I don’t know if I’ll ever do any sort of Digimon/Pokémon crossover, but it’s a fun idea to consider. I haven’t fleshed out most of the Digimon cast quite as much as I have Ash, but I do think I prefer seeing Tai on bottom. Something about his outgoing personality and sporty look makes me see him that way. I like Ash on bottom for similar reasons, though, so in all likelihood I’d have them switch.
Actually, the more I think about it, if I did do a Tai/Ash pic, it’d probably be something like Pikachu fucking Tai while Agumon fucks Ash, and then the boys are making out in the middle. But idk, there’s a lot of fun ideas to be had with something like that. As far as Tai’s preference, I’m sticking with what he says here.