From a perspective of a woman in a relationship...
If you knew your boyfriend has a thing for this things and he would ask you really nicely to wear theme for him, would you (perhaps you already did) feel good and do it or would you feel bad, perhaps even offended? Most guys really like this things and I wonder, what is your perspective on this?
I'm not really comfortable with this level of thing, but I know my boyfriend likes skirts and lingerie. I'm a girl who always wore jeans, but for him I've picked up a few skirts/dresses, and some bedroom wear. The pleased response I get from him is usually more than the discomfort I experience at being self conscious, and with encouraging words and smiles from him, I can usually open up enough that I'm not worrying about how I look.
Yes, it kills the mood for a bit, but I find that when the girl feels like the mood's done, the guy can encourage her to feel sexy and confident again with a little bit of effort. I'd say try to stay playful and upbeat for a while, and if it's her style, get a little romantic about it. 10, 15 minutes of your time off track could lead to several hours of fun in the manner you were looking for, and make the next experience easier.
Yeah I have done/will continue too/enjoy this type of dress up. I do Burlesque dancing so this is a pretty normal occurrence for me. I don't have heaps of body confidence but I just enjoy the look and have fun. I'm single but in the past I have dressed up in this style, especially the stocking or over the knee socks, most guys seem to love that.
Some women just won't do it at all. It's a comfort level for them. Most women though, if you let them know that you love them no matter what they're in will be glad to do it for you. They sort of already know that men are visual creatures and the sexier the clothes the more turned on he's going to be