as long as there is suction, its painful - when baby latches on, its the nipples that is painful whereas when you pump and you have sore nipples, the whole area is painful - nevertheless, like i said, the baby is the best 'extractor'!
for bras, u can buy extensions if ur cup size remains the same.
cheap clothes? i dunno leh - er, big t-shirts? nice maternity clothes all very expensive leh...