Severe chastity continues

About the time that I reached 5 weeks in chastity Ms Lee took mercy upon me and told me to take a week off from wearing the viciously tight fifth chastity chain. I was extremely thankful for her generosity and enjoyed an entire week free from the intense pain inflicted by that chain whenever my deprived penis attempted to become erect. The remaining four chains were still quite effective at preventing anything approaching a full erection, but without the nasty bite that the fifth chain inflicts.

When my week of relative freedom was up I sent Ms Lee this message, asking at the end whether I was to return to the harsh control of the fifth chain:

As I continue my seventh week in chastity my desperation is reaching incredible heights, but when my frustration becomes too much I remind myself that my extended chastity is an opportunity to please you. I love pleasing you with extended chastity, but my hormones do begin to rage against the denial.This morning during Worship I was grinding against my huge Worship plug as hard as I could, but was unable to achieve any sort of release. I believe I have enough built up pressure inside that I am ready to try milking myself with my vibrating anal dildo again. I am not sure if you will consider my chastity period extended enough yet, but I think I will be begging you for permission to use it before long.

I also had an incredible struggle getting my chastity sleeve on this morning. My greedy penis kept straining against the sleeve as I slid it on. I am insanely horny this morning and my penis will not stop attempting to get hard. Every chain was another huge struggle and it took quite a while to get all four chains onto my unruly penis. Without the extra tight fifth chain my penis continues to bulge out between the four chains, but is unable to achieve anything near a true erection. I have enjoyed a week without the daily suffering inflicted by my fifth chain, but I think the week is about up, so I am now on my knees asking you to let me know whether I am to return to the extra security enforced by the fifth chain.

In my 43rd day of chastity for your pleasure,
wearing my pink panties today

I could have just resumed wearing the fifth chain without asking, but I was hopeful that Ms Lee might extend my period of freedom from that nasty fifth chain. Her reply was short and clear:

I do like that fifth chain.  Time to put it back on.

I felt like a condemned man when I received her response, but I have to admit that perversely, my penis twitched in desperate frustration as I read it. It has now been three days since I resumed enduring the intense restriction of the fifth chain. Once again my penis is raw and sore at the end of each day of painful chastity, but my only concern is for the pleasure of Ms Lee.

Four weeks in severe chastity

I have now been in chastity for four weeks and I continue to endure the viciously tight fifth chain that I added to my sleeve. I am becoming accustomed to it, but my penis is still raw and tender by the end of each long, frustrating day. At times the pain is almost unbearable, but the thought that my obedience might be pleasing Ms Lee enables me to get thru the days. Perversely, it excites me to realize that my suffering might also be pleasing to her. I am beginning to worry that Ms Lee might consider the fifth chain a permanent modification.

About a week ago I sent Ms Lee another photo displaying the effects of the fifth chain. Here is the message I sent with the photo:

I hope the photo I sent yesterday pleased you, displaying my determination to endure any amount of frustration or pain in submission to your expectations. As I near three weeks in chastity my desperation is mounting, but I have faithfully obeyed your no touching rule. The severe chastity inflicted by my fifth chain combined with the lesson I learned from your recent correction has enabled me to stay focused on your pleasure and satisfaction.

Attached is another photo I hope you might appreciate, displaying the effect of my exceedingly tight fifth chastity chain. The photo shows my firmly chastised penis as it attempts a futile effort to become erect. You can clearly see the four original chastity chains, but the new fifth one just behind the head of my penis is so tight that it is buried in the fabric of my sleeve.

Wishing you a lovely day.

In my 19th day of chastity for your pleasure,
Wearing my purple panties with pink waistband

Return to regular Worship

During the first week of enduring the viciously tight fifth chain I kept expecting Ms Lee to take pity on me and tell me I should stop wearing it. Gradually I came to the realization that she probably preferred seeing me this way, secure in my firm chastity and suffering for her pleasure. As I began my second week of secure chastity I sent Ms Lee an update on what I had been experiencing:

I don’t want to spend too much time boring you with my sexual frustrations, but I do feel I should briefly let you know how I am doing. I am now well into my third week of chastity combined with no anal stimulation at all – no plug during Worship or at any other time. I have also been enduring my extremely tight fifth chastity chain for over a week now. Due to my extended chastity and denial of stimulation my penis is frequently throbbing in desperation. Every time that happens my chastity brutally prevents the feeble attempts at erection and my only reward is the pain of the chains digging in. By the end of the day my penis is sore and red from its futile struggles. However, the pain and frustration is worth it if the result is your satisfaction and pleasure with my faithful obedience.

I think I will be on my knees begging for the anal plug again quite soon.

I have to admit that I was relieved when I received this reply from Ms Lee:

Resume your plug & regular worship now.

The next day I gave Ms Lee a report on my return to regular Worship using my plug:

This morning it was so nice to be able to use my Worship plug, I have felt so empty! It was a bit difficult getting it in as my rear as not been stretched lately, but it felt wonderful once it was all the way inside and rubbing against my prostate. All too soon I was gyrating like mad, enjoying some sexual stimulation at last. I was shocked when I realized that I may have been more desperate for anal stimulation than stimulation of my penis. Perhaps because it is the only type of sexual pleasure I am usually allowed anymore.

Also, attached is a photo that shows my penis after I removed the sleeve at the end of day yesterday. There are some blood marks that are not too visible, but I think they demonstrate just how tightly restrained my penis has been for the last week.

Please understand that in no way am I complaining or looking for sympathy. I just want to let you know that I am so determined to be your obedient boy that I gladly suffer my frustration and desperation.