For many male subs and their Doms, the symbolism of a male chastity device is what matters most, not its inescapability. And as with other forms of sex play and most aspects of healthy relationships, the honor system makes it work.
As in any negotiated relationship, you can cheat, But why cheat? They’re easy to keep on if you’re genuinely interested in submitting.
Fun fact: locking a guy’s cock in an inescapable device doesn’t prevent him from coming.
A device can be locked in place with a belt or a piercing, but orgasms are still possible. I’ve yet to discover any kind of device that can prevent the wearer from achieving orgasm if he’s holding a powerful wand massager against it, especially after weeks without coming.