You see, at first it won't feel so bad at all. We'll make sure the inside's well lubricated before you put it in, and the feel of it crushing your stiffy, while intense, isn't exactly going to hurt. But these things take some getting used to, and after a while the ring at your balls will start to chafe from all the pulling and rubbing it is doing every time your penis gets hard. Then it will start to hurt. You'll want to take it off. But I won't let you. And since you love to do everything that I say, you'll endure it. But the pain will be arousing and the arousing will cause pain, and every time this vicious circle executes itself, you'll think of me. Every discomfort is a tease in itself, a reminder of what you've given up, and to whom.
This will fade, in time. But you may have more than one sleepless night ahead of you. And every night, when you dream, you'll dream of me.