A Ruined Orgasm

Fortunately for me, I was able to chat with Ms Lee the night before she expected me to try to milk myself at work again. She told me that I was lucky that I had gotten hold of her due to her busy schedule. She proceeded to tell me that during the course of one week she would be having sex almost every other day, as well as other pleasant events such as breaking in the dildo harness I had just purchased for her.

I was nearly insane with jealous frustration as I heard about her frequent sexual adventures, all while I was entering my third month in chastity for her pleasure. While she was free to have sex whenever she desired I was reduced to begging to be allowed to try to milk myself – without touching!

When I told her that she had my penis straining like mad against my chastity sleeve she replied:

good! put plug back in then & rock if you want

When I told her that I was now chastised, pantied AND plugged for her, she replied:

lovely!  rock away and see if you can milk yourself while we talk

As she proceeded to tell me more about her sexual escapades I could feel my penis straining even harder in my sleeve.  I told her that I felt like her cuckold, denied pleasure while she was free to enjoy sex all she pleased. Sne increased my frustration even more by telling me:

if you were here, i’d be taking you with me to my sex guy, binding you, & forcing you to watch & clean us both up, while chastised and plugged. i’d make you beg me to fuck you while you were on your hands and knees and his cock was in your mouth i’d make you keep your eyes open while you blew him so you could watch that cock in your own mouth  and yes, you would be plugged at both ends –  nobody fucks you but me, though

fantasize on that for a while. rock & try to milk yourself. you may touch only the head of your cock with only one finger.  i’ll wait

I desperately tried to milk myself, but even touching myself with one finger did not do the trick. Next Ms Lee told me:

Well, honey, i want you to cum, but i want it to dribble.  SO do this: keep chastity sleeve on, but you may touch. rock the entire time. when you feel yourself just starting to cum, STOP TOUCHING and let it finish on its own.  I’ll wait.

It took a while, but I desperately needed release so I masturbated like a naughty little boy, frustrated by the restraining chastity sleeve. I couldn’t achieve anything close to a real erection, but between two months in chastity and all the teasing I was enduring I finally was able to start cuming. The chastity sleeve had just the effect Ms Lee desired and all experienced was a pathetic dribble as two months of cum was released. No pleasure, no explosive ejaculation, just a constant dribble.

Ms Lee was pleased with my performance and chatted some more as she prepared to go out for the night. She increased my frustration as she told me she expected some more pleasurable sex that night. Then treating me like her little cuckold she told me:

Get some rest. You were a good boy for me and you’ve done well

Experiencing my reward

I was quite blind sided by the ‘reward’ Ms Lee granted me in return for my two incredibly frustrating months in chastity. I had thought I would be allowed to milk myself in privacy, but she had added an extremely devious twist. The next morning I sent her this message after preparing for ‘my reward’:

I am at home right now, I have just finished getting prepared as you instructed. I am rocking on my butt plug as I type this, with my desperate penis straining against my chastity sleeve, tucked inside my pink & black thong. It is difficult, but I am stopping myself from getting too worked up since I understand that you do not want me to attempt to milk myself until I am at work.

It is going to be so embarrassing to do this at work. The worst part might be trying not to make too much noise, but just the idea of what I’ll be doing is going to make me so self conscious. Obviously I will have a very hard time keeping my mind on work today.

One thing that will be constantly on my mind is you. Every time I take a step I feel that butt plug in my rear and every time I sit down (gingerly!) I think of you again. And of course every time I rock on my plug or feel my penis strain against my sleeve I’ll be thinking of you.

I also must admit that I can’t stop thinking about you going out on dates with real men while I am in chastity for you. That frustrates me to no end! I do sincerely hope that you have a very good time with them as your pleasure is what I crave. I love to see you happy and pleased.
I just realized that I am now in my THIRD! month of chastity for your pleasure.

In my 61st day of chastity

Mid way thru the day I sent her this update on my situation:

This is SO frustrating! I am grinding & rocking in my chair like crazy, trying not to make too much noise. When I’m not grinding I’m clenching and releasing my anal muscles, caressing my anal plug with my rear. I have been doing this for about an hour so far, with some short breaks when my rear gets tired, although the clenching never seems to stop. My greedy rear seems to have a mind of its own and can’t get enough of my plug.

Although I am extremely desperate, I do not feel any milking or
leaking going on yet. I will continue trying through the day.

Frustrated, pantied, chastised and plugged for your pleasure

I then sent her this message after arriving home that day:

I am home now and I’ve removed the anal plug from my rear. It was quite a relief to take it out. It has been a long while since I’ve used an anal plug all day so I’m not used to it. Unfortunately, I did not get the other relief I’ve been so desperate for. Although I really got into grinding and rocking on my plug at times, I was unable to milk myself

After this excruciating day I expected Ms Lee to have mercy on me. I was certainly not expecting this reply which I then received from her:

Lovely.  Same thing tomorrow.

Two months in chastity & my reward

The next few days in chastity were the ultimate in frustration. My hormones were in a turmoil and my penis was constantly straining against my chastity sleeve. When I finally reached two months in chastity for Ms Lee’s pleasure I received this message from her:

Congratulations on being in chastity for two months!  You are doing very, very well and I am extremely pleased with you.

Although I was extremely desperate for releif, I was more than satisfied with the state of things since I had managed to please Ms Lee. I was ready to continue without release when I received a second message from Ms Lee:

Excellent!  A full 60 days in chastity at my request.  I am very, very pleased with you and your begging has been steady and sufficient.  Let me reward you. Tomorrow I wish you to wear your butt plug to work.  Do whatever you want while you sit at your desk–rock, whatever.  It is my wish that you attempt your milking through your butt plug while at your desk at work.  Whether it is or not, you are not to remove that butt plug until after you walk in the door of your home after work.

A humble plea

After being warned that I was not begging sufficiently on a daily basis I began doing so quite diligently, in fact usually multiple times a day. Here is a sample of one of those daily beggings:

With every additional day of chastity my frustration mounts almost exponentially. My penis throbs constantly within my tight chastity sleeve, keeping you always on my mind. My desperation has reached the point where it is absolutely breathtaking – I can feel my pulse race when my frustration builds.

So I am back on my knees where I have been so often lately, begging you to PLEASE, PLEASE, PLEASE consider my plea to be allowed to try to milk myself. In no way am I asking to be allowed to get any form of pleasure from this, I merely need so badly to relieve the intense pressure in my balls. Right now I can feel them swollen and desperate to release as my penis throbs constantly within my sleeve.

Instead of being allowed any form of pleasure from this milking, I beg you to allow me to use the milking chains I fashioned to prevent any erection at all, most likely resulting in my production dribbling out slowly with no pleasure derived. Then I will beg you to reset my ‘chastity clock’ back to zero, as if you had just allowed me to have an enjoyable, unfettered release. With my ‘clock’ reset to zero I will in addition beg you to start me in a new, long, very extended period of chastity so I can further demonstrate my devotion to you.

Today is my 56th day in extended chastity for your pleasure. I am only 4 days away from reaching an unbelievable 2 MONTHS in chastity. I would never had thought it possible for me to go this long without any form of release. I think I am beginning to understand just how serious and intense your dominance can be.

If it pleases you to see my chastity continue, to two months or even more, than that is what I desire also. I do not want to disappoint you, I only want to see you pleased and happy. But I must humbly ask for you to consider my desperation and frustration as I beg to be allowed to try to milk myself.

In my 56th day of chastity for your pleasure

More begging

The very next day after receiving Ms Lee’s reprimand that I was not begging sufficiently on a daily basis I sent her this sincere message of begging:

I am quite concerned that you felt I was not begging sufficiently enough on a daily basis. I am truly desperate beyond belief and I’m constantly thinking about my need for a milking. I find it absolutely mind boggling that I am less than a week away from reaching two months in chastity for your pleasure. The main reason I have been able to control myself this long is the thought that my extended chastity pleases you. To endure my denial I have had to suppress all thoughts of my need for sexual pleasure and stay completely focused on yours, as I should.

I also find myself very focused on the thought of worshiping at your rear. I feel so submissive to you now that I feel a great need to demonstrate the level of my devotion in such a way. I hope you find it pleasing that I feel such an intense need. I would love to spend literally hours kissing and rimming your wonderful rear while using my fingers to pleasure your pussy. Since my pleasure is so often denied, and you feel my penis is inadequate, I would have to become an expert at pleasing you with my fingers. While I was rimming you I would concentrate on your pleasure, keeping myself tuned to your rhythm and desire. My tongue would tire, but I would continue. My fingers would tire, but I would continue. Your pleasure is what I would concentrate on, driving my tongue in deeper and keeping you excited.

Only after you were satiated would I then begin begging for my milking again. I need it so badly and I desperately need your permission for this. I am on my knees again pleading with you to consider my need and frustration. PLEASE, PLEASE let me releive the intense pressure in my balls! I need this so badly.

In my 55th day of chastity for your pleasure