Mrs. Lion has said that when I make suggestions it makes her think she is failing as my keyholder. We discussed that and I think she understands that I am, by nature, an experimenter and that my suggestions are just my attempt to see how something different might feel. That conversation got me thinking about the keyholder experience in broader terms.

Mrs. Lion agreed to be a keyholder to make me happy. She knows that I have that particular kink (among others) of wanting her to control me sexually and being locked up in a chastity device helps me feel her control. So she locked me up. Since then we have been feeling our way through building a long-term chastity lifestyle. Since her purpose was to make me happy, she measures her success by how happy I am with her performance as my keyholder.

The problem with this measure of success is how to define “making me happy”. This is a problem I had when I was a practicing top. My role was to control and discipline the bottom. In a session that lasted an evening, it was easy to get feedback when the scene was done. That feedback provided me with a measure of my success. However, when I was in a 24/7 top role, it was very hard to know how well I was doing.

Since part of Mrs. Lion’s role as keyholder is to make me wait for my orgasms, and waiting makes me grumpy and sometimes unhappy, how does she know she is successful? More importantly, what can she use to get satisfaction for a job well done?

One way, of course, is to ask me how she is doing. She finds asking that kind of question very difficult. I can and do tell her frequently that I am very happy she is my keyholder. I thank her for her work to indulge my kink. I am sure this helps. But it isn’t easy to remember to do this enough. For me it means stepping out of my caged male role to thank her for doing things to me that I don’t like. For her, there is the obvious contrast between my thanks and the grumpiness and expressions of pain and discomfort I give when she spanks me or does other things that obviously hurt me.

In the BDSM world it is considered good manners to thank the top each time he or she inflicts pain or other sensation. These thanks, while ritual, do provide positive feedback that helps give satisfaction to the top. It’s more difficult in enforced chastity. For one thing, it goes on continuously. I am locked up full time. When I finally get my orgasms, there is always the knowledge that I will have to wait a long time for the next one. There is no logical start or finish to our activities.

So what is Mrs. Lion to do in order to measure her success? The standard answer is that she should enjoy the extra sexual satisfaction she gets as a result of locking me up. I don’t think that makes a bit of sense. As her mate, I should have always given her all the sexual satisfaction she wants. She shouldn’t have to force me to do this by sexual domination. So, that won’t fly. No way!

Mrs. Lion tends toward inaction. It’s her nature. Even if some activity is very satisfying she still won’t actively pursue it. She needs a better reason than her own pleasure to be active. Pleasing me is a strong motivator for her. I’m grateful for that. But in order for that motivation to work, she has to know that she is actually pleasing me. Giving me orgasms is to both of us, a clear message she is pleasing me. But now we are engaged in an activity where not giving me orgasms is the main idea. I think she has alluded to this in many of her previous posts. She says that she loves giving me orgasms. If we look at the flip side of that statement, it means that she doesn’t love not giving me orgasms. Our enforced chastity has removed one of her primary motivators to do things sexual with me.

Similarly, some of the things I want her to do (that may have nothing to do with chastity) like spanking me and disciplining me, obviously make me unhappy. So now we live in a topsy-turvy world where it is good to deprive me of sexual satisfaction and good to inflict some physical pain. Intellectually she knows that this is exactly what I want and her doing all this makes me a happy and contented male. But it is very difficult for her to get satisfaction out of doing these things.

I have a few ideas that might help. They may allow her to find satisfaction in the same things that actually make me happy. Admittedly, these ideas involve an intellectual process instead of an emotional one, but they may give her a concrete way to gauge how well she is doing.

  • Keep track of what you have done. Count and make notes about each teasing session. How many times did you bring me to the edge? If you wanted to, did you ruin an orgasm? If you had an accidental ruined orgasm, how many times did you edge me before it happened? This will let you see your progress over time. Record each of my wait times. Note how you have increased my waits. Note my behavior changes and how you managed them. I know that you already understand them, but by taking notes you can later see how you have improved your control.
  • Track how you have managed me outside of sexual satisfaction. Each time you note an infraction, record how you handled it. You could use your Naughty Lion coupons for this. Even if you choose not to punish, by tracking infractions you measure how your ability to manage me is going. You can also note each rule you decide to enforce. Again, since you know that this is something that makes me happy.
  • Track punishments, fun or real. Since you know I love to hate punishments, noting when and what you do can let you measure how you have grown in that area.

I realize that tracking things is extra work, but with the computer tools we have, it is pretty simple. My point is not to tell Mrs. Lion what to do. It’s to offer ways to measure success. What do you think, Mrs. Lion?