While posting comments on a different blog's post about chastity it triggered a memory about a discussion on long-term chastity that F and I had with a local couple years ago. I didn't really feel like it was something that fit into my comments so I figured I would post it here.
F was friends with a couple in the local scene that regularly engaged in long-term chastity (6+ months). As of that time if I remember correctly, the longest the had gone is 2 years with the "standard duration" they were now going with being 6 months without a release. We didn't really get all in depth about maintenance (milking, hygiene, etc.) but F was very interested in the process.
After his release and orgasm, they would go 2-4 weeks before starting again. Over that time, he was "encouraged" to masturbate frequently and orgasm multiple times a day, with the final week before being locked up again involving 6-12 orgasms a day. This didn't make a lot of sense to me until she explained it more in depth.
As she put it, the more frequently a male orgasms, the more semen his body will produce. Upon getting accustomed to a regular orgasm schedule, the body will soon begin to produce enough semen to fuel those orgasms. Gradually increasing the intensity of the orgasm schedule would then condition his body to produce greater and greater amounts.
Upon locking him up, his orgasms would come to an abrupt halt, but his body would continue to produce semen expecting the same number of orgasms as before. The end result of this method was a jarring and intense sense of desperation upon being locked up that far exceeded the "1 orgasm and locked back up" method.
The prep work that went into increasing the physical and psychological jolt of the fresh chastity period was quite interesting.