Still Practicing

It has been a month since my last release and I still haven’t had any success with milking myself. I am getting quite frustrated and desperate however and that seems to really be helping me get closer to achieving my goal. One of my problems is that things have been fairly hectic in my life lately, which happens too often. As a result I have not been relaxed enough to truly enjoy my milking practice sessions and really get into it.

One good thing is that I have begun to truly enjoy my milking sessions, enough so that I no longer miss masturbating so much. Pleasuring myself anally is nowhere near as intense and quick as masturbation but it provides a different, more lasting type of pleasure. I actually appreciate this quite a bit since I was not able to hold back for long on the infrequent occasions when Ms Lee allowed me to touch myself. I think that my years of extended chastity have ruined my staying power.

While my goal is to learn how to milk myself without touching myself I am also learning to enjoy anal pleasure for its own sake even without producing anything. I like the feeling of my dildo massaging my prostate and I enjoy the pleasure of filling my greedy rear and ramming my dildo in and out. I am learning how to appreciate a very different sex life than that enjoyed by a ‘real’ man but it seems appropriate for me as the property of Ms Lee.

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

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.

Plugged again

I have become very focused on Ms Lee and her pleasure but she apparently thought that my focus on her could be improved. She recently told me that I was to wear my butt plug for at least 5 consecutive hours a day until my next session of touching myself. Although I have been using my butt plug during my daily morning Worship sessions it has been quite a while since I have endured it for anything near 5 hours a day so there was no doubt that Ms Lee’s latest expectation for me would be quite effective at improving my focus upon her.

My first day of being plugged for 5 hours was quite an ordeal. Within an hour or two of being plugged I was already feeling nearly unbearable discomfort as the plug tortured my rear. I knew I was walking funny and it was beginning to get difficult to sit down properly. By the third hour or so my poor rear was starting to sting from the rubbing of the plug and I was getting desperate to remove it. But no matter how bad I was hurting I was determined to be obedient and do as Ms Lee expected. I am always desperate to please her and I did not want to disappoint her on my first day of being plugged. When I finally reached the 5 hour point I promptly removed my plug, relieved to have the invader removed. I went to bed nearly exhausted from my ordeal and did not want to even think about wearing the plug the next day.

But the very next day I obediently did as Ms Lee expected and inserted my plug for another 5 hour ordeal of discomfort and distress. To make matters even worse I needed to mow my lawn that day. I have a large lawn and use a riding tractor which naturally vibrates quite a bit. As I bounced around on the tractor my plug kept getting rammed further up my rear and the vibrations of the tractor were driving me crazy. It felt like I was bouncing on top of a vibrating anal dildo. Normally riding the tractor makes me feel manly, but not when I’m chastised, plugged and pantied!

By the third day I was beginning to get used to wearing the plug but as the discomfort from the pain subsided I was presented with a new torment. It was getting to the point where the plug was teasing my poor penis relentlessly as it pressed against my prostate. As my penis strained against my chastity sleeve I felt a desperate pigmale desire to take Ms Lee’s property in my hands. My frustration was made all the worse as I felt my sissy ruffled panties embracing my chastised penis. Here is a photo of my plugged rear embraced by my white sissy ruffled panties:

As I got more frustrated and fought the urge to touch myself I began to squirm in my seat, causing my plug to press even harder against my prostate which in turn got me even more excited and frustrated. My plug was driving me crazy but I kept thinking about Ms Lee, hoping she would be pleased with my obedience. I also suspected she might be amused at my discomfort but I was glad to endure it if that pleased her.

I still have a few days to go before I will be allowed to beg to touch myself again. Even if my begging satisfies Ms Lee and it suits her whim to allow me to touch myself it frequently pleases her to delay the approval for a few days. This means I probably still have quite a few days of being plugged to look forward to. The good news is that this will provide me with many more opportunities to sharpen my focus on Ms Lee as I endure more discomfort and teasing for her pleasure.

Feeling like a sissy

I’m not sure exactly when the change occurred but I’ve realized that my reaction to wearing panties has gradually changed from embarrassment to anticipation and excitement. I’ve always gotten hard and excited in response to the embarrassment I experience when wearing panties but now my excitement is also due to the pure pleasure I obtain from wearing them.

Recently I have had some discussions with Ms Lee because I have been struggling with admitting to myself that I am a sissy. I have been wearing panties and experiencing chastity for years but I had always felt like a man that was just experimenting with submission. Being told to wear panties was part of that submission and although wearing them got me excited and hard it was always due to the embarrassment I endured. But over time the primary reason for my excitement has shifted from embarrassment to the enjoyment I now experience from wearing panties.

I have become quite obsessed with my pretty panties and I have accumulated a large collection including a number of them with garters and frilly skirts. Plain panties are no longer good enough, I now search for frilly and sexy panties, preferably with a lacy garter belt. I think a primary driver of this obsession was due to the sexual starvation I endured when in chastity. I desperately craved any sort of sexual stimulation and I learned to enjoy the feel of my silky panties embracing my chastised genitals. Attached is a photo of one of my favorite pairs of panties, they include a lacy built in skirt and detachable garters.

Another obsession I had developed due to Ms Lee’s training involves my extensive collection of anal toys. Ms Lee requires that I conduct a morning Worship session every day that includes having my hungry rear stuffed with my anal plug. I have learned to enjoy the sexual stimulation I experience when my plug presses against my prostate. Just like what happened with wearing panties, I have come to crave my morning Worship sessions and the frustrating excitement I derive from having my anal plug tease my prostate. And just like with my panties, my obsession with my anal plugs makes me feel like a sissy. More information on my morning Worship sessions can be found in this blog entry – How i Worship my Goddess

Ms Lee told me that I should not be ashamed of anything that makes me feel good and she encouraged me to embrace being a sissy if that made me happy. While admitting that I was a sissy felt right to me I was still uneasy because of my preconception that all sissies are gay and that many of them wear diapers and act like little children or babies. While these things may be fine for other sissies they are not part of what I am. Ms Lee helped me to understand that I should not worry about the preconceptions of what is ‘normal’ for a sissy and that I should just enjoy those aspects that make me happy.

I am now putting Ms Lee’s advice into practice as I embrace being a sissy. I truly enjoy wearing panties and playing with my anal dildo and I am no longer distracted with the preconceptions about being a sissy that don’t apply to me. Once again Ms Lee has helped me to better understand my submissive nature. I am truly blessed to be owned by Ms Lee and I am very grateful.

A renewed anal focus

As will occasionally happen I have recently been experiencing a few personal issues that have caused a bit of stress in my life. Ms Lee has been very supportive, once again demonstrating her unique approach of caring dominance. Understanding my situation she has allowed me some latitude, but has made it clear that this is not an excuse for me to slack off in my devotion to her. I have continued my duties as her faithful panty washing boy, carefully cleaning the panties that caress her everyday. I also continue to assist her in other ways. I am not sure if it is intended to address my recent stress, but she has also introduced a renewed focus on my anal submission.

During a recent conversation Ms Lee had asked me about my fantasies and I admitted that due to my relentless, extended chastity I have frequently found myself thinking about anal stimulation. Ms Lee’s expectations seem to deviously lead me in this direction. While I am not allowed to touch myself in a sexual manner she does allow one ‘exception’ – I am always free to stimulate my prostate using an anal plug or dildo. The longer I am in chastity, the more desperate I become for any sort of sexual stimulation. But anal stimulation does not provide me anything close to the pleasure and release that I used to derive from wanking like a teenage boy. Instead it leaves me more frustrated than ever, increasing my desperation in an endless cycle. While I do not derive any real complete satisfaction from my anal stimulation I do hope that my desperate attempts please Ms Lee.

One evening after Ms Lee reintroduced the focus on my anal stimulation I inserted my anal plug before I went to bed for the night. I thought I was going to go straight to sleep but I soon became badly distracted by the plug in my rear. I found myself clenching my rear and enjoying the pressure against my prostate. It was quite maddening as I desperately desired a release but the plug did nothing more than tease me. I continued to press against my plug for quite some time before I finally slipped off to sleep, with thoughts drifting in my head of being taken by Ms Lee’s strap on.

I woke a few times during the night and each time I immediately began clenching my rear and pressing against the plug. When I woke in the morning I was so frustrated and excited that I immediately got out my Bigger Tool and proceeded to attempt to milk myself. I was not able to produce anything, but I certainly enjoyed trying. For those who might not be familiar with my Bigger Tool, it is a large, 8 inch long dildo of the sort that a woman would ordinarily use. I had initially began my anal stimulation using one of the slim anal massagers that are popular, but it amused Ms Lee to have me graduate to a ‘bigger tool’. A tool which is much more substantial than my own inadequate member which has been shrunken further as a result of my constant, extended chastity.

Ms Lee now expects me to experiment with different sized and shaped anal toys. I currently have a few standard butt plugs as well as my two anal stimulators. If anyone has any suggestions I would be interested to hear about them.

Playing with my breasts

Every time I dress up for Ms Lee in one of my new corsets I have found myself becoming more and more aware of my breasts and nipples. My corsets frame my breasts very nicely and I can’t help wondering what it would feel like to caress them. I think my extended chastity has also made me quite desperate for any sort of sexual stimulation. Recently I asked Ms Lee if her ‘no touching’ rule included my breasts and nipples. She gave me permission to touch myself there, but told me to keep her ‘abreast’ of my experiences since she was not entirely sure about the idea.

The first time I tried it I restricted myself to just lightly rubbing my breasts and pinching my nipples. I found the sensation quite pleasant and although I eventually felt my penis become a bit excited I think I actually enjoyed the subdued pleasure experienced by my breasts even more. Even after I stopped touching myself I continued to feel a warm, pleasing feeling emanating from my breasts. I found the pleasure to also be a bit frustrating, similar to the teasing, limited sexual thrill I derive from anal stimulation.

Today I tried  playing with my breasts while using my anal vibrator. I expected things to be a bit more intense so I decided to use clothes pins on my nipples to heighten the experience. Before I tried this I put on my chastity sleeve, including the viciously tight fifth chain that pleases Ms Lee so much. She enjoys having my long deprived penis painfully restrained and I wanted to insure that my sexual stimulation was focused solely on my breasts and my rear. This would leave my penis ignored and limp, hopefully pleasing Ms Lee a bit more.

Once my penis was firmly restrained I began to slide my anal vibrator up my desperate rear. I used to use a small, slim anal vibrator, but Ms Lee wanted me to use a bigger tool. I now use a large woman’s vibrator that is nearly twice as thick and long as my penis is on the rare occasions when Ms Lee allows it to become erect. My bigger tool does an excellent job of stimulating my prostate, driving me to extreme heights of frustrating pleasure. As I began to grind my rear and drive my vibrator further into my rear I began massaging my nipples. As they became excited and began to firm up a bit I attached clothes pins to them, tightly squeezing and pinching them.

With my nipples pinned and the vibrator rubbing my prostate I began to get incredibly excited. I was soon bucking and grinding as hard as I could, my sensations magnified by the pain centered in my breasts. I continued to rub my prostate as the pleasure/pain continued. I was not able to milk myself, but I found I did not care. I think I am learning to better enjoy the limited sexual stimulation that Ms Lee allows me and I have discovered that playing with my nipples adds quite a special thrill to the experience.

I got another ‘thrill’ when I removed the clothes pins. I felt an excrutiating pain as the blood flowed back into my nipples. I immediately tried to rub them in an attempt to releve the pain, but found that it hurt too much to touch them. For a while it felt like the clothes pins were still attached and all I could do was wait for the phantom pain to subside.

I know that Ms Lee will continue to firmly enforce her ‘no touching’ rule with regards to my penis and balls. However, I sincerely hope that she might decide to allow me to continue to touch my breasts and nipples.

Anal relaxation

Once again I must apologize for the delay between postings. I have been dealing with some personal issues that have kept me quite busy and distracted. Things have been so hectic and stressful that I had even stopped wearing panties or enjoying my anal dildos and plugs. I have also been guilty of neglecting to keep in regular contact with Ms Lee and I am very grateful that she has been understanding and sympathetic. We recently had a nice chat that enabled us to catch up on things and I found that I felt much more at ease afterwards. During our chat we discussed my recent fascination with wearing stockings and corsets. I have been having some difficulty understanding why dressing up for Ms Lee excites me so much, but she put me at ease about that also.

Ms Lee put me so much at ease that tonight I dressed up again for the first time in a while. I put on the same pink corset, black stockings and red panties that I was wearing in the photos shown in my last blog entry. By the time I finished dressing up I was so sexually excited that I got out my large vibrating dildo and began playing with it. It took a while to get the big intruder comfortably inside my rear, but once I did I remembered just how much pleasure that huge tool could provide. Soon I loosened up and was gyrating like crazy.

At this point I was so excited that I felt the urge to grab hold of my own tool and masturbate. However I did not have permission from Ms Lee so I kept my hands off her property and returned to the only form of unrestricted sexual pleasure she allows me, rubbing my anal vibrator against my prostate. I was not able to milk myself, but I certainly enjoyed trying. Sometimes I remember the days when I was able to masturbate and release at will, but I am infinitely more satisfied and complete being in chastity for Ms Lee’s pleasure.