First off, as many have already stated, what you're saying OP is creepy... Really creepy... You're trying to turn dating into rape...
Now, I'm a transwoman, so I've seen this from both sides of it, out of the 2 cismen (3 if you count the one guy who I dated and ended up being raped by) 1 transman, 2 ciswomen, and 2 transwomen I've dated, I was always the person to ask them out, to make the first moves (With consent, or... you know, implied consent... in the form of hungry eyes... well, ravenous eyes...mew) And I've ALWAYS split the bill unless I bought something more expensive, it just seems like a HUMAN/RESPECTFUL thing to do, regardless of gender.
I think the problem a lot of people are having in relationships like this, is that for one, you're trying too hard. I'll let pansexual pop star Mika help me here http://www.youtube.com/watch?v=6md5RSnVUuo&ob=av2e
And another, is communication, past my first few relationships, I've only been in D/s relationships, and they've all worked more or less, and require VERY good communication to work, like, I cannot stress how important communication is in that sort of relationship. Of course, even in a vanilla relationship, it is still crucial, and if you honestly can't ask for consent, then you really need to either work on your communication skills, or... you know, just lock yourself up right now, because you're very likely to intentionally/accidentally commit rape... (Accidental rape being having sex/being intimate with someone without concrete consent, not a "I uhhh, I guess so") Personally, I won't do a thing before what I would call "enthusiastic consent" (Which can also be a good way to work into foreplay, it tends to be more than just a little enticing *grin*)
Really people, if a fugly, bitter, misanthropic, transsexual with horrible self-image issues is able to communicate desires/needs in a constructive manner with her partners, why are so many people relatively normal people finding it so hard to communicate these things?