I do it on a regular basis since I live as me except when forced to make a male appearance for work. Most of my male friends have been supportive but not all. I think that over time they have become more comfortable with me and being out in public with me. This has been over the last year and I think it has helped them that I am always Suzanne. If I was sometimes Crossdressing it may have made the adjustment harder. If they are your friends in a real way they will make the effort.
Suzanne