After 3 long weeks of wearing my anal plug all day long I reached the end of the month and was allowed to go unplugged. It was extremely difficult to wear the plug all day long, but I knew it pleased Ms Lee, so I endured.

I am always anxious to find ways to please Ms Lee. It seems that constantly being in extended chastity has instilled in me a very deep seated need to please her. On the surface, this would seem to be because I depend on her to determine when I am allowed sexual pleasure. But as I think about it, I realize that Ms Lee’s pleasure has become my own vicariously.  Pleasing her provides me with a strong sense of satisfaction and contentment.

Shortly after my ‘unplugging’, I sent Ms Lee this message regarding my experience:

Today is my second day without wearing my plug. I have to admit that I do miss it, although it is an incredible relief to no longer have to wear it all day long. At times it was quite exciting and enjoyable, and at those times I couldn’t get enough of grinding and rubbing on the plug. I would get so sexually excited and my penis would strain like crazy against my chastity sleeve. It was such an incredibly frustrating tease to be able to sexually excite myself, but be denied the pleasure of a release. I would just keep grinding and gyrating like crazy, thinking all the time of the awesome control you have over me and my sexuality. I absolutely thrill to be in submission to you and I thank you for having me. I do hope that my recent essay was pleasing to you and that you will consider keeping me on. I am now back on my knees, begging you to allow me to continue to be your faithful boy.

As exciting and sexually pleasing as wearing the plug was, it was also extremely uncomfortable at times and frankly quite inconvenient. Some times no matter how much extra lube I might use I could still feel a burning sensation that was very hard to endure. I also had to struggle at times with trying to walk and sit normally while stretched by the plug. In fact I am now back on my knees begging you to only have me plugged infrequently because it was such an effort and struggle. However, no matter how painful or difficult it was at times I was determined to complete the month for you, plugged, chastised and pantied because I wanted to please you and demonstrate my obedience and devotion.

I am also concerned that the constant plug wearing may have permanently stretched my rear. I do know that it steadily became easier to slide it in and I felt less and less stretched as time went by. I was thankful to hear that you didn’t think my penis would shrink from daily chastity, but I am certain that I have been stretched by the plug.

I also began to truly crave the sexual pleasure the plug was providing me. I get quite desperate for sexual stimulation when I am in extended chastity for you and I found that I could always excite myself by grinding on the plug. It was almost like I was allowed to masturbate again, but with no possibility of a release. Naturally this combination was incredibly frustrating, but I do think I was becoming addicted to the pleasure of the plug. I know I miss it right now. I can feel my penis straining against my sleeve and my rear feels empty as I gyrate uselessly in frustration. Are you trying to transfer my center of sexual focus from my penis to my prostate? If so, I think you may be succeeding!

I am also teased by the silky smoothness of the pink panties I recently purchased at Macys. The panties tease me just as the plug did, but they do not provide me the sort of sexual pleasure that rubbing against my prostate did. By the way, I am going back to NY next Wednesday and I’ll have a chance to go shopping at Macy’s again. Do you have any particular color or style of panties that you would like me to shop for?

Chastised & pantied for your pleasure,
In my 32nd day of chastity,
and 50 days since my last pleasurable release

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