Just started getting serious about chastity over the last few months or so. My Mistress started my training off slowly. First lock-up was 3 days then 5, 10, 12 and the most was 14 days. 2 weekends ago we had a very intense evening. I was set to receive a severe beating for months of infractions as well as a blow up I had toward her at work. The punishment I took was painful but she still had compassion for me even thought I didn't deserve it at all. She ended the even giving me a hard ass fucking with her 9" cock. I remained locked during all of this and it was quite excruciating. My poor pathetic little dick bulged out of every crevice of my jailhouse cage. She did allow me to remove the cage later in the night for a cleaning as well as a huge release which conveniently landed in my mouth. Mistress granted me 2 days of freedom before my next lock-up. I am now 10 days in and something feels different this time. In the past I've had quite a bit of discomfort from pinching around the scrotum both during the day and even more at night. So far I have had none of that at all. I even had a baseball game earlier in the week where I did a ton of running and didn't even know I was wearing it. During the night I have only gotten up to pee once a night which was far better than in the past. Last night I actually slept through the night for the first time! I've read much about how the body would eventually get use to being in chastity and it seems I'm finally getting there. Mistress has decided to keep me locked for 30 days this time due to my comfort level and for that I do believe I'm finally in my happy place!
Congratulations on your acclimation. I went through a similar break-in. Now my jailbird feels like it's part of me.
I know all too well how you adjust to being locked up. For me it is no big deal anymore. Just something I wear every day like my wedding ring and Apple Watch. Good for you. I took me much longer to get used to 24/7 wear.