Disclaimer: I do not own High School DxD


Droplets from the sky splattered across the smooth surface of the glass pane. Raindrops trailing down the outside pane, battering the window with a rhythmic beat, reverberating across the glass surface outside. The pittering and pattering of the rain echoed throughout the castle walls.

Scooting closer to the ledge of the tall arched window, a small brown-haired boy pressed his forehead against the chilled glass pane. Tears streamed down the boy's face, landing gently across the inside of the window, trailing alongside the raindrops.

The small boy quickly wiped the weariness from his eyes, refusing to let another tear fall. His eyes, sore and tired. He couldn't be weak. He'd promised to be strong, for her.

Looking down from out the window, the little boy looked onto the front of the castle, as luggage was loaded off of a limo and brought into the castle door.

His breath hitched at the sight. The finality of it all, nothing could ever be done to change it. The boy's heart ached painfully, he missed her so much already. No more of her good night kisses. He could no longer embrace her. The embrace that had shielded him. The warmth in his heart long extinguished, left only numbness that ran through his body. The boy closed his eyes shut.

"There's no time left for me, Issei. Live your best, for me, my Little Dragon Prince"

Misery ebbed away at his heart, threatening to consume it. He clasped harder onto the pouch he was holding in his hands as if it were to disappear. A simple clothed pouch, the only thing that he was allowed to keep. The last thing from her. The simple pouch was light itself but felt as if it held his whole world.

He clenched the pouch closer. His knuckles turning white.

Easing his grip, the boy softly held, cherishing the last of his mother's memory. The ache in his chest never seemed to go away. He begged for a miracle. Prayed to any higher power, even to the Holy Creator himself no matter how much it hurt the young devil, to bring his mother back. To wake up from this horrible nightmare in the embrace of his mother. He would give anything to feel her warmth again.

"Is-Issei?" came a tentative voice of a young girl.

Issei's weary eyes turned to look up behind his shoulders, following the timid voice to the doorway of the room. Aquamarine eyes were cautiously peered at him from behind the side of the doorway. Long beautiful crimson locks as red as blood itself ran across her back down to her knees. She was adorned in a simple white silk nightgown, holding a brown teddy bear.

"I-is it alright if I come in?" She yet again asked in a timid voice.

Issei nodded slightly. All his strength was long gone.

She quietly padded into the room, taking careful steps until she took a seat on the ledge next to the curled-up young boy. Issei slowly looked up to the sight of his best friend, her crimson hair was even shone brighter in the moonlight. She positioned herself closer to him. Reaching out, she hesitantly clasped her hand over his, gently caressing his knuckles.

"Onii-sama says you're going to move in with us now," the redhead said quietly, barely whispering.

He merely nodded again.

She continued, "That means w-we can have as many playdates we want, every day can be a playdate…. right, Issei?"

He knew what she was doing, trying to distract him from the gaping holes in his chest. He nodded, though playdates couldn't have been further from his mind though.

He continued to blankly stare out the window. The opaque rain clouds slowly drifting across the purple night sky.

Together, the two young children sat in oppressive silence for what felt like an eternity. The sound of the rain hammering against the roof droning on. He heard a sniffle come from next to him.

He finally turned away from the window to find a teddy bear held out to him, "Maybe Stella can help you? She's always been there for me."

He looked to meet her eyes. Her aquamarine orbs on the verge of tears, wet pools lining the edge of her eyes. even her light-hearted question didn't truly reach her eyes.

The sight of his dear friend near tears instantly crumbled his resolve, Instead of taking Stella, he latched onto her like a lifeline. His arms tightly wrapped around her. He shook uncontrollably as she embraced his head, dampening her soft silked shoulder. Her warmth chasing away the void that threatened to consume his heart. She gently stroked his hair, holding him closer to her chest.

"Ria-nee, please never leave. Please don't leave me." he croaked out hoarsely.

"It'll be ok Ise, I'm here," Rias gently whispered, her own tears landing gently on his shoulder.

"I'll always be there, for you."


Author's Note: Hello, thank you for taking the time to read. I've recently taken an interest in writing so this is one of my very first fics. I'm hoping to improve through real criticisms, whether it's about my grammar, sentence structure, and even the narrative plot, I would greatly appreciate it.

With this fic, I'm hoping to create a more compelling version of Issei. I'm not claiming to improve the character but think of it as adding more layers to an already great character. He'll definitely be OOC and he'll have different motivations and goals, but at the end of the day he'll still have his core characteristics such as his honest heart and perversion(although a lot more toned down).

I also wanted to explore more of the political side of the Devil aristocracy and the delicate cold war-esque peace between the three factions at the beginning of the series.

I can't say that this fic is one hundred percent original because many of its aspects are heavily inspired by other fics such as Belial the Liar's Dance with the Devil and Noferatu869's Duality of Man, both of whom are my favorite authors in this community.

Anyways, thanks again for reading.