It hurts a bit the first time yes

. But it will feel alot less after a few times.
When I started plucking it did hurt a bit, but now when I do it it is more of a tingling feeling to it

.
And yes look at a few different styles and which ones that may work on your face, because the eyebrows can really change your looks and you want them to make you look better and not the other way around.
The first time I did it I used an eyeliner pencil to draw the shape I wanted and had that as a reference

.
Regarding other males reactions, I am working in a very manly environment and of course you can tell the diffrence if you look at them and then me, and I know that they can tell, but I have never gotten into trouble because of it. So I think its no big issue if you stand out as confident and secure in who you are. People respect you alot more if you look confident.