The Endeavor of the Damned Shadows

by dannny43


Chapter 9: A Little Night Ride.

Twilight had finally settled across the sky as I backtracked across Ponyville, towards Nightmare Moon's statue. Playing this world's version of Dungeons and Dragons had left me completely sidetracked.

Even though the three of us agreed to do a refresher course only, well, things may have... gotten a little out of hand. I mean, when you tragically roll a nat. 1 in trying to pet a dog, can you really blame a guy for devoting the next three hours to establishing a five-star doggy resort out of guilt?

Anyways, before any of us knew it, three hours passed by, and I was left to make a mad scramble back to my chariot if I was to make it on time.

Ponyville, even at this hour, was still a hubbub of activity. Pinkie's place was full of late-night diners, Town Square was seemingly hosting a late-night disco party, and even Trixie had decided to pay a late-night visit, performing one of her shows to a boisterous crowd.

All of which I ignored.

Crossing back over the cobblestone bridge, I rush towards our rendezvous point, but the moment the statue came into full view, my speed comes to a grinding halt.

Her gaze lingering on the monument, Luna stood calm and rigid with the only motion coming from her flowing hair. As I press on, it doesn't take long before she takes note of present company. "You know, I almost reduced this statue to pebbles once. Back when I visited on my first Nightmare Night. The timely visit from Twilight the Bearded prevented me from doing so. But, as you may already know, with a little help, I resolved past my short-sighted issues, and I am now the much anticipated and dreaded 'Living Nightmare of the Night'. Adored by all and welcomed with terrorized glee. The candies are a nice bonus too."

"Heh, oh yeah, I recall. Especially the giant annoying chicken. But, um, yeah, uh, what are you doing here?" I take a few quick scans of the surrounding area before following up with, "And where's the chariot and its crew?"

"Retired for the night under my order," Luna said, taking one last look at Nightmare Moon before taking several steps closer to me. A look of slight angst adorning a small corner of her mask. "Tonight is the most beautiful and calm it has been in weeks. I figured you and I could spend some time together before you go under. Does... that sound good to you?"

"Uh, well uh, sure. Yeah, that sounds fine, but the operation is in the next two hours. Teleportation isn't good for my health, the train is too slow to be viable, and with the chariot gone, how exactly are we gonna make it to Canterlot in time?"

A smirk adorned Luna's face as her wings unfurled to their maximum span, revealing glistening ebony feathers that mixed along with her flowing hair, displayed an expansive sea of constellations and nebulas, all of which painted Luna in an unparalleled, majestic, and elegant pose. "What do you say, Austin? Care to join me for a night ride?"


The cool night breeze that coursed through my hair, the brilliant moonlight that shone across Equestria, and the exhilaration of adrenalin provided a decent distraction from the fact that I was straddling on Luna's back in the world's most awkward pony ride ever. Of all time.

Thankfully, the close intimate contact of our connected bodies was off-put by the anxiety-inducing swirls and impromptu evasive maneuvers of one very contrite Princess who struggled through a torrent of heavy wind and the added pressure of one special passenger. She screamed her regret not a moment sooner as she desperately fought to keep us both from being cratered. "Perhaps I should have saved the chariot after all! Ugh! By the moon, I forgot how heavy you are!"

A sudden buck of wind forced me to tighten my already crushing grip further. "As...alluring as your offer has been so far, I must agree about the chariot! Also, did you just call me fat, Princess!?" I roared back over the wind.

"What!? Heavens no! I-I-I merely meant to imply that I'm sorely lacking in the uh, strength of earth pony magic! I meant no offense!"

"It's ok, Luna! I was just joking! I pride myself for having a thick skin, a seemingly rare thing among my kind these days! Besides, it's not really offensive to me if it's true!"

A thin chortle could be barely heard escaping from Luna, "Beg pardon, Austin, but you are as protruding as my sister's gourmandized glutes shouldn't be! Not for a lack of trying on her part, what with the amount of confectioneries she consumes on a daily basis! Even the Pink One would be flustered by all of Celestia's cake!"

I maneuver my head to be by Luna's ear, ceasing my need to shout for every word. "Yeah, one of the perks of being an alicorn I assume. Little need to worry about your weight and other junk. But, hey, this cake thing isn't just a princess problem solely. I mean, have you seen what your little ponies call their daily meals? America is often considered the leading nation in obesity, but if we were to compare you ponies to us Americans, and you guys didn't have your magic metabolism or whatever, well, y'all would definitely take the cake. Pun specifically intended."

My cheeks couldn't help but tinge a little and my chest was aflutter with the butterflies when her quite lovely giggling reached my ears. I find myself honestly a little shocked, what with us barely 'flying' in control, that I still have enough blood flowing in my head to be able to glow some.

It would seem my punniness was a tad too strong for Luna because as she was distracted giggling away, she failed to notice the cloud within our trajectory. The moment she made impact, I unceremoniously and quite easily found myself ejected from Luna's back, without any changes to my gripping posture.

With everything that I have experienced within this world proving to be far too real for my liking, it does come as quite a surprise when cartoony elements present themselves to me. For example, Rainbow Dash and her Stuka siren dive, Derpy and her Flintstone 'bonk' sound effect, and now, my gravity-defying ejection straight from Wile E. Coyote. I even did the whole 'look down at certain doom and then at the viewer' thing before I found myself plummeting straight down, bringing back some recent bad memories. Luna too, seemed to recall these memories because quick as a flash, I found myself cradled in Luna's legs, preventing me from purchasing the farm once more.

The steep incline she took to recorrect our plummeting course, found us breaching the topmost cloud level. We were both bathed in the full shine of the moonlight.

Skidding to a sudden stop atop one nearby cloud, we once more find ourselves in an awkward bind, far worst than the last. Face to face, barrel to barrel... me... on top of... her.

...Or at least we would have if circumstances had... 'favored' us more. No, instead I find myself imitating one of those 'Hang in there!' cat posters. Hanging off Luna's side half-submerged in the cloud, I'm left clawing and struggling to keep myself afloat on her. "L-Little help h-here!" I masculinely squeaked out.

Instead of hauling themselves up into the air, Luna opted to allow herself to sink through the cloud, catching Austin on her back amid the free fall, safe and secured once more. "Well... that was... certainly something," commented Luna.

My crushing grip returned once more around her waist, increased ten-fold this time around. "Yeah, more like, Sum Ting Wong. Look, can we go for a low-altitude cruise? Because I feel like any moment now, we'll be committed to a kamikaze dive."

Getting the gist, Luna heeded my words as she began a gradual dip back beneath the clouds. Once we broke through, we both spotted what appeared to be a commercial blimp heading in the general direction of Canterlot which can be seen on the horizon. Luna circled the vessel a few times before committing herself to land on its roof. Successfully completing her landing without issue, Luna turned her gaze back to me, giving a reassuring look as I had yet to disembark. With her approval in tow, I allow my adrenalin to calm and my legs to relax. "Zero out of ten, would do again." Not a moment later, I ragdoll onto the rubbery tarp, having been drained of all energy from the night flight. I find myself laid out like a fish. "Uuuggghhh. This ain't no chariot, but it'll do."

Luna nodded in agreement as she too settled herself alongside me, huffing and puffing from the exertion that had finally caught up. "*Hugh*, *Hagh*, Indeed, plus it provides the ideal view of my domain." With that said, Luna magicked up a fluffy royal pillow of which she proceeded to impart her royal garments onto before rolling over onto her back like a dog, eyes on her starry skies.

There we spent the next few minutes in companionable silence, laying on the stable envelope with a cloud-free view of the cosmos. Seeing all those twinkling balls of fire up above, made me curious as to a certain aspect between the two ruling sisters. "So Luna, all these stars in the night sky are under your realm, right? And your sister's relates to that of the sun alone, correct?"

"Correct, on both accounts. Though my domain has been 'shared' with my sister for the last millennia, the stars and night sky obey my command alone. Our inherited duties have not changed since the day of ascension, with the exception of the fickle moon. A deliberate choice in design."

"Right, right. And over the many years of both of your reigns, I'm sure you both have been subject to many debates as to who is the more powerful sister, right?"

Luna's face visibly drooped and she released a remorseful sigh before focusing her sight onto me, "Not much of a debate nowadays, I'm afraid. A thousand years out of the loop, as they say, has left me nothing but a children's tall tale. The statue back in Ponyville is a testament to that." Luna shifted her gaze back above. "But yes, once upon a time, heated debates consumed our little ponies' time and our courtrooms."

"And?" I asked, knowing how it'll make Luna feel, but I needed to make sure of her answer.

"*Sigh*, I believe you may already know my tale. Our little ponies all lived by the day, and spurned my... and slept through my night. Her little ponies feared my cold darkness and worshipped her warm light. The debates ultimately boiled down into simple resolutions. Which Princess did they kneel before in awe and respect, and which did they grovel in fear? Who shepherded over their divine dawn and who dictated the dimming dusk? Who did they love... and who did they hate..."

"I... I'm sorry. I didn't mean to dredge up the past like that."

"It's alright, Austin. As they say these days, time heals all wounds. These past few years have given me enough time to reconcile with the past. Now I must make sure to never repeat myself in the future." Silence descended upon us once more.

...

...

...

"It was you, right?"

"Hmm?"

"The debates, the resolutions, you were predictably the favored victor for most of them, were you not?"

Luna couldn't help but raise a brow at me. "I thought my whole reminiscing of millennia past was clear enough, but no. No, I was not the favored result with any of the debates."

"Huh, well doesn't that beat all." I replied with a faux demeanor, "Here I was thinking the answer was plain as day, oh, excuse me, plain as night."

Luna rolled her eyes and held a small smirk before responding, "And why would that be, exactly?"

"Land sakes woman, you control the whole night sky! Don't you know exactly what that entails? Theoretically, you're like, a million times stronger than your sister."

"Oh?" Intrigue glistened within Luna's sparkling eyes along with a fair amount of disbelief. "Please, do tell."

"It's quite simple really,-" I began as I sprang up and proceeded to pace directly around Luna's prone form, where she continued to lay still, following my every move. "-first, your sun. You ponies do know that your sun, the one and only thing Celestia controls, is simply put, just a really up-close star, right? A star exactly or nearly the same as the hundreds of thousands that dot across the night sky, that you control. And within those thousands of stars that flood the sky, you got a wide variety with all kinds of qualities and power. I mean you got the red, white and brown dwarfs, main-sequence stars, subgiants, supergiants, red and yellow giants, protostars, neutron stars, stars going supernova! Luna, your entire night sky is an arsenal of black holes to be! The power of the sun is in the palm of Celestia's hoof, but that's just it, just the sun alone. The entire Galaxy practically heeds your beck and call. And you wonder why I chose you above her." I finish my essay by collapsing once more onto the tarp.

Luna's skeptical expression she held at the beginning of my rant had slowly melted away into a sincere smile by the time I wrapped it up. Instead of responding back, Luna reflected her sight back to the stars once more, an extra added twinkle within her eye. Doing the same myself, I'm treated to a brief but beautiful stream of shooting stars, streaking across the heavens.

"That's a nice theory you have," Luna commented, "But, truth be told, I know not the true extent of my powers. The secrets they hold elude me still after all these years, but it was sweet of you to view me in such a great position of power. The greatest feat of skill I can conduct currently is the birth of new stars, forged from the great bonds and memories of those I hold dear. Take that bright star right there, The North Star, as an example. I created it from my connection to Star Swirl the Bearded not long after his disappearance. I did so in the same hope that, as he had guided Celestia and me along the correct path of our destiny, so too can the North Star guide travelers and sailors safely to their destinations."

"Huh. Didn't know you could do that. That's honestly quite amazing and a little scary to me, for some reason. What about Celestia? Which star is hers?"

Sadness crossed her face once more, but only for the briefest of moments. "She had a special one long ago, it disappeared upon my transformation. Whether I destroyed it or lost connection to it due to my rage-fueled state, I'll never know."

"You have any other special stars up there?"

"Unfortunately, no. Not yet. Cadence and Twilight may have been adopted into our family, but the connection we share is not yet strong enough. Even if they were, I doubt Celestia would approve of the formation of any new stars, even though it is my choice to make. Besides, we have the murals within Canterlot Castle that are a fair substitute. They will suffice for now."

...

...

...

"...Hey, Luna, ...maybe... maybe one of these days, if I'm around long enough... maybe... I could earn my very own st-"

"Ahoy down there!" Called out a raspy voice, interrupting my little moment. Turning our attention towards the voice, we find a scruffy griffon wearing a sharp sailor's uniform descending from a nearby cloud before landing on the tarp before us.

"Well, I'll be. Skippa said he felt some strange turbulence, feared birds may have been caught in this here tarp, told me to check it out. Sure wasn't expecting to come on ye' royalty. Whach'as doing stowawaying on our roof eh? Skippa don't like no stowaways I tells ya, he gives ya two options usually, ya walk de plank!" The griffon 'suggested' with one nasty stink eye, "...Or you joins us for a top-quality on the house premiere dinna, just for the twos of ya, whaddaya say?"


The 'commercial' blimp we had decided to coop on top of, turned out to be a privately owned luxurious cruise ship, retained by a rich griffon entrepreneur, Beekolini, or something like that.

Despite the griffon sailor's humorous way of speech, he was entirely serious about the walking the plank thing, (a safe and 'humane', or should I say 'equine', procedure that doesn't involve any risk of harm or death I'm told). The crew as well do not take stowaways lightly. Thankfully, these griffons knew better than to commit political and commercial suicide when dealing with a Princess of Equestria.

So instead, we find ourselves seated at the bow of the ship, in an elegant and fancy environment fit for a five-star dining resort. "We have the time to spare for this, right Luna? I think we may be cutting it a little close."

"Relax, Lone Star. I know my time of night. We can still make it in time after we have dined. Now, let us see what is in store, as they say." Luna finished as she flipped the menu within her hooves, scanning for something worth her stomach.

Doing the same, I'm presented with a wide variety of strange entrées that completely fly over my head in familiarity. Almost nothing manages to catch my eye until I find the holy grail of all meals, an entrée that samples only two things on it. Lemons, and delicious juicy grilled salmon. Not an abomination of hay fried to a crisp with oil and sea salt, but real, actual meaty salmon, no veggies, no flowers, no horse shit, just meat.

I'm brought back to the living world by the soft taps of Luna's wing to my nose. "Lone Star, you're drooling all over the table cloth."

"Luna! Look at this! Look-look-look! Salmon! Real salmon! Meaty salmon! It's meat! Meeeaaaat. Me likey!"

Luna's slight look of concern escaped me. "Yes, I can see. Is that what you want?"

I plastered a faux look of indifference. "Me? Want the fishy? Oh no. No, no, no, no, no, no, no. Eenope, nope, nopey, nope, nope, nope. Nah, negatory, not really........yes."

The deck filled with the soft tittering of Luna. "Such theatrics, Celestia would be quite jealous. I commend your perfect performance of a needy foal."

"It's not a performance, Lunaaaa! You don't know the hell I've gone through, having to eat nothing but veggies for weeks, like a little kid. I'm a big man! I need my protein!"

"You need proper nutrients and vitamins along with essential minerals. We're ordering you a large cup of vegetables and you will eat every bite. That's final."

"Bah! You're not my mom! Hmmph!" I finish with a cross-legged pout.

"Daw," Cooed Luna, "Does somepony need their baby bottle? Do I need to set you on a time-out? Or, mmm, perhaps a spanking will dooo?"

Ruh roh! "Woah-ho-ho now! Let's take it down a notch ok, Princess? We're all civilized adults here...but I would like that milk bottle though."

Rupturing laughter spilled forth from both of us, leaving us both relieved that no other souls had witnessed our shenanigans. "I cannot recall the last time I have shared such unbecoming behavior with anypony aside from Celestia and Discord. Aaahhh, reminds me of days long before the crown, or the castle, or the curse. A much simpler time. Oh well, that's enough remembering, we need to order pronto. Waiter!"

On cue, the double-decker doors slid open allowing the griffon server to make his elegant entrance. "Beautiful night for fine dining if I do say so myself, but enough about you Princess Luna, ha-ha-ha, what can I get for you both?"

Me want fishy!, "I'll take the salmon, with extra lemons."

"Florette Sea and Earth Salad, with a glass of Romanee-Colti."

"Excellent choices, and your drink sir?"

"Lemon-aid." Luna gave me a funny look, while the waiter stared at me as if I had just slapped him. "...Er, soda?" Now he looked like I kicked his puppy. "...Mil-"

"He'll have a sparkling cider," Luna cut in, much to the relief of all three of us.

"Uh-huh. Since you two are our only customers this evening, your food should be out shortly." The waiter took our menus before leaving us alone once more, but not before uttering a few things under his breath. "Lemond-aid, soda, milk? What are we, some fifth-rate peasant kid's lunch menu?" He finished just as the doors closed shut.

"Yeesh, I fucked up the fine dining experience huh?"

"Big time. Never did enjoy it though, too little food, much too expensive. I recommended you don't visit here anytime soon unless you would wish for some added unsavory 'spices'."

"Heh, like I could ever afford to come to a place like this. Speaking of money, how exactly would I be able to use the royal tab thingy again? I tried to use it earlier, but they didn't know what I was talking about."

Luna proceeded to magic up a small round golden wax stamp, depicting the flag of Equestria with Celestia's and Luna's cutie-marks carved onto the Tree of Harmony. "You need to look for proprietors that utilize this royal stamp within their establishment. They will be posted at the entrance or register counter."

Faster than either of us was expecting, the doors opened once more with a silver tray and platter being conveyed by our waiter from earlier. Settling our food and drinks before us, the waiter retired back into the kitchen.

Luna hoisted her glass into the air, a clear indication of wishing to make a toast. I take a close look at the sizzling liquid that was my drink, hesitating me from joining Luna. "This is... alcohol, right?"

"Only in the barest of margins. Called Spicy Soda by some. I figured it was mild enough to be to your liking, or at least to satisfy our attendant."

"If it's the mildest drink they got on this gas bag, then I can't complain I guess." I hoist my drink into the air as well. "Did I tell y'all that I'm a teetotaler? An abstainer?"

"You mentioned it before, yes."

"OK, good, just wanted to make sure. Anyway, what are we toasting to?" I say as my glass hovers right next to hers.

Luna gives me a warm smile as she delivers her proclamation. "May we come to share many a joyous night such as tonight, for as long as you stay by our side." I couldn't help but wonder if there were any royal plurals used.

"Eeyup. What she said." *Clink!* "... Wait a minute, you actually enjoyed tonight? And you want to do it again? You ain't joshing me?"

"Why of course not. I used to bear the Element of Honesty you know. Why do you believe I think otherwise?"

"...I don't know. Never spent this much time alone with a lady before, let alone a magical horse princess. Couldn't really tell if your laughter was genuine or pity on my part."

A small look of hurt crossed her face. "You believe so little in me and yourself?"

"No-no-no! It's just... this is new water I'm treading in right now, ya know? Quality time alone with someone, not family. Never really done it before."

"... Would you like to do it again?" Luna asked.

"Huh?" Did I hear that right?

"Tonight, the time we spent together, would you like to schedule for another one?"

"... You mean... like a..."

"Very much so, yes," Luna replied before I could finish. Her gaze was fixated solely on my own eyes, bringing a whole new level of intensity.

Oh. Oh no. "I-I-I... but, um, but what about, ya know, the portal and me going home and most likely never coming back?"

"Austin, I know not how much time longer you may spend within our realm, but I know this, I have enjoyed tonight. I enjoyed our flight, our shared fright, your cheesy jokes that brought me delight-" I bit my tongue to make sure I wasn't daydreaming once more, "-I enjoyed our shared silence under the starry night. And I enjoyed you most of all. Perhaps I may be rushing ahead a little here, but I would be kicking myself for days on end if I were not to propose a follow-up of tonight before you have departed for home. So I must ask again, would you care to join me for another ride in the future?"

Oh, fuck. She...she can't be serious. "... Luna, you do realize what you're asking of me, right? When you take my whole situation into account, you understand my apprehension here, right?"

"I do. Do you accept my offer?" Her will remained solid.

...No, I can't. I won't. I shouldn't. "... We'll see what the future has in store, Luna." Dear God, please help me. What am I getting myself into?


"You just love to make my job harder than it needs to be, don't you, Princess Luna? Being fifteen minutes late for a pre-scheduled appointment we made days ago, is not 'cutting it close'. My night crew cannot afford to waste precious time and so too can't Austin. You know better than this." reprimanded Dr. Healthy.

"My deepest apologies, Dr. Healthy. The evening winds have proved to be far stronger than I initially realized. We were forced to cruise with a steady-going airship to compensate."

Dr. Healthy couldn't help but pinch the bridge of his nose before releasing a tiresome sigh. "*Sigh*, Such reckless behavior. What has become of all the princesses today? First Twilight, then Celestia, and now you?"

"Pardon? What of Celestia and Twilight, Doctor?"

"No time to explain I'm afraid for I know not, but suffice to say, they are ecstatic. Now, come along Austin, we must get the pre-procedures underway."

As the Doctor proceeds ahead to the operating room, I linger behind to utter some last words to Luna. "...As crazy and death-defying as tonight was, I enjoyed my night too, Luna. And you know... maybe I wouldn't mind another soaring ascension into the clear azure." Me and my big brain words.

Luna couldn't help but roll her eyes once more with a look of mirthful bemusement. "Is that supposed to be a yes?"

"...Maybe."

"*Sigh*, You are a hooffull, Austin. Good night, and good luck."

"Lone Star! Hurry up now!" Yelled out the Doctor.

"Good night. Your highness."


*Beep*...

*Beep*...

*Beep*...

"... *****, **** *** ****?"

"...Hugh, wuh? whooo?" I called out as I escaped the depths of dreamless sleep. Someone's muffled voice had stirred me awake, but I could not tell what was said or by who, but I knew there was more than one presence present. They continued to chat away, unaware I was coming around.

"***** ******, ***up. Th*** *re *ure?"

Gradually, my hearing regained enough strength to capture their voices clearly, with the next voice sounding like Twilights, "The math checks out Luna. It was the breakthrough we were hoping for, but we did not expect to find it so soon!"

"Breakthrough? Did someone break-in?" My hearing may have caught up, but my brain needed a moment more.

"It is good to see you awake and healthy once more, Austin," commented Celestia, "We come with great tidings for you."

"Perhaps both of you are rushing into this too quickly. I mean, have you had time to verify the math? I do not trust how fast you are ready to go through with this." Luna finished with quite a somber tone. From what little I knew about equine posture, her demeanor displayed...frustration?

"It's ok sister. As you may already know Twilight, she went through the trouble of quadruple checking to verify the data."

"Indeed," began Twilight, "like you I too was apprehensive at the discovery, but the research team and I have run the tests and crunched our numbers to the best of our abilities. We still need to calibrate the mirror's readings and tune it into the Elements frequency and inputting Discord's fragments into a compartmentalized data crystal is still underway, but suffice to say, I am confident that everything is ready, for the most part."

Everything Twilight said completely flew over my head, but I couldn't ignore the tension growing in the room. "Yeah, sorry but my brain is still kicking into gear, what are y'all talking about?"

"They're finished." Luna glumly delivered. "Austin... you can be home within the hour."