Ok, this is where I tell you I've been locked up for months with no orgasms and no "milking." Uh... no. Maybe one day.
The truth is that my last orgasm was on Sept. 9th. Two days later, in the heat of passion I agreed to not cum again for three weeks. And so far, that's the way it's been, even though I'm only in the device about 50% of the time, due to sores developing and such. Chastity without a device is just not very compelling. I freely admit I have a chastity device fetish.
I've definitely not gone this long without an orgasm since I hit puberty. Surprisingly, for a guy who usually wanks once or twice a day, it's been easier than I thought. I haven't felt that burning desperate desire to cum. At around 10 or 14 days I definitely wanted to, but it wasn't all that desperate. I wonder how long would it take?