This question is referencing a much older Ask Izzy did, where he was asked who the sluttiest DigiDestined was and volunteered himself. I figured it’d be cute if Tai basically did the same, implying most of them would’ve done the same.
Here’s the One-Shot that won the selection in July. The idea here was pretty simple: A big orgy between the Season 1 and Season 2 versions of Tai, Matt and T.K. This one was a bit difficult, just for technical reasons, but I think the final result turned out pretty decent. I hope you all like it! ^_^
I guess I haven’t drawn T.K. with anyone but Matt, but that’s really just because I love the incest angle. But T.K. and Tai are totally dtf, so here’s a fun little threesome since I love Matt and didn’t want to leave him out.
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.