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:

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:

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