I used to milk my ex wife 1-2 times a day while she was lactating. Here are some proper hand milking tips that I would like to share.

Gravity helps with hand milking. When a lactating women is hand milked while on all fours, allow her breasts to hang down over the collection container. I used a tupperware bowl for this. You can kneel at her side or have her place her hands on the floor or a chair at the end of the bed while lying face down. This will also allow her udders to hang down. Hand milking worked better for us. We had a medela lactina breastpump, but it did not work as well.

Use a thumb over forefinger techinque, milking one breast at a time. You will the foremilk first then the hindmilk last. When her breasts become softer to the touch and milk droplets come out instead of steady streams out of milk ducts, cease milking her. Pour her milk into another container such as a mason jar, using a funnel if necessary. Fridge her milk immediately for later consumption.

I enjoyed keeping a supply of wifes milk for drinking, cooking (pancakes, mashed potatoes) and in coffee.

I milked her just like a dairy cow.
Would love to hear from others who have expierence in this type of breast milking.