I don't know about the crossdressing by experience, but I did know a man that was a drag-queen. He shaved his legs, waxed his chest & his face too. He shaped his eyebrows a tad, but mostly made them into 2 (in other words getting rid of the unibrow). He wore women's cologne too, which, actually, if it's on a man, sometimes you can't tell. I prefer CK ONE. That's for either or, and you can wear it out without someone really picking up on it. Smelled it on a man, and it's uber sexy! He also chose colors for his skin tone that were flattering, and clothes that fit his shape. After all, women come in many shapes, sizes, weights, and heights, and there are clothes designed for them, so it's possible. Maybe read some of your wife's fashion mags (Cosmo and Glamour are fantastic for tips from clothes, makeup, colors, hair...ect.) to get some helpful tips & advice. As far as the anal cleanliness goes. There is almost always a tad bit of residue on toys when engaging in anal play. No matter how much you clean it out. Once that's understood & accepted, then the more comfortable you will be with it. If it's a really big concern, put condoms over the toys/fingers that you use. Makes clean up a breeeeeeeze!