i didn't dress the boys in girl clothing (except once, and it was an emergency!), but i didn't curtail any pretending they chose to do. i gave my husband a little pink dress once, but it was to announce my 2nd pregnancy that was supposed to be a girl, but intuitively i knew it was a boy (after i'd given the dress. ) i thought the diaper covering panties would be a real hint to dh, but all he said was, "looks a little small for me."
third time was a charm, my sister had used the dress on her daughter, and surprised me with it on dd's arrival. yay! brought me to tears.