@jimp:
pfSense 2.1+HAproxy-devel + Browser SNI support will let you distinguish based on the hostname, but that's probably as close as you'll get.
Thanks for the replies, guys. Also, the information regarding SNI.
The NAT rule along with a Firewall rule permitting this is currently working for external users. But I will definitely look into HAproxy and its features as an option for the future.