WARNING: BDSM, bondage, role-play, MILF

To everyone wondering, lemme speak for a bit. Storm Master 567 is my all-time favorite writer on this site and I have been greatly inspired by his fanfics to come up with this, and he has given me his blessing to be allowed to let this work be similar to his. This is a PURE SMUT fanfic, featuring your favorite DxD girls as well as girls from other series and they all take place in an AU world with no supernatural realm or whatever. Point is, we'll be having plenty of fun in this fanfic XD. NOW LET'S GET STARTED! (Harem list is at the end of this chapter, review if you want a girl to be added)

P. S. To those readers who have read my Dragon's Charm fanfic, I'm sorry for discontinuing it but I have something to make it up to you! This fanfic is not only dedicated to those horny teenagers out there, but also dedicated to those readers who have enjoyed my smut-writing there.

Disclaimer: I don't own Highschool DxD or any of its characters…

Grayfia

(Hyoudou Residence)

Standing in the shower was one Issei Hyoudou, letting the water cool down his warm body. He had a look of displeasure on his face, before he lathered the shampoo all over his brown locks and started grooming his hair. Another day of school had passed for him, and dare he say, he didn't appreciate the events that just transpired a few hours ago.

"Why do I have to save their asses every time they do something stupid?" Issei groaned to himself as he made sure every part of his scalp would be full of bubbles. His two perverted friends, Matsuda and Motohama, were off peeping during their lunch break earlier and it didn't end well for the both of them, at least for the time being.

They had begged for their pal Issei to save them from the wrath of the kendo club members and luckily for them, he agreed to do his best in appealing for mercy from the girls that his friends had peeped on, but didn't guarantee their full safety. However, that decision would soon bite him on the ass when he found out that a member of the student council had reported what happened and he would be the one answering for his friends' malicious acts in the principal's office tomorrow.

"Ah, fuck it… best be prepared for what's to come tomorrow at Grayfia-kocho's office…" he sighed, rinsing his hair through the running water before applying soap to his body next. "Wow, in all the times I've answered for what those two idiots have done, this has gotta be the first time that I'm going straight to the principal's office… hah, I wonder why…" (A/N: Kocho - Principal)

Issei Hyoudou was a 2nd year student at Kuoh Academy, who was considered a "chick magnet" by most of the boys' population due to his unwavering kindness, and heart of gold that won him the hearts of many women, students and teachers alike. He was also described as "every girl's wet dream". Not to mention the fact that he was also quite handsome and cute at the same time, which only added to his rapidly-growing reputation. He was also fairly consistent with his grades, maintaining everything above average and passing his exams smoothly. And yet, he didn't seem to pay any attention at all to what was around him, acting all oblivious to what women felt for him.

However, this did not mean that he was truly innocent.

"W-Wait a second…" Issei said to himself as pictured the principal of Kuoh Academy, Grayfia Lucifuge, in his mind. She stood at 5'8 and had an hourglass figure with all the right curves that were perfect with whatever she wore. Grayfia had back-length silver hair that features a long braid on each side, while the rest is let down which ends in twin braids that nearly touched her shapely womanly hips that held her plump ass that further showed off her curvy MILF body. Her chest, just thinking of her huge D-cup rack almost made him wish to get motorboated and get buried between them.

Yes, Issei was also a pervert. A very big pervert at that fact.

But, knowing his own personal limits, he preferred to keep his own fetishes and desires to himself because he wanted to have a stern and upholding image in the eyes of many, not wanting to be like his perverted friends who were looked down upon by the school. Apparently, Issei had a thing for being the dominant/sadistic one in sexual acts and found out that it was great turn on for him. While remaining oblivious to what other girls felt for him, he had countless sexual fantasies with some of the females in his school that he had hung around with the most, and some that he had some kind of crush on.

One of them being the sexy principal of the school itself, Grayfia Lucifuge.

"I-I can't think like this, I have homework to do." he shook his head, desperately trying to get the silver-haired principal out of his head. "She's the school principal, she's the school principal." Issei reminded himself.

"Yeah, the principal without a husband…" a darker part of him reminded that Grayfia's husband, Sirzechs Gremory, had died a few years ago which prompted the woman to go back to her maiden surname, Lucifuge.

"Screw this, I have homework to do!" Rinsing himself under the water one more time, Issei grabbed his towel and wrapped it around his waist, before walking out of the bathroom.

(The Next Day; Kuoh Academy)

Issei Hyoudou was sitting in class with a slightly scrunched face. Not only was he going to be faced with trouble with the principal later on, but he was having some problems down there. Issei was struggling to contain his lower half right now as he sat in his last class while staring at the gorgeous teacher, Rossweisse Andersen, or Rose for short. She was the youngest teacher in Kuoh at 19 years old, with enormous tits that rivalled even Grayfia's, and some could say that the two had a somewhat similar look to each other. The white t-shirt that she was wearing underneath her dark blue sweater strained against her bountiful bosom with her black skirt stretched because of her plump bottom that begged to be spanked and fucked.

Like the principal, Rossweisse had been involved in many of his naughty fantasies. Just recently, he's been daydreaming of having hot, steamy sex with her and Grayfia at the same time and remembering the images of those in his mind made his pants strain even more.

Blame his current situation for it.

Their sweaty bodies writhing in ecstacy while he made Grayfia eat out Rose's cum gushing pussy while he drove himself in and out of the MILF's tight cunt, slapping her red booty multiple times…

He could still hear the womanly screams of pleasure. Crossing his legs, he focused back on the lecture that was coming to a close. "Goddammit, I need to focus! There's only a few minutes left!" he yelled to himself, desperate to calm down the growing tent inside his pants.

What he didn't know was that the bodacious silver-haired teacher was sneaking little glances at the young man sitting in the front row. "So cute~!" Rossweisse thought to herself, while talking about something about the lesson that she wasn't really paying attention to. Rose had a little crush on her student, as she had seen how Issei was very different compared to other boys in the academy and she was glad at the fact that he was attractive in his own right.

Rose, even though she was at the dating age, had never had a boyfriend before, so she had no real experience when it came to things about love and romance. However, watching how Issei had developed so greatly just after a year of being his teacher made her quiver in desire whenever she thought of him. Issei had even been the subject of her masturbation sessions whenever she had time to herself. "If only I had more courage and time to tell him what I feel!" she thought to herself as she stared into his brown orbs. "Maybe I could hold a private tutoring with him, ufufufu~" the horny teacher told herself, imagining how a simple activity like that would somehow escalate into something more between her and Issei.

Rossweisse would have continued her subtly ogling if the school bell had not rung just a few seconds later. Letting out a quiet sigh, she looked at the whole class with a smile. "Alright class, remember that there will be a test tomorrow, so nobody should be late. Otherwise, I'll close the door on you and you won't be able to get in. I'll see you tomorrow." she announced, slightly amused when she heard the groans of protest from her students of having to study for an upcoming test before leaving the room.

"Oi, Ise." a familiar voice called out to the brunette who was about to sprint towards the principal's office. Sighing lightly, he turned to his friend, Matsuda, with a smile.

"What's up, Matsuda?" he greeted his friend in a somewhat monotone voice, reminding himself that it was because of his friends' antics that got him into trouble.

"Nothing much." Matsuda shrugged carelessly, rubbing the back of his head. "Just wanted to ask if you got anything planned for today. Me and Motohama are planning to go out for some coffee, you want to come? We won't be doing any peeping today, I promise." he asked his friend.

Issei's eyebrow twitched in irritation. "Did you forget that I'm heading straight to Grayfia-kocho's office because of what you and Motohama did? Or do I have to remind you?" he said, raising his hand as he was about to smack Matsuda on the head.

"Alright, alright, alright we're sorry, okay?!" Matsuda pleaded with a nervous grin, raising his arms up with defeat. "We had no idea that this uhh… problem, would get to the principal, but… good luck with her. We're just here in case you get… expelled or something…" With a wave, Matsuda quickly left after seeing Motohama rush out of the room out of fear that Issei would beat them up.

"Good, they're gone… now to get going…" Taking a deep breath, Issei then left the bedroom and made his way to the principal's office, preparing himself for what the silver-haired principal of Kuoh Academy had in store for him.

(A Few Minutes Later; Grayfia's Office)

In her office, Grayfia was waiting patiently for the young man that was due to come knocking on her door after classes, because he had to take responsibility for what his two degenerate friends have done the day before. However, unbeknownst to Issei Hyoudou, she had a surprise for him as well.

With a blush on her face, Grayfia was sitting on her desk, crossing her legs sexily that showed off her already soaked panties and garter-belt. She unbuttoned the first few buttons of her shirt, letting a good amount of cleavage to be shown, hoping to arouse Issei and get him to easily give in to her advances. She put her hair in a bun to make it more easier for her to move around, knowing that it gave her an even more beautiful sight.

"This is so naughty but so exciting~!" Grayfia thought to herself with a perverted grin and giggled like a schoolgirl in love. She couldn't wait for Issei to arrive so that she can seduce him into fucking her brains out inside her own office. As crazy it might seem, the very principal of Kuoh Academy had developed an attraction towards Issei Hyoudou for the past year; the same attraction that she felt for her late husband except that this was much stronger than her feelings before. Like with Rose, she watched how Issei had grown into the fine man that he was today in just the span of twelve months and it made her feel like she was another one of his fangirls, which she honestly wouldn't mind being a part of. He had his flaws here and there, but he was still at the adolescent stage and had plenty of room for change and improvement.

The sole reason that she had called Issei to her office today was so that she could have him to herself and finally fulfill her lustful desires, and she couldn't care less about giving him punishment for what his friends have done. Actually, him taking responsibility for his friends' actions made Grayfia like him even more, as it proved just how far he was willing to go for his friends and the ones he cared about. She couldn't take it anymore and being the single woman that she was, she wasn't able to fully satisfy her sexual desires and she needed Issei to fill the gap that her husband had left.

Wait that wouldn't be a bad idea, would it? Punishing him by tying him up and forcing him to fuck her into oblivion… that doesn't sound bad…

The naughty woman's mind was already excited at the thought of having Issei pound into her relentlessly against her desk, and she even had something that will make her shake in ecstasy planned in her desk drawer; something that she had never tried with Sirzechs but had the most chances of doing it with Issei. Shaking her head to keep her growing arousal calm, she looked up to see the door slowly opening, signifying that her guest had arrived. Regaining her breath, she prepared herself to play her role for a bit before proceeding to her original plan.

Issei Hyoudou was not prepared to see the principal of the school to be dressed like this. While he knew that Grayfia Lucifuge had been a subject of almost every boy's fantasy in the academy, he had never expected her to look so amazingly sexy at the moment while giving off a "fuck me senseless" vibe. His eyes widened as soon as he realized how beautiful and sexy she was right now; the school principal who was supposed to look strict and proper was looking like some whore, but the glare in her eyes made him stop thinking of anything indecent almost immediately.

"What the hell is going on? Why is she dressed like this?" Issei thought with wide eyes as he took a step back. He had to gulp and think of other things in order to suppress his growing arousal, because the freakin' principal was in front of him, who had the power to suspend or even expel him from school if she had the reason to.

"Hyoudou-kun of Year 2-B. Do you know why you are here?" Grayfia asked sternly, writing something on the pad in front of her that seemed like a letter of offense before she grabbeda ruler and started to play with it using her hands.

"Hai, kocho-sensei." Issei replied in a stern voice, not wanting to act scared in front of the principal; it was, after all, not his fault that he was brought here right now. He was just taking responsibility for what the two idiots, who were his friends, have done against the school regulations. "I'm answering for what my two classmates have done yesterday, as they have committed another act of indecency on the members of the kendo club."

"That's right." she announced, snapping the ruler in half. "And this is what, the fifth time this week that those friends of yours have broken school regulations? I've had it with sending verbal warnings to them… a week of suspension seems enough for an appropriate punishment for them." Seeing the look of slight shock on Issei's face, she raised her hand and sighed. "Don't look so down, because you are not at fault. I understand that you are only here to take your friends' places, and I only need you to relay this message to them."

"Sensei, is there any other way to lessen the punishment on them?" Issei asked, leaning forward a bit. Although he didn't like how Matsuda and Motohama handle their perverted thoughts and urges, they were still his friends and he didn't like the idea of them having to go through such severe consequences for what they've done. At the very least, Issei would want to lessen the burden on them if he can't fully prevent it from happening.

Grayfia hid a smirk from him in order to keep her intentions secret. He reacted just the way that she wanted to and she knew that she had him in her grasp. "What would you be willing to do for your friends, Hyoudou-kun? If you're going to act like some saint to them, at least make some sense in what you are trying to say."

Issei scratched his head as he thought about it deeply. "Uhm, I could… do something for the school, I guess? I don't know, just… if there's a way for me to lessen their punishment, let me do it. They might be perverts, but they're still my friends." he shrugged, looking to the side to hide a disappointed expression on his face.

It was the time to act.

Grayfia flashed a sultry smile and spoke with a voice that held her excitement before she leaned forward, letting him have a view of her enormous breasts. "Well then, Hyoudou-kun… how about you tend to this body of mine?" she whispered huskily.

Issei was sure that he had cotton in his ears as he had turned his head to the side in order to hear what she just said. "I'm sorry, what?" he asked in slight shock, only to be greeted by the sight of the sexy principal's bouncing jigs that was sure to be a view to remember in his head.

Giving the male student a saucy smirk, she slowly ran her hands up her body and unbuttoned a few more buttons on her shirt that made Issei blush deeper. "I've been feeling so lonely ever since my husband died, Ise-kun~ I need a big strong man to help me get over this pain in my heart." she said, flashing him a seductive look.

"Uh, Sensei…?" he replied, leaning back slowly as he felt a bit uncomfortable with Grayfia's new attitude towards him. He knew her as a strict and upholding principal who would not hesitate to give punishment to those who deserve it, but the woman in front of him was acting otherwise. However, his primal urges were beginning to get the better of him as the bulge on his pants begun to grow. "I-Is something wrong?"

Grayfia let out a throaty moan as she unbuttoned her shirt completely, exposing her breasts to the open air. She wore no bra underneath, letting Issei see her full cleavage as well as her hardened nubs that got aroused just by the thought of him pouncing on her like a wild animal. "Can you help me, Ise-kun~? I know that you have always rejected your female colleagues, but I need you. I've liked you ever since you stepped foot in this school."

Issei would have responded immediately to her had it not been for his shock getting the better of him that he couldn't resist asking questions. "Sensei, what the hell are you —"

The silver-haired woman had cut him off when she leaned forward a bit more in order to close the gap between them as she engulfed his lips with her own in a deep kiss, closing her eyes in order to savor the sensation she was feeling. Issei's brown orbs had widened as soon as he felt her lips on his, and it took him a while for him to fully give in and enjoy the moment by returning the kiss with just as much force and passion. His mind had no idea what was right or wrong at the moment, and thus he could only rely on his instincts right now, which were telling him to let loose and take advantage of this moment.

After all, it wasn't everyday that one of the girls in his fantasies would walk up to him and kiss him like this.

Grayfia could tell that Issei was slowly giving in to her action and she couldn't be any more happier that the boy was returning the kiss, signalling her to go for the next part of her plan. She took his hands and planted them on her bouncing jugs, letting him feel her hard nipples in his palms. Issei opened his eyes as soon as Grayfia separated from his lips, and he didn't even care that his hands were now on her breasts, as his lust was about to take over.

"Ise-kun, since you want to know how to lessen the punishment on your friends, I want you to fuck me~" she whispered huskily into his ear, giving it a slow lick that caused Issei to shiver. "Pound into this slutty principal and make her yours… I've been so indecent myself, so you need to teach me what's right."

A few seconds passed, and all Issei could think about was the last few words that she whispered to his ear, as the young man's innocent and prim exterior was broken down by his fast-growing arousal, judging by the size of his erection inside his pants.

The MILF moaned loudly when she suddenly felt Issei's hands squeeze her boobs roughly. "How can I say no to such a beautiful principal?" Issei whispered in a low tone of his own, showing that he had gave in to his lust quite easily, being overwhelmed just by the sight of the silver-haired woman's body. Turning his attention to her breasts, he would have continued to ravage them if only Grayfia hadn't used another ruler to gently bonk him in the head.

Looking back up, she wagged her slender finger at him as she faked a frown. "Nuh uh, Ise-kun. Let me do this properly, since you are inexperienced in this." Grayfia said in a lecture-like tone that a teacher would use on her students.

Happy with the reaction that she got from him, Grayfia stepped back and let her hands fall towards the hem of her shirt, as she slid it off her slender shoulders, giving way to her upper body on display for Issei. The young brunette subconsciously licked his lips in hunger as he realized that one of his hidden fantasies was about to come true, making him think for a second if he was actually dreaming or not. This seems to be too good to be true, but Grayfia wouldn't dare to strip in front of him if she wasn't serious about this, so he took it as the go-ahead sign for him to make his move.

About to lean in and satisfy his desires, she once again gently stopped him by holding him by the sides of his face, looking straight into his eyes. "Gently, you got it? You have to do it gently since you're still a virgin." she advised with a little smirk on her face.

Too lost in his own cloud of lust to even apprehend what she wanted to happen, he quickly made his way to her and ran his tongue all over Grayfia's left boob, making sure that it would be something to remember for the both of them. The sudden lick made her moan a little bit before it grew louder with each action that his tongue had inflicted on her delicate. While she did like the rough stuff, Grayfia wanted to start this session at a slow pace before really getting into the good part since Issei was indeed a virgin and needed to learn more about how to please her properly.

Little did she know about Issei's hidden fetish and how he had always wanted to do it on a woman he's had fantasies about.

"Y-Yes, just like that!" Grayfia nodded her head with a large smile on her face, fully enjoying the attention that Issei was giving her tits.

Regaining some of his conscious mind, Issei slowly slid his unused hand down her creamy flesh, caressing her skin and sending goosebumps to her very core. Grayfia gave light moans of appreciation to his light touch before letting out a louder one when she felt Issei's fingers brush against her panty-clad womanhood. "You're so wet, Grayfia-sensei." His low voice had sent a pleasing vibration across the woman's flesh, making her even wetter that she was starting to crave for more.

Issei could only smirk as he now focused his tongue around Grayfia's hard nipple, realizing now that this was no dream and that this was real. Kuoh Academy's own principal was here before him, and was practically begging for him to fuck her brains out. He then noticed that his fingers were already drenched with Grayfia's dripping juices, which meant that she was really turned on by this and he loved it! "This is getting too much for my pants to even handle." he thought to himself as he began to suck on her nub.

Getting tired of the slow teasing, the woman decided that it was time for him to take it even further. She could still feel his fingers sending shivers all along her body, but she managed to focus her gaze at Issei. "Take them off. I want your fingers directly!" she demanded in a harsh tone, referring to her blue skirt that stretched all the way to her lower legs.

Chuckling slightly, Issei didn't listen to her and pushed her towards the wall behind her quite hard that it caused Grayfia to yelp all of a sudden. Recovering from the impact, she didn't even have time to say a response when she felt him pin her arms above her head and plant short but sweet kisses all over her neck and collarbone, making her let out gasps of pleasure that filled the entire office. Issei leaned forward even more and licked her earlobe, before he started to speak in the same low voice that he had used on her earlier.

"It looks like kocho-sensei needs to be punished for such indecent acts in front of a student," he breathed out as he bit her earlobe slightly. Grayfia's juices were dripping all over the floor with how wet she had become and she couldn't even tell how much she wanted to have his big juicy cock to pound into her right now, but she couldn't do anything to force him to do so in any way.

"Yes, punish this principal for being so naughty! I deserve it for acting like a pervert in front of a student ~!" she moaned out with her tongue hanging by the side of her mouth as she felt Issei go down further back to her bountiful tits, mashing and squeezing them with his hands. Although "N-Not just my breasts~! Punish my pussy as well! Teach me a lesson that I would never forget~~!"

Deciding to agree with her, Issei cheekily pinched her nipples, eliciting a loud yelp from her before he slid down until he was directly in front of her crotch, which was still covered by her skirt. He immediately solved the problem by tearing off her skirt that caused Grayfia to yelp once more at how quick his movements were, as her wet pussy was now on full display before him.

"I-Ise-kun~!" she yelped, crossing her legs to cover her exposed womanhood out of instinct, and the blush on her face growing deeper.

"No panties, huh? I expected better from the woman I look up to in this school the most. I never thought she was a whore begging to be fucked into oblivion…" he smirked as he threw the ripped skirt over his shoulder, before staring directly at the sight that most men would kill for in front of him. The scent emanating from the MILF's twitching hole made him want to eat her out right then and there, but he wanted to make sure that he would be fully satisfied when this is over, because he had no idea if this was just a one-time thing between them or something more. He leaned his head closer and sniffed out her scent, which fueled his arousal even more than the bulge on his pants had gotten so obvious by now.

He let his hands trail up her womanly legs, sending goosebumps throughout her body, while gently massaging the doughy flesh along the way. "You're so fucking sexy." Issei whispered hotly, as the heat coming off Grayfia's dripping sex made him want to get this over with and proceed to fucking her senseless. Fighting down his lust, he finally got to her throbbing cunt that was begging for his cock to plunge into it, but he once again refused to give in just yet. Extending his tongue, he licked his way from the bottom of her slit to the top, enjoying the taste of her juices and finding it to be quite intoxicating.

Grayfia's mind was in distress when Issei was taking his sweet time to eat her out, and his tongue was giving her little teases of the pleasure to come and was driving her slowly insane against the wall in lust. She was about to yell at him to stop teasing her, only to moan out loudly and slam her fist against the wall when his tongue finally drove into her honey-pot. "Iya! S-So good!" Grayfia squirmed as Issei's tongue lapped up all the juices she had squirted over her clit and inner legs. The lewd sounds that Issei made as he slurped up her juices got the woman to thrust her hips into his face, as if she was personally inviting him to tongue-fuck her. "No~! I-I-I want your tongue directly, Ise-kun! That's not how you do it!" Grayfia moaned out heavily, her body flushed in arousal for direct contact from the boy that she was starting to fall hard for.

Looking up, he sent her a quick wink before he used both of his thumbs to open up her wet hole; she was not fully prepared for his tongue to dive right into her cunt walls, causing her toes to curl at the sensation and making her slightly tremble in response. "F-Fuck! Lick me more! Lap up all your principal's dirty cum while licking her tight cunt!" Grayfia's hot and sexy voice made his lower head twitch, forcing him to unbutton his pants to let his member free, yet he didn't show it to the horny principal, wanting to keep it as a surprise until the time was right.

Fucking the horny MILF with his tongue, he was in absolute love with the secreting fluids that washed over his taste-buds. Issei's left hand soon came up and pressed against her clit, rubbing it slowly in order to get the maximum stimulation from her. The stiffening and trembling of her legs around his head let him know that he had hit a good spot. "YES!" Grayfia shouted as Issei pushed her over the edge, her climax about to arrive. "I-I'm going to cum! Make sure to drink all this dirty whore's cum~!" Her demand was then followed by an orgasm that tore through her whole body, her eyes rolling back in the intense pleasure. Her head flew back against the wall and let out a silent yell, her tongue letting out some of her spit, while her face was set in a pleased grin as she breathed heavily.

Issei was doing his best to drink up all the sweet nectar that was flowing from Grayfia's throbbing pussy, not wanting to let it be put to waste because he aimed to be fully satisfied with this as well. And he wasn't going to be satisfied if he had let even a single droplet be wasted. Some of it had managed to splash on his face, but it didn't hinder his slurping up her juices as he found it highly arousing and erotic that Grayfia was such a squirter.

Her mind blown because of the intense orgasm that she just had, the silver-haired woman's expression flashed the perfect look of a bitch being pleased, as Grayfia moved away from him and slumped her head on her desk after covering her young lover in her tasty spunk. "That was amazing, Ise-kun~ You're so good at this for a first timer!" Grayfia complimented him with a large blush on her face. Sweat now rolled down her lovely body, staining the floor with it combined with her female fluids. "He made me cum harder than Sirzechs ever did!" she thought enthusiastically, licking her lips in satisfaction.

Licking up the last of the sexy MILF's leftover juices on his fingers, he stood up and turned towards Grayfia with a hungry look in his eyes, as he wasn't done yet. His brown orbs only darkened in lust when he saw her plump ass sticking out for him to see, and there were still traces of her vaginal fluids dripping down her legs and he had a perfect view of her puckering butthole. Unable to help himself, he gave the woman a hard spank to her butt.

"Iya!" she yelped out in shock as her tongue hung out, before she turned her head back to look at Issei, still breathing heavily as she turned her body to the side as well as soon as she realized what he did. "Oh, did you like my ass that much, Ise-kun~? You can play more with it if you —" she was cut off when Issei was suddenly on top of her, pinning her shoulders to the wooden desk below her with his strong, delicate hands.

"You taste so amazing Fia-chan. I want to have a taste of you everyday if it's possible." Issei said with a wide grin, now more excited than ever. The feeling of spanking a woman's ass had fulfilled another one of his sexual fantasies, and after seeing the red handprint he had left on her skin, it left his blood pumping and made him want more. The prim and proper exterior that he always showed to others was already gone, and only his hungry, lustful self had remained intact.

Grayfia's blush grew at the little nickname he gave her as well as the prospect of getting the same amazing oral pleasure everyday from Issei himself. She definitely wouldn't mind having mind-blowing sex with him everyday, and knowing that he has always been consistent with his grades, there wouldn't be any problem whatsoever. It was such a highly arousing thought that she let her stern persona go and pulled him, using her long legs, closer to her groin. Grayfia let her hands cling on to his broad shoulders before she brought him down to her lips in a deep kiss.

Issei made sure to give his slutty principal a taste of her own cum in between the battle of their tongues as he easily invaded her mouth with his aggressive demeanor that he had shown ever since earlier. He was not acting like a total first-timer, as it seemed like he knew exactly what to do to pleasure them both. Grayfia didn't mind her taste on his lips, as she actually found her own taste to be quite good. Locking lips and making out for a full minute, she leaned back and gave him a sultry smirk that sent his brain into gear after such a hot kiss.

"I don't mind being fucked by you whenever you like, Ise-kun… but now~" she tugged on his pants with one hand and used her strict voice to speak afterwards, as if she was giving him some sort of task to fulfill. "Take off your pants!" Without hesitation, Issei pulled his pants and underwear down in one swift move. His ragging prick sprung into the air and brushed up against Grayfia's twat as a result.

Her eyes widened at seeing Issei's incredible size when he was fully erect, no less than 9 inches and drool could be seen down the side of her mouth out of excitement at the thought of his massive cock fucking her good. "A-Amazing… s-so Ise-kun is this big… w-will that thing even fit inside me?" she mused to herself, a smile beginning to appear on her face as her slender fingers wrapped themselves around his meat rod before gently stroking him.

"Fia-chan." Issei growled out, making her blush at hearing his low tone once again as she turned her full attention to him. His hands reached for her shoulders again, preparing to jam her his rod into her waiting cunt, only to be angry when Grayfia had moved away just before he could touch her. "W-What?!" his lust-clouded eyes darkened with anger, thinking that he was getting rejected in the middle of their private time together.

Upon moving away, she could hear his growls and could only smirk teasingly. Looking over her shoulder, she stuck out her bare bottom to his direction and spoke in a more seductive tone than earlier. "Don't worry, Ise-kun~~ you'll get this pussy, just wait for a bit, fufufu~" she shook her ass as she leaned forward and opened her drawer. "I just thought of something that could make this even better, something that we could use when you fuck me again~"

Her silver eyes darkened in sinful lust as she revealed what she took from her drawer; Issei stared in slight shock at the ropes that the busty MILF was holding in her hands. "Tie me up and fuck me like there's no tomorrow~!" Grayfia exclaimed happily, walking back towards him with a lewd smile on her face.

"Don't mind if I do!" Issei said in a happy voice, a large grin erupting on his features. Stepping back, he let Grayfia lie down on her desk in a very erotic position, before he swooped in to make his move. The teen had bound her legs to her wrists, showing her gushing cunt lips, before tying her two hands altogether with her legs above her head. Her long silver hair was set free with a few rogue strands sticking to her face due to her drool, which only increased the arousing sight.

Licking her dry lips, Grayfia looked at the young man in horror. "No~! How can such a good student like you do something like this~? I thought you were better than this, Hyoudou-kun~!" Feeling up to have some fun, Grayfia played the role of a shocked principle who was about to be raped by a student. Issei gave her a deep chuckle before leaning closer to her face with a lustful smirk on his face.

Resting his hand on her soft cheek, Issei gently brushed a stray silver hair that stuck to her lips. "How could I do this, kocho-sensei?" Issei repeated the question before leaning down to her ear, pressing his angrily twitching member to her equally twitching womanhood, being careful not to thrust inside her just yet. "It's because you've been such a naughty principal that I'm like this. I'm going to show you the consequences of dressing and acting like a whore." The dark whisper sent pleasing shivers up and down Grayfia's flushed skin.

"N-No! I-I-I'm not a whore~! Stop this at once, Hyoudou-kun~!" she denied weakly while trying to move away, but she couldn't as Issei had placed his hand firmly on her hips, which kept her in place. "N-No!" she yelled out in fake horror as his lower head entered her pussy. "D-D-Don't stick it in there~~!" Grayfia's plea only fell on deaf ears as he continued to thrust forward.

"Too bad, you fucking whore!" Grunting in exertion, Issei fully buried himself deep within the sexy principal. His eyes slowly widened when the tip of his cock hit the entrance to her womb immediately on the first thrust, surprised with how easily he managed to slide inside her. And yet, he felt that there was also a sense of tightness inside her wet cunt. Had she always been like this? Or was this referring to what she said earlier about needing his help?

The result was instantaneous as Grayfia's head rolled back with her silvers eyes seeing nothing but white. The brunette had slapped his unused hand over her mouth as the muffled moans and gargled shouts of ecstasy coming from Grayfia didn't stop Issei from ramming his cock in and out of her with the same force and intensity as his first one. The sounds of their combined sex slapping against each other just spurred him on and encouraged him, wanting to effectively drive the busty bombshell into an orgasm-induced coma.

It was one of his fantasies, after all.

"Fuck! You look so hot, Grayfia-sensei! I'm starting to get addicted to your slutty body!" Spanking her butt, Issei was still playing his role by removing his hand on her mouth and harshly tweaking Grayfia's nipples. Her pleased squeals urged him to continue his rough treatment while deep dicking, hitting the back of her womb with each pump he delivered.

Grayfia had tears running down her flawless face as she tried to speak, in an attempt to tell how amazing he was making her feel, but she couldn't due to the overwhelming sensation she was feeling. "So… hot… so fucking hot~ I want to keep getting fucked by his cock forever~~! I've never felt anything like this before… I'm a whore for Ise-kun's giant cock~~~!" she thought to herself deliriously, a very erotic expression appearing on her face. The shameful MILF could only stick her tongue out happily while using her experience to squeeze her inner walls around her partner's rod with all the power she could produce.

"Ah, fuck yeah!" Issei roared out happily while grunting rougher than before. The new, tighter hold that Grayfia's wet pussy had on his tool was so amazing he buried his face in her bouncing jugs and sucked on them greedily like a child. Her sweat-covered breasts were delicious and now he focused on sucking on her already-abused left nipple, and a shit-eating grin broke out on his face when he felt liquid spurting out.

"I-Iyau!" Grayfia was finally able to let out a somewhat manageable word when she felt her baby-milk being extracted from her body. She thought she had lost all sense of reality but this was a pleasing surprise that she went with. "Y-Y-You're… you're fucking them, m-my boobs~ so fucking good~~! Right there~!" the MILF shouted out as she felt him sucking even harder on her nipples to comply with her plea. Wanting to hold her son tighter, she showed off her flexibility by moving her hands (tied with her legs) in a weird way and wrapped them around his sweat matted hair that their bodies were in pure physical contact with each other, sending waves of pleasure all throughout their nerves. "Drink me up! I want you to own this slutty principal's body~! Rape me with that big cock of yours even harder~!" Grayfia begged Issei while rutting her bountiful body into his, setting his blood on fire and getting him more determined to fully make Grayfia submit and have her like putty in his hands.

Her back arched almost painfully when Issei started switching his movements from deep to shallow thrusts that hit her entrance glands, a particular spot that she was sensitive in. "Y-Y-Yes! Fuck me right there~~! God, this feels way too good~!" she all but begged the horny man atop her.

Issei was too deep in his arousal and lust for the silver-haired principal to even respond to her pleas. All he could focus on was the amazing feeling of the woman he was connected to at the moment, and how he could possibly make this feel even better for the both of them. He had never had sex before, and experiencing it right now with one who had already lost her virginity made it feel like something he could get addicted to. And he was already becoming addicted to it, feeling nothing but the need to please and make Grayfia his own. Her tight walls were constantly expanding to fit his massive prick, before sucking it right back in. The enormous tits that he was sucking on had a delicious taste and arousing smell that made him go crazy for more, all while Grayfia's dirty words of encouragement and pleas only made him try and fuck her harder just to hear more of her whorish mouth.

As they grinded against each other, everything on the outside world was lost to them by now. All they could hear was the lewdly pleasing slapping sounds of flesh that filled the room. Sweaty flesh clashed against one another in a dance of carnal hunger before Issei picked Kuoh's slutty principal up and continued to bang into her in a standing position.

Grayfia could only hang off her the young brunette's shoulders for dear life with her hands and legs while moaning and screeching like a common street whore. She had gotten even louder than before when Issei started to slap her ass over and over with a brutal amount of force. His heavy hips and the hot spanking that he delivered repeatedly were giving her never-ending climaxes. Grayfis lost count on how many times she came but she knew he hadn't cum once yet. When she would finish one orgasm, Issei would send her into another and another, intense climax after intense climax that made her mind mush.

(Outside of the Principal's Office)

Rossweisse Andersen was walking through the empty halls to the principal's office. She was one of the remaining teachers that remained in school even though classes have ended about an hour ago, as Rose was busy checking a bunch of progress report cards. Now, she was on her way to drop off said report cards in the principal's office so that it would be signed by Grayfia Lucifuge herself before it would all be given out to the designated student owner of each progress report card.

As the woman entered the office she noticed that nobody was present, not even Penemue Sallos, the principal's secretary who could be always seen handling calls and drinking coffee behind her desk that was just outside Grayfia's office.

"Is Grayfia-kocho even here?" she asked aloud before walking towards Grayfia's office. Getting closer to the door, she could hear familiar grunts and moans that were getting louder by the second. Being the horny teenager that she was sometimes, a large blush soon formed on Rose's pale skin, recognizing such sounds even though they were a bit faint due to the door being in the way. "Someone's having sex in there!" Rossweisse thought with her face turning tomato-red in color.

Curiosity getting the better of her, Rossweisse followed the sounds quietly to avoid announcing her presence. With each step, she could hear the moans become louder as well as some dirty talk along the way. She then heard the familiar voice of Grayfia, and the woman was saying such dirty things that it was starting to make the young teacher wet underneath her black skirt. "Holy fuck! I could have sworn that was Grayfia's voice… but who is she hooking up with?" she asked herself. As far as she knew, the silver-haired principal had been sexually inactive ever since Sirzechs passed away.

"I wonder who the mystery guy is… she hasn't been into guys ever since Sirzechs died a few years back, so this guy must be someone she's totally digging for!" With a sly smirk, she decided to take a peek on who was fucking her friend in her office. Although their relationship was clearly not shown in school, Grayfia is quite sociable and enjoys quality time being spent with her teachers and co-workers, so they were actually friends behind the scenes.

Gently opening the door but being careful enough not to make any sound, what she saw in front of her shocked her to the core. In the room was Grayfia Lucifuge, with her legs spread wide and tied to her hands while she was moaning like a real slut asking to be fucked over and over. However, what truly shocked her was the mystery guy who was currently pounding into her.

It was Issei!

It was Issei. Fuckin'. Hyoudou!

"W-Wh-What the hell?! What is this?!" Rossweisse yelled in her head, her eyes as wide as saucers as steam began to be emitted from her ears.

"Yes! Yes~! Punish this naughty principal's dirty cunt! Ravage me even more! Punish this sloppy cunt for enjoying her student's cock~!" Grayfia's dirty words made Rossweisse feel a familiar liquid starting to run down the side of her legs. Unable to keep her curiosity in check, she focused her gaze into the room some more, causing her blush to deepen when she finally took note of how large Issei was. His hips constantly uncovered itself from Grayfia's pussy lips before getting buried back into her with such force that it rocked the desk. With each thrust he made, it looked like he would reach a new depth inside the MILF due to how fast and rough he was banging her.

"S-So hot!" Rossweisse couldn't help but moan out in a whisper at seeing such a sexy scene before her. She was horny as fuck ever since fantasizing about Issei earlier and she couldn't hold in her arousal for the young man any longer. Trailing her hand down her body, she stuck two fingers inside her skirt and panties, then into her twitching lips. "This is so sexy~" she said with a haggard voice, her breathing starting to become erratic.

"Of course!" Issei's gruff and dominating voice made shivers course up through Rose's body. "This slutty cunt is mine to fuck forever! It's already shaped for me and me alone!" he grunted out heavily as the constant tightening of his the woman's pussy was pushing him closer into releasing his orgasm. Sweat dripped down their bodies, and their combined scent drove their heads into a lusty haze.

Grayfia could only nod in response to her young lover, wanting nothing more than to be with, and love a man like Issei forever. She was sure that nothing could ever go wrong when she was around him and now, she couldn't help but worship his cock inside her tight hole. The sexy principal made sure to use her remaining strength on her vaginal walls to wrap around Issei's member in a vice grip. The way that his rod was hitting all her spots made her squeak and thrash around in pleasure. She couldn't even feel her arms and legs anymore and were just hanging lifelessly around his neck, and Issei grinned stupidly at succeeding in making Grayfia feel like putty as he relentlessly pounded into her twat. "Cum inside me, Ise-kun~! I want this wonderful student's dick milk deep inside this naughty principal's pussy~~!" the silver-haired whore begged Issei, who now looked into her eyes with such intensity and lust.

Sliding one arm underneath her, he supported her up by her back and captured her lips with his own, easily dominating over her weak state with his powerful and hot tongue. Kissing wildly, Issei's hands roamed around Grayfia's body from her tits and to her clit, as she was still tied up to respond to any of his actions. Spanking her butt hard, it caused her skin to ripple and finally pushed them to their final stage.

Grayfia was the first to cum; she had climaxed for more than ten times now, and yet her female juices immediately coated his ramming dick in her arousal, and even some of her fluids ran down his legs. This appeared to be her strongest orgasm as Grayfia squealed louder when Issei's prick entered her womb. "YES~!" she yelled out like a whore. His cock-tip repeatedly bashed against her womb and cervix, causing the MILF to have a "fucked stupid" expression on her beautiful face. "CUM RIGHT HERE! CLAIM THIS PRINCIPAL'S PUSSY AS YOUR OWN~! FILL ME UP WITH YOUR MILK NOW!" she half-begged and half-commanded, and she was instantly rewarded with Issei's mushroom head twitching as it exploded his large load deep within her waiting womb.

"S-S-SENSEI!" Issei roared out, his body falling on top of Grayfia as he climaxed inside her dirty pussy. Her cunt walls had milked him for all he was worth and he could only spasm erratically while holding onto her sweaty body. "Wow! Y-Your womb is holding me so tight! It's like… it doesn't want to let go of me…" Issei groaned out weakly, his voice now hoarse as he continued thrusting his hips every few seconds, making sure to fill her up completely with his hot seed.

"Oh yes~" Grayfia cooed out, petting his head with the utmost love and affection. "Keep cumming inside. Keep filling me up with your milk. I love it. I love being your whore. I'm yours forever, Ise-kun~" Grayfia's lovely voice eased his hot body. If possible, the young man would stay inside this place forever and keep on going.

With a whisper, he gently licked the principal's neck before smiling. "I've always looked up to you and admired you from a distance, and I actually can't believe you'd be interested in someone like me. I may not be Sirzechs Gremory, but I know that I can love you as much as he did, I promise. Or maybe even more than that…" he then planted a sweet kiss towards her cheek. "I love that this body is mine alone, Fia-chan. You're mine to fuck for the rest of our lives." Issei's possessive tone gave Grayfia a sense of happiness as she began to tear up. He knew about Sirzechs being her former husband and hearing him make that promise to her sent her heart fluttering like butterflies.

Her hands and legs now untied by Issei, Grayfia pulled her lover down and kissed him gently as her legs were left hanging on the edge of the desk. The both of them were conveying all the love that they had for each other in that one kiss.

Their attention being focused into the gentle kiss, they didn't even hear the door softly close. Outside, Rose was licking her fingers that were coated in her arousal. Moaning against her fingers, she was flush with lust at what she had just came to three times. Her shirt and bra were discarded, leaving her large breasts exposed as she leaned on the doorway. "Wh-What a bunch of perverts… I-I never expected Ise-kun to be so… dominating in sex… is he even the same student that everyone knows?" Rossweisse whispered out heavily, the large blush still evident on her face. "Those two… fucking like animals like that. I'm actually jealous." the young teacher admitted to herself with a pout.

Being a single woman with no experience in having a real boyfriend, Rose wanted what her friend Grayfia had. She realized just now that she wanted the pleasure that she was sure only Issei could give. Not only that, she wanted to experience love as well, but not just with any man. She already had the perfect man for her in mind, yet she lacked the drive to go for it and make it happen.

Having licked her fingers clean of her juices, she put her shirt and bra back on, covering her saliva-covered jugs, before making her way out of the office and school all the way towards her silver Nissan. As she drove towards her apartment home inside her cheap car, Rossweisse still couldn't get act of indecency between her friend and the boy of her dreams out of her mind.

Next chapter, everyone's favorite Valkyrie gets the fucking of a lifetime, with some of the future harem members getting introduced.

Harem so far (No particular order): Rias, Akeno, Asia, Xenovia, Irina, Koneko, Grayfia, Rossweisse, Ravel, Kuroka, Murayama, Katase, Kiryuu, Sona, Serafall, Tsubaki, Tsubasa, Tomoe, Reya, Kiyome Abe, Yasaka, Gabriel, Penemue, Raynare, Kalawarner, Mittelt, Le Fay, Kuisha, Coriana, Venelana, Shuri, Yubelluna, Xuelan, Karlamine, Jeanne, Sakuya, Mio, Yuki, Chisato, Leone, Chelsea, Mirajane, Ultear, Sayla, Himari, Kurumi

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Goodbye… and good night! BANG! *too sweet gesture*

-Lance