I have never cross-dressed, because I look bad enough as it is. Me in girl's clothing, however pretty I might feel, would be an abomination against the entire physical infrastructure of visible light.
But... you're your own MILF! ;__; And pssh, don't even, you look fine.
Um... I can't say I ever have CROSSDRESSED, but I've worn articles of men's clothing. I like men's jackets and hoodies and t-shirts a lot. That really doesn't count though. xD