Issei from High School DxD is often a popular character in these crossovers. His perverted yet determined nature can create some interesting interactions when combined with the Pokemon world. Maybe he tries to use his charm on female Pokemon trainers or gets excited about rare Pokemon in a way that's similar to his reactions to girls in the original series. Another popular character could be Pikachu. Pikachu's cute appearance and powerful electric attacks make it a favorite, and seeing it interact with the characters from High School DxD can be really entertaining.
One interesting crossover could be the combination of Pokemon battles with the supernatural elements from High School DxD. For example, a character from High School DxD might use a Pokemon in a battle against a devil or a fallen angel. Another aspect could be the integration of Pokemon training into the school curriculum in the High School DxD universe. This could lead to some really unique storylines where students compete not only in the usual DxD battles but also in Pokemon contests.
Ash would probably be curious about the devils and angels in High School DxD. He might try to befriend them with his friendly and innocent nature. The devils and angels, on the other hand, would be intrigued by Ash's Pokemon.
A possible crossover could involve Ash meeting Issei. Issei might be intrigued by Ash's journey to become a Pokemon master. They could exchange stories about their goals and the challenges they face. Ash could also show Issei some of his Pokemon moves and abilities, which would be really fascinating for Issei as he's used to a different kind of power system in his own world.
In a Naruto and High School DxD fanfiction, there could be a scenario where the protagonists of both stories meet in a neutral dimension. Issei from High School DxD might be intrigued by Naruto's ninja skills and determination. Naruto, in turn, could be curious about Issei's Sacred Gear. They could start training together, sharing their knowledge and skills, and ultimately have to face a common enemy that threatens both their worlds.
One possible fanfiction could be about Naruto characters attending the school in High School DxD. For example, Naruto's positive and determined attitude might clash with the more complex social and power dynamics in the DxD world. He could make new friends or even rivals among the devils, angels, and fallen angels.
One idea could be that Ben Tennyson somehow gets transferred to the world of High School DxD. He has to keep his alien forms a secret while dealing with the devils, angels, and fallen angels in the school. Maybe his Omnitrix could be misinterpreted as some kind of powerful devil device.
One possible fanfiction could be about Naruto characters somehow ending up in the world of High School DxD. Maybe Naruto's skills in combat and his determination would make him a formidable opponent in the battles that often occur in the High School DxD universe. He could form interesting alliances or rivalries with the characters there.
A fanfiction could focus on Naruto's training regime influencing the characters in High School DxD. His intense physical and mental training could inspire the students at the school. They might start incorporating some of his training methods, like running up trees or on water, to improve their own strength. And Naruto could also learn from their magic-based training and combine it with his chakra control for new and powerful techniques.
A fanfiction might explore how the power of the Excalibur in High School DxD would interact with Naruto's chakra. Since the Excalibur is a powerful holy weapon, it could have some interesting reactions when in the presence of Naruto's unique chakra, which is different from the magic in the High School DxD world. For example, it could either enhance or nullify certain abilities depending on how the author writes it.