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.

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