A rare and generous treat

After my recent accidental (and pleasureless) release I was certain that it would please Ms Lee to see me endure another 100 days or more of chastity before she allowed me another release. Instead I was pleasantly surprised when she informed me less than a week later that I was to be allowed another release. Even more surprising was that she was going to allow me to enjoy a very rare pleasurable release! This was an extremely generous gift and I am quite aware that it may be a long, long time before I am allowed such a treat again.

Ms Lee had taken note that in my last blog entry that I mentioned I am unable to masturbate for more than a minute or two anymore. When I used to release almost every day I was able to enjoy masturbation for long periods of time. But due to the extended chastity periods I now endure as Ms Lee’s property I am no longer able to do so. On those rare occasions when I am allowed to masturbate the pent-up pressure in my balls makes me so frantic that I lose control almost immediately. This is quite frustrating and I can only hope that it pleases Ms Lee to have ruined my ability to derive any real enjoyment from masturbation.

Ms Lee informed me that two minutes was thus going to be the limit for how long I would be allowed to masturbate. She told me to set a timer and have at it until the timer went off. I have to admit that it was intimidating to be faced with such a strict limit on how long I would be allowed to enjoy myself, particularly since it had been just about 120 days since I had enjoyed my last pleasurable release. As I pondered this it occurred to me that Ms Lee was rewarding me with exactly one second of pleasure for each entire day of chastity that I had endured for her.

To make things even more frustrating (if that was possible!) it took me a while to even get hard once I had started the timer. I was probably too focused on my time limit and frustration to allow myself to truly enjoy masturbating and I saw that thirty seconds had passed before I was able to achieve a full erection. As I continued to stroke my desperate penis I finally began to feel the true pleasure of masturbation and realized just how badly I missed being allowed to jack off at will. The realization that Ms Lee had taken such complete ownership of my sexual pleasure instilled such a perverse, intense excitement that I lost control and began to feel my balls clench and pulse in preparation to release. I desperately wanted to slow down so I could enjoy the full amount of time I was allowed but as I passed the minute and a quarter mark I released a messy load that I then licked up as I knew Ms Lee would expect.

I promptly thanked Ms Lee for allowing me such a generous gift and immediately returned to faithful chastity for her pleasure. I can only hope that she does not reduce my time limit accordingly for my next release now that I have once again demonstrated my pitiful lack of control.

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.