Fics like Emerald Star: The Full Journey

Izuku never thought his loving girlfriend, Momo, could be even more perfect. Then she invites him to take part in a unique challenge of Dungeons and Dragons, alongside several other girls. The goal? Complete a series of various D&D Adventures without losing a single party member and win a ludicrous cash prize. Naturally they go above and beyond. Izuku just never expected to gain another three girlfriends.

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