Up All Night To Get Umbra

by LewdChapter

Rating: mature
Tags: Princess Celestia, Sex, Human, Anthro, Anon, My Little Pony: Friendship is Magic, Second Person, Princess Cadance, Alternate Universe, Romance, Princess Luna, Porn, Fetish, Comedy, King Sombra, Profanity
Length: 8457

You get woken up in the middle of the night to help deal with a returning Queen Umbra

Few things are more irritating than being woken up prematurely, so your annoyance is pretty justified when a gaggle of royalty bust into your house at 2AM, ranting and raving about some evil queen called Umbra. Begrudgingly, you get out of bed to save the Crystal Empire, hoping something comes up to make this whole trip worth it...

WARNING: This story contains R63, hand-to-hand combat, blowjobs, cunnilingus, slightly unrealistic cocks and seminal volume, all of the positions, very mild inflation, and Anon.

Commissioned by TheWingman

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Published 2019-08-06 16:30:02 UTC
Last updated 2019-08-06 16:30:02 UTC

Up All Night To Get Some

You don't ask for much in life.

You pay your taxes, just like everyone else in this crazy, weirdo, alien horse world. You're a law-abiding citizen who just wants to get through the work week, hit up the bar on the weekend, bang as many hotties as you could before Monday, rinse, and repeat. Sure, you have a bit of a reputation for being a smarmy asshole, but you think you've earned the right to be a smartass, considering you were yanked from your home on Earth and spat out in this bat-shit crazy world called Equestria without your consent.

That was months ago, and the charm and whimsy of the magical land of horse-people had officially worn off. Now, working in the castle with the princesses, to try and establish some sort of link between here and Earth, had grown incredibly annoying for a myriad of reasons, not least of which being the hours. The princesses had begun to insist on keeping you there later and later (and not for any of the fun reasons two attractive women could keep you after work), and it had started to impact your sleep schedule. Tonight, for instance, you hadn’t gotten home until about 2 AM.

So you’re pretty sure that you’re justified in being intensely annoyed at being disturbed by a gaggle of royalty breaking into your home.

“What the actual hell are you doing in my house?” you say, sitting up in groggily in bed. At first, you think it’s only Celestia, but then, as your eyes adjust to the dark, you can make out three other shadowy silhouettes. You lean over to your nightstand and flip on the lamp, bathing your bedroom in dim, barely-adequate lighting. As the room floods with light, you can easily see who else decided to join Celestia in her trespassing.

Just behind Celestia is her sister, the thin, supermodel-esque figure of Princess Luna. Equestrian women tend to be quite a bit taller than human women, but Luna stands a bit closer to your end of the spectrum. By your best guess, she's nearly 6', which puts her sister at around 6'2". While Luna is slender, with long legs and a flat stomach, Celestia is quite a bit more buxom. She fills out the chest of her white gown quitewell, and the only thing that gets you through work every day is the promise of the Sun Princess' legendary cleavage. While the Regal Sisters are no doubt attractive, two women you would happily smash if given the opportunity, they're nothing compared to their niece.

Princess Cadance is a woman you've met very sparingly, which you theorize is due to her husband. Not that you can blame Shining Armor, even now as he stands a bit between the bed and Cadance herself. If you had your way, Cadance would be in bed next to you right then, married woman or not. You can't help it, she's got all your kryptonites; busty, curvy, thick. Somewhere between her aunts in terms of height, she's got a rack to rival Celestia's and an ass to eclipse the sun itself. Perhaps most alluring is the extra weight she had gained and fruitlessly tried to burn after giving birth to her daughter. This left Cadance wonderfully meaty, thick enough to make your mouth water. You vowed to yourself a long time ago to somehow get her alone and out of her dress. Definitely a tall drink of water, you’re normally pretty psyched to get an eyeful of the Love Princess.

Right now, though, you were more pissed than anything that she had woken you up.

“We need your help,” says Cadance. You roll your eyes, then turn back over in bed. “Anon. We’re talking about the fate of an entire kingdom here. This is serious.”

“What’s serious is the shitty security in this place,” you gripe. “How did you four get in here anyway?”

“You live in Canterlot, idiot,” says Luna flatly. “We’re your landlords.”

“Oh. Well, in that case, the garbage disposal is busted, when are you gonna send someone to fix it?”

“Is this really the only person who can help?” Shining Armor, someone you barely processed as being there, is clearly annoyed by your behavior. Fuck him, though, he’s not the one who got yanked out of a peaceful sleep after a long day of work. “We don’t have anyone more dependable? Or likeable?”

“As much as it burns me to admit it, trophy husband here has a point,” you say, just barely choking back a yawn. “Based on what you told me about your history, you deal with ‘fate of an entire kingdom’ level shit all the time. Don’t you have people for this?”

“We do, indeed,” says Celestia, her voice tinged with irritation. “However, this is a delicate situation that has no precedence.” You don’t say anything, so Celestia elects to continue her spiel. “Have you heard of Queen Umbra?”

“Should I have?”

“She’s a very powerful, wicked woman,” explains Luna. “The Queen of Shadows once ruled over the Crystal Empire, with the goal of adding all of Equestria to her conquered lands. She is immune to traditional magicks, and more cunning than about any other threat we’ve ever faced. We’ve managed to defeat her twice, but each time just barely. Every time she returns, she comes back more powerful than the last.”

“I don’t see what that has to do with me,” you mention, hoping to get these royal assholes out of your room before the damn sun came up.

“She’s come back again,” says Cadance. “And she’s taken my kingdom once again.”

“Ohhhh!” You look up at the prince and princesses, hoping to convey just how little you gave a fuck about all of this with just a simple glare. “I still don’t see why I should care. Or why you couldn’t get one of your henshin, Sailor Scout magic girls to do it for you.”

“This guy is an idiot,” grumbles Shining. “I’ll go deal with Umbra myself.”

“Do you want to be sleeping on the couch for the rest of your life?” asks Cadance, a tinge of irritation creeping into her voice. Ever the diplomat, Celestia slides into the conversation, hoping to reach an understanding.

“Simply put, this return of Queen Umbra is very different. She’s not here for conquest, or for vengeance,” explains Celestia with a tired sigh. “She’s here for a mate.”

You were starting to head back to sleep, but that got your attention in a hurry.

“I beg your fucking pardon?” you say, pulling yourself out of bed. You grab a pair of shorts from your dresser and toss them on. It’s starting to look like you wouldn’t be talking your way out of this so easily.

“From the best we can tell, she’s in heat,” says Luna. “And her heat is far more intense than any pony man could satisfy. A human, on the other hand…”

“You want me to fuck a dusty, million-year old queen so she’ll stop being mean to you guys?”

“For the record, Queen Umbra is only about thirteen-thousand years old, by our best guess,” says Celestia. “And a good chunk of that time was spent in another dimension that doesn’t have a concept of passing time, so she looks quite well for her age.”

“Furthermore, you probably don’t have to have sex with her,” Cadance clarifies. “Strictly speaking, we only need someone who interests her, to keep her busy long enough for me to charge my antaphrodisiac charm, and—”

“You’re telling me you have a spell for this and you still had to wake me up?” you groan. “Just have your hubby distract her and then zap the bitch back to whatever hole she crawled out of to start with. Why bother me?”

“Because, you dunce, you’re a human,” says Luna, obviously very tired with your shit. “If she gets a hold of a stallion, she may very well breed him to death. You, however, have a much better chance of survival, should things go south.”

“That, and I’m more expendable, I’m guessing?”

“Your words,” notes Shining with a frown. “And mine too, I suppose.”

“I assure you, Anon, if there was anyone else who could do this, I would not be here,” says Celestia. “But you’re least likely to die if she decides to have you, and therefore our best chance at besting her. All you need to do is occupy her attention, flirt with her a bit—”

“You’ve been doing as much with my sister and I for the past six months,” says Luna dryly. “So you’re at least in practice.”

“And, once you’ve held her attention for long enough, Cadance will cast her spell, and we can handle it from there,” finishes Celestia. “Please, Anon. We will make it worth your while.”

“You mean…” You raise a brow, not daring to dream.

“No. I do not mean.” Celestia shakes her head, apparently not happy with her only choice in chosen champions. “I meant more in the sense of treasure, or days off, or—”

“Show me your tits.”

It goes incredibly quiet at that point, nobody entirely sure they heard you properly. But you stand there, arms crossed and unwavering. You know that this is a bold request, and you know that you’d be severely reprimanded in any other circumstances, perhaps even banished. But you also know that you have the upperhand in these negotiations, and you can ask for basically whatever it is you want.

And what you want is a peek at the royal melons.

“I beg your pardon?” says Celestia, once she finally recovers from her shock.

“You heard me. I want to see your tits,” you say. “All of you. I’ll do this stupid Umbra thing, flirt with her or whatever, but in exchange, you have to show me your tits.” You can see the gears turning, and Celestia glances back to her fellow royals for a moment before negotiating.

“Just a flash,” she says.

“Tia!” snaps Luna. “You can’t be serious!”

“Extended flash. Fifteen seconds, minimum,” you demand. Celestia bites down on her lip, very visibly unhappy with her options.

“No touching.”

“Extended flash, and I get to take pictures.”

Again, the princesses have a quick little silent council, mentally talking things over among themselves. Luna is making no effort to hide her disapproval, vigorously shaking her head hard enough that you were worried her horn might come off. After their little pow-wow was finished, Celestia turns back to you and gives you a tiny nod.

“Deal,” she says. “Once Queen Umbra is squared away, we can discuss your little photoshoot.”

“Alright, then.” You head for your closet to find your best “seduce an ancient, evil queen” outfit. “Lemme just get dressed…”

Teleporting to the Crystal Empire makes this whole ordeal a bit easier to swallow, turning a six hour train ride into a six second snap of the fingers. You would have been fine with just going with Cadance, but Shining Armor had rightfully insisted he accompany you. You didn’t let that bother you, though. You’d get in that woman’s bed eventually.

“So, where to?” you ask as your feet touch down on the shiny, sparkly, incredibly impractical and unreasonable crystal road.

“She’ll be in the castle,” says Cadance, pointing ahead to the massive crystal structure. “We’ll follow a bit behind. If you get into hot water, just say ‘bunny rabbit’, and we’ll get you out of there.

“What is that, your safe word?”

“Can we hurry this up?” snaps Shining, a visible blush confirming your earlier joke as fact. “The longer we wait, the more of our subjects Queen Umbra may potentially hurt.”

“Alright, Captain, you’re the boss,” you say with a shrug. Whistling while you go, you strut forward into the Crystal Empire’s impressive castle.

The entire place seems deserted at the moment, with all of the guards and court jesters and whatever else gone. It’s sorta eerie, the silent, empty castle carrying a spooky, probably-haunted vibe. Not that you believed in ghosts. Even in this ridiculous world of people with fur, tails, horns, and wings, it seems to be agreed that supernatural entities are nonsense, horror movie bullshit.

It’s nice to know that there’s still some sort of normalcy in this bizarre life you lead.

“There. The throne room is just ahead,” says Cadance, pointing forward to the massive double doors. On either side stands a tall, fully-armored guard, wielding crystal spears that they use to block the entrance. Their eyes glow with this incandescent, otherworldly green light, with wisps of purple smoke occasionally floating out of the corners of their eyes. “Damn, she’s gotten our guards under her influence. Shiny, get a counterspell ready. I’ll put up a barrier, and… Anon, where are you going?!”

“I don’t have time for this bullshit,” you say with a yawn, boldly striding towards the guards. You figure one of two things will happen next; either your confidence will pay off and you’ll get through this unscathed, or these guards will kick your shit in and send you on your merry way so you can get back to sleep. You see this as an absolute win, no matter how things go.

You come to a stop in front of the guards, who don’t seem to even notice you. You cock your brow, waving your hands and snapping your fingers in an attempt to garner their attention. Nothing. You shrug your shoulders and reach for the door, pulling your hand back to avoid getting it chopped off by the sudden swing of the guards’ spears, forming an X in front of the throne room doors to keep you out. You glance back to the Crystal royals, rolling your eyes at the way they charge their horns with magic.

You swing your foot as hard as you can between the first guard’s leg, dropping him to his knees and potentially raising his voice a few octaves. You grab his spear before it hits the ground and swing the blunt handle at his buddy. You catch him in the side, then the leg, and, finally, you swing it upward and hit him in the dick. Both guards collapse onto the ground, barely conscious and certainly not capable of getting in your way anymore.

“I’ve got ‘counterspells’ too,” you say. You cock your head to the door. “We sure she’s in there?”

A sudden scream split the air, a man whose spirit sounds thoroughly broken. The scream is followed swiftly by an annoyed growl, like a dog that’s been denied his treat one too many times.

“WHY CAN’T EVEN ONE OF YOU WORTHLESS IDIOTS MAKE ME CUM, FOR FUCK’S SAKE?!”

“Pretty sure.” Cadance shrugs, grabbing your wrist when you reach for the door. “Wait. We didn’t really explain things super well.”

“What’s there to explain? Evil queen, wants to fuck, all you ponies are minute men,” you say, once again letting out a tired yawn. This really isn’t the sort of thing you want to be doing off of forty-five minutes of sleep. “What am I missing?”

“Umbra has an… aura to her. A boner field, for want of a better term.” Cadance lets you go, making the bold decision to trust that you’ll listen to a single word to come out of her mouth. “A stallion can’t get too close to her without being affected. And, while I’m sure you can take it… It’s something to be aware of. Don’t let your guard down around her.”

“Whatever. Can we do this already?” you groan. “I’ve got Zs to catch and tits to see.”

“My wife’s tits,” Shining reminds you. “Watch yourself.”

“Yeah, how is she your wife, anyway? Don’t you princesses take, like, celibacy vows or some shit?”

“Absolutely not,” the couple remark, one of them quite a bit more irate than the other. Shining glares at Cadance, who just gives a sort of smirk.

“Good to know,” you say. “Armor, you better stay out here. Like, actually, not just being a dick. Umbra’s influence might catch you.”

“I hate that you’re right…” grumbles Armor. He crosses his arms over his chest. “Fine. Cadance, if you need me…”

“Don’t worry, Shiny. It’ll be okay,” promises Cadance. “We’ll be back in bed before you know it.” She gives you a nod and, deciding that subtlety was massively overrated, you kick the throne room doors open, striding in.

The throne room is in chaos, with dozens of bodies strewn about the place. At first, you’re concerned, until you realize that the crystal stallions aren’t actually dead. Just completely out of gas in the tank. Directly across from you, standing before the crystal throne with her hand wrapped around the throat of another half-conscious guard, is the Queen of Shadows.

“Oh, fantastic,” drones Umbra sarcastically. She tossed the guard into the pile, dusting her hands clean. “Another useless, impotent mortal pony who will…” She trails off as her eyes fall on you, a devious glint shining in her eyes. “Or… Perhaps I was too hasty. You seem like you have promise.”

“Holy fuck, she’s hot,” you say. When Celestia said Umbra looked good for her age, you weren’t really sure what to expect. She was several millennia old, so “good for her age” could mean anything that wasn’t a mummy. But this is more than good for her age. This is good for any age.

She’s pretty tall, roughly 6’4 by your best guess. She only has to look up a bit to meet your eyes, and you’re a pretty tall dude. She’s also quite pretty, with sharp features, bold red eyes, a long, curving horn, and smooth, shiny, exquisite ebony hair. More important than her height and her mane are her assets, a department in which she is beyond blessed. Her tits are absolutely insane, struggling to be contained by her scanty, bordering on pointless, steel armor. Her hips are wide, connected to thick, juicy, meaty thighs that could crush a lesser man like a grape. You couldn’t see her from behind, but you thought it was a safe bet to say that she had an ass that would be very, very welcome to sit on your face.

“Charming. I am Queen Umbra, the Lady of Shadows,” says Umbra, taking a step forward. As her heels click against the floor, her boobs bounce hypnotically, drawing the attention of your eyes and your quickly stiffening cock. “Who are you, mortal, who dares address the Queen?”

“Yeah, I’m Anon. Cadance called me here?” You point over your shoulder, where Cadance is awkwardly standing, charging her spell. “She’s kinda pissed that you stole her castle or whatever, so she got me up out of bed to deal with you.”

“Ha! Her castle?” The Queen throws her head back and cackles, giving you a healthy eyeful of her bountiful cleavage. “The Crystal Empire is mine. This is my domain, and it was stolen away from me. I am merely here to reclaim that which is rightfully my own.”

“And also get laid, from what I’ve been hearing. What’s up with that, huh? You hit a dry spell?” The Queen doesn’t seem amused with your jokes, scowling and baring her sharp, dangerous, and admittedly pretty sexy, fangs.

“These worthless men… Most can’t even get out of their pants without making a mess of themselves near me,” grumbles Umbra. “None of these idiots could possibly satisfy me. You, however…”

“Yeah, I was thinking the same thing. And, full disclosure, I was kinda sent here to distract you while the wizard chick behind me figures out how to turn off your heat,” you say, ignoring Cadance’s protests. “But… Fuck that. You’re way hotter than I thought you’d be, so I think I’m gonna try to get you to bed.”

“Such a quaint little mortal… In my Empire, disputes are settled in duels, hand-to-hand. You will battle me. If I win, you will become my plaything until the end of time,” says Umbra. “If you somehow best me, then you may have me in whatever way you desire.”

“If I can beat you up, I get to fuck you however I want?” you ask. The queen nods, bringing a grin to your face. “Sounds good to me.”

“Anon!” snaps Cadance. You turn to her, confused by her wild gesturing to the throne. “My castle?”

“Oh. Yeah. Right. If I win, you gotta leave the Empire, okay?”

“You could never defeat me in combat, so sure. Why not?” The Queen of Shadows snaps her fingers, cloaking her right hand in onyx flames. “Shake my hand and the constraints of our duel shall become law.”

You shrug, then close the distance between you and the Queen. Cadance is still in shock, begging you to reconsider. Unfortunately, you’re still incredibly annoyed to have been woken up, so you’ll be damned if you’re not gonna get everything you can out of this trip. You grab Umbra’s flaming hand and shake, watching curiously as the obsidian fire harmlessly wrapped itself around your forearm. Your grasps break, and the flames dissipate, at which point the queen takes a few steps back.

“No holds barred. We battle with our bodies alone, no outside weaponry allowed,” explains Umbra. “We fight until one of us yields or is otherwise unable to continue. Are you ready, Anon?”

“Yeah, ready to get my dick wet.” You bring your hands up, hoping that you can remember some scrap of knowledge from your high school wrestling days. “Let’s do this.”

“Begin!”

Before you have much of a chance to do, well, anything, Queen Umbra is on you. She wraps her arms around your torso, pinning your arms to your side and threatening to squeeze the life out of your body. Although, if you absolutely must die, you can think of worse ends than being squished to death by some of the best tits you've ever seen in your life.

But you don't have plans to die just yet. You stamp down hard on Umbra's foot, causing her to help in pain and, more importantly, release you. As soon as you're free, you get a bit underhanded by thumbing her in the eye, just enough to stun her so you can make a retreat.

“You fight dirty,” growls Umbra, rubbing her eye gingerly. She flashes you a devilish smirk. “I like it.”

“If you ain’t cheating, you’re not trying,” you say with a shrug. She lunges at you, and she almost catches you on account of you being incredibly distracted by her sizable breasts. Luckily, you manage to snap out of your stupor before she gets her hands on you, stepping out of the way. “You’re pretty dirty, yourself. Attacking me while I’m distracted? That’s not very fair.”

“Fair doesn’t win wars, and winning wars is what I do.”

Again, she takes the opportunity to swing at you, this time grabbing you in a tight side headlock. She’s a lot stronger than you originally realized, her arms subtly toned and firm. Even still, you’re stronger, and you’re able to slowly pry her arms free of your neck. You pull her off of you, then swing your foot at her ankles, attempting to sweep her legs out from under her. She hops over your kick, then the next one, finally avoiding the third kick by twirling on her heel and spinning out of the way. You grin as the opportunity presents itself; With Umbra turned away from you, you can’t help but take a swing at her thick, juicy ass, chuckling to yourself at the loud slap and the way her booty jiggles. The queen stands up a bit straighter, her fists balled up and trembling slightly. She slowly turns on the spot, her face blooming bright red, and she snorted out a plume of black smoke from her nose. You’re sure that you just made the situation unquantifiably more dangerous for yourself, but you can’t help but grin at how annoyed and embarrassed you managed to make the queen.

“You will pay dearly for that,” she growls. “I hope it was worth it.”

“Kinda, yeah.” You grin, beckoning for more. Now, you’re in the driver’s seat, a place you’re very comfortable. “Don’t worry, I’ll spank the other cheek next time, keep things balanced.”

“Cheeky.” Umbra takes a clumsy swipe at you, which you easily sidestep. You get another opening and you do just as you promised; You slap Umbra’s ass a second time, even harder this time. “Quit it!”

“Very poor choice of words.” You smirk like the devil himself, wondering what else you can do to get in Umbra’s head (and, eventually, her pants). When you see her blushing face, inspiration strikes you. Time to turn on the charm. “You know, Queen Umbra, I was kinda being a jerk earlier but… You really are a beautiful woman. Your eyes are gorgeous.”

“W-what are you saying?” stammers Umbra. It seems like she doesn’t get complimented as often as you think she should be, which is both a shame and a blessing, because it gives you the opening you need. You catch her off guard with a sweep, kicking her legs out from under her and sending her tumbling to the ground with a tiny yelp. Before her back hits the floor, you reach forward and grab her by the top of her chest piece, leaving her dangling precariously a few inches from the ground. Her boobs had started to slip out of the metal garb a bit, but, to your dismay, it seemed she was wearing some sort of bandaging around her chest to keep her contained during combat.

“So? Do I win?” You ask with a grin. Umbra is too stunned to say much just yet, so you shake her gently, watching a bit more bandaged boobflesh slip free. “I’d hate to have to drop you on your ass, especially after the spanking I gave you. You’re bound to be sore down there.”

“I will end you, you insolent worm!” Umbra takes a few obviously half-hearted swipes at you, blushing as you pull her up and wrap your arm around her waist. “What in the seven hells are you doing?”

“I meant that, by the way,” you say, pushing aside the snide remarks to be genuine for a change. “Your eyes are stunning.” You release your grasp on the queen, snickering at how she yelped in surprise before you catch her again. “Come on, Queenie. I know as well as you do that you could’ve ended this early if you really wanted to. But, for some reason, you let me get the upper hand. Why not get things rolling?” You feign to drop her a third time, with similarly satisfying results. “Or I could kick your bubble butt for real. Your call.” You can almost see the gears in Umbra’s head turning, trying to worm out of this situation with her pride intact. But, after you flash her your pearly whites, you know that it’s game over for her.

“Fine. I yield,” says Umbra flatly, trying not to let on how glad she is to have lost. “As per our wager, I’m now yours to do with what you wish. So let’s just—”

You steal the rest of Umbra’s sentence with a deep, sudden, passionate kiss. She’s clearly surprised, but she doesn’t fight it, either due to her enjoyment, her warrior’s blood mandating that she honor her word, or a mix of the two. You break away slowly, taking pride in your ability to take a queen’s breath away.

“So… How do we proceed from here?”

“Yo, Cadance,” you call out. The Love Princess lets out an inquisitive hum from behind you, as if surprised that you even remembered she was in the room. “Where’s your bedroom?”

“Third door on the right,” she says, before it really clicks what it is you’re asking. “Um… Why?”

“Well, since you woke me up to deal with some magic nonsense that could’ve easily gotten me killed, I say you owe me.” You grab Umbra around the waist with both arms and hoist her up, slinging her over your shoulder like a bag of grain. “So I’m gonna fuck Umbra here in your bed. Cool? Cool. See you in the morning!”

And, without giving her even a moment to argue, you’re on your way to the royal bedchamber, with a flustered, embarrassed, angry-to-be-thrown-around-but-secretly-loving-it shadow queen on your shoulder.

This is where the fun begins

Cadance’s bedroom is nice and spacious, with a big, soft, cushy bed in the center of the room. The bedspread is beautiful, and clearly very expensive. It almost makes you feel bad, knowing the terrible, terrible things you plan to do on this nice bed. But you figure you’ll deal with that guilt later, and instead settle on locking the door behind you.

“Put me down this instant, you worthless wretch!” demands Umbra, battering your back with her fists like a little girl throwing a tantrum. “I am a queen, I am not meant to be thrown around like this!”

“Your call,” you say. You toss her onto the bed, smirking at her cute little yelp of surprise as she bounced off of the mattress. “But, just a quick heads up, that’s the last order you’re gonna be giving tonight. I get to have you however I want, remember?”

“Unfortunately.” Umbra looks you up and down, almost nervously. “So… What is it that you desire?”

“Well, for starters…” You pull your shirt over your head and, in one quick motion, pull down your pants. “You’re gonna blow me. Sound good, your highness?” Umbra’s eyes are wide as saucers, her mouth slightly gaped as her gaze pans down your body. You can’t really blame her for staring. Objectively, you’re pretty blessed down there; a thick, hard cock that was easily pushing 9 inches, both the savior and the bane of many women you’ve met in Canterlot bars over these past few months. “You okay there, Queenie? You look shell-shocked.”

“Gods above, you’re… larger than I anticipated,” says Umbra uneasily. She shakes her head firmly, suddenly gripped with fiery energy. “But I shall conquer it all the same. Do your worst.”

“Why don’t you get a bit more comfortable, huh? I don’t imagine having sex in full armor is particularly comfortable.”

She nods and, not taking her eyes off of you or your package, swiftly pulls at some string at her back, loosening the armor from her body. She drops the steel chest piece and shoulder pads to the ground, then went about pulling off her boots and weird loincloth thingy to reveal her absolutely drenched white panties.

"Someone's excited," you tease. Umbra growls angrily as she stands up, letting you get a good look at her body. Her stomach is a perfect blend of soft and toned, her abs lightly defined while leaving a bit of squish to her. You raise an eyebrow at the sight of a jagged, crooked scar going from her hip, across her middle and underneath the opposite rib. The longer you look, the more scars you notice, tinier ones on her thighs and her calf.

"I told you, idiot. I'm in heat," she reminds you. She notices your gaze and brings her hand to cover her stomach. "S-sorry about… Those. They’re not particularly attractive, I imagine…”

“Why apologize? Pretty sure you didn’t get hurt on purpose,” you say with a shrug. “I didn’t mean to stare, just kinda interested. Looks like you’re okay now, which is really all I’m worried about.”

“You… Don’t mind?” she asks carefully. Once again, you shrug.

“Scars are just tattoos with better stories. I dig em on you, really ties together the whole ‘badass, evil warrior-queen’ aesthetic you’ve got going on.”

“Well… If you say so.” She blinks, as if just then realizing where she was, and then slowly drops to her knees in front of you. “Enough about me. I hope you don’t plan on making me wait much longer.”

“Wouldn’t dream of it.”

Deciding now was the time for action, Umbra slides up to you, grabbing your cock gently in her hands. She admires your heft for a moment, inhaling your scent hungrily, before sliding your head past her lips. She wraps her soft, pillowy lips around you, messily slurping on your tip before taking you deeper and deeper. She’s quite good, which is unsurprising given how long she’s had to practice. You brush a lock of hair from her face before grabbing a tight hold of her horn and buck your hips forward into her face. You never go too deep, not wanting to hurt the queen (although you weren’t really sure if you were even capable of such a thing), but Umbra is starved, and she takes more and more of your length with each thrust.

“Quite the go-getter, hm?” Umbra peers up at you, visibly annoyed by your admittedly cocky, shit-eating grin. “Think you can handle more?” Umbra nods, mumbling some sort of confirmation around your cock, which is more than enough for you. With a tight grasp on her horn, you yank her forward and shoving your cock deep into Umbra’s throat. You groan in delight, smirking at how she seems to lose herself in swallowing your cock. For such a proud warrior, the Queen of Shadows sure seems to enjoy servicing you, something you’re sure she’d blame on her heat were you to bring it up.

The reason why doesn’t really matter. What does matter is that she’s good, really good. The way her throat twitches around your length, the way her thin, snake-like tongue wraps around you and works up and down your shaft is growing to be too much to take. You grip her horn even tighter, pound her throat even harder, until you can’t possibly hold off any longer. Your cock twitches, and you groan as you fire off thick, hot ropes of cum down Umbra’s throat. She’s surprised at first, the volume of cum taking her off guard, but she just barely manages to gulp it all down. She pulls back out of your grasp, milking your cock with her hands and depositing the last of your cum onto her tongue, which she dutifully and enthusiastically swallowed.

“I hope you have more in the tank,” remarks Umbra, wiping the spit from the corners of her mouth. “I’m going to need much more than that to be satisfied.”

“Oh, for sure. But, for the time being… Lay on the bed, will ya?” Umbra cocks her brow, but does what you said. You drop down onto the bed, slithering forward and spreading Umbra’s legs. “Mind ditching these panties for me?” Umbra rolls her eyes, and gives her fingers a snap; her panties burst into onyx flames, vanishing in a flash and exposing her puffy, juicy pussy, and the cute little tuft of well-trimmed black hair above. You grin, which only serves to make the queen blush.

“What now?” she asks. In place of a verbal answer, you grab her gently around the hips, diving between her legs and tonguing at her cunt. Umbra gasps sharply, not at all prepared for this, but she’s clearly not opposed. One hand grips the bed sheets tightly, while her other grabs you by the hair, pulling you in closer. Taking that as a sign to pick up the pace, you do just that; you slither your tongue up and down her lower lips before wiggling your tongue into Umbra’s cunt. The Queen tastes sweet, addictive, and so you lap at her pussy dutifully. Each hitched breath and shaky moan from Umbra driving you to go deeper. You kiss at her cunt, feeling her tense as you wrap your lips around her sensitive clit.

“Gods above…” moans Umbra. You can feel her getting closer, her legs trembling and her core quaking. You give her one last push, devouring her pussy and savoring her sweetness until you feel her tense, wrapping her legs around your head and throwing her head back in sheer ecstasy. She arched her back and howled in pleasure, her cunt clenching around your tongue and her entire body quivering with delight as she came. She rode the wave of her orgasm as you continued to slurp and lap at her pussy, finally stopping when all you can hear from the queen is her ragged, labored breathing.

“There, now we’re square,” you say, although you have no intention of stopping there. “Now that I reciprocated, I can dick you down with a clean conscience.”

“You better not be mocking me,” panted Umbra. “Because, if you attempt to leave me like this, I cannot ensure your continued existence.”

“Queenie, babe, be real. You think I could possibly walk away from you right now?” You flash her a smile, then make the bold decision to shoot your shot. “I actually really like you. Like, ‘more than a one night stand like you’. Maybe when we’re done here, and I can confirm that you’re not going to eat my soul or whatever it is you do, you’ll let me take you to dinner?”

“Shut up and fuck me, idiot,” grumbles Umbra. She blushes bright red, refusing to meet your gaze. “If you somehow satisfy me, perhaps I will consider granting you the honor of dining with me.” She glances at you, growing more flustered at the way you grin at her. “B-but don’t hold your breath!”

“Alright, Queenie. Another wager, then. If I manage to scratch all your itches, you have to go out with me.” You shimmy up to her, sliding your cock against her cunt, teasing Umbra for just a moment before sliding into her. She’s perfectly tight, her pussy almost sucking you in and hugging you tightly with her hot, velvety walls. You barely waste a second before setting your body in motion, thrusting your hips fiercely into Umbra. It’s a lot for her to take at once, but she takes it like a champ, holding you in close and working her hips in time with yours to get as deep as possible. Her pride and reservations had long since melted away, replaced with fervor and desire.

“Fuck, harder! More!” demands Queen Umbra, clutching you tightly. With a smirk, you slow your pace, much to Umbra’s annoyance. “What are you doing?! Your queen commands you to—”

“And I command you to remember who won our duel,” you remind her. “I told you, you’re done giving orders.” You pull back, threatening to pop out of Umbra if not for her grasp on your shoulders. “So, if you want more, I suggest you ask nicely.” Umbra grumbles something under her breath, her words becoming a breathy moan as you slip your hand under her bandage-bra and tweak her nipple between your fingers. “Hm? Sorry, didn’t hear you. Could you speak up?”

“If you hadn’t defeated me in combat, I would have you executed,” growls Umbra. She swallows her pride, and looks you in the eyes with a burning fury and an even more blazing lust. “P-please, fuck me harder. There. Are you satisfied, you miserable little—Oh, fuck!”

You decide to, right at that moment, slam your hips forward and bury every inch of your cock into the Queen of Shadows. Entirely unprepared, Umbra tenses up beneath you, letting out another quivering moan as she came again. You piston your hips forward, gritting your teeth as you quickly followed in the queen’s footsteps; Her tight, perfect royal pussy milks you for your cum, which you happily give her, shooting an almost unreasonable amount of cum into Umbra’s womb.

“Gods above… I needed that,” says Umbra breathlessly. You crawl off of her, laying flat on your back. “What?”

“Sit,” you say simply, pointing to your somehow still-hard dick with a sly grin. “Hop to it, Queenie. I’m not through with you by a damn sight.”

Umbra nods before crawling over to you, throwing one leg over to straddle you. She grinds against your cock for a moment to revive it for round 3 (not that it needs it), and finally lowers herself down onto you. She impales herself slowly, letting out a moan as she bounces up and down on your cock. You just fold your hands behind your back, taking a moment to enjoy the view, when you notice that pesky swath of bandages.

“Ditch the top,” you instruct. “Let’s see those tits.” Umbra nods and, with another flare of black flames, her bandages disintegrate. Now free of their restraints, her big, round, heavy breasts are allowed to breathe freely, and you can’t help but grab and squeeze one while the other bounced in time with Umbra’s motions. “Perfect. You’ve got a fantastic body, your highness.”

“Mmm… Thank you…” She seems surprised for a moment, as if she hadn’t meant to say that out loud, but she can’t stop now. She’s so sensitive, so needy, so hormone-addled, that you can tell that another orgasm is already approaching her. It’s only fair that you match her tit for tat, so you fire your hips into motion, drilling deeper, harder, faster into Umbra. “A-anon… I’m close again…”

With a grin, you bring your hands up and firmly clasp them onto Umbra’s big, juicy ass, using her bountiful booty as a grip while you shoot your hips faster than before. She lets out a yelp, falling forward onto you as you pound her cunt without mercy. You latch your lips onto her, kissing her deeply, digging your fingers gently into the flesh of her butt, bottoming out in her just in time to give the queen another creampie. She barely has enough breath to moan as she reaches her peak, squeezing you for more of your seed, each thick, abundant jet of cum causing her another shudder of pleasure.

“You cum so much…” she breathes, glancing down at her stomach. It looks like she was starting to fill, her starting to balloon slightly from the almost comical amount of cum you were able to fill her with. “I feel so full…”

You sit up, holding Umbra upright in your lap for just a second before pistoning your hips upward. Umbra looks like she was expecting a brief break to recover, so your sudden jump into round 4 takes whatever she has left of her breath away. Umbra wraps her arms around your neck, holding on tightly as you bounce her up and down on your cock.

“Hold on tight,” you say. She does as she’s told, just in time for you to stand up, hoisting her into the air. Instinctively, she wraps her legs around your middle, clinging to you like a sloth as you have your way with her. You can hear her quietly moaning in your ear, quiet whispers for more, which you’re all too happy to give. You can feel her tremble and quake again, and she leans forward to gently nip on your neck while you fuck her. You’re nervous at first on account of her fangs, but she’s being very careful about them, so you don’t pay it much attention. When you have a woman as desperate as Umbra on your hands, you have precious little time to worry about anything other than pleasing her.

Once again, she lets out a shaky moan as she cums, biting down a bit harder on your neck. It seems like her buttons are getting easier to push, as are yours. You wonder if it’s due to Queen Umbra’s so-called boner field, or maybe you two are just starting to click as lovers. Either way, you let out a groan as you erupt, filling her once again. With each load, her belly seems to swell a bit more, giving her a visible, albeit subtle, roundness.

You toss Umbra back down onto her back, giving her a scant few seconds to catch her breath before you flip her over and pull her thick, beautiful ass up. You give her another firm spank (she seems to be enjoying this more and more, letting out a little moan as you hit her), sliding your still throbbing cock into her cunt. You hold her by her waist as you piston your pelvis, the air filled with the sound of your hips slapping against her ass.

“Mmmmm… Please…” moans Umbra, unable to form a cohesive sentence. “Hair…”

“Hm?” You grab a fistful of her pitch black hair, tugging on it firmly and arching her back and yanking a moan from deep within the queen. “You mean like this?”

“Yessss!”

Well, this is hot. And a bit freaky. But mostly hot.

You pull Umbra’s hair as you plow her, reducing her to a quaking, quivering, fuck-drunk mess. You imagine that it must’ve been a while since she’d been fucked like this, for a multitude of reasons. There’s the obvious fact of her being ten thousand years old, and much of that time was spent in some sort of Phantom Zone dimension. Then, there’s the fact that pony men don’t typically last very long compared to humans. But, more so than that, you think it’s because of her pride and status as a powerful, independent warrior. Most people wouldn’t dare try to dominate their queen in the bedroom.

“Gods above, I’m cumming!”

Luckily for Umbra, you’re not most people.

“You don’t quit, huh?” you pant, feeling the strain from the night’s activities catch up to you. You grit your teeth, bottoming out and cumming deep inside Umbra once again. She was starting to reach capacity, with cum dripping from her well-fucked cunt and onto Cadance’s expensive sheets. She drops down onto her side, and you collapse beside her, sliding up and spooning behind her. “I think I’ve got one more in me. Sound good?”

“Mh-hm…” Umbra rubs her belly with an awe and whimsy, amazed by how full she was. “Fill me up… Please…”

You raise Umbra’s leg and ease back into her cum-stuffed pussy, hoping to give the queen one last load. Of all the ways you’ve fucked Umbra, this might be your favorite; you have this unmistakable closeness, with you able to smell the smokey, strangely alluring scent of her perfume. It’s nice, a tender moment after a night of doing everything in your power to get under her skin.

To your surprise, she cranes her head back to kiss you, a kiss you happily return. You pull her closer, pounding her as deep as you could go and earning one last orgasm from the Queen of Shadows. She moans into your mouth as she cums, her slithering tongue against yours, and you couldn’t hold off anymore even if you wanted to; you let out one last, strong eruption, filling Umbra to burst with hot, sticky cum. Finally, you pull out, letting a bit of cum spill out of Umbra’s used, abused, satisfied pussy. She rolls onto her back, reaching her hand between her legs to scoop the excess cum back into her. With the way you filled her, her belly is looking stuffed, and she could easily pass for being a couple of months pregnant. More importantly than that, though, is the look of satisfaction and contentment etched on her face.

“Satisfied, your highness?” you ask smugly. She rolls her eyes, darting in to steal a quick kiss. “I’ll take that as yes. I guess I better go wash up and head home, huh?”

“Don’t you dare leave this bed, mortal. Your queen commands you to stay by her side.” Now that Umbra has been thoroughly satisfied, she seems to have regained some of her sharp demeanor. “You will stay with me until morning, and you will cuddle me.”

Or maybe not.

“Alright,” you say with a shrug. You pull your queen in close, wrapping your arms around her warmly. “I dunno about you, but I’m dying for some sleep…”

Epilogue

Shining Armor snarled angrily as he approached his bedroom, the trio of princesses following close behind. This wasn’t how things were supposed to happen. He already wasn’t happy with needing to depend on someone like Anon to begin with, and now he finds out that this jerk was fucking the queen in his bed. He pounded on his own door, ignoring the disapproval he was receiving from the royals behind him.

“Personally, I don’t see the big deal,” said Celestia. “He did do what we asked him, albeit… using unorthodox tactics.”

“You just want someone to say you have nice tits, don’t you?” droned Luna. Celestia flashed her sister a glare, before finally hanging her head in defeat.

“It would be nice…”

“Open the fucking door!” shouted Shining. Cadance rolled her eyes before pushing her husband out of the way. “What the hell, Caddy?”

“You’ve never been the most rational thinker when you’re angry,” said Cadance with a sigh. She produced a silver key from her pocket, which she used to unlock the door. “Relax, Shiny.”

“I’ll relax when the bastard is out of my bed.”

“I’m sure he was mindful of his surroundings and refrained from making a mess.” Cadance shook her head at her husband’s vitriol, then pushed the door open. “He may be a bit rude, but he’s not—”

Cadance stopped as she stepped into the room, the air hot and heavy with the stench of sex. She frowned slightly as she ventured forth, her fellow royals following behind, to see the sleeping body of Anon holding a sleeping, snoring Queen Umbra in his arms. The cum that formerly filled Queen Umbra seemed to have leaked out over the last few hours, leaving a pool of Anon’s jizz on the expensive royal silk.

“You were saying?” droned Shining. “I said he was a dick. I was right, you were wrong. Any questions?”

“Yeah, how come you never fuck me that good?”

“Let’s leave them be,” said Celestia, stopping the marital dispute before it could really start. “Whether you like it or not, Anon has saved your kingdom. Let the man sleep.”

“We’ll replace your sheets,” said Luna, leading the party of four out of the room with a shake of the head. “And get ready to pose for those pictures…”

As the royals exited the scene, Anon slowly opened his eyes, letting out a tiny yawn. Fucking an immortal queen into submission was no mean feat, and he was still exhausted, but he thought he heard voices. He looked down at the still slumbering shadow queen on his chest, let out a tired grunt, and went right back to bed.

Anon didn’t ask for much in life. Now he was happy to finally get his well-earned sleep.