A fresh High School DxD fanfiction short story focusing on their relationship. I kept it light, romantic, pervy in classic Issei style, with action and harem elements, while staying true to canon personalities and lore.
Chapter 1: The Witch's Contract
The Hyoudou residence was unusually lively that afternoon. Rias and the others had gone out for a "girls-only strategy meeting" (which Issei suspected was mostly about planning dates and glaring at each other over who got him next), leaving him alone with his new contracted magician.
Le Fay Pendragon stood in the living room, her shoulder-length blonde hair catching the sunlight like golden threads. She wore a simple Kuoh Academy uniform modified with subtle magical runes along the hem—her personal touch. At first glance, she looked like a cute first-year, but her blue eyes sparkled with ancient knowledge and a hint of shy excitement.
"I-Ise-sama! Thank you again for accepting the contract!" Le Fay bowed deeply, her cheeks flushing pink. "I promise I'll support you with the best magic the Pendragon line can offer!"
Issei scratched the back of his head, grinning like an idiot. "Haha, no need to be so formal, Le Fay-chan! We're comrades now. And... well, you're super cute, so it's a win for me!"
Le Fay's face turned even redder. She'd been a huge fan of the Oppai Dragon ever since she first saw his broadcasts. Joining Vali's team had given her excitement and power, but being around Issei felt different—like coming home to warmth and... something more.
The contract ritual had been performed the day before under Ravel's strict supervision. A five-year pact sealed with glowing magic circles, binding Le Fay's vast repertoire of spells (including some forbidden ones from the Golden Dawn) to Issei's Boosted Gear. Ravel had grumbled about "another rival in the house," but even she acknowledged Le Fay's talent surpassed most candidates.
Chapter 2: Training... and Tension
"Let's test our synergy!" Le Fay suggested, clapping her hands. She summoned a small teleportation circle and whisked them both to a secluded training ground in the mountains—far from prying eyes.
Issei powered up his Boosted Gear. "Boost!"
Le Fay moved with graceful efficiency. "Support Magic: Amplification Array!" Golden runes swirled around Issei's arms, multiplying the power of his boosts. She followed with defensive barriers and precise offensive spells—fireballs shaped like dragons, illusionary decoys, and healing waves that felt like Asia's Twilight Healing but with a spark of ancient British mysticism.
"You're amazing, Le Fay-chan!" Issei shouted, punching through a boulder enhanced by her magic. "With you, I feel like I could take on anyone!"
Le Fay smiled brightly, but as she cast a complex teleportation spell to reposition them, she stumbled. Issei caught her instantly, his strong arms wrapping around her slim waist. Their faces were inches apart.
"I-I'm sorry... Sometimes the mana drain catches up," she murmured, not pulling away.
Issei's perverted mind went into overdrive—Soft... smells like flowers and old books... Oppai Dragon approves!—but he held back. This wasn't just any girl. Le Fay was special: kind, talented, and she looked at him with genuine affection, not just the harem chaos.
"You okay?" he asked softly, his voice unusually gentle.
Le Fay nodded, her hands resting on his chest. "Ise-sama... I've admired you for so long. The way you fight for your friends, your dreams... even your lecherous side is endearing. It makes you you."
Issei's heart raced. "Le Fay-chan... I want you to stay by my side. Not just as my magician, but... y'know..."
Chapter 3: The Date and the Spark
That evening, Le Fay joined the shopping trip the girls had planned. Rias raised an eyebrow but allowed it—managing the "Girls' Club of Hell" required balance.
They wandered the mall together. Le Fay dragged Issei to a bookstore for grimoires (which he pretended to understand), then to a sweets shop. He bought her a giant parfait; she blushed and fed him a spoonful in return.
Later, a minor stray devil disturbance interrupted. Le Fay's magic combined with Issei's power made short work of it—her barriers letting him charge in safely, her spells amplifying Dress Break into a devastating combo that left the enemy stunned and clothed... mostly.
Back at home, under the stars on the balcony, Le Fay leaned against him.
"Ise-sama... do you think I could be more than just your contracted magician?"
Issei wrapped an arm around her shoulders. "You're already part of the family. And yeah... I like you, Le Fay. A lot. Your smile, your magic, the way you believe in me. Let's make this contract the start of something awesome."
Le Fay's eyes shimmered as she stood on tiptoes and kissed his cheek. "Then... I'll support you forever. As your magician... and as someone who loves you."
From inside, Rias called out teasingly, "Don't monopolize him too much, Le Fay!" But there was warmth in her voice—the harem grew stronger with every new bond.
Epilogue Tease
In the coming days, Le Fay's integration deepened. She helped train with Rossweisse on combined Norse-British magic, cheered Issei on during Rating Game prep, and shared quiet moments where her shy affection melted his heart (and fueled plenty of "Oppai" fantasies involving magical enhancements).
The Red Dragon Emperor's legend continued—with a brilliant witch by his side, ready to weave spells of love and power alike.