A Matured Degenerate Ch. 2 (High School DxD)

Poll Winner

Themes: Fucked Silly, Mind Break, Master/Slave

Summary: Part 2 of A Matured Degenerate. Eager to continue Issei’s “education”, Venelana decides to bring along Grayfia, who she knows is equally frustrated with her own sex life. Needless to say, Grayfia will finally get what she always wanted and in no time at all, be nice and pliant as she gets fucked silly on Issei's cock.

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“… I want to hear it from her.”

Issei watches as Grayfia Lucifuge freezes up at his cold tone. The silver-haired maid stares at the floor, her hands clasped in front of her in silence. Meanwhile, Venelana stands next to her, the Lady Gremory having just gotten done explaining to Issei that Grayfia was going to ‘help’ this time… namely because she was just as frustrated with her sex life as Lady Gremory and Lady Phenex had been.

It was a little hard for Issei to believe though. He didn’t want to think Venelana would resort to coercion just to get her way, but he needed to know for sure. More than that, it had always felt like Grayfia was looking down on him. But then again, he was an adult man now, and it had been years since they’d first met, so maybe… well, maybe things had changed.

Still, just because Venelana said something didn’t mean he would accept it as gospel. That’s why he’d demanded that Grayfia speak up and reiterate the things the Lady Gremory had just claimed.

Far from being disturbed by this, Venelana just grins and steps away from Grayfia’s side.

“Of course. Go ahead, Grayfia. Be honest now. Consider that a direct order from your Mistress.”

Grayfia hesitates briefly, more uncertain of herself than Issei has ever seen her before. She’s always seemed like a consummate professional to him. Even when interacting with her husband, Grayfia has always acted more like Sirzechs’ Queen and Maid than his wife. And yet… maybe that was a sign of just how frigid their love life truly was?

“U-Understood, Lady Gremory. Mister Hyoudou, I… I am here to offer my body up for your ‘training’. Use this worthless maid however you see fit. It is my pleasure to submit to you.”

Issei narrows his eyes and decides to take a leap, right then and there.

“When was the last time you had an orgasm, maid? And remember, you’re under orders to be honest.”

Venelana grins wickedly at that, while Grayfia freezes in panic for a moment before ducking her head and murmuring something under her breath. Issei has really grown into his devil powers at this point, to say nothing of the strength that Boosted Gear provides him. Meaning, his hearing is way better than a normal human by now. And yet…

“Sorry, what was that? I think I heard you wrong.”

Taking a deep breath, Grayfia repeats herself with a stronger voice.

“Over one hundred years… sir.”

That’s what he’d thought he’d heard originally. Still, that was… insane. Issei can’t help but cringe a little bit. After all, Grayfia was a mother… and her son was NOT over a hundred years old. That meant… well, it didn’t mean anything good, did it?

From the side, Venelana chuckles throatily.

“What do you say, Issei? Will you help her out? Or maybe you need some extra incentive. Grayfia… that thing we discussed. Do it now.”

Grayfia’s face grows even redder, but in the end she nods with a bowed head.

“Y-Yes, Lady Gremory.”

A whirlwind of movement follows, almost too fast for the naked eye to see. Issei is able to mostly follow all of it though, but even he has to admit Grayfia is moving at blinding fast speeds. In this instance, it’s not about the journey anyways. It’s about the destination. Mere seconds later, and it’s finished, causing Issei’s breath to hitch at what he’s witnessing.

There, before his eyes, Grayfia Lucifuge has stripped out of her entire maid uniform as well as the silver lingerie she was wearing underneath. But she hasn’t just exposed her entire body to him. She’s also prostrated herself before him, forehead pressed into her knuckles as her hands are flush with the ground in front of her, ass raised up into the air as her back is ever so slightly arched.

Even that alone is certainly gorgeous. Grayfia with her heart-shaped derriere raised into the air for him, her silver locks draped over her downturned face in a position of complete and utter submission.

… But she’s also a maid, so of course, she didn’t just leave her uniform and silver lingerie strewn across the floor like some trashy harlot. No, in those scant few seconds where she’d stripped naked with lightning speed, she had also folded up every piece of her uniform and then arranged them on the floor on either side of her. To her right is her maid uniform in its entirety, laid out for his viewing pleasure. To her left is the silver lingerie that he’d only gotten a glimpse of covering her gorgeous, bodacious body before it was removed.

Issei swallows, his cock already straining in the confines of his pants. Of course, not to be entirely outdone, Venelana saunters over while he’s staring down at Grayfia and drapes herself over him. Wrapping her massive tits around his head, she reaches down and around his body and frees Issei’s cock from its confines, stroking it in and giving him a handjob from behind as she giggles into his ear.

“What do you think, Issei? Do you like what you see? Do you believe Grayfia is being honest now?”

… Yes. On both counts. But Issei remains silent for a moment, not intending to let them see just how shaky he currently is. And it works too, because Venelana seems to take his silence as being unconvinced, causing her to wind her way around his body and pout at him as she slowly descends to her knees.

“Let us show you our sincerity, Issei. Grayfia, come here.”

But the naked maid doesn’t move from her spot.

“Lady Gremory instructed me to only listen to Master Hyoudou’s instructions if things went this far. From this point on, I am to attend to only Master Hyoudou and obey only his orders.”

Judging by Venelana’s flash of irritation, the exchange wasn’t planned. Though she tries to pretend it was, smiling sweetly up at him a moment later.

“See?”

Issei huffs and rolls his eyes, slowly starting to relax. This was just like Venelana and Isabella, in the end. Two whorish MILFs who couldn’t get enough of his massive fat cock. Grayfia was the same way… but he had to admit, he liked the thought of having the gorgeous no-nonsense maid submitting to him. No, more than that… he REALLY liked the idea of making Grayfia cum for the first time in a hundred years. Before that though…

“Grayfia, come here.”

Without missing a beat, the maid lifts herself up out of her prostration and crawls over to him, looking at his cock with a hunger that couldn’t possibly be faked. She wants this. She wants him. His big fat juicy cock is staring her right in the eye and she’ll do anything to get it.

Venelana sidles to the side slightly to make room for Grayfia to kneel next to her and then presents the silver-haired woman with his dick while at the same time leaning in and begins to lap up and down one half of his shaft. Grayfia looks up at him for a moment seeking approval, so Issei gives her a nod… and is in turn treated to the beautiful naked maid leaning forward and taking up the other half of his shaft.

Issei tilts his head back and lets his eyes drift shut for a moment, shuddering in pleasure as his hands come down atop the heads of both women. His fingers card through their silken locks, even as they bob up and down on his cock, sharing his throbbing man meat together. He’s more than big enough for the two of them to have room to be fair. There’s no competition here… just a noblewoman and her maid, both horny and slutty and cock hungry to an extreme degree.

Eventually, Venelana grabs Grayfia by the back of her head and pushes her firmly down his cock, pulling back and cooing at her as she does so.

“That’s it… take your Master’s cock, maid. Suck it all the way down. Down the back of your throat. Use that tongue of yours. Don’t stop even when your nose tickles the base of his massive fucking member.”

Grayfia gurgles, her eyes fixed on his face. Venelana probably thinks that the maid is already too horny to care about who’s orders she’s following by this point. Issei knows better though. He sees it in Grayfia’s eyes… if he’d countermanded Venelana for even a second, Grayfia would have refused to follow the Lady Gremory’s commands.

He doesn’t though. He stares back at Grayfia, allowing Venelana to speak for him momentarily. When she sees that in his eyes, the naked silver-haired maid willingly submits and chokes down his entire cock, taking him down the back of her throat like she’s been told and swirling her tongue this way and that.

“Gagkh… Gagkh… Gagkh…”

Her throat feels amazingly tight around his dick, even as Issei shudders some more in abject bliss. Seeing this, Venelana chuckles again.

“Enjoying yourself, Issei? I knew you would like this needy maid’s throat. She likes to put on a good show of being frigid, cold, and unfeeling… but the truth is, she just needed a real man all this time.”

Well now, that was a bit cruel considering who Sirzechs was to the Lady Gremory. Still, Issei supposed all was fair when it came to private dirty talk. Besides, what they were doing here today was far more of a betrayal than anything they could possibly say… and he hadn’t exactly balked at it, had he?

Suddenly, Issei decides he wants to be buried ball’s deep inside of Grayfia Lucifuge’s cunt. If he’s going to be this sort of bastard, straight out of a hentai doujin, then fuck it… he’ll go full tilt. With a grunt, he pulls his cock out of Grayfia’s throat, causing her and Venelana to both pause.

“Get dressed.”

For a moment, Issei garners some amusement from their shocked dismay and disappointment. Then, he continues on, making it clear what he wants.

“Just the uniform. No undergarments.”

Understanding dawns in their eyes and Grayfia quickly rises to her feet.

“… Yes Master Hyoudou.”

In another whirlwind of motion that takes place over a scant few seconds, Grayfia is fully uniformed as a maid once more. The silver lingerie, however, remains off… and as she stands there before him, Issei doesn’t bother hesitating. He steps forward, grabs the silver-haired maid by her hips, and spins her around before proceeding with bending her over one of the very tables she might have been tasked with cleaning under different circumstances.

Grayfia gasps, her ass lifting subconsciously into the air and causing her skirts to hike up a couple of inches. Issei flips them up the rest of the way though, not having the patience for teasing or toying with her. His throbbing cock is still waiting for action after all, glistening with hers and Venelana’s spit.

That said, he DOES bring his palm down on Grayfia’s pale ass the moment her skirts are flipped up, provoking a cry from the silver-haired maid as he spanks her buttocks one cheek after the other. Just from the way she jolts and moans and gasps, Issei can tell that she’s enjoying this… which only makes him wonder why it’s been so long since she came.

But he’s not about to bring up Sirzechs or anything like that. Right now… this is between Grayfia and Issei. Well, and Venelana, but the Lady Gremory is smart enough to realize she should take a step back and just enjoy the show. Touching herself off to the side, the brunette MILF bites her lower lip as she watches Issei bring his cock up to Grayfia’s drooling slit and begin teasing it for a moment.

He especially makes sure to push the bulbous head of his shaft against Grayfia’s clit, watching her gasp and moan and squirm before him in her bent over position.

“… You really are a slutty maid.”

Before she can reply, if she was even going to try, Issei thrusts forward. His massive cock slams home into her gushing yet tight cunt, which tries and fails to clamp down on his dick like a vice. Despite her pussy walls’ best efforts to hold him in place or push him out, Issei barrels forward with ease… and quickly sets a punishing pace that has Grayfia moaning up a storm and squealing in pleasure and bliss.

PLAP! PLAP! PLAP!

As his hips impact her ass with every thrust into her sopping cunt, Issei even goes a step further and reaches forward, grabbing hold of Grayfia’s silver braids to pull back and use as reins. Her back arches further and her head comes up, her melodic voice filling the room all the more loudly.

This… this felt right, Issei had to admit. He wasn’t sure if it was the dragon, the devil, or the man speaking, but he felt like this was right where he belonged. Hell, maybe it was all three. Dominating beautiful women like this, using his big fat cock to put them in their place… it just felt like he was always meant to do this. Venelana and Isabella and now Grayfia… Issei had never been happier, really.

“Yes! YES! SHO GOOD! OH, OH, OH… I-I’M CUMMIIIIING!!!”

And neither has Grayfia, it would seem. Despite a dry spell she claimed lasted more than a century… or perhaps because of it, Grayfia barely lasts five minutes on Issei’s cock before she cums for him. And once she reaches that first orgasm, it only seemed to build from there. The time between her first orgasm in a hundred years and her second is no time at all, and then she’s cumming again and again all over his cock.

Issei never lets up, never slows down, and never shows her a single ounce of mercy or hesitation. You had to take a firm hand with deprived, desperate MILFs like these, he was beginning to learn. Just like with Venelana and Isabella, Grayfia wanted to be put in her place but it was still his job to make sure that happened.

That’s why, in the end, he pulls out at the last second in the midst of her fifteenth orgasm and yanks Grayfia around by her hair, forcing her to her knees just in time to cum all over her face and the front of her maid uniform. His seed truly gets everywhere, coating not just Grayfia’s face but also her hair, her bonnet, and the front of her dress.

Issei doesn’t show any regret though, even as he finishes cumming and stares down at Grayfia’s messy exterior for a moment before finally speaking.

“I accept you as my maid, Lucifuge. Now clean yourself up.”

Looking like she’s just found her new god, Grayfia shudders, her cum-coated lashes fluttering for a moment before she finally nods.

“Y-Yes Master Hyoudou… as you command.”