2 Rias Gremory Pt. 1

Back in the present, Ddraig was brought out reveling in her past memories by something happening in the real world. Ddraig had a nice bird's eye view in Issei's mind; set up by her lovely Master himself when he'd first learned how to properly enter his mindscape. As such, she could watch him all day long if she wanted to. Most of the time she did, when she wasn't contemplating shit, getting lost in the past, or being pulled out into the real world for him to fuck.

Of course, Issei Hyoudou wasn't just a pervert. He was also a total player. The kind of man who, despite his sometimes unsubtle deviancy, could talk the panties off of any girl his own age and even most women older than him. Thus, Issei Hyoudou got a LOT of pussy. It didn't help that he went to what had originally been a private all-girls school. Kuoh Academy was essentially ninety percent young impressionable women.

And Issei made quite the impression in everyone he met, both physically and mentally. Because of this, most of his conquests weren't really worth watching beyond entertainment value. Watching the captain of Kuoh Academy's gymnastics squad desperately blow Issei on the off chance that he would MAYBE think about possibly attending her next meet IF he had time got old after the twentieth time she offered to do it. He'd never gone to any of her meets and at this point she was barely maintaining the pretense that THAT was why she was still sucking his dick every time.

Hell, the last time she'd just asked him to speak to her in private, pulled him into an abandoned classroom, and dropped to her knees to suck him off. Once he'd cum all over her face, the girl had stood up with a smile under the facial and waved goodbye to him, saying she hoped to see him again soon. No mention of her next meet.

But Ddraig was getting distracted yet again. What was happening RIGHT now in the real world WAS actually interesting. The dragon girl found herself leaning forward and licking her lips as she watched Rias Gremory of all people approach an uncaring and apathetic Issei. The beautiful crimson haired top heavy devil clearly wanted something from him, just like Ddraig had told her master all that time ago. This would be Issei's first encounter with the forces that Ddraig had been preparing him to face.

The Red Dragon Empress' face split into a grin as she watched on. This was going to be good.

-x-X-x-

Rias Gremory was a young lady who was used to getting what she wanted. It would probably be fair to say she was spoiled. It could be argued that Rias had come out reasonably well despite said spoiling, but the fact that she had grown up spoiled was indisputable. If nothing else, even setting aside her parents doting on her as the younger child, her older brother's constant interference in her life in an effort to better her circumstances no matter the costs, had totally and utterly spoiled her.

Case in point, Rias Gremory had yet to actually obtain a peerage member that hadn't been simply handed over to her, sometimes literally. She'd stumbled into her meetings with all of her 'precious' family and she'd never truly had to fight for any of them. They'd been given to her by fate and circumstance. So, approaching Issei Hyoudou, Kuoh Academy's resident player and teen heart-throb now, it was new ground for her.

But the young man's power and presence was unmistakable, as was his effect on the Academy. Rias and Sona had had a total of TEN private meetings between just the two of them in the last three months that were all focused on the charismatic boy. Her friend was always so torn about the young man. On the one hand, Sona felt the same power that Rias did. And she also noticed Issei's good looks. As a member of the Sitri, she lusted after Issei. Though Rias knew that Sona thought she'd managed to keep such impure thoughts a secret from her friend. Because on the other hand, Sona was a very strict, straight-laced young woman. Rumors of Issei's behavior infuriated her and the only reason he escaped punishment was a lack of evidence and witnesses.

Kuoh's student population was more than happy to gossip about the male's prowess in matters of intimacy, but when directly confronted by a member of the student council, the girls who bragged about taking him on first hand clammed up, completely unwilling to incriminate their precious Issei. In the end, a frustrated Sona had told Rias in their last meeting that if the red head did not make a move to bring the troublemaker into her peerage, Sona WOULD, just so she could try to curb the young man's scandalous deviant behavior.

Rias had rather thought the faint blush on Sona's cheeks showed that her friend was more than likely interested in very specific forms of punishment and the red head was wondering just who would be curbing who in such a joining. But in the end, she knew what she wanted. She wanted Issei Hyoudou to join HER peerage, not Sona's. She wanted that power that she and Sona felt in HER grasp and she was willing to do quite a lot to get it.

Such as approach the young man while he was alone on the roof of the Academy eating lunch. Licking her lips, Rias stepped up behind Issei and cleared her throat, causing the brunette to slowly turn his head and look over his shoulder at her. The lack of interest in his eyes left Rias a bit surprised.

"Oh. It's you."

Rias flushed red in a mixture of embarrassment and just a bit of arousal at the effortless dismissal. Damn it, how dare he react so coolly to her presence! She might not have made much of a big deal about it, but was she not one of Kuoh Academy's Two Great Ladies alongside her Queen, Akeno? Gritting her teeth, Rias finally spoke.

"Issei Hyoudou! I would like a word with you!"

A sigh escaped the young man's throat and he slowly turned to face her. A single eyebrow lifted in response to her words.

"Yes?"

Trying to control her blush, Rias bit her lower lip briefly, eyes darting back and forth as she worked out what she was going to say. Of course, she'd already done that beforehand, but Issei Hyoudou had this WAY of derailing everything almost effortlessly.

"Alright, let's start slow. I… am not a human Hyoudou. I am a Devil and I want to offer you the chance of a lifetime."

There is a disturbing lack of surprise on Issei's face at her revelation. Rias frowns, wondering if he doesn't believe her. Then, he speaks and dispels such silly notions.

"I already know you're a Devil. Just like the Student Council president and the Student Council itself, as well as the Occult Club that you head. They're made up of yours and Sona Sitri's peerages are they not?"

It seemed that instead of him, it would be Rias who would be shocked speechless by the revelations of the day. Issei knew everything, seemingly effortlessly. She didn't understand. Perhaps… perhaps this was his power? Rias and Sona had discussed the young man's overbearing presence in detail (perhaps too much detail) but in the end they'd both agreed that he was still one hundred percent human to their senses. Still, there was also the slightest tinge of dragon in his aura.

"I… yes. How did you know?"

It seemed silly to try and deny it. Issei spoke with such confidence, such conviction. And he was right, completely and utterly right. Slowly, a smile spread across Issei's face and he stepped forward, causing Rias to attempt to both shrink back and lean forward at the same time. The end result was a sort of vibration she couldn't quite stop as he entered her personal space and looked down at her. Issei was tall and as she looked up into his eyes, Rias found herself licking her lips, wanting nothing more than to kiss the man's lips. They looked very kissable, this close up. Especially when they moved as he began talking, answering her question.

"I know a lot of things Rias Gremory. Least of all is the information I have on you and Sona. You're small fry in the end. Still, I wouldn't wish to be rude. Go ahead and make your offer of a lifetime."

Suddenly feeling completely and utterly outclassed, Rias both felt doomed to fail but also more sure than ever that she WANTED Issei in her peerage. If she hadn't been spoiled as was outlined earlier, perhaps Rias would have given up in that moment, realizing the futility of trying to put this magnificent man under her control. The red head would have regretted it for the rest of her life, but she would have remained her own person if she'd simply stepped back and left Issei standing there on the roof in that moment.

She did not; such was her confidence that in the end she would get what she wanted. Instead, the Gremory Heiress stiffened her upper lift, clenched her jaw and looked up into Issei's eyes as the young man smiled at her.

"I would offer you a place in my peerage Issei Hyoudou! I can assure you, neither I nor Sona are 'small fry'. We are both young devils yes, but we're pureblood nobles, each of us. One day we will rule parts of the Underworld as our families have always done and those in our peerage will have every chance at advancement. Someone like you, if you joined me now, could become a High-Level devil and eventually you would gain a peerage of your own, so long as you stuck by my side. I'm a rising star Issei Hyoudou. You'd do well to take advantage of my generosity now."

Issei grinned salaciously at that, even as Rias completely missed the double-meaning in her own words. She was far too focused on Issei's response to truly understand the fact that she'd just offered herself up to him on a platter. Though to be fair, it wasn't like Rias wasn't willing to have sex with the young man. She'd certainly fantasized about it enough. But unfortunately the Gremory Heiress wasn't allowed to give away her virginity, due to her engagement.

Of course, Issei did not know that and he would not have cared if he did. Instead, the bearer of the Boosting Gear simply leaned in close, smiling down at Rias.

"An intriguing offer. I suppose I could be persuaded to join your peerage. But while all that future stuff sounds nice, I'd like something more tangible, more immediate."

Rias blinked at that, looking at him owlishly and waiting impatiently for him to get the point. Issei's smile widened, taking on a predatory glint.

"Here's the deal Rias. I get a lot of head. Girls worship my cock with their tongues and their mouths and their tight throats so often that honestly, it's all bled together at this point. Barely anyone can give me a blowjob that's actually memorable anymore. So, do that for me and I'll join your peerage."

The crimson haired woman processed Issei's words, his request, and promptly bluescreened for a long moment. He wanted her to suck his dick? Rias.exe rebooted remarkably fast and soon enough the beautiful buxom young lady was mentally talking herself into it as she looked down at Issei's chest, explaining to herself why it was the perfect exchange and why she could totally get away with it because she wasn't ACTUALLY giving her virginity away or anything, just sucking her first dick.

Ultimately, through an amazing lack of self-awareness and a whole lot of denial, Rias was convinced that this was an excellent deal and she was going to easily come out on top. A smirk spreads across the devil's face as she looks up into Issei's expectant eyes.

"I agree! I'll suck your dick, and then you'll become a member of my peerage and acknowledge me as King! No, more than that, you'll call me Buchou okay?"

Issei raised both eyebrows at that, but the crimson haired woman was far too fired up to really realize how silly what she'd just said was. She was going to kneel down and suck his cock and then SHE would be his King? It was laughable, but Issei was interested in seeing just how Rias would go about it, so he simply nodded and kept right on smiling. The girl nodded back, a determined focused look spreading across her face and then she dropped to her knees right there on the rooftop.

He let her do so, watching as she came face to crotch with him and slowly reached out to undo his belt. Her fingers where shaking despite her seemingly confident and boisterous attitude, and Rias swallowed a lump in her throat as she put one of her hands down Issei's pants and into his boxers so she could grip his member in order to pull it free and begin fulfilling her end of the deal.

The thing she latched onto felt more like his thigh than his shaft for a moment, but then Rias felt it pulsing and even growing in her hand and she realized that Issei was fucking HUNG. Gulping again, the crimson haired beauty slowly withdrew Issei's shaft from its tight confines, ultimately allowed his half-hard cock to smack her upside the head when it finally sprung completely free.

Gasping at the sudden contact, Rias inadvertently breathed in some of the boy's draconic musk and her pupils immediately dilated as she practically melted right then and there. This was the moment that Rias Gremory, Heiress to the Gremory Clan, truly fell to Issei Hyoudou. Before now, before this instant in time, there was still a chance that Rias could have escaped with at least some of her dignity intact, always longing for Issei, but able to move on and live a productive life without his presence.

Now though, such a future was a pipe dream. In the span of moments, Rias is entranced by the massive member in front of her.

"It's… so big."

Issei chuckled in response, his hand suddenly coming down to rest atop Rias' head. His fingers curled into her crimson locks and he gripped firmly but for the moment, gently.

"I suppose that I've never had a girl trying to stare me to an orgasm before. It's certainly a unique way of blowing me Rias, but somehow I don't think it'll get me to cum any time soon. Let's get this show on the road alright?"

Rias, still staring at Issei's dick, simply nodded dumbly and leaned forward, her hands wrapped around the length of his member and her tongue slipping out of her mouth to flick at the tip. She began to lick his cockhead while giving him a handjob, the proud girl's first contact with a man's shaft. But Issei didn't care about the virgin's lack of experience. What he cared about was the fact that her lack of skill, combined with her hesitance, was frustrating him more than it was getting him off.

A low growl left the young man's throat and Rias' eyes darted up to meet his. Issei's grip in her hair tightened and he spoke in a guttural tone as his huge pulsating member twitching in her grasp.

"Open."

A single word command, yet Rias followed it immediately, her lips parting and allowing his shaft to pass through them more easily. Her tongue ran along the underside of Issei's cock, even as the young man pushed inch after inch into her mouth until he hit the back of her throat. She was only halfway down his length as she coughed and gagged a bit at the feeling of something pressing against her tonsils.

Issei held her there for a moment and Rias made sure to do the best she could, licking at his member with her tongue and making sure her lips were suctioned down around his girth. But it still wasn't enough for the young man that contained the soul of a dragon. He wanted more, as all dragons do. He wanted more power, more control and most of all, he wanted more of the young slutty maiden before him, desiring to take everything from her as she prostrated herself and offered it all up.

And so, much to Rias' surprise, Issei wasted no more time. He pulled back slightly and then thrust forward, and the tip of his dick went straight down Rias' throat, causing her to gag and choke around his member as he did it again and again and again.

"Gagkh! Gagkh! Gagkh Gagkh Gagkh Gagkh Gagkh!!!"

Rias' eyes widened as her face hole was the subject of a brutal pounding, Issei roughly fucking her throat and not letting her get a single breath of fresh air as he did so. The crimson haired beauty's eyes began to flutter shut but despite the lack of oxygen, Rias wasn't afraid. Instead, she was turned on. Massively so in fact, to the point that the Gremory Heiress reached down with what little strength she had left, lifted up her skirt, and stuffed both of her hands down her panties in order to touch herself as Issei face fucked her as hard as he could.

The young woman continued to choke and gag and her vision began to turn black as Issei's cock went deep down her esophagus again and again. The draconic young man was relentless in his onslaught, and he had no desire to stop as he jackhammered into the young devil's throat. Ddraig had told Issei of the enemies he would face. The Red Dragon had even gone so far as to warn Issei about the devils in his midst.

But in this moment, Rias was nothing but another hole to be fucked. He hadn't yet decided if he would truly join her peerage or not, but it didn't truly matter right now. Because right now, Rias was simply another slut, on her knees, taking his cock deep down her cunt-throat. Of course, a lack of air will get to anyone eventually, even a devil.

Slowly but surely, Rias' hands fell away from her sopping wet cunt and hung limply at her side. Her rapidly fluttering eyes drifted shut completely, and she actually passed out on Issei's member as it continued to drive down her throat. When she woke again, it was because Issei had pulled completely out of her mouth and air was finally returning to her lungs. Rias came back to full awareness just in time to feel the young man's white hot seed as Issei made sure to cum all over the red head's face.

Realizing what he'd done, realizing how he'd humiliated and degraded her, Rias came on the spot, eyes going wide as sticky cum dripped down from her forehead, her entire body shaking and her pussy juices forcefully expelling onto her panties beneath the skirt she was wearing. The Gremory Heiress was struck dumb, sprawled as she was with her legs under her, her face covered in cum and her girl juices dripping through her panties and onto the roof of the Academy.

Issei's chuckle was what finally brought Rias back to the land of the living, her glazed over eyes getting a bit of life back into them as she looked up at him. Blushing deeply and biting her lower lip, Rias could see nothing but a man she would gladly submit to right here and right now, if it meant receiving more of that brutality. Now more than ever Rias wanted Issei in her peerage. Not because she still wanted to tame him or make him acknowledge her as his King, but because she wanted him in her bed every single night for the rest of her life.

More than that, she wanted to be in HIS bed for the rest of her life. She wanted him to take her and make her his, but she couldn't dare ask for it, not with her responsibility as Gremory Heiress hanging over her head. Instead, Rias asked the next best thing. Her voice was raspy as she spoke, her throat sore, but it had to be said and she had to know the answer now.

"Well? W-will you join my peerage now Issei?"

Issei peered down at her in a considering fashion and Rias found herself pushing out her bountiful chest in an effort to entice him further. She swallowed hard, licking her lips and awaiting his response.

"Tell me Rias… did you climax, when I came on your face?"

The question, rather than a straight answer, threw Rias for a loop. Her eyes widened and she blushed an even darker shade of red than her hair color, her lips sealed. But of course, Issei saw the truth in her eyes, or perhaps he saw it in the small puddle forming between her legs. The brown haired boy laughs and he laughs hard.

"Hah! You did! Oh my god, I can't believe it! Rias Gremory cums from being face fucked! What a total and utter slut!"

And to her shame, those words brought her pleasure. Rias' body shuddered as she went through another mini-orgasm, solely from Issei's words. She tried to hide it, but he saw and she knew he saw when he suddenly stilled, the laughter gone. He looked down at her with an expressionless face and the crimson haired devil was about to ask what he was thinking when he moved before she could get the first word out.

Rias yelped as Issei forced her to her feet, frog marched her across the roof and then forcibly pinned her against the safety fence that sat on the edge. Below them Rias could see the Kuoh Academy's main courtyard, with students of all ages and genders passing by back and forth on the way to their next class. The red head whimpered but stifled the cry that tried to leap free of her mouth when Issei reached around her front and practically tore her blouse apart to reveal her big tits, now only barely restrained by her bra.

In full view of everyone down below, Issei began to knead and grope Rias' mammaries. All the students had to do was look up and they would see her exposed front. Even worse, Issei removed one hand from her chest and lowered it below her waist, grabbing onto her skirt and hiking it up to reveal her panties, a tasteful red piece of lingerie that matched her bra in color and complexity.

"I-Issei, what are you d-doing?!"

Rias finally found the strength to talk, to react to the domineering movements from the young man holding her in place. His response was to press her harder against the fence, the chain-link squares digging into Rias' thankfully covered bust rather painfully.

"Whatever I want slut, what the fuck does it look like I'm doing? Do you want me to join your peerage?"

Swallowing hard, Rias managed a nod. Yes, she did. Even after all of this (ESPECIALLY after all of this) she wanted him to join her peerage, no, more than that, she NEEDED him to join her peerage. And suddenly, Rias needed him to know that too. Speaking in a whisper shout so as to avoid alerting any of the students passing by down below, Rias made her feelings known to the young man who had her pinned.

"Yes! Yes I want you to join my peerage! Please Issei, please let me prove myself to you! Let me prove myself worthy of your love! Take it, take me! Take everything Issei!"

Her engagement and her duties as heiress forgotten, Rias Gremory laid her soul bare to the man who had so utterly changed her in such a short time and begged him to just fuck her already. And Issei obliged, snorting derisively and in one easy moment, pushing her panties aside and shoving his hard thick cock into her sopping wet cunt from behind.

Rias' eyes widened and her lips opened up while her lower lips spread around his cock, but luckily Issei was prepared. His hand closed over her mouth and muffled the scream of pleasure that emanated from it a moment later. He paused briefly, having taken Rias' virginity without hesitation but kind enough to give her just a second to adjust.

And then Issei Hyoudou began to fuck her and it was everything Rias had ever hoped and dreamed for, ten, no, a thousand times better than her greatest fantasy! His long powerful thrusts into her needy cunt pushed her up against the fence each time, but Rias could care less. Her mouth was open as a continuous moan left her lips. Very briefly and very blasphemously, Rias momentarily wondered if this was what Heaven was like. If this was, she could finally understand why some humans were simply unwilling to make a deal with a devil in the hopes of going there.

The red head's mind snapped as she came for the first time around Issei's cock, mostly because it was far from the last time and once the damn broke, Rias Gremory was climaxing nonstop as Issei plowed her from behind. Her eyes rolled back in her head and her tongue lulled out of her skull as Issei hooked his fingers into the side of her mouth rather than cover it up entirely.

Rias Gremory was the picture perfect image of ahegao in that moment, completely and utterly lost in the pleasure of Issei's brutal pounding of her once virgin cunt. She clawed at the chain-link fence before her, but ultimately gave up, her arms falling limp at her sides and her body simply shaking and jiggling in time with Issei's powerful thrusts up against her backside.

Eventually, Issei came. Rather than being the final straw, which for Rias Gremory had long since passed, Issei's release was actually a bit of a calming force for the beautiful red head. Once he'd filled her with his seed and pulled his amazing cock out of her quivering quim, Rias could finally think straight again. She slowly sunk down to the ground, leaning against the fence for support and gasping for air. Issei stood over her, waiting. For a belated moment, Rias wondered what the young man was waiting for.

Then she realized. Slowly, very slowly, Rias shuffled herself around and looked at Issei's filthy member. Without having to be told to, the crimson haired beauty, a pureblood devil, heiress to one of the seventy two pillars, leaned forward and began to clean the cock of her master with her tongue. The transition of thinking of Issei as a potential recruit to thinking of him as her lord and master, the love of her life and the center of her world, was completely seamless.

Rias, utterly mind broken in the same way Ddraig had been by this point, simply lavished praise along her Master's shaft until finally he grunted and pushed her away. Then, the two of them got dressed and she led him down off the roof, ecstatic as he allowed her to show him the way to the Occult Research Club's base of operations.

-x-X-x-

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