The Sleeping Dragon Ch. 61 (High School DxD) (Patreon)

A/N: Make sure to participate in the Vibe Check post immediately proceeding this post if you want to have a say in the future of this fic!

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Jeanne had been a fairly fun fight, Issei could admit. Her Sacred Gear was Blade Blacksmith, also known as Holy Sword Creation. If he had ever taken his harem members up on their offer to try and Reincarnate him as a Devil, he actually might have been in danger. After all, she was effectively built for fighting Devils with those Holy Swords of hers.

Using her Sacred Gear, Jeanne could create any number of Holy Swords with different speeds, strengths, and even abilities. Against even a powerful Devil, she would be quite the threat. Issei didn’t know how she would have measured up against an Ultimate Class Devil, but really, that was neither here nor there. Because at the end of the day, Issei wasn’t a Devil. He was a Dragon. He and Jeanne were a poor match… for her, anyways.

Still, she’d put up quite the struggle, and proven to be a fun fight. However, in the end she’d proven to be an even funner fuck. Once he’d so easily defeated her, putting her on her back and introducing her to HIS ‘sword’ had been easy as can be. She hadn’t fought him at all on taking her right there in the middle of the battlefield, despite her choice words.

But even with how she’d constantly derided and insulted him for being an honorless pig of a bastard with a stupidly fat cock, she’d also demanded he keep going once he got started. He’d offered her the chance to stop time and time again, but Jeanne was disinclined to take him up on his offer. Rather, she was loving getting dicked down by him. Certainly, she’d changed her tune quite quickly once Issei proved how much stronger than her he was.

Even now, slamming home into her muscled, sloppy cunt from behind as he uses her hair as makeshift reins, pulling her head back and forcing her delirious, fucked silly expression on display… she’s still having the time of her life. Cumming again and again around his pistoning prick, Issei gets the impression Jeanne wants nothing more than for this to continue forever.

Le Fay Pendragon on the other hand is another matter entirely. Looking over at the blue-eyed blonde witch, Issei watches as Gabriel works her magic. His fallen lover is toying with Le Fay even now, even as the blonde trembles in her grasp after Jeanne’s words of encouragement. Gabriel might have been a pure and innocent flower mere weeks ago, but when it came to sex, she was a quick, QUICK learner. The way her hands glide across Le Fay’s body, the way she toys with and teases the smaller figure… Issei isn’t surprised when Le Fay finally breaks.

“I w-want it…”

Only his enhanced hearing allows him to catch the cute little witch’s whispered words over Jeanne’s enthusiastic cries and constant squealing. Not to mention the sound of flesh slapping against flesh as Issei takes the defeated swordswoman right there on the floor of the sparring room, pounding into doggystyle without a single moment of mercy.

From the way Gabriel’s lips quirk up in a positively wicked smile, she hears Le Fay as well. But of course, the Fallen Seraph isn’t going to make it that easy.

“Sorry, little one, what was that? I couldn’t quite hear you~”

The coaxing, cooing tone that Gabriel takes as she speaks into Le Fay’s ear makes the already red witch go downright sub-atomic, her blush out of this world as she shakes and squirms in Gabriel’s grasp. For a moment, Issei wonders if they’ve taken the teasing too far. If she chooses to go back on her capitulation and run away, then he’ll be sure to let her. He’ll even fight Gabriel for her right to choose that.

… But no, thankfully it doesn’t come to that. After a moment of whimpering and whining under the onslaught that is Gabriel’s well-practiced fingers, Le Fay cries out.

“P-Please! I-I want it!”

Even Jeanne jolts in Issei’s grasp at that, the swordswoman’s eyes snapping to Le Fay as the little witch begs at long last. Her pussy walls clench around Issei’s cock as she stops for a moment… before slamming herself back into his thrusting member all the harder. Issei lets out a chuckle and reaches down and around with his free hand, fondling one of Jeanne’s tits before ultimately turning the gentle fondle into a rough grope and maul.

“Nnngh y-you bastard… you b-better finish what you, hah, started!”

Its obvious from both her words and her actions that Jeanne thinks Issei is going to dump her like a sack of potatoes and move on to the younger model that his lover is preparing for him. But that’s just it. Gabriel isn’t done preparing Le Fay yet, and Issei isn’t done fucking Jeanne. The swordswoman honestly has nothing to worry about.

To drive that point home, Issei pinches her nipple and pulls her tit from her body, even as he fucks her even harder, even faster. Jeanne’s moaning cries fill the room, almost drowning out the exchange he picks up between Gabriel and Le Fay.

“You want it, do you? What do you want, little one?”

Le Fay whimpers at that, squirming and wriggling about quite energetically in Gabriel’s lap. Not to escape, but instead moving her body INTO the Fallen Seraph’s groping hands at this point, clearly enjoying herself immensely. However, her glazed eyes are still fixated on Issei and Jeanne, on how he’s fucking her friend right in front of her. It’s obvious what Le Fay wants, but Gabriel plays dumb all the same.

“I want… I want…”

Gabriel hums after a moment before taking mercy on the young woman.

“You want my beloved’s cock buried inside of your virgin twat, don’t you?”

Le Fay sputters and ducks her head, fresh embarrassment piling on top of the humiliation and shame she’s already feeling. But alongside all of that is burning arousal as well, and in the end she gives the slightest of nods in agreement, something that Gabriel does not fail to notice. Of course, the Fallen Seraph isn’t going to let the little witch off the hook THAT easily.

“Say it.”

Gone is the kind tone. In its place, Gabriel suddenly sounds authoritative, her voice clipped. Le Fay jolts, before whimpering and doing as she’s told.

“I want… I want I-Issei Hyoudou’s cock buried inside… inside of m-my virgin t-twat…”

Stuttering and stammering her way through the words, Le Fay nevertheless manages to get it out, even as Issei continues to rail Jeanne senseless, the blonde swordswoman’s strength rapidly beginning to wane. Her body shudders and shakes beneath him, but she’s not able to push back against his thrusts nearly as hard any longer. Instead, her form is beginning to go limp, her head only held up by his grip on her hair, her limbs starting to give out from under her.

“You want him to pound you silly, just like your friend. You want to make that face on the end of his cock, don’t you?”

The suggestion in Gabriel’s tone is obvious. She expects Le Fay to repeat her word for word again. But to the Fallen Seraph’s surprise, Le Fay hesitates for a moment before shaking his head.

“N-No…”

Gabriel hums at that, tilting her own head to the side as Issei watches on, still giving Jeanne the plowing of a lifetime.

“I want… I want h-him to make love to me. I want him to look me in the eye. I want him to… to c-cherish me.”

The Fallen Seraph rears back as if struck, before doing something that makes Issei have to bite back a bark of laughter. Gabriel… blushes.

“… I suppose you want him to hold hands and kiss you chastely as well you little vanilla-loving slut…”

Whether the Fallen Seraph intended her words to have the effect they did or not is immaterial, because Le Fay moans under Gabriel’s hands and nods her head enthusiastically, her eyes shutting as she bucks her hips and cums right there on the spot.

“Y-Yes! Yes, yes, yes!”

Gabriel, for all that she was a quick learner, looks somewhat baffled as she glances up and meets Issei’s eyes. Once again, the Red Dragon Emperor has to keep himself from bursting out laughing. In order to avoid doing so, he focuses on the matter in front of him… finishing off Jeanne. Fucking her to completion isn’t very hard, but he was never going to leave her a single ounce of room to complain.

Luckily, when he turns her head around so he can look at her face, he finds the swordswoman is very much insensate, her eyes fully rolled back in her skull and her tongue lolling out of her mouth. She looks absolutely silly, but most importantly, she’s no longer conscious. With a grunt, Issei finishes inside of the woman, spilling his seed into the swordswoman’s womb as a conqueror must towards a bitch who dared to challenge him on the field of battle.

Jeanne, even unconscious, cums one last time alongside him, her rag dolling body jiggling and shaking and shivering even as he lets go of her hair, allowing her to fall face first to the floor. As he pulls out of her, her hips continue to buck and tremble mindlessly all on their own, even as her well fucked pussy disgorges his seed all over the place.

Rising to his feet, messy cock swinging back and forth between his legs, Issei steps over Jeanne’s defeated form and begins making his way towards where Gabriel is holding Le Fay Pendragon in her lap. The blonde witch’s eyes immediately lock onto his swaying cock and she bites her lower lip as she squirms in Gabriel’s grasp.

It’s clear from the look on her face that Le Fay doesn’t expect to get any of what she asked for. And yet, still she doesn’t run. Because she wants his dick ‘buried in her virgin twat’ more than she wants all that lovey dovey stuff. She’ll happily let him fuck her silly, even if what she wanted was romance and tender affection.

Well, Issei was happy to surprise her. Instead of immediately going for Le Fay herself, Issei detours off to the side of the two of them, offering his cock to a smirking Gabriel first. The Fallen Seraph’s smirk transforms into a full blown grin and she reaches up, her thumb and index finger locking around the base of his cock to hold him steady as she leans in and takes his massive, throbbing member to the hilt in her gurgling throat.

The Fallen Seraph’s mouth and tongue are, to be a little blasphemous, outright heavenly as Issei throws his head back and groans. All the while, Gabriel still has Le Fay held in her lap, her other hand down between the blonde witch’s spread legs, fingering her juicy wet cunt quite audibly.

Gabriel shows off her skills here, getting both Issei and Le Fay off at the same time. She cleans Issei’s cock to completion and keeps him nice and hard throughout, her tongue swirling this way and that and her thumb descending down to stroke his balls as they refill for the next round. All the while, she’s got Le Fay primed and ready for whatever Issei might want to do to her.

Finally, Issei pulls away and Gabriel lets him go with one last suck. His spit-polished member is fully erect and ready to go again, and there just so happens to be a cutie in Gabriel’s lap just waiting for his attentions.

Le Fay’s eyes go crossed trying to look at his cock, and her lips begin to tentatively part, but before she can fully open her mouth… Issei kneels down, his member dipping away from her face as her gaze follows it in wide eyed surprised before snapping up to meet his eyes.

Grinning, Issei reaches out and tenderly runs a hand along Le Fay’s cheek, causing her to lean into his touch and nuzzle his hand for a moment. At the same time, Gabriel pulls her fingers free of the little witch’s pussy and uses them to spread her slit apart for him. He brings his cock up to Le Fay’s sex and slowly presses just the head of his cock into her virgin sex but stops before going any further.

Le Fay trembles at this, looking at him with wider and wider eyes as Issei leans forward and plants a chaste kiss on her imminently kissable, pouty lips. When he pulls back, his own eyes twinkle in impish delight.

“Everything you could have hoped for so far, Le Fay?”

The blonde flushes and then nods her head rapidly, only to go still when Issei moves his hand from her face… down to her hand. Slowly, he interlocks his fingers with hers, holding her hand in his own and pressing their palms together. Le Fay’s breathing comes out heavier and heavier by the moment as she watches him lift up their intertwined hands for her to see.

At the same time, Issei finally begins to push into Le Fay Pendragon’s cunt. She’s incredibly tight, but also insanely wet. Even moving as slowly as he is, he makes good progress with how aroused she already is. Still, he takes his time, not wanting to ruin even a single moment of this for her.

Eventually, he hits her hymen, the proof of her virginity and ‘purity’. Eyes still twinkling, Issei smirks as he looks at Le Fay’s red face.

“Do you want me to keep going? Do you want me to… claim you?”

“… Y-Yes. Yes, p-please…”

Issei hums and then slowly pushes deeper into her, breaking her hymen and taking her virginity on the spot. But while Le Fay’s breath does hitch for a moment, she’s moaning wantonly a second later. From having her dreams fulfilled to the way Gabriel primed her ahead of time, she’s more than eager for more even after the slight pain from having her first time.

Speaking of Gabriel… Issei looks up to meet the Fallen Seraph’s eyes, fully intending to exchange silent amusement over Le Fay’s reactions to his tender and affectionate love making. He’s not expecting Gabriel’s eyes to be as wide as the little witch’s, nor is he expecting the Fallen Seraph to be red faced and panting as well. And the cherry on top? Gabriel is staring at Issei and Le Fay’s interlocked hands, rather than the place where the two of them are joined together.

Huh, so Gabriel is weak to this kind of thing, is she? Well, with his cock now inside of Le Fay, he has another free hand. Grinning impishly, the Red Dragon Emperor reaches out, down past Le Fay to where one of Gabriel’s hands sits. He intertwines his fingers with her as well, causing the Fallen Seraph to jolt as she finds herself holding hands with her beloved.

Hm. You know, he should probably use this opportunity to get Le Fay to squeal on just why her and Jeanne are really here, to get all of the sordid details and fill in the gaps in his and Gabriel’s knowledge. But would that really be fair? Maybe it could wait for later. Maybe he should make this moment all about Le Fay’s pleasure and happiness…

He wasn’t sure he had it in him to play bad cop with the uniquely vulnerable witch right now. And he couldn’t very well expect Gabriel to do so either.