I haven't cross dressed since I was a teenager in the '60's, and then only briefly and furtively. But over the holidays, I decided I was old enough not to have to care what others might think, and I shopped up a storm online, buying a variety of breast forms, bras, and tank tops. While waiting for them to start arriving, I did the old trick of stuffing balloons under my shirt. They felt really good, confirming I'd made the right decision. But they wouldn't stay in place. I really did need a bra.
So after an doctor's appointment, I rolled into a nearby Walmart and headed over to the displays of women's wear. I say "rolled", because a wheelchair is how I get around, which has its advantages. (People tend to give you plenty of room and then ignore you.) Supposedly, my bra band is 34". But what I saw on the racks sized at '34' were clearly going to be too small. I guessed a XXXL might be the right size for me (aka, 42 DD), even though I really am just 5'6" and 130 lb.
At home, I cut off the tags and slipped on the bra. Perfect fit. Just the right amount of snugness. In went the balloons, giving me a 'D' cup, which felt right, even though they created an top-heavy, Dolly Parton profile.
Two things became obvious from the shopping trip. If you exude an air of confidence, no one gives you a second glance, even though a guy shopping in women's wear is unusual. Second, I really do need to learn how women's clothes are sized.
Arindam