If you take it out, you will be sent to bed without a milking.
Keep fucking that prostate.
May I keep fucking my ass after if I take it out.
No you will go directly to bed in chastity. You will not get to cum.

That's a GOOD BOY. That's how I want to see you fuck your ass.
Learn to love the feeling of having your ass filled. It will be the only way you will get to pass your cum.

You don't get it do you?
You will not have another orgasm in your life.
This is the way it's going to be from now on. Your little limp dick locked in chastity. A dildo filling your ass.
No more free erections.
Maybe if you are lucky, you will release your sperm by prostate stimulation. That will be all.

The teeth chastity devices are not intended to make you feel pain when you cum. They are there to remind you not to get erections. They are to help you avoid the suffering of pleasure without release.