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!