To the best of my knowledge the XXX content currently is limited to only the Goo girl but more things will be added in future updates. As to the Sissy content. I am unsure what you mean and are asking about. but I do know the Sissy content does allow you to attend work as usual.
As to caretakers. taking you to work, i THINK thats random I know hte boss will mostly take you out for the morning then ask if you want to go home or go to work with her