Ms Lee’s pleasure

Although I was growing increasingly desperate as the legnth of my chastity increased I reminded myself that everything would be fine as long as I concentrated on Ms Lee’s pleasure. That is truly all that matters to me and I know that she will always see to my needs. On my 54th day in chastity i sent her this message:

I’m  excited that I was able to purchase the dildo harness for you. I hope you will be pleased with it, it looks really cool.

I’m also glad to hear that you have continued to enjoy my extended chastity. I am quite focused on your pleasure and I sincerely hope that the thought of my being in extended chastity, without even being able to enjoy erections, brings an occasional smile to your face.

You will see an example of how focused I am on your pleasure when I send you a photo of myself in today’s panties (my extremely skimpy pink & black thong). When I was getting ready to take the photo I noticed that I still had quite a bit of fur poking out from beneath my panties. It immediately occurred to me that you would not be pleased with my appearance, so I trimmed a good deal of the excess fur off for you. I hope you are happy with my newly trimmed look.

You may also notice in the photo just how frustrated and desperate I am at this point. My penis is constantly straining like mad against the tightly restraining chastity chains, keeping you always on my mind. Every time I feel my penis strain I find myself thinking that I should be worshiping you and thanking you. I am always compelled to think about worshiping at your lovely rear, demonstrating my submission and devotion. It would be so nice to reach around you and caress your awesome breasts as my tongue reached deeply inside you. I would play with your nipples until they were hard and excited, all the while thrusting my tongue deeper and faster. I wouldn’t stop until you were spurting and coming, and I wouldn;t stop then. I would instead pick up the pace and make you cum again. I would force my exhausted tongue to continue my worship as your pleasure became the center of my universe.

Right now I can feel my penis straining in futility as I contemplate your total control over me and my sexuality. I have passed the point of maximum desperation and desire for a pleasureable release. I understand that instead, the best I can hope for is that you may consider allowing me to milk myself to releive the pressure in my balls. I am back on my knees where I belong, begging you, pleading with you, to please allow me to milk myself. I can’t begin to describe just how desperate I am.

As I am begging, I find myself drawn back to focusing on your pleasure. I know I shouldn’t be so concerned about my own desperation. Instead, may I ask if there is anything else I can do that might please or amuse you?

In my 54th day of chastity for your pleasure

In reply, Ms Lee sent me this message:

Why am I not seeing you sufficiently beg on a daily basis?  You must not need it that much.

Begging again

Ms Lee had told me that I could not beg for a milking until I purchased her dildo harness for her.  After I told Ms Lee that I had sent her the dildo harness she very graciously replied:

You may begin begging at any time.  I will consider them all AFTER the harness arrives

I wasted no time in beginning to beg again for a milking:

Thank you so much for allowing me to begin begging for a milking at this time. I understand that you will not consider a response to my begging until after your harness is in your hands. And you are very, very welcome – I am happy that you allowed me this opportunity to purchase something that will please you.

I am now on my knees to begin my begging for a milking. Of course I am wearing my flowered panties as required by my panty schedule that you provided me with. And my deprived penis is firmly restrained by my chastity sleeve, as it has been for the last 35 days. Thus not only have I been denied a release for 53 days, I have not even been allowed a full, unfettered erection since you told me to resume wearing my chastity sleeve for you a little over a month ago. With one exception – you did have me masturbate (without release) that one time on June 3rd, just over a month ago. That caused me such intense frustration and the memory of it continues to do so.

I have also been thinking quite a bit about the fact that you will not even consider a response to my begging until you receive your harness. That means I will reach 2 MONTHS in chastity for you at a minimum. I knew that you loved the idea of extended chastity, but I had no idea that you would ever take it this far. I am in awe of you and your control over me, and quite frankly a bit frightened. But most of all I find myself being drawn into ever deeper submission to you. It is obvious that your dominance is serious, severe and extremely intense.

As I have repeatedly mentioned, the pressure in my balls has become quite intense. And of course that causes my penis to almost constantly strain against my chastity sleeve in a futile effort to acheive the erection I am denied. This all keeps you ever present on my mind and adds to the intensity of my submission to you.

As a result of my desperation and frustration I am begging, no PLEADING! for permission to be allowed to milk myself to releive the pressure in my balls. Please, please consider my request as I am frustrated beyond comprehension.

I also beg you to allow me to use the milking chains I fashioned if you allow me to milk myself, I realize that it may please you to deny me the pleasure of an erection if I am allowed to be milked and of course the milking chains would also likely prevent me from even enjoying a normal, explosive release. Instead, all I am likely to gain from a milking is to releive the pressure in my balls (and my prostate). I have never been milked, but I suspect that my frustration will continue unchecked since I will be denied any sort of enjoyable ejaculation. Instead I expect that my semen will just drip out of my firmly restrained penis.

Once again, I beg you to please consider allowing me to milk myself while wearing my milking chains. I would be ever so grateful!

In my 53rd day of chastity for your pleasure

No fireworks for me

As I watched the fireworks on the 4th of July I felt a twinge in my balls every time there was a blast of sound and light. I couldn’t help being reminded of the fact that I hadn’t exploded in orgasm for nearly two months at this point. The next morning I sent this message to Ms Lee:

I hope you had a very nice Fourth of July holiday. I was thinking of you quite a bit last night. Every time I saw the fireworks explode I was reminded of my restrained penis that is doing nothing of the sort. I am absolutely astounded that I have now gone 53 days without a release. I would never have believed that I could go so long, but I am determined that I will not disappoint you and so I will not release until it pleases you. I also understand quite clearly what else I need to do for you and of course I will accomplish that as soon as possible.

Furthermore I understand that I will then have to beg quite convincingly in order to convince you how truly desperate I am for a milking. I have given up on dreaming that you might actually let me have an unfettered, full blown release any time in the near future. Instead I will devote my opportunity to beg to making sure I demonstrate my sincerity and desperation for a milking to release the pressure in my balls.

Although I am not allowed to beg for a milking at this time I do dream,of kneeling down and kissing your beautiful rear. I desperately want to please you by worshiping you in that manner, sliding my tongue deeply inside you as I rim you to orgasm after orgasm. It would be such a delicious contrast to have you enjoying such sexual pleasure, provided to you by your devoted boy who has now been in chastity for nearly two months for your pleasure. Every time you moaned in pleasure I would feel my penis strain against my chastity sleeve. I would concentrate on nothing but your pleasure, not expecting any sort of release in return. My opportunity to release depends solely on your whim and mood.

In my 53rd day of chastity for your pleasure

A Decision

While I was busy fashioning my milking chains and becoming anally obsessed I was not begging for my milking frequently or seriously enough. Ms Lee brought this to my attention with this message to me:

I’ve come to a decision on your begging with regard to your chastity, my love.

My decision is:

1)  Your begging was not sincere and no where near showing a need.

My remedy is:

1)  Get me that harness I emailed you the link for on a strapon, ASAP!  Contact me for an address when you do, because I may have moved or be near moving.

2)  Once I have the harness–in hand–I will then entertain again your begging me to be milked.

i realized that Ms Lee was absolutely correct and immediately replied with my apology:

I must apologize that my begging for a milking was not sincere enough and did not come close enough to showing a need. I assure you that after more than a month and a half in chastity for your pleasure I am experiencing extreme need and desperation. My penis constantly strains in futility against my sleeve and you are always on my mind.I will obviously be in chastity for a week or two more at a minimum. I understand that purchasing the harness for you is merely a prerequisite required before you will even allow me to beg for a milking again. And of course I will then have to do a much better and more sincere job of begging when I am allowed to do so again.While I am not allowed to beg for a milking at this time I would like to beg for forgiveness. I would like to get on my knees and apologize. While I was on my knees I would kiss your feet until you told me to stop. Then I would ask if I could humbly kiss your rear so I could demonstrate how sorry I am.

This would not be a sexually exciting (for me at least) rimming that I would perfrom, rather I would reverently kiss and worship your rear. My tongue would lick and caress without rest, at times touching lightly, at times reaching in deeply. If you chose to sexually enjoy this rimming I would continue until you were satisfied, without pause. At no time would I allow myself to get sexually excited or try to enjoy myself. My purpose would be to demonstrate my sorrow and to please you.

In my 48th day of chastity for your pleasure

Losing Count

My days in chastity continued to mount until at one point I sent this message to Ms Lee:

I was so busy yesterday that I didn’t notice my penis straining against my sleeve too often. However, right now I feel it attempting in vain to gain an erection, but of course my sleeve refuses to allow anything of the kind. I’m also surprised that I can’t say exactly how many days I have been in chastity at this point. I do know I have blown way past my previous record, but I’d have to go back to my previous emails to figure out where I am. However, you didn’t seem to be impressed by me setting a new chastity record, so perhaps I shouldn’t bother you with keeping count of the days.

Ms Lee had indeed informed me that she was not impressed by how long I had been in chastity for her. However it seems that perhaps she was at least amused by my situation since she sent the following message in reply:

Do go through your prior emails & figure out how many days.  I like the count.

I then dutifully calculated how long I had been in chastity and reported back to her:

Today is my 47th day in chastity. I can’t believe I have made it this far. But now that I am wearing my sleeve and communicating every day I can control myself better for you.

 

Helping Ms Lee in the shower

After telling me that my freshly shaved look was much better I didn’t hear from Ms Lee for a few days. I was extremely desperate to be allowed to relieve the intense pressure in my balls and was anxious to hear from Ms Lee, hoping she would give me permission to do so. I didn’t even care that I would have to use my new milking chains and would derive no enjoyment from the milking.

But no word came from Ms Lee. I didn’t know if she was teasing me or was just not concerned about my plight. This silence on her part reinforced the lesson I had learned so long ago – my pleasure was not a priority, my only concern was to see to Ms Lee’s pleasure.  I was reflecting on this lesson one morning in the shower and sent Ms Lee this message regarding my thoughts:

As I was showering this morning I was thinking about my recent message to you about helping you in the shower. I must confess that my unrestrained penis took the opportunity to enjoy an unfettered erection as I thought about washing and scrubbing your lovely, naked body. After my shower and my Worship it was quite a struggle to get my deprived penis into my chastity sleeve. I was so aroused from thinking about your naked body that my penis strained like crazy with every additional chastity chain I attached.

Once my sleeve was secured by the chains I was ready for another day in extended chastity for your pleasure. My penis strained in useless frustration as I pondered that I had no idea how far you would extend my new chastity record before it pleased you to allow me to be milked. I then slipped into my black lace panties as per my daily schedule and thought about what you would be doing at this time of day.

I thought of being at your service after I had helped you in the shower. As you were relaxing in your bedroom, drying off and such, I would go to the kitchen to prepare your breakfast. I would have purchased fresh fruit and things for you, knowing your preferences. I would prepare your breakfast to your standards and liking, adding some extra touches that I hoped would please you. Once everything was perfect I would bring your food to you on a polished tray so I could serve you breakfast in bed.

Once I had you settled back in bed with your breakfast tray in place my service would continue. As you ate and enjoyed the fruits of my labor I would labor to further please you. I would start by massaging your feet and legs, helping you to relax. As you continued to enjoy your breakfast I would slip into the bed between your legs and slide forward so I could begin to please your pussy. I would be careful no to get you too excited so you could continue to eat in leisure.

Only after you finished eating your meal would I pick up the pace and begin my worship in earnest. Being well practiced in pleasing you, I would quickly have you excited and bucking on my face. I would concentrate on your pleasure, knowing that not doing so would result in the opposite for me since one of the items I brought on the tray was your favorite flogger. After a while, as you got more excited, you would begin to squirt. Being quite thirsty I would be anxious to capture every drop, being careful that nothing stained your bed. Of course I would be doing the laundry later in the day anyway, but I wouldn’t want you to have to endure any wet spots.

After you settled down a bit I would massage you a while to help you relax again. Then I would take away the tray and empty plates, returnng to the kitchen to continue my chores.

In chastity for your pleasure

Milking Chains

Ms Lee’s response to my first begging message  was short and direct:

Fashion those new chains, but do not use them without my permission.  Let me know when you’re done.

I fashioned my milking chains by making a set that was two links shorter than my already tight chastity chains. I could barely fasten them around my penis when it was flacid. It was obvious that they would prevent erections of any sort at all. I then informed Ms Lee that I had completed my chains and received this reply:

I want to see a picture with them on.  Put them on, take a picture and send it to me, then remove them.

It was incredibly difficult to do as Ms Lee asked. I realized she would want to see how well the chains restricted my penis so I put them on without the protection of my chastity sleeve underneath. My penis rebelled after the first chain was attached, swelling in an attempt at an actual erection. The intense pain of the chain digging in caused my penis to shrink a bit, allowing me to attach the 2nd chain. I countinued in this maaner until all the milking chains were in place, then took the photos Ms Lee wanted. When I sent her the photos I received this reply:

I see you also have to trim again.  Use these new chains when I give you permission to do so.

Ms Lee expected me to always keep the fur around my penis trimmed and shaved to her specifications. Using my razor I quickly complied and sent her new photos.

I was relieved when I received her reply:

Much better!

 

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

Waking Ms Lee

As my time in chastity grew longer, my obsession with Ms Lee’s rear grew stronger. Every time I felt my deprived penis strain against my sleeve I would find myself thinking about rimming her.  One morning when my frustration was particularly strong I sent her this message:

It is early in the morning here and I am thinking about you sleeping soundly in your bed. As I watch you resting peacefully I can feel my penis stirring within my chastity sleeve. I have been in chastity for your pleasure for 40 days now and my penis attempts to harden in reaction to the slightest stimuli. Of course my sleeve firmly prevents me from enjoying such a pleasure so I am focused on your pleasure as things should be.

As I feel my frustration build I can’t stop myself from crawling into the bed with you and sliding beneath the covers. I would like to hug you, but in my desperate state I feel it would be more appropriate to worship your luscious rear instead. I lightly start to kiss your derriere and gradually move in closer. I let my tongue slip slightly inside your anus as I reach beneath you to feel your perfect pussy. I press my tongue in deeper and gently rub you with my hands. As I feel you begin to waken I press my tongue in more firmly and feel you push back against me.

As you move against me I become more excited and my penis strains even harder against my sleeve. I press my tongue in deeper and pick up the pace a bit with my hands. I lightly slide a finger inside you, but my tongue is even deeper inside your rear. I pull you into me as I begin rimming you in earnest.

Now you begin to stir and push against me even harder as I feel you begin to shake and moan. I pick up the pace even more as I feel your first orgasm build. I continue to rim you with my tongue as my finders push deeper inside your pussy, spreading your lips and massaging your clit. Even though my tongue begins to tire I don’t stop. Instead I rim you even harder and deeper as I feel another orgasm overtake you. My hands are getting wet as I feel you squirt. I would love to lick that up but my tongue remains firmly in your rear where it belongs. You are insatiable and my worship goes on and on until my tongue can continue no more.

I collapse in exhaustion as you stretch out in enjoyment from the multiple orgasms you just experienced. As I feel my penis continue to strain against my sleeve you tell me that I have been a good boy and that I have just earned myself the honor of being alllowed another day in chastity for your pleasure.

I hope you smile as you read this, thinking about me frustrated and pantied.

In chastity for your pleasure

A new obsession

As the length of my chastity increased, so did my desperation and I found myself focusing more and more on Ms Lee. I was in awe of her control over me and felt a strong desire to worship her for taking control of my sexuality.

During my morning Worship sessions I was also becoming very anally focused. I was ramming my anal plug harder and harder in a desperate attempt to derive some sexual stimulation. As my anal focus increased I also found myself beginning to think about Worshiping Ms Lee in this manner. I then sent her this message explaining my desire:

This morning during Worship, as I rubbed my rear against my bowl in a mad attempt to ram my anal plug in deeper I  begun to think about worshiping you in a different manner. I remembered chatting about my rimming you and the idea has been on my mind a lot lately. I would love to get on my knees right now and give you a long, leisurely, sensuous rimming. Or perhaps you would enjoy it more if you were lying on a bed while I worshiped at your rear. While I rimmed you I would use my fingers on your pussy, doing my best to excite you. I wouldn’t stop until you were cumming and I wouldn’t stop then, I would continue until you were shaking and leaking. And of course I would be in chastity while doing so which would drive me to provide you with even better service.

I hope you have a wonderful day today.

In chastity for your pleasure