As a massage therapist, this is probably one of the most common requests I get. The neck and shoulders work very hard and hold a lot of tension from stress. An experienced therapist should know plenty of techniques to help you.
Whether it is your first massage or your 20th, you have the right to dictate where and how you are touched. If the pressure is too deep, say so, and the therapist should lighten up.
P.S. I don't know if it was the strangest, but I once had a woman who asked me to work on just her feet for an hour. That was probably the worst request I've had.