Anon vs. The Nightmare Moon Timeline

by Bendy

Rating: mature
Tags: Random, Sex, Human, Anon, My Little Pony: Friendship is Magic, Alternate Universe, Nightmare Moon, Romance, Second Person, Comedy
Length: 4173

You end up in a dark Equestria, where the sun never shines. Soon enough you meet Nightmare Moon, which will surely bring about your death. However, you got a most unconventional weapon to defend yourself.

You end up in a dark Equestria, where the sun never shines. Soon enough you meet Nightmare Moon, which will surely bring about your death. However, you got a most unconventional weapon to defend yourself.

A big thanks to my editors: Jay The Stormtrooper, Art de Triomphe, forestpip, and Papa Dragon

Published 2017-02-23 14:20:01 UTC
Last updated 2017-02-23 14:20:01 UTC

Unconventional Weapon

A heavy sigh left you, the human as you stared out the window of your bedroom into the dark, moonless night sky, wishing it was lavender in color and the moon was out. You were only dressed in white underpants. For quite some time you stared up at the stars of the universe, hoping that some hot alien chick was looking back.

Just when you were about to turn around, you saw a shooting star fly across the sky.

“I wish to tap the greatest butt in the multiverse! Princess Luna’s butt!” you shouted out your wish.

A moment later your body vanished with a flash of blinding light.

The next thing you knew you found yourself standing on a paved path, before a stone bridge. The night sky above was lavender in color. A fine black tuxedo appeared to have been put on you during the teleportation.

You gulped in fear at the sight of a dark and spooky castle atop a hill beyond the bridge. You turned around to see a dark and spooky woods, shrouded in a dense fog.

You rubbed your chin, pondering what to do. “Creepy woods or creepy castle?” you thought out loud. There came a loud howl from the woods, causing you to shiver and whimper in fear.

“Uhhh, creepy castle it is.” came your voice, low and nervous.

With great haste, you ran across the bridge, followed by running up the hill along the path toward the safety of the castle. Upon reaching the huge, light blue wooden doors of the castle you pushed them wide open, making a dramatic entrance.

You found yourself in a massive, dark blue hallway. You looked up and saw a huge glass, triangular-shaped skylight which stretched its way across the entire ceiling and you were able to see the beautiful lavender night sky above. There were many alcoves along both sides of the hall, in the middle of each was a flaming torch with light blue flame. Draped over the floor was a dark purple carpet, stretching down the hall before it met a short flight of stairs, leading onto a solid stone, square shaped platform. And upon the platform sat a massive throne.

Sitting on the throne was a very large equine, slightly bigger than a Shire Horse. She had a jet black coat, a pair of huge, nearly basketball-sized, teal-colored eyes. Upon her back was a pair of huge, feathery wings; a dark blue helmet covered her head with a long, black horn worthy of a Spartan warrior’s spear protruded from a small opening on her helmet. Her dark blue ethereal mane flowed like the night sky, filled with small, shimmering stars.

And of course, she had a massive, plump backside. Her huge bubble butt was a lovely sight to behold. Upon each fat cheek was blotches of dark purple, with a crescent white moon. You knew that butt, it was Nightmare Moon’s butt.

“HOW DARE THOU ENTER OUR THRONE ROOM WITHOUT KNOCKING!” she roared in an extremely loud voice, quickly flying across the room.

Nightmare Moon slammed her thick, mighty hooves hard upon the floor before you, creating massive cracks due to her super alicorn strength. You yelped, nearly falling over from the small earthquake she created.

You silently stared up in terror at the incredibly intimidating alicorn before you. You felt weak and insignificant before her mighty form, your whole body was trembling in fear before her narrowed, harsh gaze piercing your very soul. If she was strong enough to shatter stone, you could only imagine what she could do if she struck you with her hooves.

For the next several minutes, the massive dark alicorn continued to stare at you with narrowed eyes, sizing up your small, pitiful form when compared to her.

“VILE CREATURE! WHY HAVE THOU COME HERE?!” she roared, lunging forward to push her head right into your face, nearly causing you to fall over.

You mumbled feebly in fear, not being able to form a coherent sentence.

“THOU IS NOT BUT A COWARDLY WHELP! WE FIND THY PANSY MUMBLED SPEECH MOST ANNOYING!” she said, powering up her horn with deadly magic. “PREPARE TO DIE!”

With your life depending on it, you with utter desperation and with great speed reached your hand out to the back of her head, placing it firmly upon the back of her ear. Almost immediately, you proceeded to begin scratching it, hoping against hope that this would be your salvation from certain death.

Nightmare Moon’s eyes widened in surprise. A soft coo soon left her, loving the feel of your hand scratching her ear. You sighed in relief when you saw her magical aura dissipate. Nightmare Moon simply stood there, making low, soft moans and quiet horsey sounds at the amazing feel of your hand.

She practically melted at your touch. The massive mare leaned her head over to the side of your neck, proceeding to gently nuzzle you, purring in bliss as you continued to scratch her ear.

A shiver of fear coursed through your body at the feel of her razor sharp teeth gently brushing against your neck. However, despite how sharp her teeth were, she did not leave a single cut on your skin.

“Thou art indeed a coward,” she whispered softly into your ear. ”But, We cannot find it even in Our icy cold heart to destroy one with such amazing appendages. Plus, We are starting to find thou most handsome.” she spoke softly, before shifting into a far more harsh tone. “We demand thou do more things to Us with thine appendages, or face Our wrath!”

“Uh, what do you want me to do?” came your voice, low and nervous.

She did not answer, instead flashing her horn with blinding light. The next thing you knew, you found yourself standing before a massive, dark blue love heart-shaped bed, with Nightmare Moon lying on her back, giving you a warm smile, her cheeks blushing a little red.

“We wish thou to rub Our belly.” she said softly, giving you bedroom eyes.

You gulped in fear, sitting yourself down on the bed beside her. The dark alicorn uttered a low moan when your hand made contact with her quite sizable, upper belly. The soft fur of her coat felt warm to the touch.

Not willing to test her patience out of fear, you quickly went about rubbing her belly. Nightmare Moon moaned aloud at the tender touch of your hand rubbing her belly.

“Oh, yes!” she cried out in bliss, before shouting. ”We love this! But go lower!” you moved your hand a little lower. “A lot lower!”

You whimpered in fear, moving your hand to get barely out of reach from touching her large, soft mounds that was her crotchboobs.

“LOWER!” she demanded, shaking the bed on its legs.

As her ladyship ordered, you went onward to begin gently rubbing the soft, pillowy mounds of her breasts. Nightmare Moon craned her neck back, unleashing a loud neigh at the feel of your hand rubbing there.

“Neehhhaaa! We love this! We shall appoint thou our royal masseur!” she cried out in pure bliss.

For quite some time you continued to rub her tits with a most nervous smile on your face. Nightmare Moon loved every minute of it, moaning aloud as her marehood became damp with her juices.

Eventually, Nightmare Moon spoke in a small, soft voice. “We command thou to stop now.”

You stopped rubbing her breasts, lifting your head up to look at her in fear.

“Show us the full potential of your appendages by using your tender touch upon our most precious place!” she shouted.

With a gulp, you proceeded to shift over on the bed, moving yourself between her long, thick, powerful hindlegs. Below you was her most plump, glistening marehood. You quickly took off your shirt, throwing it over your shoulder.

You looked up to see Nightmare Moon smiling down upon you, her cheeks were blushing profusely. That was all the indication you needed, before you went forth to gently place your hand upon the outer plump lips of her vagina.

The dark mare cried out, her legs kicking weakly. Taking that is a good sign, you then began to run your index finger slowly around her lips.

“Oh, yes! That feels so wonderful.” she said in a most blissful tone, before shifting into a harsh tone. “Don’t tease us too much. We want thine appendage inside us soon.”

For the next several minutes you continued to gently rub her vagina. Nightmare Moon moaned aloud and made quiet horse sounds, loving the feel of your hand’s loving touch.

When you believed enough time had passed, you decided to slowly insert your hand into her vagina. The tight walls of her marehood clamped down hard upon your hand, to the point it felt slightly painful.

Once your entire hand was inside her marehood, you began to gently rub and squeeze the soft flesh between your fingers.

The dark alicorn made loud whinnies in bliss. You kept massaging her insides, driving Nightmare Moon wild.

“Yes! Yes! Yes!” she screamed.

You continued to pay tender affection to her vagina, her loud moans and neighs were music to your ears. Your hand was soaking wet with her juices.

“Go deeper into Us!” she demanded.

With a gulp of fear, you slowly began pushing your arm deeper and deeper into her hot, squeezing marehood. Nightmare Moon nickered loudly as you drove more and more of your arm into her. Eventually, you buried your entire arm inside her.

The soft, wet, and powerful walls of her marehood clamped down hard upon your arm. You tried to pull back, but your arm wouldn’t budge, she was simply too strong. Making do, you began gently rubbing the deepest layer of her marehood with your hand, causing her to utter loud happy whinnies.

You continued to do this for quite some time, gently rubbing her insides with your hand, while she squeezed hard on your arm.

Just when you thought you’d gotten used to her squeezing marehood, you felt her powerful vagina squeeze your arm extremely tightly, to the point you hissed in pain.

“NEEHHHAAA!” she screamed in pure ecstasy.

Jet after jet of her marecum blasted out from her vagina, soaking your entire form with her creamy essence, smelling faintly of blueberries. Such was the quantity of her cum you soon began to look like a snowman.

Nightmare Moon sighed in bliss, lying her head back against her pillow. You slowly pulled your arm free of her vagina, her powerful, squeezing walls making it difficult to do so at a faster speed. You eventually managed to free your whole arm, now soaking wet with her marecum.

For quite some time, you remained in place sitting between her legs. Eventually, the dark mare stood up, her massive form casting a dark shadow over you.

She jumped off the bed, before turning around to give you a harsh glare.

“Servant! We demand thou to sit down at the foot of the bed!” she spoke in a harsh tone.

You gulped in fear, before shifting over to the bed’s end, placing your feet down upon the warm and soft carpeted floor.

Nightmare Moon made her way to stand over you, her mighty form towering over yours even more while you were sat down before her.

“Strip servant!” she demanded.

With a whimper, you pulled down your pants to reveal your rock hard member. You were scared all right, but somehow you could not help but get turned on nonetheless.

The dark mare frowned at the sight of your cock. Nightmare Moon slammed her massive, heavy backside hard upon the floor, creating a huge crack in it by the sheer weight and power of her rump.

The dark mare looked over your member with a most disappointed expression upon her face.

“Thy small phallus is most pathetic.” she spoke in a harsh voice.

You sighed deeply, lowering your head in shame, feeling inadequate before the large dark mare.

“But thou hast shown to be a most good servant, so We shall reward thou regardless.” she said softly.

You shuddered in fear when she dropped her head, easily capturing your entire cock into her muzzle. Her pointy sharp teeth brushed gently against your member. Despite how sharp they felt, they didn’t leave a single mark upon your cock. Your cock was so small it did not reach her throat.

Nightmare Moon hummed in approval at the taste of your dick, before proceeding to gently suck on it, creating a wonderful feeling of squeezing and releasing. You cried out in bliss. The amazing feel of her mouth was too much, you could feel your release already quickly approaching.

Nightmare Moon giggled from around your member from hearing your cries of bliss. The dark mare then began to use her huge, long, thick tongue to gently lick your member all over.

A most disappointed groan left her when you finished a mere minute later, unleashing a small amount of cum into her mouth. However, she moaned in bliss at the taste of your cum when she swallowed it down.

Nightmare Moon lifted her head to give you a broad smile with her sharp teeth. “Thou tastes wonderfully salty. We shall enjoy feasting on your love cream again.”

You gave no answer, too scared to speak.

Without a word she made to stand up, then hopped up onto the bed, before laying herself down upon it. Once there, she gave you a warm smile, patting the empty space on the bed next to her with a hoof.

“Cuddle with Us, good new servant.” she said softly.

As she requested, you shifted over and lay yourself down next to her. Once beside her, she wrapped a hoof around your waist, and then pulled you close to her, bringing your head to rest against her silky soft, flowing mane.

For quite some time you merely lay against her. The only sounds in the room were both of your quiet breathing and the beat of your hearts.

After quite a bit of time had passed Nightmare Moon decided to break the silence. She released her hold over you, pulling her head back to stare at you curiously.

“Why did thou come here, little one?” she inquired, speaking in a soft voice.

“I wished upon a shooting star to tap the greatest butt in the multiverse, Princess Luna’s butt.” you confessed, in a low and fearful tone.

A single tear fell down Nightmare Moon’s cheek, her lower lip quivering, overwhelmed with emotion.

“Thou likes Our butt more than Our sister’s bigger and fatter butt?” she spoke in a soft voice, before shifting into a harsh tone. “Choose thy next words carefully, or We shall smite thee.”

Deciding action was better than words, you quickly shifted over to make your way over to her massive backside. From there, you leaned down to leave a soft kiss on the crescent moon upon her cutie mark.

You looked back over to Nightmare Moon, to see tears of joy falling down her cheeks. “Tell Us thy name most handsome gentlestallion.” she spoke softly.

“My name is Anon. And I love your big moons.” you proudly declared.

“Oh Anon, thou art such a good servant. We wish for thou to make sweet love to us.” came her voice, low and soft. “Mount us from behind, our little lover.”

You stood up to quickly make your way behind the huge, prone mare. You drooled at the sight of her massive backside. Her bubble butt was perfectly round. Each thick, fat cheek had blotches of dark purple, with a crescent white moon. Her plump posterior was truly a breathtaking sight.

You wasted no time to begin worshiping her butt. You placed both your hands firmly on her massive ass, that was so wide you could barely reach her cutie marks upon both sides of her huge cheeks. Without delay, you began to rub along the wide expanse of the squishy soft flesh of her massive ass, the dark mare moaning in bliss from the wonderful feel of your hands.

After hearing that, you then began to squeeze the two massive mounds together, sinking your hands deep into the thick layers of her flabby soft flesh. Like soft dough you squeezed and rubbed her ass to your heart's content, loving the sight of her soft fat being depressed from your hands applied pressure. For the next several minutes, you payed homage to dat ass, by squeezing and rubbing her massive rump all over, her cries of ecstasy driving you onward to worship her massive, bootylicious fat ass.

The heat and the lovely blueberry smell of her marehood began to drive you wild. So, with that you lunged forward to bury your face between the thick mounds of her massive rump. From there you began to lick her plump vagina.

You ran your tongue in a slow circle around her plump lips surrounding her marehood. You moaned in bliss at the taste of her sweet juices, and you loved the sound of the neighs and moans coming from her.

When you were done licking the outer area, you decided to drive your tongue as deep as it could go into her hot marehood.

“NEEHHHAAA!” she screamed in pure ecstasy.

Hungrily, you licked her out with glee, the blissful sounds she uttered only driving you onward, her legs jerking wildly from your loving mouth’s attention.

You continued to service the dark mare, licking her marehood without stop.

“NEEHHHAAA! she cried out, unleashing her marecum. Thick spurt after spurt of her cum fired out from her vagina, soaking your entire head with thick globs of her creamy goodness.

“Thou… is...truly...a...gentlestallion.” came her voice, low and breathless. “Now, please make love to Us.”

The dark mare raised her massive rump high, spreading her cheeks wide to give you better access to her marehood. You pressed forward, poking your member against the hot entrance of her marehood. You grabbed her bountiful soft black buttcheeks, resulting in your hands compressing the wonderfully soft flesh deeply, before you pushed into her.

You hissed in pain at the feel of her tight, hot, soft and wet walls of her vagina squeezing your cock painfully tight. Nonetheless, with great determination you went deeper and deeper into her, Nightmare Moon moaning all the while as you did so.

Unfortunately, you reached your limit far too soon inside her. With a sheepish smile you looked up to see Nightmare Moon. However, she was smiling warmly back at you.

“Worry not lover, thy small size matters not. For my mighty alicorn vagina can adjust to even your tiny phallus.” she spoke softly.

“Yeah… but I always wanted to bang your butt with a ridiculously large penis.” you said in a low, somber voice.

“Then thou shalt have it!” she shouted excitedly.

You could feel a slight tingling sensation course through your cock, followed by a most wonderful feeling of your dick pressing deeper and deeper into her as your member grew in size. Your balls began to become heavy, bloating outward. The beautiful dark alicorn moaned aloud as you drove inch, after inch of your growing shaft into her. You sighed in bliss when your member had grown to the point it made contact with her deepest barrier. When it reached there, your cock stopped growing, your balls now as large as grapefruits.

For a long time you merely held your shaft deep within her, content to just feel the warm and snug feeling of her marehood squeezing your cock. Each and every inch of your long and thick, magically enhanced dick was squeezed by the powerful walls of her vagina.

“Make love to Us, handsome ape!” she called in a happy voice.

You didn’t need to be told twice. Slowly, you pulled back, the tight, squeezing walls of her vagina making it difficult to do so. Your new magically-augmented member held strong against her powerful alicorn vagina tightly squeezing your manhood.

You pulled back to the point of nearly exiting her, before gently pushing forward, back into her tight, hot depths. When you reached her furthest point, you slowly pulled back, before gradually pushing into her again, and doing the same again when you made it to her deepest point, her cries and neighs driving you onward.

Over time, you began to pick up speed, going a little faster each time your member made contact with her deepest point. Your large balls began to slap hard against her backside when you began to pick up considerable speed.

Nightmare Moon closed her eyes, her tongue lolling out of her mouth as she made a series of low whinnies.

The room became engulfed with the sounds of flesh slapping against flesh, moans, groans, and quiet horsey sounds as both you and Nightmare Moon became lost in the sea of sexual euphoria.

Repeatedly, without stop you thrusted hard into her. You grunted and moaned aloud, loving the feel of her walls tightly squeezing your long and thick cock as you thrusted back and forth against her. Your hands began to squeeze the massive cheeks of her ass even tighter, the squishy soft fat being depressed deeply from your tight grip.

You pulled your right hand back, before unleashing a hard slap upon her cheek, Nightmare Moon uttering a loud whinny as you did so. You smiled like an idiot, happily watching her big fat cheek smack against the other one with a loud, audible sound of flesh slapping against flesh.

“Do not hold back! Slam into Us!” she shouted.

With that, you upped the ante and began to slam into her like you were using a Krogan Warhammer. Her powerful alicorn muscles were more than capable to withstand your powerful thrusts.

You and the dark alicorn mare made sweet love. You pulled on her tail, causing her to scream a loud neigh, before you began to slam into her with reckless abandonment. Drool began to drip from her mouth all over her pillow as you continued to thrust into her.

On and on you continued to slam your massive cock into her, your heavy balls making a loud slapping sound each time they made contact with her massive backside. Gone mad with lust, you proceeded to continuously slap the holy hell out of her ass, each slap making her utter a loud neigh.

Each cheek smacked against the other one with a wonderful sound of flesh slapping against flesh. The warm and soft walls of her vagina squeezed your member tightly within her depths every time you slapped her ass.

A tingling sensation coursed through your rod, singling your impending release.

“Oh Moony, I’m about to cum!” you shouted.

“YES! Unleash inside Us!”

As your lady commanded, you made one last powerful slam, grunting loudly as you drove your dick as deep as it could go into her wanton depths, before painting her insides with thick creamy spurt, after spurt of your cum into her marehood.

“NEEHHHAAA!” she screamed in ecstasy, cumming upon your cock.

The massive quantities of cum inside her vagina, both yours and hers, was so much it began to overflow. It started out as a mere small leak first, before spewing out creamy glob after creamy glob of human and alicorn cum out from her marehood, spraying all over the bed beneath her.

You basked in the wonderful afterglow, feeling your softening member deep inside her hot, soft, and wet marehood. You gasped in shock, when you noticed her coat began to quickly turn from jet black to dark blue.

No Longer were you balls deep in Nightmare Moon. You were now balls deep in Princess Luna.

“Thank you, Anon. Thy love for Our rump has saved Us from Nightmare Moon. We no longer feel Our backside is bony thin and ugly when compared to Our sister's bigger and fatter posterior.” she said in a soft voice, tears falling down her cheeks.

Outside the window, you saw the sun rise over the horizon.

Suddenly, there came a blinding flash of light, before an even larger, white alicorn appeared next to the bed. An alicorn you were familiar with… at least by porn. It was Princess Celestia.

“You’re telling me, it wasn’t the day thing that made you Nightmare Moon?! You were just jealous that your butt was smaller than mine!” she screamed. “If I knew that I would have just hired the most hung stallion to mount you from behind a thousand years ago.”

“Please sister, don’t be angry,“ said Luna softly.

Celestia simply growled in answer.

“We art most sorry for locking thou way in the moon. If We invite thou to a threesome with Anon here will that help settle things between Us?” she said softly, staring at the white alicorn with pleading doggy eyes.

Princess Celestia sighed deeply. “Yes, that would help a lot to rebuild our friendship.”

The End