Devil's Fiance (Highschool DxD) (Patreon)

Summary: Issei Hyoudou is introduced to the supernatural world in the most absurd way... by a proposal from Rias Gremory! A devil heiress! Too bad he quickly learns they can't consummate their new relationship just yet... But luckily for him... Rias has a plan to keep him busy until then.

AU: Alternate Universe where Riser is not betrothed and Rias gets to pick her own partner. Also assume Sirzechs and Zeoticus aren't in the picture.

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Chapter One: Servant of the Family

“Issei-sama...” A calm, soothing voice awoke him from slumber.

He opened his eyes, confused to hear the beautiful sound of a woman's voice rather than the high-pitched anime girl voice of his alarm clock at home.

He was startled by the strange feeling surrounding him, softness on all sides, with cool, smooth silk enveloping him. He was lying in a massive bed, built for a king, with crimson silk sheets.

His mouth fell open as he came face to face with a stunning beauty.

A maid. Uniform and all.

She woke him with a gentle touch on his shoulder. The black and white servant's outfit she wore was straight out of his lustful fantasies and dirty magazines. He was speechless, thinking to himself, 'Such an amazing outfit exists in real life?'

No, perhaps he was just trapped in a dream because the beauty in front of him was far too good-looking to be real.

Her luxurious black hair was modestly pulled back into a bun, and her gentle blue eyes and supple pink lips curled into a friendly, charming smile. The white apron of her maid's uniform stretched outward to display her impressive chest proudly. Her huge bosom tantalizing enough to provide him fap material for weeks without the need for his dirty mags.

Display how perfect she was, how kind and modest she appeared; there was some kind of magnetic, lewd aura around her. Like she was some creature of seduction, sent here to drive him mad with lust, it wasn't strange for him to wake with a raging case of morning wood, but the tent he was pitching today was almost painful.

'W-wait...' His mind raced as he leered at this servant girl's breasts. He didn't even know her name, but his mind was filled with dirty thoughts. How perfect and beautiful the rolling hills of her chest must look uncovered, or how those supple pink lips were perfect for wrapping around his cock.

He blushed and mustered the willpower to rip his eyes away from her mesmerizing chest. He gulped heavily, feeling about a half-second from attacking this kind-looking woman like some kind of beast. He may be a raging pervert, but his pride as a man was better than that. (Or so he liked to believe.)

'Wait, wait, wait..!' His mind sharpened for a moment, dragged from thoughts of sex by something far more important, 'T-t-this is..!' His eyes snapped around the room, taking in the luxurious splendor of a rich, palace-like bedroom. The expansive, four-poster bed that seemed built to fit a dozen people was just the start. There were bookshelves that stretched from floor to ceiling, a large decorated sitting area, and an impressive stone fireplace.

It was an excessive luxury for a bedroom, and CERTAINLY not a place where someone like him deserved to sleep.

'T-then..!' He grabbed his chest as his heart nearly exploded with startling excitement, 'L-last night really happened..!'

He remembered the most incredible, surreal experience of his life.

“So... Issei...”

A voice like an angel, flowing from sinful ruby-red lips.

Hair as red and gorgeous as a rose and a pair of sparkling, playful blue eyes.

“Will you marry me?”

Words that sounded so absurd he couldn't understand them at first. It was only after repeating the question twice that he managed to squeak out 'yes'.

Because the woman who'd asked it, was Rias Gremory.  She was more than his college's 'Great Beauty'. She was rich, incredibly beautiful, and brilliant beyond compare.

And he..? He was Issei Hyoudou... the hopeless lecher whose only redeeming quality was his determination (When something lewd was involved)

He couldn't fathom why she'd even stand in the same room with someone like him. But hadn't simply asked him out on a date, she'd PROPOSED! It was crazy. He wondered at the time if he was getting scammed or maybe even kidnapped.

'But then..!' As his mind followed the previous night's events, his eyes grew wide.

He never even got an explanation for her crazy sudden proposal because when he squeaked out his excited 'yes!' (thinking to himself that marrying this beauty was worth the risk of getting kidnapped) she revealed something even crazier. Dark leathery wings and black fire enveloped her hands.

She was a devil.

'Ah. It had to be something like that.' That was all he thought at the time. Somehow, the revelation that she was a supernatural evil creature was easier to accept than her desire to marry him. He simply nodded at her flaming hands and replied with a simple, “I see.”

Did that change his answer? She had asked.

“Not at all!” He proclaimed loudly. Even if she was a devil, her beauty was too much for a simple guy like him to resist. There was no way he could, with a chest as impressive as hers! Her expansive bosom seduced him.

He thought his inward thoughts were showing on his face (Like usual) but strangely, she smiled at his answer.

After that, they hadn't had much time to talk before he was escorted to his own room to 'sleep on it'. There was no way he could do that, right? Sleep? Not with his thoughts filled with this busty, beautiful devil. Strangely, he quickly fell drowsy after he finished his cup of tea. By the time his head hit the pillow, he was out.

Which lead to his current circumstance.

“Good morning, Issei-sama...”

“Oooh..!” He exclaimed without holding back. He eyed the beautiful, busty maid beside his bed, “S-sama..?” He stammered.

“Yes. Issei-sama.” She smiled radiantly at him, “Or would you prefer simply, 'Young master?'”

“Ooooh..! That's good too!” He said excitedly, feeling incredible as this gorgeous maid said those incredible words to him. Being called 'Young Master' by a genuine maid... this was heaven! No, these were devils... Was it hell? Bah, what did it matter? If hell was this good, then why would he care about heaven?

“Eh, I like them both too much to choose!”

She smiled knowingly, “Then today it will be Issei-sama.” He grinned broadly as she said it again, “Issei-sama… Rias-sama would like you to join her for breakfast to discuss the details of your betrothal.”

“Betrothal…” Issei felt his heartbeat with excitement. The words felt foreign on his lips, ‘Betrothal… I’m really gonna get married? And my future wife is our school’s #1 beauty?’ He was so happy he felt like crying.

He jumped out of bed and grabbed the clothes the servant prepared for him. He shamelessly shucked off his clothes right in front of the maid. Emboldened by his unreal circumstance, he didn’t feel shame, even tugging down his pants.

“Oh my…” The maid said softly, bringing her hand to her mouth.

He realized she was looking.

But then…

She smiled softly, and did not avert her eyes, “Rias-sama will be very happy indeed… fufufu…”

Issei’s confidence shot through the roof.

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Dressed in fine silk robes like an emperor, Issei entered the grand dining hall of Rias Gremory’s home. With everything that had happened so rapidly last night, he hadn’t had much time or thought to examine the place.

But it was incredible.

Rias’s home in the mortal world was extravagant. A full, walled-in estate you’d expect the daughter of a big-wig CEO to live in. A modern palace but with surprisingly old-styled architecture.

But once he’d agreed to the deal, the Devils used teleportation magic to take them to Rias’s REAL home. A genuine castle in the ‘Underworld’ that made her manor in the human world look like a humble vacation home in comparison.

It was so richly decorated that Issei would be gawking at the splendor and size of every room… if he wasn’t so fixated on the splendor and size of the servant girls’ breasts.

‘This IS heaven..!’ Issei thought to himself, trying not to drool, ‘Oppai heaven..!’

Rias’ servants numbered easily in the dozens if not hundreds, and so many of them were strikingly beautiful, incredible CHESTY maids. Their vast, wobbling bosoms stretched out their form-fitting maid uniforms so wondrously that it fueled his desire more than any ero-manga he’d read in his lifetime.

These uniforms weren’t lewd or skimpy. They showed very little skin at all. And yet, these sensual creatures seemed to lure him in with their incredible chests. He never imagined boobs could actually bounce like that in real life!

Once he finally made it into the dining hall, he found her there waiting for him. He swallowed the spit in his mouth nervously, heart pounding with excitement and nerves.

“Good morning, darling. I hope you slept well.”

!!!

Her words were like thunder in his ears. Silky and sweet as honey, they nearly moved him to tears. It was the most incredible thing he’d ever heard. A busty, red-haired beauty is calling HIM ‘darling.’

‘Ah…’ He paused for a second to let the feeling encompass him, ‘I see… This is true happiness… This is why I was born a man...’

His eyes met hers, and he opened his mouth, “Yes! It was the best… d-darling..?”

“Fufufu…” She smiled at him, resting her chin on her hand while her sparkling blue eyes looked at him playfully, “You don’t have to force it, Issei… we can let those kinds of things come naturally… Come sit down with me. You must be hungry. I assure you that my maids prepare the best meals in the underworld.”

“Y-yes..!” He quickly took a seat across from her and stared wide-eyed at the luxurious feast of food on the table. However, he hadn’t set his plate yet, finding it hard to focus on food with Rias Gremory across from him.

“U-um… Rias…?”

She smiled as if the simple act of him stating her name brought her some kind of satisfaction, “Yes, darling~?”

“S-so now that I’ve accepted...” He started slowly, “I’m just wondering what it means... to be marrying a devil...”

“Hmm?” A charming smirk curled up on her ruby lips as she saw right through him, “What? Did you think I took your soul or something?”

She giggled at him. It was a wonderful sound.

“Uh... Yes?” He scratched the back of his head, “That's what devils do when you make a deal with them, right?” It was a wild conclusion to jump to, but that was the only way he could end up marrying such a bombshell beauty, Issei thought to himself.

“Hmm...” Her sparkling blue eyes narrowed at him with a playful smirk on her lips, “And you agreed anyway? Fufufu... do you want to marry me that badly? How cute...”

He blushed red, not just from her words but the sheer charm of the woman in front of him. To him, who'd hardly spoken to a girl his age, this devilish temptress was hard to even look at. She was so beautiful he couldn't control himself around her.

“Well, that’s one stereotype that you don’t have to worry about. I didn’t take your soul.”

“Phew...” He clasped his chest.

He opened his mouth.

Here he was. Sitting across from Kuoh’s #1 beauty. The peerless, untouchable senpai, whose chest was said to be the biggest in the school’s history… A woman who had asked HIM to marry HER.

Forget about getting a girlfriend. They’d skipped so many steps already.

Yet, when his mind SHOULD be thinking about kissing, groping, and dirtier things behind closed doors in the bedroom… he kept asking himself one question.

“Why me? Why did you ask... me?” If she didn’t take his soul, then he really couldn’t understand why she would want someone like him.

“To breakfast?” She grinned, “Because I wanted to eat with you. I usually eat with my peerage, but today I felt like it should be just~ the~ two of us~” She winked flirtatiously.

“…”

“Sorry,” She stuck out her tongue cutely, “It was just a little joke~ Well, why you? There are a lot of reasons. First, I have to ask, why not you?”

“Huh?” He blinked dumbly.

She leaned forward, keeping an ever-present smile on her luscious crimson lips while looking deep into his eyes, “Do you think you’re not worth my attention?”

“Uh…” He swallowed, ‘Of course I’m not.’ It was hard to say that out loud.

“Remember who I am…” She said as she rose from her seat.

Issei gulped as he watched her heavy chest slightly bob in her white blouse. The slightest movement of her body made those incredible sweater puppies wobble mesmerizingly. He couldn’t imagine just how SOFT those amazing titties must be for her body to act like that.

She walked around the table’s edge until she was standing beside his chair. Then she looked into his eyes and softly brought a hand to his cheek, “I am a devil.” As she spoke, her leather wings extended from her back, “You’ll find our… norms… are a little different than that of humans… You may find it hard to believe Issei… but you are exactly my type…”

“W-wha..?” He gasped, eyes popping open in shock, “B-but I’m… I’m a pervert..!” He exclaimed in surprise.

“Yes. I know.” She smiled at him.

He couldn’t believe his ears. Was she really implying what he thought she was?! There was no way. Female perverts didn’t exist!

Unless?!

His eyes grew huge as he considered the implications. If she was a devil, then maybe it was possible she WAS a pervert! His heart thumped with excitement.

“That is only one of the reasons, however,” She said. Before he could glean what she meant by that, she continued, “There are many more. Most important to my family, that is, is the presence of your sacred gear.”

“S-sacred gear?” He repeated in confusion.

“Yes, an incredibly powerful one. One that will soon have you ruling the Underworld as a Great Satan.”

“Rule..?”

She smiled mysteriously, “Yes... That is what our prophets claim. Among our kind are magic users who can glean information from the future. You will do great things, Issei...”

“...” He was speechless. Just yesterday, he was a total loner who peeped on girls changing and dreamt of having a harem. Now he was getting married to a busty devil and told he would rule the underworld?

That was absurd.

But if it was true, at least there would be some reason this busty girl would want to marry him. If he did rule, then she would have power, too, as his wife, right? That made sense.

Thinking along those lines, it was easier to accept. She was using him, right?

Then... in that case... wouldn’t it be fair that HE use HER as well? He thought while leering at her breasts.

“I see...” He said slowly, “Then you’re alright with marrying a pervert?”

“Yes.” She said with a little laugh.

“M-my goal is to have a harem, you know?” He proclaimed boldly as if he was suddenly challenging her to reject him now, “Even if you’re going to be my wife, I won’t give it up! I’ll still try to have sex with as many girls as possible!”

“…”

A moment of silence passed, and Issei’s face flushed red. He was suddenly very aware of the dozens of gazes drilling into his back. The incredibly beautiful female maids were still here with them, waiting on Rias’s beck and call.

But as a man, he couldn’t back down. He stiffened his face and met Rias’s gaze without blinking!

“Good.” She smiled.

“Wha?” He said dumbly.

She grinned devilishly and cupped his cheeks. He blushed. Not because of the contract, but because of the look on her face! Her eyes were glassy and half-lidded, her mouth softly parted as a hot breath escaped her glistening crimson lips. She softly bit her lower lip, “That’s… perfect… I could have nothing less… from my darling~”

“Y-you… you’re cool with that..?” He said numbly.

“Of course I am. Lust is a wonderful sin to have as a Devil… and you’re quite Greedy too… my perfect match.” She smiled delightfully, “So you want a bunch of women, hmm? Go on then, darling. But pick carefully. I want only the best for you.”

His nostrils flared as he began to realize what kind of creature he’d just taken as his future wife. His mouth opened without thinking, “A-and that includes you right? You’ll be my w-wife..? S-so you’ll join me in the bedroom, right?”

She smiled salaciously, “Of course. I’ll be the first to warm your bed~ each and every night~ No matter how vast your harem grows.”

Issei felt his body heat up. The rising feeling in his groin was getting harder and harder to ignore. He shifted uncomfortably in his chair with a dirty smile on his face.

“Oh?” Her voice lowered into a sensual purr, “Does that please you darling~?”

Suddenly, her voice took on a seductive, teasing tone as she leaned in close. Issei nearly groaned as her delicious scent drew in close, her massive chest so close he could practically feel her body heat. Then she reached down and suddenly grabbed his crotch.

“Ah!” Issei made a noise of surprise as her delicate fingers started feeling the bulging stiffness of his half-erect cock through his pants.

“Oh my...” Rias’s blue eyes looked down as an utterly pleased look appeared on her face. She grinned as she licked her lips, “What a pleasant surprise...” She muttered to herself as she fondled him.

“Oh..!” He groaned and shifted in his seat, “R-rias..!”

She giggled in his ear, “Look how hard you are already, darling... Are you looking forward to that already? Doing naughty things with me in our bedroom?”

With words like honey in his ear, Issei let out an embarrassing moan. His cock throbbed painfully hard in his pants, bigger, thicker, and harder than he’d ever been in his life. Surrounded by these sensual creatures, he felt like he was losing control of himself.

Rias whispered in his ear, “Is that what you desire, Issei... My body? Do you want to see it? To abscond with me to my bedroom and tear these clothes off of me?”

His heart was pounding so hard he could hear it in his ears. His face was red and his fingers twitched as he resisted the urge to grab her.

She giggled like a devil in his ear, “Do you want to look?” She said teasingly, “At my big, naked titties~? I’m quite proud of their shape, you know... and they feel so good to squeeze...”

“Haaah...” He was breathing like a rabid dog, under the thumb of this temptress.

“Or maybe...” She trailed her fingers across his twitching bulge, “Maybe you want me down on my knees... looking up at you while I give this big... meaty... COCK of yours the attention it deserves... Would you like that Issei, feeling my soft lips wrapped around your big dick?”

“Oh god..!” Issei felt about to explode.

“Ngh!”

“Wah..?” Issei whined with confusion as Rias pulled away, a flash of discomfort on her face. That erotic, lustful look she wore disappeared in an instant as she placed a hand on her soft chest.

“Ahem... Sorry, Issei.” She smiled cutely, winking at him, “I got a little carried away with my teasing. For the record, try not to say the ‘G’ word around us Devils. It’s quite unpleasant.”

“H-huh.?” He blinked dumbly, trying to remember what ‘G’ word he’d said, “Oh!”

“Sorry.” He said quickly, dismissing it as he rose from his seat, “D-did you mean that..? I mean..? C-can we really?”

She giggled at him, eyes glancing down to his stiff, bulging crotch, “You really are excited~! I’m flattered I have such an effect on you, darling... But I apologize. I was only teasing.”

Issei wore a face like a kicked puppy.

Rias smirked at him, “I’m sorry, darling. That was mean of me... but please understand, it’s not that I don’t want to have sex with you... but we Devils have strict traditions in the noble families of the ‘72 Pillars’ of which I am an heiress.”

Issei’s face was troubled, still hot-blooded from the sudden, erotic teasing moments before while he tried to understand what she was saying.

“One of which...” She wore an annoyed face, “Is that I must remain pure.”

His face shattered with devastation, “What?!” He nearly screamed.

“Not forever!” She said quickly, “But until we are married! Our wedding shall take place on the winter solstice... and my purity shall be given willingly, in the ceremony’s ritual... It’s important for the magic of our household...” She explained.

Issei was surprised that she too, seemed utterly disappointed by this. He was figuring out that Devil girls like her seemed a lot more lewd than girls he knew.

He put on a stiff face, “Oh... I see... So we’ll have to wait like...”

“Four months,” Rias said, delivering an.other punch to his gut.

Issei lamented. How was he supposed to spend his time knowing that he’d be married to this gorgeous, erotic woman... but not able to touch her?! That kind of torture would drive any man mad!

“Don’t worry.” She suddenly said

“Huh?”

“I must remain pure.” As a slow, sensual smirk curled on her ruby lips, she said, “But that doesn’t mean you do.”

“W-wha-?!”

“Fufufu...” She grinned devilishly, “Don’t worry, darling~! I’ll take very good care of you in the meantime..!”

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The rest of the day Issei was red in the face. Rias seemed to adore teasing him, and they spent the afternoon ‘getting to know each other better’. She explained some of the crazy things about the Underworld’s Society, like Peerages and Evil Pieces.

Later in the day, Issei found himself back in his own bedroom. A place for him to stay until he married his new Fiancee. The woman of which, was standing at the door with a big smile on her face.

As always, Issei was impressed by Rias’ body. He was drooling as he stared at her loose, sheer nightgown. The fabric was incredible, so thin and whispy that it appeared she wore nothing at all, and he got a good look at her soft, pearly skin. Her massive chest was squeezed snugly into a tight black bra, her bulging cleavage nearly bursting out of the top. Her meaty hips were sinfully decorated by thin, lacey panties and an erotic garter belt.

Issei was excited to learn that this was Rias’s usual nighttime appearance. Her ‘comfy clothes’ that she wore around the privacy of her family home, where only female servants would see her.

So it was the sight that his eyes would be feasting on every night from now on. An incredibly busty beauty in snug, sexy lingerie.

But Rias, even dressed like that, was only Issei’s center of focus for a second, as a second woman followed in behind her.

“Darling~ This is Grayfia. She’s my head maid, and most trusted servant here.”

The woman beside her should’ve appeared like an angel compared to Rias with how modest her maid uniform was. Yet somehow, she also had an incredible sexual allure that drove Issei wild.

She was a sexy young woman, with striking silver hair lightly braided in a single strand on each side of her face. Her perfect, porcelian skin exemplified the extrodinary beauty of this woman, while her ruby red eyes glittered like jewels. Her light peach lips humbly smiled at him as she met his lecherous gaze.

He gulped heavily, eyes sinking down to bask in the glory of her expansive chest. Her massive breasts were even larger than Rias’, boasting the size and wonderous shape of a sexy, full-blown woman. A MILF in every sense of the word. No matter how humble her uniform was, covering every inch of her skin, her buxom hourglass was too much to hide.

‘Oh my...’ Issei bit his tongue, eyeing Grayfia with unrestrained lust, ‘Her tits are even bigger than Rias’!’

She bowed at him, lightly lifting her skirt in a slight curtsey, “Good evening... Young Master.” As she dipped her head, the stretched material covering her chest wobbled with the movement of her bosom. Issei’s eyes couldn’t look away.

‘Ooohh..!’ Issei was shaking with excitement, ‘This busty MILF is going to be calling me master..! How did I get so lucky!?’

Grayfia’s red eyes met him as she smiled politely, “Grayfia Lucifuge at your service, Young Master. I will be tending to your every need here in the Gremory Estate.”

She said it plainly, but Issei couldn’t help but gulp. The words ‘Every need’ hung in his dirty mind. When said by such a sensual, erotic creature, he couldn’t help but think dirty things.

“Y-yes...” He said, licking his lips as he leered at her heavy breasts.

“Fufufu... I think he gets it already.” Rias said, looking at the way Issei was drooling over Grayfia’s tits.

He snapped his gaze up to her with a simple, “Huh?”

Rias grinned devilishly, “Grayfia has been my servant since I was born. I could you could say she’s something of an older sister of mine...”

Inwardly Issei grimanced. The words ‘Older sister’ translated as ‘Off limits’ when coming from his future wife. He strugged to keep the disappointment off his face, while fighting back the dark thoughts telling him to go behind Rias’ back anyway.

Grayfia was too erotic to resist.

Rias saw right through him, “She’s the best at servicing my needs, especially at night~ Fufufu~💓”

Like the horny young male he was, his mind only went to one place. He imagined Grayfia on her knees between Rias’s spread legs. He imagined their incredibly huge tits squeezed together as their naked bodies intertwined in passion.

While he was lost in his lewd fantasy, both ladies looked down at his crotch, watching the way his stiff shaft bulged out down his leg.

“...” Grayfia kept an unreadable expression.

“Fufufu...” Rias licked her lips, eyes twinkling with desire.

Issei shifted uncomfortably under their gazes, shifting awkwardly to adjust the pain in his pants without grabbing his junk right there in front of Grayfia. He silently cursed. Rias had explained that EVERYTHING was off-limits. Not just her virginity. She couldn’t even touch him down there with her hands or mouth or tits. There would be no sexual contact between them whatsoever. He cursed whatever magic made this evil rule. He would be suffering blue balls for months until their wedding day.

Unless...

He didn’t know it, but his and Rias’ line of thinking was in perfect sync.

“That’s why...” Rias brought him back to the conversation, “I can trust her to look after you. Grayfia takes her duties VERY seriously and will do everything I command of her. Right, Grayfia?”

The silver MILF bowed her head with a simple smile, “Of course, Rias-sama...”

Issei looked between them as something he didn’t catch passed between the two. Rias was grinning, eyes flicking between Grayfia and him. Then she sauntered up beside him, drawing her plush, half-naked curves into his side.

He gulped as Rias’s softness and warmth pressed against him, and she once again whispered her sultry voice into his ear. Her hand slipped down to his groin, teasing the stiff bulge of his cock with slender circling fingers, “You can feel it, can’t you, Issei..?”

“H-huh..?”

“What it’s like... being in the presence of us Devils...” Her voice was an erotic purr that flamed the lust growing inside him. His cock was painfully hard, “We’re creatures of sin, you know. It’s not easy for a man to resist us... especially a mortal. Be honest, darling, are you feeling excited? Does being around us, beautiful Devils, make you... horny?”

He gulped again, feeling his entire body tremble. He wanted to grab her hand and force her to touch his cock, aching for any stimulation. He gasped, “Yes..! You ladies are way too hot! You’re driving me crazy...”

“Fufufu... Don’t worry, dear, I understand💓” Rias purred in his ear. The pale, supple mountains of her chest squeezed his arm in their soft embrace, “You’d have to be dead not to desire us... You’d be shocked at what humans would do for just a second of our attention... and that’s just your human side...”

“W-what?”

“I know a little secret 💓” She continued, her sweet breath tickling his ear, “Our prophets know more than just what you’ll become... they’ve figured out the nature of your powers...”

“M-my powers..?” Issei said numbly, seduced into a haze by the seductress at his side.

“Mhm...” She giggled, raising a hand to trail a fleeting touch on his cheek, “Your power... is draconic in nature. Can’t you feel it, Issei... that rampant, burning desire in your core? Something more than just lust... an urge to follow your instincts...”

As Rias’s words dripped like honey into his ear, Issei felt his burning lust boiling over inside of him. It was everything he could do to resist grabbing her fat, half-naked ass and stealing her plush, ruby lips in a kiss. Instead, his fingers twitched as they grabbed her waist and pulled her plush chest deeper against himself.

“That’s it...” She giggled again, her bright blue eyes watching him with undeniable desire, “A powerful... domineering urge... natural instincts telling you to grab us females and make us submit to you.”

He could hear the blood pumping in his ears as he let out a haggard breath. Looking down into her deep, seductive eyes, her glistening red lips, and the deep, expansive valley of her cleavage, he was ready to give her what she desired. Something roared inside him to take this woman as his mate.

He forgot all about their promise, Rias’ purity, the wedding, the magic, everything. The only thing on his mind... was the pair of mates in front of him.

“That’s it...” Rias’ eyes sparkled with delight, looking up at his own slitted draconic pupils, “That’s who you are, Issei... The Red Dragon Emperor...”

He didn’t even hear her. Fueled by primal desire, he lost control of himself. He grabbed her.

...but she slipped out of his grasp. He growled with frustration as he swiped at empty air, then raised his eyes.

Rias was smiling at him, standing behind Grayfia, her hands on her shoulders, “That burning desire of yours... it’s too much to resist, isn’t it?” She said light-heartedly, “And as your wife, I would be cruel to deny you... satisfaction. But don’t worry, my love, I will always take care of you.”

As his senses came back to him, he was silently digesting Rias’ words. There could only be one meaning, right? With her so blatantly shoving Grayfia in front of him.

“D-do you mean..?”

“That you can fuck Grayfia?”

His heart skipped a beat as she said it so crassly.

Rias grinned devilishly, “Would you like that, my husband? Would you like to fuck my busty maid? To squeeze these big, fat tits of hers?” She said lewdly, as she reached behind Grayfia and grabbed the huge globes of Grayfia’s breasts in her hands. The sheer amount of tittyflesh swallowed up her fingers as she squeezed her fingers in and jiggled those glorious breasts in her hands, “Fufufu... they’re bigger than mine💞! Aren’t they just incredible, Issei? They’ve never been touched by a man, you know?”

He huffed with lust, watching Grayfia’s legendary breasts squeezed and groped by Rias like a pervert.

The maid herself did not even blush. She merely closed her eyes and let Rias grope her as she pleased.

Rias’ eyes gleamed as she looked at him, “This time... I’m not teasing💞~!”

“!!” Issei gulped loudly.

“I’ll give her you, my darling~!” Rias giggled at the lewd look on his face, “If you want to fuck her, go ahead! She’ll be your servant from now on, and she’ll follow your every command!”

“R-really..?!” Issei swallowed thickly, looking at Grayfia with undisguised lust. His dick felt like it would explode in his pants. Already his hands were raised up, ready to grab and squeeze those incredible tits himself.

“Heheh, of course~! Anything for you, my love~!” Rias said as she dropped Grayfia’s tits and smiled like a cat, “There’s just one little condition.”

“H-huh? What is it?” Issei said quickly, snapping his gaze to her. He was ready to do anything, even give up his soul to this devilish bride.

Rias licked her lips, her blue eyes glossy with a lewd look, “Only while I’m watching~!”

She said the most outlandish thing.

Issei swallowed the spit in his mouth. He’d have to fuck her maid while she watches? His own future bride, watching him fuck another woman? Did that put him off? Not a chance! If anything, that made him so much more excited.

“Deal!” He said loudly.

“Fufufu... he looks so excited, doesn’t he Grayfia?”

“Yes, my lady.” Grayfia replied succinctly.

“A-are you really okay with this?” Issei asked Grayfia with a shaky voice, “I-I mean, I get that Rias is your master... b-but that doesn’t mean you have to...” He swallowed, “...with me.”

Grayfia wore a kind smile, her gleaming red eyes looking directly at him, “Do not worry. We Devils have a different way of thinking than humans, Young Master. I have devoted my entire being to the Gremory House. If my lady wishes me to join her husband in bed, then I will gladly serve you in any way you wish.”

“S-seriously?!” He couldn’t believe his ears. To think women like this really existed! Was this the difference between humans and devils? If so... did that mean the other servants would think the same? He drooled, imagining himself surrounded by busty maids who would lift their skirts to show their soft butts and naked pussies any time he desired. His own harem of servant girls.

His dick roared at him to stop talking and just go for it..!

But as a man and a human, there was a little underlying doubt in his head. He felt like he was doing something he shouldn’t.

Even as he was thinking that, he reached his hands forward.

Grayfia softly smiled and brushed back her hair, then she proudly stuck out her chest, offering the two massive melons of her breasts to his eager hands.

He reached forward and sank his fingers into the soft flesh of her boobs.

“S-so soft..!” He breathlessly exclaimed with a voice full of awe as his fingers dug deeply into the warm softness of Grayfia’s utterly huge boobies. He was excited, finally getting his hands on a pair of real breasts. And it was the breasts of a voluptuous devil, far bigger and softer than anything he’d find on a human woman. It was incredible.

“Mmm... are Grayfia’s titties as good as you expected, Issei?”

He froze at the sound of Rias’ voice. For a second, a cold feeling surged through him, feeling like he’d just been caught in a trap. Maybe this was a test to see if he’d be faithful, and he’d just utterly failed. But as he thought that he looked up into her eyes and those doubts were washed away.

She wore the expression of a horny woman, biting her lip lustfully with a grin on her face, “They’re soft, aren’t they..? I bet they feel even better... without her pesky uniform in the way 💕”

With his bride’s permission and his hands on a full set of womanly breasts, Issei felt incredible. Any shame or hesitance he had as a virgin was blown away by pure excitement. He grabbed her boobs firmly, squeezing as much of her plump titties as he could fit in his mitts.

“Mn...” Grayfia kept a neutral face as he groped her chest but let out a soft, womanly noise.

He quickly wanted more. With Rias’ spurring him on, he wanted to see Grayfia’s naked boobs. He fumbled with the buttons on her blouse, failing to open them with shaky fingers.

Grayfia grabbed his hands, “Young Master... allow me.”

He froze at the sound of her soothing voice as she gently pulled his hands away from her chest. Rias grabbed him by the arm and pulled him back to the bed. He sat back, giddy with excitement, as he watched Grayfia bring her own hands to her chest.

There was nothing particularly sexy about the way she undressed. She was a humble servant, obeying her master’s desire, and yet somehow, this woman made this mundane act look like the most erotic thing Issei had ever seen.

She closed her eyes and kept a neutral face as she unbuttoned the blouse of her uniform one button at a time. The tension in her tightly stretched blouse gave way as each button popped free, revealing more and more of her creamy, delectable cleavage.

Until finally...

Boing~!

Issei’s eyes were treated to a wonderful sight. Grayfia’s massive breasts bounced free of their tight constraints as her shirt was pulled open, the soft globes of feminine flesh bouncing dramatically on her chest.

‘What kind of magic is that..?!’ Issei stared unblinkingly, mouth open in startling amazement. He’d groped that chest with his own hands, so there was no way he could be mistaken. He’d felt no bra beneath the soft fabric of her uniform. That was why he was so fixated on groping her boobs.

And yet... as her shirt spilled open, he was looking at a rich blue lace bra, impressive and large to contain her expansive chest... but rather than stiff and rigid, like he’d expected, this bra clung to her boobs like a second skin, and let them bounce and jiggle as if they were free, while keeping them propped up and proudly displaying her deep cleavage.

“A-amazing..!” He said dumbly, mesmerized by her boobs.

“Aren’t they..?” Rias giggled into his ear. Then her voice turned pouty, “But Issei... You haven’t said anything about mine..? They might be a little smaller than Grayfia’s... but my titties are nice too, aren’t they~?”

Issei gulped as Rias crossed her arms under her bra and pushed up her explosive titties to jiggle them in his face.

He groaned as his cock throbbed painfully in his pants and nodded quickly, “T-they’re amazing..! I want to squeeze them so bad..!”

“Heheh~ thanks darling~ You’ll have to wait to get your hands on my boobies, but don’t worry... Once we’re married, you can play with them anytime you like~!”

Issei swallowed thickly as his eyes were brought back to Grayfia. The maid had her hands behind her back, and Issei forgot to breathe for a moment, anticipating what would come next.

Snap~

In his lust-driven hyper-aware state, Issei heard the clasp of her bra as it popped free and the maid smoothly grabbed the cups of her bra and pulled them up. There was a moment of glorious tension as her massive boobs were pulled up, and then dropped.

Her naked breasts bounced free on her chest, giving him the most glorious titty-drop in the world. A pair of perfect snowy mountains, capped on their mighty peaks by a pair of bubblegum areola and tender-looking nipples.

The rest of the uniform fell off her quickly after, falling from her curvaceous hips to reveal the deep blue exotic lace of her panties and garter belt, as well as a pair of dark stockings that accentuated her long legs and thick, soft thighs.

‘What a woman..!’ Issei thought in his lust, blown away by just how voluptuous and sexy this woman was. Despite the plumpness in her womanly features, her skin was flawless without imperfection. Silky smooth and glowing in the dim firelight of the bedroom. She looked like a goddess... or perhaps a succubus.

Grayfia’s red eyes slowly opened as she tossed her bra aside and stepped out of the uniform, pooling at her feet. Without a moment’s pause, she hooked her fingers into the band of her panties and-!

“Hold on, Grayfia.”

She paused at Rias’ voice.

“Fufufu...” Rias lightly laughed, “Let’s leave those for now. I think Issei should be the one to take those off!”

“As you wish.” Grayfia nodded once.

“Now... let’s have some fun~!” Rias said as she slipped away from Issei on the bed and sauntered over to Grayfia.

Issei was treated to the glorious moon of Rias’ pale white booty, thick and bouncy in its perfect shape. Her thin black panties were nearly swallowed up by the thickness of her wide, firm ass, and the sight was good enough to tear his eyes away from Grayfia’s naked boobs.

For a moment, he was silent, struggling to look at Rias’ ass and Grayfia’s tits at the same time. The two women dressed in sensual lingerie were driving him wild. He reached down to adjust his stiff cock in his pants.

“I might not be able to play with you myself, but I’m going to be a part of this at least..!” Rias proclaimed as she walked up to Grayfia, then she whispered in the older woman’s ear.

Grayfia closed her eyes as she quietly listened to her master’s command, then nodded, “Very well...”

Issei gulped deeply as Grayfia’s red eyes locked onto his, and she slowly walked over to him.

“Excuse me.” She said politely as she climbed onto the bed... directly over him, straddling his lap on her knees.

“Mpphgh!?” Issei’s face was shoved into the warm softness of Grayfia’s chest, smothered by the abundant tittyflesh of her cleavage.

“Heheheh~” Rias giggled playfully, “I knew you are obssessed with big titties Issei, so take your time and enjoy Grayfia’s as much as you want...”

Issei closed his eyes and took great satisfaction, rubbing his face into the heavenly cleavage of this bodacious babe. Her soft boobs were expansive enough to smother his face entirely. He was enveloped in her warm softness and sweet, womanly scent.

“Mmmgh..!” He gleefully rubbed his face into her tits while Grayfia silently held his head in her embrace.

“Heheh..!” He heard Rias giggle again as she grabbed his wrists, then his hands were suddenly forced onto the round globes of Grayfia’s ass.

He didn’t need much prompting after that and happily mauled the firm, perfectly shaped asscheeks of the silver-haired MILF in his lap. With his hands groping as much of the squishy fat of her perfect ass, his face smothered in her expansive bosom, and her arms wrapped around his head, he was completely overwhelmed by her womanly shape.

“Mmm...” Rias hummed to the side, watching it with a strange look on her face. She softly chewed her lower lip.

Issei kissed and sucked at the supple skin of Grayfia’s boobs, eagerly toying with them as he pleased. He wanted to squeeze them in his hands, bounce them in his palms, and jiggle them all over his face, but at the same time, he couldn’t possibly tear his hands away from the unbelievable softness of her meaty ass. Wishing he could do both at the same time, he attacked her body with fervor.

“Grayfia..!” Rias called out.

“Yes, my lady...” She said simply in response.

“Bwueh..?” Issei blinked, confused as his face was gently wrenched from her breasts. He didn’t have time to complain as Grayfia’s soft fingers stroked his cheeks and forced him to look up at her.

“Wha..?” He said with confusion, mouth falling open.

Then Grayfia opened her own mouth and leaned down.

“Mmmph?!” Issei’s eyes bulged. It happened so fast that he didn’t even know what was happening. He just suddenly felt her warm, wet tongue coiling with his in a hot, erotic tongue kiss. He moaned into her mouth as she pressed her hot, half-naked body against his and passionately swirled her tongue in his mouth.

“Heheheheh!” Rias grinned beside them on the bed. She touched her own wet lips as she watched them make out, “I would have liked to take your First Kiss myself..! But this is good too 💗! Heheh, Grayfia will give you plenty of experience for our wedding day and then~ 💕!”

Issei couldn’t even hear her, overwhelmed by the shockingly passionate tongue kiss he was receiving. Whatever command Rias had asked of her, Grayfia was giving it her all! She softly moaned into his mouth, sliding her fingers through his hair while pressing her naked bust into his chest. She began to slowly rock her hips, grinding her panty mound onto the thick, throbbing bulge of his cock.

When he felt the warm heat of her pussy pressing against him, Issei slowly lost himself again. Finally tasting the tongue of a woman, holding her half-naked body in his arms, and feeling her grinding her sex on his lap like a horny girlfriend... it was just about enough to wake the beast inside him.

His fingers squeezed roughly on her plump derriere. His muscles pumped with newfound strength, and it was just one moment away from throwing her down on her back and laying claim to her once and for all.

But before he did-

“Grayfia...” The lady’s voice called to her servant.

“Mwuah..!” Grayfia broke off the hot, tongue kiss, with a panting breath and glassy eyes. Then she swallowed and wiped her mouth, regaining the neutral expression of a servant, “Yes, Rias-sama..?”

Rias grinned and grabbed her own plump tits, squeezing them together as she winked at Grayfia.

The older woman bowed her head.

Issei groaned with frustration as she climbed off his lap. He squeezed her ass hard, trying to keep her from getting away, but this woman was unbelievably strong. She broke his grip without even blinking.

He opened his mouth to complain, but all that came out was, “Aaah..!” As he felt a delicate hand on his trousers.

He looked down just in time to see Grayfia unbutton his pants. He groaned at the sight. The busty maid, with her naked tits still flashing his eyes, was kneeling in perfect posture between his legs. She masterfully undid his pants and in just a matter of seconds, released the tension he was feeling.

“..!” She said nothing, but when his fat cock sprung out to greet her, standing tall in all its thick, veiny glory, her eyebrows slightly raised. It was the most expressive he’d seen her yet.

“Oh... my...” Rias stared in wonder, licking her lips eagerly, “Issei...” She suddenly broke into a wide, pleased grin, “You beast..! Mmm... If word got around the school that you were hiding this... heheh, you’d have your pick of the girls...”

Issei’s cock visibly twitched as he heard Rias’ words. But he didn’t lament over such a lost opportunity, because he had two sexy bombshells, that couldn’t be compared to humans, half naked in his bed.

Grayfia slowly took it into her grasp. Her slender fingers looked so small when failing to wrap around the thick girth of this monstrous cock. She stared at it intently, and then her red eyes looked up to meet his. She softly smiled, “It is very impressive... it seems my maid did not embellish your size.”

He remembered the girl who had watched him change and grinned confidently. Now, with three different ladies commenting on his size, he got a big head.

Her white silk glove slowly glided up and down his cock, giving it a few testing pumps. The thick meat throbbed dangerously in her grasp as the tip flared and drooled a line of sticky pre.

“Hmm...” Grayfia stared at it intently. She lightly touched the strand of pre, letting it stick to her gloved finger as she pulled away. Her eyes looked down to examine his heavy hanging balls, each big enough to fill up her palm entirely. They appeared to be thrumming with desire, churning as they prepared their thick payload.

“Indeed...” Grayfia said at last.

“Huh?”

Grayfia looked at him with a blank expression, “You are dangerous indeed... If left unchecked, who knows how many of our serving girls would fall victim to such a beast... And Rias-sama is at the greatest risk...”

“W-what?!” Issei’s mouth fell open, “B-beast..? I-I’m no beast..! I-I wouldn’t attack anyone... even if they were sexy maids!”

Grayfia looked up at him, slightly raising one perfect eyebrow. She kept a straight face even as she wrapped her white-gloved fingers around his throbbing cock and gave it a few slow, deliberate pumps, “Perhaps not right now... but after weeks of living surrounded by us devils?”

He gulped. Just one day, he was fighting off the urge to grab and fuck Rias every time she teased him. Could he really resist that for months until the wedding day?

“Fufufu... I told you so~!” Rias just grinned, “Now it’s your responsibility Grayfia... drain my darlings balls dry 💞!”

“As you command.” The servant said in response. She looked up at Issei one more time, “I will take good care of you Fiance...”

Issei watched Grayfia raise one white silk glove to her lips and bite the finger to pull her hand free. Then the other, and with her bare hands, she began softly stroking the length of his thick, turgid cock.

“Ooh..!” Issei groaned and balled his fists in the silk sheets of his bed. He had to stop himself from bucking his hips into her hands.  Just the little touch of her soft hands was a million times better stimulation than anything he’d felt before.

“T-that’s it..!” He gasped.

“Does that feel good?” Rias purred in his ear, “My servant’s hands stroking your cock?”

“Y-yes..!”

“Heheh~ I’m glad. Don’t be shy, Issei... Tell her what you feel..!”

“F-faster..!” He said quickly, “Stroke me faster, Grayfia..!”

“As you command.” She said politely as she began pumping the thick length of his cock with faster strokes. Her slender fingers struggled to wrap around the massive thing as she double-fisted his imposing size.

She looked up at him with those smoldering ruby eyes, “Is this to your liking, Young Master?”

“Y-yes..!” Issei groaned loudly. His cock felt bigger and stiffer than he’d ever been in his life. But the feeling of Grayfia’s hands jerking him was so much better than he was expecting. He felt like cumming almost instantly but desperately resisted the urge. He didn’t want this to end this soon.

And, as a man, he had a stubborn pride. He didn’t want to cum quickly in the presence of these beauties. It was that insecurity that made it easy to resist that urge building in his balls.

Rias watched him gasping with pleasure under Grayfia’s gentle, coaxing handjob. She, herself, was feeling hot and excited, squeezing her plush thighs together as she watched the two of them. She was a greedy, selfish girl who always got what she wanted. That was why she was surprised to feel such excitement, giving her man to another woman before she’d even so much as kissed him herself.

But she didn’t deny this newfound side of herself. She was a devil afterall, discovering a kink like this was an exhilirating experience. She was having just as much fun as Issei was here.

“Heheh~ that’s it!” Rias cheered them on, “Pump that huge dick, Grayfia... You two look so hot right now~!”

The fact that it was Grayfia, the same stoic, dependable maid that had been by her side since she was born, made it all the more exciting. She was eager to see the ‘Strongest Queen’ stripped bare and at the mercy of her new Fiance, the man who would become the ‘Red Dragon Emperor’.

Grayfia kept working at the full, throbbing length of his cock, spitting on her hands to lube up his shaft while she picked up the pace. She kept a straight face, even with his dick in her hands, appearing every bit the humble maid performing her duties.

To Issei, that was even more erotic. To have a picture-perfect maid kneeling between his legs, stroking his cock with her naked tits bouncing on her chest... it was unreal. A scene better than the best ero-manga. This woman was too sexy.

“Grayfia...” Rias called out beside them, her eyes playful, “Your arms must be getting tired from working that huge dick..! Why don’t you move on to the next step..?”

Grayfia looked at her master, who was once again cupping her breasts and winking. Then she bowed her head, “Very well...”

“Ooooh!” Issei groaned with excitement as suddenly Grayfia grabbed her massive MILF titties and trapped the huge meaty pole of his dick in the warm softness of her boobs. His cock twitched with delight as it was smothered in the doughy softness of the biggest chest he’d ever seen.

“Oooh..! Paizuri..! A real titty-fuck..!” Issei exclaimed. Feeling his rock-hard cock squeezed by the incredible pressure of Grayfia’s massive boobs while the beautiful MILF looked up at him with her enchanting red eyes and started bouncing her fat tits on his lap... It was everything he’d ever wanted in life.

Her chest was so much softer than he could’ve ever imagined, smoothly sliding up and down his cock as Grayfia expertly bounced her plump, expansive boobs on his lap and massaged his cock in her cavernous cleavage.

“Aaah..!” Grayfia made a soft noise as she leaned her head down and then.

Lick~!

Issei nearly exploded, feeling a hot, slender tongue slide up the bottom of his shaft. Despite how massive Grayfia’s chest really was, Issei’s cock was tall and proud enough to jut up from the sea of her cleavage. Grayfia, the most dutiful servant, did not let his cockhead go unattended and began servicing him with her mouth.

Grayfia’s wet tongue rolled around his purple cockhead, slurping up the sticky mess of leaking precum that had long since slathered it. She let out a soft moan as his taste lingered in her mouth and leaned down to suck the cockhead between her plush lips.

“Mmmph..! Slllrrrrrp~!” Grayfia sucked loudly on his cock, doing her best to dutifully tease every part of his cocktip she could reach while massaging her soft, fat tits around his shaft.

“Oooh..! Shit..! That feels amazing Grayfia..! Yes! Keep doing that..!” He exclaimed, biting his tongue several times to avoid cursing.

“Oh my...” Rias breathed hotly, watching with a rosy blush on her face as Grayfia closed her eyes and devoted all her attention to giving Issei a wet, messy blowjob while stroking his impressive shaft with her tits. She pressed her hand over her closed thighs, trying to resist the urge to play with herself.

She leaned softly into Issei, pressing her lingerie-decorated tits into his side, “Does it feel good?” She breathed hotly in his ear, teasing him with a light touch on his chest, “She looks so lewd, doesn’t she? It seems like Grayfia really likes your cock, Issei💕~!”

“Sslrrrrp~!” If Grayfia heard her, she didn’t let it distract her from the important duty of milking Issei’s cock with her tightly packed tits. She slobbered on the top noisily as she dragged her tits up and down again and again, until the heavy shelf of her tits were slapping noisly on the bare skin of his thighs.

“Y-yes..! It feels incredible!” Issei exclaimed, panting roughly, “I can’t hold it anymore. I’m gonna cum..!”

Rias grinned, “Good..! That’s why we’re here, Issei..! Go ahead and cum... I want to see you blast your sticky load all over Grayfia’s face 💞~! Cover her in that thick spunk and paint those huge tits of hers white💕!”

“Oh damn..!” Issei grunted one final time. The heavy, fist-sized balls flexed as they pumped the first shot of his ejaculation. His cock twitched dangerously inside Grayfia’s hot mouth, threatening to drown her in his seed.

Pop~!

With perfect timing Grayfia slurped noisily up the top quarter of his monsterous shaft and released the swollen cockhead with a wet suction pop. Not a second later, his tip flared and unleashed its creamy load, the reward for her dutiful service.

Grayfia closed her eyes as thick, powerful jets of creamy, sticky cum blasted up from between her tits, splattering in a big mess all over her face and hair. Issei groaned loudly, bucking his hips up into the bountiful valley of her tits, where his cock twitched like crazy, firing shot after shot of his long, ceaseless climax.

“Oh my...” Rias said in awe, watching with big, unblinking eyes as the ‘Strongest Queen’ was caked in cum. Issei’s cumload was WAY bigger than it had any right to be, far more than she’d been anticipating, even with how hefty his balls were. She let out a long, hot moan as she watched it, slightly trembling.

“Haaaah... Haaaaah...!”

By the end of it, Grayfia had been showered in white creamy cum, and Issei was panting roughly. Rias held him from behind, holding his head between her tits while she rubbed his chest and cooed in his ear, “Heheh, that was amazing, darling..! Look how much you let out. You must’ve been pent up, fufufufu~! Did it feel good..?”

“Y-yeah..! It was amazing..!” Issei said with a voice full of awe, amazed at how good real sex felt compared to masturbation, “The most incredible feeling in the world..!”

Grayfia, with her tits still trapping Issei’s twitching cock in their tight cleavage, wiped her eyes of the cream that covered them. As she opened her eyes and saw Issei looking down at her, she merely offered a small smile, “What a mess. I’m glad to have offered you some relief, Young Master...”

Issei smiled dumbly.

“So...” Rias’ voice was still hot in his ear, “Tell me, Grayfia... how does my future husband taste..?”

Grayfia stared at her silently for a moment, face caked in cum, then stuck her cum-covered fingers in her mouth. She nodded, “Acceptable.”

Rias seemed to pout at how unemotional Grayfia’s response was.

The servant continued, “With an improved diet and magical rituals, the taste can be greatly enhanced... Oh my.”

The two women looked down between Grayfia’s big tits, where Issei’s cock was still twitching erratically, like a dog wagging its tail.

Grayfia’s eyes slightly widened, “Are you unsatisfied, Young Master..?” She said with a slightly confused tone, “I thought humans...” Then she bowed her head, smiling to herself, “I apologize. I should not think of you as a human, Issei-sama...”

“Heheh...” He chuckled lightly, “What can I say? In the presence of such sexy women, there’s no way I’d be done after just one round! I-I might cum a little quick, but I’m confident in my staying power! On a school holiday, I once jerked off sixteen times without stopping!”

...

His proclamation was so bold and proud that the two women were speechless. Grayfia’s mouth fell open. For being an embarrassed virgin, Issei had a strange pride when it came to these kinds of things. Now that he’d seen his first real pair of boobs, and better yet, even experienced a titty-fuck, he was bold enough to boast about it.

“Fufufu~!” Rias lightly giggled.

Grayfia softly smiled and gave a slight inclination of her head, “You are quite impressive, Issei-sama...” She brought out a cloth from somewhere and began wiping her face, “I understand. If you need further relief, then allow me to begin again... I will tend to your needs until...” She flicked her gaze to Rias, “...until your balls are drained dry.”

“Oooh..!” If Issei wasn’t still at full mast, that one incredible phrase would have his dick hard as diamonds. Even said impassionately as she did, it felt so erotic. He still found it hard to believe this all-business type maid would really give him such a dirty titty fuck and let him paint her face like that. Her promise re-invigorated him.

“P-please do!” He happily exclaimed with a dirty look on his face. Then he looked down at her magnificent, cum-covered breasts, “A-as much as I’d like another titty fuck... P-please, let’s go all the way! Rias, you said I didn’t need to keep my virginity, right? Please let me fuck your maid!”

“Heheh~!” Rias giggled at the excitement on his face and the way his cock twitched so honestly between Grayfia’s tits, “You sure are a shameless Fiance... but I don’t dislike it💞! Sure, go ahead, my love. That’s why she’s here, after all. She’s YOUR maid now Issei, and if you order her to pull down her panties and sit her fat ass down on your cock... fufufu, she’ll obey.”

“Nngh..!” Issei groaned as his violently twitching cock throbbed in Grayfia’s titty confines. He couldn’t hold back anymore, “G-grayfia!” He said in a loud, boisterous voice, “Get on the bed!”

The silver haired servant, lowered her head in obedience, “As you wish.”

Rising from her knees, Grayfia’s naked breasts hung heavily from her chest. Bare in all their glory, right in front of Issei’s eyes. If they weren’t still covered in his sticky seed, he wouldn’t have been able to resist grabbing them again.

Grayfia, the perfect servant, read her new master’s thoughts without difficulty, and the floor around her feet lit aglow with magical light. A magic circle appeared, flashing over her form and cleaning her body in an instant. Once again her humungous milky breasts were clean and flawless, irrestible to Issei’s lecherous gaze.

Issei couldn’t believe what was happening to him. His eyes devoured the plush, fuckable body of the silver-haired MILF with bottomless lust. This WOMAN was going to be his. She’d relinquished her hourglass curves to him, giving him free access to her unbelievable body. In just a matter of moments, they’d be joined in sinful ecstasy right here on his new bed inside the Gremory’s lavish castle inside the Underworld.

He was in bed with devils... and couldn’t control himself any longer.

That rousing beast inside him finally took over. With a dragon-like growl, he grabbed Grayfia’s meaty, childbearing hips and pulled her toward him.

He buried his face once again in her heavenly cleavage. His hands and mouth devoured the vast globes of her boobs. One hand sank into the fatty flesh, firmly groping and kneading her breast for all its worth, while his mouth sealed over her perfect, delectable nipple. He sucked hungrily, thirsting for milk from her teat while his other hand wrapped around her waist and pulled her tight into his embrace.

“Aaah..!” Grayfia let out a surprised womanly sound.

The sound fanned the flame of his lust even higher. That noise was a trigger, reminding him that this was, in fact, a woman. Not an emotionless servant but a woman.

HIS woman.

A new goal sprouted in his heart. Make this woman moan. Hear the wonderous music of her passionate voice in the throes of sex. Make her scream his name and declare herself as his woman.

Issei would make that happen no matter what!

Issei now thought he had two good traits. His determination and his girthy cock. So now he was determined to make her scream with his girthy cock.

With a low growl, he grabbed her fat ass, digging his fingers into the softness of her round butt. Then he pulled her forward and flipped her over. Grayfia let out a soft noise as her back hit the bed, and instictively wrapped her legs around his waist.

His fat cock slapped down on her pussy mound, draped heavily across her panties, and reaching all the way up to her belly button. Rias gasped at the most blatant display of his endowment. She gulped slightly, seeing just how DEEP that throbbing beast would be plunged into her maid.

Issei huffed as he started grinding his hips. With one strong hand on her ass to lift her hips up to meet his, he rubbed his massive length against her pussy while looking down at her beautiful features.

Her mouth was slightly parted with a light breath, but she had regained her composure. Her angelic, snowy white features looked up at him with a patient, expecting gaze. She didn’t moan, nor did she look intimated by the burly cock threatening to re-arrange her insides. She simply laid back and waited.

He dove back in and stole her lips in a hot kiss, eager to taste her sweet saliva again. Immediately, she responded back, dueling his tongue with a matching intensity. Grayfia did not cut corners in anything she did, including kissing. So when he stole her lips, she gave him the hottest, wettest, sluttiest kiss she could muster.

“O-oh wow...” Rias muttered to herself, lowering her voice as she realized the two had probably forgotten all about her already. At least, Issei had.

Issei grabbed a fistful of her overflowing breasts, eager to sink his hands into the firm fat once again. With obsessive passion, he groped her plump boob while trying to wrestle her tongue into submission. His cock was hard and energetic, sliding up and down the hot mound of her panties, eager to drive home into her tight womanly folds.

Finally he broke their sloppy kiss, once his patience wore out and his pure desire for pussy won over his facination with her tongue. He crawled back down between her spread legs so he could reach the band of her lacey dark blue panties. Then, with an almost reverent carefulness, he peeled that tiny pair of expensive lingerie down her thick thighs.

He growled with excitement, eyes devouring the pink tenderness of Grayfia’s flawless pussylips. Her lower lips appeared untouched by man, with how pure and pink they looked. Issei drooled, wanting to dive between her legs and taste her most intimate place for himself, but his overwhelming desire to just ram his thick cock into that tight-looking hole was too much.

So Issei mounted her, lining up the thick pillar of his massive cock with her delicate-looking quim.

“W-wait..!” Rias exclaimed.

Issei, too far gone to think about anything but sex, growled as his slid his cocktip across Grayfia’s wet lowerlips.

Rias softly whimpered at the look in his eyes, a hungry, primal look that was pointed at her servant like she was a piece of meat. She shuddered with perverse delight.

She quickly scrambled forward on the bed, her big tits nearly spilling out of their tight bra, and reached for his cock. Tenderly, she wrapped her fingers around it, feeling it still slick with Grayfia’s spit. She touched it carefully, like she was afraid merely laying her hands on this magnificent endowment would steal away her purity. Or perhaps make her forsake her family responsibilites, and spread her legs for this bitch-breaking cock of her own free will.

Regardless, Rias wore a lewd grin as she licked her lips and slowly pushed Issei’s thick man meat down lower, lining up his bulbous, fist-sized cocktip with the tight, quivering hole of Grayfia. She wanted to do it herself. To dip her future husband's cock in her own servant’s willing pussy.

“G-Go ahead, Issei...” Rias said with a shuddering breath, “F-fuck her..!”

“Nngh..!” He let out a beastlike groan as he drove his cock forward.

“Hn.!” Grayfia shut her eyes and whimpered as her walls were stretched wide by the thick invader.

Issei groaned loudly. Grayfia’s pussy was incredible! Her soft, slick walls wrapped around his cock like a vice. He felt her walls quivering like they were sucking him further inside her eager pussy, begging him to drive his cock all the way to the root inside this willing MILF.

The sensation was incomparable to masturbation. It was unlike anything he’d ever felt before. Amplified by the incredible satisfaction of realizing he’d done it. He’d lost his virginity and he’d lost it to the most beautiful, regal-looking, uttrely BUSTY, woman he’d ever seen. An actual devil maid MILF! A woman who was way out of his league, but spread her legs and welcomed him into her cunt with a gentle, ‘As you wish’.

He couldn’t hold himself back.

“Grayfia..! Grayfia..!” He shouted her name as he pinned her to the bed. She merely let out a gentle sound as he grabbed her arms and pinned them above her head. Then he started thrusting his hips without restraint.

His massive cock split her poor, delicate pussy open with its incredible girth, sliding through her slick wet tunnel roughly enough to make lewd, wet sounds every time he drove his dick deeply into her.

“Hng..! Hngh..! Hggnh!”

Plap~! Plap~! Plap~! Plap~! Plap~!

Issei’s hips slapped noisily against Grayfia’s spread legs as he finally drove his dick as deep as it could go into her pussy. It was a miracle the monstrous thing fit. All Issei could think, feeling the way Grayfia’s cunt was massaging his cock with trembling walls, was that Devils were built to take cocks.

Rias’ mouth hung open. She was panting with lustful, tingling excitement. Her eyes were wild with desire. She was watching her beautiful, precious servant, Grayfia, getting fucked so hard by the man who would become her husband. She watched in rapture as Issei’s pillar of meat cored into Grayfia’s soaked snatch, so thick and mighty that she could see it bulging from her belly every time it battered through her inner walls.

The maid, no matter how hard she tried to keep up appearances, couldn’t possibly keep a straight face under such ferocious pounding. Her eyes were squeezed shut, her teeth clenched as she tried to hide the moans and whimpers that threatened to escape everytime that giant-sized dick carved through the sensitive walls of her pussy, making her nerves fire non-stop with the pleasures of sex.

“Hah, hah, hah..!” Issei was panting roughly, flexing every muscle in his body tight as he used all his strength to fuck her as hard as he could. He was losing his mind to passion, looking down as he pinned this busty MILF beneath him and fucked her without regard. Her face tightened in pleasure, her giant tits bouncing and jiggling like crazy on her chest, all while he was fucking her with selfish desire.

He felt mindless because the only thing he could think of was fucking this busty, sexual creature as hard as he could. There was nothing left he wanted in the world except for one last singular desire.

To cum inside her.

He was dying to blow his massive, churning cumload inside the fresh, untouched womb of this incredible demon maid.

So he pressed her firmly into the mattress, sealing her soft lips with a hot kiss as he bottomed his cocked out in her tight tunnel. Like a perfect fit, his cockhead shoved roughly against her cervix, cocktip flaring wide. Then he let it all loose with a mighty groan.

Rias watched transfixed as Issei’s huge nuts flexed as they pumped a thicky, heavy load of fresh hot cum into Grayfia’s quivering hole. She thought it was cute the way his hips kept bucking further into her, like he was trying his hardest to plant his seed in her fertile baby room. Grayfia, she noted, was doing her part, keeping her legs locked around his waist to make sure her pussy was milking every last drop of cum from his overstuffed balls.

“Amazing...” She said in wonder as she watched the final climax of their hot sex. She could see thick globes of his semen start to pour from the tight seal of their joint sexes. Issei’s stupidly big cumshot was proving too big for Grayfia’s pussy to take completely.

“Nngh..!” Issei was still groaning, rolling his hips into Grayfia’s amazing pussy. Her tight walls coiled around his cock, greedily drinking down the semen he kept pumping ceaselessly into her core.

He panted with exhaustion, his human muscles aching from his rough treatment of her cunt. Then he looked down at her.

Grayfia was looking at him too, her lips still wet with his spit. They curled into a soft smile as she closed her eyes and let out a breath, “Are you... haaah, satisfied Young Master?”

Then he realized something.

He had cum buckets, way more than he’d ever shot out in his lifetime. But... what about her? Did she..? He couldn’t tell. In the heat of his passion, he wasn’t even thinking about her pleasure. That irritated him a lot suddenly. What was he, a monkey?

He justified it in his mind; It was the Devil’s allure that made him go crazy like that. These supernatural beauties drove him mad. But what was done was done. The only thing he could do now was make up for it.

So silently, in his heart, Issei swore a promise.

While squeezing Grayfia’s abundant titties in his hand, he silently swore, ‘Grayfia..! I’m gonna make you cum a hundred times..!’

He’d sworn before he even shoved it in that he’d make her scream like a woman. Well? What did he have to show for it? Even as he had brainlessly bucked his hips into hers, she hadn’t let out more than a gentle groan.

He wanted to see her beautiful features warped in ecstasy~

He wanted to hear her angelic voice scream in name in bliss~

He wanted her to beg him for more, to drag her nails along his back and swear herself to him forever~

There was a gleam in his eye. Something inside him had changed. Maybe it was just the infamous ‘sage mode’ that came after cumming, or maybe an elevated version of that, that only occurred when cumming inside of a real woman, but he felt different than before.

He felt better.

Now he was looking down at this busty MILF, softly panting on the bed beneath him. Her nakedness was completely revealed to him. Every inch of her sensual curves, her giant titties, her curvaceous hips. Her pure-white skin was slightly flushed red as she huffed and panted. Her huge tits heaved on her chest with every labored breath, softly wobbling.

He desired her. He wanted her more than anything he’d ever wanted in the world. He must be the greediest guy on the planet. He’d already been offered up a big-titty red-haired wife and here he was already lusting after another.

But that was who he was.

But now, after cumming inside her and getting a little clarity back, he realized what he wanted was more than just tits and ass. More than just her clenching cunt.

He reached down and kissed her. Like always, he was furiously passionate, twirling his tongue around hers in a lewd, wet kiss fueled by his lust.

Then he looked into her eyes, and said with all his heart, “I love you!”

“H-huh..!?” Grayfia gasped, her lips wet. Her eyes were wide with pure astonishment.

“Oh my..!” Rias too, was shocked speechless, with wide eyes and a hand covering her mouth.

He grinned, “Yeah. I’ve decided! I love you! I love your big tits! Your massive ass! I love how tight your pussy is and how good it feels to fuck you! That’s why I’m going to make you my woman..!”

“...” Grayfia was truly speechless.

Issei grinned wide, and suddenly grabbed her legs. Grayfia softly yelped as her legs were jerked up in the air, and Issei’s massive, still-hard cock was primed at her freshly creampied pussy in a dangerous piledriver position.

He grinned, “Get ready. I’m gonna fuck you until you can’t hold back that pretty voice anymore. I want to hear you scream my name and admit you are my woman.“

Grayfia suddenly swallowed, seeing the fiery determination in his eyes. Her pussy quivered weakly, like it was cowering in submission to the burly bully of a cock towering over it.

She quietly wondered, “Can my pussy really take much more of this..? He might actually do it...”

There was a sliver of something new in her gleaming red eyes. A blooming bit of a respect, and just the faintest hint of desire. She began to see this human as her genuine master. A real man worthy of serving. Someone she could bow at the feet of and serve as his maid, his concubine... his woman.

Rias to the side had a red face. She blushed as if she’d heard her Fiance say sweetest thing in the world, not some filthy, horny dirty talk to some other woman he was fucking.

“Do it, Issei..!” Rias said breathlessly, watching him with wide blue eyes full of awe, “Make her yours..!”

Issei swore to make good on that promise, and turn Grayfia into his woman... Even if he had to fuck her nonstop until his wedding day.

_________________________________

End of Chapter

A/N: A little later than I wanted this to come out but I'm happy with how it turned out. I had a few different ideas for DxD but I didn't want to start with anything too complicated. I hope you enjoyed the simple smut. 

If this continues, the idea is a somewhat slower burn for Rias while teasing her with different women. Maybe other MILFs and/or her peerage before their eventual wedding day.