Let's start with your second part ...
i hope you sucked with full effort ... *giggle*
At first say 10 times: "Thank you for this awesome experience, miss Lane".
Fix your dildo at a position, so you can fuck it, while you are on your knees ...
You know what i want ...
Slide out your plug and start to rub your asshole on the (hopefully it is wet *giggle*) head of the dick ...
you can start to stroke ...
Ah i think it is a good idea, if you put a plate under your sissy dick to gather some precum ...