Milking

Milk him on a regular basis. When milking him, make him assume the same posture on all fours with device on (if you do a prostate stimulated milking), or without the chastity device if you do a hand stimulated milking.  Be sure to use large rubber kitchen gloves and try to make it as unexciting of an experience as possible.  Be sure to position an ice cube tray below to catch all the milk that can be frozen for future purposes.