How Do You Redeem Yourself With A Keyholder?

I've been in LDR s but this is not a situation I ever found myself in

I think it rather depands on the dynamic of your realtionship and the nature of your chaste male.

More time locked or denial period extended are the immediate go to reponses I am however convinced you might want to see a little more imagination being employed.
I can think of some examples;
I've know of some being sent to a small shop to purchase condoms, lube the largest cucumber in the shop and a ready meal for one and a can of beer.
The inference of a night in for one would not be missed by many observers.
Others being sent to by articles of womens clothing from shops in which a measuring service is offered.
Being told to get a heavy sunbed (or garden) tan whilst wearing a bra then having to take selfies whilst sunbathing in a busy local park.
.
Without knowing you both well it is difficult to offer appropriate advice, but good luck with it..

Your chaste male ought to be, or made to be, appreciative of the effort you are going to on his behalf.

 

I hesitate to tell any Mistress how to do what she does but I know what would work with me. The threat of the removal of your services as a keyholder should he make a second error of submission should be made absolutely clear. And while the arrangement is obviously there to facilitate a fantasy, the reality of what is being done should be made implicit.

I have only recently become aware of how online Keyholders interact with their submissives but a more strict regime would be a start. Writing exercises, strict exercise regimes, some way of training that takes the emphasis away from the penis. Insist that he join a voluntary group and spend a few hours a week thinking of others rather than himself.

He needs to focus more on the reasons for what he is doing and the service you provide, and why his penis is locked up, rather than focusing on his locked up penis.

 

From my humble experience of chastity stories reader, a redeem experience is usually an occasion to go farther in the relation you live.
Unlike cheating which appeal strong discipline, the reaction after a redeem should be a positive one.
For exemple, for a beguiner in chastity and feminisation, you can say:
"Ok, I understand you! You was too horny and unlock yourself for wanking. I'll help you to master your arousal."
Then you can give him choice (start to wear panties at work too or buy a small dildo to train you at riding) he can choose his path even if at the end the goal is the same!

 

30 minutes in a kali's teeth device while watching porn