Where I worked once, the office manager, a nice enough looking blonde woman, was charity arrested at work. The idea was that her friends and family would "donate" to this charitable cause in order to make her bail and set her free. They handcuffed her and put her into the back of the police car right from the office on a Friday, and I assumed that they had also put her into a holding cell once at the station, but I don't know that part to be sure. I believe she had several "one calls" to help her finance her release, after meeting her charity donation "bail," but the concept was very kinky to me.
Was this to take place over the entire weekend? I don't remember that part either, but such would seem like the ultimate kinky scenario, and your story reminded me of this real life little adventure that I had completely forgotten about. I wonder if there is a business opportunity in there someplace? Fine upstanding citizens getting arrested for the weekend, or even the entire length of their vacation, either strapped down in a padded holding cell, or just a jail cell. I could also imagine certain liberties being allowed as a condition of their "sentence."
Just some random thoughts, and thanks for sharing your fun story, Jackie.