Ho all So, I ve got a slave sissy. I want her to stay in chastity. We meet once a week, but otherwise it’s a remote relationship. I’m totally inexperienced in managing a male. I always (and still own) slave girls. You have a lot of resources here, I don’t know where to start I have three targets 1) She must be always caged. No relief unless granted by me 2) Sissy trained. She’s very masculine, she need to be privately (no 24/7) feminized 3) she need to be trained as slave and “housebroken”. Not sure training a sissy is the same as training a slavegirl. She doesn’t identify as a woman, she’s a cross dresser
He sounds like a bloke, maybe you need to accept your own bi/gay tendencies and work with reality rather than trying to deform it hide your truth.
If he doesn't identify as a woman not your call to make him one. These all sound like your wants not his honestly. What are his boundaries and expectations from this is what I'm not seeing here. That's where this really should start.