Nightmare Moon Walks the Night

by TheVClaw

Rating: mature
Tags: Nightmare Moon, Porn, Comedy, Profanity, Random, Shining Armor, Sex, Anthro, My Little Pony: Friendship is Magic
Length: 4282

Luna is back to her villainous self, and is eager to reclaim her place as Equestria's supreme ruler. Unfortunately, her magical abilities are just as limited as her finances. Fortunately, she's able to sate both through the world's oldest profession~

Nightmare Moon is back! After years spent in remission, the evil side of Luna has been reclaimed once more. And with none of Equestria the wiser, the mare was more than eager to take her throne once more.

Or at least, that's what the Princess would want to do, if not for her magic and finances being severely limited.

Fortunately though, Nightmare Moon's looks haven't depleted in the slightest, nor has her insatiable lust. And what better way to quell her hunger, and also regain her financial strengths for the sake of her power, than to take a few shifts performing the world's oldest profession: Prostitution~

Note: This story was a commission for Silverstorm, and is a M/F clopfic that features adultery, prostitution, oral, anal, and condom-drinking. If you're curious about commissions, or want to show your support for a freelance writer, please check out my Official Patreon Page for more content~
Also, the cover page is a piece done by longtailshort, whose work can be found here: https://derpibooru.org/tags/artist-colon-longtailshort

Published 2020-09-04 04:20:01 UTC
Last updated 2020-09-04 04:20:01 UTC

Chapter One: An Awkward Reunion

“Hmph… You would think that there would be more potential clients on a Friday night…”

The lone mare sighed bitterly while standing alone at the street corner, only able to talk to herself for the time being. Since the only buildings around here were all abandoned, she had to try her hardest not to feel too overwhelmed in such a desolate region of Canterlot. Fortunately, since the streetlights were all still shining brightly, she felt the slightest bit safer while beneath one of the spotlights illuminating her form. Not to mention, the blinking traffic lights nearby, as well as the flawlessly bright moon that hung high above the cloudless skies, only helped to make her feel less exposed by herself.

“Hmmmm…” Her dark muzzle smirked as she glanced down at herself, absolutely loving the attire she chose to don for tonight’s debaucherous fun. She was already well-renowned for her petite hourglass figure back at the castle, which she usually tried to conceal behind regal gowns or plated armor; but since she was embracing her more… sinister side for a change, she was flauntingly revealing her physique with a tight, dark-purple corset that nearly resembled lingerie. Dark, lacey pantyhose went up the length of both her curvaceous legs, and were just barely able to stay together around the girth of her plump thighs. She was also wearing a bright-purple miniskirt, which wasn’t even long enough to conceal the bottom curves of her juicy cheeks. And with the sultry clear heels that she was wearing over her hooves, the mare now resembled a street-walker far better than she had a Princess.

Of course, since the silver insignia of her former evil self was embroidered in the middle of her corset, just beneath her thick and perky breasts, it was obvious that this wasn’t just the Princess of Equestria’s Night. On this night, much like most other weekend nights away from Celestia’s surveillance, Princess Luna was prowling the streets as her alternate self: Nightmare Moon.

Or at least, prowling was only one of the things that the revitalized villain wished to do in her current form. Unfortunately, due to a number of limitations on her end -- both magical and financial -- Nightmare Moon could only wait for a car to show up while she reapplied her lipstick. As she huffed to herself with a disappointed pout, she stared into her pocket-mirror to make sure her makeup was applied correctly. “For crying out loud, how hard is it to find a man in this city?”

After licking her lips with her forked tongue, which allowed the ruby-red coat to glisten brightly in her mirror, Nightmare Moon gave a sly smirk which caused her fangs to poke out slightly. She was sure if her sister saw her right now, she would throw an absolute fit about the skanky outfit she was wearing out in public; of course, she would probably also send her to the moon again if she realized what else her little sister was doing. Luna may have been aware of how dangerous it was to try and regain her villainous self in public; but since she was Nightmare Moon now, all that she cared about was getting a proper fix to sate her more… carnal cravings~

Well, partially that, and also making some quick cash on the side to help fund her plans of conquest. She may have already been wealthy as a Princess, but she didn’t want to just suck random guys’ cocks for free. That just felt weird.

“Ugh, maybe I should try going over to…” Before Nightmare Moon could finish muttering to herself, her eyes widened when she saw a pair of headlights coming in from the distance. She wasn’t able to see what kind of car it was, even when she tried to narrow her eyes in focus. However, her ears perked when she heard the engine revving down, indicating that it was beginning to slow down towards her. That realization made the mare grin more suggestively, and she stepped back from the curb to stand in a more revealing pose; one of her legs went out to help expose her voluptuous figure, as her eyes remained pinned on the car in wait. “Hmmm… that car looks expensive~”

Even though the sight of that sleek luxury sedan got her muzzle grinning wider, it wasn’t until she got a good look that her expression lessened immensely. “And… very familiar…”

Nightmare Moon didn’t want to say anything, since she was sure that a lot of wealthy gentlemen in Canterlot had that same type of car in their garages. Not to mention, since the windows were tinted with a similar shade of black as the paintjob, the mare couldn’t exactly see who was actually driving it. When the car stopped in front her at the curb, she had the slightest bit of hesitance when the passenger door opened. However, after looking around to make sure no cops were nearby, Nightmare shrugged before getting into the car without question.

Unfortunately for Nightmare Moon, as well as the stallion who was behind the wheel, the mood instantly went from optimistic to awkward.

“L-Luna!?”

Shining Armor, who was wearing a casual black suit instead of his Royal uniform, went completely wide-eyed when he realized his Aunt-in-Law was the mare he picked up for a “ride.” Nightmare looked equally as uncomfortable, and had to blink a couple times upon seeing Shining as her newest client. “Ummmm… Well, this is unexpected…”

The car remained idling out in the middle of nowhere, as the two ponies just stared at each other in increasingly uncomfortable silence. Shining’s cheeks blushed profusely, and he bit his lip with a look of dread and remorse. Meanwhile, Nightmare had to readjust herself in the passenger seat, which caused an awkward squeak to be heard from her bare thighs rubbing against the plush leather. If Shining wasn’t mentally shitting himself, he likely would’ve made a joke about that accidental noise; but as his eyes peered up and down the mare’s form, all he could think to do was ask feebly, “So, ummm… are… are you wearing a costume, or…”

Nightmare closed her eyes with a strong sigh, not wanting to clarify her new form before her nephew-in-law. Nevertheless, considering the circumstances, she didn’t feel too nervous to bring up one of her hands, and flicked her fangs with a finger to indicate their authenticity. “Nope. I… I’m Nightmare Moon at the moment…”

“Ah…” Shining looked away with his blush deepening, unsure of what else he could say to his newly-villainized Aunt. “And… And that means you’re like… evil now?”

“Ugh!” Nightmare wasn’t wanting to keep this conversation going, and glared back at him while asking, “Shining, do you really want to ask questions when you came out here for me?”

“Ngh!” The stallion’s muzzle pursed tightly shut, and he looked away from her with a more uncomfortable expression. “I-I wasn’t… I mean… I-It’s not like--”

“Stop.” Nightmare brought out her hand to place before Shining’s face, giving the same motion as a crossing guard keeping a car from speeding through an intersection. When the stallion finally glanced back at her guiltily, he could see the neutral look that she was giving in return. “Given the circumstances here, I think it’s very clear that we’re on even ground right now. If you don’t tell anypony what I’m doing, I’ll show my respect by keeping silent about you as well. Deal?”

Shining had to blink a couple times in confoundment, clearly needing a moment to process Nightmare’s logic. But considering their shared predicament, the Prince was quick to put out his hand and shake her’s. “Umm, d-deal! I promise, what happens tonight stays between us.”

“Good to hear~” Nightmare gave a confident smile while shaking Shining’s hand, and then motioned her head towards the road before them. “Now, how about we pull into that parking lot beside the warehouse over there? Nobody ever comes by there, so that can give us more… privacy~”

Nephew or not, Nightmare made sure to emphasize that last word with a very suggestive grin on the stallion. Shining tried not to cringe while sitting in the driver’s seat, and gave a silent nod while the mare put on her seatbelt. He silently drove down the block towards their destination, where he was grateful to find an empty parking lot with brick walls all around for added protection. He was still blushing nervously when he parked in the back corner, but Nightmare’s content smile made it clear she was able to trust their discrete spot.

“So…” The mare unbuckled herself, and leaned back in her seat while shooting a lustful smirk back at Shining. “Might I ask why you’re leaving my niece at home all alone?~”

“Nnnghhh…” Shining winced hard while averting his eyes from his Aunt-In-Law. “I, uhhh… I’ve been at home alone for the past two weeks. Cadance went on that Royal summoning to the Gryphon Kingdom, remember?”

“Oh, right…” Nightmare Moon’s brows raised up in realization, and she gave a brief shrug before saying, “Yeah, I was supposed to go there too. Or I mean, Luna was supposed to be there, I guess. Heh heh…”

Shining didn’t say anything, but he still looked uncomfortable the longer he sat across from the revived villain. Even though he knew better than to let such a dangerous detail slide, it wasn’t like he could do much while being caught requesting her services. Not to mention, as his eyes glanced back at the ‘Princess” and her alluring smirk, they slowly traveled downward to gaze at those plump, juicy thighs. Despite knowing how old the mare technically was (even if the millennium spent on the moon didn’t count), Shining audibly gulped when he saw just how attractive Nightmare Moon looked in that skimpy getup.

“Heh~” Nightmare’s grin widened just as much as her legs, and she took advantage of the car’s spacious seating as she revealed the bright pink thong just beneath her miniskirt. Shining’s eyes nearly bulged out of his skull, and he was left speechless when she spoke in a teasingly sultry tone. “My goodness, Shining… I wouldn’t have guessed you would be this riled up after such a short amount of time away from the Missus…”

Shining winced in a mixture of shame and confusion, not wanting to admit to himself how hot Nightmare Moon looked in the passenger seat. Nevertheless, her cheeky remark prompted him to say through his blush, “W-Well, I… I’m kinda used to having that kind of attention… Y-You know, Princess of Love and all…”

If she wasn’t in such a precarious position as she was with one of Equestria’s most skilled fighters, she likely would’ve made a mocking retort questioning his answer. But instead of rubbing the salt of infidelity into his wounds, Nightmare merely nodded her head and asked, “So, were you wanting anything special for this occasion? I can’t give a ‘family discount’ or anything, but I can certainly make your night worthwhile~”

“Uhhh… Heh heh heh heh…” Shining didn’t want to appear so bashful before a former (and technically current) foe; unfortunately, the stallion ended up chuckling with a feeble blush while looking away from her bashfully. He scratched the back of his neck as he tried to speak coherently, despite how much his voice started to stammer. “W-Well, I… I wasn’t going to ask for a discount or anything. I-I’m not that cheap.”

“I certainly hope you’re not…” With that, Nightmare Moon reached down with both hands, and gripped the waistband of her panties beneath her skirt. As she repositioned herself in her seat, Shining’s jaw went agape upon seeing her slide down that thong until it wrapped around her ankles. She then shot a lustful grin back at the stallion and said confidently, “because for what I have to offer, I’m certainly not cheap either~”

Shining may have felt weird about making such an exchange, but the dorky smile that went alongside his brief chuckle made it clear that he didn’t mind paying his Aunt-In-Law. He reached into his pocket, and pulled out a thick wad of cash folded in a rubber band. “Ummm, w-would this do?”

“Hmmm…” Nightmare Night’s brows rose up as she took the wad of bills, and quickly counted out the amount. Since Shining was smart enough to have hundreds instead of twentys (or even tens, which Nightmare was dismayed to learn was surprisingly common from clients around this district), she gave an impressed smirk by the time she tucked the cash in her corset. “Alright, this is definitely enough for my time~”

Without warning, Nightmare leaned over the center console to press her lips against Shining’s. The Prince’s eyes widened immensely in shock, but eventually closed as he moaned weakly into her muzzle. After only a moment of hesitation, the stallion leaned in to return the gesture, and began to make out with his wife’s Aunt without much shame. Even though he knew how wrong it was to indulge in this kind of adultery, especially with a revived villain, the flicks of her forked tongue against his own caused his cock to throb hard within the tight confines of his trousers.

Nightmare Moon continued to make out with Shining, but one of her hands went over to grasp the tent that was growing from his crotch. Shining let out a muffled moan, but kept swapping spit with the mare as she openly groped his erection through the fabric. Without even needing to look down, Nightmare unzipped Shining’s fly so that his thick, rigid cock could jump out like a Jack-In-A-Box. And with an effortless moment of precision, the villainous mare proved her skills to be well-taught as she immediately began to stroke his cock without pause.

“Ahhh!!~” Shining wasn’t expecting to receive such an upfront handjob, and finally pulled his lips away from her to moan out deeply. His legs squirmed quite a bit, but his cock was left unobstructed as it twitched and throbbed in Nightmare’s grasp. The mare smirked with a lustful gaze down at his member, obviously impressed as she licked her lips. Even though a couple strands of precum were already beginning to trickle down his length, she wasn’t going to let such a generous payment go to waste.

“GNNGHH!!” Shining reeled back in his seat when she bent over the console, and her lips slid over his throbbing head. The Princess let out the briefest moan when she caught the taste of his syrupy pre against her tongue, but her hand continued to vigorously stroke his length. Meanwhile, Nightmare’s eyes closed to better savor Shining’s musky flavor, and her lips wrapped tightly around the top of his shaft. As her fingers began to get coated in his pre, her lips and tongue worked diligently to allow more spurts to shoot to the back of her throat.

“Mmmmmm…” Nightmare Moon tried to take her time with fellating the Prince, appreciating every hard throb that she felt between her drooling lips. Even as smears of her lipstick clung onto Shining’s cock, he didn’t seem the least-bit upset as he brought his hands down over her head. He clenched his eyes shut while moaning direly, trying his hardest to maintain his resolve. Of course, even with the high price he paid for this mare’s slutty mouth, his hips couldn’t help jolting upward in an attempt to thrust into Nightmare’s hungry muzzle.

Eventually, Nightmare Moon’s head was bobbing up and down the length of Shining’s cock, with her lips tantalizing every inch of his shaft. Shining couldn’t stop moaning, but his boisterous cries were thankfully unheard from the outside of his car. Because of that, neither of them were interrupted while Nightmare got that cock to throb more profusely in her hungry maw. Shining kept pushing her head up and down, clearly eager to shoot a load right down her gullet. But alas, just as he felt himself reaching the peak of his incoming climax, he gasped out in shock when she pulled off his member with a wet pop.

“Nnnnghhh!!” Shining shuddered hard in his seat, mostly due to the cold air that hit his saliva-coated cock. Meanwhile, Nightmare was still grinning lewdly as she pulled out a condom at the ready, and expertly applied it over his twitching member.

“Don’t worry, my ‘Prince,’” she cooed with a teasing smirk up at him. “I just want to make sure we both have a little fun here~”

As soon as his cock was properly wrapped in the lubed latex, Nightmare moved herself across the console so she was hovering over his lap. Much to Shining’s shock, despite how little room he thought he had, the mare was able to get herself in position while sharing the driver’s seat. There proved to be enough headroom for her to get over his lap comfortably, as well as to get her ass right above his twitching cock. And with a single motion downward, Nightmare was able to get both of them to gasp the moment his head made contact with her puckering hole. “AAAAHHH!!~”

Due to the condom’s lubrication, as well as her experience handling clients back there, Nightmare didn’t need much foreplay when it came to getting some penetration. When Shining’s thick head slipped past her ring, Nightmare reeled her head back with a heavy moan while savoring that taboo sensation. Her hole stretched tightly around the girth of his shaft, and hugged every inch it claimed as she pushed herself down. Shining had to bite down on his fist while shuddering hotly beneath her, unsure of how much he could take of her villainous lust.

“Nnnnnffffff…” Nightmare Moon’s experience proved to be nothing short of efficient, as she managed to claim the entirety of his shaft in less than a minute. She moaned out in elation the moment she felt his balls pressing up against her backside, as well as from the subtle throbs that pulsated deep inside of her. Even though Shining’s endowment wasn’t the largest she ever encountered, the mare still shivered in taboo delight from how well it filled her up. Without even thinking, Nightmare brought one of her hands down to feel the very tip of his cock, which was nestled in far enough to leave the slightest bulge just beneath her belly-button. “Oooohhhhh, that’s a good one~”

Before Shining could even take a moment to process the alluring pressure of Nightmare’s ass, he groaned through his teeth upon feeling her move back up his shaft. The villainous mare moaned out deeply as her hole slid up his length, and her nerves tingled intensely from the bout of emptiness that came alongside it. Of course, just as the back of her shoulders touched the car’s ceiling, she bit her lip with a heated huff while that plump cockhead remained inside of her. She could feel every hard, throbbing motion of his member as her hole clung to it tightly, leaving Shining in a particularly overwhelmed state below her smirking form.

“Nnnnffff… Oh Shining, you have no idea how lucky you are~”

Then without warning, Nightmare Moon moaned out as he allowed her legs to buckle, and she fell back down his shaft with the aid of gravity. She belted out a piercing cry as she felt that thick, rigid cock spearing her once more, and his balls collided hard with her ass. Shining moaned out just as heavily, and had to pull the back of his seat so he could lie back and take the villain’s thrusts. Nightmare may have been doing all the work, but she didn’t seem to mind while his payment was securely nestled in her corset.

“AAAHHHH!!” Nightmare Moon pulled herself back up, but didn’t linger too long when that cockhead was pressing against the inside of her ring. Instead, she just barreled straight down again with her moans lingering on, while her perky breasts jiggled against her chest from the constant movement. Her impact may have been hard enough to make Shining groan out, but he didn’t try to stop her when she went back up for more. Instead, the Prince’s hands came up to tightly grasp both sides of her waist, holding her steady while she rode his cock without pause.

Outside in the parking lot, the shapes of their bodies could just barely be seen through the tinted windows; however, the constant rocking motions of the car made it clear what was going on inside. Nevertheless, as she felt that cock throbbing harder inside of her with every hearty thrust, Nightmare couldn’t have cared less while rocking the car back and forth. Her strenuous motions continued on as she glided up and down his twitching shaft, causing the head to begin and swell up inside of her in preparation.

“AAAHHHH!! S… S-Shining!!~” Nightmare Moon had her eyes tightly shut, but she tried her hardest to catch the Prince’s attention as she used her free hand to needily rub at her clit. “Nnnghhh!! T… T-Tell me when you’re about to cum!!~”

“Aaahhhhh!!~” Shining had his seat fully leaned-back, and his legs couldn’t stop squirming while taking every thrust of the mare riding his cock like a mechanical bull. He could feel how badly his cock was pulsating inside of that tight ass, and his breaths grew increasingly rapid as he came closer to fruition. “I… I-I think I… I think that I’m about to--NNNNGHHH!!~”

In a sudden moment of shock, his lustful admission was cut short when Nightmare Moon pulled out of him in an instant. Her ass made a wet pop as it unlodged from his member like a wine bottle, leaving his cock to twitch painfully hard while wrapped in the condom. The Princess rolled down the window, and pulled off that prophylactic to toss out into the parking lot. Not caring about Canterlot’s strict littering laws, the Princess was quick to apply a new condom around his cock before he could release.

“Nnnnfffffff…” While Shining was left reeling with a deep and confused blush, Nightmare Moon furiously jerked his cock while it was wrapped with a fresh condom. “C’mon, soldier boy~” she purred insistently with a hungry grin. “I know you can fill this up for your future ruler~”

“AAAAAHHHH!!!~” Even though he would’ve preferred to unload inside of the mare, Shining was left in a highly titillated state from her constant pumps to his shaft. He couldn’t stop throbbing in her grip, even as she spoke like a true villain to press his more taboo buttons. He had no idea what she was wanting with his semen, or why she needed a second condom to make the deposit in the first place. But since he was already so close to finishing, Shining was lost in euphoria by the time his hips writhed upward for her. “MMMGHHH!! I’M GONNA… I’M GONNA--AAAAHHHHH!!!~”

Shining and Nightmare Moon moaned out at the same time, with the Princess shuddering hard to the sight of that reservoir tip filling up like a balloon. Shining sunk into his seat with a dire cry as he climaxed hard in her grip, and flooded the condom with multiple spurts of his creamy load. By the time Nightmare was fully finished jerking him off, she smirked with a lick of her lips when she saw how bloated the condom got around his cock. She made sure to keep a tight grip to avoid spillage, while Shining’s condom was nearly tripled in size and filled with his milky white jizz.

“Aaahhhhh... Now that’s what I wanted tonight~” Nightmare Moon carefully pulled off the condom, leaving Shining’s cock twitching in his open lap while coated in cum. Meanwhile, the mare returned to her passenger seat, and leaned it back so she could better enjoy her hard-earned treat. Since Shining was left moaning tiredly with his eyes closed, he wasn’t able to take notice when the Princess brought the open end of the condom to her muzzle. And like the complete deviant she was, Nightmare Moon closed her eyes as she squeezed the contents of that condom right into her open mouth. “Mmmmmmmm…”

Her throat could be seen convulsing as she guzzled down the Prince’s creamy seed, which caused her to moan softly by the time it was all trickling down her throat. After taking a deep breath, and tossing that second condom out the car window as well, Nightmare Moon leaned back as she savored the pure taste of testosterone that clung to her tongue. Her slitted eyes glowed for a brief moment after her consumption, indicating that her condom-drinking wasn’t just some perverted fix from her side-job. Fortunately for the villain, her victim didn’t seem to notice her powers being slowly regained while she was seated right beside him.

“Mmmmm… J-Just a few more…” After shuddering to herself contentedly, Nightmare Moon glanced back at the near-comatose stallion laid back in his seat. She smiled down at him warmly, and bent in to give him a final kiss on the lips. “Thank you so much for your help, Shining. And I promise, what happened will stay between us~”

Nightmare then pulled her panties back up, shivering a bit when she felt the string of her thong nestling up against her sensitive hole. Instead of having the stallion drive her back to her stop, Nightmare Moon stepped out of his car while it remained idling in the parking lot. And as she exited the lot to trot back to her corner, the mare gave a devilish smirk as she went to reapply her lipstick along the way.

The End