AN: this idea came to when reading a bunch of different self-inserts, that were pure pleasure reads, now I wanted to make a self-insert, that had real value, but I couldn't do it. So I decided to partly follow a route of a pleasure read and real plot and character development. Some characters will be OOC, I will try to have all characters stay true to their original self. One character will be drastically different, it will be apparent who it will be, and how they are.

—Line Break—

Prologue

Beep Beep Beep

I woke up to the sound of an alarm clock. It was strange, I have never set an alarm clock before, it was always my mother waking until I moved out and was able to wake up at any time, due to my job.

I moved my hand to the clock hitting it. I was always too much of a strange person, an otaku. I loved anime too much, that I started to read mangas then when another void entered me, I read the light novel. It was always a joyful time when a volume release and then it got animated.

I got up from my bed, groggy. Anime, Manga, Light novels have always been my lifeline, so much, that I moved to Japan, and started to write my own Light Novel. My family members thought of me as the black sheep of the family. I never really cared what they thought, I wanted to follow my dreams. Becoming a famous novel writer.

God, why am I reminiscing about my past, I have never done this. I found my answer in the bathroom. I moved myself to the bathroom, like a routine. Entering it, I flipped on the lights.

Every novel I read, I had no problems with, until I watched and then read Highschool DxD. The character felt two-dimensional, the main character felt as he never deserved the power he got.

Rubbing my eyes, I stared into the mirror. The author most likely wrote as a pleasure read, but I couldn't, I like development. I glanced at my brown spik- huh, brown, my hair was black. I glanced down towards my face, it was that of Issei, a character I hated.

I mused to myself, that this was a dream, and moved to pinch myself when I saw, a burn mark on the my-Issel's right arm. I didn't know what to think of it, so I went to pinch myself.

Ow.

"This is real," I tested out my voice. My voice was foreign, it sounded close to his Japanese voice actor but almost slightly deeper. It was lucky that I spoke Japanese along with English, in my previous life. My previous life, I'm already thinking of that as a past experience. I chuckled.

I smiled, at least I could make this life interesting, Gods, Devils, and Angels. All the things you could find. It should be fun for once, an uncharacteristic grin forced its way onto my face.

"Issei, it's the first day of your second year, you don't want to be late do you," I was brought out of my thoughts by a voice who I presumed to be Issei's mother. The first problem I will encounter is that I have no memories of Issei's life, and I only watched up to the Excalibur Arc, and read the rest, unluckily the author hasn't finish it, so I will be going into uncharted territory.

I quickly began to take a shower, I grabbed one of Kuoh Academy uniforms, putting it on, I ran downstairs. Entering the living room, I found Issei- eh my mother and father eating breakfast. I had to prepare myself to respond to and use Issei's name.

"Morning dear, your food is on the table," Is- my mother spoke. I walked over to the table, where I saw pancakes, and h- my father reading a newspaper. He smiled at me, then spoke "Issei, we are going to have a man to man talk if you don't get a girlfriend by the end of this year,"

I smiled nervously, I was never good around women in general, I always kept to myself. I nodded, I didn't trust myself to speak. From how he spoke, it seems that this was a daily occurrence. I began to eat.

"Thank you for the food,"

"Issei, honey, remember your sister will be visiting us," I almost choked on my food, Issei never had a sister. I continued to eat normal, nodding to my mother.

I finished my food, I automatically walked over to where Issei's bag was. It seems like the routine was engraved in his body.

"I'll see you," I quickly said, as I walked out of the house. Both my mother and father looked at me worryingly. I closed the door, and let my body direct me to the school.

"Fuck, I'm still awkward," I mumbled as I walked, I pondered, maybe this wasn't the same DxD as the original one. There were too many possibilities to go through, but I had to shift into 'strategist' mode.

Step one was to finish this school day without drawing the attention of the devils and any other beings hidden in the school. Step two was determining if I had sacred gear, Boosted Gear. Depending on that it would branch on into two different directions.

I hauled myself, when I heard a scream, I look around for it. I spotted the source, it was three men and a schoolgirl, the girl being Akeno Himejima. I looked away, pretending not to hear anything, and kept walking, as I walked away, I turned back catching her glaze, she looked disappointed.

What, should I help her, what could I, a human do to help a devil-fallen angel. Anyways I never cared for any of the characters of this world. I never cared for others, they were always too caring.

From behind me, I heard who sounded like one of the men scream, "You bitch, what did you do to my men," I kept walking, not caring. Screams filled my ears, I ignored it and kept moving.

I stopped in my tracks when I remember that this Issei had a sister, so they most likely went to the same school, I began to speed up my walking. This was another obstacle to come across, one I had no idea how to deal with.

I spotted the school gates, with the student council president, Sona Shitori. I moved into the schoolyard paying no mind to her, she did the same to me.

Peering through the classroom door, I saw an empty seat in the back of the room. Walking towards it, sitting down.

"Class, settle down, " the teacher walked in, slamming a binder down on his desk. I pulled out a notebook and began to follow the teacher.

—Line Break—

I closed my notebook, I picked up my bags and headed for the cafeteria. When leaving, I spotted a young girl with black and red hair, standing with a girl the same age as me, she had long blonde hair with a sizeable chest.

My eyes widened when I spotted two more familiar characters. They weren't from Highschool DxD but RWBY, why were they here on Earth and not Remnant. I cut my gaze from them when I got caught by Blake. I blushed and moved away, they were more beautiful in real life than in the animations.

I moved myself to a seat, near the door and wall, positioning myself opposite of the window. I glanced over my class, before class started, I spotted the two friends of Issei, it seemed they weren't friend of hi- me. Another head I spotted was Yuuto Kiba, or at least a female version of him.

I let out a sigh, I hoped that this wasn't going in direction I thought, the harem route. I liked the harem route if the characters were built enough for it, but most times they were forced, why date someone who looks like they are forced, why date multiple people like that. Unless you were a sick bastard who liked that.

I shook my head, as the teacher walked in, and the realization set in, I would have to retake school. My face formed into a frown, inside I began to stress, In my previous life I barely passed school, with C and B.

I quickly moved into the cafeteria, grabbing my food, then moving outside to a shaded area. My face was composed, while my mind overclocked, why were characters from RWBY here? If Issei had a sister, where was she? Is Rias watching me?

I snapped out of my thoughts by the whispers of my classmates. "Come on, Its the Grimm Squad, they transferred in," A male student who I didn't recognize, ran pass.

"The Crimson Princess, The Ice Princess, The Red and White Dragon Empress, and now the Grimm Squad, I've got to move out of this town." Another male student sigh, following alongside the other.

My eyes widened, the supernatural was well known in the world. Was this isolated, to this town. Questions began to rapidly fight through my head, my fear steadily increases, but my fears were put down by another male student.

"You're following those stupid nicknames, how were they even named that fast,"

Oh, it's just a nickname they came up with. But that's doesn't answer how they were here. There wasn't enough information for me to make a assumption. Maybe there was no explaination for them being here. I quickly put those thoughts on the back burner, as the bells were about to ring.

As I walk to my next class, I began to process the information that those three spoke of. The Wielders of Albion and Ddraig were females, that went to this school. I really didn't like where this was going. Hopefully I'm not even the main character, maybe the new Red Dragon Empress was the main character.

Being a main character was a difficult job, depending on the story, it could be hell or it could be easy, in this world it will be hell. I rather be a side character. Moving through the hallway, I bumped into a silver haired girl, "Sorry about that," I spoke, backing up, I took a look at her. She was beautiful, like a model, she had a neutral face, a frown was display on her delicate face.

"My name is Issei Hyoudou," I greeted her, as soon I spoke my last name, her face went from her previous frown to a neutral face. "So, you are her brother," her tone was low, aggressive, and demanding. It clicked, she was the White Dragon Empress, Vali Lucifer, her new name was unknown. I would have tread carefully, she was a dragon.

"I'm sorry, may I ask who you are speaking about," I politely asked, her face moved to a smirk. "A perfect opportunity to destroy her," her low voice, reached me, my face was neutral.

"My name is Livan Lucian," she politely greeted, her tone had a drastic change, she had an alternate motive with me. But her last name was ironic, Lucian was a man who constantly ridiculed people who believed in the paranormal or religion. In this world he was an idiot, but in my previous world, he might of been right.

"Pleasure to meet, but I must be getting to class," my voice turned formal, before I got that register I walked off to class. Turning my head back, there was a small smile on her face, she said something that too quick to hear. I began to run to my class.

—Line Break—

A man was laying down on a couch, a television in front of it, perfectly positioned to watch from his angle. The visual playing on the television was a young man named Issei Hyoudou. The television was playing the man's thoughts and his surroundings. The man watching him was an old man, he had wrinkles, he was dressed as a gentleman, and his eyes were glowing a blazing red.

The man was Zelretch the Wizard Marshall, the wielder of the second magic, and the troll of the multiverse.

His newest source of entertainment was quite dull, while he enjoy these types sometimes, he wanted something different, he was bored with all these hero types, he wanted a villain. Not a villain of mass destruction but one who would achieve his goal at any cost. That was why pick him, a man filled with determination to grab his dream, his only problem was that he had good morals.

The magician grinned, an idea popping into his head, he needed a heroic spirit that was corrupted with enough power to survive in that world. While the avenger class came into his head, Angra Mainyu was a good candidate he didn't have enough power to survive.

An alter, which one would work? Zelretch's grin widened, Gilgamesh, while he may not be alter in the main timelines, one of other many could work. The television began to rapidly change to different forms of Gilgamesh, it zoomed pass regular versions of Gilgamesh. It stopped on a pale blonde hair wearing pitch black armor. His eyes were a blazing crimson. He was perfect.

—Line Break—

I packed up his items, and as the bell rang, I walked out, heading home. I walked out of the school, I saw a card from the sky, from my glance, the card looked regal but it felt corrupted by viewing it. I do not how it felt like it was corrupted, but I felt it was calling me. Against my better judgement I walked over to its drop location. I bent down to pick it up, as soon I touched it, it vanished. I felt pain shoot through the arm that touch it. I grasped it, and began to run home.

I glanced down to my arm it was slowly becoming pure black, covering it up. I felt my body trying to reject whatever this was when suddenly.

"So you will be my host, child," a voice spoke, it was regal and apathetic.

My eyes widened in fear, as I kept on running. I recognize the voice, it was Gilgamesh, but his voice was different. I was about reach the door of my house, as heard his voice.

"Allow the merging process through, rejecting will make it worse,"

As I touched the door, my vision faded.

—Line Break—

AN: Sorry about the cliffhanger, but if I continued on it would interfere with part of the flow. Now what is this mess. Well, this is what happens when someone reads too many fate and SI stories.

The 'Is- my' that you see in this, will be the protagonist trying to fit into a person he is not and using their name, he will struggle with this for the first couple months.

As for the RWBY characters in this, they are here for a later arc, but they will appear in each chapter, slowly progressing the Protagonist's confusion.

The OOC I was speaking about was Zelretch, in canon, he is not an entertainment seeker or an evil person. The reason why I formed him into this character is to steer the protagonist on to his 'route' and for another reason that will be shown at a later date.

For Gilgamesh, I picked out an idea I saw online, a fanart for a Gilgamesh Alter. While he seems to be altered in the original world of Fate. This Gilgamesh will be consumed with hatred of people who are content with their life, gods who waste their immortality.

Class: Archer (Alter)

Alignment: Chaotic Evil

Stats

Strength: A

Endurance: B

Agility: B

Mana: A

Luck: C-

Noble Phantasm: EX

Skills:

Divine Immortality (A): Gilgamesh relentlessly pursued Immortality, after gaining it he ended the age of gods, by destroying each pantheon. This gives him a buff to each stat expect Luck, decreasing it by one.

————

Now the stats are different from regular Gilgamesh by his new skills which overtakes Divinity. Divine Immortality has more backstory to it that will be revealed later. He has more skills that will be later discovered.

His Noble Phantasm will still be Gates of Babylon, but it will be corrupted, in some ways, it will be good or it will be bad.

Thanks for reading, please leave a review.