Port 995 is for SSL connection. You cannot do it with telnet. You could probably try OpenSSL and to test it that way.
openssl s_client -connect pop.gmail.com:995 -quiet
More info on OpenSSL for Windows is here: OpenSSL for Windows
ADDED:
I have just tested with openssl command I gave you above. It works like a charm:
user@localhost$ openssl s_client -connect pop.gmail.com:995 -quiet
depth=1 /C=US/O=Google Inc/CN=Google Internet Authority
verify error:num=20:unable to get local issuer certificate
verify return:0
+OK Gpop ready for requests from 11.11.111.11 v45pf1517914yhk.21