A Matured Degenerate (High School DxD)

Poll Winner

Themes: Fucked Silly, Mind Break, Master/Slave

Summary: Increasingly frustrated with their unfulfilling sex lives, Venelana Gremory and Lady Phenex both decide to meet with Issei Hyoudou under the pretense of “educating” him on how to be a good future husband to their respective offspring. What follows instead changes their lives forever as they both get what they always wanted.

-x-X-x-

“Um… I’m not too sure about this.”

“What’s there to be sure about, Issei? You’re a grown man now, aren’t you?”

“Mm, that’s right. You’re an adult now. It’s ridiculous that you still have that pesky virginity of yours.”

“Obviously, you should have lost it under different circumstances…”

“… But we must work with what we have. Not to worry… we’ll teach you everything we know~”

Issei’s eyes bounce between the two gorgeous mature, older women in front of him. It was true that he was an adult now, with all the responsibilities that entailed. Of course, given everything he’d been through to reach this point, one might say he already had a lot of responsibility heaped on his shoulders anyways.

This though… this was different. Especially given what Lady Gremory and Lady Phenex were… offering.

When he’d received an invitation to receive etiquette lessons, Issei hadn’t been sure what to expect… but he’d gone along with it anyways. Instead of being taught what fork to use at dinner however, he’d walked into this extremely expensive, incredibly extravagant hotel suite and found himself face to face with these two devilish ladies… clad in nothing but lingerie.

Lady Gremory was wearing black lacy lingerie that pushed up her chest and accentuated her gorgeous thighs, thicc hips, and narrow waist. Lady Phenex wasn’t much better, clad in all red lingerie that made her chest look like a heart and clad her peach-like ass perfectly.

Honestly, if Issei didn’t know any better, he would say he was dreaming. But… no. This was all very real, wasn’t it?

“Lady Gremory and Lady Phen-!”

“Please, don’t be so formal Issei. Call me Venelana.”

“And call me Isabella.”

Issei gulps as they both lean forward at that, giving him matching hungry grins. You know what, he was going to say it… in the privacy of his own mind, anyways. These two MILFs were fucking thirsty as fuck! He didn’t pretend to know what their home lives were like, but Issei figured he knew enough to be able to say that neither of their husbands were giving them the attention they obviously needed!

Of course, anyone who knew Issei would probably be questioning his reaction to all of this. He wasn’t going to take advantage? He wasn’t already leaping at this opportunity? Wasn’t he the legendary pervert?! Shouldn’t he already be fondling and playing with their offered-up bodies?!

Well, to be fair, he actually had a lot of trauma that had held him back from forming meaningful physical relationships for the longest time. Only recently had he been able to get over the fact that his very first girlfriend had taken him on the best date of his life only to end it by quite literally killing him.

That had made intimacy, even kissing, all but impossible for Issei for the longest time. He was better now though. But part of being better also meant being more mature. He was a grown man now, so…

“Just so we’re all on the same page… you both understand what you’re asking me to do here, r-right? Because if I go all out… I don’t think I can stop myself.”

The two gorgeous MILFs share a look of amusement at that before glancing back at him and tittering.

“Do your worst, Issei. They call me the Flaxen-haired Madame of Extinction for a reason, you know~”

Isabella Phenex just rolls her eyes at that.

“Hmph, I may not have some special title or anything like that… but I’m no pushover either.”

Grinning wickedly, the Lady Phenex leans forward with her hands on her knees and her tits out, giving him a great view down her corset.

“Show us what you’re made of Issei, and from there we’ll work to build you up into something… even greater~”

Issei swallows thickly… before slowly nodding and reaching for his pants. Fuck it. They wanted him? They’d get him.

-x-X-x-

“OH GOD! YES, YES, YES! D-DON’T STOP! HOOOOOH!!!”

Grunting, Issei tightens his hold on Venelana’s ‘flaxen hair’ and pulls her head back even harder as he slams his entire length of throbbing fat cock meat into her from behind over and over again.

SMACK! SMACK! SMACK!

“Mrgrghl~”

Meanwhile, his other hand is occupied with Isabella Phenex’s golden locks as he pushes her face into his balls, all but tea-bagging her right there while he plows her friend and fellow lady silly from behind. He doesn’t hold anything back. Not his strength, not his speed, not his stamina. And he CERTAINLY doesn’t hold back his rather sizable, fat, girthy cock either.

Issei had begun to get an inkling of how this would go when he’d first exposed himself to the two older women. He’d dropped his pants and boxers, unveiled his slowly rising dick (because of course he was getting hard in the presence of a pair of lingerie-wearing MILFs) and watched as their eyes widened in unison and their jaws dropped open. Their faces quickly reddened after that, even as they tried to rein in their reactions.

He wasn’t an idiot though. Or at least, he wasn’t as much of an idiot as he maybe used to be. From just their reaction, Issei knew beyond a shadow of a doubt that he had the biggest fattest dick that either woman had ever seen. Which was crazy but at the same time… kind of explained a lot.

From that point on, Issei kind of had defacto control of the situation. The two women had dropped to their knees and then forward onto their hands almost wordlessly, staring at his dick like they were mesmerized by it. They’d crawled forward in unison and proceeded to share his massive cock between them, getting him nice and hard in no time with the use of their soft hands, warm mouths, and wet tongues.

Then their corsets had come off and their breasts had come into play and well… Issei was done playing around. He’d all but ripped Venelana up to her feet, spun her around, and begun fucking her silly from behind. All the while, Isabella had been relegated to ball sucking duty as she knelt between his spread legs and tilted her head back so he could teabag her repeatedly.

Part of Issei did wonder briefly if he was going too far… but neither MILF expresses a single ounce of protest. In fact, they’re both very much into it. REALLY into it in fact.

“Y-Your cock is amazing, Issei! Don’t stop! I’ve always wanted to be fucked by a REAL MAN!”

Venelana was a mother twice over. What that said about her husband… well, Issei would try not to think disparaging thoughts about another man while he was fucking that man’s wife he supposed. Instead, he focuses on the woman herself and giving her exactly what she asked for. Though he’s already sick and tired of her panties rubbing against the side of his dick… and frankly, her yapping could stand to be corrected a bit as well.

With a lustful growl, Issei kills two birds with one stone. He reaches down for a second to grab hold of Venelana’s lacy black panties and rip them off of her body, causing her to gasp and moan in delight. But before she can tell him more about how much of a real man he is for being rough with her… Issei proceeds to shove her torn panties in her own mouth, gagging her with them.

“Mmmmph~ Nnnngh~”

Of course, he doesn’t have any way of keeping them in there. Venelana COULD have spat them out immediately if she wanted to. She doesn’t though, she keeps them in her mouth as she lets out muffled squeals and her eyes roll up in her head, creaming herself again and again on his big fat cock.

Until finally, after he makes her cum for him who knows how many times, Issei can’t hold back anymore. With snarling roar of victory, he pulls out at the last second, whips Venelana Gremory around and forces her back to her knees again before unloading all over her face and tits. By the time Issei is done cumming, Venelana is positively drenched in his seed. One of her eyes is plastered shut by his cum, her panties poking out of her mouth are soaked with his jizz, and her spectacularly large breasts are dripping with rest of his ejaculation.

Issei admires the view for a moment, but ultimately he’s not even remotely exhausted. Hell, he’s not even panting for breath. And with a certain pair of lips wrapped around his balls and sucking away at them dutifully, Issei is ready and raring to go again before he can even fully go soft.

Pulling Isabella Phenex out from between his legs, Issei pushes her into Venelana. The lust drunk Lady Phenex doesn’t even hesitate to glomp her peer, pushing a dazed and still-recovering Venelana onto her back and going to town on her cum-covered front right then and there.

Even as she’s going hog wild in licking and lapping his seed off of Venelana’s body, along with some bites judging by the brunette MILF’s yelps and squeaks, the Lady Phenex is also lifting her ass high into the air and using a free hand to spread her pussy lips wide open for him.

Issei pauses, not from hesitation or anything like that… but just because it’s such a glorious and beautiful sight. Still, taking in the view ends a moment later and he steps forward with another lustful growl on his lips. One of his feet comes down on the back of Isabella’s head and pushes her face further into Venelana’s tits. The other plants itself between the legs of both women.

Finally, he uses his hands to grab ahold of Isabella’s hips, holding the blonde MILF steady as he crouches down and places the head of his cock against her sopping entrance. A moment later and he’s inside of her… and once he’s inside of her, he doesn’t really take his time.

PLAP! PLAP! PLAP!

Rough, hard fucking right from the start. Issei has never made a secret of what kind of man he is. Forget all that meme shit… holding hands and tender kissing and lovemaking? That’s not fucking degenerate. That’s not perverted. No, at the end of the day… a real pervert knows that it’s all about hardcore, no holds barred FUCKING.

Issei doesn’t hold back because like he told Venelana and Isabella before, he can’t hold back. Now that he’s finally having sex, he HAS to give it his all. Nothing slow. Nothing lovey-dovey. All hard, all speed ahead, all strength behind each thrust.

Luckily, Isabella seems to love being fucked silly just as much as Venelana professed to. She’s unable to actually say as much with him pushing her face into Venelana’s tits, but he can tell from the way her pussy clenches around his cock and she cums for him over and over again that she’s enjoying herself immensely.

So he continues to jackhammer in and out of her cunt, treating her like a cum rag and fucking her just as deeply and relentlessly as he fucked Venelana. Both Lady Gremory and Lady Phenex are needy fucking slut-whores when one peeled away everything else. One look at his cock and they couldn’t have been faster in submitting to him.

Issei luxuriates in that feeling, reveling in the sense of conquest that washes over him as he pounds Isabella’s pussy out into the shape of his dick for a good long while before finally reaching his peak again. Just like with Venelana, he doesn’t creampie her. Instead, he pulls out at the last second and coats her ass and back in his seed, covering her body in a humiliating manner as his balls churn and empty all over her.

When he’s finally done, Issei removes his foot from Isabella’s head and takes a step back. He moves to a chair off to the side and collapses into it, not quite tired or anything like that… but feeling pretty good about finishing what he’d started. Indeed, it takes the two MILFs time to recover from what he’s done to them. Takes them time to slowly pull themselves back together.

The first thing they do after gaining their sense back is look at one another… and immediately revert to ravenous bitches desperate for more of his cum. Issei watches on in a mixture of amusement and arousal as the two women clean one another off with their tongues while also heatedly making out with each other from time to time… along with some nipping here and there.

Finally though, they pull apart for air long enough to notice him sitting off to the side… or more specifically, notice his cock and the fact that he’s still rock hard even now and doesn’t even look tired.

No words pass between Venelana and Isabella. They crawl over to him of their own volition, nestling themselves between his knees and stroking his cock with their hands as they stare up into his eyes wordlessly… but also needly.

Issei raises an eyebrow at them both in response, before grinning somewhat cheekily.

“So ladies… what would you say the first step to ‘building me up into something greater’ would be?”

They’re both confused for a moment before their eyes widen in recognition and they realize Issei is throwing Isabella’s words back in their faces. They both blush at that, but then Venelana gets a wicked glint in her eyes.

“Well… seems to me that the first step would be securing your hold over the two gorgeous MILFs you’ve just broken with your magnificent, massive cock.”

Catching on quick, Isabella eagerly nods as she hungrily licks her full red lips.

“Make them submit to you, Issei. Reforge them to your will. Don’t let up for even a second… fuck them both silly until they call you Master and no other~”

Issei’s cock jumps in their shared grasp at that, causing them both to tremble in anticipation. But he just stays where he is and looks down at them, feigning boredom.

“Hm… I don’t know if I care enough to do all of that. I feel like if they really wanted more of my big, fat cock… they would submit of their own volition.”

The funniest part is, they don’t even hesitate or resist for a second.

“Please fuck me more, Master!”

“No! Master Issei, please use this cum rag first! I need your cock! I need it so bad!”

As the Lady Gremory and Lady Phenex argue about who deserves to be fucked by their new ‘Master’ first in the next round, Issei just grins wickedly. Part of him does wonder if he might be going too far… but that’s a small, easily silenced voice in the back of his head. Ultimately… this was precisely where he was meant to be.