I have asked a man to wear my thong panties before, because I wanted to see what lilac-coloured lace panties would look like on him. He was a great sport about it..
to vanilla guys i've painted their nails, put makup on them. i actually helped one dress as a hooker for halloween in high school...fishnets, skirt, bra with filler material wig, the works. It was quite fun...