I have tried a couple of times and I could get pretty close. But it never felt comfortable - too much pressure on my neck lying back. That was when I was quite fit and even then I was never very flexible. Now I am in average shape and don't bother trying anymore. I love to see pics or vids of sexy ladyboys who can suck their own dick though ... very sexy
The coolest thing I have ever had was on two separate occasions I had a ladyboy suck me while she was fucking my ass. Very hot!
My two favorite sexual activities combined together. Anyone else experienced this?