A new goal

During my last session of begging Ms Lee for permission to milk myself I mentioned that I felt tortured by the desperate desire to touch myself and I said that I thought I would be happier if she could completely eradicate the pigmale inside of me. She kindly agreed to help me and told me to learn how to milk myself through my prostate with out touching my penis or scrotum. She wants me to keep her appraised of my progress and let her know when I have reached the point where I can milk myself at will.

The very next day I began practicing to learn how to milk myself, using my ‘bigger tool’:

Fortunately there are many websites with information on learning how to milk yourself such as these:
prostate milking
forbidden art of prostate milking
pleasure mechanics

I must admit that I have mixed feelings about this new goal that Ms Lee has set for me. On the one hand I am looking forward to having the pigmale inside of me eradicated or at least harnessed for Ms Lee’s purposes. I believe it will please her greatly when I have learned how to milk myself and I am always anxious to find ways to please Ms Lee. But I am also concerned about the changes in my ‘sex life’ that achievement of this goal will bring about.

Ms Lee has not stated exactly how learning to milk myself will result in the eradication of the pigmale in me but I suspect that my opportunities for touching myself will be strictly limited in the future, if not fully eradicated along with the pigmale in me. It is the pigmale in me that creates the maddeningly frustrating desire to touch myself so if the pigmale is eradicated will the desire to touch myself also be eliminated? I suspect that Ms Lee will allow me to milk myself frequently but I don’t know if that will completely eliminate the desire to touch myself. Even if the desire for a release is satiated by my milking I may still desire to touch myself for the sheer pleasure that stroking an erect penis brings.

Of course stroking an erect penis is the act of a real man and Ms Lee has made it clear that I am not a real man. I am her property and permission to touch her property is only granted at her whim, if it pleases her. It is quite possible that once I learn to milk myself Ms Lee may no longer see any need to allow me to touch her property. I can’t begin to imagine what it would be like to no longer touch myself at all, nor what it would be like to only experience a release by milking myself with no touching allowed. But if Ms Lee expects this to become my new ‘sex life’ then I will be anxious to please her regardless of how significant the changes to my sex life might be.

I am not entirely sure how this will all turn out and I don’t know if Ms Lee will come right out and tell me exactly what she expects. She frequently likes to let me sort things out for myself, probably because I learn better that way.

Plugged again

I have become very focused on Ms Lee and her pleasure but she apparently thought that my focus on her could be improved. She recently told me that I was to wear my butt plug for at least 5 consecutive hours a day until my next session of touching myself. Although I have been using my butt plug during my daily morning Worship sessions it has been quite a while since I have endured it for anything near 5 hours a day so there was no doubt that Ms Lee’s latest expectation for me would be quite effective at improving my focus upon her.

My first day of being plugged for 5 hours was quite an ordeal. Within an hour or two of being plugged I was already feeling nearly unbearable discomfort as the plug tortured my rear. I knew I was walking funny and it was beginning to get difficult to sit down properly. By the third hour or so my poor rear was starting to sting from the rubbing of the plug and I was getting desperate to remove it. But no matter how bad I was hurting I was determined to be obedient and do as Ms Lee expected. I am always desperate to please her and I did not want to disappoint her on my first day of being plugged. When I finally reached the 5 hour point I promptly removed my plug, relieved to have the invader removed. I went to bed nearly exhausted from my ordeal and did not want to even think about wearing the plug the next day.

But the very next day I obediently did as Ms Lee expected and inserted my plug for another 5 hour ordeal of discomfort and distress. To make matters even worse I needed to mow my lawn that day. I have a large lawn and use a riding tractor which naturally vibrates quite a bit. As I bounced around on the tractor my plug kept getting rammed further up my rear and the vibrations of the tractor were driving me crazy. It felt like I was bouncing on top of a vibrating anal dildo. Normally riding the tractor makes me feel manly, but not when I’m chastised, plugged and pantied!

By the third day I was beginning to get used to wearing the plug but as the discomfort from the pain subsided I was presented with a new torment. It was getting to the point where the plug was teasing my poor penis relentlessly as it pressed against my prostate. As my penis strained against my chastity sleeve I felt a desperate pigmale desire to take Ms Lee’s property in my hands. My frustration was made all the worse as I felt my sissy ruffled panties embracing my chastised penis. Here is a photo of my plugged rear embraced by my white sissy ruffled panties:

As I got more frustrated and fought the urge to touch myself I began to squirm in my seat, causing my plug to press even harder against my prostate which in turn got me even more excited and frustrated. My plug was driving me crazy but I kept thinking about Ms Lee, hoping she would be pleased with my obedience. I also suspected she might be amused at my discomfort but I was glad to endure it if that pleased her.

I still have a few days to go before I will be allowed to beg to touch myself again. Even if my begging satisfies Ms Lee and it suits her whim to allow me to touch myself it frequently pleases her to delay the approval for a few days. This means I probably still have quite a few days of being plugged to look forward to. The good news is that this will provide me with many more opportunities to sharpen my focus on Ms Lee as I endure more discomfort and teasing for her pleasure.

Shaved again

I mentioned in my previous blog entry that Ms Lee’s expects me to always keep the area around my panties smooth and free of any unsightly fur. I have been working very hard to maintain a hair free appearance in this area but now Ms Lee has expanded the area where she expects this grooming to occur. In response to a recent photo of my panties that I sent to her she told me that there was some fur on my left leg that distracted from my prettiness. She then told me to correct this situation, asking me if I didn’t want to be her pretty girly boy.

I saw that there was indeed some fur on my left leg an inch or two below the edge of my panties. I was deeply disappointed with myself for offending Ms Lee with my unsightly fur again so I promptly shaved a large area on the front top portion of both legs so that no hair was visible anywhere near my panties. I sent a new photo to Ms Lee apologizing for my failure. I also assured her that I did indeed want to be her pretty girly boy even though it deeply embarrassed me to say so. I am beginning to feel like quite a sissy, wearing nothing but panties and not allowed to even touch myself without her permission. My embarrassment about being a sissy had recently been reinforced by a comment I had received concerning how I look wearing my panties:
requesting-feedback-regarding-my-panties

I was shocked when I received a response from Ms Lee informing me that I had addressed the wrong area. She had been referring to the fur that was visible on the outside of my left leg, not on the front. I had aggressively shaved the entirely wrong area for nothing! I could only hope that it amused Ms Lee that I had done so. I then shaved the outsides of both legs and sent her the attached new photo of my well shaved legs.

I was greatly relieved when Ms Lee informed me that she was pleased with the results of my shaving, saying that I looked much nicer. I do try very hard to look pretty for Ms Lee but I still struggle with the embarrassment I feel about being a sissy.

It just occurred to me that I forgot to mention that I had sent the initial photo I mentioned to Ms Lee as I was begging her for permission to touch myself (it had been a week since I had last touched myself). Although she did give me permission once I was properly groomed I realize that I had been much more concerned about offending her with my unsightly fur and making sure that she was pleased with my attempt to correct the situation. Obtaining permission to touch myself was an insignificant matter in comparison, as it should be.

The return of the sleeve

I recently made a big mistake by comparing myself to other men. I had been telling Ms Lee about the unbearable frustration I have been enduring and I said that I didn’t know how much longer I could go without tasting the sexual pleasure that most men get to enjoy at their leisure. At the time I was begging Ms Lee for my weekly permission to touch myself and I realize now that I should not have compared myself to other men in regards to their sexual freedom.

When Ms Lee responded to my begging She told me that she could see that I was really beginning to suffer but she had also noticed that I had made the mistake of comparing myself to other men. She reminded me that I was her property and that meant that I didn’t compare to other men. She then informed me that the consequence was that I was to put on my chastity sleeve and not remove it until she had given me permission. She also informed me that I had squandered my weekly opportunity to touch myself and I was to wait till the next week to beg again.

I had thought that I couldn’t possibly get any more frustrated but once more Ms Lee turned my world upside down and drove me deeper into submission to her. Although not being allowed to touch myself was extremely frustrating I at least got to enjoy the feel of an unrestrained erection like a real man. But I am not a real man, I am Ms Lee’s property and now I no longer get to even enjoy erections, much less touch myself.

I had also forgotten just how difficult it was to put my chastity sleeve on. (Those who are not familiar with my chastity sleeve can check some of the past postings about it: Chastity sleeve postings).

It is a major struggle to get my sleeve on, especially since my deprived penis gets quite excited from the handling required to get it in the sleeve. Once in place my sleeve performs an extremely effective job of preventing anything approaching a full erection. And when my naughty penis does try to become erect it is severely punished by the chains holding the sleeve in place. Those chains cut in deeply whenever my penis makes a futile effort at becoming erect.

The photo below shows my penis restrained by my chastity sleeve. This is a homemade sleeve which has the advantage of being unnoticeable under my pants. The tightness of the restricting chains is also easily adjustable, a feature which Ms Lee has used to her advantage. She has at times enjoyed having me remove links to make my sleeve even tighter but she has never allowed me to add any links back once they have been removed. Anyone who is interested in how my sleeve is fashioned can check out this posting – Ms Lee’s Chastity Sleeve

You might notice in the photo below that none of my fur pokes out from beneath my panties. I have previously made the mistake of presenting myself to Ms Lee with some random hairs showing and every time She has me correct my error, removing even more. Ms Lee does not like to see any fur showing from beneath my panties so I am always carefully grooming myself. Some of my panties are fairly skimpy and at this point I have removed quite a bit.

Double Release

Within the last week Ms Lee has generously allowed me not one, but TWO releases. The first time was after I begged twice for permission to touch myself after going another full week abiding faithfully to her no touching rule. The first time I begged she was not impressed and told me that I could do better. I then proceeded to beg much more sincerely & desperately and was greatly relieved when she told me that I could touch myself with no restrictions except that I could only do so between 5 and 5:30 PM on Sunday.

It turned out that I was on my way to the shore for a vacation that day and as luck would have it I was on the road at 5PM. I desperately looked for a rest stop and finally found one with 5 minutes to spare. I rushed into the crowded mens room and began wanking feverishly inside a bathroom stall. I was extremely self conscious due to all the people nearby, worried that someone would know what I was doing. Due to my nervousness I was barely able to produce a small amount of cum with just a minute or two to spare. I was mortified, but at least I had enjoyed a pleasurable release.

The next day I was overjoyed when Ms Lee informed me that she was impressed with my obedience and would generously allow me another release with no restriction other than it must occur on Tuesday. I thanked Ms Lee and informed her that I had been working very hard to be an obedient boy, hopeful for the reward which she had just granted me. I also told her that the reward I had been hoping for was to please her with my obedience, providing her with pleasure and satisfaction. I had neither expected nor been looking for another release so soon and was quite surprised with her generosity.

I was not able to obtain the privacy I needed until late in the day but I then enjoyed a glorious pleasurable release, this time with no pressure or concerns. I was truly grateful to Ms Lee for being so thoughtful.

Ms Lee Takes Her Property Back

After a very long absence I am bringing this blog back to life. My status with Ms Lee has undergone a number of changes over the last couple of years but recently she has taken me back as her strictly controlled property, with a number of new expectations. One of those expectations was that I resume weekly updates to this blog, without fail. I am quite aware of the severe consequences I would suffer if I failed to meet one of Ms Lee’s expectations so you can expect that my updates will be regular and timely.

This morning I got on my knees to thank Ms Lee for taking me back as her strictly controlled property. It will be difficult to adhere faithfully to all of her expectations but I am firmly committed to doing so, no matter how hard or frustrating it may be. Her no touching rule is especially maddening. My penis is straining against my lacy white panties as I type this, squirming in my seat in desperation. I don’t think words can properly describe just how stressed I am right now as I fight the battle to resist the urge to take her property in my hands. At present she has not required me to wear my chastity sleeve which in a perverse way makes things even more frustrating. My sleeve had always prevented me from enjoying anything near a full erection but now I must endure the incredible frustration of experiencing a rock hard erection that I am prohibited from touching.

It is particularly difficult in the morning when I wake up with a morning erection and feel the natural, naughty urge to masturbate like a little school boy. But as I awaken further I feel the overpowering frustration that comes with remembering that I am not allowed to touch Ms Lee’s property without her permission. I then must struggle against temptation as my deprived penis strains like mad inside my frilly panties. My panties add a nasty twist to my frustration as their silky caress of my penis teases it mercilessly. One of Ms Lee’s new expectations is that I no longer wear any male underwear at all. Nothing but frilly and lacy panties are allowed.

Before Ms Lee had recently taken me back as Her firmly controlled property I had fallen back into the naughty habit of frequently masturbating at will, sometimes multiple times a day. Ms Lee put an immediate end to my naughty pleasures and it has now been a full week since I last masturbated. It has been a major shock to go this long without cumming but I am grateful to Ms Lee. I understand that my lack of willpower regarding masturbation and playing with myself means that I need the firm control that Ms Lee has graciously provided me with.

Ms Lee has also generously given me permission to touch myself and masturbate on Wednesday morning, between 6 and 6:30 AM. She expects me to ruin my release by squeezing the tip of my penis to prevent the pleasurable explosion of cumming which will probably result in a frustrating dribble of cum, preventing me from enjoying the wild, free release a real man would experience. However I feel extremely grateful as I did not expect her to allow a release so soon at all. I will then not be allowed to touch myself again until I properly beg her again for permission. I am planning on waiting at least a week before doing so as I want to be in the proper state of mind to beg her with sincerity.

I actually could probably beg quite sincerely the very next day but I am hopeful that it will please Ms Lee if I endure an entire week of intense frustration before I bother her with the insignificant issue of my sexual pleasure. My focus is solely on her pleasure and my sexual pleasure is completely dependent on her whim and mood. In fact I am desperately hopeful that she will be pleased with my frustration as I doubt I would be allowed any sexual pleasure at all if my intense desperation did not please or amuse her.

Ms Lee’s panty washing boy

Recently I have assumed responsibility for washing Ms Lee’s panties. I am embarrassed to admit that I actually had to beg her to allow me this honor. I am not sure if she doubted my ability to properly clean her panties or if she suspected I might just be anxious to handle and sniff the panties that had embraced her gorgeous derriere (perhaps both). I have to admit that my penis strains like crazy against my chastity sleeve whenever I am washing Ms Lee’s panties. I also get quite excited by the wondrous aroma that exudes from her worn panties but I would never dare molest them in any way (Ms Lee had previously warned me that I would be punished if I ever did so).

I finally convinced Ms Lee to give me a chance to demonstrate I could clean her panties to her satisfaction but first I had to diligently study how to properly clean a woman’s delicates. I was actually red in the face as I browsed the online site of Better Homes and Gardens for panty washing instructions. I had often noticed that magazine on the kitchen table as I grew up and I never suspected that one day I would be studying it like a good, obedient housekeeper.

By the time I had convinced Ms Lee to allow me to wash some of her panties I had studied over half a dozen sites on panty washing and had practiced on my own. I was glad I had done so because I learned quite a few things that I had been neglecting in the care of my own panties. Although I had always hand washed them I had been fairly careless about it. I have now established a twelve step procedure for washing Ms Lee’s panties as follows:

1) Fill sink with cool water. Warm or hot water would clean quicker and be easier on my hands, but could shrink the panties.

2) Add one capful of Woolite fabric cleaner, stir water well to mix

3) Dip panties into water and let soak for 5 to 10 minutes

4) Rub panties gently to loosen dirt and stains, let soak for another 5 to 10 minutes

5) Rub panties lightly, but thoroughly to clean completely. Examine carefully to make sure any stains are removed

6) Drain sink and rinse panties under running, cold water

7) Fill sink with cold water again and swirl panties under the water to clean more soap out of them

8) Drain sink and rinse panties under cold water one more time to make sure all soap is gone

9) Squeeze panties gently to remove excess water, do NOT wring. That could misshape the panties

10) Lay panties on a clean, dry white towel, roll up gently within towel to remove more water

11) Lay panties flat on another clean, dry white towel for drying

12) Turn panties over occasionally for next day or two until dry

The process I have developed involves quite a bit of time and work but so far Ms Lee seems pleased by my efforts. I hope that she enjoys having one less thing to worry about, knowing that she will always have perfectly clean panties available. I am so glad that I have been able to perform this menial task for her and I am thankful she allowed me the opportunity to demonstrate that I could clean her panties in an acceptable manner. I am always desperate to find new ways to please Ms Lee and I am hopeful that she will allow me to continue to be her faithful panty washing boy.

Of course I must also admit that it gives me a thrill to know that throughout every day Ms Lee is wearing a pair of panties that I have worked so diligently to wash. I hope that once in a while she smiles, enjoying the fruit of my labors. But somehow I suspect that more often she just takes her freshly laundered panties for granted, not even having to bother thinking about all the toil and dedication that went into keeping them immaculately clean.

My shrinking penis

Ms Lee seems to enjoy having my chastity chains severely tight. As I mentioned in a previous posting, she had me shorten them by a link each to correct me for having an unauthorized release. Initially this was to be for a period of a single week, but that was extended for another week when I asked if it would please her to extend my correction. This cycle was repeated until finally she told me that I should just extend my punishment thru the rest of the summer.

As Labor Day approached I sent her an email describing the torments that my tightened chastity chains had inflicted on me. Here is a copy of that email:

The last time I begged you to allow me to please you by extending the time I wear my tightened chastity chains you told me to do so until the end of summer. As the end of September approaches I realize that I am not sure if you consider Labor Day the end of summer, or September 21. Regardless, I am now on my knees begging you to allow me to continue enduring my viciously tightened chastity chains until the official end of summer on September 21.

Please do not grant my request unless it will please (or amuse) you. Although I have to admit that I am perversely excited by the pain of the tightened chains I can assure you that I am not enjoying my predicament. Although I have done my best not to complain to you, I am actually enduring a considerable amount of suffering. I have gladly done so because i desperately desire to please you and I am hopeful that I can continue to do so.

Below is a list of the various ways my tightened chastity chains are affecting me. Please understand that I am not complaining in any way or asking for leniency. I just want to make sure that you are aware of the full extent of what I am enduring in the hope that you might derive more pleasure from my situation.

– My penis is constantly crushed by my tightened chastity chains

– I have to sit down and pee like a girl because the chains are so tight that my pee continues to dribble out for a few minutes after I urinate

– By the end of each day my punished penis is raw and red

– At times my tightly chastised penis feels like it is being burned, I feel an intense stinging that will not quickly go away. When this happens I endure the pain by thinking about your pleasure

– Erections hurt even after I remove the chains at bedtime. The deep impressions inflicted on my poor penis continue to cause pain as if the chains were still in place

– I realize that the viciously tight chastity chains are conditioning me to prefer anal pleasure since any attempts to enjoy an erection are instantly corrected by the bite of the viciously tight chastity chains

– When my tightly chastised penis does attempt an erection it is barely able to achieve 4 inches in length. And of course it is restricted to less than an inch in thickness. This is quite humiliating and I am really beginning to wonder if my extended, severe chastity might actually be causing my inadequate penis to become even smaller than it already is

Once again I am on my knees begging you to allow me to continue enduring my tightened chastity chains. I sincerely hope it will bring you some pleasure and perhaps bring a smile to your lovely face.

In my 67th day of chastity for your pleasure,
my 67th day of enduring my shortened chastity chains,
135 days since my last pleasurable release,
and wearing my black lace panties with pink trim today

Although I would have gladly continued enduring my tightened chastity to please Ms Lee I was relieved when she told me that it would not be necessary to extend my punishment beyond Labor Day. That night as I removed my chastity chains before going to sleep I discovered that the effects of my viciously tightened chastity would continue. Here is the message I sent Ms Lee the next morning concerning this:

I hope your toes were curling in your sleep this morning as I thought about pleasing you with a long, sensuous foot massage. I would caress your lovely feet and rub each individual toe, kissing them as I moved on to the next. Before I started I would light an oil warmer so I could rub the warmth into your feet. I would also have candles lit and some of your favorite music playing to help you relax and enjoy the pampering. I would set out some plants and light some incense if you liked. I would always be trying to think of small new ways to maximize your pleasure.

I do hope you have a lovely morning and a wonderful day today.

I was also thinking of you last night after I removed my chastity chains as my desperate penis became painfully erect. I’m not sure if it got excited as a result of my touching it as I removed the chains or if it was the anticipation of the loosening of the chains (perhaps both). As I watched my penis becoming erect I once again thought it looked smaller than in the past. I was shocked when I took a ruler and laid it against my penis to check. As you can see in the attached photos, my erect penis is now less than 5 inches long! When I measured it a couple of years ago when I first fashioned my chastity sleeve I remember that it was a full 6 inches long. I can only assume that wearing my severely tightened chastity for so long has reduced the length of my already inadequate penis.

Even 6 inches is nothing to brag about, but it is incredibly humiliating to realize that my penis has shrunk so much smaller. Do you think it might get longer again once my chastity chains are loosened? I can’t imagine that adding back a single link to only four of my chains is going to restore a full inch back to my shrunken penis. I hope that in time I regain some of my lost length. But if it turns out that my penis has been permanently shrunk I sincerely hope that it provides you with some pleasure and satisfaction, or at least some amusement.

Correction extended

It was extremely painful & frustrating to endure an entire week with my chastity chains tightened so viciously. Even partial erections were out of the question as the chastity chains promptly rewarded any such attempts with a painful bite. As the end of my week’s correction approached I truly looked forward to returning to my regular, looser chastity chains. I knew I would be greatly relieved, but it occurred to me that Ms Lee might be disappointed. She seemed to be greatly enjoying my suffering and frustration. I suspected that it pleased her very much to know that my penis was constantly suffering for her pleasure. As I thought about this a bit more I realized that I should only be concerned about the opportunity to please her, my own discomfort and frustration were irrelevant. Here is the message I sent to her as the end of my correction approached:

I hope that you are doing well and enjoying your new job. I also hope that you have a lovely day.

As of today I have been enduring the intense pain of my shortened chastity chains for an entire week. At times the pain has been excruciating and as I recently reported I no longer can pee while standing up like a man. Instead I must sit on a toilet. I am now back on my knees thanking you for taking the time to correct me for coming without permission. I certainly believe I have learned my lesson well and I will be very careful to avoid accidental, but unauthorized releases in the future.

I also believe (hope) that my situation and correction have pleased you. Although I desperately desire to return to my longer chains I am more desperate to provide you with further pleasure, or at least some additional amusement. I am still on my knees as I beg you to consider allowing me to extend the length of my correction by a period of your choosing. Please let me know if it would please you for me to do this and if so, for how long.

I could picture the smile on Ms Lee’s face as she responded by asking me if I ever thought I would actually beg her to continue the torture my penis was enduring. Then in her typical fashion of inflicting a major impact on my existence on a momentary whim she briefly mentioned that another week would do just fine.

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.