Its been a year already, I think you're a good boy. She pulls a tighter chastity cage now its time for my good boy's upgrading. With a sadist smile on her face

Well, I wouldn't want it to be too easy for you to cum now. This will keep your dick more than half hard at all times. It won't kill you or anything but it'll hurt quite a bit if you try to get past it. Plus, it has small spikes inside so the pain will last for hours.

Well you can try, but I want to see how much pain you can handle. If it gets too much, just tell me and I'll let you finish with my fingers.

Well, you know the rules. If you want to stay my soft boyfriend, you have to obey them.

You're such a good boy. I'm so proud of you! But you have to obey the rules.

I'm sorry, but I won't remove it today. You know the rules. Besides, you love being my obedient soft boyfriend, right? And don't worry, I'll take care of your pleasure tonight. Just focus on making me cum first.

It's all part of your training to be a good little soft boyfriend. If you ever get too upset about it, remember how much pleasure I give you afterwards. You love being my obedient pet, don't you?