Male Milking and the Benefits for a Submissive

Ms Lee currently has me committed to the goal of learning how to milk myself anally. She wants me to become proficient enough to be able to milk myself solely from stimulating my prostate without touching my genitals at all. Me Lee has tried to have me learn how to milk myself before but this time it is obvious that she is serious and will not relent until I succeed. For my part I am determined to learn how to milk myself for two main reasons.

First and foremost I am determined to learn how to milk myself because it will please Ms Lee. Over the course of the last few months since she took me back as her property I have become ever more submissive to her and I am more desperate than ever to please her. It is clear that Ms Lee sees this as a major step in my journey as her property and I am anxious to go down this path. The other reason I am interested in learning how to milk myself is to eradicate the pigmale inside me. My pigmale urges continue to distract me from focusing on Ms Lee’s pleasure and have gotten me in trouble when I have bothered her with my concerns about when I might be allowed a pleasurable release. I was quite distraught when this occurred because I am truly interested only in her pleasure but sometimes my pigmale urges get the better of me. I am hopeful that when I learn how to milk myself that my pigmale urges will cease to distract me.

There are two main parts to my program of learning how to milk myself. The first is to search the web for information on how to milk myself. There is a wealth of information available about prostate milking including many excellent videos as well as tutorials and blogs. The second part of my program involves my practice sessions when I actually try to milk myself. I have two anal dildos that I have been using in my practice and I am also interested in purchasing an Aneros anal dildo which is specifically designed to enable prostate milking. Here is the link to the Aneros dildo I am interested in:
Helix Trident

One of the first things I learned about prostate milking is that long term chastity is necessary in order to ‘prime the pump’. I have learned this from my readings as well as my own personal experience. Prostate milking is nowhere near as intense as masturbation using your hands or actual sexual intercourse. Stimulation of the prostate is pleasant, but requires the desperate need generated by long term chastity to enable successful milking. I have voluntary given up my weekly opportunities to beg for permission to milk myself since it is recommended that a male be in chastity for a month or two before prostate milking becomes easy to achieve. I expect that once I become proficient at milking myself that long term chastity may not be required but for now I think it is absolutely necessary.

Another important thing I have learned about prostate milking is that it can’t be rushed. Masturbation using your hands can be accomplished in as little as a minute and I must confess that I rarely last much longer. Long term chastity and denial have ruined my ability to hold back and on the rare occasions when have been allowed a pleasurable release I have been embarrassed at how quickly I release. But prostate massage is very different. It can take five to ten minutes just to get really warmed up. Even then you can’t just force a release, it must be coaxed with patience and persistence.

I begin my anal milking practice sessions by getting comfortable, taking off all clothing except my panties. I then get into position lying on my back with my legs slightly spread. I then take my well lubricated anal dildo and slowly begin inserting it into my greedy rear. As I do so I meditate about Ms Lee and my submission to her. This helps to get me into the proper state of mind. I approach my attempts at milking myself in a relaxed manner, unlike pigmale masturbation which is a rapid, frantic race to ejaculation.

As my anal dildo slides further into my rear I gently press it upwards towards my prostate. Both of my anal dildos vibrate, producing a pleasurable feeling as I massage my prostate. The pleasurable feeling I experience builds up slowly and never reaches the heights of intense pleasure that I used to enjoy when masturbating. It takes a long time but gradually I get warmed up and begin rocking about as my dildo teases my prostate. My movements become more frenzied as I slide my dildo in and out.

As I thrust my dildo in and out of my desperate rear I usually find myself thinking about being taken by Ms Lee’s strap on. I find a perverse pleasure in experiencing sex like a female, desperately thrusting my hips as I attempt to pull the dildo deeper into my ass. I gradually build up my tempo and soon I am gyrating like mad, ramming my prostate against my anal dildo. I keep this up for 10 or 20 minutes until I collapse in exhaustion and frustration. I am hopeful that as my time in chastity increases I will be able to succeed in milking myself but so far I have been not been able to do so.

Although I have not yet succeeded in becoming proficient at milking myself I have already begun to appreciate the benefits of male milking. One important benefit is that I now have an effective and acceptable way to channel my pigmale desire for sexual relief and pleasure. When I begin to feel desperate for sexual stimulation I no longer think about touching myself and masturbating, instead I respond by finding an opportunity to practice milking myself. I think this is part of a rewiring process that is going on inside of me where my pleasure center is migrating from my penis to my anus. When I think about this I realize that Ms Lee had provided me a way to avoid the feelings of guilt that I experience when I am tempted to touch myself for sexual pleasure. I know that she is deeply disappointed in me when I express an interest in touching my penis for pleasure but I am also aware that she enjoys seeing me pursue my relief via milking of my prostate.

I know that Ms Lee will be pleased if master male milking as my primary and possibly sole method of sexual release. I suspect it will amuse her to have eradicated my penis as a pleasure organ, permanently rewiring me so that anal sex is the only sex life for me. I will no longer enjoy the explosive sexual release that comes from touching myself and masturbating but I hopefully will get relief from the desire for such pleasure. If I can please Ms Lee and avoid the pigmale temptation to touch myself I will be thrilled. These are major benefits that I believe will make me a much better submissive for Ms Lee.

Resource links:

The Forbidden Art of Prostate Milking

https://www.tumblr.com/herservant/63145969570/prostate-massage

http://wiki.malegspot.com/index.php?title=Understanding_your_body
https://prostatemilking.wordpress.com/

Prostate Masturbation Tips and Techniques

My Ten Commandments

As Ms Lee has tightened her ownership of me an extensive list of her expectations has developed. I take these expectations very seriously as the consequences of failure are quite severe. I have earned the wrath of Ms Lee in the past for failing to live up to her strict expectations and the punishments she meted out are seared into my mind and cause me to scramble every day in a desperate attempt to please and satisfy her. I worship Ms Lee as my Goddess and her expectations are the ten commandments that form the focus of my daily life:

1) I am always to refrain from touching myself in a sexual manner without Ms Lee’s permission. My genitals are her property and are no longer available for my pigmale pleasures. I must beg Ms Lee for permission to touch myself, but only if she has given me permission to beg.

2) Every day I put my chastity sleeve on after taking my shower. It stays in place protecting Ms Lee’s property from any unauthorized touching or erections until I get ready for bed.

3) Every day I pick out a fresh pair of panties to wear, I no longer wear male underwear. I am also kept busy hand washing my panties on a regular basis, I would never dare present myself to Ms Lee in panties that were not in pristine condition

4) I must keep the area around my panties shaved and properly groomed at all times. There is never to be a single hair visible.

5) Every morning I conduct my morning worship session for about 15 minutes while properly plugged.

6) Every day without fail I make sure to contact Ms Lee in some way.

7) Every day I stretch during my exercise routine and meditate with Ms Lee as my focus.

8) On a weekly basis I post an update to the blog I maintain for Ms Lee.

9) On a monthly basis I send Ms Lee a monetary tribute as a demonstration of my devotion to her.

10) I apply myself to learning a variety of advanced study topics as determined by Ms Lee’s desires for my education and training so that I might better serve her. I am currently working on three areas of study:

A) I am learning how to provide professional quality pedicures accompanied by numerous pampering additions such as foot/leg messages along with the proper oils and lotions. I am searching out and studying web pages concerning how to give professional pedicures and I am also planning on getting a pedicure myself as soon as I find an opportunity sot that I will better understand the process.

B) I am learning how to milk myself anally, without touching myself. I am practicing this daily as well as searching out web pages with tips on milking yourself and proper tools. As I mentioned in my prior blog entry I suspect that Ms Lee has a substantial change in mind for my future ‘sex life’ once I master milking myself.

C) Self study – As time allows I am studying how best to please Ms Lee – what meals she likes, etc. I need to become on expert on pleasuring and satisfying Ms Lee

A new goal

During my last session of begging Ms Lee for permission to milk myself I mentioned that I felt tortured by the desperate desire to touch myself and I said that I thought I would be happier if she could completely eradicate the pigmale inside of me. She kindly agreed to help me and told me to learn how to milk myself through my prostate with out touching my penis or scrotum. She wants me to keep her appraised of my progress and let her know when I have reached the point where I can milk myself at will.

The very next day I began practicing to learn how to milk myself, using my ‘bigger tool’:

Fortunately there are many websites with information on learning how to milk yourself such as these:
prostate milking
forbidden art of prostate milking
pleasure mechanics

I must admit that I have mixed feelings about this new goal that Ms Lee has set for me. On the one hand I am looking forward to having the pigmale inside of me eradicated or at least harnessed for Ms Lee’s purposes. I believe it will please her greatly when I have learned how to milk myself and I am always anxious to find ways to please Ms Lee. But I am also concerned about the changes in my ‘sex life’ that achievement of this goal will bring about.

Ms Lee has not stated exactly how learning to milk myself will result in the eradication of the pigmale in me but I suspect that my opportunities for touching myself will be strictly limited in the future, if not fully eradicated along with the pigmale in me. It is the pigmale in me that creates the maddeningly frustrating desire to touch myself so if the pigmale is eradicated will the desire to touch myself also be eliminated? I suspect that Ms Lee will allow me to milk myself frequently but I don’t know if that will completely eliminate the desire to touch myself. Even if the desire for a release is satiated by my milking I may still desire to touch myself for the sheer pleasure that stroking an erect penis brings.

Of course stroking an erect penis is the act of a real man and Ms Lee has made it clear that I am not a real man. I am her property and permission to touch her property is only granted at her whim, if it pleases her. It is quite possible that once I learn to milk myself Ms Lee may no longer see any need to allow me to touch her property. I can’t begin to imagine what it would be like to no longer touch myself at all, nor what it would be like to only experience a release by milking myself with no touching allowed. But if Ms Lee expects this to become my new ‘sex life’ then I will be anxious to please her regardless of how significant the changes to my sex life might be.

I am not entirely sure how this will all turn out and I don’t know if Ms Lee will come right out and tell me exactly what she expects. She frequently likes to let me sort things out for myself, probably because I learn better that way.

Advanced Study

As time goes on I have become more and more obsessed with the goal of pleasing and satisfying Ms Lee. I have learned that catering to my own greedy pigmale desires leads to nothing but selfish, fleeting moments of enjoyment but toiling for the pleasure of Ms Lee provides me with a deep sense of fulfillment and satisfaction. I have found that I am most satisfied when Ms Lee is pleased with my performance, I have become like a dog who craves its master’s approval above anything else. As a result my own desires and pleasure have become irrelevant, my focus is now solely on how I can better please Ms Lee and provide her with excellent service.

As my obsession with pleasing Ms Lee has grown I have found myself more carefully studying her preferences. At first I didn’t fully realize how serious my studies had become. In the past I had learned that she preferred live plants instead of cut flowers and I had spent considerable time learning how to clean her panties (https://propertyofmslee.wordpress.com/2013/02/18/ms-lees-panty-washing-boy/). But more recently I found myself considering going to formal classes to learn how to properly provide massages and pedicures. At first I will probably study on my own as I did with panty washing but eventually I am sure that I will be attending professional classes. I want to be able to provide Ms Lee with better service than she could receive at the finest spa.

My immediate priority is to learn how to provide a proper pedicure since Ms Lee’s feet are such a focus of mine. I hope to become good enough at giving pedicures to please Ms Lee and convince her that I would be capable of tending to her beautiful feet.

I am equally serious about learning how to prepare scrumptious meals for Ms Lee, prepared to her preferences and specifications. I am currently studying her facebook in order to learn what sort of food she likes and i suspect that food preparation classes are in my future also. I may not become a professional chef, but I do need to become proficient at preparing good tasting food that is pleasing in appearance and made to her liking.

More importantly it has occurred to me that I need to become expert at reading Ms Lee’s moods so I can better understand her desires without her needing to spell things out for me. I need to be able to tell when she is in the mood for sexual pleasure and when she would prefer non sexual pleasure such as a foot massage or other such service. I need to learn how to carefully observe her and tune into what she is in the mood for. To do this properly I need to put aside my own selfish interests and fully immerse myself in her personal world, focusing on nothing but her pleasure and satisfaction.

To have any hope of convincing Ms Lee that I am dedicated to her pleasure I need to become like a full time student focused on learning everything possible about what pleases or amuses her. I need to learn what she likes to eat and drink, what kind of music she likes and how she likes her home taken care of. I need to study her as if I was working on a masters degree. Once I had achieved that level of proficiency in pleasing and satisfying her I would then have to step things up and work on my doctorate. Even then I would not stop studying how to please her, my efforts will be a life long endeavor.