I am not being insensitive here, but.....Alarm bells are going off. Now alarm bells can just mean "excercise extreme caution", or they can mean eminent danger.
Since you are asking for advice, I would like some info. How did this idea come about? How did you "meet" this guy? What really is his deal?
As we all know, there are too many weirdos out there that would love to do harm to someone like us, why they exist is quite beyond my comprehension, but they do.
I as a straight male would not want to go on a date with another male, unless we were both CDs and there was absolutely NO romantic tendencies. But that is me.
Jennifer B stated something that I think is painful truth. We will never know how it feels to be a female, just like we will never know how it feels to be a cat, or a dog. The most you will get is how it feels to be treated like a woman in our society. You will experience the silly customs that were made when women were considered much lower than men and incapable of doing things themselves. Hopefully you do not experience how some men truly treat women, and how some women accept that treatment since they have known of no other way.
What ever you do, be safe, have an out, and bail if anything seems incorrect.