From what I have played
That already exists it's the eager vs reluctant
system the games outright tells you about when you go into the library or if you read the guide book reluctant being closer to sisification where the eager options is more feminization
That's interesting because I'll admit I haven't done an eager playthrough for comparison but most of the reluctant scenes so far read more early transfem then sisification, where Lily's egg hasn't quite yet cracked. (She's in that "being a girl is nice/I want to be a girl; but I'm still definitely a cis guy" phase [as an example see: Her confusion regarding Damien's comments on playing as a girl. She assumed that a guy would be eager to get a chance to be a girl, and rationalizes that as normal guy behavior, and finds Damien's lack of enthusiasm strange even on the reluctant route]) And with the later stuff like the tentacle book even the "reluctant" route feels pretty damn accepting and eager.
As the dev points out there is no "stay masculine" route so "reluctant" seems so far less "reluctance to be a girl" and more "reluctance to openly embrace it and talk about it with her friends." (as well as, providing the option was checked at the start, reluctance to address her bisexuality)
Further evidence of this point: a standard dialogue in sisification stories if the character is asked about their first time is to claim "it was weird but not terrible" or something to that effect. This is often the minimal response the MC can give and still have the sissy route open. It's a neutral response that allows the story to continue while maintaining that tantalizing hesitance to indulge that makes taboo subjects erotically appealing. It often doesn't even result in an increase to the relevant stat if the game has one. contrast Lily's minimal response which is an embarrassed refusal to comment on how she's liking it. The implication of her embarrassment being that she enjoyed it quite a bit but is too embarrassed (may we say even "reluctant") to admit as much to her peer group. Lily's minimal response would be at least the second lowest non-route cancelling option in other sisification games, and in reality might even place higher because 'blushes in embarrassment' is a classically "girly" response and those types of responses often place pretty high in early sisification dialogue options with the reasoning being that they indicate a natural disposition towards "girliness." ie: the character, often a girl, asking the question would likely comment that the sissy is natural for having that type of response.
What I'm trying to say here is that Lily's minimum enthusiasm towards being a girl is skewed fairly high.
Honestly eager vs reluctant feels more like it's going to be enthusiastic vs tentative/slow (again based purely on the reluctant route and assuming a consistent increased standard of eagerness in the eager routing)
I guess it's possible to roleplay greater reluctance by paying instead of taking the scene with inkeeper but still...
tl;dr I spent far too much time analyzing this but basically Lily actively seems to want to be a girl even at her most reluctant, while reluctant sissy characters are often
good at being girls but have little initial enthusiasm for it, and thus the plot is about conditioning them to be more enthusiastic. Lily is already pretty enthusiastic.
In other news love the game so far and can't wait to see what comes next.
