A New Dynamic (High School DxD) (Patreon)

Poll Winner 

Themes: Exhibitionism, Master/Pet, Slutty Sex   

Summary: Based on this image. Rias was already developing feelings for her perverted Pawn before he beat Riser into a pulp for her. Once that happened, the gorgeous red-head just couldn't hold back her inner slut any longer. She gives herself to Issei, wholly and utterly, and BEGS him to slake his most depraved desires on her. So far, that's apparently limited to perverted walkies at sundown, but Rias hopes to prod him into more devilish activities as time goes on. 

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The sun is setting, as the two of them step out of the Occult Research Clubhouse’s backdoor and begin making their way down the street. Even as they’re walking, Issei finds himself wondering if this, all of this, is really all right. He feels… he feels like a dog who’s been chasing cars, only to finally catch one. And then, after he caught that car, it decided to submit to him completely and utterly, in a very sexual manner.

… Okay, so maybe that metaphor didn’t precisely work that well in this situation. But all the same, it was a bit of a conundrum for the perverted would-be Harem King. He’d spent so long lusting after beautiful women, dreaming of having a harem. Suddenly, it felt like he was getting close to accomplishing his goals, and Issei really wasn’t sure how to feel about that.

Maybe he should have been leaping into it with both feet, but it was hard. He kept waiting for the other shoe to drop, even though deep down, he knew it never would. He’d beat Riser, he’d defeated him and freed his Buchou from her arranged marriage. Rias Gremory was now free to love and be with whoever she wanted to love and be with. That was what mattered.

It was just that, while Issei had hoped that it would be him she wanted to be with, he hadn’t dreamed in a million years that it would actually happen this way. Sure, Rias had taken to sneaking into his bed and sleeping beside him naked. But that was… okay, so maybe Issei needed to face the facts. Glancing down at the chain leash in his hand, the leash that leads up to the collar around Rias Gremory’s neck, the young pervert swallows hard.

Rias catches him looking and smiles back at him encouragingly, even as they walk along. Technically, she’s fully dressed right now. Except, she’s not wearing a bra, and he can see her hard nipples poking through her blouse. She also has her blouse partially unbuttoned, showing off a grand expanse of her cleavage. She looks amazing, mouthwatering even, and Issei is rock hard right now, even as they walk along.

When Rias had told him that she wanted him to do whatever he wanted with her, she’d begged him to slake his most depraved desires on her. So… this was what Issei had ultimately come up with. Oh sure, he had a lot more depraved desires than this in the back of his head. The things he would do to Rias if he was sure there was no consequences…

But he wasn’t sure. Not just because Rias might take offense, but because of her brother, the overwhelmingly powerful Satan. Sirzechs might have been on Issei’s side when they were both aiming to free Rias from Riser, but what if Issei were to treat Rias too poorly? Then what might the Satan do?

This much was fine though, right? Them going on a walk, with Rias collared and her leash in his hand. With the sun setting on the horizon, there weren’t many people out and about. Those who had to be up early in the morning for work were already at home, if not already in bed. Those who would constitute the city’s nightlife weren’t quite all out in force yet.

It meant it was just the two of them, as they walked down a street together. And that… that made Issei think about all the things he could do to Rias, in this situation. She wanted him to, right? She’d begged him to. She’d submitted to him, wholly and utterly…

Swallowing thickly, Issei tugs on the leash experimentally as he turns down an alleyway between two office buildings. Rias doesn’t hesitate to follow him in, in fact the growing smile on her face makes it clear that she’s hoping he’ll use her as she’s suggested. Well, she might just be about to get her wish.

He’d gotten this idea of doing a perverted walkie from a hentai he’d watched a few months back, before he’d been reincarnated as a Devil, before all the craziness with the Fallen and then Riser had come to pass. And so, Issei continued to draw from the hentai he vaguely remembered, curious to see how Rias would respond to his commands.

Turning to her, he clears his throat and speaks clearly and concisely.

“Sit. Beg.”

Licking her lips, Rias drops into a crouch. She looks up at him, this red-haired goddess that Issei still wasn’t sure he deserved, and she unbuttons her blouse the rest of the way. It falls to the sides easily as her absolutely massive breasts bounce free, each capped with an erect pink nipple that could likely cut diamond at this point.

Then, she reaches down and divests herself of her skirt next, pulling down a zipper and sliding it off of her body to reveal that she IS wearing panties. They’re a very sexy, very skimpy black pair of panties with the smallest little red bow right at the top of them. Sliding them to the side, Rias reveals her glistening wet pussy lips to him as she crouches there on her toes, resting her thighs back on her ankles.

Placing her hands behind herself, grabbing the heels of her shoes, Rias presents her entire body to him, showing off every inch of her gorgeous figure as she licks her lips and looks him in the eye.

“Please, sir. Please use your pet however you like. I beg of you Master, make use of my body to slake your demonic lusts.”

… Fuck, that was amazing. Any concerns Issei may have had are quickly fleeing in the face of the sheer lewdness he’s being confronted with. The boy is still a pervert at the end of the day! Stepping forward, Issei brings his bulging crotch closer, even as he pulls Rias forward as well by her leash, causing her face to collide with his bulge. 

She moans and rubs herself against his crotch, sniffing at it like… j-just like out of one of his hentai. Since when was this his life? How had he ever done enough to deserve something so amazing?

“T-Take it out.”

If Rias notices his stammer, she doesn’t comment on it. Smiling quite happily, she reaches for his pants with her fingers, and deftly unbuttons and unzips them.

“Yes, Master~”

His cock is out and in her hands a moment later. Issei’s breath hitches as she strokes his growing length up and down.

“So big, Master…”

Her murmur SOUNDS honest, but Issei really doesn’t know if she’s telling the truth or not. Is he big? He was about as big as the protagonists in most of the hentai he watched. He’d never really known if that was big or average though, since he didn’t really go for porn with actual real people in it. But now… now it was like he was starring in his own porno, and Rias was positively salivating over his cock as she stroked it up and down, crouching there in the alleyway, looking like sex on legs and dripping all over the ground from her exposed pussy.

“… Put it in your mouth. Ah, you can use your breasts too if you want…”

He tacks on that last bit almost as an afterthought, but Rias takes the suggestion to heart all the same. Wrapping her prodigious breasts around his cock to the best of her ability, Issei for the first time acknowledges that he must have a pretty big cock, because she can’t QUITE capture all of his length in her tits, and Rias has one of the biggest racks Issei knows about.

Once she’s got her titties wrapped around the lower half of his dick, the collared and leashed devil Heiress tilts her head forward and takes the top portion of his member into her mouth. She bobs up and down on his cock, swirling her tongue around his cockhead, moaning all the while and acting like it was the most amazing thing she’d ever experienced.

… She really was quite slutty, wasn’t she? Issei hadn’t truly understood before. It hadn’t been easy for him to come to terms with the fact that women could be… well, perverts too. Even with Rias sneaking into his bed at night, he’d made excuses and allowed himself to remain willfully ignorant to the truth.

Not anymore though. While it was obvious that Rias was at least choosy about who she was slutty with, it was equally obvious that his red-headed Buchou was a huge pervert. And that… that, Issei could work with.

Operating wholly on instinct, he reaches out with the hand not holding Rias’ leash and places it on top of her head. His fingers lace through her red locks before gripping tightly as he drags her forward along his cock. Rias’ eyes widen at that, her breasts falling away as she’s forced to deep-throat his member, but she doesn’t protest or resist. She takes it… and that, in and of itself, opens the floodgates.

“You’re my slut. You’re my fuck toy. You’re my bitch.”

As Issei hisses out each of those declarations, he forces Rias down his cock, gagging and choking her on his dick. In response, she moans and nods the best she can, her humming sending reverberations up his length that cause Issei to shudder in delight.

“… I want to fuck you now. Your virginity belongs to me, right?”

He pulls her off his cock at that, eager to hear her response. Part of him is afraid she’ll say no, but Rias just smiles up at him and nods.

“Yes, sir. My virginity is yours to do with as you please. You could even make a lot of money, selling it to the highest bidder.”

That thought causes Issei to frown and shake his head. His cock very nearly loses it’s hardness at the mere idea of someone other than him getting with Rias. Rias seems to realize she’s said the wrong thing, but before she can backtrack, he’s pulling her up by both her hair and leash, probably a bit more roughly than intended, and thrusting her up against the nearest wall face first.

“No! No, this body… it belongs to me. No one else touches you. Ever.”

“Y-Yes, Master~”

If Rias feels any discomfort from having her bare naked tits and hard nipples rubbed against the dirty brick wall, she doesn’t say anything. She just moans and mewls as he grinds her into the wall, while at the same time pulling her hips back and placing his cockhead up against her juicy pussy lips. Fuck, she’s so wet… he’s about to deflower his Buchou.

Before he can second guess himself anymore, Issei thrusts into Rias, taking her for the first time from behind. Nothing lovey dovey about this, he’s fucking her up against a wall in the middle of an alley, still holding onto her leash. And yet, the moment he’s inside of her, the moment he tears through her hymen, is the exact moment that Rias cries out and cums on the spot.

At least, Issei thinks it’s an orgasm. To be fair, this is technically his first time as well. But the way Rias’ cunt clenches down around his member, the way her fluids flow down the length of his cock as she shudders and spasms against the wall… it certainly seems like an orgasm. But then, why guess when he can just demand an answer?

“Did you just cum?”

Rias has to spend a moment catching her breath before she answers, but when she does…

“Y-Yes sir. Y-Your big fat cock made me cum, sir…”

… He can’t hold back after that. Holding onto her leash with the one hand and her hip with his other, Issei begins to thrust forward like a mad man. He certainly doesn’t feel altogether sane anymore. He’d spent so long fantasizing about this ideal reality, but even in his most delusional moments, he hadn’t allowed himself to believe it could come true.

And yet, here he was. Rias Gremory, one of the Two Great Onee-Sama of Kuoh Academy, was giving him her virginity. More than that, she was giving him everything. She was his to do with as he pleased, his to fuck and use to his heart’s content. With a lust filled growl, Issei continues to pound into Rias from behind almost violently, getting out years upon years of pent up aggression and lust.

Given his track record, how his first ever ‘girlfriend’ had outright killed him, maybe he didn’t need a girlfriend. Maybe, a fuck toy like Rias was perfect for him. Issei… Issei could get used to this. In fact, he was pretty sure he already was. As Rias cries out, pressed against the wall by his pistoning cock and cumming again and again around his member, Issei groans and buries his face in her hair, breathing in her scent as he claimed her for himself.

His. All his… and he was never going to let her go. With a sudden surge of strength, Issei pulls Rias back from the wall. He keeps on fucking her of course, but now it’s just him that’s holding her up as her knees knock together, her legs turned to jelly and incredibly wobbly. He wraps one arm around her front, grabbing her left breast with his right arm from across her chest. Groping and squeezing it, Issei is reduced to animalistic and primal growls and grunts as he thrusts into Rias’ welcoming, inviting, tightening cunt for the next several moments.

Finally though, he’s unable to hold back any longer. Finally, he cums inside of the beautiful red head, pumping his first load of cum into a woman. The fact that it’s Rias Gremory he’s filling and creampieing just makes it a thousand times better, in Issei’s book.

For a brief time, the two of them just stand there, both having to take a moment to recover and catch their breath as they pant heavily and noisily. Eventually though, Issei slowly lets go of Rias and pulls out of her, after making sure that she wasn’t going to collapse on him, of course.

When she goes to pick up her skirt and begin fixing her clothes, Issei stops her with a sharp tug on her leash.

“… No. We’re going to walk home with you like that. As you are now.”

With her blouse open and her skirt off and her panties still pulled to the side as his cum slowly leaks out of her freshly fucked, gushing wet pussy lips. To her credit, Rias doesn’t even hesitate to bow at the waist as she balls her skirt up in one of her fists rather than putting it on.

“Of course, Master. Lead the way~”

Issei can still hardly believe his good fortune. But… he’s finding it easier to accept with each passing moment all the same.