(Every character depicted in the story below is a consenting legal adult over the age of 18)

Poll Winner

Themes: Titplay, Big Dick, Fucked Silly

Summary: In an AU where they don't tell Rias about her engagement to Riser until she's eighteen, Rias is so furious that she's willing to go as far as propositioning the town's biggest pervert and lech, offering to let an eighteen year old Issei Hyoudou do whatever the fuck he wants with her body. She's not expecting to get her world rocked by his fat fucking cock, but afterwards she's happy to make him a Devil right then and there so she can ride his dick forever.

-x-X-x-

“… And this really isn’t a prank?”

Rias huffs, a mixture of amused and bemused as she gives Issei Hyoudou a rueful look.

“No Issei, this isn’t a prank. It’s very real. Have a seat and we’ll… begin~”

Swallowing hard, Issei looks around the room a final time, like he’s hunting for hidden cameras or something. Then, he fixates back on her again… specifically on her ‘oppai’. Suffice to say, after a moment of staring at her tits, he sits his ass down at the end of the bed that dominates one side of the room. Rias just smirks.

He’s not entirely wrong to be concerned. After all, why would someone like her ever do something like this with someone like him? In fact, Issei isn’t even entirely wrong about it being a ‘prank’ of sorts. It’s just that he’s not the recipient of the prank, he’s simply the tool by which Rias is pranking everyone else.

With Issei seated on the edge of the bed, Rias moves in front of him and begins to sway her body and swing her hips. Immediately, Issei’s eyes are drawn to her chest again as they jiggle and bounce with her purposeful movements. Meanwhile, the sundress she’s wearing swishes back and forth while doing absolutely nothing to truly hide her curves. Her voluptuous eighteen year old virgin body is practically on full display… or will be soon.

Reaching down, Rias grabs ahold of her sundress and slowly begins to tug it upwards, hiking it up inch after inch. Issei’s eyes immediately drop from her chest to her legs, watching as inch after inch of her naked flesh is revealed to him. Until finally, Rias is teasing him with a view of her inner thighs and the promise of even more than that.

Finally, with a flourish, Rias yanks the sundress up and over her tits and head, letting her massive chest drop heavily down and bounce for a good solid dozen seconds as she pulls the dress completely off of her and flicks it to the side.

Issei’s jaw drops open, his eyes widening to the size of dinner plates as Rias… exposes every last inch of her body to him right then and there. She’s not bothered with panties or a bra. After all, she’s always preferred to go commando anyways. It’s why Rias sleeps naked, because clothes feel too restrictive and too many layers of clothes are just the absolute worse.

Given what they’re here to do today, she saw no reason to bother with underwear. It would just get in the way.

“Like what you see Issei~”

Her teasing voice as she runs her hands up and down her body causes Issei to nod rapidly, his eyes still wide. His slack jaw does finally close with a click though and he swallows hard, his hands twitching at his side.

“Y-Yes… yes, I like what I see. I want… I want to touch you…”

Rias giggles.

“You’ll have plenty of time for that in just a bit Issei. In fact, you’re going to be touching me as much as you want. But first… let me touch you, hm? Let me get you ready~”

Swallowing hard, Issei nods again, watching as Rias approaches him and the bed. His eyes follow her down as she descends to her knees, her breasts bouncing once with the sudden movement and then jiggling to a stop. Rias smirks and reaches out for his belt buckle, deft fingers working quickly to extract his cock from its confines.

Not that Rias is too worried about any sort of timetable they might be on. She’s prepared for this, after all. Today… nobody will interrupt them.

Ever since finding out that she was supposed to marry Riser Phenex on her eighteenth birthday, Rias has been… beside herself. Not only had her parents ruined her birthday party with the news, but they were also trying to ruin her life… to say nothing of her beloved peerage.

Rias wasn’t going to let Riser get his hands on Akeno or any of the other girls who she considered under her protection. Nor was she going to let Riser get his hands on her. In the end, there was only one option available to her. Only one way to ruin the engagement and make sure it was called off. Even if it got her disowned by her family… she honestly wouldn’t mind.

Of course, if she was going to get herself despoiled ahead of her wedding day, it couldn’t just be anyone. She refused to allow it to be swept under the rug. That’s why… she’s here with Issei in this room in the depths of a Love Hotel. A room that Akeno had paid a local human magician to come and ward against detection ahead of time.

Once it got out that Rias had lost her virginity to Kuoh Town’s biggest pervert, there was no way she would be marrying Riser. The wedding would be called off, the engagement broken, and the entire ordeal would be over… one way or another.

These are the thoughts running through Rias Gremory’s mind as she slips a hand into Issei’s boxers and wraps her fingers around his cock for the first time. She’s not thinking about how this might feel, or what he might be like in bed. In fact, she’s not expecting much of Issei at all in that department.

… Which is why it’s such a shock to her when she feels the size of his cock for the first time. Surely she must be misjudging, right? Except no. When she pulls Issei’s dick out into the artificial lighting of the Love Hotel, Rias lays eyes on it properly… and what she felt through touching it was in fact not a misconception at all.

He’s huge. And he’s getting bigger. Rias swallows thickly, her mouth suddenly paradoxically both dry and watering as she stares down at Issei’s twitching, growing, throbbing mast. He’s quickly growing too big for her to even wrap one hand around properly.

“Rias? You alright?”

“Y-You’re so… b-big~”

Issei flushes and lets out a sheepish laugh.

“Ah… yeah, sorry. I know hentai gets that part wrong. Most girls don’t want a dick this big… it hurts them, after all. If you want to call this whole thing off… its alright. I get it.”

He wasn’t wrong. Issei Hyoudou was hung like a motherfucking stallion and if he tried to use this behemoth of a bitch breaker on a normal human woman, Rias had no doubt that it WOULD hurt like nothing else. However… she wasn’t a normal human woman, was she? And all she can do as she stares at his growing, throbbing mast is clench her thighs together in sheer NEED.

“N-No… no, we’re not… we’re doing this. I can take it, Issei. I can take you~”

But first, she needed to prepare him. Only, he’s too big for her to use just her hands and mouth. Luckily, she has the proper assets for a monster cock of this size. Forcing a confident smirk onto her face as she looks up at Issei, Rias proceeds to grab her massive pillowy tits and lift them up to wrap them around his throbbing dick.

He’s huge… but to be fair, Rias has the biggest pair of breasts she’s ever even seen. Not even her mother holds a candle to her. Akeno gets close, but not her either. Rias’ tits are the female equivalent of Issei’s dick… and so she’s able to fully wrap her chest around Issei’s shaft, completely enclosing his hot, heavy member in her cleavage.

Issei groans, tossing his head back in pleasure.

“Shit… Rias… your oppai really are perfect. I-I always knew they were but now… now I get to experience them directly! This is the best day of my life!”

Rias giggles, her eyes twinkling in amusement as she licks her lips. Truth be told, this was shaping up to be more fun for her too than she had initially imagined. As she begins to slide her chest up and down his cock, Rias leans forward and opens wide, beginning to French Kiss the bulbous head of Issei Hyoudou’s dick as it pushes up from between her breasts.

From there, she develops something of a rhythm over the next few minutes. Rias swirls her tongue along Issei’s glans while squishing her breasts all across his hot shaft. Issei, in turn, tilts his head back and groans, thoroughly and vocally enjoying Rias’ efforts.

She knows she needs to make him cum with her tits. Why? Simply out of pride if nothing else. So Rias keeps at it, going as hard as she possibly can until Issei’s groans change in tone. And finally…

“Rias… I can’t hold it back! I’m cumming!”

He grabs her by the back of her head and pushes her down on his cockhead just as he tips over the edge. Rias doesn’t mind the forcefulness though. In fact, it’s kind of hot. Especially as his seed explodes into her mouth and then back out again, spraying all over her tits and lower chin and his cock.

She tries to swallow what she can, but ultimately she fails… his load is as ridiculous as his cock size and by the time she’s done, Rias is coated in his jizz despite holding his bulbous dickhead in her lips the entire time.

Issei, panting, stares down at her like he fucked up or something.

“Ah… I’m sorry, I didn’t-!”

But Rias cuts him off with a laugh as she pulls back, waving him away.

“You didn’t do anything wrong, Issei. The only reason you would have to apologize is if you failed to do the job of taking my virginity. But seeing as you’re still hard, that shouldn’t be a problem right?”

And indeed, Issei is still at fully mast despite cumming. Rias can hardly believe her eyes… but she’s not about to question it. All that matters at this point is to get what she came for. Climbing up onto the bed, Rias gets on all fours with cum dripping from her face and tits. She waves her ass in the air, her breasts jiggling under her as she spreads her kneeling legs nice and wide and invitingly.

“Come on Issei. Fuck me like this. Make me your bitch~”

After all, what better way for the Gremory Heiress to lose her virginity than in such a… plebian position like doggystyle? Being taken from behind, treated like nothing more than livestock… it would be perfect.

Issei certainly seems to agree as he immediately hops up and gets on the bed on his knees behind her. His hands grab her hips, his cock presses against her slit and his breath hitches.

“You… you’re sure you can take my size, Rias?”

Rias laughs.

“Let’s find out, Issei~”

With that, she thrusts back with her hips, causing Issei to yelp as her pussy lips spread slightly over his bulbous cockhead. And then… it’s like he’s reached the point of no return. With a low, primal growl, Kuoh Town’s greatest pervert (and most hung stud apparently) slams forward with every last inch of his cock all at once.

He thrusts into Rias without any further warning and plunders her virginity like it’s almost an afterthought. She loses her virginity as planned, but it barely matters in the face of what happens next as Issei lets out a shout and begins to fuck Rias Gremory from behind like she really is nothing but a common bitch.

WHAP! WHAP! WHAP!

His huge ball sack slaps up against her clit and pussy mound with every thrust even as every last inch of his gargantuan fat hog of a cock stretches her virgin walls like there’s no tomorrow. Rias’ eyes widen… and then fully roll back in her head, her tongue lolling out of an open mouth as she ahegaos within seconds of penetration.

Issei’s big fat cock doesn’t just drive her wild… it opens her eyes to an entirely new world of pleasure. Everyone looked down on him for his perverted ways, but none of them knew what they were truly missing. Rias herself didn’t know what she was truly missing… until now~

Cumming her brains out is only natural in the face of all that. Issei fucks her, Rias squeals happily, and climaxes again and again. The sounds of flesh slapping against flesh mix with Rias’ wanton moans, loud cries, and ugly squealing as she orgasms repeatedly all over his pistoning prick.

Issei doesn’t hold back. Once he starts its like he can’t stop until she finally understands her place. He knows nothing about her true background. But Rias feels like it wouldn’t even matter if he did. Even if he knew she was a Devil and the Heiress to the Gremory Clan, he wouldn’t care. He’d still treat her exactly as she deserved to be treated, like the wanton woman she is.

Admittedly, she loses track of time a little bit somewhere in the midst of all the pleasure he’s drowning her in. She can’t even remember how many times she cums for him before he finally tips over the edge a second time and unloads with another huge helping of hot, sticky seed, this time directly into her quim.

By the time Issei is done cumming, Rias is left a twitching, quivering, thoroughly fucked mess. And yet, as he pulls out of her and drops onto his back on the bed next to her to recover his breath… she’s not fully satiated. No, Rias finds herself wanting more. She wants…

“Issei Hyoudou… join my peerage.”

“Huh? Wuzzat?”

Giggling, Rias looks over at him and manifests one of her remaining Evil Pieces, a pawn, in a flash of light. Issei’s eyes widen at the ‘magic’ and then widen even further as Rias explains… everything while they lay there naked and sweaty. When she’s done, Issei makes a curious noise in the back of his throat.

“So you’re saying… I can become a Devil, live forever, and get to fuck you whenever I want?”

Rias just smirks.

“Yes. And if you get strong enough, you can even earn your own peerage and fill it with even more women to fuck.”

Issei’s eyes glitter with greed.

“Alright. I accept.”

In the end, it takes not one pawn, but eight pawns to Reincarnate Issei Hyoudou as a Devil. Rias later finds out this is because he’s actually been the Red Dragon Emperor all along. Who fucking knew?

Also it turns out giving her virginity to the Red Dragon Emperor is seen as a ‘tactically sound decision’ by a Pillar Heiress, so Rias not only gets her engagement to Riser annulled but also keeps the full backing of her family throughout the process.

… All’s well that ends well, Rias Gremory supposes.