My first reaction could be from, wow, what great style, to, oh, that is so ugly... depending on whether I like the particular bag and outfit. In other words, exactly as when I see a woman carrying a bag.
That said, in general, I really like the principle of men carrying bags. I kind of love everything gender fluid, tomboyish women, the garconne style (check my avatar), heterosexual men wearing make up (this was totally normal in the 80s, what happened?). I think our dress codes became so stiff in the last couple hundred of years... We tend to forget, that not so long ago it was perfectly normal for men of whatever persuasion to wear pink tights and heels, adorned with a big silk bow on top. So it is about time we take men from the gray suit straight jacket we have put them in (mind you, I do love a sharp blazer, hardly wear anything else).
To answer your more specific question, what would I think if I see, as you put it, a feminine guy carrying a (so designated) woman purse. I may assume they are gay, without giving it much thought. Yes, perhaps prejudice, but probably that would be my assumption without dwelling on it. My thinking would be on the particular style.
Being as you are a teenager boy, which is where my son is heading fast, I would probably also be a tad jealous. I have done something wrong, because he doesn't strike me like the type who is going to be adventurous in his fashion choices... oh well, he does wear an Eastman bumbag crossbody style, so perhaps there is some hope.
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