Disclaimer

High School DxD is owned by Ichiei Ishibumi / Funimation

Dark Souls is owned by FromSoftware

Issei sat with his back against the wall, breathing heavily.

'Damn it… I'm not going to make it out of this one, am I?'

"Where did he go!?"

'I can't run anymore. My body is too messed up at this point…'

"There he is!"

'My only regret…'

"Time to die!"

'…is that I didn't see their more of their boobs.'

"This is what you getting for peeping on the soccer team, pervert!"

He watched as the captain of Kuoh Academy's soccer team bounced her ball on her knee, and knew her chest was mocking him as it bounced as well. He was so close, but of course Matsuda and Motohama had to hog the peephole. Their arguing got the girl's attention real quick, and they wasted no time in dispensing justice to the trio. The other two had managed to get away but Issei was not so lucky. Issei closed his eyes and awaited the inevitable.

BWAK!

"…What the hell!? Who're you!?"

Issei opened his eyes to see someone standing in front of him. Blue shirt, jeans, and… purple hair? He could see they had both arms up in front of their face. By their foot was the weapon of his execution.

"What, are you one of those perverts too?" Their captain accused, but the stranger just stooped down and picked up their ball. He tossed it back to them, and the captain stared at them for a moment before sticking her nose into the air.

"Hmph! Let's go girls. I think the pervert learned his lesson." With that the soccer club turned their backs on them and left. Issei's savior watched them for a moment before leaving.

"Hey, wait!" Issei stood, using the wall for support, "Who are you?"

They didn't answer, and as they walked off Issei nodded to himself.

'I don't know who you are, but I'll never forget this!'

'It would seem you're a troublemaker even here, old friend. I suppose I'll have to help you as I did then…'

Issei sighed in relief as he sat down at his desk. He had just managed to avoid the soccer club on the way here. He knew better than to hope they had already forgotten about yesterday.

"Attention, everyone, attention." The teacher clapped his hands, and everyone went quiet, "We have a new student joining us today."

The door slid open, and everyone began whispering. A boy with purple hair tied back in a ponytail, piercing, emerald eyes, and a small frown on their face. He bowed at the waist.

"Hello. I am Gwynnus Cindre. It is a pleasure to meet you all." His voice was quiet and formal, and the girls started whispering. Issei, however, rubbed his eyes to make sure he was seeing the right thing.

'Purple hair? Then, is he…?'

Gwynnus stood back up, looked over at Issei and nodded. The girls all gasped dramatically.

"Nooo! He's another pervert!"

"And he was so handsome, too!"

As the girls lamented, Issei gave a determined smile and nodded.

'Don't worry, Gwynnus. Perverts stick together!'

'Hmm… It would appear you've changed more than expected…'

"Gwynnus Cindre, age 15, adopted son of Gwyn Cindre." Sona pushed her glasses up, watching the purple-haired boy from the roof, "Top of his class in his previous schools…"

"…and a human covered in more darkness than a high-class devil." Rias tucked a lock of hair behind her ear, "Cindre… I've heard that name before…"

Sona nodded, "Currently, Gwyn Cindre, head of the family, controls most of the jewelry businesses in town. If it's made of gold or silver, it's most likely from one of his stores. There's also a rumor that he disowned one of his sons, going so far as to destroy every record of his existence."

Rias frowned when she heard that, "What could he have possibly done?"

"If I recall, the rumor said his son aided a rival, though it's unclear whether that means another business or a specific person. I'll do more research into the Cindre family…"

"…And I will keep an eye on Gwynnus." Rias' blue eyes glared into a pair of emerald eyes…

Gwynnus turned back to his notebook, ignoring the two girls glaring at him from the rooftop. While he wasn't quite as strong as he used to be, he should still be able to handle them.

Soon enough lunch came, and as Gwynnus was heading for the door he felt a hand on his shoulder. He turned around to see Issei and two others looking seriously at him.

"Follow us."

He only nodded, and as they led him outside he pulled out a cloth hidden in his sleeve. They reached their destination and when they turned around they stared at each other for a moment.

"Alright, Gwynnus. I have only one question for you…"

The tension was thick enough to cut with a blade, and as Gwynnus could only wonder what question could earn such gravity.

"…Boobs, or butts?"

'…Did… did he just ask…?'

"I… don't understand the question…"

"What's there to understand!? Are you a boob man or an ass man!?" Issei and his friends were suddenly much closer than he preferred. He felt his cheeks flush as he tried to come up with an answer.

"I, t-that is to say-"

"Excuse me."

Gwynnus turned around to see a blonde haired boy smiling at them, a crowd of girls following shortly behind.

"I am Kiba Yuuto of the Occult Research Club. You are Gwynnus Cindre, correct?" At Gwynnus' nod he continued, "I was asked by our president, Rias Gremory, to invite you for tea after school."

Everyone burst into conversation at that, Issei and his friends exclaiming jealousy for this opportunity, the girls praising Kiba for getting him away from the 'Perverted Trio'.

Both sides joined in shock when Gwynnus shook his head.

"My apologies, but I am kept to a strict schedule. Perhaps I can convince my father to allow me some time after school."

Kiba's smile became a bit strained, "Of course. See you another time, then."

With that, he and his entourage walked off as the bell rung. Gwynnus started walking back to class, a mixture of dread and numbness taking over as Issei started walking with him.

'Please, please don't make me fight you again, brother…'

"HYAAARGH!"

The foolish abomination tilted its body up to stare at him, allowing him to safely land on it and crush it beneath his weight. He felt a weight land on his back, and a moment later his comrade leapt onto the beast in front of him, skewering it. As it fell, the blue garbed warrior leapt off, two tentacles reaching for him. He brought his zweihander down, severing the appendages, and the creature screeched as his comrade turned and loosed a great ball of flame upon it. Another approached from his right and he charged it. It rose up to stomp upon him, but he went into a slide, and as he slid under it he brought his sword up.

He stood and turned when his slide finished, smiling as the creature's innards fell and it collapsed. He looked towards his companion, his smile unseen. As he was about to congratulate him, he saw one last beast rushing him from the darkness. He couldn't reach him in time… unless…

"Get down!"

He hurled his blade as hard as he could, and it soared true. His friend ducked and the beast was pinned to the wall. His smile grew, even as the adrenaline wore off and he fell onto his rear. He waved off the attempt to help him up.

"Don't worry about me. Just a quick rest, and I'll be off again."

He could feel the worried look, but his friend nodded and set off. He laughed when their footsteps died out. Finally, he was the hero he knew he could be. He slowly closed his eyes, and a strange bliss took over him…

Issei quickly sat up, blinking the sweat from his eyes.

"What the hell was that dream?"

He looked around his bedroom, taking note of how the sun was just rising. He yawned before lying back in bed. He had a few minutes before he had to get ready for school.

He shot back up, a great realization overtaking him.

"Gwynnus never said whether he liked boobs or not!"

AN: I couldn't think of anything else that fit with the 'Gwyn' naming scheme, so Gwynnus it is. To be clear, this will be a Dark Souls 1 only story.