Well, I just kept sabotaging her and once she got happy, when I persuaded her to show her boobs - she started talking about the massages! Woohoo, this is getting exciting!Here's what I did, but that's no guarantee it'll help in your cases.
Stopped studying with her completely. Eventually she got her spanking. This forced a small cutscene right after with dialog. I resumed studies but sabotaged her work til she got another spank. Resumed studying and a new option appeared for massage. IIRC.
I also promised Lisa a hand massage in the mornings of fridays, but there doesn't seem to be an option for that.
...oh, but there is in the evenings
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