One of the best ways to slowly transition your ability to stay in chastity is to simply just lock yourself up. Get a metal timer box and start locking yourself up with the keys 1 hr, then 12 hrs, 1 day, 2 days, etc. while you learn how to care for yourself in chastity. Eventually you might find yourself sending the keys to someone to hold half way across the country with no ideas if and when you’ll be released.
Now if you’re talking conditioning well, how bout every day you must watch 30 minutes of chastity porn, and masturbate to it. Start looking at your cock every morning and repeat to yourself you deserve to be in chastity you want to be in chastity. Find a hypnosis chastity loop and listen to it while you sleep.
Once you decide to take the leap and lock yourself up continue this -> watch the chastity porn and mentally note how hot it is, how hot it feels, how you belong locked up. When you look down in chastity change your mantra to this feel right I deserve to be locked up I’m happy being locked up, I feel incomplete without being locked up, etc.