I'm not going to go into the legality of it and whatnot, I'm just going to give some suggestions that occured:

If you really want to make him feel the sting of this situation and not just the kinkiness, order him to do something which is slightly more public or which has a risk of arousing suspicion. Not something huge that will scare him away, but something which might be a little intimidating for him. For example, maybe have him do some minor C&BT whilst in the restroom at work then bring himself to orgasm (with pictorial evidence, of course).

Perhaps also you should make it so that he has to check in with you via e-mail on a very regular basis, such as once every 12 hours or once per day. If he cannot make one of these appointments then he has to contact you beforehand requesting very specific permission to do so. Make it clear that if he is ever late with a 'report' without your permission then you will use whatever leverage it is you hold. This will mean that he very quickly gets used to the idea of being under your complete control, and will be unable to plan any event without considering how it will affect his relationship with you.