My Best Bro Got Me Acting Unwise (High School DxD/FGO - Astolfo SI Chapter 1)

"Hey, Issei, let's get married when we grow up." Said one of Issei's best friend.

"Astolfo, what are you talking about?" The six years old Issei looked at his girl bro confused.

"Being married is just being roommates with your best friend forever. So why not?" The pink haired shrugged his small shoulder.

"Oh! ...Okay, then. Cool." Issei smiled and nodded.

"T-T-Then I will also marry Issei when I grow up!" Cried out Irina, Issei's other best friend bro.

"Yeah, why not?" Issei agreed.

"I dunno." Astolfo said with a mischievous glint in his eyes. "Two guys getting married? Sounds gay."

"GAKH!?" Irina sputtered as she looked on with absolute shock. "WHA!?"

She couldn't believe the bullshit of her other friend was saying with a straight face.

"Hmm, yeah, Astolfo is right, Irina." Issei said in deep thought, which bewildered Irina even more that he was buying this. "Two guys getting married would look weird, but if we get secretly married, then it can all work out since we'd be roommates in the end." He grinned and nodded at his impeccable knowledge.

"A-A secretly marriage..." Irina blushed, making Issei worry if his bro has a fever again. "That's like into those romance novels mom has—Wait." Irina froze, before she looked up indignant. "Why am I the secret marriage and Astolfo is the open one?" She shouted in outrage.

"Duh," Issei looked blankly at his friend, and shrugged. "Because Astolfo is a girl, while you're a boy."

And thus a month long campaign of teasing Irina by Astolfo came to an explosive end.

"NO! I! AM! NOT! ASTOLFO IS

A BOY! I AM A GIRL!" Irina shouted.

"Wait, what?" Issei blinked in surprise.

"HAHAHAHAHAHAHAHAHA!" The pink prankster proceeded to laugh his ass off.


That was eleven years ago, and since then a lot of thing have changed for Hyoudou Issei's life.

For one, his bro Irina became his girl bro, his girl bro Astolfo became his bro, and it turns out magic is fucking real.

"Hey, Issei, check it out!"

"WHAT THE FUCK IS THAT?"

"Clucky grew so big I can ride him now!"

"That's that chicken we found!?"

"Turns out it wasn't a chicken. Who knew!"

"BEP-PEROOOO!"

"You did! I don't know how or why, but somehow you did!"

"EHAHAHAHAHA!"

Yeah, that's right, and then to make things even crazier, Irina was apparently training to be some kind of Christian Knight called an Exorcist.

At least that explained why Irina's family had that cool sword hanging in their house, when he used to come over. They are still in talks till now, and Irina visits in the summer when she can get away from her training.

Regardless all that's in the past. Issei doesn't need to get into one of Astolfo's weird schemes, or run away from weirdos shouting about him having some unearned power that they need to dominate the world, or have a harem. (Yeah, right. If he had that, he'd have gotten a harem by now.)

Right now, he was visiting a newly open cafe that he had his eye on, and just relax and enjoy being pampered by cute maidos.

"Hello~, master. Here's your spicy omelets made with luuuv."

Issei stilled in his seat. He knew that voice. He heard that voice nearly everyday since he was five years old!

Issei slowly turned his neck stiffly, as if his body was concrete.

And he saw...

His bro.

His best bro.

Once again, dressed as a girl. A maid. A cute, cuddly maid—

NOPE! Die sexy trap thoughts! I will not get a boner for my homie again!

"Astolfo... why?" Issei pleaded.

"Some of us need summer jobs." Astolfo grinned.

"Your parents are rich. You don't a summer job." Issei countered, deadpan in his tone and expression.

"Maybe some of us are trying to get some work experience." Astolfo said back.

"And out of all the jobs you could find, you had to choose this one?" Issei said.

"The clothes are cute, right?" Astolfo grinned.

"Yes." Issei said instantly before backtracking. "I mean no. I mean, it's not important!"

"Oh?" Astolfo gave a sly smile tilting his head. "You mean you don't want to see a cute girl in a maid outfit with a mini-skirt, who might bend over, or at any moment in a breeze, the skirt rises up and..." Astolfo said, teasingly holding his skirt between his fingers and slowly lifting them.

"Stop it." Issei lightly slap his homie hand from showing off his juicy thighs and curves.

"Eeyah~!" Astolfo moaned.

And the why boner returns. Issei thought.

As if by fate, another customer entered the shop, and as they did so, the wind blew strongly through the store, and Astolfo's skirt began to flutter and rise up, along with other maids in the shop.

Sadly for Issei, he didn't have time to appreciate that view as his hands quickly moved to stop Astolfo's skirt from showing his underwear. Issei wasn't quickly enough, thus he did get a glimpse before protecting his bro's modesty. Once more, Astolfo was wearing cute panties.

I mean normal panties!

"Kyaa~ holding my hips like that. Dear master, you're holding my hips so strongly." Astolfo said with a flushed face, while smiling.

Indeed Issei's hands did end up on Astolfo's hips.

Sqeeze, sqeeze.

"Eyaa~" Astolfo moaned.

"AH!" And Issei pulled his hands away like they were burned.

"Oh master~, how bold~." Astolfo said, finally putting the food plate down in front of Issei.

"Stop it." Issei said pointedly, pushing down his blush. "Seriously, why are you working here?" He then came closer, holding his hand up to cover his mouth and whispered. "Do they know you're a boy?"

"Oh definitely." Astolfo smiled and nodded. "What can I say, I betted that I can rock the look and I could!"

Issei sighed.

"Okay, sure." He shrugged and went along with this. "But why the summer job?"

This time, Astolfo was the one to lean closer to Issei, cover his mouth with his hand, and whisper something.

"Did you know that the local Catgirl like sweets?"

"There are Catgirls in Kuoh!?" Issei whisper-shouted.


It took weeks of baking and cooking, trials and error, but finally Issei managed to make cookies that had the maid cafe girls approve of.

He went to offer the catgirl he heard so much about sweets.

"So you're the secret admirer Tolfo talked about?" Said the white haired smol catgirl, Toujou Koneko.

"Err, sure?" Issei said, hesitantly. He didn't expect a loli. Not that small breasts were bad, but still, he thought all catgirls were well-endowed.

Did anime lie to me?

"Hmm. Gimme." Koneko extended her hand. Issei blinked and broke out of his wandering thoughts. He nodded, smiled and gave her a paper bag.

Crunch. Crunch. Crunch.

Issei initially felt annoyed at Astolfo tricking him on something like this again, but decided to let it go. Koneko-chan was cute, so it was okay.

"Hmm, I approve." Koneko nodded, but her tone sounded like she was talking about something else. "Okay. I'll take you on as an apprentice."

"Say, what?" Issei asked confused.

"I'll teach you how to fight." She nodded again.

"...Huh?" It sounded like he got thrown into a different anime genre all of a sudden.

Just cop car with the red and blue lights flashing and siren passed by them.

"Freeze! We heard reports of a lolicon going around, luring kids with candies. You're coming with us, sicko!" Shouted one of the officers.

"Right, I need to get back to dealing with that." Koneko said to herself. "You shouldn't start running though. Consider it your first exercise since you need the cardio. It would take too long to explain if they caught you."

Issei ran!

He didn't even stop to think about how it was that the cops didn't react to Koneko's cat ears.

Oh, she put them away. Issei noticed as he glanced back, to see one of the officers running after him.

Regardless, there was only one thought running through Issei's head at the moment.

"I don't know how or why, but I know it's your fault you Pink Menace. Damn you, Astolfo!"


Weeks later.

"Hey, Issei, that girl that asked you is a Fallen Angel planning on killing you. She's actually with a group of Fallen and Stray Exorcists holed up in the abandoned church. Wanna make a plan to get laid and have an orgy?" Astolfo barged into Issei's room as he usually did when he visited.

"Yuuma-chan is fucking what!?"


AN: Inspired by this: ...grand-order-au-astolfo-si.29555/#post-9177760

MC is bi this time, and Issei struggles with keeping himself on the straight path.

This is more of a one and done. Not sure if I'll return to it, now that I got it out of my system.