The Sleeping Dragon Ch. 85 (High School DxD) (Patreon)

A/N: Runeas gets got, but first...

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Seeing her enthusiasm, Issei smirks for a moment… and then looks to Venelana and Rias.

“You both wanted me to impregnate you again, right?”

“Mmph?!”

Runeas’ muffled, gagged reaction to this makes Issei chuckle as he waves a hand in her direction.

“Quiet now. I’m fully aware that you pressured them into this plan. But that doesn’t change the facts now does it? Rias? Venelana?”

The two female devils exchange a glance at that… before bowing their heads in shameful anticipation.

“Y-Yes…”

“Please knock us up.”

Grinning, Issei waves a hand through the air.

“Very well, assume the position.”

Rias and Venelana doesn’t hesitate, even as Runeas makes angry noises and struggles against her bondage anew. But to no avail. She can’t escape, even as Rias gets on her back so he can take her in a mating press and her mother gets on her hands and knees, expressing her preference for doggystyle.

In the end, Issei also doesn’t hesitate. Rias gets to go first, his cock sliding into the youngest devil’s pussy without resistance, her tight cunt so wet and so slick that there’s not a single issue with him burying his entire length inside of her in one go. Of course, once he IS fully inside of her, her pussy walls clench down and flex along his shaft, milking him for all she’s worth in an absurdly pleasurable fashion.

Rias moans, the young MILF shuddering beneath him as Issei grabs hold of her ankles and pushes her legs further back against her insanely voluptuous body. Fucking her in her favorite position is the least he can do after she brought him such a fun little toy. Plowing Rias Gremory silly for the umpteenth time, knowingly going out of his way to impregnate her again… it really took him back, truth be told.

If it wasn’t for Rias and Sona making such a concerted effort to get his attention back in the beginning, would Issei be where he was today? He didn’t think so. Only through their efforts… and admittedly their beauty, had Issei been truly drawn into this world. And only because he’d been drawn into this world had he been able to meet Gabriel and make her Fall.

From there the rest was, as they say, history. Regardless, Rias had played a huge part in pulling Issei out of his hibernation, for lack of a better word. He’d been resting on his laurels for so long, having awakened Ddraig at such a young age that he’d thought he was already as powerful as he would ever need to be.

Needless to say, he had not been. But… Issei wouldn’t change a thing, in the end. Everything had worked out just as it was supposed to.

Smiling down at Rias, Issei leans in and runs a hand through her red locks before gripping the back of her head and pulling her into a soul-searing kiss. With the big-breasted young woman folded up in a mating press, she can do nothing but squeal and moan into his mouth as he continues to pound her pussy into the shape of his cock yet again.

Plap! Plap! Plap!

Her juicy, sopping wet cunt makes such delicious noises as his member disappears into her over and over. Rias’ eyes roll back in her head as she orgasms for him time and time again. Until finally, with a single grunt expelled into her plush lips, Issei proceeds to cum inside of her. His seed fills her womb and while she definitely had drunk Ravel’s elixir before coming here, that’s not even necessary. As he is now, Issei can guide his swimmers right to Rias’ eggs and despite the difficulty of penetrating a devil’s eggs… well, Issei IS the closest thing to God with a Capital G now.

He might not be as powerful as God himself just yet, but he was plenty powerful enough for this. And so was his seed. With Rias thoroughly bred upon his cock, Issei pulls out of her and leaves her to recover without another word.

Moving over to Venelana next, Issei wastes no time with words where the Lady Gremory is concerned. Grabbing the Flaxen-Haired Madame of Extinction by her hips, he spears into her enthusiastically wet cunt from behind without so much as a ‘by your leave’. Not that Venelana minds, of course. Though, she might mind what he has planned next.

Grabbing Venelana by her brunette locks, Issei yanks the beautiful, stacked MILF around on her hands and knees, forcing her to face Runeas Gremory. Still bound and gagged and unable to escape, the Gremory Ancestor is moaning through her ball gag at this point, humping the air with her crotch because that’s all she CAN do in her current helpless position.

She goes still for a moment as Issei forces her and Venelana to look at one another, however. The two might not be blood related, but Runeas’ words from last time had given Issei somewhat of an idea of what the ancient she-devil liked.

“Tell her how good it feels, Lady Gremory. Tell her what I’m doing to you. And tell her what I’m going to do to you.”

Shuddering, picking up quite quickly on what Issei is after, Venelana moans for a moment before speaking through wanton mewls and squeals.

“H-He’s fucking m-me so hard, M-Madam Ancestor… A-Ah, I’m sorry… I’m sorry, but he’s so much better than your descendant, my husband! His cock feels so good! I love it! I love it so much!”

As Issei fucks her, he feels a little sorry for Lord Gremory. But this isn’t really about the other man and from what Issei knows, Lord Gremory is doing just fine with his own harem. No, this is about Runeas Gremory… and how hot she apparently finds it for him to have cucked her most prominent male descendants.

It wasn’t really possible to argue that in Issei’s opinion. The originator of House Gremory had heard all Issei had done, how he’d fucked Venelana, Rias, and Grayfia as well into countless stupors. And upon learning this, what had the First Gremory done? Had she come to him to do battle? Had she tried to fight to reclaim the honor of her House, or even sought to punish the women of House Gremory for their failures?

Nope. She’d bullied Venelana and Rias in turn, forcing them to bring him her bound and gagged form. She’d only defaulted to pretending to care about her male descendants AFTER Issei had exposed her little gambit.

“He’s stirring up my insides, Runeas! His big fat cock is stretching my cunt out like nothing else ever has and he’s preparing to fill me up!”

Runeas was loving this. Face almost as red as her hair, eyes wild with excitement and libidinous lust, the Gremory Ancestor is watching Venelana get fucked by Issei with an intensity that actually surprises him a little bit. She’s panting through her ball gag, flustered and needy. She’s getting off just on the sight before her and the words coming out of Venelana’s mouth.

“He’s going to breed me, Runeas! He’s going to knock me up… AGAIN! With this, he’ll have given me just as many children as Zeoticus has, but in less than a single percent of the time! And I’m s-sure he’ll give me many, many more in the future! He’s just… so… MANLY!”

Venelana squeals, her eyes rolling back in her head as she talks HERSELF into ahegaoing all over his cock. Her tongue lolls out of her mouth and Issei chuckles before giving her what she’d just described. He cums inside of her while she’s in the midst of ecstasy, redoubling and prolonging the length of her explosive orgasm. Only once he’s done cumming inside of her does he pull back and release his grip on her hair.

All that time, Venelana’s massive tits had been bouncing and swinging from the force of his thrusts, but he’d paid them no mind. Now, he gives them a good solid grope, squeezing them for a moment only to find Venelana is very much still lactating. Hm, Rias might have been as well.

Regardless, flipping Venelana onto her back, he gives each of the insensate woman’s teats a good, long pull with his lips, drinking deep of her breast milk… all while keeping eye contact with Runeas the entire time.

By the point where he pulls away and rises to his feet, Runeas is more than ready for him. Bound, gagged, and truly helpless, the Gremory Ancestor trembles in anticipation and excitement as he finally ambles his way over to her.

Needless to say, Issei doesn’t hesitate to start with the obvious. Grabbing hold of her by her pigtails, he honestly can’t imagine another use for the damn things except as handlebars. Which is why he yanks them rather roughly, even as her ball gag disappears in an instant. Her mouth is still wide open though, allowing Issei to shove his cock into its place before Runeas can even realize the restricting device is gone.

“Gaaaaaaaaagkh!”

“Suck it, bitch.”

Runeas doesn’t waste any time. Her tongue immediately starts to swirl around his cock like it has a mind of its own, and her cheeks suck in so hard she looks like she’s come right out of a fucking hentai doujin. Her plush lips latch down upon his cock and the look in her eyes is one of pure excitement as she happily chokes and gags on his cock.

“Glughk! Glughk! Glughk!”

She loves this, the silly cunt. Issei supposes he isn’t surprised really…

“You think you’re better than Gabriel, do you? Well… you’ll have to try harder than that.”

Runeas’ eyes widen at the comparison, forcing her to somehow find the strength to redouble her efforts. Issei groans in appreciation, causing a triumphant look to appear in her eyes. But the truth is… she can’t beat Gabriel. In fact, it’s her try hard nature that automatically disqualifies her from ever competing with Issei’s beloved. Gabriel… is effortless. Runeas Gremory cares way too much. That’s why she can never win.

Of course, that’s not going to stop Issei from taking advantage of her competitive nature to its fullest extent.

“GAGKH! GAGKH! GAGKH!”

Even though he’s still holding her by her handlebars, Runeas is actually driving herself down upon his cock with greatly increased speed and vigor now. The bitch just doesn’t let up, her tongue writhing like a mad thing, her lips suctioning like there’s no tomorrow, her throat convulsing around his cock. Finally, when she dives down his length one last time, Issei grabs the back of her head and holds her there, ignoring her involuntary struggles as he proceeds to cum. And cum. And cum.

His seed explodes down the back of Runeas’ throat and at first the First Gremory handles it like a champ. Clearly she’s been expecting this and she immediately begins swallowing like there’s no tomorrow, not struggling for even a moment. One might describe her as the Throat GOAT, if one had to. But just because she turns out to be absolutely amazing at guzzling cum doesn’t mean Issei is just going to give it to her.

He keeps cumming. Far past what any normal man would be capable of. Far past what he even did to Rias and Venelana. He keeps cumming and cumming, until Runeas’ eyes start to widen in realization. But by that point it’s too late anyways. Or more accurately… there was never anything she could do about this in the first place.

As his seed fills her belly, Runeas doesn’t actually have an unlimited amount of space inside of her to work with. And eventually, she can no longer keep swallowing. If she wasn’t sure it was purposeful before, she’s probably certain of it once Issei cuts off his unending ejaculation mere moments after Runeas fails to contain his seed, which comes exploding out of her nostrils and the sides of her mouth with extreme force.

Once she’s got a really messy face and glazed expression, only then does Issei pull out, letting one or two last ropes of his seed coat her already ruined features before finally stopping.  Then, he gives her a grin.

“Well… I’d say that was a B Minus. Needless to say, you did not manage to surpass Gabriel.”

Rapidly recovering, especially at hearing she’d failed, Runeas blinks rapidly before growling up at him.

“I-I’m not done yet! Fuck me, Issei Hyoudou! Fuck me and you’ll see how amaz-IIIIIING!”

Well, he’s certainly not going to deny her. Even still, as Issei lifts Runeas’ bound body up into the air and spins her around before impaling her on his cock, he chuckles, knowing full well that she’s never going to surpass Gabriel. Not as she is now, anyways.

Driving her down onto his member after noting the lack of panties, Issei begins to fuck Runeas Gremory hard and fast from below, causing the pigtailed red head to squeal and shriek as she cums over and over again. Rias’ poor school uniform can no longer contain her ancestor’s tits either, not with the force that Issei is bouncing her.

Buttons go flying everywhere, and Runeas’ breasts pop out. Grunting, Issei lets go of her hips and lets his cock do all the work down below, his hands moving to grab and squeeze Runeas Gremory’s fat milk jugs as he fucks and fucks her. Of course, he’s not going to fuck her for an eternity. Eventually, this has to come to an end. And so Issei leans in close and whispers in the Gremory Ancestor’s ear.

“Do you want it? Do you want to be bred on my cock, Runeas Gremory?”

She doesn’t have to think about it for long. With a squeal, Runeas nods her head up and down frantically.

“Y-Yes! Yes, it’s been so long! But no one’s been worthy! Fuck me! Breed me! Knock me up you big dicked bastard!”

Smiling, Issei proceeds to fulfill her wish. He slams Runeas up and down his member without even using his hands, pounding up into her pussy from below with his whole length again and again. At the same time, he continues to maul her breasts, already looking forward to what they’ll be like when they’re full of milk later on.

Until finally… he fills Runeas up. His seed pumps into her womb like it did with Rias and Venelana, and he cums for a good long while. This proves to actually be necessary, because not only has Runeas not taken Ravel’s Elixir, but she’s also a lot stronger than Rias and Venelana. Meaning her eggs are tougher too.

But Issei just floods them with his semen until eventually one penetrates. He feels the moment of conception… and then casually and rather callously drops Runeas onto the floor on her face, still bound in enchanted rope.

As she squirms, flopping around like a fish, Issei just grins down at her.

“B Plus. Still not as good as Gabriel though… she would never have begged.”

Not entirely true… Gabriel was happy to beg for him when they were roleplaying sometimes. But there was a difference in Issei’s mind. Of course, even as he walks away from the room, leaving the three devils to recover… he can feel Runeas’ attention on him. The First Gremory isn’t going to let this insult stand. Rather, she’s going to do everything in her power to eventually overcome Gabriel.

Issei expects her to be a lot more active going forward, rather than fucking off for a few centuries again like she usually did. Which is good, because as much as Runeas is a total horndog and a full-blown narcissist, she’s not a bad person, at least by devil standards. Having someone like her more active in the world would only help his plans for the future. Whether she realized it or not.

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Also I was originally gonna parcel all the ideas I have for epilogue chapters as options over time, but realized if I did that I would forget half of them because of how bad my memory is.

So consider these all the ideas I currently have that I'm definitely going to write before the story ends. You guys are just voting on the order they show up in.

There's also going to be one final Epilogue Chapter between Issei, Gabriel, and F!Ddraig so you don't have to worry about those two gals not getting a proper send-off.

That said, anyone particularly egregious you feel I've missed here? Also feel free to give me your ideas for what you think some of these chapters should look like. I have my own ideas (for instance, The Queens chapter will almost definitely be Maid Play) but am always willing to consider alternatives.