Please note that this fanfic is written based on when Rias already graduated high school (19 y/o) and married Issei (18 y/o).
***
Issei couldn't help but smile at the familiar sight of Kuoh Academy as he turned the corner.
His latest mission of hunting and destroying a fallen angel for the Gremory family had taken longer than expected. The tricky bastard had proven to be quite the adept sneak and had managed to get away several times before his untimely demise.
It's been nearly two weeks now since Rias had sent him off on his latest task. His phone had been destroyed during the chase and Issei was looking forward to hearing his cute fiance's voice again, even if she spent the first five minutes scowling as she berated him for carelessness. She was so cute when she was pouting, he didn't mind her nagging him.
The school grounds were lively as students trailed in for the day. Issei's eyes wandered happily among the female students, admiring how great they looked in their uniforms. A few girls with bouncy bosoms had their top buttons undone and he fully appreciated the ability to check out their cleavage before watching their swaying asses sashay away in their short magenta skirts. God, he loved the uniforms here. The button down corsets the girls wore only further accentuated their curvaceous figures. It was good to be back.
His thoughts drifted back to his fiery haired fiance. Known as the Crimson Haired Ruin Princess or the Princess of Destruction, Issei had never dared to imagine that their relationship would become what it is now. Then again, a lot had changed since she'd come into his life - literally reviving him into the demon he was today. He still remembered the first time he'd seen her, how her flawless beauty had taken his breath away. Still remembered how her words had been the last he'd heard upon dying, and the first to welcome him back as she revived him. He still couldn't quite believe how incredibly lucky he was that she wanted to be with him.
He looked down to check that his own uniform was in order. Black blazer, check. White, long sleeved dress shirt, check and unbuttoned. Rebellious red t-shirt underneath, check. Black dress pants, check. Issei paused as he took in his worn blue and white sneakers. They were getting pretty scuffed and dirty from all his recent missions. There was no way he was ever going to bother with the school's brown dress shoes, but maybe it was time to get himself a new pair of sneakers.
As the familiar building loomed ever larger with each step towards it, rather than entering the main school building and following the flow of bodies, Issei veered off to the side. Leaving behind the early morning chatter as students streamed into the building to find their classrooms, Issei admired the school grounds from a very different perspective as trees enveloped him.
Kuoh Academy had always given him the impression of a grand mansion. Even for a private school, it was ridiculously grandiose. Though now that he knew the true purpose of the school and was a part of its inner workings, Issei had long stopped being surprised by the lengths the Gremory family would go to keep themselves comfortably accommodated.
The clock tower of the old schoolhouse poked up out of the treeline ahead. The quaint little three story building was charmingly picturesque, painted white with a dark grey slate roof and vibrant green vines creeping up its side to the second floor. Originally the schoolhouse years and years ago, the abandoned dormitory was now the fabulously renovated base for the Occult Research Club created by Rias.
As he neared the building, memories of his most recent intimate moments with Rias at the clubhouse had his heart beating a little faster. He still wondered if he could've done it differently, said it better somehow when he'd confessed his feelings to her. He could still see her expression, her blue green eyes filled with joyful tears, when he'd addressed her as Rias for the first time as he told her he loved her.
Stepping out of the treeline, the clubhouse stood quietly before him and he took a moment to admire it. So many memorable events had occurred within those four walls...the first time Rias had let him rest his head on her lap, the first time she'd let him use her breasts as pillows, all the times he'd been distracted by her hourglass figure during their meetings...he was getting a bit hard just remembering. Maybe today...maybe...he gulped, wondering if today would be the day when he managed to finally work up his nerve and...
"Oh god," he spoke aloud to himself, suddenly flustered as his imagination ran away. "C'mon Issei, get it together! She's your fiance now. We haven't seen each other in two weeks! I'm coming back with good news and today...today is the day that I'm finally, finally going to get in Rias Gremory's delicious wet panties and take. Her. Virginity!"
His rousing speech was met with birds chirping happily among the tree branches. He looked around, embarrassed, and was glad that no one seemed to have been around to witness his sad little pep talk to himself. Despite being engaged, the furthest Issei had gotten with Rias so far was a lot less exciting than what his jealous peers assumed. Despite his life goal of becoming a harem king (now with the addendum of also becoming a demon lord) he was still a virgin...though Rias' habit of insisting on sleeping naked with him has tested his willpower on several occasions.
Stepping through the front door of the club house, Issei called out to no one in particular. "Anyone here? I'm ba~ack! Tadaima!" It was surprisingly quiet. Part of him felt a bit disappointed. The group could be a bit rowdy at times, sure. And yeah, they always seemed to intrude on his personal space at the most inopportune times. But it was nice to be a part of such a close-knit group of friends. Plus, after two weeks off on his own, he kind of missed their company.
Even though Rias had already graduated, she was often still found visiting the clubhouse. Issei was certain that he'd find his fiance here, but on the off chance that she wasn't...well, he could definitely use a hot bath. Eyeing the plush furniture, he decided he could also maybe have a nap. After days of camping in the wilderness, Issei felt a newfound appreciation for the luxuries of modern living. He let his fingers trace across the wood paneled walls, linger over the soft velvet of the Victorian style couches and chairs as he made his way upstairs.
He decided to stop by the President's office first. Asia was the current club president, but in truth, Rias still frequented the place often enough that Asia only held the title on paper. Seeing how quiet the house was, he wasn't actually expecting to find anyone. So it was with surprise that he did find someone in the President's office when he casually opened the door without knocking.
"Rias, you in here? I'm ba~ack! Eh?" He stopped short in the doorway, startled by the sight of an unfamiliar person sitting behind the President's desk. It was odd seeing a guy seated behind the desk. Based off his uniform, he was also a student at Kuoh Academy but Issei had never seen him before. He must be in a different class, though judging from his appearance he looked to be maybe around the same age as Issei, possibly younger. Different grade then?
"Oh! S-Sorry! I didn't mean to just barge in like that," Issei apologized with a sheepish smile. "I'm looking for Rias, have you seen her around?" He took that moment to quickly look around the room, confirming that Rias was nowhere to be seen. He felt a bit disappointed by Rias' absence but turned his attention to the stranger. "So, you must be a new club member, right? I'm Issei Hyoudou, nice to meet you!"
