Oh this kind of message makes me so happy! You’re going to have so much fun!
Okay so first, don’t take anything too seriously at first. Just have fun with it. Laugh about it, be cute, tell him how excited you are. Don’t try and lock him in for days to begin with. Just get him into it a few hours before bedtime, flirt your fucking socks off once he’s locked up and drive him crazy when you get to bed.
Depending how he goes you can either let him cum at the end of that first session or just let him out, but don’t expect to keep him in overnight, that takes much longer to get used to and will immediately turn it negative (his nighttime erections will HURT).
Again, depending on how you feel it’s going slowly extend his time in it, go from a few hours to a day, and then overnight. It’ll take time for him to adjust to it. In the meantime work on your teasing skills, there’s endless inspiration on tumblr!
Speaking of which, make sure you set up a shared, private blog on here that you can both post to, and make sure you’re putting at least few hot things on there every day! You can choose to save them to drafts instead of post them, so I’ll sit down and find a whole load and save them as drafts and then when I want to there’s loads there waiting for me to post instead.
You need to play with being a bit meaner and more demanding too. Meaner because it’s just so hot for them when we are – so stuff like NOT letting him out, NOT letting him cum, ruining instead of cumming etc.
And more demanding as in you need to learn it’s okay to just let him go down on you and make you cum, a lot! On top of that, our other favourite toy is the strap on dildo which is just amazing to get fucked with so I’d suggest you invest in one of those too if you find it’s all going well.
Oh one last tip is safewords – this was hubby’s suggestion (he’s actually the expert in all things kinky). They are really useful for chastity, not because he might have to communicate how much pain he’s in – he can just tell me that and I’d take him seriously. No, safewords are about how genuinely desperate he is to get out of a cage or cum. If he was to use ‘red’ then I’d listen and let him out no matter what. Why’s this important, because him NOT saying red is HUGELY reassuring to me that when he whines and complains and wants to get out he’s actually loving it, or at least is okay. So I don’t keep worrying if I’m being too mean. Which honestly is pretty hard anyway…
So yes, I hope those are useful! Happy to help if you have any more questions!