A dry year

As the year draws to a close I looked back over my blog postings and realized that 2011 has been a year of very few releases for me. It seems that this year Ms Lee has grown much more fond of seeing me in extremely extended chastity for her pleasure. There were a few instances when she allowed me to release more frequently, but there have also been multiple times when she kept me in chastity for over two months, something I never experienced before this year.

In case you are interested, below is a list of my releases this year, including notes as to whether I enjoyed a pleasurable release, a ruined orgasm or just a milking. This year is also the first time I experienced ruined orgasms and milkings. Ms Lee seems to be growing more fond of these types of releases for me, with pleasurable releases becoming quite rare indeed.

I don’t have a record of my releases prior to April 1 of this year, but the list below certainly provides a good idea of Ms Lee’s penchant for extended chastity.

April 1 – Pleasurable release

May 12 – Pleasurable release

July 13 – My first ruined orgasm

July 28 – Another ruined orgasm

August 7 – Pleasurable release

September 1 – Another ruined orgasm

October 8 – My last pleasurable release of 2011

December 18 – My first milking

I calculated that the average time between my releases this year has been a little over a month (34 days). In case you think this is overly generous, you may also want to consider that it has been 81 days since my last pleasurable release.

An early Christmas gift

While I was marking my penis for Ms Lee she graciously agreed to allow me to purchase an anal dildo for myself as a Christmas gift from her. She was even kind enough to inform me that I did not have to wait for Christmas before trying out my new toy.

I eagerly visited my local adult store to shop for my Christmas gift from Ms Lee. After looking over the available anal dildos I selected a nice red vibrating model that looked like it could help me deal with my ‘problem’. I have attempted to milk myself with a regular anal plug, but I have been unable to succeed. Due to Ms Lee’s no touching rule it is quite difficult to reach a level of sexual excitement necessary to achieve a release. Using the anal plug  just gets me extremely frustrated as I near the edge of a release, but am unable to reach it.

I waited until after my Worship session the next morning before I tried out my gift from Ms Lee. I wanted to use my Worship session as an opportunity to properly thank Ms Lee for her gift before I opened it up. This was also a nice ‘warm up’ since my Worship session involves putting a 2 inch wide anal plug up my rear.

Once my Worship session was complete I removed my plug and inserted my new anal dildo. The anal dildo is custom designed to rub up against my prostate and has a variable vibration feature. Here is a photo of my Christmas gift from Ms Lee:

The two inch anal plug I used during Worship opened me up quite nicely so that the anal dildo slid in with no trouble. I located my prostate and pressed the tip of the anal dildo against it and then turned on the vibration. The sensation was incredible as I felt my prostate react to the stimulation. I started grinding and pressing against the dildo, trying to increase my excitement.

I soon found that this sort of sexual stimulation was quite different from normal male masturbation of the penis. Instead of rapidly reaching a peak of excitement I had to work at it, gradually building up my level of sexual excitement.

I also had difficulty finding the right position to achieve maximum excitement. I first positioned myself on my knees, but it didn’t feel like I was getting in deep enough. I tried lying on my side and found that I could more easily reach my prostate and began gyrating like mad. But even this was not enough and my frustration grew. I wanted more! Finally I laid on my back and spread my legs, arching my back upwards. This seemed like the best position to allow maximum penatration and my gyrations increased.

As I bucked and ground against the anal dildo I realized that I was positioned just like a woman that was being penetrated by a man. I was also responding in the same manner, thrusting up and back in an attempt to increase my excitement.

I also realized that the sexual excitement I was experiencing was quite unlike that a man normally feels. I did not enjoy a strong erection and a rapid build up to the point of explosive release. Instead I experienced a maddeningly frustrating, slow build up, which caused me to thrust and gyrate ever faster. But no matter how hard I tried, there was to be no joyful, explosive release for me.

Eventually I also realized that my penis was leaking what seemed like pre cum. I was surprised at first because I expected to feel something when my penis released fluid, but there was almost no sensation at all. The fluid just slowly leaked out, with no pleasure or satisfaction achieved at all.

Finally I collapsed in exhaustion, unable to grind or gyrate any more. I looked at my belly and saw a small pool of nearly clear fluid, nothing like the thick blobs of semen that I would produce from a normal masturbation. I also did not feel anything like the normal satisfaction that masturbation provides. Instead I felt frustrated and deprived.

I also soon found that while the pressure that my extended chastity had produced was now eliminated, my frustration and desperation was unabated. If anything I was even more frustrated and desperate than ever.

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.

A Chat with one of Ms Lee’s Boys

Recently I was fortunate to begin a chat with Ms Lee while one of her boys was with her. She was kind enough to allow me to chat with him, which gave me the opportunity to learn more about what pleases Ms Lee.

One of the first things he asked me was if I was into pain. He told me that he had met Ms Lee when she was trying out a flogger that he had made. She tried it out on him and it turned out that she was better than anyone that had ever used a flogger on him. Her boy continually stressed that Ms Lee was a loving, caring person, but that with a strong whip in her hand she can give him the stings of pleasure, so that he may give her the pleasure of his pain.

Her boy told me that Ms Lee is a very sexual person and that when a boy is allowed to please her he is compelled to give all he has. He pleases her orally at least once a day, sometimes more. He told me that she also loves foot massages and that he gets to kiss her beautiful feet.

Her boy also told me that Ms Lee has a beautiful round ass that he enjoys rubbing and massaging. And of course he also enjoys performing his chores for Ms Lee.

I really enjoyed chatting with Ms Lee’s boy and I learned a lot from him. Most importantly he reinforced my understanding the Ms Lee is the perfect combination of dominance and caring.