The Sleeping Dragon (High School DxD)

Issei hums, considering Sister Griselda on her knees before him, being choked on his cock by an overenthusiastic Asia Argento. At the same time, he considers Xenovia’s question, the blue-haired girl sounding eager for him to give her superior the same treatment he gave her and Irina… that is, a womb full of his seed and the intrinsic promise of being knocked up, one way or another.
 
Cocking his head to the side, he looks down into Griselda’s eyes and delivers his verdict.
 
“… No.”
 
Asia, Xenovia, and Irina all react with differing levels of disappointment, with Xenovia whining, Irina frowning, and Asia pouting mightily. But its Griselda that Issei is paying attention to right now, and its Griselda’s reaction that he watches closely, noting the flicker of discontentment in her eyes, even as Asia continues to feed her his cock, pushing her head down his length again and again.
 
Grinning, Issei shrugs his shoulders.
 
“Not unless she gets down on her hands and knees, bows that haughty head of hers, and begs me for it, of course.”
 
Another round of reactions from the girls surrounding him, but once again, Griselda’s reaction is the only one Issei is paying any attention to. The older woman’s eyes widen in surprise at his words, before filling with outrage. But Issei can tell that outrage is only designed to cover up her true feelings on the matter.
 
Of course, when Griselda suddenly begins to fight back against Asia, the younger woman is in no position to truly hold her down. Sister Griselda is a warrior, and Asia… is just Asia. And so, she has to step back, letting Griselda push off of his cock with a pop as his dick tip leaves her parted lips, a strand of saliva connecting them for a moment before it breaks.
 
“You… y-you can’t be serious.”
 
Issei raises an eyebrow at Griselda, chuckling softly as he cocks his head to the side again.
 
“Can’t I? Because I assure you, Sister… I’m very serious. And I can tell just how aroused the idea makes you, so I’m not sure why you’re acting like it’s so far-fetched.”
 
Sister Griselda trembles, making her huge, naked breasts shudder and quiver along with her as she narrows her eyes at him. Bringing a hand up and placing it on her chest, she snarls.
 
“I am more than my baser instincts, Red Dragon Emperor. I am not so weak willed that I cannot resist my own temptations!”
 
And then, a considering gleam shows up in her eyes and she thrusts out her chin, sniffing haughtily.
 
“But can you? I wonder. You ask me to beg, but you’ve already beaten me. I’m yours to claim as you will. If I do not beg, what shall you do? Cease to have your way with me? Good. It will only make things easier on me.”
 
Heh, bravado to say the least. Griselda wants it and she wants it bad. If Issei denies her, then she’ll only suffer as she’s forced to watch him have his way with her charges and Asia instead. But no, that won’t be necessary. There’s a middle ground here. With a shrug, Issei smiles.
 
“I’ll just fuck your ass instead then.”
 
Griselda stiffens at that, looking distinctly embarrassed.
 
“T-That is… u-unclean.”
 
Xenovia is the first to pick up on it and being the newly minted conniving little minx that she’s become, she doesn’t hesitate.
 
“Is that a note of desire I detect in your voice, ma’am? I will admit, I’m new to these sorts of things, but you sounded almost… aroused by the thought of Issei fucking your ass.”
 
Having not been expecting such an accusation from the girl who might be her biological daughter (Issei hadn’t confirmed yet, but he was pretty sure he was right about that) Griselda sputters in disbelief, eyes wide in shock at being called out so casually. Giggling, Asia nods.
 
“I think you might be right, Xenovia. I think Sister Griselda does want Issei’s big fat cock up inside of her bum~”
 
Griselda scowls at Asia for that, glaring with some real heat as she shakes her head.
 
“O-Of course the corrupted Holy Woman would say s-such things… just how long have you been in this perverted dragon’s clutches, hm?”
 

Asia just giggles and shakes her head.
 
“Its not about how long. He’s only had his hands on Xenovia and Irina for a little while and look at them. He’s only had you for an hour and look at you.”
 
As far as retorts went, it was a good one. Griselda flushes and averts her gaze, until Issei reaches out and tucks two fingers under her chin, forcing her to look up at him again. His cock, still rock hard, throbbing with need, and glistening with her saliva, swings back and forth in front of her face.
 
“So? What will it be? Beg to be bred, or anal until you beg? Because really… I’m not going to make you a mother if you don’t want it.”
 
Griselda squirms, and it’s clear that parts of her are warring with other parts of her. Clearly, she wants it all… she just doesn’t want to admit it, nor does she think she should let herself have it all. Issei can tell, if she was fully uninhibited, she would beg him to fuck her ass and THEN fuck her pussy, and that would be the end of it. But ultimately, Griselda is much older than most of the girls he’s claimed so far. She comes with a lot more baggage.
 
“… please, breed me…”
 
He hears her quite clearly, but of course, he’s not just going to let her murmur it under her breath like that.
 
“Hm? What was that.”
 
“I-I said… I would like you t-to breed me.”
 
Grinning now, Issei shakes his head.
 
“Is that how you beg? Didn’t I say on your hands and knees?”
 
Griselda glares up at him for a moment or tries to. In the end, there’s no heat left in her glare, and her blush is intense as she ultimately lowers her gaze. The shapely, mature woman, a Grade A MILF if Issei has ever seen one, slowly lowers herself down into the position of prostration that he’s demanding of her. Placing her hands palm down on the ground and her forehead between them, she nevertheless speaks clearly and concisely this time around, even as her hips rise high into the air enticingly, her ass as well as her pussy lips no doubt on display, if he were to circle around her.
 
“Please, Red Dragon Emperor. P-Please convey your seed upon this w-worthless exorcist, so that she may c-carry your child, and give birth to a s-strong baby b-boy or girl…”
 
Issei’s cock THROBS… and so he doesn’t waste any time, now that he’s gotten what he wanted. Xenovia and Irina, meanwhile, are staring at Griselda with wide eyes and mouths agape, their own faces bright red and their eyes glazed over with arousal at the sight of their superior in such a state. Asia, meanwhile, is just smiling a perverse, knowing smile, pleased as all punch to see Griselda submitting so utterly.
 
Moving behind her, Issei takes the already half-pulled down section of her exorcist uniform and keeps pulling, until it’s bunched around her knees, exposing her shapely backside, broad hips, and glistening wet cunny, down betwixt her thighs. Grabbing Griselda by her ass, Issei considers spreading her cheeks and treating her to some anal anyways, just to make her admit she was an anal slut deep down inside too.
 
But no, he’s proud of her for at least acknowledging she wants to be bred, and so when he brings his cock to bear against her, its against her pussy lips, pressing the tip of his thick, throbbing dick against her slit and giving her all of one moment before he thrusts in.
 
It takes some of Issei’s considerable willpower and strength to avoid cumming on the spot, he quickly finds. There’s something to his usual modus operandi, which is to go ahead and cum once before even getting to this point, usually all over a girl’s face, or down her throat. But he hadn’t done that this time, because Griselda had pulled off to act all indignant with him when he’d said she would need to beg for him to breed her.
 
Well, if nothing else, Issei is certainly a bit rougher with the MILF exorcist as he fucks her from behind in the downward doggy position. Gasps and moans leave Griselda’s throat, and she shudders as she arches his back for him, but none of that makes Issei show her any mercy. No sir, he fucks her hard and he fucks her fast, gritting his teeth and gripping her ass cheeks harshly with his hands. Digging his digits into her toned, athletic derriere, Issei plunges deeper and deeper into her cunt, until finally he’s slamming up against her cervix directly.
 
Ah, but she wants him to breed her. She’s begged for it. So Issei doesn’t let up even there. Even as his vision swims a little bit, not from being remotely tired but from the strain of holding back his own impending orgasm, Issei fucks into Griselda’s pussy until he manages to penetrate her womb directly, finally pushing past her cervix.
 
The good Sister squeals as she immediately climaxes on his cock from the deep, unexpected intrusion. Her womb is left impaled on his shaft, as he continues to piston in and out of her. Shuddering, spasming, gasping her way through orgasm after orgasm, Sister Griselda claws at the floor, losing any semblance of cool that she might have had left, the last of her composure and aplomb positively falling off of her as she HOWLS in abject ecstasy.
 
Issei grins a vicious grin, positively bearing his teeth as he forces Griselda to shed her attitude and reveal her true feminine self. The Grade A MILF is all his, and not even this higher up from Heaven is going to change that. No, Issei Hyoudou has claimed another woman. With a triumphant roar and a lustful growl, the Red Dragon Emperor proceeds to fill Griselda with his seed, pumping the hot thick load into her womb directly.
 
Shuddering in response, the human woman gasps and then slumps, all life seemingly going out of her. But no, her body continues to rise and fall, and she continues to breath. She’s just passed out, he discovers as he pulls out of her with a grunt, smacking her ass one final time before straightening up. As Griselda’s freshly fucked quim begins to disgorge the white, hot seed that he’s just filled it with, Asia, Xenovia, and Irina are quick to move in on him.
 
The three girls all want their own turns, after all, and they’ve decided they’ve waited long enough to get a piece of Issei. Luckily, there’s more than enough of him to go around.
 
-x-X-x-
 
“Gagkh! Gagkh! Gagkh!”
 
A few days later, Issei finds himself sitting on a couch in the Student Council Room, a certain Student Council President kneeling before him, greedily gobbling down his cock, choking herself on it. After all, his hands are nowhere near her. Instead, they’re occupied with touching a sluttily clad Shrine Maiden. Sona’s Queen moans into Issei’s mouth as he reaches into her loosened top and gropes and squeezes her breasts to his heart’s content.
 
Sona, meanwhile, has her glasses askew as she gurgles her way up and down his cock, one hand massaging his balls almost tenderly, while the other is all but fisting in and out of her cunt.
 
Heaven’s higher power still hasn’t shown up. Issei figures it’ll be any day now, but at the same time… he’s not going to refrain from living his life while waiting for them. When it happens, it will happen. Of course, given he’s expecting them, is it any surprise that when a sudden glow fills the Student Council Room, causing Sona and Tsubaki to pull away from him and shield their eyes, that he assumes its going to be an angel?
 
What he gets instead is a devil dressed up like a Magical Girl. As the dust settles, the pigtailed devil does a little twirl, a cocky confident smile on her lips.
 
Magical Girl Satan Pink has arrived, tee-hee! Sera-tan is here to show her So-tan all the… love… in…”
 
Coming out of her spin, which definitely includes a panty flash that Issei commits to memory, the self-identified ‘Magical Girl Satan Pink’ finally seems to take in what’s happening in the room, what she’s just intruded on. Her eyes dart between him, Tsubaki, and Sona’s kneeling form over and over again, her mouth opening, slightly agape as she takes in the sight of his cock out and Sona on the floor in front of it.
 
Immediately, the bespectacled Student Council President hops to her feet.
 
“S-Serafall, this isn’t what it looks like!”
 
Tsubaki also gets to her feet, looking worried as she scoffs and nervously crosses her arms over her half-exposed chest.
 
“T-There’s no point in lying to her, Sona. This is exactly what it looks like…”
 
That shuts Sona down, turning the normally icy and composed Sitri Heiress hot red. Not that she’s managed to be composed or cool around him for a moment since the climactic culmination of their little dance. When Issei had claimed not just Sona but her entire peerage, her icy exterior had been irrevocably shattered with him, and they’d both known that.
 
Now though, it would seem Issei is facing down Serafall, and he’s not COMPLETELY oblivious to what’s going on around him. This is one of the Four Satans… Serafall Leviathan… Sona’s sister.
 
Her eyes dart between Sona and his naked dick for a moment more before the incredibly powerful Satan points her ‘magic wand’ at him.
 
“F-Fiend! Give me back So-tan’s chastity! It wasn’t for you to t-take!”
 
“N-No, that’s not true sister! He won m-me fair and square! He beat me! A-At chess!”
 
That wasn’t remotely true. And Issei notices the way Serafall’s eyes widen incredulously for a moment. He realizes then and there… Serafall KNOWS Sona is lying to her. She knows her little sister just tried to cover for him. After all, Issei and Sona hadn’t played chess. Not conventionally, anyways. But then, Serafall would already know that… if she was always watching.
 
Except, if the Leviathan was watching this entire time, then why the fuck was she only just showing up to have this confrontation? She’d known what Issei was doing to her sister for a while now… she had to know, in the same way that he had no doubt Rias’ family knew about their relationship.
 
So, Serafall could only be here now if something had changed. If she had… come to a decision?
 
“T-Then I shall win you back! You there, fiend! I challenge you for Sona’s heart! I will not rest until it once again belongs to me!”
 
“S-Sister!”
 
From the way Sona covers her face with her hands, this is about par for the course for her, but nevertheless deeply embarrassing. Honestly, Issei feels a small degree of secondhand embarrassment on Sona’s behalf, really, he does. But at the same time, he’s intrigued. If Serafall was here to just put him in his place, she wouldn’t be going through this song and dance, would she? So, what did she REALLY want from him?
 
“… What’s in it for me? Since Sona is already mine, why should I accept such a challenge?”
 
As Sona squawks at the fact that he’s even humoring her big sister, Serafall’s eyes gleam, and for a second, Issei gets a glimpse of the cunning mind behind the Magical Girl act. This is only a woman who acts the fool but is far from it in actuality.
 
“I see you are an insatiable beast. Very well, if you win… then you shall have both Sona AND myself! This I swear, on my word as a Magical Girl!”
 
Okay, what the fuck? Exorcist after exorcist, and now devil after devil? When he got to center of THIS mystery, what would he find out about Serafall Leviathan? What was it that drove her to all but fling herself into his arms?
 
Alternatively, he could be reading too much into it based off his previous experiences. Perhaps Serafall WASN’T looking to lose to him. Xenovia, Irina, and Griselda… they’d all been weaker than him to begin with. Serafall… well, he wasn’t quite sure how he measured up to be perfectly honest. Back before, during the battle against Riser, he would have said he was definitively weaker than a Great Satan like Serafall.
 
But after his confrontation with Ddraig, his soul had finished settling, so to speak. His power had grown, undeniably so. Who could say where he stood now that he was as intertwined with his Sacred Gear as he possibly could be? Now that he was the Red Dragon Emperor in truth as well as name, his potential was limitless.
 
Still, accept Serafall’s challenge or don’t… that was the question. The look Sona was giving him made it clear she was hoping he would say no, reject Serafall and send her older sister away. Serafall, meanwhile, is waiting for a response, watching him with intense eyes.
 
It was time to make a decision, one way or another.