Must be a pretty specific route, or exacting set of stats, to enable. As I have tried setting stats low, high, and middling. Never see that option.
I do the "Chat" then "You" and all I see is the option for her to show me what she is wearing. I've tried both when she's not following me as well as when she is following me.
I guess I can always try seeing if aggro'ing Bret instead of siding with him changes that aspect or not.
Perhaps you could write a general walkthrough, about which paths you took in the scenes.
Mine looks something this:
1. Always take all the masculine / dominant options, avoid opposite, have sex with the teacher in the train, dominate Lindsey
2. Always take all the incestuous options, starting with the photo in the train
3. For the sister, ignore love and friendship loss, focus domination, don't choose specific corruption if there are domination / love options instead (corruption will make her slutty, bad)
4. Sister at home, tickle attack and dominate
5. In the park, always flirt and make out with Jenny, make the sister jealous and submissive
6. Do not let her be with Jimmy at any point, except when seducing Jenny at the start
7. Do not let them walk around without you
8. Support both girls on Skate training
9. Do no let the sister touch the horse statue
10. Accept Jimmy's ride home, take both girls in the back, masturbate Jenny
11. Back at home, literally the first thing you can do is ask her about her clothing
General tip, always save at the start of any scene. Often there are choices which don't have stat requirements or results, but lead to more / better choices. For example when talking to Jenny and Anny about sex in the park, after the "v-card punch" option, answering that you're not really a virgin will lock you out from talking about incest with them.