I kept getting questions from one of my mentors about what the whole shot means in a story sense. I was setting up a situation, but never dealing with the results. After a lot of back and forth and brainstorming, I came up with an ending that I think resolves most of what I bring up in the test...at least concerning the girl... In addition to the question of the ending, I have also addressed a lot of notes from other mentors, friends, and coworkers. The set has now also been further tweaked to provide proper staging for the final idea.
The fat guy in drag came from a brainstorming session with a friend of mine. At first I thought it was too out there and strange, but the more I thought about it, the more I realized that it solves the issue of where the clothes went. To further extrapolate it out, she was in the shower, so she definitely wouldn't have heard him come in, and try on her clothes. The question then of, 'what are the consequences of her lost clothing-now on a fat guy', is solved by the fact that he has now stretched her clothes and ripped her skirt.
Hopefully I'm not too far away from being done with this and able to start my next test. At least I got it in before the end of the year!