Rich: For most of us guys, our bra size depends a great deal on whether it is wire free or underwire. Most women's breasts sit close together toward the center of their chests while ours are wide spaced. I personally have as much boob under my arms as on my chest. A while back, I found a practically new wire free bra with molded cups in a rare 42B size in a thrift store. Much to my disappointment, I didn't even come close to filling the cups. However, when I stuff the underarm boob into an underwire bra, I fill a 42C without wrinkling and can even wear one of my wife's 42Ds without looking totally ridiculous. She can wear wire free and underwire in the same size interchangeably. I can't.
For every day wear, I usually wear a pullover leisure bra or low impact sports bra. It doesn't lift and shape the underarm boob like an underwire, but it keeps things from moving around and it is almost impossible to detect under a shirt because it doesn't have hooks or strap adjusters. I think these are great as a "first bra" because they are easy to hide and they are sized according to chest measurement. These aren't for everybody and if you are much bigger than a C cup, you probably need to get fitted for a big girl bra. Incidentally, Rhonda Shear makes a variety of pullovers with underwire cups so you get the advantages of both types. Again, these aren't for everybody but I am planning to order a couple more in the future, maybe in less manly colors than I am used to and with lace accents. Yeah, my feminine side is starting to show a bit.
I have resisted wearing underwires for a long time because they make me project more but after 4 years of wearing bras, I sort of don't care any more. You will get there eventually. Try an underwire, you may be surprised at how large a cup you fill.