Shopping Again

Recently I mentioned to Ms Lee that I had an opportunity to go back to Macy’s in NYC, where I had previously purchased panties at her direction. Some of my previous panties had become worn and I thought I could replace them during a trip back to Macy’s. Ms Lee once again found a way to extend my humiliation as she replied:

I only want you buying 1 pair of panties tomorrow.  Then, each time you visit NYC, go buy 1 pair of panties.  In other words, one at a time, per trip, until you have a new week’s worth. Do you understand?

I had thought my need for new panties would only require a single trip to Macy’s, but Ms Lee apparently saw an opportunity to further my embarrassment. I immediately acknowledged my understanding:

Yes, I understand and will do as you instructed. I’ll send you a photo of the panties I purchase today. Do you have any preference regarding what kind or color I buy?

I will be SO embarrassed having to go back to Macy’s every week to purchase a single pair of panties. I am worried that helpful sales lady or one like her will notice my repeat visits and figure out that the panties are for me.

Ms Lee’s response substantially increased the humiliation I was to endure:

Ask the saleslady for help each time.  Something and feminine in your size, tell her.

Released at last

As my week of unfettered masturbation (without release) neared an end I recieved a text message from Ms Lee that drove me crazy with frustration. My next message to her described my reaction:

Your message to me last night made me absolutely crazy with frustration. I got so hard and desperate that I got out my anal plug and slid it up my horny rear end. I then slipped my panties back on and got even harder in reaction to the tease they inflicted on me. I ground and rammed against the plug as I pictured you being rimmed and pleasured. I then began masturbating, trying desperately to stretch out the enjoyment, but knowing it was probably a losing battle. Your text message kept exciting and frustrating me, driving me to stroke even harder. Within a couple of minutes I lost control and exploded, releasing months of pent up frustration.

It was glorious to finally be able to enjoy an unfettered, pleasurable ejaculation. But at the same time I felt disappointment that I was not able to hold out longer and enjoy it further. I felt such an intense sense of release and pressure that I knew I would not be able to enjoy another release before the day ended.

Sure enough, I went to sleep last night without even trying to get hard again. I slept in quite late and had a number of chores to deal with this morning. I am now back in my panties and chastity sleeve even though there is no real need for the sleeve right now. I can feel some slight stirrings in my penis, but I don’t think it will be up to anything today.

I hope you had a great time last night, it was so awesome to get a text from you while you were being pleasured. I would love to hear more about it.

Back in chastity for your pleasure

Unfettered masturbation

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

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

ow!

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

ok, i’m back

good!

lol

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

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