A Night of Tentacles (High School DxD) (Patreon)

Poll Winner

Themes: Tentacle Sex, Fucked Silly, Rough Sex

Summary: Rias Gremory's weeb nature gets the better of her. She loves Japan with all her heart and she loves everything about it's perverse nature as well. She even loves the fictional stuff that humans in Japan think could never happen to them in the real world. Well, maybe it couldn't happen normally... but it's not hard for Rias to procure a certain vial filled with a certain substance. All she has to do is add some of her own pussy juices and the resulting tentacle monster will rail her all night long~ 

-x-X-x-

“Heh, how was your meeting with Sona, Rias?”

Letting out a groan, Rias flops down on one of the couches in the Occult Research Club and slaps her hands over her face.

“That bad, huh?”

Under normal circumstances, the Gremory Heiress would make every effort to present a calm and dignified manner… if any of her other peerage members were actually here right now. But Sona had held her hostage for so long that it had gotten late and everyone else had gone home! In the end, the only one left waiting for her back at their clubhouse was Akeno Himejima, Rias Gremory’s closest confidante and faithful Queen.

Theirs was a relationship that beggared definition. In the end, she could truly be herself around Akeno, and so she doesn’t try to hide just how much of a drag Sona was today.

“It was aaaawful, Akeno! She’s always so serious! Ugh, and intense! And all about the silliest of things!”

“… What was it this time?”

Groaning in remembrance, Rias just shakes her head.

“I don’t wanna talk about it. I just… don’t.”

Chuckling in understanding Akeno comes over and pats her Mistress’ leg.

“Well, you probably should have known she would try to get back at you somehow for forcing her to keep the school uniform’s skirts so short. They are a tad… scandalous, you know.”

Rias lets out another groan at that. Akeno is right… but also not.

“If it were just that, I’d agree with you Akeno. But I don’t even think it’s about revenge for her! I think she’s just like this! Always!”

“… Huh. Well that sucks.”

Finally removing her hands from her face, Rias gives Akeno a glare. Really? That was all her Queen had to say? ‘That sucks’?! Rias’ cheeks begin to puff out in a way Akeno knows full well is the prelude to her best friend and Mistress blowing a gasket and assigning some sort of punishment. And not the sort of punishment that the S & M Queen likes either.

Thinking quickly, Akeno rapidly endeavors to change the subject.

“Oh! Package came for you while you were away!”

Abruptly, Rias goes still. Then, she sits up on the couch.

“Package? What kind? Big? Small? Where is it?”

Gesturing over to a nearby table, Akeno shrugs.

“Pretty small actually. It’s right there.”

Rias all but zips over to the package, looking it over. Then, she hums and nods.

“… Thank you Akeno. That will be all.”

“Oh? You sure, Rias?”

“Yes. Thank you for waiting for me all this time, but you are dismissed. Have a good night and I will see you tomorrow.”

“… Very well then, Buchou. See you tomorrow.”

-x-X-x-

Soft moans fill her bedroom as Rias squirms on her bed. Finally… finally it had come. In a heartbeat, she’d forgotten all about the pain in the ass that was Sona Sitri. Her fellow caretaker of Kuoh Academy as well as Kuoh Town could be SUCH a bore sometimes… but it didn’t matter anymore. For the thing that Rias had been waiting for… had finally arrived!

Sliding her fingers in and out of her pussy, the busty, naked red head mewls as she gets herself nice and worked up. Her other hand, meanwhile, holds up a vial filled with glowing purple liquid.

See, Rias Gremory was a Japanophile. Otherwise known as a total fucking weeb if you wanted to get derogatory about it. She loved Japan and all of its culture. She loved it so much she’d begged her parents and brother to be able to go to school there. She even… she even loved the fictional stuff that the creative Japanese humans had managed to come up with.

Well, fictional in their eyes anyways. After all, if you asked the average Japanese person on the street if they thought tentacle porn was real, they would probably laugh and call you crazy. Or maybe scowl and call you crazy, it depended who you asked. Yes, as far as the mundane humans of Japan were concerned, tentacle porn was a hentai-only endeavor. Because tentacle monsters didn’t exist. Sure, there were octopi and squids, but they had no desire to use their tentacles to penetrate human women, so it didn’t count.

But that was just the mundane world. The supernatural world on the other hand… THAT had options. And Rias Gremory, being the consummate Japanophile that she was, had decided she was going to experience one of those options. It hadn’t been particularly difficult to procure the necessary ingredients. There were sellers for all sorts of fetish things in the Underworld, after all.

Doing it without anyone catching wind of it was a little more difficult, but Rias was pretty sure she’d managed that as well. And finally… finally, here she was. Holding a vial filled with the ingredients to make her very own tentacle monster. In fact, the vial was only missing one thing now in order to activate those ingredients. The pussy juices of the tentacle monster’s ‘target’.

Her fingers are sopping wet by this point and Rias’ pussy is drooling in anticipation. As she drives her digits in and out of herself… she decides she’s ready. She wants it. She NEEDS this. Pulling her fingers up out of her pussy and bringing them to the opening of the vial, Rias scrapes her own bodily fluids off on the rim of the vial. Slowly, her pussy juices drool down the inside of the glass… and make contact with the glowing purple mixture.

Almost immediately, the vial begins shaking in her hand. Squeaking, Rias tosses it away from herself. She’d forgotten that the instructions said not to be holding the vial when you applied the activation ingredient! As the vial flies through the air and hits the ground, Rias feels a spark of horror and fear that it’ll break and somehow fail to produce what she’s hoping for.

Scrambling from the middle of the bed to the edge, Rias looks down at the floor… to see nothing at all. Wait, what?

“Huh? Where’d it go?”

Maybe it had rolled under the bed. Going prone, Rias scoots herself over so that she’s half-upside down and can look under the bed for the glowing vial. However, she doesn’t see the telltale purple glow anywhere, much to her surprise. Until suddenly, she does. But not just one purple glow. Two of them. Blinking.

Rias blinks herself, even as her enhanced devil eyesight rapidly adjusts to the pitch black darkness under her bed and she sees not just those purple glowing eyes… but also a writhing mass of what can only be described as tentacles.

“… It worked.”

That’s all Rias manages to get out before the tentacles that had slowly been creeping up either side of her bed behind her finally reach the top and lash onto her legs. Squeaking, the red head looks back to see what’s happening, her eyes widening in surprise, fear… and no small amount of lust.

In the span of a moment, Rias finds herself ripped up off of her bed and into the air. More tentacles, thicker and larger, move to join the first few, until she’s held aloft by a dozen appendages. Wiggling and squirming, the naked and busty devil moans as she feels the constriction of the fleshy tendrils. Sure, she might not be as much of a bondage S&M freak as Akeno, but this was still pretty hot. Especially since… well, there was no escaping it now, right?

Rias giggles in excitement, even as her freshly created tentacle monster slowly crawls out from under her bed. Eyes glowing with purple malevolent lust, it rises itself up so that she and it are ‘looking’ at one another. Rias pants noisily and lustfully, even as she licks her lips.

“Going to… going to fuck me now, Mr. Tentacle Monster? It’s okay. I want it. I want you to give it to me. I want-mmph!”

Rias moans as a tentacle is shoved into her yapping mouth, shutting her up. She knows, deep down inside, that the monster isn’t actually intelligent. It’s not even really alive. It’s a potion-generated construct and will fizzle out before tomorrow morning. Until then, its kind of like a human computer program. It has very specific instructions ‘hard-coded’ into it, and it will follow those to the letter.

Still, she likes to imagine that the tentacle is shoved into her mouth and down her throat in order to shut her up out of annoyance, rather than just the tentacle monster acting on its prime directive, which is to plug her every orifice with its tendrils and fuck her until it dissipates.

“Gagkh! Gagkh! Gagkh!”

Even as she finds herself being face fucked by the creature… down below, it’s also started to grope and squeeze her tits, wrapping her fat milk jugs up in its appendages and giving them a good, hard tug as she shudders in abject delight. And further below than even that, its forcibly spreading her legs apart with some of its medium-sized tendrils, so that some of the larger tentacles can press up against her lower holes.

For the first time, Rias feels a slight bit of insecurity, as she feels the huge, bulbous heads of those tentacles pressing up against her cunt and ass. Sure, she was sopping wet. Sure, she’d made sure to lubricate her asshole as well before doing all of this. But even still… were those tentacles going to fit?!

In the end, it’s not like the tentacle monster cares about her fear though. Indeed, the humungous tentacles at her lower holes punch up into her without so much as a ‘by your leave’ and certainly not an ounce of hesitation.

“MMMMPH!!!”

Rias squeals and screams around the one in her throat, even as she bucks and shakes and spasms in the air, held aloft. Her eyes threaten to roll back in her head and they very much DO go crossed as she shudders from the sudden impalement. It feels… amazing. Belatedly, Rias dazedly remembers that she really had nothing to worry about. Satisfaction was guaranteed by the company who sold her the vial.

Indeed, even if the tentacles SEEMED to be too big… they would always wind up being just big enough to make you feel like you were going to explode, but not big enough to do any actual harm. Rias shudders and quivers, her toes curling as the tentacle in her cunt punches right into her womb itself in no time at all. Meanwhile, the one in her ass is sliding through her bowels.

In that moment, Rias Gremory has achieved two of her lewder dreams. Number One, she’s being fucked by a tentacle monster. Number two, she’s managed to do what humans on the internet call ‘being made airtight’. All three of her primary orifices are stuffed with fleshy tentacles, and all she can do is take it as her eyes roll back and she gurgles around the one in her throat.

Of course, the tentacle monster doesn’t let up just because she’s achieved her dreams. That would be ridiculous. The potion construct has one purpose and one purpose alone… to give Rias a night of pleasure and ecstasy that she won’t soon forget.

Gurgling muffled moans are drowned out by the sound of squelching as tentacles drive in and out of her holes. Rias’ body, already helpless in the creature’s grasp, is soon limp and ragdoll-like as she’s fucked and fucked and fucked. The tentacles also come coated with a slime of their own that induces further arousal in the woman, according to the product guidelines. Rias can believe it, because it’s not long before she’s cumming her brains out and just can’t stop.

Eyes fully rolling back in her head, tongue swirling around the tentacle in her throat, and pussy and ass made into the monster’s playthings… Rias Gremory lets go and enjoys the night for what it is. A long, hard dicking from the tentacle monster of her dreams. Shuddering, shaking, spasming… the Gremory Heiress is shown the depths of a forbidden pleasure as her holes are ravaged and ravished nonstop by tentacles. And as she learns what it means to truly be in a hentai, Rias gurgles happily and just goes along for the ride.

-x-X-x-

“Rias? Buchou? I know its Saturday, but you weren’t answering my texts…”

Akeno Himejima feels a little self-conscious intruding upon her Mistress’ bedroom without permission… but at the same time, they have that kind of relationship. So in the end, Rias’ Queen finally pushes open the door to her best friend’s bedroom, only to freeze at the entryway as she stares in shock and awe at the sight before her.

There, on the bed… is a naked Rias Gremory, arms and legs splayed out in a very lewd and provocative manner. Her eyes rolled back in her head and her tongue lolling out of her mouth in a constant ahegao, Rias’ body twitches and shudders every so often. But that’s not all. No, Rias is also covered in this purple goo. It’s all over her, and mostly centered around her cunt, ass… and mouth. She looks bloated, like someone… or something has cum inside of her multiple times.

Finally, Akeno regains herself and hurries to Rias’ side.

“Buchou! Rias! Are you alright?!”

Who could have done this to her? What could have? Should Akeno go and get help? But thankfully, before she can leave the room, Rias’ eyes snap forward in her head and Akeno’s Mistress regains a semblance of cognizance.

“A… Akeno?”

Nodding her head, feeling tears welling up in her eyes, Akeno grabs Rias by the hand, uncaring of how sticky and slimy her Buchou’s palm is.

“Its m-me, Rias. I’m here. Who… who did this to you?”

“Mm… I did this to me. It was… amazing.”

Huh? Caught off guard, Akeno can only blink in stupefaction. But she is nothing if not a doting Queen and a faithful friend. So she listens as Rias describes what she’d done, the vial she’d ordered and how she’d created her own temporary tentacle monster to enjoy a long night held aloft in its not so tender appendages. Akeno is flushed by the time her Buchou is done explaining… and she’s clutching at Rias’ hand none too softly.

“Akeno… w-why are you holding my hand so far? Akeno… you’re hurting me!”

“Rias… how could you do something so foolish, reckless, and stupid… without me?!”

Pausing, her Mistress gapes at her for a moment… before blushing.

“Ah… sorry?”

Akeno scowls angrily, making it clear that sorry won’t cut it.

“… I’ll let you join in next time?”

That was more like it!