The Generosity of Ms Lee

When I went to sleep Tuesday night I set two alarms to make sure I would wake up in time since Ms Lee generously had given me permission to touch myself and cum between 6 and 6:30 Wednesday morning. I was horrified when I woke up that morning at 7:30, having slept thru both alarms. I desperately wanted to masturbate, but I dared not touch myself since I missed the time-frame Ms Lee had specified. I told her about my failure and expected her to tell me that I had squandered my opportunity for the week.

I was ecstatic when she told me that she would give me another chance at 6PM that evening. Although Ms Lee is extremely strict with me she also is very caring and surprises me with her generosity.

At 6PM promptly I began enjoying Ms Lee’s gift and began touching myself in a sexual manner for the first time in over a week. It was heavenly to once again enjoy a full erection and stroke it with abandon. I took it slow at first as I wanted to be able to enjoy the full half hour that Ms Lee had allowed me. My hair trigger penis almost betrayed me as within minutes I could feel myself almost explode in release. I quickly let go of my penis and waited until I calmed down before touching myself again. Before beginning again I thanked Ms Lee once more for her generosity, I am so fortunate to be her property.

I also took the opportunity of being hard to measure my penis to check on whether I had fully regained the length I had lost due to my previous cycles of extremely extended chastity, restrained by my viciously tight chastity sleeve. I was shocked when I discovered that I measured somewhat less than five and a half inches, more than half an inch less than I was prior to becoming the Property of Ms Lee. I informed Ms Lee of this and her response indicated that she did not consider my loss a big deal. Perhaps she is correct since I never have the opportunity to use my penis like a real man anyway. I just hope that it pleases Ms Lee that her property has been reduced in size due to the extended chastity it has previously been subjected to for her pleasure.

I spent more time hands off trying to control myself then I spent masturbating, but I did manage to take advantage of the full half hour before releasing. As the final moments approached I began stroking like mad and quickly felt my release approaching. As Ms Lee expected, I squeezed the tip of my penis as well as my scrotum as my cum attempted to explode out of my penis. I successfully managed to prevent the explosion and could feel it backing up behind where I squeezed. Once my orgasmic spasms ended I released the tip of my penis and saw my cum slowly dribble out. I was amazed at how much kept dribbling out and I dutifully licked it all up as Ms Lee expected. I then thanked Ms Lee again for her generosity.

It has now been two days since my ruined release and I intend to wait until a full week passes before I dare to beg Ms Lee once more for permission to touch myself. I am hopeful that by then I will be in the proper state of mind to beg sincerely.

Being allowed to touch myself reminded me of the intense joy & pleasure that I am denied and having a ruined rather than an orgasmic release insured that my frustration and desperation continued unchecked. I suspect Ms Lee intended things this way and I only hope she enjoys having her property obedient and untouched.

A squandered opportunity

During the years that I have spent as The Property of Ms Lee I have come to understand that Ms Lee enjoys seeing me endure increasingly extended periods of strict chastity. As my chastity periods began to counted in terms of months Ms Lee kindly allowed me to attempt to milk myself to release the pressure in my balls, but only very rarely allowed me to touch myself in a sexual manner.  And I never know whether my chastity periods will end in a pleasurable or ruined release.

All of this keeps me in a heightened state of extreme frustration. This longer my period of chastity the more desperate I become to please Ms Lee, which may explain why she steadily increases my chastity periods. I suspect she also just simply enjoys owning a boy whose sexual pleasure is always firmly denied.

To keep my sexual pleasure firmly under her control Ms Lee requires that my inadequate penis be restrained by my cruelly tight chastity sleeve. I am allowed to remove my sleeve while I sleep, but it must immediately go back on as soon as I wake and finish taking my morning shower. At first my chastity sleeve was kept in place by three relatively loose chains, but over time the chains were shortened and more were added. My shrunken penis is now firmly restrained by five viciously tight chains.

Obviously I could cheat while my sleeve is not in place but long ago Ms Lee trained me to understand that I would only be cheating myself out of the joy of knowing that I am her loyal boy, pleasing her with my extended chastity. She also trained me to understand that for a boy with an inadequate penis, masturbation only provides me with a short lived pleasure. And as a result of extensive long term chastity I no longer have the self control to enjoy masturbation for more than a brief minute or two.

Ms Lee has trained me to understand that long term chastity is much more appropriate and satisfying for a boy like me. My satisfaction comes from knowing that my chastity pleases her. Unlike masturbation there is no limit to how long I can enjoy the satisfaction of pleasing Ms Lee in this way. And perversely I have learned to feel comforted by the embrace of the chastity chains. When I feel the cruel bite of the chains it actually feels like Ms Lee has me in her firm grip, reminding me how fortunate I am to be her boy.

Unfortunately my growing inability to control myself led to a squandered opportunity recently. My frustration had reached a fever pitch as I exceeded 100 days in chastity for the pleasure of Ms Lee.  One morning as I was attaching the chains that encircle my chastity sleeve I felt my deprived penis begin to tremble, which frequently happens while attaching the tight chains around my straining penis. When this happens I have to wait for my penis to calm down and shrink enough to attach the chain. But this time my unruly penis did not calm down and instead began to leak and dribble uncontrollably. I clearly released a full load but I experienced no pleasure whatsoever. Instead I had a frustrating, ruined orgasm.

I promptly reported my lack of control to Ms Lee, expecting to be punished for releasing without her permission. I was pleasantly surprised when she told me that I was ok because she had been just about to tell me to have a release. But I was heartbroken when I learned that she had intended to allow me a rare pleasurable release. Because I was unable to control myself I had blown my chance and instead had to suffer the intense frustration of a ruined orgasm.

Although the pressure in my balls has been relieved my frustration has continued unabated. In fact it has been greatly magnified, knowing that it could very well be spring time before it pleases Ms Lee to allow me to release again. And of course I have no idea whether she will then enjoy seeing me experience a pleasurable release, or just the frustration of another ruined orgasm.

A new experience

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.

Permission to masturbate

Yesterday Ms Lee surprised me by giving me permission to masturbate. I have been in chastity for nearly two months while faithfully abiding by her no touching rule, so I was quite excited as I read her message:

When you get this email, at first opportunity today, and today only, remove all chains. Plug up. Remove sleeve. Masturbate & edge, then back off. Keep edging & backing off (no ejaculation at all) for 20 minutes. When done, you may use the plug to try and cum, but use the plug and the plug only. You may touch the plug, but can no longer touch your penis. When done, put the sleeve & chains back on.

Needless to say, I did exactly as Ms Lee expected, even though it was incredibly frustrating. When I was finished I immediately sent her a report on my experience:

I am on my knees right now thanking you for providing me an opportunity to masturbate, even though I was not allowed to release while touching myself. After 57 days in extended chastity, and abiding by your no touching rule, it was deliciously frustrating to be allowed to edge, but not to ejaculate.

I was out when I received your email and my penis strained against my chastity sleeve like crazy as I anticipated how awesome it would be to actually touch myself in a sexual manner. When I finally got home and had some privacy I quickly removed my chains, inserted my plug and removed my sleeve. As I took hold of my penis and began to stroke it I began to understand just how torturous it would be to edge for 20 minutes while ejaculation was prohibited. In less than a minute I had to stop stroking for fear that I might release my huge load of build up cum already. My penis twitched and shook from the intense teasing as I struggled to control myself. I desperately wanted to grab hold of my penis and masturbate like a mad man, but I was determined that I would not disappoint you by allowing an unauthorized release.

I probably wasted at lease a minute waiting for my deprived penis to calm down enough so that I dared to begin stroking again. Once again I had to stop well before another minute was up as I felt my unruly penis begin to twitch again. I was tortured by the realization that I was spending much more time desperately fighting for control than I was enjoying my brief opportunity to enjoy touching myself. I tried slowly rubbing my shaft, but within seconds I was masturbating furiously again, almost losing control as I reluctantly released my penis and watched it twitch once more.

I continued this frustrating cycle, alternating between very brief periods of delirious sexual enjoyment separated by much longer periods of desperately fighting to control my pigmale desire to release explosively. As I glanced at the clock I realized that I had already squandered well over half the time you had generously allowed me to play with myself and had only managed a few minutes of actual masturbation. Perversely this only caused me to stroke more furiously, quickly reaching the point where my twitching penis forced me to stop again.

All too soon I reached the final minute of my masturbation allowance and I desperately tried to control myself so I could enjoy it. Unfortunately I almost immediately began twitching again and reluctantly had to stop once again. I almost cried as I saw the clock reach the twenty minute mark, realizing that I was no longer allowed to touch myself.

The next portion of your generosity was even more frustrating as I tried to milk myself with my huge Worship plug. I desperately wanted to stroke myself as I did so, but my no touching training effectively prevented me from doing so. I was being driven insane as I gyrated like crazy, but was unable to produce. Soon I was ramming the plug into my rear, imagining you taking me with your strap on. I kept up in this manner for quite a while and finally collapsed in exhaustion, realizing that the plug alone was not enough to get me off.

I then removed the plug, cleaned myself up and put the sleeve & chains back on. That nasty fifth chain bit viciously as it eliminated the last of my erection and returned my poor penis to extended chastity.

It is so much harder to resist the urge to touch myself now that I have been reminded how pleasurable it is to masturbate. I am almost glad that the fifth chain is back in place, firmly enforcing your no touching rule.

Once again I am back on my knees thanking you for this opportunity. I hope it pleases you that I remain in faithful chastity for your pleasure.

A couple of hours later I realized that my deprived penis had released a small bit of cum. It was nothing like a full milking or ruined orgasm, it was more like a pathetic leakage that did nothing but frustrate me even more.

The dry spell continues

As the first day of spring approaches I’m reflecting on the fact that I’ve only experienced two releases during the entire three month winter season. I am now averaging 45 days between releases and it is quite clear that Ms Lee has established lengthy, extended chastity as my normal state. I am now approaching a full month since my last release, but I am well aware that it might please Ms Lee to see me go through another month (or more!) of chastity before I am allowed any sort of release.
Ms Lee has continued her program of training me to empathize with the sexual frustration that a woman feels when she is left unsatisfied by a man. Every morning when I attempt to milk myself with my vibrating anal dildo I concentrate on learning this lesson. I am so desperate for any sexual stimulation that I have developed an intense craving for anal pleasure. At the same time I have come to accept the reality that my penis has ceased to be the center of my sexual focus.
Another aspect of my new sexual reality is that I realize it is pointless for me to think about enjoying normal male orgasms. I must concentrate instead on learning how to enjoy the limited, frustrating pleasure that anal stimulation provides. Even when I am allowed a special, rare release I know that Ms Lee might prefer to see my orgasm ruined, extending my period of frustration and denial. Ms Lee has spoiled me with two pleasurable releases already this year, so I am preparing my self for the real possibility that I could be entering another long dry spell. Then again, Ms Lee always keeps me off balance and seems to enjoy surprising me, so there is truly no way for me to anticipate what the new season may bring.

A dry year

As the year draws to a close I looked back over my blog postings and realized that 2011 has been a year of very few releases for me. It seems that this year Ms Lee has grown much more fond of seeing me in extremely extended chastity for her pleasure. There were a few instances when she allowed me to release more frequently, but there have also been multiple times when she kept me in chastity for over two months, something I never experienced before this year.

In case you are interested, below is a list of my releases this year, including notes as to whether I enjoyed a pleasurable release, a ruined orgasm or just a milking. This year is also the first time I experienced ruined orgasms and milkings. Ms Lee seems to be growing more fond of these types of releases for me, with pleasurable releases becoming quite rare indeed.

I don’t have a record of my releases prior to April 1 of this year, but the list below certainly provides a good idea of Ms Lee’s penchant for extended chastity.

April 1 – Pleasurable release

May 12 – Pleasurable release

July 13 – My first ruined orgasm

July 28 – Another ruined orgasm

August 7 – Pleasurable release

September 1 – Another ruined orgasm

October 8 – My last pleasurable release of 2011

December 18 – My first milking

I calculated that the average time between my releases this year has been a little over a month (34 days). In case you think this is overly generous, you may also want to consider that it has been 81 days since my last pleasurable release.