Lets face it, not all shemales asses are the same. Now we all much prefer a tight ass to fuck but on occasion we are just too big to comfortably fit. This has happened to me a couple of times, and after a quite a bit of fingering and lube I always got it in, but at the expense of the poor tranny I was fucking.
Now you could just take it out and let them suck your dick, and I have done that a few times. But honestly for the tranny your fucking its better to finish the job so the next time it won’t hurt as much.
Now not being heartless I do feel sorry for them sometimes particularly if they are reduced to tears. This indeed happened to me once or twice, with an Asian tranny or two. (they seem to have the tightest assholes). But eventually they got though it like a trooper and complemented me on the size of my dick.
So I guess the moral of the story when fucking younger Shemales be gentle.
From Shemale Ambush 
hey i was just wondering where you find these gorgeous shemales. im living in Kentucky and i havent found any! so if u could give me some tips id appreciate it
Hope 2 hook up with a tv and play drer up
Wishing I was on the bottom of the dog pile
ilike to see she male