Hey! Thank you for your feedback. After considering the path, you suggested (getting blackmailed by Sarah or Monique and getting "punished" by Chloe) sounds like an exciting path, and we will add it in a future update.
To answer your question, to work for Chloe, you will need to choose "I like being humiliated (Extreme content)" in the menu while you are f*cking her. Going on that path will open the option to work for her. You can check the walkthrough for that option if you don't find it.
If you need further assistance, please join us on discord here: https://discord.com/invite/HqaQ7uS
Enjoy!