It took me many months to cry in front of all the T's I've seen. I think in the case of first T it was over a year.

It got to the point I was so desperate to cry in front of T that I'd get myself really emotional just before leaving for a session - i.e listen to some deeply sad music, watch a sad clip on you tube, something like that. It didn't work every time but it got me to the point I could well up in front of T and from there on I felt more comfortable about it.

But it can take a very long time. Be patient with yourself.