It should trigger a few days after you successfully capture the "friend" and give it to Lorraine. Either Caleb or Hilda will call you over in the morning.
I went back a few saves and captured the "friend" this time and unlocked the option "Submit to the "friend"" with Lorraine but then nothing happens.
Once you've seen the "double" scene with Lorraine that's it for that quest for now.
