For the Kimberly scene specifically, I believe you're talking about
where to cum (On Her Face), right? For that, you need to have
the MC globally perverted. (In other words, it's not just how people might perceive him to be; it's his actual true nature.) That will be true if you have chosen the perverted option both times when you see the blue-red screen split (only 2 possible up to that point). Specifically:
- Choose to Take Advantage of Lauren when she's in the MC's office earlier; and
- Give in to Kim when she proposed a titjob (which you have already done obviously by being at the point you describe — i.e., having sex with Kimberly).
If both of those are choices you've made, that final option will be enabled for you.