Archive for July, 2015

Plugged again

July 27, 2015

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:

Plugged, chastised & pantied

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.

A Lifetime of Chastity

July 24, 2015

During a recent conversation with Ms Lee she told me to expect to be in chastity for the rest of my life, never to be out of it without her permission. She also told me that I would never again have any sort of release without her permission, nor would I eve be allowed to touch myself in a sexual manner without her permission. She then told me to think about that and then tell her how that made me feel.

I have been in chastity for the pleasure of Ms Lee on and off for six years now but her announcement threw me into shock. There have occasionally been periods during these six years when Ms Lee did not require me to be in chastity and when she did require me to be in chastity I think there was a little voice in the back of my mind that told someday I would be out of chastity again. I never really thought about the possibility that I would never be out of chastity again but I realized that Ms Lee was quite serious about it. She had decided that I would never again be out of chastity without her permission and as her property I had no choice but to accept her decision.

It was very clear that she would never again allow me the freedom to decide when I could masturbate or play with myself. From now on that would be for her to decide and I would be completely dependent on her whim and mood. The more I thought about it the deeper my shock became. I would be permanently sacrificing what most real men value most – the freedom to sexually satisfy themselves whenever and however they please. Of course I am not a real man, I am Ms Lee’s property and I realized that it was presumptuous of me to think I should ever have the responsibility to decide when I could touch myself. Whenever I had been free to do so I soon fell into the habit of masturbating multiple times a day like a little school boy, wasting my time and sexual energy. Ms Lee knew that my sexual energy could be harnessed for a much more beneficial purpose – her pleasure, amusement and satisfaction.

Forever more my opportunities to enjoy sexual pleasure are to be tied to her pleasure. I only experience sexual pleasure if it pleases Ms Lee to have me do so. It does me no good to worry about my greedy desire to pleasure myself because that is no longer my prerogative. If I expect to ever be given permission to touch myself or masturbate I’d better concentrate on making Ms Lee happy because there is no other path open for me. And even if I perform perfectly and provide Ms Lee with pleasure and satisfaction there is no guarantee that I will be given permission. If it suits her whim to deny me just for the fun of it then I must accept that and be happy for the opportunity to amuse her with my sexual frustration. My goal is to please her, not me. Even though my pleasure is tied to hers this is not a two way street. I please her whenever and however I can. She allows me pleasure whenever it pleases her and she is free to deny me for any reason at all.

Whenever I think about sexual pleasure it will be HER sexual pleasure that I focus on, I will never again be allowed to pursue sexual pleasure for myself. Instead I will experience sexual pleasure vicariously through her. This is very heady stuff and I am just starting to realize just how severely I will have to change my approach to pleasure and sexual satisfaction. I suppose it will be as if my own sexual being ceases to be mine to control or enjoy. Instead, whenever I desire to experience sexual pleasure my first and only thought will be to pursue her sexual pleasure and satisfaction.

I must apologize if I am rambling a bit but the idea of lifetime chastity is still shaking me to the core, particularly since I am well aware of how seriously Ms Lee takes it. I am in awe of the times she had me endure months and months of chastity and I have to admit that I am afraid to even think about the very real possibility that she will have me endure that again, perhaps just because it suits her whim at some point. I know that in comparison to past experiences she is being very generous in allowing me weekly opportunities right now to beg for permission to touch myself and I am very grateful for that.

My mind continues to spin as I contemplate a lifetime of strict chastity but I realize that I should be thankful that Ms Lee cares enough about me to commit to a permanent responsibility to oversee my opportunities to enjoy sexual pleasure. I am very fortunate to be her property and I can’t thank her enough for that.

When I presented the draft of this blog entry (up to this point) to Ms Lee she told me she wanted me to express how her decision of lifetime chastity made me FEEL, not what I thought about it. She challenged me, once again, to give her the answer she really wanted, not the one I thought she wanted.

How I feel is overwhelmed. I have been experiencing a mix of feelings which have been difficult to pick apart. The primary feeling I am experiencing is one of losing control. I may enjoy wearing lingerie like a sissy but I am still a man inside and my first instinct is to try to take control of a situation. If chastity was an on and off thing then I still maintain some level of control. But to embrace the reality that I will spend the rest of my life in chastity without a break means that I will never again have control of my own sexuality. I will never again be free to decide how and when I can touch myself or produce. The very thought of giving up any control at all scares me very deeply.

Right behind my feeling of a loss of control is one of acceptance. I know that I am incapable of properly controlling my sexual desires and impulses. I will always fall into a rut of masturbating multiple times a day like a little schoolboy, wasting my time and energy. Being in chastity for Ms Lee provides me with the discipline I am incapable of applying myself. I know it is for the best if I embrace the idea of being in chastity for the rest of my life because I can trust Ms Lee to know what is best for me. Along with acceptance I am feeling a sense of relief, knowing that I will never again have to worry about wrestling with that demon pigmale inside of me. Ms Lee will eradicate that demon.

One other thing I am feeling is uncertainty. I know what chastity is like but I have no idea how things will play out now that I accept giving up any control at all regarding my sexuality. I trust Ms Lee without reservation but it scares me to go into this uncharted land of no control. So I run back to that feeling of acceptance and embrace it. I must let go of control and truly embrace being the property of Ms Lee. It feels good to let go.

Chastity Forever

Feeling like a sissy

July 16, 2015

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.
Red skirted panties

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.

Shaved again

July 7, 2015

I mentioned in my previous blog entry that Ms Lee’s expects me to always keep the area around my panties smooth and free of any unsightly fur. I have been working very hard to maintain a hair free appearance in this area but now Ms Lee has expanded the area where she expects this grooming to occur. In response to a recent photo of my panties that I sent to her she told me that there was some fur on my left leg that distracted from my prettiness. She then told me to correct this situation, asking me if I didn’t want to be her pretty girly boy.

I saw that there was indeed some fur on my left leg an inch or two below the edge of my panties. I was deeply disappointed with myself for offending Ms Lee with my unsightly fur again so I promptly shaved a large area on the front top portion of both legs so that no hair was visible anywhere near my panties. I sent a new photo to Ms Lee apologizing for my failure. I also assured her that I did indeed want to be her pretty girly boy even though it deeply embarrassed me to say so. I am beginning to feel like quite a sissy, wearing nothing but panties and not allowed to even touch myself without her permission. My embarrassment about being a sissy had recently been reinforced by a comment I had received concerning how I look wearing my panties:

I was shocked when I received a response from Ms Lee informing me that I had addressed the wrong area. She had been referring to the fur that was visible on the outside of my left leg, not on the front. I had aggressively shaved the entirely wrong area for nothing! I could only hope that it amused Ms Lee that I had done so. I then shaved the outsides of both legs and sent her the attached new photo of my well shaved legs.
Shaved again

I was greatly relieved when Ms Lee informed me that she was pleased with the results of my shaving, saying that I looked much nicer. I do try very hard to look pretty for Ms Lee but I still struggle with the embarrassment I feel about being a sissy.

It just occurred to me that I forgot to mention that I had sent the initial photo I mentioned to Ms Lee as I was begging her for permission to touch myself (it had been a week since I had last touched myself). Although she did give me permission once I was properly groomed I realize that I had been much more concerned about offending her with my unsightly fur and making sure that she was pleased with my attempt to correct the situation. Obtaining permission to touch myself was an insignificant matter in comparison, as it should be.