#noncanon!

In both instances, Kit doesn't know what the frick he's doing and is aggressive/bitey to cover up his insecurity. He also has a skewed view of love/affection in general, so he partially thinks you're kinda... Supposed to do that. dfklsdfj He genuinely likes Sails, so he's mostly just embarrassed about the whole thing. But with Tails, he is a bit of a shit on purpose. They have history and even though Kit's not trying to kill him anymore, he still sorta hates him. While also ssssort of liking him? Feelings man, what even are they??? (Being confused about this only furthers his animosity towards poor Tails. Who hasn't really done anything to deserve it. sdkfjlsdfds)

Anyway, now that he knows Tails is into him, he'll totally use that against him. He tests the waters, seeing what bad behavior he can get away with . He's going to have fun with it (I personally love it when Kit is a conniving a-hole. Can you tell.). So the above happens... And Tails is like "Dude, wtf? Omg, why it so hot when he smiles evilly at me like that? Oh Gaia, I'm in trouble. dskflsdjf"

Soooo yeah. Their relationship doesn't start out all that healthy. Eventually, I could see it going either good, bad, or terrible. Bad being that they break up and have a falling out because Kit can't stop being a shit. Terrible being that they stay together despite Kit being a shit (nooo, poor Tails! T^T). Good being that they finally come to an understanding where they have a healthy relationship (be it a continued romance or shifting gears to respected friend/ally). Not really sure what it would take to get there, but that's about as far as I've thought of them together-together up until this point. Idk, maybe Cream would find out how Kit's been treating Tails and beats his ass. \j dsfskdlfjsd

But yeah, one of the reasons Someplace!Tails never pursued Kit despite his long-time crush was because he was aware of how badly the baggage between them still effected Kit. And that it probably could never truly work because of it. He thought he was doing good by pushing his feelings down and just giving Kit space. Which, based on the above... I mean, he was mostly right. There's so much more I could say on ALL OF THE POINTS I've made, but I'd be writing a daggum book.

Long story short, I've thought about vanilla Kit/Tails from the Someplace au before. A bit. :D So thank you @Corvussio for giving me an excuse to ramble about hypotheticals and stuff! ^-^

Also, fourth-wall-breaking-Sails is going to kill us for "taking his man," so um. Run. 8D;;;