The Sleeping Dragon Ch. 40 (High School DxD) (Patreon)

A/N: Issei's fighting for his life here guys. Guys? Why are you laughing, this is his hardest struggle to date! :V

-x-X-x-

“… Deal. Double or Nothing.”

At the end of the day, it’s an odd situation to be in. His choices are a variety of different ways he’s going to end up having sex with a Great Satan. Because no matter what, he and Serafall are about to fuck. After all, even accepting her deal means they’re going to have a ‘sex battle’. It’s just a matter of whether or not he wants to risk more for this bet they have going.

And the truth is… he does. He is, after all, a dragon. His greed is unparalleled, his desire for more and more unmatched. His hoard of women can only grow, never diminish. Even if Serafall thinks she’s fighting for Sona’s… whatever, Issei knows for a fact that Sona will resist being dragged away from him with all her might. And, siscon that Serafall is, she probably won’t be capable of truly steeling her heart and breaking Sona’s in the process.

So yeah, the stakes really aren’t that high here. Doesn’t mean Issei isn’t going to give it his all though.

“Great! Then… we shall start with a Sixty-Nine!”

Sona covers her face with her hands, as Issei just nods in amusement. Tsubaki ends up exiled from the couch, the barely conscious bespectacled devil girl pulled away by Sona as she mumbles and moans. Issei lays down across the couch and Serafall hops on top of him, the cosplaying Leviathan revealing her pure white panties, up under her magical girl skirt. Seriously? Where did a devil get off on trying to look so innocent?

Grabbing him by his cock with both of her gloved hands, Serafall looks back at him with a determined glare.

“We shall have three rounds! First to two points takes it! Whoever cums first each round wins! Now… to start with, Oral!”

And then, not really giving any kind of countdown, Serafall leans forward and tackles his cock with her mouth. Issei’s eyes widen as she swirls her tongue around his glans, and he quickly leans up, flipping her skirt up and out of the way and tugging her panties aside. She’s not quite as wet as he might have liked, but she’s also not completely bone dry. Indeed, the events of the day have been at least a partial turn on for the Great Satan.

That said… her oral technique is phenomenal! As something of a glutton of debauchery and depravity, a purveyor of perversity, Issei knew the difference between experienced and inexperienced. More than that, he knew the difference between experienced and mastered as well.

As Sona’s sister goes to town on his cock, she doesn’t do so with over the top enthusiasm or an eagerness that makes her sloppy and undignified. Rather, she attacks the project like one might a particularly difficult task, and approaches the matter at hand with more technique, skill, and levelheadedness than Issei was ever expecting.

He’s barely gotten his tongue up inside of the Leviathan’s quim, before the first involuntary groan leaves his lips. While the feel of his hot breath against her nethers DOES prompt a twitch and a fresh bit of leakage from the Great Satan, it’s immediately obvious that Serafall is… well, already way ahead of him.

Oh? Is the Red Dragon Emperor struggling?

Issei can only growl, as Ddraig’s feminine voice fills his head. The genderbent dragon in his soul, the one he’d put in her place a little while ago, sounds almost teasing as he tries to focus on the challenge before him, a possibly insurmountable one at that.

What? Did you really buy into this devil’s act, for even a moment? She’s a Great Satan, sweetie. You didn’t think she was some innocent, naïve powerhouse just waiting to be taught the joys of sex… did you?

No! Of course not! He hadn’t thought that at all! He just… he hadn’t realized she was fucking hustling him. Because as Serafall descends down his cock with her masterful tongue strokes and her gently but firmly sucking lips, Issei is having a really hard time holding back his release. His hips are even lifting of their own accord, his cock thrusting up further into her mouth, or rather trying to. His balls are churning with a need to release their payload into this salacious, seductress’ mouth.

Meanwhile, his own efforts are far from bearing fruit. Oh sure, Serafall is wetter than when they started, but there’s no denying how lopsided this Sixty-Nine is so far, and how behind Issei has become. His tongue and fingers dance over Serafall’s sex, but in the end, all he can truly manage to do is prepare the field, so to speak. His only chance of winning, is to get ready for Rounds Two and Three.

Smart. She’ll be ready to blow in the next round if you can hold out a little longer. But then, she’ll be fresh off of that round and YOU will be primed and ready to blow going into Round Three.

Ddraig is right, of course, but Issei sees no other choice. And so, he holds out as long as he can, even though this first round’s loss is… inevitable. As he finally blows his load, Serafall wastes no time swallowing every last drop, not letting a single bit of his seed escape her mouth. As she pulls back with a gasp, she looks at him with a wicked smirk.

“Round One to me then, Dragon.”

Issei can only grudgingly nod, as she hops off of him and he gets to his feet, raising a brow.

“Then onto Round Two. As the victor, I’ll let you pick the position.”

Serafall hums for a moment, even as Issei notes the trail of clear liquid, evidence of her arousal, leaking down her inner thigh. After a moment, a truly fiendish grin spreads across her face.

“Mating Press! While holding hands!”

“S-Sister!”

As before, interestingly enough, Serafall doesn’t pay Sona the slightest bit of attention. Issei does though, even as he moves to grant Serafall’s request. Pushing the Great Satan down onto her back, and then pushing her legs up into the air before driving his cock into her. Sona Sitri is watching them with wide eyes, one hand covering her mouth, and the other down between her legs.

It doesn’t look like she’s directly fingering herself, but she’s definitely lost the battle for her dignity and has descended to grinding the heel of her palm into her cunt. Meanwhile, from the look in Sona’s eyes, it’s quite apparent that despite Serafall’s bombastic, over the top attitude, this is the most sexually aggressive that Sona has ever seen her.

As he begins to fuck Serafall hard and fast, the magical girl moans and throws her head back and forth, decrying him even as her lewd smile gives away her true feelings.

“N-No! You wicked fiend! You’ve taken my Magical Girl Purity! Oh no! Please don’t cum inside of me, that would ensure impregnation and take away my Magical Powers foreeeever~”

Issei didn’t think Serafall’s sudden roleplaying was for his benefit necessarily. Rather…

She knows she has no hopes of winning two rounds in a row. She can tell she’s already close to the edge. She’s all but giving you this round, because she knows she’ll win, in the end.

Ddraig’s words make him grit his teeth. That was precisely the same conclusion he’d come to, except for that last bit. She THOUGHT she would win in the end, but that didn’t mean her victory was assured! Not yet!

Hehe, ah, always so prideful. You’re out of your league, Issei. Can’t you tell?

Hmph, that was pretty much what Ddraig had said before he’d defeated HER and look how that turned out.

T-That’s different!

Was it? Issei surges forward into Sona’s sister, fucking Serafall Leviathan with all his heart, even as the magical girl cosplayer continues to cry out about what a monster, he is for deflowering her and taking her purity. Serafall is really into it, and Issei… Issei turns that to his advantage, absolutely savaging her. He likes to think he sees a hint of notice in her gaze, a small spark of what’s really going through the Great Satan’s mind, even as he plows her as hard and as fast as possible, trying to extract that orgasm from her before she can get him too far along towards his next release.

In the end, the ahegao face Serafall makes is completely fake, but the orgasm that she makes it to accompany is decidedly not. Eyes rolling back in her head, tongue lolling out of her mouth… THOSE bits are completely voluntary. The tightening of her quim around his cock, the flood of pussy juices down his pistoning length… THOSE are not.

Growling lustfully in triumph, Issei leans in close.

“Round Two goes to me, it seems.”

As he pulls back, Serafall’s eyes flash forward and grow lidded as she gives him a wicked smirk.

“Mm… one round left then. I assume you know which hole our final battle shall be fought within. As the victor of this round, you get to choose the position.”

Of course. Issei was no idiot. He knew where this was expected to go next. And while he could have tried for something exotic or unique, in the end… why mess with a good thing? Sometimes, the classics were all you needed.

Flipping Serafall over onto her front, he lifts her hips up into the air, pulling the magical girl cosplayer to her knees while leaving her face down on the ground. Serafall, to her credit, doesn’t so much as move out of the humiliating position. Face down, ass up… this might be the most disgraceful pose that the Leviathan has taken in centuries, and that’s saying something considering she’s literally dressed like a Magical Girl.

Still, Issei has his hands on her hips, and pulling her pure white panties down to her knees is a moment’s work. Her ass and her glistening wet cunt are both on display before him, as his cock, twitching and throbbing and covered in Serafall’s juices, glistens in the artificial light of the room.

Sona watches, as he spreads her big sister’s cheeks and presses the head of his cock against Serafall’s asshole without hesitation. Waiting too long to start Round Three might be construed as cheating after all, and even if he was doomed to failure, he wasn’t going to go out dishonorably.

Heh, that’s the spirit. You’re going to lose, but you might as well do so with your head held high.

Regardless of the final outcome of this confrontation with Serafall Leviathan, Issei was one hundred percent entering his soul space later tonight when he went to sleep, and he was going to bend Ddraig over his lap and spank her silly. Really, where she got off teasing him like this, he knew not.

Still, for the moment, he had enough on his plate, and he wasn’t ready to give up just yet. Even if, as he begins to fuck Serafall’s ass, it does feel a little hopeless. Oh, don’t get him wrong, Serafall grunts and groans and shudders as he plows into her backdoor. She’s clearly feeling it and enjoying herself at least somewhat. He’s more than lubricated enough for this, making the passage slick with her own juices as he plunders her anus.

… But Issei can immediately tell that Serafall is not some anal slut, even if that would have been precisely the boon, he needed to carry him through the day. Unfortunately, while she’s certainly not hating the anal sex, she’s also not getting off on it nearly as much as he would need her to be in order to win this challenge.

That doesn’t stop him from gripping and squeezing her ass cheeks, fucking her hard and fast as her body jiggles and jolts with his thrusts. Fuck, when else is he going to get a chance to fuck a Great Satan like this? When else is he going to get a chance to butt fuck THE Leviathan? Especially if there’s no hope of victory. Unless…

Sona is still watching. She’s watching him fuck her sister in such a compromising position, and at this point she’s graduated from grinding the heel of her palm into her cunt, to outright fingering herself. As he makes eye contact with the Student Council President, she freezes up… but only for a moment before blushing and continuing to touch herself all the same.

There’s his out.

Oh?

Ignoring Ddraig, Issei grabs Serafall by the hips and suddenly shifts her several inches, turning her in a different direction. The magical girl cosplayer yelps as his cock, still buried in her ass, jostles her insides a fair amount, but she doesn’t try to fight him. Instead, she lets him do as he will, confident in her eventual victory. That proves to be her last mistake.

Reaching forward, Issei grabs the magical girl cosplayer by the twin tails her raven-black hair is done up in. Yanking them back line reins, she brings her up off of the ground, drawing a startled moan from her lips… even as he brings her into the direct line of sight of her debauched, depraved little sister.

Sister and sister freeze in unison as they make eye contact with each other. But Issei, still pulling on Serafall’s hair, just grins as he fucks into her ass from behind.

“Look at her, Sona. Look at how depraved your sister TRULY is. And you, Serafall. Look at how turned on your precious So-tan is. Look at how she’s getting off on watching you get FUCKED.”

Sona whimpers, but Serafall’s reaction is much more pronounced, and this time, Issei can tell her distress is real.

“Noooo! S-So-tan! Don’t look at me! I can’t… I can’t! S-Stop staring at me!”

Still fucking Serafall’s ass, Issei can tell this alone might not be enough. So, he looks Sona dead in the eye and smirks.

“Sona. Come here.”

The Student Council President jolts, and then pushes off the desk she was leaning against, stumbling over with her hand still down her panties. She stops just in front of her sister’s kneeling form, even as Issei continues to impale Serafall’s ass from behind.

“You want me to keep fucking you, don’t you?”

At the start of this little encounter, Sona would have been mortified to be asked a question like that in front of her big sister. But now? Oh, how quickly things could change.

“Y-Yes…”

“Tell your sister that. Tell her how badly you want me. Tell her to cum for me, for you… for both of us.”

“N-No! So-tan, run! He’s a monster! He’s an evil monster who’s corrupted you with his mind powers!”

Despite Serafall’s pleas, Issei can tell she’s getting off on this. She’s getting off on the inclusion of her sister in their little competition. Sona… Sona sees this too, and with a sense of finality, drops to her knees in front of Serafall, taking her face in her hands. Transitioning his own grip on the magical girl cosplayer to her wrists instead of her hair, Issei pulls Serafall’s arms behind her back so she’s helpless to stop Sona from doing whatever she needs to.

Issei isn’t sure what he was expecting from the younger Sitri sister… but in the end, it’s not what he gets. Sona leans forward, presses her forehead against Serafall’s own, and looks into her eyes. Then, she very quietly pleads with her sister.

“P-Please Sera… please cum for Issei so we can both have a lot more fun together.”

And… that does it. Serafall tips over the edge at her sister’s request, and not a moment too soon either. As Serafall lets out a keening wail and cums all over the floor between her kneeling legs, Issei lasts maybe a handful of thrusts more before the incredible tightness of her anal passage causes him to go over the edge as well and paint her bowels white with his seed.

As he finishes inside of her, victorious, Issei can only pull back and pant heavily. That had been close. Out of all of his battles… this might have been the toughest yet. But still, he was now the victor. And all that was left was to claim his spoils. Though, while he could demand Serafall immediately summon this Queen of hers so he could have her and the Leviathan together… didn’t Sona deserve a reward for her help? He couldn’t have done it without her…