Unexpected Spoils (High School DxD) [RELEASED] (Patreon)

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Themes: Threesome, Catgirl, Rough Sex 

Summary: In a bid to regain his honor and get Rias back, Riser challenges Issei again. But this time he's negotiating from a position of disadvantage, and has to ante up something more... worthwhile. By the time all is said and done, Issei has won, and all eight of Riser's pawns now belong to the Red Dragon Emperor. What's a boy to do with his newfound harem but start with the catgirl twins, Ni and Li? 

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“Enjoy~”

And with that, the door closes and Issei is left alone with two cute, twin catgirls, both of them kneeling in the seiza position with their hands atop their legs and their eyes fixated on him. Their ears are twitching, and their tails are swishing back and forth behind them, like the two of them want to pounce on him right then and there.

Swallowing slightly, Issei considers the situation and just how it’d gotten to this point. He was… he was pretty sure he’d lost track of what was happening a while ago. He’d been completely on board back when it was that bastard Riser trying to make Rias marry him against her will. Beating Riser up and ending the engagement had just made sense.

But then, a few weeks after everything was supposed to be dealt with and over, Riser had shown up again, like a bad penny that just didn’t know when to quit! He’d challenged Issei to another fight, just the two of them, one on one, for Rias’ hand. That should probably have been Issei’s first clue that something was wrong. After all, Issei was just a pawn, at the end of the day. Sure, he had Ddraig, but he wasn’t anyone special, right?

And yet, Riser had been very clear in who he was challenging. And then Rias had stepped in and demanded to know exactly what Riser was going to offer in exchange. That had flummoxed both the bastard bird and Issei, but given how much it confused and surprised Riser, Issei had been all for it. That bit had made sense too, and still did now after all. Riser had lost the right to have Rias marry him when Issei had won their duel… so obviously, now Riser had to offer something of equal value to Rias or something.

See, that was where the next part didn’t make much sense to Issei either. Riser had offered up his pawns. All eight of them. And while eight girls for one may not have seemed equal in one way, really, it wasn’t equal in the other way. Rias was worth more than eight measly pawns, right?! But his Buchou had agreed to the terms for Issei, and Issei had found himself once again fighting Riser on Rias’ behalf. Or so he thought.

Because after he won, which he did because even without the holy water and the cross he’d used in their last duel, Issei had grown leaps and bounds in the weeks after, everything had abruptly gone crazy. The court had even ended up being involved! And not the human court, but the Devils’ version of court! Yeah, that was about where everything had really started to go over Issei’s head.

Something about how, Riser had challenged Issei instead of Rias, and thus elevated Issei in status beyond a regular pawn just by recognizing him as an adversary. And then there was the fact that Rias had used all eight of her pawns on Issei, and thus had no more pawns to take Riser’s off of his hands anyways. But the challenge was still considered valid, which meant that Riser had to ‘pay up’ as it were.

By the end of things, Issei was given some kind of weird status as a demi-King or something? At least, that was how Rias had explained it to him. He was still part of her peerage, and he still had all eight of her pawns inside of him. But on top of that, he’d been given half of a chess set for himself, in particular, eight of his OWN pawns. These had then been put into Riser’s pawns once Riser’s pawn pieces had been removed from the girls, and now they were Issei’s pawns.

… Yeah. Needless to say, Issei didn’t think it was unreasonable that, rather than deal with all eight of his new pawns at once, he had decided to handle them a little more… slowly. So, here he was, alone with two twin catgirls. Who were now his pawns. And still waiting for him to say or do something. Licking his lips, Issei looks between them, before suddenly pointing.

“So… you’re Ni and you’re Li, right?”

The two catgirls glance at one another and then slowly nod. Ni is the one with blue hair and red eyes, while Li is the one with red hair and blue eyes. Right… that’s not going to be easy to remember at all. Rubbing his own eyes for a moment, Issei frowns slightly as a thought comes to him. Licking his lips, he looks at the catgirls again.

“Are you guys… okay with this?”

He’d never been good at talking with girls before, but then he’d died and come back as a Devil and Buchou and his friends had done a lot to help him grow and mature as a person. Just a little. Enough that Issei wasn’t about to do anything if they hated him for taking them away from Riser or anything. Though it really didn’t help that the twins were dressed in these skimpy, ill-fitted schoolgirl ‘uniforms’ with the sleeves torn off and the lower half of their breasts exposed along with their abdomens!

Regardless, his question causes the twins to glance at one another yet again, before turning back to him. Its Li who speaks up smiling slightly as she leans in.

“Why wouldn’t we be okay with this? We’re finally where we belong. You’re our master now, Issei~”

Beside her, Ni nods along emphatically, showing her agreement with her sister. Issei, meanwhile, just sits there with his mouth dry and his eyes wide. He had to… resist… the temptation…

“Then show me your tits! Oppai!”

And like that, he’s sure he’s ruined it. But honestly, what was he supposed to do in the face of such a declaration?! If there was one way to get Issei to have an outburst, it was to say something lik- holy shit they’d actually done it. Issei just stares at the twins before him. Both sets of them. The catgirls, without so much as pausing, have both pulled up their very skimpy tops and let the rest of their breasts fall free of their confines.

They aren’t overly large, either of them, but that’s okay. They’re perky and beautiful, and Issei has always been of the opinion that breasts were breasts! All oppai were good oppai!

“C-Can… can I touch them?”

“Of course you can!”

“P-Please do, Nya~”

Issei doesn’t need to be told twice. He’s across the room in the instant, and his hands are all over the catgirl sisters as he begins to molest both Ni and Li on the spot. They moan in response, their breasts rubbing into his grip as they jut their chests out eagerly in response. H-Hot damn! They really wanted this! They were actually willing t-to let him do what he wanted with their oppai!

The young man was in heaven, needless to say. And the more they moaned and mewled in his grasp, the more emboldened he became. Leaning in, he begins to take their tits in his mouth. His hands end up regulated to the outside of the four delicious boobies before him, while his mouth and tongue and teeth change between the inside of their chests, alternating back and forth between Ni and Li and Ni again without pausing, without hesitating.

Part of him still thought this might be some kind of dream, if he was being honest. But if it was a dream, Issei wanted to continue enjoying it for as long as it lasted! Eventually, he pulls back, unable to contain himself anymore. Literally, his cock was straining almost painfully against the inside of his pants by this point!

“I want to have sex with you both!”

Ni and Li blush deeply at that, and exchange another glance… but when they turn back to him, they each nod speak in unison.

“W-We would like that too!”

Letting out an unintelligible shout of joy, Issei basically tackles both girls to the ground at that point, too turned on, too aroused to hold any part of his perverted personality back any longer. He wasn’t going to let this chance slip through his fingers! But at the same time, neither Li nor Ni seemed at all displeased with his forwardness, or his roughness.

The first real explanation for why they were both so eager came when his cock finally came out after several moments of writhing bodies and moans and tongues in places that they’d never been before. Both Ni and Li gasp at the sight of his shaft, and before he knows it, Li is grabbing his length with both hands and guiding it between Ni’s legs as she blushes prettily and half-covers her face with her hands.

“N-Ni first! I promised her, okay?”

Issei just nods, eyes wide as Li takes care of pulling up Ni’s short skirt and pushing aside her cute, white panties. Then, his cockhead is pressed against pussy lips, and beginning to penetrate a woman for the first time. Holy shit! He’s losing his virginity! This is actually happening! Issei groans as he throws his head back from just the tight feel of Ni’s gripping cunt around just the tip of his member. It feels amazing, better than he ever expected it to feel.

But Li’s not satisfied with just that, and before Issei knows what’s happening, his cock is disappearing into the blue-haired catgirl as he pushes past some barrier, tearing through something. Only his knowledge of hentai and porn really tell him what just happened. He just broke Ni’s hymen! When that realization finally gets through the haze of happiness and pleasure that’s filling him to the brim, Issei’s eyes go wide and his jaw drops open as he looks to both of the twin catgirls in disbelief.

As if they’ve been waiting for that reaction, Li explains, even as Ni whimpers and mewls and wiggles around his cock, which even now is being fed deeper into the catgirl’s tight, virginal insides.

“Riser was… kind of a loser. He was a loser with way too much power because of the family he was born into. He wanted a harem, but not to use, just for show. He wanted us as his trophies, to show how manly he was.”

Issei’s mouth opens and closes a few times, even as he begins to instinctively thrust into Ni while staring at Li in shock. As he fucks the mewing catgirl, she wraps her legs around his waist and pulls him in all the deeper, her hands now on her breasts rather than her face as she truly gives into the pleasure.

“How could… how could he leave such beautiful flesh untouched though?! What’s the point of having a harem if you don’t enjoy the oppai and the girls to the fullest extent?!”

Li just smiles and nods, even as she leans over her sister, cooing down at her intermittently as Ni thoroughly enjoys her first time getting fucked by a real man. Those were Li’s words, in fact, a moment later.

“Riser was a limp-dicked bitch. Hehe, it feels so good to say that now! We found out from Yubelluna, because he made sure we never saw it, but he has a REALLY small penis! So he wasn’t willing to interact with us in that way, because even those we were effectively his slaves, he was still inadequate. As far as I know, he only ever actually fucked Yubelluna, and as she described it… well, ever heard of a two-pump chump, Issei?”

Slowly, the young man nods. Li glances down at where he’s still instinctively pounding away at a currently-climaxing Ni and grins.

“Opposite of you, I can see. Anyways~ Riser is more like a half-pump chump, if ya know what I mean.”

Then, Ni leans forward and caresses Issei’s face as she kisses him on the lips. When she pulls back, she grins impishly.

“But you… you’re a real man.”

That’s about all he needs to hear to go right over the edge. With a groan, Issei tilts his head back and fills Ni with a nice, thick load of his seed. The blue-haired catgirl’s back arches off the ground and she tugs at her own nipples as she feels it happening, and then, once it’s done, she collapses back, panting heavily and catching her breath.

Issei finds himself a little breathless as well, but the moment he pulls out of Ni, Li is there, bent over and taking his half-hard prick in her mouth as she both sucks it clean and gets him back to full length. She’s quite eager for her turn, Issei can just tell, and as soon as he’s erect again, which doesn’t take long at all given the circumstances, Li spins around and the red head presents her ass to him as she pushes her own panties out of the way, revealing her drooling quim.

Issei doesn’t even need to be told at this point. His hands grip hips, and then he’s pushing into Li from behind. He’s not surprised this go around when he breaks through a hymen, and he’s soon settling into a nice, rhythmic thrusting as he fucks his second girl ever. Holy shit! He’s losing his virginity to TWINS! And not just that, but twin catgirls!

This is the best day of his life… though as he pounds Li from behind and she squeezes down HARD around his cock through every orgasm, what she’s said does make him wonder some things. Like for instance…

“Do all of Riser’s former pawns think like you two do? Are they all this eager?”

Giggling, Li looks back over her shoulder at him, her eyes sparkling as she licks her lips. Her tail swishes up and brushes back and forth across his chest playfully while he continues to slam into her from behind.

“They will be once Ni and I sing your praises, Issei. And they certainly will be, once they realize we have a REAL man for all of us to share now. Oooh, fuck me Issei! Fuck me!!!”

Li’s head tilts back and Issei can see her eyes rolling backwards as well as her inner walls get so much TIGHTER between one moment and the next. He fucks her, just as she asked, and soon enough he cums inside of her, just like he did her sister. As he pulls out, Li slumps forward onto her front, laying beside Ni, their fingers intertwining as they hold hands. And Issei just stares at them both for a long moment, swallowing thickly.

This is his life now… these women are his responsibility. More than that, they’re HIS. A possessive curl of fire builds in Issei’s chest, and he finds himself stoking it as he looks down at the two catgirls before him. Lookinge ven further down, Issei can see that his cock is still rock hard. With a little grin on his face, Issei gets to his feet. Something has awakened within the young man… something draconic. And now that he has the start of his hoard, he’s not going to stop.