It’s not long after his encounter with Tsubaki Shinra that a letter requesting his presence arrives. However, to Issei’s surprise, it’s not a letter from Sona… but instead a letter from one Rias Gremory. The red head seems to have finally gotten around her nervousness, and actually went ahead and sent him an invitation to meet with her after school at the Occult Research Club… alone.
 
The letter further went on to state that Rias had every intention of making things… worth his while. In the end, that last bit was the only real reason that Issei bothered to head on over after school was finished for the day. Arriving at the Occult Research Clubhouse, he found the door to be unlocked, and following the hallway eventually led him to what was obviously a common room. Said common room was occupied by a petite young woman that Issei knew as Koneko Toujou, and a handsome young man that Issei knew as Yuuto Kiba.
 
They both tense up at his sudden appearance, but in different ways. Koneko suddenly seems keenly interested in him, leaning forward like a cat ready to pounce as her cute little button nose sniffs at the air, clearly catching his scent very late. Kiba, meanwhile, seems on guard, defensive to the extreme, brow furrowed and hands moving as if he’s about to draw weapons that don’t exist.
 
The girl is Nekomata, and if she spends too much time in our presence, she just might go into heat. The boy is clearly a swordsman… perhaps he even styles himself a Knight in Shining Armor. Been a while since I’ve burnt one of those to a crisp.
 
Ddraig’s tone is rather bored in Issei’s head, even as the young man gives no outward inclination of his constant companion’s words. Instead, outwardly he simply raises an eyebrow at the two obvious devils.
 
“Your mistress sent a letter asking for me. Did she not tell you?”
 
Koneko’s pupils are getting more and more dilated, and her lips are parted as she begins to pant. In the end, Kiba is the one who actually answers, grimacing as he gives a stiff nod in response.
 
“… She did.”
 
Issei hums at that, but before he can say anything else, Rias Gremory herself sweeps into the room, looking a bit harried, as if she was in a rush. She stops upon seeing what’s going on, her eyes wide for a moment before she latches onto Koneko’s state.
 
“Kiba, be a dear and remove Koneko from the clubhouse, please. I require absolute privacy with my guest for at least the next hour, possibly longer.”
 
Another grimace from Kiba, another stiff nod. In the end, the swordsman or would-be knight, whatever he is, obeys his mistress and grabs Koneko, dragging the still-staring Nekomata out of the room. Issei watches the two leave, wondering if Rias was fast enough or not. He supposed he’d know if he found himself dealing with a cat girl any time soon.
 
With them gone, the Red Dragon Emperor turns his full focus onto the Gremory Heiress and watches as Rias’ knees buckle ever so slightly, her own lips parting and her face flushing as her eyes grow ever so slightly hazy with arousal. Not as bad as it was getting for Koneko, but it’s clear to both of them what Rias truly wants from him. Still, he wants to hear her beg, if he’s being honest. He’s not going to make things easy for her.
 
After a beat of silence, Issei gestures to the couches and table in one area of the common room.
 
“Shall we sit down?”
 
Rias flushes a bit more, this time in embarrassment that he’s the one having to ask, when it’s her place and she’s the one who invited him here.
 
“Y-Yes, please have a seat.”
 
Issei shrugs and does so, noting that Rias does not sit across from him. As he looks at her standing there, she fidgets for a moment before giving him a wan smile with just a hint of arousal in it.
 
“I, u-um… I did promise to make it worth your while, did I not? I-If you came and s-spoke with me…”
 
Issei nods. She did indeed, and he would be lying if he said he wasn’t curious as to exactly how she planned to do that. Rias though, obviously had ideas. Fidgeting slightly, but also smiling rather perversely, the red head reaches up and begins to unbutton the blouse of her school uniform, right in front of him.
 
Watching in silence, the young dragon takes in the view, even as it grows more and more appealing. There’s no denying that Rias Gremory is absolutely stacked. No denying that she might just be the sexiest, most buxom, most voluptuous young woman in all of Kuoh Academy. So, having her expose her bra-clad chest to him, and then go a step further by unclasping said bra and pulling it off… well, that certainly had Issei’s member growing almost painfully hard in his pants.
 
Her bountiful breasts should have had a bit more sag to them from the sheer weight, but they were instead impossibly perky, sitting higher on Rias’ chest then should have been possible. Perhaps the Underworld’s gravity just operated differently then the normal world? Or perhaps her devilish physiology kept her from losing her perkiness too fast from the overweight mammaries she was supporting.
 
Either way, Rias Gremory’s breasts are without a doubt, the most beautiful pair Issei has ever had the pleasure of seeing. Things only get better when the red head makes her way over to him, now half-undressed, and kneels between his legs. With single-minded focus, the Gremory Heiress reaches out and begins to unbutton and unzip his pants, sliding a hand into his boxers and taking hold of his thick cock. Slowly, she pulls it free, her breath hitching as she gazes upon it.
 
“Akeno wasn’t wrong when she spoke on how impressive you are, Issei…”
 
Rias’ murmur is accompanied by her looking up at him and offering her most seductive smile. Issei’s practiced eye still notes the uncertainty and trepidation behind it though, no matter how much Rias tries to hide both. He simply continues to watch her, and in his silence, she moves on, shifting up to her full kneeling height and lifting her massive tits to wrap them around his cock.
 
It’s nice and warm, as she begins to slide her boobs up and down his member. There is some initial friction at first though, and wincing, Rias spits a bit at the valley of her breasts where his large schlong is poking out, trying to provide some lubrication. His own precum eventually begins to leak out of the tip of his cock and do the same, ultimately slicking the passageway as Rias continues to give him her best tit fuck. It’s obvious that the girl is inexperienced, which means that Issei is likely the first man that she’s ever used her absolutely amazing rack to pleasure. How… thrilling.
 
“N-Now then… I suppose you’re wondering why I asked you here.”
 
Ah, so this was it then. Rias had indeed managed to make his presence here worthwhile. Now he would hear her out and see what exactly it was she wanted from him.
 
“I am. We already spoke before, about how I cannot join your peerage. I hope this isn’t more of that.”
 
Rias smiles slightly and shakes her head, even as she continues to slide her tits up and down his length, wrapping her breasts along his cock, pinching and pulling at her own nipples, when she’s not just grabbing handfuls of her prodigious titflesh and pushing them together. It’s obvious that she’s getting into things the more that it goes on, her breath becoming uneven.
 
“N-No… I understand why that… that wouldn’t work. I w-was hoping to ask you for something else, Great Dragon.”
 
Issei cocks his head to the side at that, eyeing her even as she flushes and pants breathlessly, almost seeming to get off on giving him a boobjob even more than he’s getting off on getting one.
 
“Oh? And what would you ask of me, Devil?”
 
Biting her lower lip, Rias is silent for a moment, clearly trying to find the words. Eventually though, she speaks.
 
“I… I am engaged to another devil, by the name of Riser Phenex. I do not love him. I do not want to be with him. Arranged marriages are a fact of life among the Seventy-Two Pillars… but perhaps I am simply a romantic by nature. I wish to find love. I wish to at least have the choice of who I will be with.”
 
Humming, Issei doesn’t reply right away. When Rias doesn’t go on though, instead focusing on tit-fucking his cock with her impressive breasts some more while looking at him expectantly, he waves a hand in the air.
 
“And? What do you want of me?”
 
Flushing, Rias ducks her head.
 
“O-Oh, right… I wish for you to fight him on my behalf. If I try, there will be a Rating Game. My peerage and I… I love them with all my heart, but Riser has a full peerage, and much more training than I do. In a Rating Game, I would surely lose. But if you were to be my Champion instead and challenge Riser to a duel for my marriage contract, then… then you could defeat him easily, and I would be free.”
 
Rias is panting heavily now, breathlessly, and Issei isn’t sure if she’s already orgasmed once from giving him a titjob, or if she’s about to, but it’s obvious that she’s even closer to release then he is, despite neither of her hands sliding down to her crotch a single time during their conversation. It was becoming increasingly clear that the red head’s massive chest was incredibly sensitive. It left him wondering just how she managed to get through the day with such a prodigious rack bumping against everything, and constantly rubbing against the strained fabric of her school uniform.
 
Still…
 
“Would you be free? It sounds as if you would be mine, if I were to win you from this Riser.”
 
Rias blushes profusely at that, and for the first time since she’s begun, stops and hesitates. She gives him an altogether shy look, one that doesn’t exactly belong on the face of such an adventurous and outgoing girl… even if Issei has already pegged her as a virgin.
 
“Would… would that be so bad?”
 
Issei blinks at that, even as Rias bites her lower lip hard and gazes up at him, still continuing to slide her breasts up and down his impressive length.
 
“You would have to claim me, in order to act as my Champion, wouldn’t you Great Dragon? As you’ve made perfectly clear, I cannot have you in my peerage. But… perhaps you will take me for your burgeoning harem instead. Take me, claim me, conquer me… and Riser will have no choice but to duel you in an attempt to regain my lost honor… and his. Ravish me, ravage me, ruin me so that neither he nor any other man my parents pick for me could ever compare, ever again.”
 
By the time she’s done monologuing, Rias’ eyes are hooded with abject lust, and she looks like sex personified, clearly eager beyond belief. With only a beat more of hesitation, the red head abruptly leans forward, craning her neck and opening her oh-so-fuckable lips nice and wide as she sucks the head and first couple of inches of his thick prick right into her mouth.
 
The entire time, Rias keeps her eyes on his face, even as she lewdly and sluttily sucks at his cockhead as hard as she can, while at the same time continuing to slide her breasts up and down the rest of his length. There’s no denying that the scene is incredibly fucking hot, and Issei grunts, drawing ever closer to a release.
 
Well… the girl certainly knows her stuff. She’s not going into this with any misconceived notions. No… she knows what she wants, and she knows what she has to give up to get it. The only choice left is yours, Issei. Do you meddle in the affairs of devils, or leave it alone?
 
Issei snorts at that, because really, it’s not even a question, now is it? Before Rias can even fully process what’s happening, he’s moving, dislodging her from her place between his legs as he grabs her by the shoulders and yanks her up, his cock popping free of her lips and out from the valley of her breasts. The red head finds herself on her back on the table right behind her in moments, even as Issei reaches out and tears first her skirt, and then her panties off of her body, exposing her gushing, dripping wet cunt to the open air.
 
Rias gasps and mewls, even as he spreads her legs wide, pulling them up by the ankles and holding them apart. His cock, fully erect and ready for action, slaps down on Rias’ cunt, along her navel and her abdomen, showing her just how far he’ll go inside of her, once he’s fully hilted. Slowly, Issei pulls back, until just the fat head of his member is pressing against her parted flower, ready to rob her of her virginity then and there.
 
But he stops, cocking his head to the side and looking down at her somewhat curiously.
 
“… What about love, though? If you belong to me, how will you find your true love?”
 
Here, Rias flushes an incandescent red that almost manages to match her hair color. She gives him a trembling smile, even as she bites her lower lip.
 
“I… with enough time, I think I could love you. I already want you with every fiber of my being. I’ve spent every night since our last meeting masturbating to fantasies of you. I’ve fed off of every tale Akeno has told me of you. For now, it is a purely carnal lust… but I believe you will treat me better than Riser would. I believe that one day, I can love you as much as I desire you.”
 
Practical girl. Just give it to her already, Issei.
 
Issei shrugs and proceeds to do just that, but before he can thrust in, there’s a sudden flash of light off to the side, and an affronted voice speaks up.
 
“Heiress Gremory, what do you think you’re DOING?!”
 
Issei turns to regard what appears to be a maid, while Rias reacts with a yelp as she suddenly struggles to squirm away from him and cover herself up.
 
“G-Grayfia! What are you doing here?!”
 
Hah! They put a warning system on the girl’s virginity! How cute!
 
“Stopping you from making a bad decision, it would seem. You are betrothed, Rias. This behavior is unbecoming of the Heiress of House Gremory.”
 
Issei just blinks, looking between Rias and this maid, Grayfia. For all that Grayfia is dressed as a maid… he can feel how strong she is. Stronger than Rias, by far. Stronger than any being he’s met so far, he’s pretty sure. Not stronger than Ddraig though. And… not stronger than him, either.
 
But on top of that, as the maid looks away from Rias and to him, Issei finds himself noticing the signs, right off the bat. Her nostrils flare as she breathes in his scent, and her entire body goes rigid for a moment. Though she manages to hide most of it, there is the faintest blush he’s ever seen now dotting her cheeks.
 
She takes one look at him, and at the situation taking place between him and Rias… and bows low, at the waist.
 
“Great Dragon, if you would… please do not rob my charge of her chastity. If you must slake your unnatural desires on anyone… let it be me.”
 
Issei finds himself staring, entirely nonplussed, even as Ddraig’s laughter rings through the back of his head. When… when did his life get so damn complicated?