The fifth chain

For a few days now I have been enduring an extremely tight fifth chastity chain that I have attached to my chastity sleeve. This new chain is quite painful at times, stinging as is bites into my firmly restrained penis. However, as I explain below, I feel this increased level of chastity control is necessary and will insure that I adhere faithfully to Ms Lee’s no touching rule.

Here is the message I sent to Ms Lee explaining why I felt I needed the additional chain:

I hate to bother you again and risk annoying you with my trivial frustrations, but I feel I should let you know that my level of desperation is reaching even more incredible heights. For a year now I have been experiencing extended chastity periods and my level of frustration is nearly unbearable. My penis seems extra sensitive now and my panties are teasing it like crazy. I can’t stop straining against my sleeve and I frequently find myself grinding my rear against my seat. As you expected, I have not been using my anal dildo or plug during Worship and my rear is feeling quite neglected.

I have been so desperate lately that I have been worried that I might be tempted to touch myself again. I can’t conceive of disappointing you in such a way so for now I have added a fifth chastity chain to my sleeve. The four I normally use have allowed my penis to become partially erect between the chains which is driving me crazy with sexual desire. The partial erections result in my poor penis looking like some kind of restrained sausage and they are quite distracting.

To more firmly restrict my naughty penis I used one of those milking chains I had fashioned previously. It is a couple of links shorter than my normal chastity chains and digs in quite painfully whenever my misbehaving penis attempts a partial erection. I secured it at the end of my penis, right behind the head. So far I have found this addition to my chastity to be quite effective, with the tempting partial erections now eradicated (although my penis continues to strain frequently against the chastity chains). My penis is now very firmly restrained and in full submission to your will. I will continue to wear this fifth chastity chain until you tell me otherwise.

Administering my punishment

As I read the punishment program that Ms Lee had laid out for me I realized just how badly I had disappointed her. Although I had thought my transgression was only a mild breaking of her rules, it was obvious that she would tolerate no disobedience. She clearly intended to give me a clear, firm reminder of just who was in charge of my sexuality. I really couldn’t imagine how I could possibly endure everything she expected, but I knew that there was no alternative. I am completely devoted to Ms Lee and could never consider failing to meet her expectations. I immediately responded with my submission to her will:

I am on my knees apologizing again as I type this response. Of course I submit to your wishes and will obediently do as you expect. I was concerned that you would punish me for my transgression, but I never expected your punishment would be so severe. Nevertheless, I will carry out everything as you specified.

I decided it would be most appropriate if I began my punishment by dealing with the member that had caused the issue. I had marked my penis once before for Ms Lee and remembered how difficult it was to do so and this time was no different. I used the same belt and proceeded to whip my pitiful penis until it began to turn red. Like before, it was a long, painful process to get to the point where visible marks began to appear, but I knew Ms Lee would not be satisfied until my penis was properly punished. It took about a half hour of agonizing torment before I was able to inflict a sufficient level of damage. My penis was throbbing in pain, but I was hopeful that Ms Lee would approve.

Before taking photos to demonstrate to Ms Lee that my penis was marked as she expected I shaved and trimmed it and the surrounding area to make sure that my appearance would be pleasing to her. I had made the mistake of not doing so the previous time I had marked my penis for her and was shocked when she told me to trim myself properly and then whip my penis AGAIN before resubmitting new photos. I certainly did not want to repeat that mistake so I was well trimmed and shaved as I sent Ms Lee the photos of my properly punished penis:

The attached photo shows how I have marked my penis for you. I will take more photos in the morning when I have more time. I will also mark my rear for you in the morning, it took a while to get my penis marked well enough. Like the last time I did this for you, I was in so much pain that my knees were shaking by the time I was finished. My penis stings quite badly right now, but I certainly have a firm reminder that I need to always obey you and be a good boy.

In the morning I received an acknowledgement from Ms Lee, approving of the markings on my penis. I then proceeded with the next phase of my correction by marking my rear. I have previously done this for Ms Lee, but I had never been able to reach the point where it was black and blue as she expected this time. As my next message to her indicated, I knew that my initial attempt at punishing my rear was unsatisfactory:

I am so relieved that you are satisfied with my penis markings. It stings so badly that I don’t think I could bear to strike it again. I have attached another photo of it showing how the markings are deepening.

I spent at least an hour altogether this morning beating my rear with my belt, but even though my knees are shaking again from the pain I know I have not achieved the color you expect my rear to become. It is getting red right now, with the belt markings showing, but I haven’t been able to hit myself hard enough yet to get it black & blue.

I will continue punishing my rear until you are satisfied with the color. I may not be able to do this again until tomorrow morning however. In the meantime I just wanted to send you the attached photos so you could see how my rear looks so far.

I have mailed another tribute to you and of course I will send another in about a week for the month of April. I am also diligently working on my essay stating the importance of obeying and being a good boy.

The next morning I proceeded to whip my rear again. I had received no reply from Ms Lee which I assumed meant she was not yet satisfied. After another long, painful round of self inflicted punishment my rear finally looked colorful enough that it might meet with Ms Lee’s approval. It was unbelievably difficult to whip myself that hard, but I knew I had earned this punishment and needed to learn my lesson. I then took some more photos and reported to Ms Lee:

Attached are some photos of my properly punished rear. It took another half hour of whipping my rear as hard as I could to get a proper color. My rear stings badly now and is bleeding a bit in some spots. I sincerely hope that you will be satisfied with my efforts. I certainly will have a reminder of why i should not disobey you whenever I sit down, for quite some time.

I then proceeded to complete my essay on The Importance of Obeying and Being a Good Boy. It took five days of intense effort to write a properly crafted essay of 1,500 words as Ms Lee expected. I knew that she would not approve of a sloppy, poorly written document so I put a lot of effort and devotion into writing a proper essay. Instead of being an ordeal, I actually found writing it therapeutic and it helped to cement in my mind my proper role and behavior. I was able to complete it by Ms Lee’s deadline and then sent it to her to complete my punishment.

A just punishment

Recently Ms Lee gave me a very firm reminder that I must always be a good, obedient boy for her. My lesson began when I briefly lost control of myself and allowed my pigmale desires to get the better of me. One morning during Worship I was so frustrated and desperate that I found myself lightly rubbing my penis. It was futile since I was wearing my chastity sleeve and I stopped when the pain of my penis throbbing against the chastity chains became too great. I then felt quite guilty and dutifully reported the event to Ms Lee. I expected her to be disappointed with me and thought that she might punish me, but I had no idea just how severe her punishment would be. This is how I reported my transgression:

I’m glad that it does not bother you that I constantly tell you about my frustrations and desperation. It drives me crazy that you did not even respond to my begging to be allowed to wear my plug. I remember how deviously pleasurable it was to experience the plug filling my rear and teasing my penis so much that it would strain uselessly against my chastity sleeve. It frustrated me badly, but like now I was so starved for any sort of sexual stimulation that I gladly endured the discomfort.

This morning I once again gyrated like mad as I thrust my anal dildo in my rear as I attempted to milk myself. Once again (possibly due to recent stress) I was unable to produce anything more than a slight dribble. And right now I am on my knees begging you for forgiveness because during this morning’s session I gave into temptation and touched myself while using my anal dildo. I did not masturbate, but I did rub myself with a couple of fingers. I had to stop when the pain of my chastity chains digging into my penis became too much, but I feel quite guilty about this wanton behavior ( I don’t use my sleeve to protect my penis while milking myself and it doesn’t usually get too hard then anyway, the focus is on my rear and prostate).

I am now safely in my sleeve (and chains), but I continue to squirm in my seat in desperation while my rear clenches against emptiness. I am so frustrated, and so sorry if I disappointed you.

In my 46th day of chastity for your pleasure,
Wearing my first pair of purple panties today.

Ms Lee’s displeasure with me was quite clear in her response:

I am very disappointed.  In all the months and years we’ve known each other, you’ve not disobeyed me.  I am not happy about being put into this position.  Do the following and respond to this email acknowledging your submission to my wishes:

(1) 1500 word essay stating the importance of obeying and being a good boy.  Due Tuesday night, absolutely no extensions or exceptions.

 

(2) Send another tribute, immediately.

 

(3) Punish your rear and your penis with a tool of your choice.  I want your rear black and blue and your penis very well-striped.  Send pictures and I will let you know if sufficient.

 

(4) No touching, no plug for morning worship, just chastity, until I tell you otherwise.

 

Begging to be plugged

During the past six months Ms Lee has granted me three pleasurable orgasms, the last one being about six weeks ago. During this dry spell I have learned to appreciate the teasing pleasure that anal stimulation provides me with. Ms Lee is very generous in allowing me to use my anal dildo every morning so i can milk myself when the pressure becomes too great. Rubbing the dildo against my prostate is nowhere near as pleasurable as masturbating my penis, but I have given up expecting that experience. I know now that Ms Lee only allows it on rare occasions, usually on a whim, just to remind me what it is that I am missing. Of course this reminder of her control over me binds me ever more closely to her will.

While I enjoy my morning sessions with my anal dildo, I find myself yearning for some sort of sexual stimulation during the day. As my current chastity period extends well into the second month my focus centers on my rear, clenching against nothing in a pathetic attempt to excite myself. I realize that I am missing the sensation of my anal plug pressing against my prostate.

It has been a month now since Ms Lee allowed me to be unplugged, after enduring two straight months of being plugged on a daily basis. Being plugged every day was quite difficult and uncomfortable, but I have to admit that at times I greatly enjoyed the sensation of the plug pressing on my prostate. I would certainly not want to return to being plugged daily on a continuous basis, but it would be quite pleasurable to feel my plug fill my greedy rear for a single day or so.

With that thought in mind am on my knees, begging Ms Lee to please consider allowing me to use my anal plug for a short time. I would love to wear it for a day or so, but I desperately hope I would not have to begin another lengthy period of being plugged daily.