Well I figured out the problem (with one computer) for some reason on both computers cups-browsed.services was inactive/dead I restarted the services which now say active but only one computer can access the cups menu at this time.
The laptop still times out. Yesterday I disabled IPV6 under "System, Advanced, Networking" on the pf Server, I do not have an ipv6 address set for my pfbox and I also disabled the IPV6 stack on the two computers in the kernel. I really wish I could just build cups into pfsense. The printer is wireless.