An Eye for an Eye (High School DxD)

A/N: An Eye for an Eye was originally written back in February of 2019. Posting it up now for people to enjoy!

Themes: Mind Break, Master/Slave, Marathon Sex, NTR

-x-X-x-

He was nervous, but then, who wouldn't be, given the circumstances? Really, it was all about how well one hid one's nervousness and lounging back with a glass of wine in one hand and a smug smirk on his face, Riser Phenex thought he was doing pretty damn well. Even still, he wasn't nearly as placid or calm as the being he sat across from.

Venelana Gremory, the Matriarch of the Gremory Clan, sits opposite with her legs crossed and her hands held in her lap, a soft smile on her face and something akin to pity or even apology in her beautiful violet eyes. Riser hated it. He hated everything about this. But he'd be damned if he didn't try to turn things to his advantage.

"Obviously, you've been wronged, child. Or I would not be here. It is the belief of Lord Gremory and I that you have been treated unfairly at every turn by our son and daughter. Things have obviously become untenable, and the original marriage agreement will never happen now, but that does not mean we cannot make things right. I assume you have something you want, or you would not have asked to be the one to meet with me. Please, tell me what it is the Gremory Clan can do for you."

Riser's heart is pounding in his chest, even as he bristles a little bit at being called a child. And yet… and yet the woman before him is thousands of years older. This is Venelana Gremory, formerly Venelana Bael, the eldest daughter of the House of Bael. He still remembered Rias' Power of Destruction well enough, and there was no doubt in his mind that the Gremory Matriarch would command even more control over such a thing.

Even still, he had indeed demanded, not asked, to be the Phenex representative at this meeting. The moment that he'd heard just who the Gremory were sending as their representative, he'd barged into his father's office and told the Lord Phenex what an affront it was that Lord Gremory couldn't even come himself and had to send his wife in his place. Then, he'd leveraged that to gain the right to take his father's place, as Venelana was taking her husband's.

Under normal circumstances, sending Riser, the third son, would have been an even graver insult. But it was he who had been insulted, he who had been victimized by the Lucifer and by Rias Gremory. It was he who had had his honor impugned upon, and he who had tried with all his might to protect the deal made between their two houses. Put bluntly, Riser knew that Venelana would not think twice about having to negotiate with him. At the same time, he had also been somewhat prepared for her to treat him like a child. Though outright CALLING him one was a step too far, in his mind.

"… You agree then, that I've been wronged. You agree that the Phenex Clan, and more specifically me, deserve to be compensated for this miscarriage of justice?"

Venelana's smile never shifts, her face never changes… but she does incline her head in acknowledgment of his words. Riser has to tightly control himself to keep from shaking, not in fear, but in anticipation.

"I have been denied my wife. And as you say, that marriage will never happen now. But that's fine. I don't want Rias, not anymore. I want you."

Finally, he gets a reaction. It's not necessarily a good one though. Venelana's eyes flash with something dangerous, even as her smile freezes in place on her face. Her entire countenance becomes frigid.

"Is that so?"

But Riser isn't going to be cowed now, not when he's come so far to try to make this happen. If he dies, he dies. He's tired of being yanked around.

"Yes. Unequivocally. Your daughter has insulted me at every turn. Your son has played favorites at the expense of my clan. My father has entrusted me with full bargaining power for these negotiations, as I'm sure your husband has done for you. The long friendship and alliance between Gremory and Phenex need not be broken over this… but if you do not agree to my demands, I cannot see how things will not crumble before our eyes… and then how will the rest of the underworld see the Gremory, when the full details of what transpired get out?"

Whatever reaction Riser is expecting from his minor tirade, having Venelana reach up and slip the straps of her dress off her otherwise bared shoulders one at a time is not it. As she pulls down her dress and lets her breasts fall free, the Lady Gremory stands up, looking down at him with that same smile still fixed on her face, but with the eyes of someone gazing upon an insect.

"Is this what you wish, child? Is this truly all you want? To lay with me? If that is what the Phenex Clan requires… then let it be done."

Riser slowly stands as well, forcing himself not to show his nervousness as he straightens to his full height, which thankfully, puts him a few inches over the older female devil. She's already looking down upon him metaphorically, he doesn't need it to be literal too. This is it… he has a foot in the door. But they both know what Venelana is truly saying in this moment, even as she stands there with her breasts exposed, not even remotely bothered by the fact that he can see her chest in all its gorgeous glory.

If he goes back to his father with just this, if all he has is a roll in the hay with Venelana Gremory for their troubles… then Lord Phenex will never respect his son, ever again. And yet, for a chance like this? Riser couldn't give less of a fuck.

"Then show me. Show me all of you, and we can begin. However… we don't stop until I SAY we stop, understand?"

He only catches it because he's watching her so closely, but Venelana's eyes do widen imperceptibly, as if surprised that his audacity can carry him this far. Then it's gone though, and she's inclining her head in agreement.

"Very well. If this is what the Phenex Clan requires of the Gremory Clan… let it be so."

With that slightly-changed repeat of her earlier declaration, Venelana Gremory begins to strip, right before his eyes. Her dress is already around her waist, so its not hard for her to push it the rest of the way down and step out of it. Then, all she's wearing is panties and her heeled sandals. Her thumbs hook into the waistband of said panties, and Riser watches with held breath as the beautiful brunette slides the underwear down her shapely, creamy legs, and then off of her feet.

She kicks off her sandals last, and then straightens up again, standing before him with every last inch of her perfect body on display. From her full, large breasts that aren't experiencing a single ounce of sag, to her wide, child-bearing hips that have given birth to two children over the centuries, to the trimmed bush right above her slit, tucked between her thighs as it is. She makes no attempt to be sexy or sultry in her efforts, no attempt to seduce him.

There's no need. They both know he's going to do what he's going to do regardless, and privately, Riser admires her strength, just a little. It reminds him of some of his peerage members, and how hard he had to work to make them bend to his will. Not that even his Queen, Yubelluna, can compare to the challenge before him now.

Still, Riser is confident. He would not have tried for this if he was not confident. Stepping around the table that had sat between them, Riser gestures for Venelana to join him. She does so, hands at her sides as they stop before one another. Her placid smile from before is still affixed in place, and she looks at him with eyes that are even more pitying than before.

"Is it all you thought it would be, child?"

Riser scowls at that.

"I am not a child. I am certainly not your child."

And then he reaches out to touch her before she can respond. The instinct to just grab and squeeze, to punish her for her obstinance… its strong. But Riser knows better than that. He's had quite a lot of years of practice across quite a lot of women, albeit most of them younger then this one… still, he knows the difference in benefits between negative and positive reinforcement, and knows that while one leads to short-term gains, to get long-term results, the other must be equally applied.

So, when Riser's fingers make contact with Venelana Gremory's nipple, they do not pinch or pull or twist or tug. Instead, he rolls her teat between his index finger and thumb quite expertly, pressing in on certain points in just the right way. And to his pleasure, he gets a reaction. Venelana had her mouth open to reply, probably rebuking him and reminding him that to her, he IS a child… but Riser has cut her off, and instead, her breath hitches for all of a millisecond as she feels a surprise burst of pleasure from his ministrations.

Only for a millisecond though, and then she realizes what she's doing and immediately closes her mouth, regaining her placid calm and outward façade. Even still, Riser sees the crack for what it is, and knows in that moment that he can do this… he can succeed. Reaching up with his other hand, Riser begins to caress Venelana's other breast as well. He works it over with his fingers, always gentle and tender, and altogether, explorative.

No two women are the same, Riser knows this quite well. With a peerage designed to be filled with unique female individuals to operate as his harem, Riser has plenty of experience with different types of the fairer sex, as well as all their quirks and all their desires. If the marriage had happened as planned, Riser would have been doing this with Rias on their wedding night, exploring her body, mapping out what brought her pleasure, and using it to slowly take control, to make her yearn for him and long for him.

It would have been a lot easier with the red head who had until recently been his fiancé, rather than her mother… but Riser would not be denied, and as far as revenge went, this would be fucking spectacular. To her credit though, Venelana doesn't give nearly as much of a reaction to his continued molestation of her chest as she did at the beginning. Instead, its in the smallest of movements that Riser has to take his cues. Even then, she manages to bring herself under control, that placid smile back on her face as she makes eye contact with him.

"Are you enjoying yourself?"

She doesn't call him a child outright this time, which Riser considers progress. However, her condescending tone is enough to raise his hackles. Riser grins and slides his hands from her breasts to her hips, turning her away from him.

"The real question is, are you enjoying yourself?"

She offers no resistance as he drags her back against his chest, the bulge of his painfully erect cock pressing through the crotch of his pants into her naked behind. One of Riser's hands slides past her trimmed bush, his thumb brushing over her clit expertly, and then his fingers are running over her slit. She's completely dry… or at least, seems to be. Riser knows better than to judge a book by its cover, and his fingers slowly spread open the Lady Gremory's pussy lips, pushing up into her passage.

His middle and ring fingers go up, up, and up into Venelana… and its at the tip of his middle finger that he feels it, the beginning of moisture. In that moment, with his fingers buried in her otherwise dry cunt… Riser curls them upwards, and smiles from behind Venelana's head as the barest bit of noise escapes her lips before she's able to close them up tightly. He's on the right track, and with that in mind, Riser begins to play with her all the more aggressively, fingering her and thumbing her cunt with one hand while groping and squeezing her breast with the other.

It takes time, perhaps upwards to half an hour, but in the end, Venelana reacts. Or at least, her body does. She can't stop it, not with the experience he has in feeling out a women's most pleasurable points. She might be much, much older than him, and much, much more powerful, but she's still just a woman, at the end of the day. And a beautiful one at that.

Still, even as she grows wet and her nipples harden, Venelana is as calm as ever.

"Do you believe this means anything, Riser Phenex? My body reacts to your touch. I am not so frigid as to remain unmoved by a man's gentle, coaxing fingers."

Her tone is biting, and it only makes Riser smile all the wider. He pulls his fingers free of her dripping wet quim and off of her elongated nipple and steps back from her. When she turns to face him, he's already in the process of unbuttoning his shirt and unbuckling his belt.

"I'm going to fuck you now. Assume the position."

Venelana's eyes narrow, even as she smiles with sweet poison. She doesn't react in any way as Riser reveals his sizable cock, but then, he knows he's not overly huge or anything, just above average. Really, its how the man uses it, more than anything else.

"And what position would that be, Riser Phenex?"

Chuckling, Riser shrugs his shoulders and waves a dismissive hand.

"Just bend over the back of the couch. I'm sure I'll change it up soon enough."

He thinks he detects a note of exasperation from the female devil, even as she does as she's told, moving to the back of the couch and bending over it, even as he kicks his pants off of his feet and follows her. Moving into position behind her, Riser revels in his good fortune for a moment, staring at the truly immaculate backside of one of the most beautiful devils he's ever laid his eyes on. From the back of her neck down to her ass, Venelana Gremory is just as perfect as she is from the front.

Reaching out, Riser grabs hold of the Lady Gremory's hips and drags them out a bit.

"Spread your legs."

She does so, and Riser can't help but grin at the heady feeling of having the power to command a woman like this, even if its for a short time. But then, that's the point, isn't it? The goal of all of this… is to make sure it's not just for a short time. Slowly bringing his throbbing hard-on to bear on Venelana's exposed, wet pussy lips, Riser teases her entrance for a few moments.

A moan leaves the Gremory woman's throat, but if she's ashamed or embarrassed by it, she doesn't show it. Riser isn't surprised. After all, if she's written off her body's reactions as meaningless, any involuntary noises said body makes would ultimately be meaningless as well, right? Not for long, not if Riser had anything to say about it…

Making sure he's lined up properly, Riser finally slides his cock home into Venelana's depths. She's tight, but also slick and wet from his earlier activities, causing her cunt to swallow him up nice and easy as he buries himself to the hilt inside of her. The Lady Gremory lets out a grunt at the sudden penetration, but otherwise offers no reaction as Riser begins to fuck her with slow, languid thrusts… at least, at first.

He speeds up over time and uses his hands to great effect to stimulate other parts of her aroused form. Leaning over her, he uses his superior height to easily wrap his arms around her and grope her tits, once again playing with her nipples. He treats her body like a particularly rare, exceptionally beautiful instrument, and then, once he's tuned her to his liking, he plays with her to his heart's content.

But then, that's the trick, at the end of the day. It's what Rias would have found out, if only he'd gotten a wedding night with her. The Phenex Clan were special and had been for a long time. People thought it was their tears that made them truly special, and to be fair, those same tears were his family's claim to fame and riches. Honestly, Riser wasn't even sure that his father or brothers had figured out what he had. Or maybe even, this was something unique to him, a talent that he was born with, a skill that only he was able to cultivate.

Put bluntly, regardless of how one categorized Riser's personality, there was one undeniable fact about him that Venelana Gremory was learning, slowly but surely. Riser Phenex was VERY good at sex. On top of that, however, came another undeniable fact. As a member of the Phenex Clan… he did not run out of stamina. Things start out rather average, as far as fucking goes. Riser fucks Venelana, and eventually, her already aroused body betrays her and spasms and seizes up as she rides out her first orgasm along his member while biting her lip to keep any sounds from coming out.

But then he keeps fucking her, and she keeps cumming. Perhaps this is not unusual for her, perhaps she has an active sex life and cums frequently at the end of her husband's cock. But as things go on, as Riser forces orgasm after orgasm after orgasm from the female devil, he can't help but think he's beginning to truly get her measure. And Venelana Gremory's measure is one of a lonely, dissatisfied, and altogether discarded housewife.

It seems impossible. Every male in the underworld knows of Lord Gremory's harem. In truth, the philander was one of Riser's role models in that way. But he'd always assumed Venelana was a part of that harem, and likely the most active member. This didn't feel like that though. This felt like a woman who didn't get NEARLY fucked enough, whether by choice or neglect, Riser could not say.

But he was more than happy to take advantage of the fact. As an hour of non-stop fucking passes, Riser knows that Venelana is nowhere close to breaking. Still, he likes to change things up a bit to avoid monotony, so reaching down, he hooks one hand beneath one of the Lady Gremory's shapely, pale legs and lifts it up, bringing her knee up onto the couch edge and fucking her from this new angle as she's half-turned on her side.

A surprised moan exits her throat as his cock hits an entirely new set of nerves within her cunt, and in moments, she's climaxing again, letting out shuddering mewls and breathing heavily. Her breasts jiggle and heave in his other hand, and Riser squeezes down on them, grinning viciously. He's half-tempted to speak then, to say something like 'we're just getting started', but he knows better. His victory might seem assured, the path to conquering this much more powerful devil open to him… but there's still a million ways this could go wrong and gloating too early might harden the Lady Gremory's resolve and turn her into a rock that even he could not crack.

Best to just focus on the task at hand, and that's exactly what Riser does. He fucks Venelana Gremory from behind with one leg lifted up onto the back of the sofa for another hour, counting her orgasms in his head. When she hits her twentieth climax, he pulls out of her and spins them both about, lifting her by her hips and setting her down on the edge of the dining table right behind them.

This brings them face to face, and Riser gets a nice, full view of Venelana's orgasmic face before she realizes she's no longer staring off into the distance, but now looking right into his eyes. As he slides back home into the MILF's cunt however, she can't quite control her features, and her face contorts in fresh pleasure while Riser laces his fingers in her brunette locks and pulls her head in close.

With their foreheads pressed together, Riser fucks the Lady Gremory with renewed ferocity. He's not even sweating right now, while Venelana is certainly starting to get sticky from the repeated orgasms if nothing else. To be fair, she has much more stamina than any of his peerage members, but Riser was prepared for that. He's never had to use a fraction of his true sexual strength against the women in his harem, though there have been times where, fucking all of them at once in a weekend sex marathon gangbang, he's definitely stretched his muscles and sought the limits of his endurance… but he's never found them.

If he has limits, Riser doesn't know what they are. Still, as Venelana Gremory slowly, ever so slowly bends under his will, he thinks he might find them with her. Eventually, he lets his grip on her hair go and allows the Lady Gremory to fall back onto the table, her legs spread wide open and her butt half off the edge so he can continue to fuck her without stopping. Her breasts jiggle and bounce, and eventually Riser will lean down and suckle at them like they're his mother's teats, but for now, he just watches the Gremory woman's titties bouncing back and forth with his every thrust, knowing that he's the one who's the cause of that movement, he's the one in control.

Things continue at a similar pace as the hours go by and slowly turn into one day, and then two. The position they're doing it in might change, but Riser's pace never falters, not at the twenty fourth hour and not at the forty eighth. However, there does come a point where Venelana seems like she might be close to throwing in the towel, somewhere between the first and second day. He can't have her doing that, because if she decides to stop, if she decides that she doesn't want to 'repay him in full', then he can't stop her from pushing him off of her. He knows the difference in their power is immense.

So, Riser does the next best thing. He asks her, kindly and sweetly, if she needs a break after her latest orgasm. As expected, the woman who looked down upon him for his age and spoke in such a pitying, condescending tone to him is not about to give up that easily, especially not when the question comes from Riser's lips. So long as its him suggesting they stop, the Lady Gremory insists that she can keep going.

She insists on this, right up until she finally finds the peak of her self-control, only to go tumbling down the other side in free fall. Riser notes the moment that it happens and stops asking the Gremory woman if she wants to stop or rest. He just keeps fucking her, enjoying the way she starts pushing back against him, moaning his name… and even begging for more.

He's fucking her doggystyle when that time finally comes, and as Venelana moans and mewls, as her pussy walls squeeze down hard around his cock, trying to make him cum despite the fact that he has not ejaculated a single time throughout these last couple of days. This is the true power of the Phenex Clan, not that Riser thinks his father would agree. But that's fine… that's perfectly fine.

With a vicious grin on his face, Riser reaches out and grabs a fistful of Venelana's brunette locks, pulling back viciously and forcing her glazed-over violet eyes to look up into his face.

"You're nothing but a filthy little devil slut at the end of the day, are you?"

She moans at first and doesn't respond, so Riser gives her a vicious stab with his cock, causing her to squeal from the depth his length reaches.

"Y-Yes! I'm a filthy little devil slut! Please, j-just please won't you c-cum? Please, please, please…"

Hearing those words from the powerful Lady Gremory fill Riser with satisfaction that he honestly can't quite comprehend. She's been begging him to cum for an hour now in fact, begging him to end it, to finish it. Still, he grins ferally as he continues on.

"You're MY filthy little devil slut, you whore. All mine, from now on. That seems fair, doesn't it? I'll let Rias go… but I get to keep you. You're going to be my slave, at my beck and call whenever I snap my fingers. Are we agreed?"

He doesn't need to do anything this time. Venelana immediately responds, eyes flickering like they want to roll back in her head again, tongue slipping in and out of her mouth constantly as if she's not sure what to do with it.

"Yesss… e-eye for an eye… I'm… I'm yours. I'm your filthy little devil slut. A-All yours… my husband won't care. Doesn't… doesn't even touch m-me anymore!"

Hm, it was interesting to hear that, interesting to now have confirmation of his earlier beliefs. Part of Riser feels like this triumph is slightly poisoned by the fact that Lady Gremory isn't good enough for Lord Gremory anymore… but at the same time, this is still a massive accomplishment, all the same. And if nothing else, turning this condescending bitch into his plaything makes him very, VERY happy indeed.

"I am your Master."

He punctuates that statement with a thrust, and Venelana moans throatily as she responds.

"You… are my M-Master!"

"You are my slave."

"I-I am your slave!"

Grinning, Riser reaches out and grabs one of her bouncing, jiggling titties and gives it a vicious squeeze. Venelana responds by crying out wantonly and orgasming on the spot, her inner walls clenching and squeezing down hard around his conquering cock.

"That's a good girl. Good girls get rewards… what does my slave ask of me?"

Venelana doesn't even hesitate, doesn't even think about it.

"Please! Please Master, cum inside of me! Please, fill my womb with your seed!"

And so, finally letting up on his ironclad control, Riser proceeds to do just that. Days after their sex marathon began, he finally cums inside of Venelana Gremory, filling her with one of the most satisfying ejaculations of his entire life. The broken Lady Gremory's eyes do roll back in her head at that point, and her tongue sticks straight out of her mouth as her back arches and she orgasms EXPLOSIVELY from the sensation. She'd been waiting for it so long that it became her entire world, that it became her focus… and now? Now that she has it, she's his forever.

Pulling out of the mind-broken devil, Riser smirks down at her, well-pleased with himself. Rias could have her freedom, she could have that idiot mongrel as her lover. He'd taken his revenge on the bitch for spurning him. He'd taken her mother.

-x-X-x-

The next day, Riser walks into the parlor of his mansion and has to stop for a moment at the sight before him. It's a gorgeous thing indeed, to see the vaunted Lady Venelana Gremory… in a sexy maid outfit, cleaning. With a skirt shorter than her fat ass and a neckline that shows off pretty much everything of her chest that lies above the nipple, Venelana looks one hundred percent like the slutty maid she now is, rather than the Lady she once was.

There was of course still the matter of making things official and seeing her divorce to Lord Gremory finalized so that she could begin her service to Riser in full… but they'd both been given an entire week for these 'negotiations', so that was still in the future. Riser had no doubt that shit would hit the fan… but he had the original Ruin Princess on his side now. He wasn't all that worried.

Moving somewhat silently through the parlor, Riser sneaks up on his new maid from behind as she's humming to herself and dusting a piece of furniture. Then, he reaches out and grabs her, wrapping his arms around her body and groping her chest, just like that. He can tell immediately that despite his quiet approach, she definitely knew he was there.

That doesn't stop the big-chested beauty from playing along though, letting out a slightly fake yelp, followed by a very real moan as he pulls her maid outfit down and lets her titties pop free, groping them directly.

"Ooh, Master~ d-did I do something wrong? Are you not happy with my work?"

Riser considers the question for the moment. There's always the dungeon and flogging his new maid does have its appeal… but no, that can come later. Right now, he's looking for some instant gratification.

"You're fine, I just have something else for you to clean. Get on your knees."

As the once-proud former Lady Gremory turns and kneels before him, her tits still hanging out of her skimpy maid outfit quite obscenely, Riser's grin has become positively vicious. He gestures at his crotch, and Venelana hurries to unbuckle his belt and unbutton his pants, tugging them down and then his boxers as well. As his cock swings up from its confines, she makes no effort to avoid it slapping her in the face, and she even gasps with delight as it does so, nuzzling it with all her heart.

The brunette then takes his length in one hand while the other moves beneath it to expertly massage his balls. Riser marvels at the fact that her husband neglected her enough to make breaking this bitch to his will so easy, even as Venelana, her violet eyes never leaving his face, descends upon his cockhead with her mouth, opening wide and slipping him between her lips.

Briefly, she sucks on just the tip of Riser's member, swirling her tongue around the bulbous head of his length as she strokes the rest of his shaft with her smooth, creamy palm. Then, she shifts her hand to the base of Riser's dick and begins to slide her mouth further and further down his member. Riser brings a hand up as well, and places it atop Venelana's head.

"That's it, slut. Just like that."

He grins down at her as she looks up at him, eyes focused on his face, on making sure she's making him happy. She swallows down his member, repressing her gag reflex with the ease of a woman who has quite a lot of time on him, and Riser groans as the MILF takes him down her esophagus and gullet, until eventually, her lips suction around the base of his cock, her hand falling away entirely.

That's the moment when Riser tightens his grip on her brunette locks and holds her there, forcing her to stay. Venelana's violet eyes begin to water, and after a few moments she starts to choke, but she doesn't fight back, doesn't try to resist. Luxuriating in that power for just a brief moment more, Riser lets her up after, allowing her to get some air into herself again, before forcing her back down once more. Then, he grabs hold of her head with both hands and begins to face fuck her, right then and there.

"Gagkh! Gagkh! Gagkh!"

As Riser luxuriates in the tight, spasming feel of Venelana Gremory's throat flexing around his member, her drool collects on her chin and then falls down onto her massive, jiggling mammaries. Grinning at the sight, Riser Phenex doesn't let up in giving the Gremory woman everything he has, not even for a moment.

Now that she's broken, now that she's his, Riser doesn't hold himself back verbally either. Eyes twinkling, the devil looks down at his new maid and chuckles darkly as he lets her in on a little secret.

"We're just getting started."

-x-X-x-

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