CBT for Ms Lee

During my recent chat with one of Ms Lee’s boys the subject of experiencing punishment for her pleasure came up. I mentioned that after nearly two months in chastity I was desperate to please her and would be anxious to mark myself to demonstrate my submission to her. I had previously whipped myself for her until red stripes were visible on my rear. After I finsihed chatting with Ms Lee’s boy I had a chance to talk to her and brought up my desire to please her in this manner.

I was not at all prepared for her response. I had told her I was desperate for release and she had responded:

oh fine. try to milk yourself. no touching, though

When I then brought up the suggestion of marking myself for her she replied:

if you are able to milk yourself, i want you to clean it up, then immediately mark yourself –on your penis & scrotum  pics of that plz. i’m a big fan of cock and ball torture

I was not at all prepared for this. Whipping my rear until it was marked was bad enough, but I couldn’t imagine the pain that would be involved in marking my cock and balls. But I also couldn’t imagine disappointing Ms Lee so I resolved to do as she expected.

The next morning I sent Ms Lee this message regarding my effort to do as she expected:

This morning I attempted to milk myself, but after 20 minutes of desperate grinding and humping I was only able to produce what I would consider pre cum. I think that those times I thought I was in danger of an unauthorized release were false alarms. I slowly built up to the same sense of excitement this morning, but then discovered it was not enough to get me to produce. Quite frustrating! I think I may need one of those anal dildos I’ve heard of (Aneros?), perhaps you might allow me to get one as a Christmas gift from you.

At times I was humping so madly that I found myself using my anal muscles to try to pull the plug in deeper. I am embarressed to admit that I actually began to wonder if that was what it was like for a woman when they are being penetrated.

Although I was not able to fully milk myself, I thought it might please you if I marked myself as you described last night. I used the same belt that I had used previously to mark my rear for you.

You had commented that I would not be able to really mark myself, that I would probably only be able to redden myself. I also remembered how hard it was to mark my rear with my belt, so I spent 10 minutes whipping my cock and balls as hard as I could. I was concentrating on hitting the shaft of my cock as I thought that would redden easiest. It almost brought tears to my eyes every time the belt happened to hit the head of my cock. I would have continued, but after 10 minutes my knees were shaking so badly from the pain that I could hardly stand up. As a matter of fact, they are still shaking right now.

When I stopped whipping myself and looked at the results, I saw why my knees were shaking so bad. I had managed to inflict some nasty marks on my poor, punished cock, as you can see in the attached photos. I have more photos I will send later.

My penis is stinging from the pain of the whipping and my knees won’t stop shaking. However, if my attempt to mark myself pleases you then the pain is more than worth it.

In my 53rd day of chastity for your pleasure,
wearing my red panties with garters

I expected that Ms Lee would be impressed with my desperate attempt to please her and the intense pain that I had endured. I was shocked when her reply indicated that she was not impressed or pleased in the least:

Gross. Trim.  Stop sending me pictures of you in need of a trim.  You know by now I don’t like that.  Take care of it and mark yourself again after trimming.  Also,you may purchase that for yourself as a Christmas gift from me.
Happy Friday!
I was intensely disappointed that I had failed to please Ms Lee and prompltly did as she expected, sending this message in reply:
Attached are photos of my cock after I re-trimmed and re-marked it. It was incredibly painful to whip my cock again after it had already been beaten so badly, but I deserved it for not properly trimming myself the first time.The first time I whipped my cock it was the left side of it that got marked, since I was using my right arm, striking down and over. This time I worked on the other side of my cock (the right) to even the marks up a bit. The first two photos show the result of this.(the cut on my thumb is from Thanksgiving).

The 3rd photo shows the left side of my cock with darker bruises than before. My cock is changing color already, but I’m sure it will be at least a week before it clears up.

I will put my chastity sleeve back on now, I think my cock is swollen a bit from the whippings. The sleeve felt very tight after the first whipping and I felt a constant stinging/burning sensation as it strained against the sleeve.

I can’t begin to describe how happy I was when Ms Lee then expressed her satisfaction with my performance:
Lovely,  I’m happy.

One Response to “CBT for Ms Lee”

  1. Jabbertype2 Says:

    Leebox2…

    Fantastic blog post, saw on…

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