Allowed to beg

My growing anal obsession was not limited to Ms Lee’s perfect rear. Every morning during Worship my deprived penis would get quite excited as I ground and rammed against my huge Worship plug. Although the single chastity chain I wore as a penis ring during Worship prevented me from enjoying a full erection, it did allow my penis much more freedom than my full chastity sleeve. These sessions were the only time each day when my penis was allowed any sort of sexual excitement and were a significant source of my growing anal obsession.

I was becoming so desperate that during a chat with Ms Lee I asked her if I could plead my case to be allowed to attempt to relieve the pressure in my balls by anal stimulation alone. She graciously gave me permission to beg her for this by email. Here is the first such begging email I sent to her:

Dear Ms Lee,

In two days I will pass 42 days in chastity for your pleasure and set a new record. Over the last few weeks I have felt the pressure building in my balls at the same time as my penis throbs ever harder within my sleeve. I am desperate for any sort of sexual stimulation, but the only time my penis is allowed any freedom at all is during my morning Worship sessions. During these sessions I am still not allowed to touch, but instead I derive my pleasure by ramming my anal plug deep inside my rear, which excites my prostate.

I can sense my sexual orientation focusing stronger and stronger on my rear as this is the only form of sexual stimulation I am allowed on a daily basis. My penis continues to strain madly against my sleeve, but I am learning that this form of pleasure is rarely available to me. At times during my Worship session I begin to approach the point where I think I might be able to produce even though I am not touching myself. However, I always stop because I know I am not allowed to ejaculate. The single chain I use as a cock ring prevents me from experiencing a full, unfettered erection, but I doubt it would stop me from exploding in release if I let loose.

As I have been experiencing this frustration on a daily basis I have been remembering the chat we had a while back about milking me – allowing my semen to release, but not allowing me a pleasurable ejaculation. I believe this might be possible if I were wearing my chastity sleeve with all four chains on while I was exciting my prostate with my huge Worship plug.

I am now on my knees as I beg you to consider allowing me to do this after I set a new chastity record. The pressure in my balls is getting truly intense and I am desperate for some relief. I know I am not allowed to request a pleasurable release, but I hope you would consider allowing me to be milked in this fashion. To insure that there is no chance of my experiencing a real ejaculation I would even fashion a set of ‘milking chains’ for my chastity sleeve. These would be chains shortened by a link or two less than my already tight chastity chains. This would insure that my penis remained firmly restrained and most likely my semen would only dribble out with no chance of an explosive release.

Please, please consider allowing me this! I would be so grateful if you would. As I mentioned before, I believe this would relieve the pressure in my balls,but I think my frustration and desperation would continue unchecked. My frustration would probably even increase due to the lack of a pleasurable release. I am so desperate at this point that I will even suggest that you consider setting my ‘chastity clock’ back to zero after my milking. Instead of enjoying a pleasurable ejaculation before beginning my next chastity period, I merely get milked to relieve the pressure in my balls.

I am now back on my knees begging you to consider this. Please allow me to give up the opportunity for a pleasurable release after setting a new chastity record for you. Instead I beg to be milked so I can begin a new extended time in chastity for you.

In chastity for your pleasure

One Response to “Allowed to beg”

  1. me Says:

    103…never been this far before.

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