I chose #2. Though something in between #2 and #3 would be my preference.
I'm a bottom with guys only... but do enjoy occasionally topping another hot trans girl.

I have only topped anally three times. Twice with per-transtion girls who had really only experienced toys before. So was a bit tight. Took some effort to enter.
And the third was my ex-gf who was really tight. I don't think she was an anal virgin, but she was so tight that it actually hurt a lot. She is also trans.

The only other time I tried to top analy was with my first gf (cis girl). But I didn't know what I was doing at the time (no lube >.<) and she was a complete anal virgin. So needless to say. I didn't even begin to enter her before she stopped me.

As for my anal tightness. I's assume I'm somewhere in the middle. I haven't had any complaints. :D