes. It was only shortly before Luna’s banishment that large and jiggly behinds started to grow popularity or smaller and leaner ones.

“I have you know our subjects find this short of trait desirable now.” Celestia countered, but unable to keep the huffiness out of her voice. “Speaking of which, you know the drill sister.”

“Indeed.” Luna kicked off her shoes and sat on the bed. Celestia eagerly joined her, as Luna began going over the details of the outing.

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