I don't really have a time frame of when you'll be able to stroke again. That really depends on you and how determined you are to be a good boy. This could all be a smooth transition where you learn your place immediately. However, some chastity slaves take a bit longer to break in. Are you a fighter? Will you put up a struggle while being tamed or is your soul already broken and you're just looking for a mistress to steer your life in the right direction?