Archive for the ‘Teased’ Category

Requesting feedback regarding my panties

June 20, 2015

Anyone who browses through this blog will learn that Ms Lee enjoys having me wear panties instead of male underwear. As she expects, I now wear nothing but panties, 24×7. Male underwear is strictly prohibited. During my years as her property I have built up an extensive collection of silky & lacy panties, probably more than most women.

Keeping me in panties provides Ms Lee with a number of benefits. For starters, it still embarrasses me to no end, which greatly amuses Ms Lee. I have learned the hard way that it pleases her immensely to see me embarrassed in a number of ways and panty wearing is one of her favorites. Wearing panties also puts me in an intensely submissive state of mind, making me putty in her hands. Being kept in panties also provides her with the opportunity to embarrass me further as she requires that absolutely no pubic hair be visible. This is particularly challenging as some of my panties are quite skimpy. I spend a considerable amount of time & effort shaving the area around my panties as I desperately want to please Ms Lee and I fear the punishments she will administer if I fail to keep myself properly presentable.

Probably one of the most significant benefits Ms Lee enjoys by having me in panties is the merciless teasing that my deprived penis suffers as a result. After weeks of abiding by Ms Lee’s no touching rule I am desperate for any sort of sexual stimulation and the sensation of my penis straining under my silky panties drives me mad. The inhuman frustration I endure as a result of this teasing drives me even further into submission but I suspect Ms Lee just plain enjoys knowing that I am hopelessly frustrated and desperate.

Those who are interested in reading more about my panty wearing are encouraged to check out the dozens of postings under the Panty and Panty Washing categories. But at this time I would like to request, no – make that beg, for feedback regarding how I look wearing the panties in the photo below (these are the panties I am wearing today). Please provide any feedback at all, positive, negative or indifferent. I would also be interested in any suggestions on how I could better please Ms Lee with my panty wearing.
My purple panties

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.

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.

Begging to be plugged

November 27, 2011

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.


November 21, 2011

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

Being plugged

November 18, 2011

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

November 12, 2011

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!

Unfettered masturbation

October 21, 2011

After teasing me about being unable to release my chastity chains so I could masturbate, Ms Lee surprised me again:

go have an unfettered erection, an unfettered masturbation, and an unfettered production. Feel free to produce all week, in any way you so choose,  as often as you wish

 me: Really?
yes, really  🙂 it’s my reward to you for staying loyal
I was ecstatic upon hearing this and a few days later I sent Ms Lee this update:
I’ve also been thoroughly enjoying the freedom you granted me to play with myself as I wish for the remainder of the week. I have to admit that I have been wanking like a little school boy as often as possible. I had quite forgotten just how enjoyable it is to stroke my unfettered penis and experience unrestricted erections. I am on my knees right now thanking you for your generosity.

I also have a few other things I think I should admit to. The first is that I have discovered that it is almost a necessity for me to wear panties now in order to get fully sexually excited. In the last few days whenever I’ve tried to play with myself in the nude (like when taking a shower) I’ve found that it takes a while to really get hard and excited. I realized that I was craving the feeling of panties and as soon as I put them on I got rock hard and randy! I know that you are not fond of your boys dressing in women’s clothes, but you have instilled an incredibnly strong panty fetish in me. I have become quite adicted to wearing them and I beleive the reason is that when in chastity and not allowed to touch myself they provide me my only available sexual stimulation. When I am chastised and pantied I get aching hard ons due to the teasing inflicted by my panties, especially when walking and feeling them tug on my restrained penis.

One other admission is that every time I masturbate now I picture myself rimming and worshiping your awesome rear. The thought of rimming you to orgasm while I am chastised and denied drives me crazy! I get so excited that I have a hard time stopping myself from releasing. I also get excited when I think about you taking me with your strap-on, or having me milk myself with my anal plug. As soon as I think about anything else I start to loose my erection. Then as soon as I think about rimming you I get hard all over again. Are you training me to have an anal fixation?

And as I mentioned before, I am holding back on releasing becuase I am afraid that I will loose the sexual high that you have me on. I am so desperate and frustrated that it might take days after my release before I’m back to the point where I would enjoy playing with myself again. By then this week would be over and I would have squandered the opportunity you granted me.

Of course this means that my chastity (though unfettered) continues for now, with no pleasurable release just yet. I can’t beleive that I am stoping myself from releasing right away, but I have no idea when you might grant me an opportunity like this again. I need to savor and enjoy this freedom to touch myself as much as possible while I can. It has been nearly three months since my last pleasurable release and I know I’d better enjoy this while I can, since it might be a while before you allow me to do so again. Of course this means that my teasing and torment continues unabated. Even though I can now touch, I find myself in a position where I am still unable to truly let loose and just release at will. Your control over me is intense and deeply affects how I can react to the opportunity you granted me.

I apologize if I am rambling, but my mind and emotions are in turmoil right now. Once again you have knocked me completly off balance and I am scrambling to keep up. For instance – I have no idea if it is part of your plan, but I am beginning to realize that once you have me back in extended chastity I will be badly teased by the memory of how much I’ve enjoyed playing with myself, I had truly started to forget what I was missing and now you have reminded me.

In my 7th day of chastity for your pleasure, and now 83 days since my last pleasurable release

A chat & a tease

October 17, 2011

A few days after my second ruined orgasm I was fortunate enough to join Ms Lee for another chat. Below is a portion of that chat, with Ms Lee’s comments in italics:

btw, i have [one of my other boys] produce for me as often as possible every day

omg!  I assume he is allowed pleasurable releases?
 yes  too bad he’s not here for me to monitor it
  what i’d want is for him to produce SEVERAL times a day, every day
  after a while, it’ll get harder & harder for him
Ouch! My penis hurts! It is straining against my chastity chains so badly right now
and after a while, when i keep increasing by 1 every day  he’ll want a break
  i think it would be a lovely thing to have a boy in chastity WISH he could have unrestricted production
  and the boy who has unrestricted production WISH he was in chastity
  that would be fun
Well you sure have me where you want me!
i know and i love it
It drives me so crazy that I have no idea when I might ever be allowed an unrestricted production again  I always assumed my chastity cycles would end with one  or more
if you want you can masturbate right now. unrestricted, unfettered. but NO production!
omg!  what a tease!
you’re the one who missing feeling pleasure. so feel away. just no production. 🙂
I can’t get the chains off! My penis is straining so hard I can’t unsnap them!
lol that’s so funny!
it hurts too!
mmmmm…. yummy  it’s a good thing i’m not sadistic…lol
can I at least stroke myself – even being allowed to touch would be nice. please?
  I’m on my kness begging!
i told you, yes. unfettered masturbation. what part didn’t you understand? or would you rather i rescind me offer?
I can;t get unfettered! The chains are too tight! My unruly penis won’t stop straining
so slap it a few times…hard
That just made it hurt more – and got it more excited
oh i was hoping so!  do it again
bullshit. you know you like it
my penis is straining even harder! The chains are SO tight
well keep it up…slapping that is…until i come back
bgin now
ok, i’m back
My penis is being teased so badly!
your little penis loves it and craves it  and you know it
but I miss unfettered so much!
YOU do. IT doesn’t.
 I suppose you may be right
well, look at the slapping thing
  YOU said it hurt and was glad when I came back
  IT told you something else entirely

Another Ruined Orgasm

October 3, 2011

Two weeks after Ms Lee teased me with a ruined orgasm I sent an email explaining my intense level of frustration to her:

One thing I had wanted to discuss with you last night is how incredibly desperate I feel already, even though my current chastity period has only reached two weeks. I find myself constantly straining against my chastity sleeve and always thinking about your control over me. Every morning I have to struggle to get that sleeve on as my deprived penis fights against the chains. Every time my penis strains against the chains it feels like your hands are holding me.

I think my frustration and desperation is peaking so early in this chastity period because I was denied a pleasurable release at the end of my previous period. It is frustrating beyond belief to realize I will soon be approaching three months since my last pleasurable release and I have no idea when I may experience one again. I can feel my penis straining right now as I think about the possibility that my current chastity period may end the same as my last. It will be bad enough if it ends in another ruined orgasm, but if I have to go two months between releases again I can’t imagine how intense my frustration will be.

In my 15th day of chastity for your pleasure

I was even more frustrated when I received her reply:

You’re so funny.  Go ahead and produce.  Make sure it is a ruined orgasm–again.  Then tell me all about it.

I dutifully followed her instructions and then told her about it:

I received your reply early this morning at work, but was too busy with meetings and such to be able to do anything about it at the time. Throughout the day my penis was straining like mad and you were always on my mind. When I got home I then had to deal with family matters and such till late at night. Again my penis strained and again I thought about you and what you wanted me to do.

When I finally was able to find some time alone I thought about the fact that once again I was going to be allowed to release, but denied any pleasure. Once again I was in awe of the control you have over me and your creativity in teasing me. I was also haunted by the memory of that time you instructed me to masturbate at work, but stop before release. Although I did not enjoy a release that time, it was absolute heaven to be allowed to enjoy an unfettered erection and wank in freedom.

This time was very different. As I began to stroke my restrained penis I felt the pain of my chastity chains digging in. My penis desperately wanted to get fully erect, but the chains viciously prevented anything of the sort. I almost cried as I realized that not only would I be denied a pleasurable release, I was also to be denied the pleasure normally enjoyed while playing with myself. Instead I had to endure intense pain as I attempted to get excited enough to do as you instructed.

After quite a while of struggling against the pain I could finally feel the cum in my balls getting ready to release. Unfortunately, not only did my chastity chains prevent me from experiencing any pleasure, they also prevented the cum from easily rising into my penis. It was like there was a plug that was stopping anything from getting through. I had to increase my struggles until it felt like I was finally going to release.

At just that moment I did as I knew you wanted and stopped masturbating. And just like the time a few weeks ago when we chatted, the semen began to dribble out in a pathetic leaking drip. No explosive release, no pleasure, no enjoyment. In fact it almost felt like it was burning as it continued to dribble and leak. It just kept dripping out in a huge quantity and then gradually stopped.

And now I find myself more frustrated than ever. I am thankful that you allowed me to release the pressure in my balls so soon this time, but I miss the pleasure of unfettered erections and release so very much. Previously I thought extended chastity was the most difficult thing to endure, but what I am enduring now is so much more intense. I never thought I could get this desperate!

In chastity for your pleasure