The Sleeping Dragon (High School DxD)

A/N: Here's the new Chapter! Which also means the next four chapters are up on my Patreon for early access as well as the chance to vote on the direction of the story!

The Sitri Sisters, one last time~

-x-X-x-

Issei’s harem was large and varied, but if one was a bit ham-fisted with it, one could still categorize his girls into neat little boxes. Like for instance, he had three types of women in his hoard. The first type of women were the type who liked to drop in unannounced and make him accommodate them. They would show up at random and expect him to drop everything in order to make them happy.

This type of woman had a lot of overlap with the type of woman who also liked to be punished, because most of the time Issei could NOT afford to drop everything as the Ruler of Heaven just to accommodate his girls. So they tended to wind up bound and gagged and dangling from the ceiling someplace until he found himself with enough free time in order to indulge both them and his own raging libido.

The second type of women found in Issei’s hoard were the more disciplined type. They were the ones who set up appointments with him ahead of time, fitting themselves into his busy schedule so that when they arrived, it was always when they were supposed to arrive and he could always give them his full and undivided attention.

These were also the type who preferred to be pampered and preferred to be focused on completely and totally. They also had some overlap with the sort of woman who liked to be punished, but not the type who liked to be ignored. They might wind up dangling from the ceiling, but Issei would always be there for every last second of it.

And then there was the third type of woman… the type that Issei had to make time for himself. Not because they didn’t want to be with him or were reluctant to ask for a moment of his time… none of the women in his harem didn’t want to be there, or he would have already cut them loose. No, this third type of woman existed solely because they were workaholics… and Sona Sitri was the biggest workaholic of them all.

Finding her in her office on her estate, Issei can’t help but smile at seeing her hard at work at her desk, pouring over documents and looking focused and determined… but also more than a little tired. Even after all these years, Sona is a workhorse. Always has been, always will be. Hasn’t gotten better with time either, because why would she? After graduating from Kuoh Academy, she’d taken over running the place… and also started up half a dozen side ventures as well, including an Academy in the Underworld purely based on Rating Game Prep.

Sona Sitri didn’t know the meaning of the word chill, truth be told. Which was why every once in a while, Issei took the time out of HIS busy schedule to try and teach it to her. Sure, maybe it was never going to actually work, but they’d have fun trying at the very least.

Of course, Sona notices him the moment he arrives. Her eyes flick up to him and she blushes for a second, already knowing where this is going. Still, just because she knows where it’s going doesn’t mean she’s just going to give in. She’s grown a lot from the Student Council President that he fucked silly all those years ago.

“Issei. I’m sorry but I’m too busy to talk.”

Issei chuckles at that even as he makes his way across the room and around the desk. Sona stiffens up just a tad as he moves, her eyes not quite tracking him… but she’s definitely watching him out of the corner of her eye.

“No need to talk, Sona. I can be quiet.”

“Issei…”

Even with the warning in her tone, Issei doesn’t bother heeding it. He just reaches out and places his hands on her shoulders. Then, he begins to knead. Sona tenses up at first… before involuntarily relaxing at his touch, letting out a soft but heartfelt moan a moment later.

“See? Keep working, Sona. I’m not going to disturb you. I’m just here to help.”

She tries to follow his instruction. She really does. A testament to her work ethic, to the bitter end. But Issei’s massages are to die for. One might even call them, heh, divine. As he works his fingers into her shoulders and back, Sona melts more and more into his grasp, relaxing further as she gasps and moans while trying to focus on the papers in front of her. But it’s a losing battle and they both know it.

The more he massages, the more relaxed Sona gets. And the more relaxed Sona gets, the harder it is for her to focus. They’ve done this song and dance more times than either of them can count over the years. Sona never fails to break. Any minute now, she’ll stop what she’s doing and demand that he ‘get it over with’ so she can get back to work. Needless to say, they both enjoy what follows each and every time despite her spicy attitude.

Only… this time, before Sona can break, an interloper interrupts them. Appearing in a flash of devil magic, covering her mouth mid-yawn, Serafall Leviathan stretches her arms over her head.

“Soooo-tan! I’m boooored! It’s my-!”

The ‘day off’ part remains unsaid when Serafall belatedly realizes Sona isn’t alone. Her eyes light up when she sees Issei standing behind her sister, massaging her shoulders.

“Ooooh! Are we doing massages?! Me next, Issei! Me next! I’m soooo overworked, you have no idea! I definitely need a big fat massage from those heavenly hands of yours! God as my witness~”

Both Sona and Issei roll their eyes at that as Serafall is not harmed in any way by using the Lord’s Name. Most Devils still didn’t know that Issei had relaxed that part of his predecessor’s system. It only hurt if you were a Devil who used God’s name in vain now. A compromise between him and Gabriel. Heh, even after all this time his beloved was a bit of a Daddy’s Girl.

Still… it was incredibly obvious that Serafall was not nearly as overworked as Sona. Not just because she had been about to say she was on a day off, but also because of how she’s dressed. No Magical Girl Uniform insight. Instead, Serafall is dressed in a simple tank top and pair of sweats. She still looks amazing of course… but there’s no way in hell he’s going to believe she NEEDS a massage in the same way Sona does. And yet…

Issei removes his hands from Sona’s shoulders, making the younger Sitri Sister let out a grunt of surprise.

“Ah, well Sona was just telling me she didn’t want to be disturbed anyways… so I’ll leave her alone and help you out instead, alright? You can be quiet, can’t you?”

Serafall glances to Sona and then back to Issei before grinning wickedly.

“Of course!”

“You two…”

Sona’s exasperated tone makes it abundantly clear she knows what’s going to happen next. But she also doesn’t try to fight it, even as Issei circles around Sona’s desk once more, moving behind Serafall. The Great Satan gasps and then coos when, instead of massaging her shoulders, he bends her over the front of Sona’s desk. Her hands grab onto the very edge of the furniture, so she’s not actually getting in Sona’s way, even as her ass immediately and instinctively thrusts out in his direction.

Issei, meanwhile, wastes no time in dragging down Serafall’s sweats to reveal a distinct lack of panties. His cock is also freed from its confines in under a second, and he sheathes himself inside of her clenching, moistening twat a moment later. Serafall lets out a cry that is very much NOT quiet, even as Issei digs his fingers into her hips and ass and begins to plow her from behind right in front of her sister.

“A-Ah… oooh… nnngh~ T-This is… mm, a s-strange sort of m-massage, I-Issei…”

Smirking over Serafall’s shoulder at an exasperated and clearly distracted Sona, Issei winks.

“I’m the expert on massages here, Serafall. I can look at a woman and know exactly what sort of massage she needs. Sona needed an external massage… but you needed an internal one.”

WHAP! WHAP! WHAP!

As his ball sack slaps up against her clit and mound again and again, Serafall moans loudly and wantonly, not even TRYING to be quiet.

“Nnngh! G-Guess… you ARE the e-expert! Guh!”

Issei does nothing to silence her though, simply giving Sona a wicked grin over the top of her big sister’s head until finally, the younger devil rolls her eyes and metaphorically throws her hands up in the air.

“You two are the worst!”

With a growl, Sona proceeds to gather up her papers into neat, orderly piles, slide them into manilla filing folders, and then tuck them into the drawers of her desk in what is no doubt a supremely efficient and incredibly organized system. In mere moments, the surface of the desk is completely cleared, practically just as fast as if one had swept all of that paperwork onto the floor instead.

Once done, Sona hops up from her seat, shucks off her pants and panties, and hops up onto the desk with another lust-filled growl. Her hands grab a startled Serafall by her pigtails and drag her big sister downwards.

“Issei told you to be quiet, Sera. But I guess even after all this time, I’m the one who has to properly discipline you when you act up.”

With that, Sona forces Serafall’s mouth onto her muff, muffling the Great Satan’s moaning and forcing her to eat her out at the same time. Something that Serafall of course takes to with great gusto. Soon enough, Sona is the one moaning up a storm as she humps Serafall’s face while he drives into the Great Satan from behind, forcing her deeper into her sister’s pussy mound.

The office fills with the lewd and lurid sounds of feminine moaning and flesh slapping against flesh as they spit roast Serafall between them. Not that she minds one bit from the way she’s clearly voraciously eating Sona out while also thrusting her hips back into Issei’s pistoning prick again and again without fail.

Issei, for his part, IS massaging Serafall. Sort of. His fingers knead and grind against her beautiful, bountiful bubble butt. For all her power, she’s got curves for days and a softness to her feminine parts that can’t be beat. If she were a human, her physical strength would probably translate into a somewhat grotesque body builder of a person. But because she’s a devil, she can be super strong AND have an hourglass figure with curves for days.

In the end, Serafall cums first and most often. Climaxing all over his cock as she moans into her sister’s cunt, the Great Satan orgasms over and over again. Sona cums too before he does, squirting all over Serafall’s face at least once before finally, Issei tips over the edge and lets Serafall’s insides milk him of his release.

As soon as he’s finished, he pulls out of her. By unspoken accord, Sona and he all but toss her sister to the side, leaving her to drop to the floor still moaning. Not that Serafall is injured by this or anything. In fact, she immediately flops over onto her back and begins fingering her creampied cunt and playing with one of her breasts while watching the two of them with anticipation in her heavily lidded eyes.

She’s right to do so, of course. As soon as Serafall is out of the way, Issei is stepping through the space she’s left behind. Sona welcomes him with open arms and open legs as he slides right into the place between her thighs… and then slides right into her cunt as well for good measure. As his cock fills her up, her ass now on the edge of the desk and her legs wrapping around his waist, Sona drapes her arms over his shoulders and gives him a glare with no heat in it.

“… Hate you… hate you both.”

Issei just grins as he runs a hand through Sona’s perpetually short hair and slides his fingers along the back of her skull.

“No. You don’t.”

Before she can respond, he pulls her into a tongue-filled kiss right then and there on the spot, making her moan into his mouth as he also begins jackhammering in and out of her down below. His cock pistons into her sopping wet cunt with intense speed, making her gasp and shudder and cry out into his lips.

In the end, for all their differences, the Sitri Sisters are a lot alike. Both of them gets off on being dominated. Both of them gets off on being overwhelmed by both pleasure and the power of their partner. Sona’s legs start out wrapped around his waist, but the harder Issei fucks her, the further she winds up leaning backwards on the desk. Eventually, she’s laid back on the desk and her legs are up in the air, her shoes knocking against nothing as he fucks her in a mating press.

Her arms wrap around her neck properly, her hands carding through his hair as she refuses to let him end the lip lock they’re engaged in until the very end. Before that end comes there’s orgasm after orgasm, her lithe body shuddering and shaking under him. Sona hadn’t ever really filled out like her sister, even after all these years. But Issei was a lover of all body types, and hers was just as good as Serafall’s, all in all.

Finally, his cock throbbing inside of her, Sona ends their lip lock in order to pull back for a second and look him right in the eye.

“F-Fill me up. Breed me… give me a-another child.”

Another would be right. It wasn’t their first, not by a long shot. Issei looks on in amusement, even as he keeps fucking her.

“You know I’ll enforce vacation once you’re far enough along, right?”

Sona flushes but nods after a moment, gasping as he picks up speed.

“Alright then… here you go.”

With a heartfelt groan, Issei proceeds to fill Sona with his seed. He pounds into her and coats her womb with his cum, making her cry out and orgasm one last time right alongside him as he fills and fills her until his balls are emptied. Pulling out of her as she limply collapses back onto the desk, Issei admires his handiwork for a moment… until Serafall’s lips wrap around his cock and she begins to suck him clean in preparation for another round.

Just from looking down into her eyes he can tell she’s decided she wants the same thing as Sona. Luckily for her, he’s more than happy to give it to her.

[X] The Phenex (Ravel, Lady Phenex) - 50%