Preferring chastity over masturbation

Recently Ms Lee instructed me to begin masturbating daily after nearly setting a new chastity record for her. I had been in chastity for 39 days, just one day shy of my record, when she told me that she expected me to begin producing for her on a daily basis.

I had mixed feelings at first since I was so close to setting a new chastity record. Instead of the satisfaction of establishing a new record,  my intensely long period of frustration was just one more routine demonstration of her control over me.

I also quickly learned that daily masturbation is not so much fun after being acclimated to such long periods of chastity. My hormones are on a wild roller coaster ride and they quickly crashed once I began producing regularly. My first few daily productions were quite satisfying, but then it began to get more difficult to get excited and hard.  It was no longer fun to masturbate, but I knew Ms Lee expected me to continue without fail.

This was quite unlike my days when I was an uncontrolled, compulsive masturbator. I believe Ms Lee has conditioned me to expect extremely long periods of chastity and has modified my hormonal swings. I no longer seem to have the physical ability to produce daily and enjoy it. My ‘normal’ state is now chastity and I only feel satisfied and complete when I am in chastity for the pleasure of Ms Lee.

After a week of daily masturbation I was actually dreading my daily attempts to produce. There was no joy left in masturbation, it had become a difficult chore. Ms Lee had established her clear control over my sexual function and I was quite relieved when she instructed me to go back into chastity for her.

I have been thinking about this quite a bit lately because it is such a reversal of my previous attitudes. And I can now state that I truly do prefer being in chastity for Ms Lee over being an uncontrolled, compulsive masturbator.

My Mistress chooses my punishment

Although my mistress told me she would choose ‘one’ punishment from among the options I sent her, she decided to pick two. I was shocked at first, but then realized I should be happy she didn’t pick them all. Here is her response:

boy,

I prefer both options 1 and 2 below.  Beginning immediately.  Kind of reminiscent of choosing your own switch for the spanking as a kid, isn’t it?

Ms Lee

I can’t begin to express how difficult and painful it was to have to administer my own whipping. It was very hard to strike myself with enough force to leave visible marks, but I knew Ms Lee would not be satisfied until I did so. Once my rear was suitably punished I then had to insert my anal plug that I was to wear all day. Needless to say, it was very painful to sit down for the rest of the day.

Which Punishment Will my Mistress Choose?

Recently I have been extremely busy with business trips to New York city as well as ungodly amounts of work at the office and various issues at home. As a result, I started to slack off a bit on my devotions to my Mistress. I was not devoting a suitable amount of effort to her pleasure and was certainly not satisfying her. When I realized this I asked her if there was some way I could make amends.

Ms Lee was kind enough to entertain this request and told me to suggest some punishments for myself. She told me she would then choose one for me. This put me in quite a quandry since I did not want to disappoint her with suggestions for extremely mild punishments, but at the same time I was afraid to suggest anything too severe. I finally compromised by providing her with five options, some much more severe than others. This way she could determine the appropriate level of discipline I deserved.

Here are the five options I provided her with. Please feel free to provide comments regarding which punishment  you think she chose for me:

1) On the days when I do not have time to perform & report on my Worship, wear a small anal plug all day long.

2) Whip my own rear end with my belt until there are visible marks, then send you a photo of the result.

3) Finish making my Cock Trap and wear it all day on the days when I do not have time to perform & report on my Worship,

4) Whip my cock with a leather shoe string until there are visible marks, then send you a photo of the result.

5) Set a new chastity record for your pleasure – a minimum of 42 days, but you would not reveal the actual number of days required for me to remain in chastity until I reached that point (I have now been in chastity 25 days for your pleasure).