A Perfect Match (High School DxD)

A Perfect Match (High School DxD)

A/N: A Perfect Match was a commissioned one shot originally written back in September of 2019. Posting it here and now for readers to enjoy!

Summary: In a bit of a twist on the common scenario, Riser doesn't have to win a Rating Game or use Mind Control to make Rias fall in love with him. As it turns out, Rias Gremory is simply slutty enough and enamored enough with the power that the Phenex Family represents that she's perfectly okay with their marriage, and eager to get some.

Themes: Slutty, Rough Sex, Dom/Sub

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"W-Who... who is this Buchou?! Why are you so chummy with him?"

Riser rather lazily turns his gaze towards the direction this new voice is coming from. When he sees who its attached to, he smiles a little bit.

"Ah, you must be my darling Rias' newest pawn. Issei Hyoudou, yes? Rias, you haven't told him about me?"

Curled into Riser's side, cuddling close, Rias Gremory looks up into his questioning eyes with a lewd sort of smile on her face.

"Ah, well... I was getting around to it."

Then she glances over at Issei and lets out a small giggle.

"Issei, this is Riser Phenex. He's my fiancé. We're getting married very soon, so make sure to be ready for the wedding with your best clothes~"

Seeing the despair on this Issei kid's face is a bit amusing, even though Riser doesn't really consider himself a sadist or anything like that. Really, he's just a male who likes the female form in all its different shapes and sizes. Rias' shape and sizes definitely fit into that. With one arm already around his fiance's shoulders, Riser slides his hand down a bit, under her arm, and reaches around her back to grab her far tit, groping it most blatantly and openly, right in front of her pawn.

Issei's eyes widen in anger, and his face goes an interesting shade of red as he looks like he's about to explode. But before he can say anything, Rias cuts him off with a wanton, heartfelt moan, that causes Issei's attention to shift right back to her, his face falling again as the anger flies right out of him in the face of his Buchou's true... nature.

As Riser casually molests his fiancé right there in the middle of her cute little clubhouse, Rias moans some more before collecting herself and leaning forward, looking Issei right in the eye.

"Issei..."

"Y-Yes, Buchou?"

"Get out."

"... Yes, Buchou..."

Riser watches Hyoudou leave the room in silence. As soon as the young man is gone, the Phenex devil chuckles somewhat, looking down at his fiancé with a cocked eyebrow, still groping her even now.

"Have you been playing with that poor boy's emotions, Ri?"

Rias Gremory has the lewdest, most perverse smile on her face as she looks up at him.

"Maybe~ I might have snuck into his bed a few times while completely naked. Just once or twice, you see."

Rather than get angry or anything like that, Riser laughs. Unlike Issei, he knows Rias very well. After all, they grew up together, after a fashion. They were part of a group commonly referred to as 'Pillar Kids', and while their generation was woefully small, leading to the need for more and more reincarnated devils in the first place, it did give them all a sort of... tight-knit feel. Of course, some of them had grown up to be bad eggs that the rest of the group didn't bother associating with anymore. But he and Ri had always remained close.

After all, Riser understood his fiancé quite well. She was a slut, and in a way, so was he. But of course, it was less tolerable for a female devil to be a slut than a male devil. So much less tolerable in fact that the male devil would never actually be called a slut, even if that was exactly what he embodied. And Riser certainly embodied sluttiness... so long as he was in control. His peerage... he had quite a lot of fun with them, fucking them on the daily, playing with them to his heart's content.

Poor Rias, however, was expected to keep herself pure until their marriage. That was half the reason they'd moved up the ceremony so that it would take place in a month rather than years down the road. It had been Rias' idea to do so, and yet, even now, with it so close, she couldn't help but yearn for more. If she'd done more with this Issei kid, well... the magic of the contract would have recognized her infidelity and dissolved the engagement. That was all Rias had to do, really. Let Issei fuck her, even once, and she'd be out of any obligation to him, and so would Riser. But of course, she would have to deal with the censure of not only their families, but the entire Underworld if she did that.

Meanwhile, Riser could fuck whoever he wanted, because the contract wasn't concerned with HIS 'purity' nor his infidelity. It wasn't fair, it was downright sexist even... but that was the way the world worked, it seemed. Still, Rias could have gotten out of it, and they both knew it... Riser wouldn't have even been one of the ones to censure her for it. But she didn't, because...

"He's not the one I want, Riser. I want... you..."

Not for the first time, Rias is coming onto him, practically draping her voluptuous body across his front, as he slides his hand down from her tits to her ass, groping and squeezing it as she practically kneels on the couch cushion in order to look him in the eye and press her tits into his chest. Meanwhile, Riser is extremely casual, lifting an eyebrow and just smiling at Rias.

Because yes, this is who Rias Gremory, Heiress to the Gremory Clan, truly is. She's a power-hungry slut, enamored with the financial power that the Phenex Tears his clan is known for represents. But to be fair, Riser is in turn just as enamored with the actual magical power that her Power of Destruction represents. He does want that for their children... but at the same time, he just smiles softly and shakes his head, rebuking Rias' advances then and there.

"Not until we're married, Rias. What would our parents say?"

Not for the first time throughout their engagement, Riser shoots Rias down. The fiery slut is all over him every time he visits, but he's never once actually fucked her. That's the funniest bit... they could fuck, and the contract wouldn't view it as infidelity, because Rias would be submitting to her lord husband in the process, or something archaic and misogynistic like that. So yes, they could fuck... but so far, Riser hasn't taken the bait, despite how delicious and fat-chested it is.

Whining in disappointment, Rias pushes off of Riser's chest, bringing her arms together in a way that squishes her tits inwards as she gives him her best puppy dog pout.

"But Riiiiser! The ceremony is less than a month away at this point! Surely we can have SOME fun..."

Still nonchalantly groping Rias' ass, much to her enjoyment and without a single complaint from the slutty red head, Riser inwardly reflects that he IS having fun. Outwardly though, he just smiles and looks down at his crotch, where his bulge is quite evident.

"If you must, you may suck me off, Rias. But no more than that."

The Crimson-Haired Ruin Princess practically teleports, disappearing from the couch and reappearing on her knees as she grabs HIS knees and jerks his legs apart, before hungrily attacking his button and zipper, extracting his cock from his pants in no time at all, and practically inhaling him down her throat. Riser groans as he places a hand atop Rias' head, sliding his fingers through her locks, not quite gripping down yet, just... enjoying her technique.

They've been doing THIS for as long as he can remember, for as long as its been... appropriate. Ever since that first time when she'd come to him and coyly asked that he fuck her, now that they were engaged, and he, seeing an opportunity, had refused on moral grounds, before offering this as an alternative.

Rias hadn't been so sure of oral sex at first, but as it turned out, she was slutty enough that having her face used like an onahole turned her on immensely. Even now, she was beginning to choke HERSELF on Riser's cock, just trying to deep-throat him.

"Hulghk... Hulghk... Hulghk..."

Chuckling, Riser turns away from the cat girl and leaves her to her recovery, finally looking to Akeno Himejima. By this point, the Priestess of Thunder has straight up removed the fetish gear that Rias had supplied her with. She's completely naked, and currently in a crabwalk pose, holding herself up on one hand and fingering her cunt and frigging her clit with the other, pointing herself right at him as she squirts her pussy juices all over the floor, not for the first time if the puddle of fluids beneath her is any indication.

She looks almost manic as she watches him approach, her face even more lewd than Rias' has ever been before, her eyes wide with avarice and lust and her tongue wagging out of her skull in blatant excitement. Riser's cock is full mast again by the time he stops in front of her, but rather than falling upon her, he stays where he is and watches her for a moment. Only when she opens her mouth to say something, likely to beg, does Riser cut her off with a smile and a sharp hand motion.

"Stand up."

Akeno hastens to obey, and he imagines she'd do almost anything he told her to do at this point, just for a chance at his cock. Rias really knew how to pick them, or maybe she'd simply infected Akeno and Koneko with her sluttiness over time, unconsciously reshaping the females of her peerage to be as needy and horny and slutty as she herself was.

Either way, Riser isn't going to pass up this chance... but after seeing how Akeno acts, he's decided he's going to have some fun with her. Smirking, he cocks his head to the side as he looks her up and down. Meanwhile, Akeno trembles with emotion, with need.

"Is there a bedroom here, Himejima?"

Blinking at the question, Akeno takes a moment to process it through the haze of wanton desire clearly hovering over her thoughts. In the end though, she nods hesitantly.

"Ah... y-yes?"

Smirking, Riser gestures.

"Lead me to it."

Akeno does as she's told, and soon enough they're standing in a bedroom. Certainly odd for an Occult Research Club to have, but not so odd when you knew that the ORC was just a front for a devil heiress and her peerage. Sometimes, you just needed an extra place to sleep at night. Regardless, it's perfect for Riser's purposes.

"Pull back the covers and lay down on your back for me."

As Akeno does as she's told, Riser strips out of his clothing as well. Only once he's naked does he move... and when he moves, he moves towards the lamp that Akeno turned on when they first came in. Flicking it off, Riser climbs onto the bed, and before Akeno can protest or anything like that, he pulls the covers back over them both. Before she can try to do anything with her hands, Riser grabs them both, lacing his fingers through them and pulling her arms up to either side of her head.

It takes only a second for the eyesight of devils to adjust in darkness, and once it does, Riser finds himself looking down into a distinctly confused and nonplussed Akeno's face. He grins, even as he presses his cockhead up against her pussy lips.

"W-What... what are you doing?"

Riser just grins wickedly.

"Isn't this what you wanted? Lights off, under the covers, holding hands, in the missionary position. Don't worry, I know it's your first time Himejima... I'll go slow."

Akeno opens her mouth to protest, but Riser just covers it with his own and slowly begins to push in. Inch after inch, he takes Akeno Himejima, just as he did Rias and Koneko before her. But it's not the same at all, and that's on purpose. After seeing just how much of a monstrous slut Akeno is, even compared to Rias... well, Riser can't help himself. He has to tease her. So that's what he does. He doesn't fuck Akeno like he did Rias, he doesn't RUIN her like he did Koneko. He makes love to her, even though they aren't the ones getting married, even though they're not actually lovers, and are barely acquaintances at that.

He can practically feel the steam raising off of Akeno's face and coming out of her ears as he slow-fucks her for the next fifteen minutes, before she FINALLY reaches an orgasm. Only then does Riser pull back from her lips, pulling away from her gasping mouth as he stops wrestling her tongue into submission. Eyebrow raised; he smiles down at her expectantly.

Akeno takes a moment to gather herself, before finally speaking.

"Y-You... you b-bastard..."

Riser just laughs, barely bothering to act surprised or confused, though he still asks her what's wrong.

"What's up, Akeno? Am I doing it wrong?"

"Y-YES! Fuck... fucking fuck me! D-Don't... stop with all this lovey dovey crap and TAKE me, you bastard!"

Riser hums, and then reaches over and turns back on the lamp. Then, he raises himself up, letting the covers fall off of his back and expose both of their naked, sweaty bodies. Finally, he lets go of Akeno's hands and reaches back to grab her by her ankles... before promptly folding her body up and slamming down into her in a mating press.

Akeno's face immediately ahegaos under the sudden feeling of his cock buried so deep inside of her, far deeper than he was going before. Not letting up for even a second, Riser proceeds to give the slutty, big-tittied babe exactly what she wants, pounding into her in the mating press position for a nice long while. Compared to the first orgasm that took fifteen minutes of excruciating (for her) lovemaking to arrive, Akeno is climaxing her brains out again and again soon enough, her pussy walls clenching and squeezing down around his cock as Riser fucks the Priestess of Thunder harder and harder.

In the end, he batters his way through her cervix just like he did Koneko, though the position their in doesn't really allow for him to bulge up out of her belly in the process. He still fucks her womb just as hard as he fucked Koneko's, and Akeno screams about how good it feels, how he's fucking her heart directly, how she doesn't want him to ever stop and how he's ruining all other men for her forever with this.

Typical slutty stuff, and Riser is sure if she finds another guy with a dick his size, Akeno will happily jump on it. She's a slut, and that's what sluts do. He doesn't mind overly much of course, after all, he's a slut too, and she definitely won't be the last woman he fucks, not even today. Regardless, Riser takes Akeno to pound town, given that he's cum twice before and it takes longer for his third release to arrive.

By the time he finally cums inside of Akeno, by the time he creampies the slutty Priestess of Thunder and fills her womb with his seed just as he did to Rias and Koneko, Akeno's eyes are perpetually rolled back in her head, and she's clearly in a pleasure coma of her own, all of that teasing combined with the rough, hardcore fucking the slut received afterwards clearly too much for her.

Smirking, Riser pulls out of Akeno and gets off the bed, turning around just in time for Rias to stumble into the room.

"Ah, good. Kneel, darling. Your servants proved to be a bit messier than expected, and I need you to clean up for me."

Rias' eyes sparkle with delight as she happily obeys, still dressed in just the skirt of Kuoh Academy's uniform, her tits on full display and available for her to grope and squeeze and pinch, even as she takes him into her mouth and begins to lovingly and most importantly, sluttily clean him up. Riser chuckles down at his slut of a fiancé, placing one hand atop her head and petting his fingers through her hair.

He was glad that Rias had grown up to be just like him, in the end. He couldn't imagine what an engagement between them would have been like if they weren't both huge, unrepentant sluts. Luckily, he didn't have to. They were perfect for each other... a match made in hell.

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