Archive for the ‘Cock Ring’ Category

Giving Thanks

November 23, 2011

Recently I have been contemplating the fact that once again I am experiencing an extremely long chastity period for the pleasure of Ms Lee. She sometimes surprises me by allowing a release after a short time in chastity, but it is obvious that she much prefers to see me in extended chastity (over a month).

I am now in my 44th day of chastity for the pleasure of Ms Lee, the second longest period of chastity I have ever experienced. My longest stretch was two months, which ended in a ruined orgasm. I have no idea how much longer it will please Ms Lee to keep me in chastity this time and my frustration increases every time I wonder whether my current chastity period will end with another ruined orgasm.

I just received a message from Ms Lee that she will be very busy the next few days due to the holiday. Of course this means that my current chastity period will be extended as she enjoys her Thanksgiving. Perversely, I could feel my deprived penis straining against my chastity sleeve in frustration as I contemplated continuing my chastity in faithful devotion to Ms Lee.

As I performed my daily Worship session this morning these thoughts took my frustration to new heights. I prepared myself as always, restraining my penis with my cock ring and inserting my huge Worship plug in my greedy rear. Extended chastity combined with Ms Lee’s no touching rule has instilled an intense anal fetish in me since the closest I normally come to experiencing sexual pleasure is when I am plugged and Worshiping Ms Lee.

This morning my desperation and excitement combined to make me delirious as I ground the plug into my rear. That plug is so huge that it presses firmly against my prostate, which in turn causes my penis to strain against my ring. As my Worship session continued I was gyrating like mad, working to increase the sexual stimulation the plug provided.

I could feel my sexual pleasure slowly increase as I continued to grind my prostrate with my plug. I almost reached the point where I thought I might be at risk of an unauthorized release. However, I didn’t quite reach that point and continued my frustrated grinding until my Worship session was completed.

As I panted in exhaustion, I reflected that I am extremely fortunate to be owned by Ms Lee. I love being her boy and ended my Worship session by giving thanks to her for continuing to keep me on.

Allowed to beg

August 14, 2011

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

Daily Worship begins again

July 23, 2011

The very next morning after I received my instructions from Ms Lee I began my daily Worship sessions again. Here is the message I sent her describing that  session:
This morning I performed a formal Worship session for you. It has been a while since I have done one and it brought back pleasant memories of previous sessions I performed for you.

As always, I began my Worship session by working my huge Worship plug into my tight rear. Yesterday was the first time I had used it in the last few weeks and it felt quite huge. I resorted to my method of rotating on the plug and gradually pushing down on it until I was able to stretch my rear enough to accept the intruder. I still feel an intense rush of pain and relief as it finally seats deep inside me.

The pressure of that huge plug inside me always excites me and causes my deprived penis to immediately harden. I had to pause a bit before I could continue my preparations by using one of my chastity chains as a cock ring due to the difficulty I had getting it on my straining penis. Then I slid on my pink & black thong as specified by my panty schedule and was ready to begin my Worship.

Next I recited my Worship phrase:
I need you Ms Lee, I love you, you make me complete

Then I backed up against my toilet bowl and began pushing the Worship plug inside myself. I thought back to all the times I had done this for you before and soon settled into a steady rhythm of grinding and pushing. All the time I could feel my penis straining against the cock ring, snug inside my panties. Thinking of you while doing this always excites me and I pushed against the bowl even harder. I desperately wanted to grab hold of myself and begin masturbating, but of course that is not allowed.

Realizing that you now expect me to do this every day for you again excited me even more and I rammed harder against the bowl. I kept this up for about 20 minutes and finally stopped, frustrated and exhausted. As I did so, I repeated my Worship phrase:
I need you Ms Lee, I love you, you make me complete.

I then cleaned myself up and put my full chastity sleeve on. I now begin a full day in chastity for your pleasure. I have no idea how long this chastity period will last, but I am not focused on that. My desire is to please you and I hope the thought of me restrained in my chastity sleeve brings a smile to your lovely face.

In chastity for you

Another twist on my chastity roller coaster ride

February 7, 2010

Ms Lee recently caught me off guard again by informing me that due to a positive event in her life, I was to celebrate with her. I was to do so by being allowed to masturbate one time for her pleasure. Even more surprising, I was allowed to do so with no restrictions – no chastity sleeve, no cock ring, no panties, nothing! To top it all off I was also allowed to touch myself and use my hands to masturbate.

This was a rare treat indeed for me, but unfortunately i failed to fully enjoy the opportunity. After being in chastity for a month my balls were bursting with pressure. I had intended to take my time and enjoy a leisurely masturbation session. However, within a minute of starting I could feel my cum boiling to the surface and I was unable to resist my greedy pigmale desire to just spurt it out. The pressure and the long-term denial were too much for me and I wasted my one chance to enjoy an old fashioned masturbation experience.

After my very brief masturbation exercise ended I was ashamed that I was unable to hold out any longer. A real man would not have lost control of himself so quickly, but then again Ms Lee has taught me to understand that I am certainly not a real man. I can never hope to please her as a real man does, and can only try my best to please her as her property. As I pondered these truths I realized that this masturbation opportunity was designed to bind me even closer to her will.

Now I am back in chastity for my Goddess’ pleasure and naturally I have no idea how long this chastity period will last. Even worse, I fear that Ms Lee will not be so generous next time and I may not enjoy such unrestricted freedom the next time she allows me to produce.

How i Worship my Goddess

January 10, 2010

First i want to apologize to Ms Lee and my loyal readers for not posting to this blog last week. I was very sick with the flu and wasn’t really in the mood to do anything but lie in bed and hold my aching head. I am much better now and back to my normal routine.

One of my readers recently asked how I go about Worshipping my Goddess. My Worship sessions are actually quite elaborate as Ms Lee has very high expectations of her boys. I must perform my Worship EVERY morning without fail. Only on very rare occasion, with an advance request for a valid reason, am I allowed to go for a day without completing my Worship session.

First I had to compose a sincere oath to Ms Lee, expressing my sincere desire to serve and obey her. My oath is fairly long, nearly 500 words, so I will not quote it right now. It is in the form of a prayer to my Goddess.

Before I recite my oath, I must prepare myself for Worship. First I take off all my clothes, then I must insert the butt plug that I purchased for my Worship seesions. As I mentioned in my post ‘Preparing my rear for Ms Lee’, I foolishly purchased a plug nearly two inches across in a vain attempt to impress my Goddess. She has never indicated that this impressed her in any way, but I am still expected to use this plug every day during Worship.

Next I must harness my penis with Ms Lee’s cock ring which I fashioned from a key chain. It is VERY snug and once in place prevents anything close to a full erection. While I am wearing it, my cock experiences significant pain every time it attempts to get erect. This is particularly frustrating because my Worship sessions tend to excite me quite a bit.

The last step in my preparations is to put on my pretty panties which Ms Lee had me purchase. I am not a cross dresser, and I find wearing panties to very humiliating, but strangly erotic. I think the humiliation turns me on. Recently Ms Lee has begun to require me to wear my panties every day, all day long, but that is a story for a later time.

Once I have completed my preparations, I then assume my Worship position, on my kness, head down, arms extended and my rear pressed up against the bowl of my toilet. Ms Lee did not require the toilet bowl, but did indicate that I must press my rear against something so that my anal plug is pressed deeply inside me. I found that the toilet bowl in my bathroom worked quite well for this purpose.

Once I am in position, I am then to imagine that Ms Lee is f*cking me. I begin grinding my rear against the bowl, feeling the plug plunge deeply inside.Only when I am sufficiently excited and turned on am I to begin reciting my oath to Ms Lee, out loud.

I continue in this way for 20 minutes, every morning. At no time am I allowed to touch myself or allow myself to ejaculate without Ms Lee’s express approcal. Readers of my blog will know that such approval is very rare. Many times during Worship I find that I must pause and calm down in order to avoid the possibility of an unauthorized ejaculation. Yes, I have found that I can get excited enough during Worship to cum without using my hands, if I grind and buck hard enough.

When my 20 minutes of Worship are completed, I finish my session with a heartfelt prayer of thanks to Ms Lee for being my perfect Goddess. I also have to (as instructed by her)  ‘ask Her to forgive me for being so horny, so nasty, such a worthless little pigmaile, so needy, with my ass left so hot and aching after penetration’.

My last step is to then email Ms Lee with a detailed explanation of my Worship session. Again, this is required every morning, without fail.

Fantasizing about my Goddess with a Real man

September 6, 2009

Recently Ms Lee informed me that She would be spending a day with Her boyfriend. Her boyfriend is not a submissive like me, he is a real man, free to enjoy sexual pleasures and everything else that a real man is entitled to.

As soon as Me Lee mentioned this to me i could feel my cock begin to harden, betraying my true feelings on this topic. If i were a real man i would be jealous that Ms Lee was going out with another man. But i am not a real man and the reaction of my cock demonstrated that truth. The thought of Ms Lee with a real man excites me and i can’t stop fantasizing about it.

i can picture Ms Lee enjoying Herself with Her boyfriend, freely giving him what i will never have. Thinking about this both frustrates and excites me. What really blows my mind is the realization that She is requiring me to remain chaste for Her while Her boyfriend is free to enjoy himself as a real man.

Every time i think about Ms Lee with Her boyfriend my cock begins to harden, but Her ring cruelly prevents a full erection. This really drives me crazy because thinking about the pleasures Ms Lee will allow Her boyfriend causes my cock to be in pain.

Although it results in even more severe pain for my pitiful cock, i can’t stop thinking about how incredibly humiliating it would be to be required to provide oral service for Ms Lee after She enjoyed sex with Her boyfriend. i would be determined to please Her, but as Her well trained boy i know that this would not earn me the release i so desperately crave. i cannot ‘earn’ my release, i am only allowed to ejaculate when Ms Lee decides it would please or amuse Her to grant me that privilege.  The best i could hope for would be to bring Her to another orgasm and to excite her boyfriend enough to take Her again as only a real man can.

my extended chastity

July 28, 2009

It has been nearly a week since Ms Lee denied my request for permission to cum with this message:

boy, Ha.  Ha-ha-ha-hah!  Of course you may not cum.  If you ask again, I will extend your chastity period well beyond what you would deem comfortable..

–> Ms Lee

i don’t dare ask again becuase i don’t want to find out what my Goddess considers ‘well beyond comfortable’.  She has not even raised the topic since then and seems to be content with leaving me to adhere quietly to Her decision.

It is now 27 days since Ms Lee last allowed me to cum.  i have absolutely no idea how long She intends to extend my current chastity period, but i consider this an opportunity to demonstrate my devotion to Her.

i am so desperate for relief that it is almost painful. my balls are swollen from the built up pressure and my cock is constantly getting hard. Unfortunately for my cock, Ms Lee requires me to wear a very snug cock ring for several hours each morning. During this period my cock is ruthlessly prevented from achieving a full erection by the vicious bite of Her ring.

Of course my pigmale desire to cum is inconsequential. The only thing i desire is to be allowed to continue to be Ms Lee’s faithful boy. She is my Goddess and i belong to Her.

Wearing Ms Lee’s Ring

July 5, 2009

My Goddess requires me to wear Her ring a few hours each day.  As Her property, i obey Her unfailingly, so i have been wearing Her ring every day since She informed me of this expectation.

No problem you say? Well, it is when the ring in question goes around the base of my cock! Unfortunately for me, Her ring is smaller in diameter than my cock is when erect. i must wear it at the base of my cock and i hardly notice it when i am flacid. But as soon as i begin to get an erection, Her ring takes control. It begins to bite into my poor cock which actually begins to turn blue from the severe constriction if i don’t find a way to return to flacidity.

Wearing this ring every day has begun to change me. Although it allows me to achieve a full hard-on, i must pay a very painful price. This takes the fun out of erections and changes my attitude about them. Instead of being able to enjoy erections like a real man, Her ring bites me and reminds me that i am Her property.

i’m not sure if Ms Lee knew the effect that wearing Her ring would have on me, but She usually knows much more than i suspect. i am usually scrambling a few steps behind Her, trying to keep up with Her demanding pace and never knowing what devious twist She will come up with next. While i am still trying to satisfy Her previous demands and coming to understand all their implications, She is already planning my next demonstration of devotion.