Hey, welcome to the boards, imjoshua.
There's not quite a black and white answer to your question, as there are many different factors and methods of stretching which could lead to varied amounts of stretching of the skin. Most of the methods and exercises I've encountered didn't seem to leave my member quite wrinkled, but part of that reason was because my flacid length also increased through stretching. I grew into my new clothes if you want to see it that way.