The Sleeping Dragon (High School DxD)

A/N: Here's the new Chapter! Which also means the next four chapters are up on my Patreon for early access as well as the chance to vote on the direction of the story!

Grayfia has a surprise for Issei involving her fellow Queens~

-x-X-x-

“What’s all this then?”

Issei’s tone is one of amusement as he steps into his study to find three very beautiful female devils all lined up along one wall, wearing matching skimpy maid uniforms and standing at attention as they await him. The first and eldest of the three women steps forward then, her silver hair almost shimmering in the artificial light.

Grayfia Lucifuge bows at the waist to him before straightening back up and blushing at his affectionate gaze.

“Do you recall the last time we spoke, sir?”

Issei hums in thought before waving a hand through the air.

“Let’s pretend I do.”

Of course he did, but he and Grayfia had a certain… relationship to be maintained. One where he teased and bullied her and she took it like the servant she was. All because secretly, at heart, she loved it. She loved being dominated by him in so many different ways.

Flushing a bit at his indifferent sounding words, Grayfia swallows thickly. Clearly she’s nervous about whatever this is… but then she might have reason to be nervous if she thinks she’s overstepped.

“You t-told me that I was your… head maid. But I am also your only maid, Master Hyoudou. As s-such… I took the liberty of procuring two more maids for your staff, to serve you faithfully and dutifully… in all ways.”

Issei hums in amusement at that, before finally sliding his gaze over to the two other devils in the room. Akeno Himejima and Tsubaki Shinra. Rias Gremory’s and Sona Sitri’s Queens, respectively. To Grayfia’s credit, neither looks exactly unhappy to be here. Both have borne Issei children at this point, making their positions in his hoard and harem more than secure. Grayfia has done the same, as a matter of fact.

However, Issei is a very busy man these days, and with a massive amount of women all clamoring for his attention to boot. He might have taken God’s place, but even after years on the Throne of Heaven, he’s not omniscient or omnipresent. Not yet, anyways. As such, he’s not at all surprised that Akeno and Tsubaki are going along with this, effectively piggybacking off of Grayfia’s time with him. They’re feeding off of her as much as she’s in turn using them.

There’s just one small problem with all of this. Issei hadn’t named Grayfia his ‘head maid’. He’d simply told the silver-haired maid that she gave the best head during a moment in which she’d been on her knees, sucking his cock.

Heh, ‘taking liberties’ indeed. For a long moment, Issei considers how he wants to handle the situation. Does he humiliate Grayfia by outing her for her lies? Or does he go along with it because… well, three sexy maids stand before him, all waiting for the Master of the House to enjoy their delectable bodies. Honestly, in the end… it’s no contest.

“Very good, Head Maid. Now then… I assume you’ll be leading by example, yes?”

Flushing further, Grayfia hurriedly nods before turning to Akeno and Tsubaki. The two younger Queens both stiffen under the intense gaze she gives them as she leaks just a little bit of killing intent in the process.

“You two. Get to work. Clean this study until I tell you to stop and by the time I do, it better be spotless. You WILL be graded on your work… and the best of the two of you can likely expect a reward from our Master. The worst should only expect a punishment from me.”

Akeno and Tsubaki don’t need to be told twice. The two female devils spring into action, getting to work right there on the spot. As does Grayfia. Though there’s a big difference between their work and her work. Indeed, the silver-haired maid drops to her knees right in front of Issei and pops her tits out of her skimpy top without hesitation.

She then proceeds to unbutton and unzip his pants and pulls out his cock, before wrapping her tits around his dick and leaning forward to take the bulbous tip of his massive member in between her lips. When he reaches out and grabs her by braids, Grayfia doesn’t protest in any way. Smirking, Issei gives her braids a tug, guiding her mouth up and down the first few inches of his cock while her soft, supple breasts slide along the rest of his length.

He has to admit, his Head Maid has excellent technique. Her tongue swirls this way and that and she keeps her eyes on his face at all times, reading the most minute of expressions in order to adjust and adapt her actions to best pleasure him. Issei had been in the throes of lust and ecstasy when he’d told her she gave the best head out of everyone in his hoard, but there was still some truth to the claim.

Would she come out on top as the Champion in a full-blown blowjob tournament featuring his entire harem? Maybe, maybe not. But would she place in the finalists? That Issei would bet money on without a doubt.

That said, even as Grayfia is giving him an expert titjob-blowjob combo and Issei is tugging on her braids, he’s also watching Akeno and Tsubaki’s progress. The two younger Queens are all over the study, which admittedly doesn’t see much use from Issei himself. As such, there is in fact a layer of dust on almost every surface, giving them plenty of work to do.

However, there’s definitely a difference in… technique between Akeno and Tsubaki. Namely, Tsubaki is actually focused on cleaning above all else, while Akeno is busy posing and showing off for him. The S&M Queen makes sure to thrust out her tits in his direction whenever she catches him looking and ‘accidentally’ drops her duster more than once so she has to bend over and flash her bare naked pussy at him in the process.

Issei enjoys the event for what it is… dinner and a show. But eventually, Grayfia does manage to drain his first load from him. The silver-haired maid moans as she sucks down his seed, drinking every last drop of his cum without spilling a single drop just like the professional maid she is. Smiling down at the Underworld’s Strongest Queen, Issei watches as she swallows and swallows until finally… there’s nothing left.

For the time being, anyways. Obviously Issei is more than ready to go again. Letting go of her braids, he lets her decide how this is going to proceed however, curious to see where she takes things. Rising from her knees rather gracefully in spite of just swallowing an entire load of cum, Issei’s self-proclaimed head maid claps her hands twice. Akeno and Tsubaki both stop what they’re doing and zoom over to stand in front of the two of them, heads bowed and hands clasped behind their backs.

“Master Hyoudou. What do you think of your two new maids. Did either of them stand out to you in any way?”

Issei hums as Akeno and Tsubaki shoot him glances, both trying to get his attention now. It’s a little belated on Tsubaki’s part, but she’s definitely pushing out her chest as best she can and biting her lower lip in hopes that he’ll point her out. But…

“Actually, they both did… each in their own ways. I’ll be honest… I don’t know which to choose. So I’ll leave it up to you, Grayfia. As my Head Maid, you should be able to make these kind of decisions after all.”

Even Grayfia is surprised by that, though she quickly recovers with a beaming smile, looking like he’s just said Christmas has come early.

“Of course, sir! Both of you! Turn around and bend over the Master’s desk!”

As her fellow Queens hasten to obey, Grayfia steps forward and with one smooth motion, flips up both Tsubaki and Akeno’s skirts. Neither are wearing panties, which is unsurprising all things considered. However… while Tsubaki is wet, Akeno is sopping. More than sopping, she’s leaking. When Grayfia brings her palms down on both women from behind, spanking their pussies, the two other Queens squeal… but the sound from Akeno’s cunt is much, MUCH wetter.

“One of you proved yourself a worthy maid to our Master today. The other… has proven they need remedial training. I think you both know what I’m going to say. Tsubaki… you focused on the task I gave you above all else. Akeno, you focused on presenting yourself as eye candy to our Master above all else.”

The two women squirm, blushing profusely at this. But Grayfia is just getting started.

“Technically… neither of you were wrong. And in the end, Akeno cleaned up almost as much as Tsubaki. The difference was negligible in the end. However, there was one way in which Akeno failed as a maid to Master Hyoudou.”

Akeno squawks at that, but Grayfia has already grabbed her fellow Queen by the base of her ponytail and spun her around, forcing her to look back across the study… to the small trail of near-invisible droplets of pussy juices that Akeno had been dripping behind her for quite some time.

“In the end… it wasn’t prioritizing our Master’s pleasure that made you a failure, Akeno Himejima. It was prioritizing your own and thus leaving more of a mess than you cleaned up. As a maid… that is unacceptable behavior. Do you understand?”

“… Yes.”

SMACK!

“Yes, what?”

“Y-Yes Head Maid!”

Nodding her head, Grayfia looks to Issei and then to Tsubaki.

“It is my opinion as Head Maid, Master Hyoudou… that Tsubaki deserves to be rewarded for her diligent work.”

Issei just grins. He absolutely loved the show. Now it was time for dinner. With no real preference one way or the other, he just shrugs and steps up behind Tsubaki. Sona’s Queen whimpers as she hastily pushes her glasses up the bridge of her nose, still stood with her hands flush on his desk and her bared ass thrust out in his direction. Bent over and in position for him already, all Issei has to do is grab her by her hips and slide right on inside.

Her arousal might not have been enough to leave a mess like Akeno’s did, but she’s still quite wet as he thrusts forward into her. Moaning up a storm, Tsubaki immediately goes up on her tiptoes to accommodate him, and then thrusts her hips back into his cock a moment later. Grinning, Issei begins fucking the bespectacled maid hard and fast, pounding her pussy deeply as she cries out and shudders her way through orgasm after orgasm.

Of course, her orgasms quickly grow powerful enough that she’s squirting all over the place, specifically making a mess of the front of his desk and the floor between her shuddering legs. However, Grayfia doesn’t call her out on it… perhaps because it’s a mess that’s made by ‘Master Hyoudou’ in the end. Or perhaps simply because she’s busy still… with Akeno’s punishment.

Glancing over as he continues to rail Tsubaki from behind, Issei raises an eyebrow at what Grayfia is doing to Akeno. The Head Maid has Rias’ Queen on her hands and knees and is forcing her to lick up every droplet of pussy juices that she leaked onto the floor of his study. At the same time, she’s got a paddle in her hand and is spanking Akeno’s ass with it.

Fortunately for the beleaguered younger devil, Grayfia has seen fit to cover up Akeno’s cunt with a magical seal, making it so she can’t make any further of a mess at this point. Of course, that also means Issei won’t be able to fuck the raven-haired woman there when the time comes. Amused but still enjoying just going with the flow, Issei returns his attention to Tsubaki.

It was a long, long time ago that he’d first fucked the bespectacled woman. She’d leaned into her Shinto Heritage and dressed as a Shrine Maiden, calling him a lustful spirit and claiming she was going to purify him. Needless to say, that had ultimately just been a ploy to get fucked by him, an unspoken offer that Issei had happily taken Tsubaki up on. He’d fucked her silly and she’d enjoyed every last moment of their ensuing relationship just as she was enjoying their time together now.

Plowing Tsubaki, pounding her pussy from behind… Issei nods and then proceeds to give her a big, filling creampie. He pumps a hot, thick load into the bespectacled Queen’s womb, feeling as she climaxes around his cock from that. He can tell she loves the idea of getting pregnant off of him again. She likes being a mother… but she likes being knocked up by him even more.

Pulling out of Tsubaki to let her rest, Issei turns and grins, not in the least bit surprised when he sees what Grayfia is doing with Akeno now. Having finished forcing her to lick up her own mess, the Head Maid has suspended Akeno midair in rope bondage and is continuing to paddle her body in different incredibly sensitive places.

She stops as he approaches though, but only for a moment because Issei just waves her on.

“Oh, don’t stop her punishment on my account, Grayfia. In fact… I can see there’s only one hole available. But that’s just fine by me.

“Mmph? Mmm!”

Grinning, Issei slips into place behind Akeno’s dangling body. With her pussy magically sealed, that leaves only one option. Oh sure, he could have broken Grayfia’s magical seal with ease… but where would the fun in that be? Instead, he grabs Akeno by her thighs and proceeds to impale her ass upon his cock, making the gorgeous sadomasochistic Queen squeal loudly through the gag that Grayfia has fit into her mouth.

Grayfia only hesitates for a moment before continuing to paddle Akeno’s tits and abdomen, all while Issei fucks the poor woman’s ass. Not that there should be any pity for Akeno Himejima. For all her pained squealing and big puppy dog eyes, Issei knows the truth. She loves this. She loves to be humiliated, degraded, and dominated by those stronger than her.

Rias’ Queen has always been a freak, even all the way back at the beginning. And not even motherhood has changed her in that regard. Oh, don’t get him wrong, Akeno is still a great mom. But when the children are away, the adults will play… and nobody plays harder than Akeno Himejima.

With that in mind, Issei doesn’t have any regrets about fucking and creampieing the gorgeous devil’s ass instead of her cunt. She’ll have more opportunities to ‘earn’ another pregnancy at the end of his cock. For now… for now she’s ‘failed’ to meet Grayfia Lucifuge’s expectations and as his Head Maid, it was up to Grayfia who was punished and who was rewarded.

Funny how both punishment and reward were sex in the end. But then, Issei found himself reflecting as Grayfia got down on her knees again and once more took him in her mouth… he was pretty sure none of them would have it any other way.

[X] The Exorcists (Irina, Xenovia, Griselda, Asia) - 36%