Not sure the exact conditions to get the "handsome college professor", but I found him in my playthrough with Fawn and thus Cassie's routes complete, Male Partners enabled and with the medical class in Upper New Ark's college taken. He's at the college.
MPreg, no clue, but Cumflation is received by losing to the Infected Scientist in the infested Science Lab Tower. There is a single Trap, and you can find him by working as a bouncer in the New Ark nightclub, the Rock. He has a random chance of appearing, I think.