Why Not Both? (Overlord)

Why Not Both? (Overlord)

A/N: Why Not Both? was a commissioned two-shot originally written from October to November of 2021. Posting it up here and now as a one-shot for people to enjoy!

Summary: When given the choice between Velvet and Rose, the Third Overlord makes the obvious decision... both. Duh.

Themes: Threesome, Rough Sex, Breeding

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As the Overlord steps into her bedchambers, Velvet wastes no time in calling out to him. Lounging on her bed as she is, she presents quite the tempting profile, a sultry smirk on her lips and a seductive tone to her voice.

"At last, my Black Knight has come to save me from that lecher."

Indeed, Sir William's remains lay exploded in the room behind the Overlord, the once righteous and heroic Paladin turned corrupted and deviant Cult Leader cut down by his enemy after a titanic battle. Velvet was to be Sir William's bride... before the Succubus Queen came along and twisted him around her little finger, resulting in Velvet not getting anything at all.

Still, one could argue that the Overlord hadn't come to this place to save Velvet or anyone, really. And as the side door to the chamber opens up and the Overlord's current Mistress, Rose, steps in, a look of irritation and disgust crosses her features. Hands clasped together politely in front of her, the red head sniffs indelicately as if she's smelt something foul.

But then, to be fair, Rose is Velvet's older sister... and needless to say, the two have never gotten along very well. Calling out to the Overlord, Rose tries to keep things business as usual.

"Sire, I discovered a way to strengthen your Brown and Blue Minions while you were on this expedition."

Over on the bed, Velvet scoffs and lets out an airy laugh.

"Common bribery, Rose? I thought that was beneath you!"

The air between the two sisters bristles tensely as the helmeted Overlord looks back and forth between them. However, before either of them can say anything more, he points his weapon towards the door Rose came in through. Without missing a beat, the Overlord's small army of Minions all march right out the door.

As the door closes behind them, the Overlord stomps over to Rose and before she can react, picks her up and tosses her over onto the bed beside her sister. As she lands with a feminine 'oof!', Velvet rears back in surprise at well, neither woman expecting to be in such... close proximity to one another. Just as they're starting to process the change in circumstances, a fire spell washes over both of them.

For a brief moment, Velvet and Rose shriek in panic, believing that they've been set alight, both of them blazing under the new Overlord's abject Evil... but no, that is not the case. As quickly as the flames encroach, they are also gone. In their place, they leave Velvet and Rose entirely naked, the two sisters having had their clothes burned right off of their bodies, while their beautiful bodies themselves have been left completely untouched.

Looking over to the Overlord, neither woman can do anything but gawk at what they see. Stripped out of his armor, the Overlord stands there in nothing but his helmet. His massive, broad, chiseled chest is on full display... and covered in more scarring than either Velvet or Rose could have imagined. Meanwhile, down betwixt his legs, his bait and tackle are in more than working order. Already rising in anticipation, the Overlord's sizable cock throbs and pulses with purpose as it points towards the sisters on the bed.

"S-Sire..."

Rose's confusion, bewilderment, and embarrassment are all palpable, even as the Overlord advances on the bed. Letting out a mocking little laugh to hide her own insecurities and shock, Velvet reaches out and tweaks one of her sister's naked nipples, causing the red head to yelp and focus on her for a moment.

"He means to test us, sister dear. Is it not obvious? He's going to fuck us both and only then will he decide which of us he likes better."

Rose's eyes widen at that and for a moment she looks like she wants to disagree, like that can't possibly be it. But it's obviously the case and even Velvet's older, prim and proper sister recognizes as much after having it presented to her so clearly. Blushing as brightly as her hair color, Rose nevertheless squares her bared shoulders and clenches her jaw in resolve.

"V-Very well. Then a c-contest it is!"

Both sisters look at each other intensely for a moment, neither planning to lose here. Then, they turn back to face the Overlord... just in time for them to slap their faces against his massive cock. In their moment of distraction, he'd crawled up onto the bed and knelt in front of them, leaving the naked beauties blushing as they stare down the barrel of his dick.

Still, not to be outdone by the other, neither one of them waits a second to begin. Velvet is the more enthusiastic, but Rose has no intention of losing to her younger sister in this arena, no matter what advantage the raven-haired slut might have. Both of them suck and slurp and swirl their tongues along either side of the Overlord's cock, leaving him grunting in enjoyment as he brings his large, masculine hands down atop both of their heads.

Despite Velvet starting out the more aggressive of the pair, Rose soon shows that she's the more efficient and it's not long before the Overlord directs her mouth onto his cock properly, sliding his dick tip between her lips and into her waiting maw. As her lips stretch wide and her cheeks puff out, the Overlord's current Mistress nevertheless does her best to please him, her eyes flicking up to his helmeted gaze again and again to try to gauge his reaction.

Because she can't actually see how he's responding, she doesn't dare stop him when he gets rougher and rougher with her, until ultimately the prim and proper of the two sisters is choking on his dick, tears streaking down her cheeks and saliva and drool getting absolutely everywhere. With Rose being forced to bob up and down the entirety of the Overlord's length as she's face fucked upon his member, Velvet finds herself without much to do, pulling back and watching with a pout as her older sister hogs all the fun.

"Jeez, sister. I didn't know you had it in you..."

Looking up at the Overlord, growing concerned that she might be losing out to her prude of a sister in the one arena where she should be able to smack Rose around and beat her easily, Velvet pouts mightily and reaches out, grabbing one of the Overlord's bared arms and rubbing her substantial, ample chest against it as he chokes her sister on his cock.

"Gagkh! Gagkh! Gagkh!"

"You know, I could deep throat you much better than Rose, my darling black knight! Just give me the chance!"

Not even turning his head in her direction, the silent Overlord seems fully focused on Rose. Despite the ruin that her face was currently in as a result of his violent attentions, when Velvet glances down at her choking, gurgling, gagging older sister, they make eye contact for a moment, and she can SEE the smugness radiating from Rose's gaze back up at her. The red head KNOWS she's winning, despite being in such an unenviable position!

Puffing her cheeks out, Velvet whines and rubs her chest against the Overlord's arm all the harder, her thighs clenching and rubbing together as well as her arousal wets them and drips from her sopping pussy lips. She's ready and raring to go, d-damn it! How dare he ignore her?!

But alas, nothing she manages to do gets his attention. When the Overlord has a goal, he becomes single-mindedly focused it would seem. In this case, his focus is entirely on Rose... and fucking her throat all the way to completion. The only silver lining from Velvet's point of view is that the smugness in her sister's eyes goes away the moment that the Overlord begins to cum, replaced by wide-eyed panic as her cheeks balloon outward like a chipmunk's.

Feeling a bit better as she watches her sister more than struggle with the Overlord's load, Velvet cackles and reaches down, massaging the rest of his seed out of his churning ball sack as she gives Rose a wicked grin.

"That's right you bitch. Drown in it."

Of course, that doesn't actually happen unfortunately. Rose manages to swallow some of it, and while some does explode out of her nostrils and the sides of her mouth, the Overlord is merciful and lets go of her head, letting her pull back as she chokes and hacks and coughs, clearing her airways.Thê source of this content n/o/v/(el)bi((n))

Sneering at her older sister and tired of being sidelined, Velvet does the only thing she can do. She knows she can't get away with trying to physically or even verbally bully the Overlord... but Rose is fair game, right? Pushing her still-recovering sister out of the way, Velvet gets her sexy as fuck body out in front of the Overlord and his big fat cock, still at full mast and still raring for more. Bolstered by that knowledge, the raven-haired seductress eagerly backs her massive booty up into his dick, grinning as she feels him slide between her ass cheeks.

Eagerly letting him hot dog his cock on her, Velvet moans as she looks back over her shoulder at him, on her hands and knees and all his for the taking.

"I get it. You enjoyed her mouth, but obviously only MY cunt is worthwhile. Go on then, my darling. Take me. Make me your woman. Show my sister that she'll never be your TRUE first choice."

Velvet's own words are making her more flushed and flustered as she speaks. She's been waiting for this moment for so long. Sir William was supposed to be the big, strong, strapping lad who took her to bed and fucked her silly night after night. Instead, he turned out to be overcompensating a LOT and his lustful nature had gone so far in the wrong direction that she'd ended up on a huge dry spell, waiting all this time for a proper man to come along and take her.

Now he was here and-

In the midst of Velvet's inner monologuing, she doesn't see the Overlord's hand coming down upon her head until it's too late. As her ass continues to hot dog his massive member, the hulking, scarred man grabs her by her hair... and drives her face down into her sister's quim. Velvet's eyes widen at this, having not even realized that Rose had rolled over from where she'd pushed her sister away and inadvertently lined her pussy up perfectly.

With no other choice in the matter, with the Overlord's desire obvious, Velvet whimpers and begins to do as she's been 'told' so to speak. Even if he didn't make it a verbal order, it wasn't like she had any other options in her current position, now did she? And so, she begins to eat out Rose, giving her cunt quite the tongue lashing as the red head gasps in shock and then moans in wanton pleasure.

"V-Velvet?"

Finally, fully recovering from her face fucking, Rose looks down the length of her own sweat-covered body to see her sister's smoldering eyes glaring up at her while the Overlord holds her to Rose's crotch. Realizing what's happening, an uncharacteristically wicked smile spreads across Rose's face, even as she lets out another groaning moan.

"Ooooh~ Serves you right, you little harlot. Sire has already learned the most important lesson about you... never listen to what you're saying. Mm, your mouth is much better put to use like this~ Oh fuck, sister!"

Velvet scowls but continues to warp her tongue in and out of Rose's quim, until eventually the red head squeals and proceeds to squirt all over Velvet's face. Flustered and embarrassed and a bit humiliated at this point, the raven-haired seductress is quick to scramble up the length of her sister's body the moment that the Overlord finally lets go of her hair.

With the two beautiful, naked, very much prepared women literally atop one another, they both look at the Overlord with pleading expressions. Staring back over her shoulder, Velvet shakes her booty and jiggles her pale, creamy thighs, showing off her glistening wet snatch.

"Please, darling! Give it to me first! I need it! I need your big fat cock inside of me!"

Meanwhile, Rose splays her own legs apart as she's laid out beneath Velvet, offering up her own juicy-looking quim for the Overlord to fuck... if he so chose.

"S-Sire, I'm here to satisfy your every need. My body belongs to you..."

There are a multitude of potential reasons for why he goes with Velvet first, but in the end it matters little. The moment she feels his hands grab harshly at her buttocks, the raven-haired seductress lowers her gaze to her sister and grins victoriously. However, before she can actually say anything or gloat to Rose, the Overlord thrusts forward... and Velvet's victorious expression melts away to be replaced by abject pleasure as she gets her first dicking in FAR too long from the biggest cock of her entire life.

Jaw dropping in sheer disbelief, Velvet's eyes flutter and threaten to roll back in her head right then and there as she moans wantonly. She's not even able to get out any snide remarks to Rose, because she's too busy enjoying herself too damn much. Rose sees this and scowls all the same, upset that she lost out on getting to go first with her Sire.

Not one to be dismissed so easily, Rose slides a hand down betwixt her own legs and begins to play with herself... and then, because she can't exactly get back at the Overlord in any way, she settles for getting back at her intolerable younger sister... by leaning up and capturing one of her swinging tits in her mouth.

Biting down HARD on Velvet's nipple doesn't quite provoke the reaction that Rose was expecting, however. While it does make Velvet cry out... the cry is laced with FAR more pleasure than pain, as she tosses her head back and moans her enjoyment. When Velvet lowers her head again and the two sisters make eye contact, it's like a jolt of electricity runs through them both.

The Overlord is still fucking Velvet and utterly ruining her formerly tight pussy, and Rose is still playing with herself in anticipation of her own turn. However, in that moment it's like almost everything else falls away as they stare into one another's eyes and realize... there was absolutely no reason for them to be enemies.

Even in her current position, one of deep humiliation and a certain degree of discomfort, Jewel is soon enjoying the plowing she's receiving far more than she truly should. While she'd been hoping to pretend, she liked it, while she'd been hoping to convince the Overlord that she could be pliable enough to join his little burgeoning harem... this was just too good. Her wanton moans had a hint of truth to them that they really shouldn't!

"Heh, she's really enjoying herself, isn't she?"

"Hmph, the little pig thief likes getting fucked by Sire. Who could have guessed?"

"Hehe, oh sister, Darling has been such a corrupting influence on you. You've gotten positively catty!"

"If anything, it's from spending time around you, Velvet!"

"Mm, perhaps~"

It doesn't help that the other two women, sisters from the sound of things, are watching the entire while. As the Overlord's huge cock drills into Jewel again and again, driving her absolutely wild, their running commentary is certainly not appreciated. Gritting her teeth, hands clenching into fists, the thief tries to deny the things they're saying about her.

"I-I am n-no pig! And... and it's not even that good! I-I've had better!"

Of course, her words might have been taken more seriously... if not for the throaty moan dripping with arousal that leaves her lips just a beat later. Shuddering, Jewel's eyes flutter up in her head as she experiences her first orgasm impaled on the Overlord's cock. She'd never... she'd never tried to get with the Eighth Hero, back when they'd all been running together as a party.

He'd always felt like the odd man out, and honestly, it'd been so easy to cut him down, to kill him when the time came. They'd beaten the Second Overlord and then killed the Eighth Hero and with that, the world was theirs to do with as they pleased. It was supposed to be their ultimate triumph.

Instead, the whole situation had clearly come back to bite Jewel right in her perfectly round bubble butt. Which is currently jiggling and shaking as the Overlord impacts it with his crotch with every thrust into her tightening, clenching, sopping wet cunny.

Moaning up a storm, struggling in the stocks, trying to break free, trying to escape the pleasure, Jewel begins to realize there might be something worse than torture. The Iron Maiden wasn't preferable to this necessarily, but she didn't like how this was all starting to make her feel. She didn't like feeling like her sanity was being stolen from her. She was the thief, after all! She was the one who was supposed to be stealing things!

Of course, her current assailant cares nothing for her thoughts on the matter. With one final grunt and powerful thrust that drives up against the entrance of her womb itself, the Third Overlord begins to cum, filling Jewel with his creampie, making her shudder, eyes widening and then rolling back in her head from the overwhelming sensation.

Getting filled with his seed had no business feeling that good, d-damn it... and yet... and yet, as she slumps there in the pillory, panting for breath and trying to recover herself, Jewel can't deny how good it did indeed feel. It was... spectacular.

Of course, just as she's starting to shake herself out of the afterglow, just as she's starting to recover from the fuck she just received, the Overlord does something that makes the Ruborian thief tense up and cry out in denial.

"W-Wait! No! Not there, please! Y-You'll break me open!"

He's currently holding her ass cheeks in both hands, and all but promising in his ever-silent manner to butt fuck her. His cock is nudging against her back door and Jewel, in a panic, begs for mercy just as she did when that fucking old ass minion had suggested the Iron Maiden.

"Please! You'll tear me open! You're too big! I'm begging you!"

She's half-expecting him to do it anyways, but to her surprise, the other women speak up in her defense.

"Hm, she might be right, Darling. We could prepare her for you first..."

"As loath as I am to admit it, she could use some lubrication, Sire."

To Jewel's immense relief, the Overlord pulls back, his cock leaving her sphincter alone... for now. Almost immediately, she's once more assaulted by his mistresses instead, their hands all over her body... before she feels something new. There are fingers, but also toys that are beginning to press against her holes. One toy starts at her cunt, sliding into her and gathering up quite a bit of lubricant from her messed up pussy, only to slide up between her ass cheeks.

Jewel trembles and whimpers, even as the toy, much smaller than the Overlord's cock, begins to penetrate her anally.

"Not to worry, pet... we'll get you prepared for Darling."

"That's right. By the time we're done with you, you'll be begging for Sire to bugger you."

Just like they begged him to breed them? Jewel shudders at the realization that she might get pregnant from this whole humiliating encounter. On the one hand, it was kind of like she'd stolen a baby, if one did come about, right? Except... she had no desire to have a child, no desire to be a mother. She didn't... she didn't want this. She would never beg!

Only... the more they toy with her, the more Jewel finds herself at wit's end. It's impossible to escape their touch of course, impossible to escape their toys. Slowly but surely, the two pregnant mistresses of the Overlord work open her backdoor with their toys, while also continuing to play with her cunt, clit, and nipples all at the same time.

They work ceaselessly and tirelessly, and all Jewel can do is try and hold back her moans, try and restrain her body's responses to their endless attacks on her mind. For that is what it is. Pleasure it might be, but it is also an assault on her senses. And... it's hard to remember how scared she was of the Overlord fucking her in the ass, when their toys are now stretching her anus wider and wider and making the experience more and more pleasurable.

The worst part is, the two women seem to know her body all too well, perhaps better than the Overlord would because Jewel the Thief doesn't manage to cum once under their attentions as time passes by. Oh, she certainly wants to. It feels good, don't get her wrong, and more than a few times she feels herself on the cusp of a release. And yet... the raven-haired one, Velvet... she always seems to know.

Not only does she stop her own actions whenever Jewel is getting close to orgasming, but she stops her sister Rose as well. And then, as time goes on, as they continue to tease her, to torture her, Rose starts to learn to notice the signs as well and doesn't even need Velvet to tell her anymore.

It is indeed torture, just of a different sort than what Jewel feared. A consummate coward, the Ruborian thief had feared pain and agony, had been afraid of being tortured in a more conventional way. Now though, she's starting to learn that pleasure can be a source of torture too... especially the withholding of pleasure.

The more they play with her, the more Jewel loses track of just about everything. It feels like DAYS have gone by, though to be fair her sense of time has been fucked ever since she was thrown into the dank dark dungeons of the Overlord. Still, it's been a long time, she's sure of it. How the two women keep going, she doesn't know. How are they still on their feet? She's exhausted, but they just keep on going.

She needs to cum. She wants to cum so badly. But as it is... they refuse to let her cum, even when she starts to beg for it.

"Please... please, please, please..."

"You know what we want from you, thief. If you want to beg, beg Sire to fuck you in the ass. It's the only way you're getting anything more."

"That's right. Darling is waiting... just give in."

The Overlord was still there? Jewel could hardly believe it. Surely, he would have left to do something more important by now. It must have been days... right? In truth, it'd barely been an hour. Jewel was greatly overestimating herself.

As it is, in that moment, the Ruborian thief breaks anyways... and begs.

"Please... please fuck my ass! I don't care if you bugger my anus... just let me cum!"

A moment later, and his big masculine hands are back on her ass cheeks, gripping them harshly as he proceeds to thrust forward, burying his cock in her ass right then and there. Thanks to Velvet and Rose's preparations, she's loose and wet enough for him, while still being very, very tight back there. For Jewel, having his dick finally in her ass... it's a euphoric sensation akin to a religious experience.

Eyes rolling back in her head, tears streaking down her cheeks, Jewel lets out a keening wail as more and more of her mind shatters, the thief vanishing and being replaced by a whorish slave to her new master, the Overlord.

Seemingly sensing this, Velvet lets her out of the stocks and the Overlord lifts her up into the air. As Jewel drops down onto his cock even further, his massive member punching up into her gut, the dark-skinned woman cries out and creams herself on the spot, orgasming explosively.

"Yes, Master! Fuck me harder, Master!"

Meanwhile, Rose grabs her by her hair and pulls her into a kiss, silencing her squealing begging and Velvet bends over to begin eating out her sopping, messy cunt.

The two pregnant women welcome a new member into their fold... though of course, both know that Jewel will never be equal to them. She is nothing more than a slave, while they are their Overlord's mistresses, his concubines. Still, the Third Overlord is insatiable... so they're both all too happy to have a third woman to take some of the load off...

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A couple months later, up in the Overlord's Throne room, girlish squeals and squeaks can be heard echoing through the chamber. As Velvet and Rose nurse their newborn babes to their chests, Jewel the Thief bounces up and down on their Overlord's cock, getting fucked anally with a small baby bump of her own visible by this point.

As he cums in her ass and she falls forward face first onto the floor, the Overlord relaxes on his throne, and Rose and Velvet both hurry over to join him. The large arms of his massive throne allow them more than enough space to sit at his sides, even as they lean in close to bask happily in his presence while continuing to nurse their babies.

Meanwhile, Jewel slowly crawls over to a large cushioned pillow next to the throne, kneeling there and running her hands up and down her body, the Ruborian thief completely broken in by this point, and having settled fully into her new role and life as a sex slave to her Master. She belongs at his feet, just as his Mistresses belong at his sides. She should have known there would be consequences for betraying the Eighth Hero as they had.

After all, Evil always finds a way.

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