บท 357: "Gentleman" Training (High School DxD)
A/N: "Gentleman" Training" was a P atreon Poll Winner originally written back in 2018, and posted to HF back in 2021. Posting it up here and now for people to enjoy!
Themes: Cheating, MILF, Fucked Silly
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"Please sit down, Issei."
Venelana smiles as the boy sits, not because he obeys, but because of how he obeys. Issei Hyoudou is a reincarnated devil with very little demonic energy to his name, but he's also the Red Dragon Emperor reborn. And more than that… he's her darling little Rias' love interest. Is it any wonder then, that the one they had once called the Brunette Rune Princess, wife to Lord Gremory of House Gremory, would take the boy under her wing and try to instill some manners into him?
She'd done as best as she could, at that. Though, admittedly, there were some aspects of Issei Hyoudou's personality that were not so easily trained out of him. While he'd learned all of the lessons she had to teach him, taking to her training with gusto and soaking up the history of the Underworld and the Gremory Clan like a sponge in water, he was still… well, himself.
And even if Rias wanted the boy, warts and all, Venelana couldn't simply allow her daughter's lover to be so uncouth. That was why today's training would be a little different.
"Issei… you have done well so far. You have learned everything I have tried to teach you. As a student, you are a motivated pupil."
Issei beams at that, and also blushes. But at the same time, he reins in his first impulse, which Venelana knows is to leap up into the air and thrust a fist skyward as he proclaims his triumph to the ceiling and his intentions of becoming a Harem King. He doesn't do this, and Venelana is honestly impressed… while simultaneously embarrassed for the boy that she can even BE impressed over something so… so… well, moving on.
"Thank you, Lady Gremory."
Smiling softly at his words, Venelana brings up a hand to her cheek and sighs.
"You're a good boy, Issei. I know that, and I know you'll be good to my daughter too, when the time comes… however."
And here is where she changes things up. Venelana has a tendency to wear dresses that show off an expansive amount of her upper chest and her cleavage. Straps usually hold up her dresses, rather than sleeves. As such, its quite easy indeed for the brunette devil to reach up and slip the lacy straps of her dress off of each of her shoulders.
Issei's eyes bug out of his skull as Venelana lets the top of her dress fall off of her breasts entirely, releasing them from their already-loose confines and exposing the perfect pair of massive jubilees to the gaze of her daughter's choice. Rias gets her expansive chest from somewhere after all, and its NOT her father, heh.
Of course, even with her breasts exposed, Venelana sits with the same poise and grace as before, the same soft, lady-like smile on her face as she rests her hands down in her lap and watches Issei struggle with… well, everything. Eventually, he manages to control himself, much to her relief, though he can't look her in the eye, choosing instead to look away entirely.
Venelana is relieved, not because she feared the young devil or anything like that, but because if Issei had reacted in any way save this one, she would have had to punish him most severely, and begin his training all over again. As it is, this response is what she'd hoped for. And that means they can continue.
"Do you like what you see, Issei? Have you seen breasts like these before?"
"… Y-Yes Lady Gremory… t-to both questions."
Of course. Rias did have that naughty habit of sleeping naked that Venelana simply hadn't been able to train out of the girl before she went off to study abroad. It was unfortunate, but Venelana had honestly considered it the least of her worries. Now though, it seemed Rias' naughty habit had turned into lewd teasing that had probably driven poor Issei up the wall.
"You may look, young man. You may not touch."
Issei's eyes flicker over to her and then stay fixed on her tits as Venelana rises from her own chair, swaying her way towards him. She stops in the middle of the space between them, her soft smile still on her face as she watches Issei's hands grip tightly at the top of his legs, which are in turn almost vibrating with NEED.
"Good, Issei. Now… take it out."
Issei's eyes widen at that.
"L-Lady G-Gremory?!"
But Venelana doesn't look away, she doesn't blush, she doesn't rescind the command. Continuing to stare into Issei's eyes, the topless beauty just keeps right on smiling.
"Take it out, Issei. We're going to begin training you in a different way now. You need to be a gentleman in bed for my Rias… don't you agree?"
"Y-Yes!"
Issei is always quick to agree with her. Venelana likes that about the boy. She watches, standing over him as he pries his claw-like hands off of his legs and shakily reaches for the button and zipper on his pants. Venelana can already see his bulge, and her soft smile takes on a slightly sharp tinge when he's not looking. Of course, her beauty would have an effect on the boy, but then that was the point of the training.
The button comes undone, the zipper comes down, and Issei pulls at his boxers with one hand as he reaches within them with the other. Then, he drags his cock out and Venelana's smile falters for the first time, her gorgeous purple eyes widening ever so slightly as she freezes up at the sight of Issei's cock. She'd… she'd never seen one unfold like that before. It was like his soft prick was PACKED into his boxers… and the more she stared as Issei let his length flop out between his legs, the more the Lady Gremory realized that was exactly the case.
"… You're not hard."
She tries to keep the wonder from her voice, and luckily Issei's embarrassment is enough to cover for her initial reaction. He's only willing to spare a glance at her before he looks away again, flushed red and still vibrating with the desire to do something that would get him a beat down if he tried it with her.
"A-Ah… no, Lady Gremory. S-Sorry?"
He doesn't sound like he's sure whether or not he should apologize. Venelana doesn't care, she's too fixated on the issue at hand.
"Why aren't you hard?"
She'd honestly assumed the boy was sporting an erection every single time they'd met these past several weeks. He'd had that bulge of his more than once after all. But this… it turned out she'd been wrong. He was just this big, without an ounce of thickness or hardness to his cock as it dangled off of his seat.
"Ah… well… it um, it takes contact, these days?"
Issei still sounds unsure, even as Venelana finds herself coming to some sort of epiphany. Issei is… he's not just a pervert, going off of Rias' stories of the boy, and what Venelana had been able to find out from other sources. He's a super pervert. Had he truly built up such a resistance to lewd things that he couldn't get hard without something like a hand or more on his big, fat cock now?
Venelana blinks, and then realizes she's been staring at Issei's soft, limp, and most importantly massive member for a solid minute in silence. Luckily, he hasn't noticed. Pressing her lips together firmly, the Lady Gremory finds herself acting without really thinking. Two more long steps take her right up to Issei's chair, where she descends to her knees and wraps her bosom around the boy's cock before he can even blink.
"Contact such as this?"
Issei yelps and rears back in his chair, but Venelana grabs his leg and holds him in place for a moment to keep him from toppling over as she watches his cock, sliding as it is between her breasts.
"L-Lady Gremory, what are you doing?!"
She doesn't answer him, all too fixated on his body's reaction to the feel of her soft, fat mammaries. His cock does indeed respond quickly to her, and Venelana's eyes light up as she feels him finally growing thick and hard between her tits. Her soft smile is completely gone by now, replaced by something much more at home on the face of one who would call themselves a devil. The Brunette Ruin Princess is coming out to play, and Venelana doesn't know if she'll be able to put her back in her box.
But… maybe she doesn't need to? Maybe… maybe this is okay in its own way. Surely her husband will understand. It's for Rias' sake, after all.
"Issei… this is all part of the training. Please, bear with me."
Its not, and this wasn't Venelana's plan at all. But no plan survives contact with the enemy, and sometimes, things change. Issei swallows thickly and nods, even as he moves his hands from his legs to the sides of his chair, clinging to it hard enough that Venelana hears the wood beginning to splinter. That just makes her smile wider still, as she looks up at Issei and watches the reactions she's causing him to have while she makes his cock nice and hard and thick between her breasts.
Of course, looking up just means she nearly gets an eye taken out when Issei's prick proves to be far larger than Venelana truly expected at full mast. The meat cannon grows into her field of view and she rears back, only to realize even HER massive breasts can only really cover up the lower half of the base of Issei's giant prick.
"L-Lady Gremory?"
Issei's tone is more questioning than surprised this time, and Venelana realizes she's staring again, BEEN staring, this time for minutes, and this time for far too long for Issei not to notice her panting over his bone like a bitch in heat. Biting her lower lip, Venelana draws back and stands up. Issei's eyes follow her up, but if he's afraid she's going to back away and end this… he need not worry. She has no intention of doing so.
"Issei… you will continue to keep your hands off of me, understood? No touching allowed. You will show me how much of a gentleman you can be. What I will do will test your very limits… but I expect you to succeed, nonetheless."
He swallows again but nods his head with determination. That determination fades quickly when Venelana's next act is to hike up her dress, revealing not just her upper body but her gorgeous legs and her crotch as well. Climbing aboard Issei's lap is a challenge with his massive cock in the way, but Venelana manages nonetheless. And with one hand sliding aside her panties and the other holding his cockhead in place so that she can press her wet slit up against it, its not long before Venelana is sinking down the boy's shaft.
Issei groans, but admirably enough, he does not touch her. Even as Venelana wraps her arms around his neck for support, even as her bountiful, bouncing breasts settle right in front of his face, he continues to cling to the chair, all while his throbbing erection disappears up into her cunt, inch by inch. He's so big… bigger than any man she's ever had. Venelana can barely withstand it, and at the same time, she can barely keep herself from going faster further.
Instead, she settles for a middle ground, taking her time and teasing herself as much as she teases Issei, her insides gripping and squeezing down on more and more of his length. Letting out a shuddering breath, Venelana tries to keep herself under control. It's all the gorgeous MILF can do not to go further, all she can do not to… oh fuck that was her G-spot, wasn't it?
The Lady Gremory SHRIEKS as she tilts her head back and cums on the spot, Issei's cockhead reaching a part of her cunt that her husband never could before. A part of Venelana's cunt that had remained untouched all of her life, a part of her that she had NO idea would give her such pleasure. And as Venelana cums, her entire inner passage squeezes down on Issei's cock even harder, causing the boy to grunt and pant, his squirming as he tries to hold himself back growing all the more desperate.
Venelana ends it with a kiss. Her hands grasp either side of Issei's head and her tongue goes halfway down the boy's throat as she kisses him deeply and passionately, all while grinding herself further and further down his cock. When they pull apart for air a moment later, she continues to hold his head in her hands, her eyes wild and wide as they meet his.
"Forget what I said Issei. Touch me. Touch me however you like. Just so long as you FUCK me while you're doing it. Do you understand me, young man? FUCK ME, ISSEI HYOUDOU!"
The next thing she knows, Issei is standing up from his seat. But not before his hands come up off the chair at her words and grip her ass cheeks HARD. Venelana squeals as she's lifted into the air, and her strong legs wrap around Issei's waist, even as she continues to wrap her arms around his neck. Of course, the most important side effect of him standing up… is the progress of gravity. Half of the boy's cock (and really, she cannot keep calling him a boy after this) is STILL outside of Venelana. Not after he stands. Several more inches disappear into the Lady Gremory's cunt as she DROPS down his member, and the next thing she knows, her womb is playing hostess to a big, fat dick tip as Issei's cock spears her to her core.
Venelana throws her head back again and screams her enjoyment for all the world to hear. And then she begins to bounce with all her considerable might, riding Issei Hyoudou as he holds her buttocks in the palms of his hands, his fingers digging into her soft, pliable badonkadonk the entire way. He walks with her, and then Venelana finds herself landing hard on a desk. HER desk, given this is her study that she's been giving him lessons in these past few weeks.
Issei doesn't much care, but then, neither does Venelana by now. And as the young devil gives the hot MILF everything she never knew she needed, neither of them finds much room to care about anything other than pleasure in one another's arms. The Lady Gremory really should have kept in mind just how pent up Issei was, after everything he went through on a daily basis. Even if it took quite a bit to cause an erection now, that didn't mean the boy didn't have his frustrations to work out.
And work them out he would, thoroughly and for hours, much to Venelana Gremory's utmost and vocal delight.
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