Archive for the ‘Punishment’ Category

Ms Lee relieves my frustration

February 20, 2016

Ms Lee still has not allowed me a release this year and my frustration has been getting worse by the day. I hesitate to mention my frustration to her because I don’t want to sound like I am begging for relief. I know she enjoys having me endure lengthy periods of chastity and as I mentioned in my previous blog entry I consider my chastity to be a gift that I offer to her. However this does not make my frustration any easier to bear and since Ms Lee always wants to know how I am feeling I have told her of my mounting frustration on occasion (she has also told me that she finds my reports of frustration to be entertaining).

Recently Ms Lee responded to one of my reports of desperate frustration and told me that it was a shame that I was struggling so much with my frustration. When I read those first few words in her response I thought that she might be about to grant me a rare release. My brief hope was quickly smashed as I read her next sentence asking me if I needed her to have me beat my unruly penis into submission so it would no longer distract me. I swear I could hear her chuckling as she finished by saying that she would be only too happy to do so.

I faced a new struggle as I considered my response to her question. I have punished my penis for her in the past and found it quite painful. However I am ashamed to admit that I found the pain perversely exciting. I know that Ms Lee does not pander to such pigmale perversions of mine but I also suspected that she would greatly enjoy seeing my penis punished for being so greedy. So I told her I would certainly punish my penis if that would please her and I was relieved when she then told me that she would not require me to inflict visible bruises.

I decided to video tape the punishment of my penis for the entertainment of Ms Lee and wound up creating three short videos. Here is a link to the video I created of my initial punishment:

Initial punishment of my unruly penis

My poor penis was already stinging by the time I finished my initial punishment but I was concerned there may have been too much shaking as I held my phone to take the video so I decided to create a second video:

More punishment for my unruly penis

My beaten penis was really hurting at this point as the repeated smacks of the wooden ruler were taking a serious toll. However I still wasn’t certain that I had managed to create an acceptable video so I created one more showing my unruly penis being put in it’s place:

Unruly penis being put in it’s place

After the third beating my penis was truly hurting and it turned out that I had inflicted a nasty looking bruise on the side of my penis where the ruler punished it. And it also turned out that all three videos were suitable for viewing. When I presented them to Ms Lee and told her of my bruising I expected that she might be sympathetic. I should not have been surprised when she instead just replied that she found the videos hilarious. That was not exactly the response I had been hoping for but I was very happy that she was pleased. After all, her pleasure is all that matters and I am always anxious to find a way to please her.

 

Service Oriented Submission

December 13, 2015

I have only recently become aware of the term “service oriented submission” but the more I learn about it the more I realize that it perfectly describes the type of submissive I am. Whenever I fantasize about or express my submissive tendencies I find myself drawn to thoughts of serving and pleasing my dominant partner. I have come to realize that my desire to please another is stronger than my desire to satisfy my own need for gratification. Even when I feel a desire to experience a submissive experience such as being disciplined or embarrassed I find myself needing my submission to please another in order for me to feel fulfilled. It was only when I became aware of the concept of service oriented submission that I fully realized how my need to please another drives my need for submission.

I have come across a variety of definitions of service oriented submission, for instance “A person who enjoys performing a service in a sexual or BDSM environment.”. It has also been described as “A person who derives pleasure and enjoyment from performing acts of service for another person.” I think a better description is provided by Ms. Rika, author of Uniquely Rita who says “A service-oriented dynamic is Dominant-centric. It’s not focused on what is done TO the sub, but rather on what the sub does FOR the Dominant.” She goes on to explain “Obviously, the biggest differences are that the commitment to serve is not time-bound and the activities are more oriented to service than to fetish. This is not to say fetishtic and BDSM activities do not take place, but they are not predicated by the nature of the D/s agreement.

As Ms Rita suggested, sexual service devoted to pleasing the dominant is just a part of the overall service provided. It is provided in order to complete the overall level of service but it is not the primary focus. In fact the submissive must use careful judgement and only initiate sexual service when it is clear that the dominant desires or is in the mood for sexual service. The goal is to please the dominant and make their life complete, sexual activity is only included when appropriate to make the dominant’s pleasurable life complete.

It is equally important that the submissive never expect any sexual gratification in reward for their service. The only reward the submissive expects and deserves is the pleasure and satisfaction that the dominant receives from the service provided. A smile or expression of pleasure from the dominant is the ultimate reward that the submissive seeks.

This is not to say that sexuality does not play a significant role in service oriented submission, the point is just that it is not the core concept. Service to the dominant is the core concept but sexuality can significantly enhance the experience for both the dominant and the submissive. For the dominant, sex play can become solely oriented on their own pleasure and satisfaction with no need to pander to the submissive’s sexual desires. The dominant can relax and concentrate on enjoying their own sexual pleasure without having to worry about satisfying someone else’s needs.

Sexual expression for a service oriented submissive is quite different and from my perspective serves two significant purposes. The first involves chastity and denial of sexual pleasure for the submissive. The purpose of chastity is to bind the submissive to the dominant, making the submissive dependent on the dominant for any opportunities of enjoying sexual pleasure. Being kept in prolonged chastity and denial will certainly focus the submissive on the desires of their dominant partner. I am aware that being kept in chastity, with no knowledge of when I might be allowed a release is a major motivator for me to provide excellent service.

The second purpose a service oriented submissive’s sexual expression serves is to provide a source of power and amusement to the dominant, allowing them to own the sexuality of the submissive for their own gratification. It naturally follows that the submissive would never expect or request their own sexual pleasure. Sex for the submissive revolves solely around the pleasure of the dominant. Whenever the submissive feels a sexual urge they will express it by taking action to sexually please the dominant, but only if they are certain the dominant is in the mood for sexual play.

I found Ms Rita’s explanation quite enlightening and it helped me understand that devotion to service is the primary driver for a service oriented submissive. Service oriented submission goes far beyond the usual sexual d&s relationship. It absolutely includes non-sexual service devoted to a dominant without necessarily including traditional d&s trappings. A service oriented submissive will tend to household chores and other tasks that benefit the dominant without requiring any sexual overtones or direct supervision from the dominant. The service oriented submissive is devoted full time to the service of the dominant.

It is important to note that service oriented submission is not just a one way relationship. One submissive expressed this aspect of service oriented submission very well when they said “I am not offering a free service. I am offering service with care and devotion. In order for me to care about your task to the fullest of my ability, you need to care about me.”

A BDSM fetish that is not absolutely required as part of service oriented submission is physical discipline. Some submissives (and dominants) have a deep need for physical discipline such as spanking and caning but others may have no need or desire for it. I know that have a fetish/kink for being disciplined and that I would be better motivated and fulfilled if my service involved the knowledge that I would be punished for the smallest shortcomings. And perversely, I would also be motivated if I knew I would receive a “reward punishment” for good service.

As I think about how I envision myself in an ideal service oriented submissive role I find myself drawn to the stereotype of a 50’s era housewife, whose life is devoted solely to the gratification and pleasure of her dominant spouse. While many people today are repulsed by the degradation of women that routinely occurred in those situations I can see how a suitably submissive ‘wife’ could find fulfillment in devoting herself without reservation to the service of her spouse. I can understand how a typical 50’s era ‘wife’ appreciated the submissive joy of focusing on nothing but the pleasure and satisfaction of their spouse and gladly assumed responsibility for all the household chores. the 50’s era ‘wife’ would wake early every day, long before her spouse and happily toil away knowing that her reward at the end of the day would be a sense of accomplishment, having completed her household chores.

I think it was this revelation about how a typical 50’s era housewife could find happy fulfillment in her role as a submissive spouse that made me realize that I was what I now know is called a service oriented submissive. I find genuine pleasure and satisfaction in completing the household chores that I have found myself responsible for. I feel quite natural in the role of a ‘housewife’ taking care of my home and knowing that I am a service oriented submissive will help me find fulfillment in my life.

The return of the sleeve

June 28, 2015

I recently made a big mistake by comparing myself to other men. I had been telling Ms Lee about the unbearable frustration I have been enduring and I said that I didn’t know how much longer I could go without tasting the sexual pleasure that most men get to enjoy at their leisure. At the time I was begging Ms Lee for my weekly permission to touch myself and I realize now that I should not have compared myself to other men in regards to their sexual freedom.

When Ms Lee responded to my begging She told me that she could see that I was really beginning to suffer but she had also noticed that I had made the mistake of comparing myself to other men. She reminded me that I was her property and that meant that I didn’t compare to other men. She then informed me that the consequence was that I was to put on my chastity sleeve and not remove it until she had given me permission. She also informed me that I had squandered my weekly opportunity to touch myself and I was to wait till the next week to beg again.

I had thought that I couldn’t possibly get any more frustrated but once more Ms Lee turned my world upside down and drove me deeper into submission to her. Although not being allowed to touch myself was extremely frustrating I at least got to enjoy the feel of an unrestrained erection like a real man. But I am not a real man, I am Ms Lee’s property and now I no longer get to even enjoy erections, much less touch myself.

I had also forgotten just how difficult it was to put my chastity sleeve on. (Those who are not familiar with my chastity sleeve can check some of the past postings about it: Chastity sleeve postings).

It is a major struggle to get my sleeve on, especially since my deprived penis gets quite excited from the handling required to get it in the sleeve. Once in place my sleeve performs an extremely effective job of preventing anything approaching a full erection. And when my naughty penis does try to become erect it is severely punished by the chains holding the sleeve in place. Those chains cut in deeply whenever my penis makes a futile effort at becoming erect.

The photo below shows my penis restrained by my chastity sleeve. This is a homemade sleeve which has the advantage of being unnoticeable under my pants. The tightness of the restricting chains is also easily adjustable, a feature which Ms Lee has used to her advantage. She has at times enjoyed having me remove links to make my sleeve even tighter but she has never allowed me to add any links back once they have been removed. Anyone who is interested in how my sleeve is fashioned can check out this posting – Ms Lee’s Chastity Sleeve

You might notice in the photo below that none of my fur pokes out from beneath my panties. I have previously made the mistake of presenting myself to Ms Lee with some random hairs showing and every time She has me correct my error, removing even more. Ms Lee does not like to see any fur showing from beneath my panties so I am always carefully grooming myself. Some of my panties are fairly skimpy and at this point I have removed quite a bit.

Pantied and Chastised

My shrinking penis

August 31, 2012

Ms Lee seems to enjoy having my chastity chains severely tight. As I mentioned in a previous posting, she had me shorten them by a link each to correct me for having an unauthorized release. Initially this was to be for a period of a single week, but that was extended for another week when I asked if it would please her to extend my correction. This cycle was repeated until finally she told me that I should just extend my punishment thru the rest of the summer.

As Labor Day approached I sent her an email describing the torments that my tightened chastity chains had inflicted on me. Here is a copy of that email:

The last time I begged you to allow me to please you by extending the time I wear my tightened chastity chains you told me to do so until the end of summer. As the end of September approaches I realize that I am not sure if you consider Labor Day the end of summer, or September 21. Regardless, I am now on my knees begging you to allow me to continue enduring my viciously tightened chastity chains until the official end of summer on September 21.

Please do not grant my request unless it will please (or amuse) you. Although I have to admit that I am perversely excited by the pain of the tightened chains I can assure you that I am not enjoying my predicament. Although I have done my best not to complain to you, I am actually enduring a considerable amount of suffering. I have gladly done so because i desperately desire to please you and I am hopeful that I can continue to do so.

Below is a list of the various ways my tightened chastity chains are affecting me. Please understand that I am not complaining in any way or asking for leniency. I just want to make sure that you are aware of the full extent of what I am enduring in the hope that you might derive more pleasure from my situation.

– My penis is constantly crushed by my tightened chastity chains

– I have to sit down and pee like a girl because the chains are so tight that my pee continues to dribble out for a few minutes after I urinate

– By the end of each day my punished penis is raw and red

– At times my tightly chastised penis feels like it is being burned, I feel an intense stinging that will not quickly go away. When this happens I endure the pain by thinking about your pleasure

– Erections hurt even after I remove the chains at bedtime. The deep impressions inflicted on my poor penis continue to cause pain as if the chains were still in place

– I realize that the viciously tight chastity chains are conditioning me to prefer anal pleasure since any attempts to enjoy an erection are instantly corrected by the bite of the viciously tight chastity chains

– When my tightly chastised penis does attempt an erection it is barely able to achieve 4 inches in length. And of course it is restricted to less than an inch in thickness. This is quite humiliating and I am really beginning to wonder if my extended, severe chastity might actually be causing my inadequate penis to become even smaller than it already is

Once again I am on my knees begging you to allow me to continue enduring my tightened chastity chains. I sincerely hope it will bring you some pleasure and perhaps bring a smile to your lovely face.

In my 67th day of chastity for your pleasure,
my 67th day of enduring my shortened chastity chains,
135 days since my last pleasurable release,
and wearing my black lace panties with pink trim today

Although I would have gladly continued enduring my tightened chastity to please Ms Lee I was relieved when she told me that it would not be necessary to extend my punishment beyond Labor Day. That night as I removed my chastity chains before going to sleep I discovered that the effects of my viciously tightened chastity would continue. Here is the message I sent Ms Lee the next morning concerning this:

I hope your toes were curling in your sleep this morning as I thought about pleasing you with a long, sensuous foot massage. I would caress your lovely feet and rub each individual toe, kissing them as I moved on to the next. Before I started I would light an oil warmer so I could rub the warmth into your feet. I would also have candles lit and some of your favorite music playing to help you relax and enjoy the pampering. I would set out some plants and light some incense if you liked. I would always be trying to think of small new ways to maximize your pleasure.

I do hope you have a lovely morning and a wonderful day today.

I was also thinking of you last night after I removed my chastity chains as my desperate penis became painfully erect. I’m not sure if it got excited as a result of my touching it as I removed the chains or if it was the anticipation of the loosening of the chains (perhaps both). As I watched my penis becoming erect I once again thought it looked smaller than in the past. I was shocked when I took a ruler and laid it against my penis to check. As you can see in the attached photos, my erect penis is now less than 5 inches long! When I measured it a couple of years ago when I first fashioned my chastity sleeve I remember that it was a full 6 inches long. I can only assume that wearing my severely tightened chastity for so long has reduced the length of my already inadequate penis.

Even 6 inches is nothing to brag about, but it is incredibly humiliating to realize that my penis has shrunk so much smaller. Do you think it might get longer again once my chastity chains are loosened? I can’t imagine that adding back a single link to only four of my chains is going to restore a full inch back to my shrunken penis. I hope that in time I regain some of my lost length. But if it turns out that my penis has been permanently shrunk I sincerely hope that it provides you with some pleasure and satisfaction, or at least some amusement.

Correction extended

July 20, 2012

It was extremely painful & frustrating to endure an entire week with my chastity chains tightened so viciously. Even partial erections were out of the question as the chastity chains promptly rewarded any such attempts with a painful bite. As the end of my week’s correction approached I truly looked forward to returning to my regular, looser chastity chains. I knew I would be greatly relieved, but it occurred to me that Ms Lee might be disappointed. She seemed to be greatly enjoying my suffering and frustration. I suspected that it pleased her very much to know that my penis was constantly suffering for her pleasure. As I thought about this a bit more I realized that I should only be concerned about the opportunity to please her, my own discomfort and frustration were irrelevant. Here is the message I sent to her as the end of my correction approached:

I hope that you are doing well and enjoying your new job. I also hope that you have a lovely day.

As of today I have been enduring the intense pain of my shortened chastity chains for an entire week. At times the pain has been excruciating and as I recently reported I no longer can pee while standing up like a man. Instead I must sit on a toilet. I am now back on my knees thanking you for taking the time to correct me for coming without permission. I certainly believe I have learned my lesson well and I will be very careful to avoid accidental, but unauthorized releases in the future.

I also believe (hope) that my situation and correction have pleased you. Although I desperately desire to return to my longer chains I am more desperate to provide you with further pleasure, or at least some additional amusement. I am still on my knees as I beg you to consider allowing me to extend the length of my correction by a period of your choosing. Please let me know if it would please you for me to do this and if so, for how long.

I could picture the smile on Ms Lee’s face as she responded by asking me if I ever thought I would actually beg her to continue the torture my penis was enduring. Then in her typical fashion of inflicting a major impact on my existence on a momentary whim she briefly mentioned that another week would do just fine.

A new experience

July 6, 2012

Recently I had a very embarrassing experience that resulted in my being subjected to another correction by Ms Lee. It has been over two months since she allowed me a pleasurable release and my deprived penis is especially frustrated after I was recently allowed to masturbate (but did not cum!). Here is my report to Ms Lee concerning this experience:

This morning while I was putting on my chastity sleeve I experienced something I never have before. I had attached the first four chains on my sleeve, but was having a terrible struggle getting my desperate penis to accept the bitterly tight fifth chain. This happens almost every morning because my penis gets very excited from being touched as I am attaching the chains. It desperately attempts to enjoy a full erection, but the chains relentlessly bring it to heel and steadily eradicate the erection. I never touch myself in a sexual manner while attaching the chains, but my penis is so desperate for stimulation that any touching at all excites it very much.

This morning I had a particularly difficult time attempting to attach the fifth chain. Time after time I attempted to connect the chain, but the end of my penis was straining like crazy. In retrospect I suppose I should have distracted myself reading the news or something and just waited for my penis to calm down. Unfortunately, in my determination to attach the fifth chain I suppose I inadvertently provided my penis too much stimulation. I started to feel a strange sensation in my penis and realized that I was about to experience a release. I immediately took my hands away and tried to settle down, but it was too late. A small quantity of cum began to dribble out of the end of my penis and it just kept dribbling in this manner for a while. If my penis were not restrained by the four chains I’m sure I would have just released all at once, but the chains prevented this and only allowed a slow, pathetic dribble. I did eventually produce what appeared to be a full load of cum, but the experience was nothing like a normal release.

I suppose what I expereinced was a ruined orgasm since I had a full release, but experienced no sexual pleasure from it whatsoever. However, unlike any ruined orgasms I had before, I did not attempt to excite myself in any way before the release. I did not play with myself or masturbate, so there was no pleasure before my release. And I certainly did not gain any pleasure from the release since it was forced to dribble out of my firmly retrained penis. In fact, I am quite disappointed since I have now released over two months of built up cum, but accidentally, not as a result of milking myself or being teased.

As you would expect, I licked up the cum I released before I cleaned myself up. I then finished attaching all 5 chains to my chastity sleeve and put today’s panties on. I’m not sure if I should consider this as the start of a new chastity period, or a continuation of my current one since I was not allowed a pleasurable release. Please let me know if I should start the count of my number of days in chastity back at zero.

I was hoping that Ms Lee would be amused by my experience and perhaps be sympathetic to my plight. I do think she was amused as she replied that the good news was a healthy prostate. The bad news however was that I had cum without her permission. She told me to propose a list of ten possible corrections for my failure to control myself from which she would select two. Here is my response with my list:

Omg! I can’t beleive I have earned myself another correction.

I do have to admit that I came without permission, so I accept the fact that I require correction for my transgression. Below is my list of 10 options for you to choose from. Some of the corrections are relatively minor and some are much more severe than I expect you will choose. I wanted to provide you a range of options since I have no idea how severe you expect my correction to be. You never fail to surprise me and I will be breathlessly awaiting your decision.

1) Commit to experiencing no releases at all for at least another month.

2) Commit to experiencing no releases at all for at least two months.

3) Whip my penis until it is bruised and marked, at least as visible as previously, if not more so.

4) Whip my rear with my belt until it is at least as black & blue as last time.

5) Purchase the Gates of Hell CBT Plug for you as my July monthly tribute.

6) Temporarily (for at least a week) shorten the other four chains on my chastity sleeve by one link. This will leave them only about one link longer than the viciously tight fifth chain.

7) Permanently shorten the other four chains on my chastity sleeve by one link.

8) Purchase another pair of extremely feminine panties to replace one of the ones I currently wear.

9) Whip my rear with my belt until it is visibly bleeding (last time I caused a few small bleeding spots, but nothing very serious). I’m not sure I would be able to do this, but I will attempt it if you desire.

10) Commit to experiencing no pleasurable releases for an entire year – nothing but milking or ruined releases to be allowed.

Thank you for taking the time to correct me for my transgression. I am on my knees begging your forgiveness as I send you this list of corrections.

I felt quite relieved that Ms Lee did not select some of the more severe corrections I suggested. The two she chose were:

Option 5 (cbt plug)
Option 6 (temporarily shorten other 4 chains for one week)

I immediately shortened my other four chastity chains as she expected. I was shocked at how incredibly tight this made my chastity sleeve. It feels like my poor penis is constantly being pinched and squashed. At the end of every day it is red, raw and sore with deep marks left by the tightened chastity chains.

Four weeks in severe chastity

May 11, 2012

I have now been in chastity for four weeks and I continue to endure the viciously tight fifth chain that I added to my sleeve. I am becoming accustomed to it, but my penis is still raw and tender by the end of each long, frustrating day. At times the pain is almost unbearable, but the thought that my obedience might be pleasing Ms Lee enables me to get thru the days. Perversely, it excites me to realize that my suffering might also be pleasing to her. I am beginning to worry that Ms Lee might consider the fifth chain a permanent modification.

About a week ago I sent Ms Lee another photo displaying the effects of the fifth chain. Here is the message I sent with the photo:

I hope the photo I sent yesterday pleased you, displaying my determination to endure any amount of frustration or pain in submission to your expectations. As I near three weeks in chastity my desperation is mounting, but I have faithfully obeyed your no touching rule. The severe chastity inflicted by my fifth chain combined with the lesson I learned from your recent correction has enabled me to stay focused on your pleasure and satisfaction.

Attached is another photo I hope you might appreciate, displaying the effect of my exceedingly tight fifth chastity chain. The photo shows my firmly chastised penis as it attempts a futile effort to become erect. You can clearly see the four original chastity chains, but the new fifth one just behind the head of my penis is so tight that it is buried in the fabric of my sleeve.

Wishing you a lovely day.

In my 19th day of chastity for your pleasure,
Wearing my purple panties with pink waistband

Administering my punishment

April 20, 2012

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

April 18, 2012

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.

 

CBT for Ms Lee

December 10, 2011

During my recent chat with one of Ms Lee’s boys the subject of experiencing punishment for her pleasure came up. I mentioned that after nearly two months in chastity I was desperate to please her and would be anxious to mark myself to demonstrate my submission to her. I had previously whipped myself for her until red stripes were visible on my rear. After I finsihed chatting with Ms Lee’s boy I had a chance to talk to her and brought up my desire to please her in this manner.

I was not at all prepared for her response. I had told her I was desperate for release and she had responded:

oh fine. try to milk yourself. no touching, though

When I then brought up the suggestion of marking myself for her she replied:

if you are able to milk yourself, i want you to clean it up, then immediately mark yourself –on your penis & scrotum  pics of that plz. i’m a big fan of cock and ball torture

I was not at all prepared for this. Whipping my rear until it was marked was bad enough, but I couldn’t imagine the pain that would be involved in marking my cock and balls. But I also couldn’t imagine disappointing Ms Lee so I resolved to do as she expected.

The next morning I sent Ms Lee this message regarding my effort to do as she expected:

This morning I attempted to milk myself, but after 20 minutes of desperate grinding and humping I was only able to produce what I would consider pre cum. I think that those times I thought I was in danger of an unauthorized release were false alarms. I slowly built up to the same sense of excitement this morning, but then discovered it was not enough to get me to produce. Quite frustrating! I think I may need one of those anal dildos I’ve heard of (Aneros?), perhaps you might allow me to get one as a Christmas gift from you.

At times I was humping so madly that I found myself using my anal muscles to try to pull the plug in deeper. I am embarressed to admit that I actually began to wonder if that was what it was like for a woman when they are being penetrated.

Although I was not able to fully milk myself, I thought it might please you if I marked myself as you described last night. I used the same belt that I had used previously to mark my rear for you.

You had commented that I would not be able to really mark myself, that I would probably only be able to redden myself. I also remembered how hard it was to mark my rear with my belt, so I spent 10 minutes whipping my cock and balls as hard as I could. I was concentrating on hitting the shaft of my cock as I thought that would redden easiest. It almost brought tears to my eyes every time the belt happened to hit the head of my cock. I would have continued, but after 10 minutes my knees were shaking so badly from the pain that I could hardly stand up. As a matter of fact, they are still shaking right now.

When I stopped whipping myself and looked at the results, I saw why my knees were shaking so bad. I had managed to inflict some nasty marks on my poor, punished cock, as you can see in the attached photos. I have more photos I will send later.

My penis is stinging from the pain of the whipping and my knees won’t stop shaking. However, if my attempt to mark myself pleases you then the pain is more than worth it.

In my 53rd day of chastity for your pleasure,
wearing my red panties with garters

I expected that Ms Lee would be impressed with my desperate attempt to please her and the intense pain that I had endured. I was shocked when her reply indicated that she was not impressed or pleased in the least:

Gross. Trim.  Stop sending me pictures of you in need of a trim.  You know by now I don’t like that.  Take care of it and mark yourself again after trimming.  Also,you may purchase that for yourself as a Christmas gift from me.
Happy Friday!
I was intensely disappointed that I had failed to please Ms Lee and prompltly did as she expected, sending this message in reply:
Attached are photos of my cock after I re-trimmed and re-marked it. It was incredibly painful to whip my cock again after it had already been beaten so badly, but I deserved it for not properly trimming myself the first time.The first time I whipped my cock it was the left side of it that got marked, since I was using my right arm, striking down and over. This time I worked on the other side of my cock (the right) to even the marks up a bit. The first two photos show the result of this.(the cut on my thumb is from Thanksgiving).

The 3rd photo shows the left side of my cock with darker bruises than before. My cock is changing color already, but I’m sure it will be at least a week before it clears up.

I will put my chastity sleeve back on now, I think my cock is swollen a bit from the whippings. The sleeve felt very tight after the first whipping and I felt a constant stinging/burning sensation as it strained against the sleeve.

I can’t begin to describe how happy I was when Ms Lee then expressed her satisfaction with my performance:
Lovely,  I’m happy.