The Harem King (High School DxD) (Patreon)

Poll Winner

Themes: Foursome, Slutty Sex, Mind Break, NTR

Summary: After Riser is defeated and the engagement between him and Rias broken, Venelana and Grayfia decide to visit the man that has so captured the interest of their Rias. Unbeknownst to them, Issei’s increasing powers, dominating nature, and insatiable desire to be the harem king makes him increasingly irresistible to even the most strong-willed females, leading to a fundamental change in their lives forever. 

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“Issei, I’m back! And I-mmph!”

Grayfia Lucifuge and Venelana Gremory exchange a glance as they step into the room behind Rias. The Gremory Heiress had been about to introduce the two of them, when Issei had all but sprung at her, gathering her up into a VERY intimate hug and kissing her soundly as his hands fondled her ass. For her part, the red head doesn’t even try to fight it. She stiffens for all of a moment, no doubt because of their audience, but then seems to forget all about her mother and her brother’s wife, melting into Issei’s chest and letting him kiss her passionately.

When things start to get a little TOO raunchy, meaning one of Issei’s hands comes up off of Rias’ ass and snakes around to grab and squeeze at one of her tits, Grayfia and Venelana both step forward and open their mouths to speak at once… only for those mouths to also click shut at once, as the full presence of Issei’s demonic aura hits the two exceptionally powerful older devils right across the face.

In the middle of the Rating Game against Riser, it hadn’t been overly apparent, though there had been some hints here and there that Issei Hyoudou was more than he seemed. For one, though he’d gotten knocked down once or twice, he kept getting back up, no matter what. For two, all of his opponents, Riser’s own peerage of beautiful babes at that, had been blushing like mad and even in some cases rubbing their thighs together when Issei took each and every one of them out of the fight.

In the end, Issei’s defeat of Riser in a grand finale one on one bout of combat had caused something of an uproar. How could a Reincarnated Devil, even one rumored to be the new wielder for the Boosted Gear, possibly be so much stronger than a Pureblood Devil of the same age? In the aftermath, Grayfia and Venelana had decided to take it upon themselves to scout out Rias’ newest peerage member and better advise Rias on to what she should do next.

As such, this meeting had been arranged. But now… now, Grayfia and Venelana were struck speechless. The powerful maid and Gremory Matriarch found themselves blushing slightly, and even unconsciously rubbing their thighs together, as Issei’s incredible power washed over them. Unbeknownst to them, his dominating nature and insatiable desire to be a harem king had… comingled, so to speak. He was becoming rather irresistible, even to women like them.

Finally, he and Rias have to pull back for air, and in doing so, Rias is reminded that her mother and Grayfia are there in the first place. Blushing profusely while already flushed and panting and mewling since Issei’s hands are still on her body, Rias wiggles about in his grasp for a moment before giving it up for a lost cause.

“I-Issei. I had two people I wanted to introduce to you! T-This is my mother, Lady Venelana Gremory… a-and you, oooh, already know G-Grayfia!”

When the brown-haired young man turns his eyes upon them, both Grayfia and Venelana freeze in place. Those eyes… they reminded the two women of the handful of times in their lives when they’d each seen Sirzechs Lucifer truly angry. Except… except this was even worse than the anger of a Great Satan, somehow.

“That’s right. You two spat on Rias’ happiness, didn’t you? You didn’t mind seeing her cry, so long as she married that chicken shit Riser.”

Neither Venelana nor Grayfia can find the words to defend themselves. To say this encounter had been turned around on them near-instantly would NOT be an incorrect statement. Luckily, Rias quickly pats Issei’s chest.

“I-Issei! It’s not like that. My mom and Grayfia… they didn’t really have a say in the engagement to Riser. That was our dads…”

Not quite true. After all, Venelana might have been able to fight harder for Rias. Grayfia, meanwhile, had directly stopped Rias from letting Issei sully her, which had been what led into the Rating Game in the first place. They’d both played their parts, but it WAS easier to blame it on the men, Lords Gremory and Phenex, and just say it was all their fault.

And… stunningly enough, it seemingly worked. Issei’s attitude changes in a second, his mood swinging on a dime as he beams instead of glaring angrily.

“Oh, alright! Rias… did you bring these two here to fulfill your promise to me?”

Rias’ blush grows even redder, if that’s possible, and she ducks her head in embarrassment. Finally finding her voice, Venelana Gremory clears her throat.

“W-What… promise?”

It’s been a long time since the Lady Gremory stammered through saying ANYTHING. Normally unflappable, gentle, and composed in all things, she’s having a harder and harder time not jumping Issei’s bones right then and there. She just… she just wants to get down on her knees and suck his cock. Judging by Grayfia’s squirming next to her, the silver-haired maid feels the same way.

Issei, grinning, nods resolutely.

“Rias promised that if I won the Rating Game for her, I could have all the oppai I want!”

Seeing how his hand is still squeezing one of Rias’ ‘oppai’ even now, that certainly doesn’t seem to be inaccurate. And indeed, Rias doesn’t try to deny it. She just moans under Issei’s casual groping touch. His confidence and sheer charisma wash over all three women, and neither Venelana nor Grayfia can bring themselves to deny it either. After all, shouldn’t it be Rias to pipe up and explain this is all a misunderstanding? But… she doesn’t.

“Well? Show em to me!”

Issei certainly seems like an affable, cheerful boy… on the surface. But his power fills every inch of the room, and the two older devils, for all that they’re some of the strongest women in the underworld, can’t stop themselves. Slowly, shaking not with fear but arousal, Venelana Gremory and Grayfia Lucifuge reach up and divest themselves of their tops, pulling their dresses down and letting their massive chests bounce free.

Issei’s eyes immediately zero in on them, and the lustful growl he lets out nearly sends all three female devils right to their knees. As it is, they ALL squirt a little, experiencing micro-orgasms as he steps up to Venelana and Grayfia with Rias still curled into his side.

One would think three pairs of tits would be too much for one man to handle. One would thus not really know Issei Hyoudou very well. Despite only having two hands and one mouth, Issei is all over these new sets of oppai in mere seconds, while continuing to pay Rias plenty of attention as well. He goes to town on Grayfia and Venelana’s titties, and also makes sure Rias’ nipples are rock hard and poking out from her chest, standing proud.

Venelana and Grayfia can scarcely believe what’s happening… but both women know they don’t want it to stop. And when Issei finally takes out his cock… it’s so very simple for them to drop to their knees. He slaps his dick across their faces a few times apiece, before nodding approvingly.

“Alright… I’ll believe that you two didn’t have anything to do with Rias’ engagement to that chicken shit. You seem like good girls to me. And I like your oppai!”

Issei Hyoudou, for all his power… is an exceedingly simple man. Realizing that in that moment, both Grayfia and Venelana come to the same conclusion independent of one another.

“Please fuck me, sir!”

“I need you inside of me, Issei!”

They immediately glare at each other, acting less like themselves and more like a pair of wanton devil sluts. Issei blinks, and then grins wolfishly, while Rias blushes in second-hand embarrassment.

“Sure! I can do that! Assume the positions!”

Immediately, Grayfia flips over onto her front, doggystyle, and flips up the back of her maid skirt, pulling down her panties. Venelana, meanwhile, hikes up her dress and yanks her panties off as well, but goes down onto her back, splaying her legs apart and spreading her pussy lips with her fingers invitingly as she cups a breast and moans wantonly.

Obviously, both women have very different definitions of ‘assume the position’, but that’s fine by Issei. Without skipping a beat, he drops down to his knees… between Venelana’s legs. Call it what you will. Maybe he’s more enticed by her still on-display rack, compared to Grayfia’s jutting ass. Maybe he’s still upset at Grayfia for stopping him and Rias from going all the way that first time he met the maid.

It could be any number of things. The end result is the same though. Issei takes his massive member and lays it upon Venelana’s abdomen for a moment, making the normally composed and softspoken Lady Gremory squeal in an embarrassing fashion.

“Y-You’re gonna turn me into a living onahole with that thing, I-Issei!”

Snickering, Issei just shrugs as he slowly slides his cock back, until its pressing against her entrance. At the same time, his fingers are thrusting into Grayfia Lucifuge on one side… and Rias Gremory on the other. The young red head, loath to be left out, has moved into position as well and offered up her pussy to Issei.

Glancing at her as he thrusts into her mom, making Venelana squeal and shudder in orgasmic ecstasy, Issei’s eyes glitter.

“I guess you’re not the only Gremory who likes hentai, huh Rias?”

The Gremory Heiress just shakes her head, embarrassed on both her and her mother’s behalf. Of course, it’s far too late to salvage any of Venelana’s dignity. Issei slams in and out of the Lady Gremory hard and fast. No one says it, but there’s no denying what he’s doing… he’s fucking another man’s wife silly, right then and there. He’s fingering a second man’s wife at the same time, too.

Grayfia and Venelana couldn’t care less about their respective husbands at the moment, however. Here was the one devil who had managed to help Rias out of her predicament. And he was so unbelievably powerful, handsome, and with the biggest cock either of them had ever seen. Having taken complete leave of their mutual senses, the powerful older women cry out, the two MILFs shaking and shuddering under the combined onslaught of Issei’s cock and fingers.

Venelana definitely gets more from his cock than Grayfia gets of his fingers though, and soon enough the flaxen-haired beauty’s eyes are fully rolled back in her head, her tongue lolling pointedly out of her mouth. She looks rather silly like that, but then, she had pretty much said it straight up. Issei has turned her into his tight little living onahole, her tits bouncing up and down all over the place as she cums again and again upon his cock.

By the time he finishes inside of her, Venelana is insensate, in a pleasure coma, and likely not going to be coherent any time soon. Which means it’s time for Grayfia. The maid whimpers, as Issei moves over behind her kneeling form and digs his hands into her ass cheeks.

“I-I apologize for interfering, m-my Lord. I should, a-ah, never have gotten between, oooh, you and Rias.”

Completely unbidden, the apology makes Issei cock his head to the side… and then nod approvingly. His cock slides up and down her slit for a few moments, before he slowly sinks into Grayfia’s depths, much slower than he first penetrated Venelana. The powerful maid cries out, whimpering all the same as he stretches her, inch by inch.

Only once he’s fully hilted inside of her does Issei stop and reach forward, wrapping his arms around her and grabbing her tits hard.

“I forgive you, Grayfia. Let’s be friends from now on!”

Then he starts to fuck her, juxtaposing his sunny attitude and seemingly cheerful words with the most powerful plowing that Grayfia Lucifuge has ever experienced. Tears streaming down her cheeks, tongue sticking straight out of her mouth, eyes crossed, Grayfia squeals and shakes and shudders through orgasm after orgasm.

“Y-Yesh! Let’sh be best frieeeeeendsh!”

Her tongue wagging all over the place slurs her words, but Issei doesn’t seem to mind, just grinning and fucking her even harder. She ends up much the same way as Venelana in no time at all, his immense cock size combined with his domineering nature and his incredible power sending her into a state of euphoria from which returning would certainly be a chore and a half.

But that’s alright, because Issei has a third woman to fuck. Rias ends up taken on her back, same as her mother. Unlike Venelana however, Issei only puts one hand on her tits. The other hand intertwines with one of Rias’, their fingers locking together as he thrusts into the red head again and again. She might be younger, she might not be as strong or quite as voluptuous as Grayfia or Venelana, but Rias has one thing over the older pair of devils that they will never have. She was Issei’s first.

As he fucks her hard and fast all the same, Rias moans into Issei’s mouth, her legs high in the air, half-wrapped around his waist and half bouncing back and forth over his back. Her pussy walls clench and squeeze down along his cock, and her entire body shudders and quivers its way through orgasm after orgasm as he fucks her senseless.

It wasn’t like this, at the start. When Rias initially saved Issei, he wasn’t this way. But then, Riser had shown up and it was like night and day. More than that, Issei had unlocked his Sacred Gear, which was far more than even Rias bargained for. Not that she was complaining. Having the Red Dragon Emperor by her side, as her lover, was more than the red head ever could have hoped for. He’d saved her from a fate as Riser’s bride, saved her and the female members of her peerage from having to submit to that bastard.

In comparison to that… was giving over her mother and her brother’s wife to him really that much to ask? Yes, Rias hadn’t just stayed quiet because she didn’t know what to say. Venelana and Grayfia might have thought otherwise, but it was true. Issei had been right on the money when he’d asked if they were only there to fulfill Rias’ promise of ‘all the oppai that Issei could desire’ to him.

Her big-dicked, domineering lover wanted to be a harem king. And so, Rias would help him do it… no matter who she had to feed to his overwhelming libido and ever-insatiable lust for more and more women.

With a groan, Issei spends himself a third time inside of Rias, creampieing her just like he did Grayfia and Venelana. Squealing, eyes rolled back in her head, Rias lets herself enter the same state of ahegao as those two older devils at last, knowing that she can trust in Issei to look after them all… even if he probably will end up fucking their insensate bodies some more to calm his ever-raging libido.