Although I’ve never actually been able to lock a boy up in chastity, it’s a huge interest of mine. The idea of cum denial and not letting a sub cum until I decide is very hot and an amazing amount of control.
One of my friends found a web application that can help you determine how long to lock up a boy, or lock up yourself. The app measures time in weeks, but I would start out with days, then maybe multiply the days by 2 until you’re comfortable getting up to weeks.
The app is pretty simple and could be done with some dice too.
Oh, also, if there is anyone that needs to be locked up, especially hot, muscle studs in the Seattle area… let me know.