Begging to be plugged

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

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

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

Giving Thanks

Recently I have been contemplating the fact that once again I am experiencing an extremely long chastity period for the pleasure of Ms Lee. She sometimes surprises me by allowing a release after a short time in chastity, but it is obvious that she much prefers to see me in extended chastity (over a month).

I am now in my 44th day of chastity for the pleasure of Ms Lee, the second longest period of chastity I have ever experienced. My longest stretch was two months, which ended in a ruined orgasm. I have no idea how much longer it will please Ms Lee to keep me in chastity this time and my frustration increases every time I wonder whether my current chastity period will end with another ruined orgasm.

I just received a message from Ms Lee that she will be very busy the next few days due to the holiday. Of course this means that my current chastity period will be extended as she enjoys her Thanksgiving. Perversely, I could feel my deprived penis straining against my chastity sleeve in frustration as I contemplated continuing my chastity in faithful devotion to Ms Lee.

As I performed my daily Worship session this morning these thoughts took my frustration to new heights. I prepared myself as always, restraining my penis with my cock ring and inserting my huge Worship plug in my greedy rear. Extended chastity combined with Ms Lee’s no touching rule has instilled an intense anal fetish in me since the closest I normally come to experiencing sexual pleasure is when I am plugged and Worshiping Ms Lee.

This morning my desperation and excitement combined to make me delirious as I ground the plug into my rear. That plug is so huge that it presses firmly against my prostate, which in turn causes my penis to strain against my ring. As my Worship session continued I was gyrating like mad, working to increase the sexual stimulation the plug provided.

I could feel my sexual pleasure slowly increase as I continued to grind my prostrate with my plug. I almost reached the point where I thought I might be at risk of an unauthorized release. However, I didn’t quite reach that point and continued my frustrated grinding until my Worship session was completed.

As I panted in exhaustion, I reflected that I am extremely fortunate to be owned by Ms Lee. I love being her boy and ended my Worship session by giving thanks to her for continuing to keep me on.

Another pair of new panties

A little while after I was ‘unplugged’ I returned to NYC on business and had an opportunity to go shopping for panties again. I sent Ms Lee this message regarding my shopping trip:

Yesterday I purchased my newest set of panties. I looked for a set with a skirt & garters as you expected. I had a bit of trouble finding a set similar to the red ones you like and was embarrassed to have to ask for help again. Finally one friendly sales lady suggested the skirt like panties I am wearing in the attached photos, but I was concerned because they had no crotch to them. We had to look around to find a matching thong from the same set. The photo titled WhiteBlkTrimThong shows me wearing just the thong, before adding the skirt/panties with garters.

I really hope you like these new panties, they tease me even more than the red ones! They are quite elaborate, with the seperate thong, double layered skirt and garters.

Unfortunately, I had neglegted to keep myself properly groomed in my pubic region, which Ms Lee observed when viewing the photos I sent to her. She then responded:

Does not look at all appealing with all that fur.  take care of it.

Of course I immediately did as she expected, trimming and shaving myself to a more acceptable presentation. I then sent her new photos of myself:

Attached are some photos I took this morning, after shaving and trimming my fur. I hope that my appearance is more pleasing now. I have to admit that shaving & trimming myself for you got me quite excited. I was actually in pain because my penis was straining so hard against my chastity sleeve..

Perversely, the pain just made me more excited, adding to my frustration. I haven’t quite reached three weeks in chastity, but my desperation is already extremely intense. Once again you have my hormones on a wild roller coaster ride. Please understand that I would never complain about my frustration, I am just hoping that it provides you some pleasure or amusement.

 

Unplugged

After 3 long weeks of wearing my anal plug all day long I reached the end of the month and was allowed to go unplugged. It was extremely difficult to wear the plug all day long, but I knew it pleased Ms Lee, so I endured.

I am always anxious to find ways to please Ms Lee. It seems that constantly being in extended chastity has instilled in me a very deep seated need to please her. On the surface, this would seem to be because I depend on her to determine when I am allowed sexual pleasure. But as I think about it, I realize that Ms Lee’s pleasure has become my own vicariously.  Pleasing her provides me with a strong sense of satisfaction and contentment.

Shortly after my ‘unplugging’, I sent Ms Lee this message regarding my experience:

Today is my second day without wearing my plug. I have to admit that I do miss it, although it is an incredible relief to no longer have to wear it all day long. At times it was quite exciting and enjoyable, and at those times I couldn’t get enough of grinding and rubbing on the plug. I would get so sexually excited and my penis would strain like crazy against my chastity sleeve. It was such an incredibly frustrating tease to be able to sexually excite myself, but be denied the pleasure of a release. I would just keep grinding and gyrating like crazy, thinking all the time of the awesome control you have over me and my sexuality. I absolutely thrill to be in submission to you and I thank you for having me. I do hope that my recent essay was pleasing to you and that you will consider keeping me on. I am now back on my knees, begging you to allow me to continue to be your faithful boy.

As exciting and sexually pleasing as wearing the plug was, it was also extremely uncomfortable at times and frankly quite inconvenient. Some times no matter how much extra lube I might use I could still feel a burning sensation that was very hard to endure. I also had to struggle at times with trying to walk and sit normally while stretched by the plug. In fact I am now back on my knees begging you to only have me plugged infrequently because it was such an effort and struggle. However, no matter how painful or difficult it was at times I was determined to complete the month for you, plugged, chastised and pantied because I wanted to please you and demonstrate my obedience and devotion.

I am also concerned that the constant plug wearing may have permanently stretched my rear. I do know that it steadily became easier to slide it in and I felt less and less stretched as time went by. I was thankful to hear that you didn’t think my penis would shrink from daily chastity, but I am certain that I have been stretched by the plug.

I also began to truly crave the sexual pleasure the plug was providing me. I get quite desperate for sexual stimulation when I am in extended chastity for you and I found that I could always excite myself by grinding on the plug. It was almost like I was allowed to masturbate again, but with no possibility of a release. Naturally this combination was incredibly frustrating, but I do think I was becoming addicted to the pleasure of the plug. I know I miss it right now. I can feel my penis straining against my sleeve and my rear feels empty as I gyrate uselessly in frustration. Are you trying to transfer my center of sexual focus from my penis to my prostate? If so, I think you may be succeeding!

I am also teased by the silky smoothness of the pink panties I recently purchased at Macys. The panties tease me just as the plug did, but they do not provide me the sort of sexual pleasure that rubbing against my prostate did. By the way, I am going back to NY next Wednesday and I’ll have a chance to go shopping at Macy’s again. Do you have any particular color or style of panties that you would like me to shop for?

Chastised & pantied for your pleasure,
In my 32nd day of chastity,
and 50 days since my last pleasurable release

Begging

During a recent chat with Ms Lee I was talking about my need to please her, telling her that ‘in my chastised state I live for your pleasure‘.  As I explained my need she responded:

you love being submissive for me, don’t you boy?

Of course I responded that I did, but she was not satisfied. Ms Lee told me to beg to be hers, that I hadn’t done so recently. I proceeded to beg, but she was still not satisfied. She then gave me a new assignment:

here’s what you’re going to do: you’re going to write me a five page essay, double spaced begging me properly to be mine. provide the whys. think hard and deep as to why i should keep you. focus on me, not you, and everything you know about me

It took me a while to properly compose my essay. At one point I told Ms Lee that I felt like a naughty school boy that had been punished and must write something like ‘I will focus only on Ms Lee’s pleasure’ 500 times.  I had to think long and hard, thinking about it from Ms Lee’s perspective, explaining why she should bother to keep me on as her property. I also had to keep the proper attitude in my essay, begging frequently and sincerely.

I found composing the essay to be a very enlightening exercise, making me realize just how fortunate I am to be Ms Lee’s property. She has enabled me to realize my proper role in life, to be in submissive service to a dominant woman.

Although it may sometimes amuse her to tease and play with me, I now understand that the most important thing for me is to demonstrate to Ms Lee every day that my focus is on her. There are many submissive boys who would feel fortunate to be owned by Ms Lee and I must show her through unstinting devotion to her pleasure and well being that I stand out above the others.

A frustrating chat

About a week after I began wearing my anal plug on a daily basis I had an opportunity to have an exciting text chat with Ms Lee as she pleasured herself. The next morning I sent her this message reflecting on our chat:

Thank you so much for chatting with me last night. I know it is not easy on the phone. I hope that I helped you enjoy yourself and that you went to sleep with a smile on your face, thinking about my devotion.

I can’t begin to tell you just how frustrated I was after our chat. I thought I was going to lose my mind as I pictured you using your vibe as I described how I would love to rim you. And the fact that I was plugged and pantied for you at the same time just made my frustration that much more intense. When you told me you were coming I could feel my penis pulsing in desperation against my unyielding chastity sleeve.

The fact that I knew my own pleasure was to be ignored helped me to focus on yours. I worked very hard to please you by describing how I would rim you and use my fingers to excite you. I am becoming quite addicted to being devoted to your pleasure!

Attached are some photos I just took for you, showing me plugged, chastised and wearing the red panties with garters and skirt that I recently purchased. These panties tease me worse than any others! I don’t know I I am going to be able to endure all the teasing and frustration I am going to be subjected to today. Needless to say, you will always be on my mind.

Plugged, chastised & pantied for your pleasure,
In my 16th day of chastity,
and 34 days since my last pleasurable release

Being plugged

The morning after Ms Lee had me begin wearing my plug on a daily basis I sent her this report:

Attached are some photos I just took for you, showing myself plugged, chastised & pantied. I still can’t believe that you expect me to do this every day for the rest of the month! It was so difficult to endure wearing the plug yesterday. I think it will take a while before I get used to wearing it all day, but it is so exciting to be reminded of your will and dominance over me with every step I take (and every time I sit down!).

It is also incredibly frustrating to have the plug in me while I am chastised & pantied. The plug excites my prostate which makes my chastised penis attempt to get erect. My deprived penis is already being teased so badly by my panties and perversely the pain of straining against my chastity chains just gets me even more frustrated and excited. Between the panties, the plug and the chastity sleeve I am going absolutely crazy with desperation!

Plugged, chastised & pantied for your pleasure,
In my 14th day of chastity,
and 32 days since my last pleasurable release

The next few days were quite an ordeal as I adjusted to being plugged all day long, every day. I had previously worn my anal plug for an entire day, but the realization that Ms Lee expected me to wear it full time for nearly three weeks made me weak in the knees.

Plugged, chastised & pantied

On my next trip to NYC I stayed overnight at a hotel while attending an industry conference in Times Square. After I finished my first day at the conference I returned to Macy’s to shop for another pair of panties as Ms Lee expected. She had told me to look for a pair in purple, which was quite a challenge. I am slightly color blind, so I asked two different sales ladies to confirm that I was buying the proper color panties – in my size, of course!

Later that night I called Ms Lee from my hotel room to tell her about the panties I had purchased. Of course I was wearing my new panties when I called, as well as my ever present chastity sleeve. I had been in chastity for about 10 days at this point, but Ms Lee did not seem interested in releiveing me of my frustration. Instead she asked if I had brought my butt plug with me.

Luckily I had, and I quickly inserted it at Ms Lee’s command. She then proceeded to badly tease me, telling me to push it in deeply, then pull it out and then push it back in again. She continued tormenting me in this manner for a while and I could feel my penis straining against my sleeve as the plug stimulated my prostate. When Ms Lee said good night to me she made it clear that I was to spend the night with the plug remaining in my rear.

The next morning before I left my room I received a text message from Ms Lee. She asked if I was still in my room and then told me she wanted me to keep wearing my anal plug. She then told me that she wanted me to remain plugged, chastised and pantied for the rest of the month, which was nearly three weeks away!

Another pair of new panties

The marks on my rear were still quite visible the next time I went to New York City and went shopping at Macy’s for another pair of panties, as Ms Lee expected. Once again I endured an extremely embarrasing situation which I duly reported:

Attached are some photos I just took, wearing my new pink panties from Macy’s. Once again I was extremely nervous as I asked one of the helpful sales ladies to help me pick out a pair of pink, feminine panties in my size. I think my face was as pink as the panties I eventually purchased.

And once again I noticed a smile or a smirk as the sales lady sized me up and helped me look through a selection in pink. Once in a while she would hold up a pair and ask me with a sly smile if they were feminine enough for me. Thankfully she did not hold them up to me as she asked!

When she showed me the pair I am now wearing I could feel my heart begin to race. I could also feel my deprived penis strain against my sleeve as I examined the triangular shaped panel in the rear with the oval cutout. I assured the sales lady that this pair was certainly feminine enough for me.

I can feel my penis straining again right now within these pink panties. I am SO desperate at this point that I am afraid it will be straining all day. And it is so frustrating to be wearing such feminine panties! Every time I feel my penis strain I imagine your hand holding and restraining my penis, touching it as I am not allowed to.

In my 7th day of chastity for your pleasure,
and 25 days since my last pleasurable release

Marking myself for Ms Lee

Shortly after my shopping trip to Macy’s I was chatting with Ms Lee and I told that I would soon be shipping a riding crop she was interested in to her. I had previously told her that I would be sending it to her, but I hadn’t had a chance to pack it up yet. I knew I would probably be in trouble for my delay so I asked:

May I get on my knees now and beg you to allow me to mark myself with it before I ship it to you?

Not surprisingly she responded:

Oh, yes. mark yourself well, too, for making me wait, my love.  send me photos of your marks  i want them very visible

I had previously marked myself with a belt and sent her photographs when I deserved punishment and I had found it quite difficult to strike myself hard enough to make the marks visible, I responded:

omg! I had to strike myself so hard with the belt last time just to get very slight marks to show. I can’t imagine how much it will hurt to mark myself well enough to satisfy you and make them very visible

Ms Lee did not seem to mind my concern as she replied:

I’ve come to terms lately with the fact that i’m a sadist.  🙂  * sly smile *

I experienced quite a bit of self inflicted pain as I marked myself enough to show very visible marks. I then quickly packed up the crop and shipped it ti Ms Lee before I earned myself another punishment.