Struggling with getting him to submit. Advice from keyholders or subs?

Longer lockup time for sure, make sure he can't slip the device for a swift one off the wrist and have one night a week that is his correction night, meaning you'll assess his behaviour for the week and if he's been an ass then he get a heavy caning session if he's been good he gets flagged a few times just to keep him in his place.

 

Remember you are in charge.A proper punishment needs to be something he doesn't like and will dread.Be firm and don't waiver.You will both be better for it

 

Any updates how is it going? What have you done that made him submit to you