Many guys have said to me that they'd like to "try" a ladyboy but would like to chat with them first to see if they're comfortable. One way you could do this would be to try and communicate with them via a social network. Do a web search and register with one. Examples could be urnotalone or ning.com. Select a ladyboy and then ask some simple questions - Hi, how are you?, what are your interests? etc. I'm assuming you'll pick somebody from a country which you can go to because the next step could well be a meeting where you have to take it from there.
Another way is, to go to a nightspot where ladyboys sit and have a drink with you. Sit, chat and see how it feels. Or else, if you're shy walk around the surrounding area; maybe there's a chance you could just meet somebody outside the bar?
For that matter, if there's no ladyboy bar in your town, try hanging around areas where they've been seen and see how it goes.
That's the basic idea. Obviously, how fast you proceed depends on you.
Questions about this? Ask away!
Pictured is Aldrch Sy a 24 year old ladyboy from Iligan City in the south of the Philippines.