How often have you sent a guy home in chastity, either that he expected or did not expect?

I did this often in NYC, always negotiated, and for a day up to a week's time. Funny story: as this was the early days of chastity, there was only the CB2000 on the market, which didn't always fit so well. On the metro from my dungeon, the sub's device slipped off down his pant leg and onto the subway floor. It was not the adventure he signed up for. Hah!

Chastity for more than a weekend can be difficult unless you are on vacation. It's really distracting at work!

If its at all worth knowing about, i cannot say enough good things about the Cherry Keeper cages. They are 3-D printed from very lightweight but sturdy material and although they no longer offer bespoke orders, one can basically select the ring diameter, shape, angle and all aspects of the cage to order. So if one can measure properly they fit like a glove.

I find this idea intriguing. Although, I think I would be more interested in pre session chastity. A brief 10 minute visit to the Domme a day or two before a session where she locks you up and sends you on your way. As an alternative she could mail you the device (without keys of course) and supervise you putting it one via video call.

I love the excitement and anticipation the builds in the hours and days leading up to a session and I imagine being locked up would only increase those feelings.

I have little experience with this so a serious question....are there devices that are secure enough that there is no way to remove them without the keys (or that would not be able to be reinstalled) and yet relatively comfortable to wear for a day or two? (I'd assume steel rather than plastic?)