I usually wear a cage for two weeks or more at a time. The longest I have went is 31 days in a row.

So far I have not been able to cum wearing the cage. But, I have not tried to masturbate wearing this cage. I probably could orgasm if I tried hard enough but that would defeat the purpose of wearing it.
Right now, I am working towards my first anal only orgasm. I have been trying since my last full orgasm on November 10th.