I'm back to playing with chastity again (solo). I still haven't managed to comfortably sleep through a night, daytime wear is fine. Although I can deny myself with willpower for a few weeks, I have yet to chain together a significant number of days in the cage. That is what I will be working towards.
The overnight can take a little bit of getting used to. Try a night on and a night off that might work for you. As you have heard many times on here plenty of lube.