Archive for the ‘Chastity sleeve’ Category

Permission to masturbate

June 11, 2012

Yesterday Ms Lee surprised me by giving me permission to masturbate. I have been in chastity for nearly two months while faithfully abiding by her no touching rule, so I was quite excited as I read her message:

When you get this email, at first opportunity today, and today only, remove all chains. Plug up. Remove sleeve. Masturbate & edge, then back off. Keep edging & backing off (no ejaculation at all) for 20 minutes. When done, you may use the plug to try and cum, but use the plug and the plug only. You may touch the plug, but can no longer touch your penis. When done, put the sleeve & chains back on.

Needless to say, I did exactly as Ms Lee expected, even though it was incredibly frustrating. When I was finished I immediately sent her a report on my experience:

I am on my knees right now thanking you for providing me an opportunity to masturbate, even though I was not allowed to release while touching myself. After 57 days in extended chastity, and abiding by your no touching rule, it was deliciously frustrating to be allowed to edge, but not to ejaculate.

I was out when I received your email and my penis strained against my chastity sleeve like crazy as I anticipated how awesome it would be to actually touch myself in a sexual manner. When I finally got home and had some privacy I quickly removed my chains, inserted my plug and removed my sleeve. As I took hold of my penis and began to stroke it I began to understand just how torturous it would be to edge for 20 minutes while ejaculation was prohibited. In less than a minute I had to stop stroking for fear that I might release my huge load of build up cum already. My penis twitched and shook from the intense teasing as I struggled to control myself. I desperately wanted to grab hold of my penis and masturbate like a mad man, but I was determined that I would not disappoint you by allowing an unauthorized release.

I probably wasted at lease a minute waiting for my deprived penis to calm down enough so that I dared to begin stroking again. Once again I had to stop well before another minute was up as I felt my unruly penis begin to twitch again. I was tortured by the realization that I was spending much more time desperately fighting for control than I was enjoying my brief opportunity to enjoy touching myself. I tried slowly rubbing my shaft, but within seconds I was masturbating furiously again, almost losing control as I reluctantly released my penis and watched it twitch once more.

I continued this frustrating cycle, alternating between very brief periods of delirious sexual enjoyment separated by much longer periods of desperately fighting to control my pigmale desire to release explosively. As I glanced at the clock I realized that I had already squandered well over half the time you had generously allowed me to play with myself and had only managed a few minutes of actual masturbation. Perversely this only caused me to stroke more furiously, quickly reaching the point where my twitching penis forced me to stop again.

All too soon I reached the final minute of my masturbation allowance and I desperately tried to control myself so I could enjoy it. Unfortunately I almost immediately began twitching again and reluctantly had to stop once again. I almost cried as I saw the clock reach the twenty minute mark, realizing that I was no longer allowed to touch myself.

The next portion of your generosity was even more frustrating as I tried to milk myself with my huge Worship plug. I desperately wanted to stroke myself as I did so, but my no touching training effectively prevented me from doing so. I was being driven insane as I gyrated like crazy, but was unable to produce. Soon I was ramming the plug into my rear, imagining you taking me with your strap on. I kept up in this manner for quite a while and finally collapsed in exhaustion, realizing that the plug alone was not enough to get me off.

I then removed the plug, cleaned myself up and put the sleeve & chains back on. That nasty fifth chain bit viciously as it eliminated the last of my erection and returned my poor penis to extended chastity.

It is so much harder to resist the urge to touch myself now that I have been reminded how pleasurable it is to masturbate. I am almost glad that the fifth chain is back in place, firmly enforcing your no touching rule.

Once again I am back on my knees thanking you for this opportunity. I hope it pleases you that I remain in faithful chastity for your pleasure.

A couple of hours later I realized that my deprived penis had released a small bit of cum. It was nothing like a full milking or ruined orgasm, it was more like a pathetic leakage that did nothing but frustrate me even more.

The eradication of erections

June 3, 2012

It has been a week since I was informed by Ms Lee that she expected me to resume wearing the viciously tight fifth chastity chain on my sleeve. I am beginning to think that the one week reprieve she granted me was a rare exception, a kindness granted on her whim, and not something I should expect again in the near future. I think I had better get used to enduring the daily struggle of enduring the nasty bite of that chain every time my frustrated penis makes even the slightest attempt to enjoy an erection.

I am now beginning my eighth week of severe chastity for the pleasure of Ms Lee and my penis is incredibly desperate for release. Whenever I have been in extended chastity in the past, my penis has frequently strained against my chastity sleeve, bulging out between the chains. This would make me extremely desperate for sexual stimulation and tempt me very badly to touch myself in violation of Ms Lee’s no touching rule.

Things are very different now that the fifth chain is enforcing Ms Lee’s expectations. Whenever my penis makes a futile effort to become erect the nasty fifth chains digs in deeply, preventing even the slightest attempt at getting hard. If my unruly penis continues to strain against the sleeve the fifth chain digs in even deeper, inflicting a very nasty bite and reminding me that Ms Lee expects me to remain in obedient chastity. Before long my penis learns its lesson and gives up the attempt to enjoy an erection. My penis’s continuous, rampant straining against the sleeve has become is a thing of the past.

In a perverse way I used to enjoy the feeling of my penis straining against the sleeve, at least experiencing a partial erection. While enjoyable, I would be incredibly frustrated and distracted by my pigmale desire for a release. Now the fifth chain has eliminated the possibility of enjoying even a partial erection and my frustration continues unabated.  I realize one reason why it probably pleases Ms Lee to have me properly restrained by the fifth chain is that I am no longer distracted by my penis straining against the sleeve. Instead I feel it feebly throbbing in humble submission to her and I focus on thoughts of devotion to her pleasure. While I no longer experience any pleasure from partial erections I am hopeful that the suffering inflicted by my fifth chain somehow pleases Ms Lee, demonstrating my faithful obedience.

Severe chastity continues

May 30, 2012

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

May 11, 2012

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

May 5, 2012

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.

The fifth chain

April 25, 2012

For a few days now I have been enduring an extremely tight fifth chastity chain that I have attached to my chastity sleeve. This new chain is quite painful at times, stinging as is bites into my firmly restrained penis. However, as I explain below, I feel this increased level of chastity control is necessary and will insure that I adhere faithfully to Ms Lee’s no touching rule.

Here is the message I sent to Ms Lee explaining why I felt I needed the additional chain:

I hate to bother you again and risk annoying you with my trivial frustrations, but I feel I should let you know that my level of desperation is reaching even more incredible heights. For a year now I have been experiencing extended chastity periods and my level of frustration is nearly unbearable. My penis seems extra sensitive now and my panties are teasing it like crazy. I can’t stop straining against my sleeve and I frequently find myself grinding my rear against my seat. As you expected, I have not been using my anal dildo or plug during Worship and my rear is feeling quite neglected.

I have been so desperate lately that I have been worried that I might be tempted to touch myself again. I can’t conceive of disappointing you in such a way so for now I have added a fifth chastity chain to my sleeve. The four I normally use have allowed my penis to become partially erect between the chains which is driving me crazy with sexual desire. The partial erections result in my poor penis looking like some kind of restrained sausage and they are quite distracting.

To more firmly restrict my naughty penis I used one of those milking chains I had fashioned previously. It is a couple of links shorter than my normal chastity chains and digs in quite painfully whenever my misbehaving penis attempts a partial erection. I secured it at the end of my penis, right behind the head. So far I have found this addition to my chastity to be quite effective, with the tempting partial erections now eradicated (although my penis continues to strain frequently against the chastity chains). My penis is now very firmly restrained and in full submission to your will. I will continue to wear this fifth chastity chain until you tell me otherwise.

A just punishment

April 18, 2012

Recently Ms Lee gave me a very firm reminder that I must always be a good, obedient boy for her. My lesson began when I briefly lost control of myself and allowed my pigmale desires to get the better of me. One morning during Worship I was so frustrated and desperate that I found myself lightly rubbing my penis. It was futile since I was wearing my chastity sleeve and I stopped when the pain of my penis throbbing against the chastity chains became too great. I then felt quite guilty and dutifully reported the event to Ms Lee. I expected her to be disappointed with me and thought that she might punish me, but I had no idea just how severe her punishment would be. This is how I reported my transgression:

I’m glad that it does not bother you that I constantly tell you about my frustrations and desperation. It drives me crazy that you did not even respond to my begging to be allowed to wear my plug. I remember how deviously pleasurable it was to experience the plug filling my rear and teasing my penis so much that it would strain uselessly against my chastity sleeve. It frustrated me badly, but like now I was so starved for any sort of sexual stimulation that I gladly endured the discomfort.

This morning I once again gyrated like mad as I thrust my anal dildo in my rear as I attempted to milk myself. Once again (possibly due to recent stress) I was unable to produce anything more than a slight dribble. And right now I am on my knees begging you for forgiveness because during this morning’s session I gave into temptation and touched myself while using my anal dildo. I did not masturbate, but I did rub myself with a couple of fingers. I had to stop when the pain of my chastity chains digging into my penis became too much, but I feel quite guilty about this wanton behavior ( I don’t use my sleeve to protect my penis while milking myself and it doesn’t usually get too hard then anyway, the focus is on my rear and prostate).

I am now safely in my sleeve (and chains), but I continue to squirm in my seat in desperation while my rear clenches against emptiness. I am so frustrated, and so sorry if I disappointed you.

In my 46th day of chastity for your pleasure,
Wearing my first pair of purple panties today.

Ms Lee’s displeasure with me was quite clear in her response:

I am very disappointed.  In all the months and years we’ve known each other, you’ve not disobeyed me.  I am not happy about being put into this position.  Do the following and respond to this email acknowledging your submission to my wishes:

(1) 1500 word essay stating the importance of obeying and being a good boy.  Due Tuesday night, absolutely no extensions or exceptions.
(2) Send another tribute, immediately.
(3) Punish your rear and your penis with a tool of your choice.  I want your rear black and blue and your penis very well-striped.  Send pictures and I will let you know if sufficient.
(4) No touching, no plug for morning worship, just chastity, until I tell you otherwise.



March 7, 2012

As reflected by my abscense from posting, hectic times have continued for me. Fortunately, Ms Lee has continued to grace me with her attention and expectations, which helped me to continue on.

Ms Lee seemed determined to have me learn my lesson about the sexual frustration women endure, so I remain plugged for 2 entire months. Every day I had a firm reminder of Ms Lee as the pressure against my prostate caused my penis to strain in futility against my chastity sleeve.

Twice I was surprised when Ms Lee allowed me pleasuable releases. Ms Lee can be quite kind, depending on her mood and whim, however I am still averaging less than one release per month so far this year.

At the beginning of this month Ms Lee surprised me again when she sent me this message:

Hi and happy March!  So today as soon as you read this, I’d like you to remove everything, including your chastity sleeve.  Still no touching, but nothing, not even during morning worship. Nothing. No plug, no panties, no dildo, no touching, no nothing until I tell you otherwise.

At first I thought I would enjoy the freedom from the plug, panties and chastity, but soon I realized just how deeply Ms Lee has conditioned me. Every day I felt like something deep inside was missing. I felt naked without my panties & chastity sleeve and was tormented by unfettered erections that I was not allowed to touch. I reported my experiences to her:

I actually feel empty today without my anal plug. I find myself
clenching the muscles in my rear, but there is nothing to press
against. I miss the sensation of the plug pressing against my prostate
and exciting my chastised penis.

And I truly missed using my anal dildo this morning. After 10 days in
chastity the pressure is building in my prostate. I had grown used to
using the anal dildo to ‘scratch that itch’, but now all I can do is
clench my rear and feel my penis strain in frustration.

I know I will be thinking of you frequently today. Not because of the
anal plug in my rear, but perversely because it is missing.

Ms lee then surprised me again by responding:

Lol…wow.  Happened quicker than I thought.  Ok, experiment over.  Go ahead and panty again, plug up for worship, etc, etc.

Yesterday morning I gave Ms Lee a report on my return to panties & chastity:

This morning I also enjoyed using my anal dildo. However, as always I
was tormented by the long, slow buildup to the teasing edge of sexual
pleasure. I am never able to reach the point of true, intense pleasure
like I used to enjoy when I masturbated. Instead I hover at the edge,
close enough to know what I am missing, but denied any hope of a real

In my 15th day of chastity for your pleasure,
Wearing my red panties with garters

Back to ‘normal’

January 22, 2012

Lately I have been distracted by some personal issues as well as a backlog of chores left over from the end of year holidays. Fortunately things have recently returned to a more ‘normal’ state of affairs. I commented on this in a message to Ms Lee:

Now that things have somewhat returned to ‘normal’, I was able to
enjoy an unrushed Worship session this morning, followed by another
attempt to milk myself. While I was unable to produce anything I found
it pleasurable (in a different way) just to be able to relax and
experience the sensation of rubbing the anal dildo against my
prostate. The sexual pleasure was nowhere near as intense as normal
male masturbation, but nevertheless I find myself looking forward to my
milking sessions.

I am still experimenting and learning how to adjust to deriving my
sexual pleasure solely thru my rear. Lately I’ve been using my anal
muscles to grip the anal dildo during my milking sessions, hugging it
as it slides in and out, trying to pull it in deeper and harder. Just
thinking about that has me doing the same thing right now with my anal
plug, which is quite frustrating, causing my penis to strain against
my chastity sleeve.

In my 14th day of chastity for your pleasure,
my 12th day of being plugged
and wearing my pink panties today

Begging to be plugged

November 27, 2011

Today is my 48th day in chastity and my desperation is reaching new peaks. My deprived penis is now almost constantly straining against my chastity sleeve and I am finding it quite difficult to concentrate on anything other than my submission to Ms Lee.

This morning’s Worship session was another exercise in extreme frustration. I am now badly craving my daily opportunity to ram my huge Worship plug up my rear in a pathetic attempt to experience what little sexual stimulation I am allowed. Once again I gyrated like mad on my plug and exhausted myself by the time my session was completed.

As always I ended my session by giving thanks to Ms Lee for keeping me on. As I was doing so I resolved to ask her if it would please her to allow me to once again wear my plug for an entire day. At this extremely extended point in my chastity I don’t know if I could stand the teasing and frustration that wearing the plug all day would inflict on me, but my desperation is getting the better of me.