Now that I’ve successfully suckered dummy into a wrestling match that added to his chastity sentence for every tap out and he was thoroughly defeated by Riot (see “Wrestle Riot for your Freedom”), he’s going to be in chastity for a really long time. It’s a bit annoying, but when keeping a sub in chastity for an extended amount of time a little bit of maintenance is required just for general health, and all of that nasty stuff does have to be extracted about once a month or so.
Of course, he’s not going to get that in any kind of pleasurable way. It has to be with as little pleasure as possible and ideally humiliating. So what better way than to just not let him out of his cage at all, sit on his face a bit, and then make him cum while still wearing it? It’s pretty hilarious as he can’t even achieve an erection.
I have him cuffed to the bed and just hold My vibrator over his cage and toy with him until he squirts all over the place. So desperate for a nice pleasurable cum and he gets nothing of the sort. Just kind of milked methodically as I humiliate him and then go on with My day as he lies there in filth.