School

The route to school was apparently a short one, with it being 10 minutes at most before Rias pulled up in front of a truly huge building. It was clearly a private school, with pristine buildings and an almost idyllic campus. In addition, all the students (except Y/N) were wearing uniforms, making him feel somewhat out of place.

"Here you go, little brother; off to school." Rias informed him with a small smile.

"Goodbye, Y/N." Managing to make something as simple as that sound sexy, Akeno contorted around from the backseat to kiss her brother on the lips. As they broke the kiss, she looked pleased with herself. "I love you."

'Just like her mother...'

As Y/N shook off whatever reservations he had, he heard Rias clear her throat. "What is it, sis?"

"Let me get one too..." Rias blushed, almost as if she regretted asking.

Y/N returned the blush before responding "Oh, you want it too? Okay..."

The kiss with Rias was more chaste than either he'd experienced that morning, but that was okay by him; he was kissing Rias Gremory!

"I love you."

"Love you too, sis. I'll see you later."

Finally exiting the car, Y/N realized he didn't know anything about this place, and if his mother were to be believed, he was almost late.

'Ok, BFF, brief me. How do I get to my next class, and what do I need to know?'

'Class schedule...Got it right here.' Said document appeared in Y/N's head, as if he'd memorized it.

'Good, that's not too far from here. What else?'

'What else? What do you mean, what else?'

'I mean, how is this world different from my own? I mean, if anime characters are just walking around naked, this world must have a lot of different rules that I'm clueless about.'

'Oh, yeah, it does have a few of those. I'm working on synching the relevant info from the you that had this body to start, but there's a lot to sort through. Give me a few days and I'll have you walking around like a local.'

'A few days!? How am I supposed to manage 'til then? What if I accidentally break some ancient rule and get executed?!'

'There's none of those rules; geez, calm down. Just keep your interactions as simple as possible, you already know everything you need to know to not look like an idiot.'

'If you're sure...' Y/N exited his mind and walked toward math class, arriving just before the bell.

"Alright, everyone, let's get started."

'Yoko Littner? Wow...' Y/N marveled at the redhead, knowing what she looked like under her respectable dress. 'Do not get a boner in class!'

As Y/N collected himself, staving off arousal, a crackle overhead signaled an announcement on the PA system.

"Y/N Gremory to the Headmistress's office."

"Ooooh." It seems even high school seniors weren't immune to juvenile taunts. As Y/N stood up, he looked to his sides as he reached the front of the room, noticing something...odd.

'Why are there so many girls?'

Indeed, it would seem Y/N was the only male in this class, but it was quite a large room dedicated to many students. Surely he's just overthinking.

He exited the room, letting his local thoughts guide him to the Headmistress's office. He opened the appropriate door, preparing to sit down before a voice stopped him.

"No need, Y/N, she's ready for you."

'Is that...Midnight?' Y/N stared at her, the woman being an object of his fantasies in his home world. Her suit was tight, emphasizing her best assets, and it was almost impossible for him to break his gaze from her as she smiled and he walked into the headmistress's office proper.

"Ah, Mr. Gremory. You got here quicker than I expected. Sit."

He did just that as the headmistress turned around, revealing yet another beautiful woman.

'Glynda Goodwitch!? Oh, crap, whatever I did wrong, I'm screwed! She's so scary that a school full of junior warriors with supernatural powers is terrified of her...!'

As if to tell him not to worry, the blonde actually produced a small smile. "Do you know why I called you here?"

"I was almost late this morning, but I did make it before the first bell..."

With a small chuckle, Glynda continued "I don't care about that. I wanted to congratulate you on turning 18 yesterday."

"Oh, thank you." Y/N didn't know what this meeting was about anymore, but his worry had faded at Glynda's unusually happy demeanor.

"You know, when your mothers came to me about enrolling you in Sakura Academy, I was ****. You didn't seem too exceptional in any field, even with your previous test results, and then there was your family's unusual lifestyle, but Venelana and Shuri can be very...persuasive." At the last word, a faint dust of red spread across Glynda's cheeks. "I'm happy to say I was wrong. You're a great student with glowing reviews from your teachers and have had no discipline problems for your entire tenure here. And so, I will reward you."

Y/N wondered what she meant before she stood up and began stripping out of her clothes.

'WHA?' Y/N was frozen in this state of mind, unable to say anything as Ms. Goodwitch stood naked before him.

She walked around to his side of the desk, craning down to his ear and whispering "I'm sure I don't have to explain to you what happens next?"

Frozen at the nude blonde, he couldn't restrain an erection hardening at the sight.

"Wonderful. Nemuri, it's time!" Glynda called outside to her underling before she burst through the door as soon as summoned.

"Finally! I've wanted to jump him for ages~" The assistant crowed, strutting naked into the office. They each took their place on opposite sides of their Man, ready for their activities.

"May I start slow?" Glynda asked, uncharacteristically nervous as she tucked a strand of blonde hair back between her ears.

"Yeah..." Y/N was barely able to pronounce words at the moment, unable to believe this was actually happening.

Glynda turned his sitting face toward hers, engaging him in a make out session with the busty headmistress. Midnight had other ideas.

"Screw that; I've been waiting forever!" Nemuri dove straight down to his bare penis, marveling at the erect length as she took it in her hand.

"So big..." The woman took the organ into her mouth, forcing it down her throat inch by inch, swirling her tongue and moaning throughout to give pleasure to the Man.

As he made out with Glynda, Y/N found his hands drifting to her large bust, squeezing her boobs and making her moan into the kiss.

After a few minutes of this, Y/N felt himself ready to cum. He pulled Glynda into him, bracing her with a hand on her back, nearly pulling her over the arm of his chair. His other hand went to Nemuri, caressing through her hair and encouraging her to swallow. Despite this being his first time, these movements came naturally to Y/N.

With his orgasm done, Midnight popped her mouth off his dick with a smile. "Someone's been eating their pineapple~ Are you ready yet, Glyndie?"

"I believe so." Glynda was still nervous as she turned to Y/N. "Please go easy on me. I'm a virgin..."

"So am I." Y/N wasn't much better, but post nut-clarity did wonders for the Man's mental state.

Glynda placed herself between his legs, sitting in lap before maneuvering so that he could fuck her properly. She slowly lowered herself onto him until he felt her hymen.

"It's going to hurt."

"I know. I'm ready."

With her permission, he pushed through, taking the teacher's virginity. The pain quickly gave way to pleasure as he thrust into her tight pussy. After finding their rhythm, they continued on copulating as they moaned in pleasure.

Midnight, not one to be left out, went beside Glynda and said "Left or right, Glyndie?"

"...Right..." Glynda said, breathless.

At that, Midnight positioned herself at Y/N's left side before whispering erotically. "When you go back to class, they'll know what you were doing."

Before Y/N could question her, Midnight buried her face into his neck, kissing and sucking, her intention clear.

"Ah...I suppose I'll join you..." Glynda moaned as she craned her neck to Y/N's right, taking the other side of his neck. She began sucking as her assistant did, only her head was **** to move in time with her movements with Y/N.

With his size and her tightness, it was easy for Y/N to bring Glynda to orgasm, doing so before he came again. Praising his seemingly inhuman stamina, he and Glynda kept going until he finally came, with Glynda being a happy, satisfied mess.

"Oh, Glyndie, you had fun~" Midnight took her boss's hand, helping off Y/N's cock as seed spilled out of her. She returned Glynda to her original seat where Glynda slumped over onto her desk, tired.

Midnight turned to the student in the room with a horny smirk. "Stand up, stud. It's about time you got out of that chair."

Y/N did as asked, his cock still hard, though wet from his previous engagement.

As he did, Nemuri spread herself onto Glynda's desk, her back nearly touching her boss's face as she spread her legs. "I've always wanted to do it on her desk; bonus points for her being here while we do. After what you did to her, she might not even remember this in the morning."

Y/N placed his hands on Midnight's shoulders before plunging into her pussy. He didn't expect her to have a hymen, but she did, at least until he thrust all the way into her.

"Ooh, yes...I love to see a Man taking charge!" Midnight took the pain and pleasure equally well, cumming on the spot. Her arms wrapped around him, nails digging into his back, telling him not to leave or pull out of her.

Y/N was taken in by Midnight's advances, moving much faster than he had with Glynda. He mashed his face into hers, claiming her lips in a frantic kiss. He then moved one of his hands off her shoulders to her breasts, squeezing the melons and making her moan and squeal when he paid special attention to the perky nipple.

Y/N and Nemuri continued their savage rhythm, their bodies bouncing and clapping, caring only for pleasure as they rutted. As with Glynda, it was surprisingly easy to make the virgin Midnight cum, as she did so multiple times before Y/N.

"I'm cumming!" Y/N finally shouted.

"Me too!" As Y/N finally came, the two stopped moving, feeling the white sludge flow from him into his lover. When this finished, Midnight smiled.

"This was great. Hit me up any time, stud~" The woman relished the new feeling within her as she put her clothes back on to resume her proper job. Meanwhile, Y/N was left with the best case of PNC ever after losing his virginity in a threesome with two beautiful women. Though this new insight led him to question some things.

'I thought good sex was supposed to be exhausting, but I'm not even tired.'

'Well, of course you're not. The world would be in trouble if you crapped out after two.' BFF snarked in his mind.

'Haha...Wait a minute, I didn't use a condom! What if I just knocked up my teachers?!'

'Oh, trust me, it'll all be taken care of.'

'If you say so. Do you have anything else about the school I should know?'

'Just the school? Sure, I can scare something up...Ah, here it is! Sakura Academy, one of the most prestigious all-girls schools in the world.'

'You mean before they went co-ed and let me in, right?'

'No, they're not co-ed. You're the only Man in the school, and you were labeled a special case, meaning that Glynda has no intention of letting another Man in.'

'Wait...You're telling me this huge, fancy, private school is full of girls?! How'd I get in!?'

'You're a special case. As Glynda said, your mothers can be very persuasive.'

'I'm the only boy in a school of girls...' At that revelation, Y/N actually fainted, overwhelmed by the new info and realizations.