Breaking in New Outfits (19/M)

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Hello everyone. I recently ordered and received two crossdressing outfits. I've tried them on for a few minutes but I haven't worn them for any extended period of time. I'm curious on any ideas that you all have for allowing me to break them in. I would be open to hidden public tasks but bear in mind that it is a bit cold where I live. I live with others but I often have the house to myself for extended periods of time so it shouldn't be too big of a problem.

I have a list of likes/limits in my signature and a link to the outfits themselves and my toys as well. I'm interested to see what you guys can come up with!