Stroke it
Let him watch you stroke your cock before giving it to him. It will remind him of the simple things he can no longer do, and prove yet again that you control any stroking.
Inviting a friend?
Inviting a friend?!? At first, I thought, "never!" But training is a good thing, and the humiliation brought on by inviting a second friend in on this is a new paradigm. The devotion to you and respect, not knowing what might come next, is unreal.
Lace power
Never underestimate the immense power of your body and a sexy bra to get just about anything you want from a man.
Training and attention
Men, your chastity should give you the time and motivation to get really good at pleasing your mistress. Learn techniques to give a REAL massage. Failure to do so... Well, just get really good at it!
Man’s place
Men, know your place. It is beneath your woman, your mistress.
Your friends
Whether you choose to tell your friends about your chastity arrangement or not is irrelevant. His wondering about how much they know is a great thrill and tease. Make sure you wear your key on a necklace to add to the thrill
Mantra
Make him repeat this often. Making him do this while you are topless works wonders for his motivation. Punish him for dropping his gaze to your breasts without permission
Tongue tracing
improve his Tongue strength and creativity by making him trace letters with his Tongue pressed against your pussy. For example, trace, "yes Mistress". Find phrases that are especially pleasurable, and Make Longer phrases, to keep him busy. Don't forget to discipline, if he's not doing it perfectly. :)
Strap-on sex
Keep him in chastity while letting him wear a strap on. His attention Will not be on his release, but your orgasm. The teasing is delightful! The humiliation of him feeling the same motions, but using a substitute tool is beautiful
Beg for more
Make him beg for more chastity. That makes it his choice, even though you really control the release. The real choice is not the duration... It's the submission to your desires