Traveling with Your Device: Vacation Advice and More Questions

I’ve been in chastity for less than a week now. My wife is surprisingly more into it, which works out well. The longest stretch I’ve managed so far has been two consecutive nights, and the pain at night has improved thanks to A&D ointment. Lately, my base ring seems to slide down, exposing the top part of my shaft; if I really want to, I can pull free. This makes me think maybe I need a smaller ring? I’m currently waiting for some sizing rings to arrive. Next week I’m heading off on vacation. Do you keep your device on while traveling? I have concerns about getting through airports and security with it in place. Also, how does the feeling change after being locked up longer? Does frustration increase or decrease? Thanks