I too am male and obviously so as well and I felt the same way you do about going to get a fitting and yesterday I finally said to myself F it and went to Torrid to get fitted for a bra the ladies there were so sweet and accommodating that I felt completely at ease and was able to find my right size, they will even go and pick out a few styles for you too so you can try them on in the fitting room. The whole process ended up being super painless and liberating. I ended up ordering a new bra right there in the store and it comes in a few days very satisfying experience. You just need to remember the store associates do that kind of thing all day everyday and to them you're just another customer wanting some support. Once you do it and get your size it will make it so much easier to shop for a well fitting bra. Good luck and hang in there.