Notes:

From the tweet:
"I’ve been seeing some confusion about the timeline of events so here’s some more stuff in chronological order, showcasing more of just how out of nowhere some of these transitions were and how pushy it started to feel, where it was hard to do anything but just try to move on"

My Observations, as Not a Detective
Note that Chuggaconroy says he'll continue with the shoe-thing if GreatCheshire wanted, and she says she's doesn't mind it. Additionally, Chuggaconroy also states that it's only sexual between him and his SO, and simply enjoys talking about shoes with his friends in general (though no proof of him talking about shoes with his friends has been provided, and I don't remember any videos of his or with his collaborators where he talks about shoes).
As it stands, we don't know if the asking of permission came up earlier, so Chuggaconroy could have still talked about that kind of stuff unprompted before GreatCheshire was comfortable with it, but this excerpt does show that Chuggaconroy did ask for permission at some point, and GreatCheshire stated that she was fine with it, opening the possibility that she was fine with earlier interactions.
However, as the tweet states, she felt he was being far too pushy, and the "asking for consent" Chuggaconroy did does seem less like asking for a yes, and more like laying out the cards and looking for a no. Additionally, Chuggaconory is a big YouTuber, and regardless of the size of GreatCheshire's channel, having up to +1 Million fans come after you is something no sane person wants, so it's possible that she's never tried opposing him due to this fear.
Then again, as Rylade475 linked through different tweets, it's entirely possible that GreatCheshire is exaggerating the issue, and is doing something similar to what she helped do to QuintonReviews, as talked about in this video (probably. I didn't watch the video, just read the comments. Chalk that up to failing to be a proper internet documenter, and general disinterest).
Regardless, I'm not a professional on social interactions, and I have no experience with decoding drama, much less internet drama, so my analysis/restatement of facts and speculation should be salted well.