Key holding is a lot of work. It is a lot of invisible work, but it is a lot of work because chastity - even though it IS about the person in chastity - is a lot about the key holder.
Have you guys talked about what he wants the key holding to look like? What are his goals with chastity? What is the fantasy here? Does he want to be rewarded for being in a cage FOR you? Does he want to work his way out of the cage? Where is his fantasy coming from?
They key to being any kind of dominant is to get into the mind of the sub. It is also the key to charging fair prices for yourself.
If the expectation is that you're going to be available for him everyday, then you must put boundaries around that. You cannot text/call me from xam-xpm. Something like that. But even then, I'd encourage you to have goals. Maybe his homework can be about self reflection, a behaviour modification he's been pushing himself towards but hasn't been able to, and chastity is one way of doing it. He can write it out, you can review it, and y'all can talk about it or y'all can just talk about it on phone/text etc. I'd probably set up a Niteflirt for that if he wants phone conversations. If he wants to exchange emails, then you have to decide how many hours in a week you want to dedicate to that and price yourself in terms of that.
The other part of this is in person meetings. What exactly is his fantasy with that? For a six week chastity, I wouldn't let him get out of his cage, but he could come to see me 2-3 times at least w/ the same price with the goal of pleasing me sexually. This can literally be anything. From writing erotica that arouses YOU to any acts that you want him to perform. Maybe you want him to draw you bubble baths and give you massages and cook for you naked. Maybe yall go to a cofeeshop as a reminder that he is in chastity. Whatever. This is a sexually charged SETTING and therefore, anything and everything is sexual. I wouldn't necessarily lower my prices for in-person meets.
At the heart of this, I hope y'all have taken the time to really talk what lies at the heart of his fantasy and what are his goals with it. Clearly, he's had sometime to think about it so he knows that it is going to be a lot of work for you. I'd draw up what those six week interactions would look like, and price it accordingly, and even invite him to "collaborate" so you both feel like you aren't getting cheated out of an experience/money.
I hope this helps! Chastity is really exciting (to me as a top anyway) and I hope it is really fun for the two of you!
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