I just played this for the first time—or one path up to the current end of content, anyway—and really like it. The writing is excellent: sure, there's some odd phrasing and the occasional word used or spelled incorrectly, but it's nothing a copy editor couldn't fix.
* More importantly, the compelling way the story is told and the way these characters are made to come alive is very impressive, and the graphics are good, with lovely character designs, not the ridiculously exaggerated proportions seen in many other erotic VNs.
One thing that struck me, though: where is this story supposed to be set? Because it seems to be in the US, with the friend coming in from Boston and all, but then these high-schoolers are freely buying alcohol (even vodka sold in a convenience store, which most states don't allow) and getting served unlimited drinks in restaurants and at charity galas without anybody questioning it. That feels quite a bit off. Unless set in a parallel reality or imaginary country, as some games do, I think a few words about fake IDs and that Cassie's dad's status means the rules don't apply to her, or something like that, would help it feel a little more grounded in reality.
* The Naughty Captain:
For example, I'd suggest doing a search/replace for "subtility," changing it to "subtlety," and in places where you use "malice/malicious" to describe something where there is no real spiteful intent, just a desire to tease, I think "mischief/mischievous" or "glee/gleeful" would be better word choices.
