Natescage does it scare you that that is the case with you mom and his mom? Seeing as he may want that for you I would be scared some about that.
I know that I have to continue wear my chastity belt and my chastity bra but not my tightbands. Both will stay in place all the time for good and will only be opened for cleaning and when he wants us to play with eachother. I will also often give him pleasure without being opened myself. I know it is manageable but far away from easy. Because it is consensual it is much easier, but I think that it will still be very frustrating.