I haven't read every comment on this thread yet, but the few I've read are along the lines of "Tell her everything right now and don't string it out." In my case, I just don't see that as necessarily the only or best advice. My personal experience is that it's been better for me to let her know that I'm trying to balance being truthful against the very real possibility of overwhelming her. I've made it clear that my taste extends beyond what she's comfortable with and I haven't gone into great detail about specifics. The things I've made clear are that I'm heterosexual, monogamous and that I love my role as the man in our relationship.
In my marriage I treat it more as a want-to-know basis. When she either says or shows that a particular issue makes her uncomfortable, I back off but try to make it clear that I'm backing off for her. She knows that I would wear a bra and makeup, given a choice, but I'm not pushing it on her. We don't have hard boundaries but have both seemed to try and reach a balance.
