A DREAM OF SUMMER

A Highschool DxD crossover

I

-A pervert's paradise-

"What do you mean you cannot come?" –Complained one Hyoudou Issei on his cellphone, as he stood in the waiting line in front of Kuoh's Harbor –"we have been planning this trip for weeks since we got the prize in the lotto, and this is a Summer Resort we are talking about, SUMMER RESORT! There is going to be even an idol group from what I heard, IDOLS ON SWIMSUITS!"

When one thinks of Summer Season many things come to mind. The sun bathing the ground with its light and warmth, the days of rain that helped when the heat was simply too much, a lack of school and sometimes vacations from wok. But above all, for those blessed with the opportunity (and the money), summer also meant the going to the beach.

And the beach meant swimsuits! And beautiful girls and beautiful older women wearing those swimsuits and showing off the marvels that were their bodies… which meant waists, bottoms and above all BOOBS! For the self-proclaimed Once and Future Harem King, Summer was a great opportunity to indulge himself in the wonderful sight that were beautiful women in swimsuits, the sweat and drops of water covering their skin as they showed just enough for his libido to run wild.

Unfortunately, his parents were not interested in giving him the money he needed since he had never been subtle about his intentions and his grades had been just enough but never quite good enough to be rewarded for his efforts. The absence of an opportunity in the form of a school trip didn't help either, and so the dream for a Summer Island Experience had never really materialized for Hyoudou Issei or his two best friends (currently only friends since his childhood buddy left more than a decade ago) by the time they had developed and fully embraced their libido.

But Lady Luck decided to smile upon him and his friends about three weeks ago, when they had decided to play a street lotto for the sake of it. It was pretty cheap and they had been bored as hell that Saturday, so they thought 'why the hell no?' and accepted the invitation of the lotto vendor. Issei played and won, and boy what a prize he won that day.

Tickets for three people to spend a weekend of the upcoming summer in an island not too far from Kuoh City, covering the expenses for traveling, lodging, and even paying a visit to the amusement park, which would be hosting a concert from a small idol group!

Of course they had double checked, first with the vendor and then with the people in charge of verifying the authenticity of the prizes. Lady Luck had indeed smiled upon Issei and his friends, for they had been given the opportunity to experience a dream of young men all around the world.

And of course, they realized soon after that the main obstacle to this chance would be their parents. But they had beaten the obstacles standing between them and the paradise known as Kuoh Academy, they could beat this new challenge standing between them and the door to this wonderful if ephemeral paradise.

And they did.

Compromises were made, lots opportunities for spying the kendo team or buying new games were missed, all for the sake of improving their grades and saving enough money for the extra expenses, even helping at home day after day to get on the good side of their families. Time and effort sacrificed to gain the right to enter into the Summer Paradise awaiting them, which finally bore fruit some days ago.

They had been beyond ecstatic.

They had gone on a rampage, hugging their parents and then leaving their own homes on their bicycles to meet at the park, all while screaming to those around them about their victory as young men.

Needless to say that had been a weird day even by Kuoh's standards, and even by the standards associated with the infamous Perverted Trio.

Had there not been a risk of serious public outrage and repercussions with the police, Issei and his friends would have thrown their clothes to the ground before using them to make a pyre to honor the Lady Luck for her blessing. They settled for crying manly tears and embracing each other, all the while thinking about what they would do when they were at the island.

But despite their shared enthusiasm, his friends were not present today. At the morning of the fateful day they would depart to their Summer Paradise, Hyoudou Issei stood alone, waiting for his turn to board the ship and demanding an explanation.

"Well, see the thing is…" –Motohama began, pausing a moment as if to prepare himself to say something baffling but true –"remember the challenges we made yesterday between you and us?"

"You mean when you challenged me to ask one of the idols for a date, no matter how embarrassing or how absolute are my chances for failure, and maybe physical pain?" –Issei replied to his friend –"and that I would do that only if you both went and ate The Special of certain restaurant and brought proof that you did it?" –he finished and waited for confirmation.

"Yes that one. You see… we did it. Ugh…" –Issei could see and hear Motohama actually grimacing on the small screen of his celphone, his face looking a bit pale and sweaty –"We went there and asked for The Special, we even have evidence in Matsuda's cellphone, which I'm sure he will send you when he feels better."

Now it was Issei who grimaced in sympathy, since he knew what those words meant.

"Are you two morons?" –Issei exclaimed in bafflement at the confession –"You both know just as I do, just as many other do in school and even at home, that The Special is cursed. People have gotten sick by trying eating that entire thing! I just issued an impossible challenge to counter the impossible one you gave me!"

Motohama only laughed weakly but with genuine enthusiasm.

"And we did it my friend. We faced the challenge head on and did not throw up right afterwards, we finished every speck on our dishes and glasses. And we are now paying the price, just as you must do your part, Issei" –Motohama ended with a more determined voice.

"But I-" –Issei began, but was interrupted by his friend before he began making an excuse.

"Are you a man Issei?"

"I mean yes, but-"

"Are you a man of your word or not, Hyoudou Issei of Kuoh?"

…

"…Of course I am"

"Is that hesitation in your voice, Once and Future Harem King? Are your promises and your dreams just as feeble as your resolution to make the latter true?" –mocked Motohama, clearly baiting him into an outburst.

He was met with success.

"Of course not! I am a man, the manliest of men, and the Once and Future Harem King!" –he exclaimed, startling some of the people besides him and even making someone laugh. But even as he gave an apologetic gesture, his determination remained alight –"I am going to the Summer Paradise even if I have to go alone, and I will get more than a date and a photo with beautiful idol, I will get a lover's kiss! Just wait and see you bastards!"

Motohama smiling face could be seen on Issei's phone –"That's what I wanted to hear, comrade. Through we will not give you any support in your trial, our spirits are always with you. Now go forward and make our dreams come true, take the first step forward to embrace your true destiny, Hyoudou Issei!"

Manly tears were shed from both sides as the call finished, and Issei put his cellphone back into one of his pockets just as the finally reached the end of the line before going aboard.

He had a very good feeling.

Great times awaited him.

His mother showed a surprising amount of concern when she realized he was going alone, even if for a weekend, but she nevertheless helped him become accustomed to the experience of making his first trip solo. It was both embarrassing and heartwarming, awkward yet very helpful.

He spent most of his time on the ship by reading the only manga he managed to smuggle in his backpack, one recommended by Motoyasu and which he finally agreed to lend to Issei in commemoration of their lucky shot at the lotto. The journey to their destination was surprisingly short, only about three hours or so between the harbor on Kuoh and the one on the Summer Island.

Even in this short amount of time, Issei still managed to make an impression when he decided to interrupt his reading time to become familiar with the people on board.

He was able to spot the idol group, standing separate from the crowd and at the furthest part of the deck.

They were all pretty in their own way.

The smallest had blonde hair in short ponytail, blue eyes, and a big smile present on her face. She wore a short sleeved orange shirt with a cat face, and simple blue jean skirt.

At her left, another girl with black eyes and gray-blue short hair, her face focused on something and revealing nothing to him. Her clothes were a sleeveless black shirt with a star motif, the short sweat pants and tennis on her feet showed she most likely enjoyed jogging.

Further left stood the tallest and probably the eldest of the group, her long hair a lighter tone than her fellow blonde, falling down and covering her back but and ending just before her rear. Her golden eyes and expression revealed mischief and curiosity, but also care for her companions. This girl wearing a long strawberry-colored dress and some elegant sandals also happened to be the most stacked of the four idols.

The second place belonged to the final member of their entourage, standing at the right of the first girl, and being only slightly taller than her. She wore a white sleeveless shirt that was covered in gray dots, a fuchsia pair of shorts and a blue purse hanging from one of her shoulders. Her hair matched color with her pants and was arranged in twin tails by a pair of yellow bows, her crimson eyes matching her hair and giving her a unique look that reminded him of the anime of Elfen Lied. And yet, in contrast with the jaded female protagonist of that story, this girl had a smile on her face that reminded him of the more innocent facet of the tragic heroine.

Having taken a look at the group, his will to engage the challenge faltered for a brief moment.

While the four girls could not match the beauty of the Great Onee-samas from Kuoh Academy, they were nevertheless charming in their own way. And for a teen whose experience with the opposite gender outside of his family could be summed in proclaiming himself the Once and Future Harem King and spying on the sports female teams, it was still quite a challenge to approach the any of the girls from the idol group and not fall into his antics.

But they didn't know about his reputation in Kuoh, so he had an opportunity.

He could wait, but he and his friend knew enough of the entertainment industry to understand that an idol's schedule could be leave little in the ways of free time.

The challenge entailed that he tried getting a date with one of the idols, his friends probably did not expect him to succeed at first, or ever. But he was used to making a fool of himself and despite being met with scorn and failure by being an open pervert, he never let that stop him from believing that one day his dream would become true. Regardless of success, this challenge could be the first genuine effort into taking a step forward for his dream.

And so, armed with the stubbornness of the foolish and the determination of a kind pervert, Hyoudou Issei stepped forward to meet the idol group, put his best smile and abandoned all hesitation before directing his attention to one of them and speaking from his heart…

"Hello, I'm 16 years old Hyoudou Issei, first year in Kouh Academy, and I want to invite you on a date!"

"…"

"…"

"…whoa"

"…aren't you the guy that shouted about being the Once and Future Harem King?" –commented the eldest of the group.

Great times had yet to come, but it could have gone worse.

His focus crumbled for a moment after being tagged by his self-proclaimed title, and his efforts to explain resulted in making an even bigger fool of himself. But the pink haired idol gave a small laugh covered by her small hands, which in his opinion make it all worth it.

And after coming down from the ship after they arrived at the harbor, Issei made his mission to try once again, all the while trying to avoid being tagged as a stalker.

Of course he also enjoyed the sights, from the resort mixing with the town to the beautiful beach and its many wonders.

The sea.

The sun.

The people around having fun.

And the many pretty girls and women in swimsuits, including the idol group he met aboard the ship.

And what swimsuits they wore. The girl he tried getting a date with had the tamest of them and they barely covered her breasts, while both blondes could easily appear on an adult magazine.

He was able to meet them once more but had been less "Issei the Charming" and more "Issei of the Pervert Trio", even if his antics had been way more restrained considering he did not want to anger them or worse, their manager.

Unknown to him, he came off less like a pervert and more like a teenager seeing his crush almost nude for the first time, showing open interest but also too much embarrassment to do anything else than fool around.

"Motohama, Motoyasu… this is for you both as well. I promise to you and myself that I will become victorious!"

Unfortunately, there were no more chances after the brief encounter on the beach and the sun from the early afternoon of the Sunday bathed Issei as he pouted to no one about his lack of success.

However, he knew his chances were limited and opted for having a good time without spending all three days of his visit on the island failing to woo a pretty girl, that only lead to depression.

He already knew of his limited chances to encounter the girl and that time was soon to run out before his return home, so he decided to at the very least spend the rest of his last day on the island doing something else than trying to woo a pretty idol. Otherwise, depression was the only thing waiting ahead.

Issei opted to go for a walk around the city for about an hour, and the time spend on his own gave him an unusual insight.

For one, he found himself enjoying the city and even considered visiting the school and the church, even is his main drive still remained the chance encounters with pretty students and nuns.

The food was okay, nothing out of this world but good enough to fell he was spending his money in the right places.

As for his challenge… Issei kind of felt like a dick.

Looking back, he may dream to have a harem but he also wanted genuine feelings involved. Despite his bravado in Kuoh, Hyoudou Issei was a simple person who wanted an honest relationship and would do his best to make happy any girl that gave him the chance. He stumbled and made a fool of himself, but no one would ever be able to tell him he did not put his all into making whoever he cared for happy. But this whole deal with getting a date felt like he was playing with the girl.

Did he find her pretty? Of course he did, even if she was not Rias Gremory or Himejima Akeno. Did he honestly like her? She laughed both times at his antics without mocking him, but he knew even less of her than he did about the two princesses of Kuoh Academy which he had never talked to. Could he meet her again after the Summer Island experience was over? Probably not.

…Then why was he going through the effort of getting a date with a stranger he barely knew and whose beauty caught his attention but did not make him stare like in Kuoh Academy? The whole manly challenge suddenly felt pointless, even repulsive to some degree.

If a beautiful girl were to suddenly approach him and offer a date, or even better, to become his girlfriend, Issei knew he would say yes in delight and plan to impress her to the best of his ability. But if she was merely doing a challenge like him or using him to fool around, would he really want such experience? Would he want for someone else to experience that from him?

Of course not.

Which is why he decided that he would stop this nonsense and pass his time doing something else, and maybe go to the concert at night.

"Yosh, I have decided. No more stupid challenges, no more trying to woo an unknown pretty girl to impress my friends. This Hyoudou Issei is not a pretty boy scumbag and will make his dream come true with pure honesty and his own awesomeness!"

Issei declared out loud, his face the visage of resolution.

A visage which crumbled when he heard the next words.

"Will his Awesomeness be interested in sharing more of his great plans for little old me, then?"

A cold shiver traveled from his neck and all the way to his rear, his skin gained a pale complexion and cold sweat began falling down as Issei turned almost mechanically to the origin of the voice, not daring to use his own.

His light brown eyes met crimson eyes and pink hair on a familiar face spotting an innocent smile.

And despite knowing the girl in front of him showed no malice, Hyoudou Issei still felt dread as he was confronted with the person responsible for his recent epiphany.

He was an honest man, so he honestly spilled the beans.

She listened to all of his words and apologies and merely nodded until he was done.

And then, to all of that she simply had a punishment for "leading her on".

"You sure you want to go to school of all places before your concert?" –he asked her once more just to be sure.

"Are you saying you are not a man of your word, Once and Future Harem King Hyoudou Issei?" –she teased him, she actually teased him, with a smile and a small pout on her face.

'Damn, she is cute'

"No, no, I will do it! If you really want the high school date experience then let this Hyoudou Issei be the man to give it to you. Noting weird, I promise!" –he added the last part to reassure her he was not going to pressure her into anything, to which she giggled.

"Then let us go my one-day boyfriend. I can talk with my manager to get permission to go visit the school, provided I call every so often in the two hours I have to spare."

They both smiled at her comment and prepared to make their way to their chosen location, when a figure passed beside them.

It was a woman wearing nun robes, though they looked less than those of a normal Sister of any church and more like those found in some of his favorite series of manga and games.

Her black hair was covered by a veil, but a couple of bangs fell over her ears and covered both sides of her face, and two long braids could be seen at each side of her voluptuous body. Her milky white skin reminded him of Himejima Akeno, but her crimson eyes were similar to his current companion, if a bit darker.

No words were exchanged, and the woman simply continued on her path, her own concerns remained unknown to Issei and his date.

His attention was brought back by a hand pinching his left cheek.

"Ouch, ouch, please stop!" –he whined in protest.

"Mou, we haven't even begun our date and you are already looking at other women. You truly are an enemy of young maidens, Harem King Issei" –she complained with a pout, but once against there seemed to be no vitriol. Only something else in her eyes, which focused on the ground as soon as he made contact.

The way her sight shifted, and the way she held his cheek as if she was holding a sleeve-

'Ah'

He smiled to her while raising both hands in defeat.

The returning smile was all he needed to confirm his suspicions.

"Well we do have two hours and the school not that far. Let me make a call and then YOU can impress me as we take out time to get there."

Great times ahead, indeed.

A/N: Here it is, the official first chapter. I decided to cut it here and develop more on the next update, which will have the perspective of Issei's date. We will have two more different points of view before the main plot begins, each giving more information to those who pay attention. This chapter in fact already did, and I welcome those who find this project interesting to make a guess in the review section.