A few Questions about Milking

I'm trying to solidify my ideas for the progression of Arc 6.  I was wondering if there is anyone out there with enough experience with prostate milking that might be able to answer some questions for me.  I don't want to spoil it before I write it but I want to make sure something is logistically possible before I try to write it and this is beyond my scope of experience.

If there is anyone who might be able to answer some questions on this subject via email I would appreciate it a lot.

Thanks in advance.