@viragomann Hi thank you for answering.
Yes you right, the screenshot doesn't show it, but it was working up to x.x.100.2, sorry about that. Finally I found the problem.
R1 wasn't passing the traffic on to pfSense properly, only ICMP but no more. I changed the command for the static route from -
ip route 192.168.20.0 255.255.255.0 g1/0
To -
ip route 192.168.20.0 255.255.255.0 192.168.100.2
And it worked beautifully. I suppose that between routers there is no problem with that command but pfSense is in a VM and treated as end device. Not sure but that's the resolution in case anyone else has the same problem.
Thank you for you response!