I get my hair cut at a barber shop, and the one thing I discovered there is that they really just want to make you happy.
Unlike at a "salon" where the stylists think they know what would look good on you and be better for you, the barber just does what you like and a good barber prides himself on it. If you ask for something they think is stupid, they may ask if you're SURE, but if you are, you'll get what you asked for.
That said, I never did the shave thing, so I don't know if they get shave requests a lot. Maybe they will think you are a younger guy who is excited to do it for once.
My problem is that I'm not out to my barber, and I started going there before I was full timing. So he's been giving me really good men's cuts, thinking I'm a very tomboyish girl. At some people, I will have to tell him the truth, and I'm nervous, only because he really cuts hair well and I don't want to have to switch barbers to a new (stealthy) place if he is awkward about it!