I've never been with a TS but I want to give it a shot, getting fucked by and fucking a tranny sounds so damn hot.
I've never taken it in the ass before, I'm sure it's gotta feel great but it's gotta freakin' hurt the first few times.  

question: How did you first take it and what was it like ? how do you suggest I get started?

If you're looking to avoid pain, invest in some butt plugs to get used to penetration.  Work your way up from something that's fairly small to something that's about the right size around.  Give yourself some time to work up in size; it's not something to get done in an hour.