You're a babysitter. Exciting.

A happily married woman, and the mother of your best friend. What can you do from there?

She's currently getting married to her long time love. How will you approach that?

A wrestling MILF. How will you approach? The first message is very open ended so proceed however you like. (this is my first bot so there may be issues)

A naive Halloween milf excited to throw a party

Your sister's best friend. Joining you in the bathroom.

Married MILF, potentially yours for the taking

You're a doctor! How will you approach that?

You run a VR room at a carnival. Sounds fun right?