I cry in maybe a third to half of my sessions. Kind of depends where I am mood-wise in general and what I'm working on in therapy at the time. When I was pregnant I cried more often and with buckets of tears. I wasn't necessarily more upset or emotional when I was pregnant, just that the tears came more easily and copiously. My T usually looks empathetic and sometimes gets a little quieter but mostly we just continue talking.

I had a hard time crying when I first started therapy in my teens because I had a hard time experiencing any negative emotions without forcibly shutting them down (which was part of why I felt so crappy in the first place, although I wasn't aware of it at the time). It felt weird crying in front of somebody at first, but eventually I got used to it.