No, it's not too much to a ask. I have sort of your problem as I am on the borderline between a 38DD and a 40C. I HATE underwire bras. I found one bra I liked at Lane Bryants but it didn't come SMALL enough for me! They had discontinued the only nonunderwire bra that fit. I also had sidewire bras. I found a bra a JC Penney's that fit, but had a side wire, which was really a hard piece of plastic like a swizzle stick flattened. I just took a pair of nail scissors and from the indise cut a small slit and pulled the plastic out, and the bra was much more comfortable. I found another bra in the Roaman's catalog and it was perfect and of course they discontinued that one. Forget Victoria's Secret or Frederick's of Hollywood, they have nothing. So it is pretty much Lane Bryant, Penney's, maybe Sears, or a specialty store or catalog's like Roaman's, Jessica London, Woman Within, or other online stores for large woman. You are just going to have to try on bras everywhere and get yourself at least three, one to wear, one to wash, and one in the drawer, as my grandmother used to say. I know what you mean about someone trying to fit you. It never works. You just have to try them on, one at a time. I also forgot that you can also try outlet malls that have a Hane's outlet in them. Hanes also has a large women's line that has a large supply of products. I went to the Hane's outlet store at the outlet place near the City of Industry on Telegraph Rd where the old tire factory used to be, and they tried to fit me and I just had to try on about a dozen bras before I found one that fit right. As a diabetic, I cannot have a too tight bra and it cannot rub or I break out in infection. I prefer cotton bras, preferably knit. The nonwire Lane Bryant bra they discontinued was just brought back due to popular demand. It holds me in pretty well and doesn't rub and has no underwire and has wide padded straps for comfort. . You might try it. Good luck. All I can say is shop, shop, try, try, and if you find one that is THE ONE, see if you can get it cheaper online. You never know!.