I don't understand what I'm supposed to do after the crossdressing therapy session. I've gotten up to level 40 and nothing else is unlocking.
Higher levels only unlock a few areas, some content is related to the story progression. Check the mission tab if you have any ongoing quest, or there's an upgrade you can buy in the computer that shows hints in some areas of the game which can help progress. But you might have also reached the current end of the content which is a session with the therapist about a dream the player had.