Ashley's natural look is already available in sex scenes, and will soon be available for hanging out in the hotel and pinups.
I don't understand what you mean with the first question. But no, story scenes can only ever use one outfit, which will usually be their default outfit. If this were a fully 3D rendered game, I would love to do that. But doing that in a CG image game would bloat the filesize enormously and cause each update to take a very long time to develop.