I didn't mean to offend you, Nyx; she asked for ideas and I gave her some - that's all.Oh for God's sake...
Before you do any of the dressing him up and publicly humiliating him, you should first TALK TO HIM ABOUT IT! You have to discuss boundaries first - both yours and his. My ex was submissive but in no way would he have enjoyed being dressed as a woman, nor did he have any desire to be publicly humiliated in front of ANYONE. Strap-ons, however, he was interested in.(And that really is an awesome idea, just make sure you take it slow, start out small, and use lots of lube).
Seriously though, you must discuss these more serious things before you decide to make him do them. A submissive man does not automatically come equipped with a list of things he'd do. He won't just fuck a shemale or become a crossdresser because you say so. Submission is a gift, not a right.
As far as "making" him do something - or anything - a discussion about boundaries beforehand as well as respecting those boundaries IS A GIVEN, as is the establishment and use of a safe word.
My apologies for not making that clear in my previous post that incurred your ire.