Play safe and realize that having fun is not a sin.
To play successfully you need to begin with a strong 1-1 bond and be able to talk openly and honestly to each other.
If it was meant to be a one time offer, that's what it needs to stay.
What was his rationale for allowing this? One minute they're at each other's throats during that dinner in Ojai when told to and then the next, they're laughing and doing cartwheels together in the bedroom.