Archive for the ‘Masturbation’ Category

My Monthly Release

August 25, 2016

As I mentioned in my previous post, Ms Lee has been kind enough to allow me to release once per month at a time of my choosing. She granted me this generous gift because I have been under so much stress lately and she thought a monthly release would help. I continually remind myself that I must be very thankful to Ms Lee and not assume this will continue forever. Ms Lee seems to enjoy keeping me in chastity for multiple months at a time so I will treasure these monthly releases for as long as it suits Ms Lee’s whim to allow them.

She did however stipulate one condition with my most recent release. She told me to film my masturbation session and post it here on my blog. I find this exceedingly embarrassing and humiliating but I suspect that just pleases Ms Lee all the more. So I must thank Ms Lee for providing me this opportunity to please (or at least amuse) her. Here is the video of my release:


Another break

August 4, 2016

It has been over three months since my last posting and I must apologize to Ms Lee and my readers for neglecting this blog. As will occasionally happen in my overly busy life I was unable to keep up with all the demands that were put upon me and had to work myself ragged just to make sure nothing critical fell apart. It finally looks like I am getting a handle on everything but you never know what might happen next.

I have to thank Ms Lee with all my heart for being so understanding during this period (as well as previous ones). She has generously allowed me time to deal with my issues and gave me a chance to catch up with everything. I don’t know how I could have managed without her support. However I feel guilty for not keeping up with my blog as well as other expectations I should have been more responsible about. All I can do is try harder to meet my responsibilities and hope that Ms Lee will forgive me.

Back in June Ms Lee also generously told me that I would be allowed to masturbate freely once a month on a day of my choosing. She also has not required me to wear my chastity sleeve on a daily basis. This has really helped to reduce my stress levels but I am well aware that I cannot expect this excessive level of freedom to continue forever.

A couple of weeks ago I decided to take advantage of Ms Lee’s generous offer for the month of July. I had held out as long as I could and I was incredibly horny and frustrated by then. I had begun to frequently find myself thinking about my purple babydoll nightie that I keep in the back of my closet. When I purchased it Ms Lee told me that I should wear it every time I was allowed a release. I told Ms Lee I wanted to wear my babydoll nightie when I released and I also asked her if I could plug myself with my anal plug. I wanted to try to stretch out my enjoyment and try to avoid coming in less than a minutes as I all too frequently do. Ms Lee was generous once again and gave me permission to do so.

Once I was properly plugged and dressed in my babydoll nightie I began stroking my penis. I was rock hard in no time and worried that I might release all too soon as usual. So I slowed down and tried to control myself. Before long I found myself thinking about serving Ms Lee as her formal butler. I long ago ceased having normal male masturbation fantasies. Mine now revolve around my pretty lingerie and serving Ms Lee. For some reason the idea of serving Ms Lee as a formal English butler gives me an incredible submissive rush. I used to fantasize about serving Ms Lee as a sissy french maid but she made it clear that she preferred to be served by an English butler. She does not cater to my pigmale fantasies and I have dedicated myself to learning how to be the best possible English butler so that I can properly please and serve Ms Lee.

But I digress. As I thought about serving as an English Butler I stopped stroking myself and began moving my plug in and out of my greedy rear. I would pull it almost all of the way out and then ram it all the way in. I continued in this fashion until I could no longer keep my hands off Ms Lee’s property. I began stroking myself again but stopped every time I came too close to releasing. I actually managed to stretch out my play time to a full 15 minutes, far longer than I have managed in years. I’m not quite sure what to make of that, but it was quite enjoyable.

I released quite a large load which I then dutifully licked up. I then put everything away, thankful that Ms Lee is so understanding and generous. Sometimes I forget how fortunate I am to be Ms Lee’s property.


Double Release

June 20, 2015

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.

The Generosity of Ms Lee

June 5, 2015

When I went to sleep Tuesday night I set two alarms to make sure I would wake up in time since Ms Lee generously had given me permission to touch myself and cum between 6 and 6:30 Wednesday morning. I was horrified when I woke up that morning at 7:30, having slept thru both alarms. I desperately wanted to masturbate, but I dared not touch myself since I missed the time-frame Ms Lee had specified. I told her about my failure and expected her to tell me that I had squandered my opportunity for the week.

I was ecstatic when she told me that she would give me another chance at 6PM that evening. Although Ms Lee is extremely strict with me she also is very caring and surprises me with her generosity.

At 6PM promptly I began enjoying Ms Lee’s gift and began touching myself in a sexual manner for the first time in over a week. It was heavenly to once again enjoy a full erection and stroke it with abandon. I took it slow at first as I wanted to be able to enjoy the full half hour that Ms Lee had allowed me. My hair trigger penis almost betrayed me as within minutes I could feel myself almost explode in release. I quickly let go of my penis and waited until I calmed down before touching myself again. Before beginning again I thanked Ms Lee once more for her generosity, I am so fortunate to be her property.

I also took the opportunity of being hard to measure my penis to check on whether I had fully regained the length I had lost due to my previous cycles of extremely extended chastity, restrained by my viciously tight chastity sleeve. I was shocked when I discovered that I measured somewhat less than five and a half inches, more than half an inch less than I was prior to becoming the Property of Ms Lee. I informed Ms Lee of this and her response indicated that she did not consider my loss a big deal. Perhaps she is correct since I never have the opportunity to use my penis like a real man anyway. I just hope that it pleases Ms Lee that her property has been reduced in size due to the extended chastity it has previously been subjected to for her pleasure.

I spent more time hands off trying to control myself then I spent masturbating, but I did manage to take advantage of the full half hour before releasing. As the final moments approached I began stroking like mad and quickly felt my release approaching. As Ms Lee expected, I squeezed the tip of my penis as well as my scrotum as my cum attempted to explode out of my penis. I successfully managed to prevent the explosion and could feel it backing up behind where I squeezed. Once my orgasmic spasms ended I released the tip of my penis and saw my cum slowly dribble out. I was amazed at how much kept dribbling out and I dutifully licked it all up as Ms Lee expected. I then thanked Ms Lee again for her generosity.

It has now been two days since my ruined release and I intend to wait until a full week passes before I dare to beg Ms Lee once more for permission to touch myself. I am hopeful that by then I will be in the proper state of mind to beg sincerely.

Being allowed to touch myself reminded me of the intense joy & pleasure that I am denied and having a ruined rather than an orgasmic release insured that my frustration and desperation continued unchecked. I suspect Ms Lee intended things this way and I only hope she enjoys having her property obedient and untouched.

Ms Lee Takes Her Property Back

June 1, 2015

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.

A rare and generous treat

January 23, 2013

After my recent accidental (and pleasureless) release I was certain that it would please Ms Lee to see me endure another 100 days or more of chastity before she allowed me another release. Instead I was pleasantly surprised when she informed me less than a week later that I was to be allowed another release. Even more surprising was that she was going to allow me to enjoy a very rare pleasurable release! This was an extremely generous gift and I am quite aware that it may be a long, long time before I am allowed such a treat again.

Ms Lee had taken note that in my last blog entry that I mentioned I am unable to masturbate for more than a minute or two anymore. When I used to release almost every day I was able to enjoy masturbation for long periods of time. But due to the extended chastity periods I now endure as Ms Lee’s property I am no longer able to do so. On those rare occasions when I am allowed to masturbate the pent-up pressure in my balls makes me so frantic that I lose control almost immediately. This is quite frustrating and I can only hope that it pleases Ms Lee to have ruined my ability to derive any real enjoyment from masturbation.

Ms Lee informed me that two minutes was thus going to be the limit for how long I would be allowed to masturbate. She told me to set a timer and have at it until the timer went off. I have to admit that it was intimidating to be faced with such a strict limit on how long I would be allowed to enjoy myself, particularly since it had been just about 120 days since I had enjoyed my last pleasurable release. As I pondered this it occurred to me that Ms Lee was rewarding me with exactly one second of pleasure for each entire day of chastity that I had endured for her.

To make things even more frustrating (if that was possible!) it took me a while to even get hard once I had started the timer. I was probably too focused on my time limit and frustration to allow myself to truly enjoy masturbating and I saw that thirty seconds had passed before I was able to achieve a full erection. As I continued to stroke my desperate penis I finally began to feel the true pleasure of masturbation and realized just how badly I missed being allowed to jack off at will. The realization that Ms Lee had taken such complete ownership of my sexual pleasure instilled such a perverse, intense excitement that I lost control and began to feel my balls clench and pulse in preparation to release. I desperately wanted to slow down so I could enjoy the full amount of time I was allowed but as I passed the minute and a quarter mark I released a messy load that I then licked up as I knew Ms Lee would expect.

I promptly thanked Ms Lee for allowing me such a generous gift and immediately returned to faithful chastity for her pleasure. I can only hope that she does not reduce my time limit accordingly for my next release now that I have once again demonstrated my pitiful lack of control.

Edging and frustration

September 26, 2012

About a week after I reported to Ms Lee that my penis had shrunk by over an inch she told me to fix my situation. To do this she instructed me to begin edging as much as possible, but under no circumstances was I allowed to release. Edging without releasing would be difficult under any conditions, but Ms Lee expected me to control myself even though it had been over five months since my last pleasurable release! Once again Ms Lee was demonstrating to me how deeply she cared for my well being, but I realized that her cure was going to subject me to some exquisite torture.

As I indulged in my first edging I discovered that the torture was going to be even worse than I had imagined. My badly beaten penis was still so raw and sore from the months of tightened chastity that it was actually painful to masturbate! I was so frustrated that I endured the pain and continued to wank like a crazed school boy but all too soon I could sense that I was about to lose control. I was only able to last about a minute the first time before I had to stop. I desperately waited for my twitching penis to calm down enough to try again, but the second time I was only able to last about a half minute. I tried a few more times, but I rapidly reached the point where I could barely touch my throbbing penis without losing control.

Somehow I managed to continue in this manner for an entire frustrating week without losing control. I also discovered another disturbing side effect of my long term chastity. Whenever I stopped touching my penis while edging my erections only lasted a short time before I became flaccid. I seemed to have lost my ability to maintain erections for any significant length of time. When I reported this new discovery to Ms Lee she told me she thought it might be temporary, but once again seemed to think my situation was of no great concern as she said we would just see what happens.

As I continued to edge I started using used my anal dildo at the same time. I was quite embarrassed to discover that I was able to obtain much more pleasure from my dildo than I experienced by edging. Whenever I masturbated until edging I had to stop all too soon or risk losing control. Rather than enjoying the freedom to masturbate, it was turning out to be an almost unbearable frustration. But I never had to stop when I was pleasing my greedy rear with my huge anal dildo, I could just go on and on. I was beginning to become jealous of women because they can cum repeatedly, but then I realized that Ms Lee was training me how to do the same thing (at the expense of having a functional penis).

Ms Lee then upped the ante and told me to rub my penis with lubricant the next time I edged. I couldn’t believe how awesome it felt to wank my slicked up penis. Unfortunately I nearly lost control immediately as my hair trigger penis began twitching like mad. I was beginning to dread edging, but Ms Lee seemed determined to see my penis regain some of its lost length.

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.

Begging to be plugged

April 1, 2012

During the past six months Ms Lee has granted me three pleasurable orgasms, the last one being about six weeks ago. During this dry spell I have learned to appreciate the teasing pleasure that anal stimulation provides me with. Ms Lee is very generous in allowing me to use my anal dildo every morning so i can milk myself when the pressure becomes too great. Rubbing the dildo against my prostate is nowhere near as pleasurable as masturbating my penis, but I have given up expecting that experience. I know now that Ms Lee only allows it on rare occasions, usually on a whim, just to remind me what it is that I am missing. Of course this reminder of her control over me binds me ever more closely to her will.

While I enjoy my morning sessions with my anal dildo, I find myself yearning for some sort of sexual stimulation during the day. As my current chastity period extends well into the second month my focus centers on my rear, clenching against nothing in a pathetic attempt to excite myself. I realize that I am missing the sensation of my anal plug pressing against my prostate.

It has been a month now since Ms Lee allowed me to be unplugged, after enduring two straight months of being plugged on a daily basis. Being plugged every day was quite difficult and uncomfortable, but I have to admit that at times I greatly enjoyed the sensation of the plug pressing on my prostate. I would certainly not want to return to being plugged daily on a continuous basis, but it would be quite pleasurable to feel my plug fill my greedy rear for a single day or so.

With that thought in mind am on my knees, begging Ms Lee to please consider allowing me to use my anal plug for a short time. I would love to wear it for a day or so, but I desperately hope I would not have to begin another lengthy period of being plugged daily.

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