Thank you. I think the problem that I had was that at her current level, it says "max out pain, pleasure, and humiliation". This leads to trying to max those scores *before* using the dildo. Whereas what this does is max her humiliation, but leave only enough points in pain and pleasure that the dildo treatment will max our those scores. There was something similar with her for the first time sitting on the lap. It would be useful in this particular situation (first time) to clear up the message or hint that humiliation needs to be maxed and the others need to be close enough to max out once the dildo treatment is used.
*Note: My final comment should not be construed as a derogatory comment on any aspect of this game, and is merely a polite critique from one developer to another.