Archive for the ‘Butt Plug’ Category

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.


Plugged again

July 27, 2015

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:

Plugged, chastised & pantied

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.

Feeling like a sissy

July 16, 2015

I’m not sure exactly when the change occurred but I’ve realized that my reaction to wearing panties has gradually changed from embarrassment to anticipation and excitement. I’ve always gotten hard and excited in response to the embarrassment I experience when wearing panties but now my excitement is also due to the pure pleasure I obtain from wearing them.

Recently I have had some discussions with Ms Lee because I have been struggling with admitting to myself that I am a sissy. I have been wearing panties and experiencing chastity for years but I had always felt like a man that was just experimenting with submission. Being told to wear panties was part of that submission and although wearing them got me excited and hard it was always due to the embarrassment I endured. But over time the primary reason for my excitement has shifted from embarrassment to the enjoyment I now experience from wearing panties.

I have become quite obsessed with my pretty panties and I have accumulated a large collection including a number of them with garters and frilly skirts. Plain panties are no longer good enough, I now search for frilly and sexy panties, preferably with a lacy garter belt. I think a primary driver of this obsession was due to the sexual starvation I endured when in chastity. I desperately craved any sort of sexual stimulation and I learned to enjoy the feel of my silky panties embracing my chastised genitals. Attached is a photo of one of my favorite pairs of panties, they include a lacy built in skirt and detachable garters.
Red skirted panties

Another obsession I had developed due to Ms Lee’s training involves my extensive collection of anal toys. Ms Lee requires that I conduct a morning Worship session every day that includes having my hungry rear stuffed with my anal plug. I have learned to enjoy the sexual stimulation I experience when my plug presses against my prostate. Just like what happened with wearing panties, I have come to crave my morning Worship sessions and the frustrating excitement I derive from having my anal plug tease my prostate. And just like with my panties, my obsession with my anal plugs makes me feel like a sissy. More information on my morning Worship sessions can be found in this blog entry – How i Worship my Goddess

Ms Lee told me that I should not be ashamed of anything that makes me feel good and she encouraged me to embrace being a sissy if that made me happy. While admitting that I was a sissy felt right to me I was still uneasy because of my preconception that all sissies are gay and that many of them wear diapers and act like little children or babies. While these things may be fine for other sissies they are not part of what I am. Ms Lee helped me to understand that I should not worry about the preconceptions of what is ‘normal’ for a sissy and that I should just enjoy those aspects that make me happy.

I am now putting Ms Lee’s advice into practice as I embrace being a sissy. I truly enjoy wearing panties and playing with my anal dildo and I am no longer distracted with the preconceptions about being a sissy that don’t apply to me. Once again Ms Lee has helped me to better understand my submissive nature. I am truly blessed to be owned by Ms Lee and I am very grateful.

Return to Worship

June 12, 2015

After weeks of faithfully abiding my Ms Lee’s no touching rule I am frustrated and quite desperate. Being unable to satisfy my intense desire for self pleasure I found myself ever more focused on Ms Lee’s pleasure. I began to ask her if there was anything I could do to please her and she responded by telling me to resume my morning worship sessions.

My morning worship sessions seemed designed to optimize the frustration that I endure as the Property of Ms Lee. Before I begin my worship session I must have my anal plug in place. My deprived penis begins to get hard as soon as the plug begins to invade my tight rear and by the time the plug is fully in place my penis is rock hard. I get quite excited due to finally getting to experience some sexual stimulation but it is extremely frustrating since I am still prohibited from touching my penis. The pleasure I derive from rubbing the plug against my prostate is nowhere near as immediate or intense as what I used to enjoy when I was allowed to stroke my penis. Instead I find myself ramming the plug in as deep as possible while I gyrate like mad, desperately trying to amplify my greatly reduced pleasure.

While I engage in my desperate dance of frustration I focus my mind on Ms Lee, concentrating on her pleasure. It is extremely difficult at this stage to resist the urge to touch myself but I remind myself that it pleases Ms Lee to have me obedient and frustrated. I continue to meditate on Ms Lee, thanking her for taking me as Her Property. I find myself almost falling into a trance as my focus moves back and forth between my intense frustration and my gratitude to Ms Lee.

My morning worship sessions are an effective tool for enhancing my devotion to Ms Lee. They also greatly enhance the desperate frustration I endure but hopefully that pleases Ms Lee which is all that matters.

A renewed anal focus

March 9, 2013

As will occasionally happen I have recently been experiencing a few personal issues that have caused a bit of stress in my life. Ms Lee has been very supportive, once again demonstrating her unique approach of caring dominance. Understanding my situation she has allowed me some latitude, but has made it clear that this is not an excuse for me to slack off in my devotion to her. I have continued my duties as her faithful panty washing boy, carefully cleaning the panties that caress her everyday. I also continue to assist her in other ways. I am not sure if it is intended to address my recent stress, but she has also introduced a renewed focus on my anal submission.

During a recent conversation Ms Lee had asked me about my fantasies and I admitted that due to my relentless, extended chastity I have frequently found myself thinking about anal stimulation. Ms Lee’s expectations seem to deviously lead me in this direction. While I am not allowed to touch myself in a sexual manner she does allow one ‘exception’ – I am always free to stimulate my prostate using an anal plug or dildo. The longer I am in chastity, the more desperate I become for any sort of sexual stimulation. But anal stimulation does not provide me anything close to the pleasure and release that I used to derive from wanking like a teenage boy. Instead it leaves me more frustrated than ever, increasing my desperation in an endless cycle. While I do not derive any real complete satisfaction from my anal stimulation I do hope that my desperate attempts please Ms Lee.

One evening after Ms Lee reintroduced the focus on my anal stimulation I inserted my anal plug before I went to bed for the night. I thought I was going to go straight to sleep but I soon became badly distracted by the plug in my rear. I found myself clenching my rear and enjoying the pressure against my prostate. It was quite maddening as I desperately desired a release but the plug did nothing more than tease me. I continued to press against my plug for quite some time before I finally slipped off to sleep, with thoughts drifting in my head of being taken by Ms Lee’s strap on.

I woke a few times during the night and each time I immediately began clenching my rear and pressing against the plug. When I woke in the morning I was so frustrated and excited that I immediately got out my Bigger Tool and proceeded to attempt to milk myself. I was not able to produce anything, but I certainly enjoyed trying. For those who might not be familiar with my Bigger Tool, it is a large, 8 inch long dildo of the sort that a woman would ordinarily use. I had initially began my anal stimulation using one of the slim anal massagers that are popular, but it amused Ms Lee to have me graduate to a ‘bigger tool’. A tool which is much more substantial than my own inadequate member which has been shrunken further as a result of my constant, extended chastity.

Ms Lee now expects me to experiment with different sized and shaped anal toys. I currently have a few standard butt plugs as well as my two anal stimulators. If anyone has any suggestions I would be interested to hear about them.

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.

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.


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.