Archive for the ‘Sissy’ Category

Another break

August 4, 2016

It has been over three months since my last posting and I must apologize to Ms Lee and my readers for neglecting this blog. As will occasionally happen in my overly busy life I was unable to keep up with all the demands that were put upon me and had to work myself ragged just to make sure nothing critical fell apart. It finally looks like I am getting a handle on everything but you never know what might happen next.

I have to thank Ms Lee with all my heart for being so understanding during this period (as well as previous ones). She has generously allowed me time to deal with my issues and gave me a chance to catch up with everything. I don’t know how I could have managed without her support. However I feel guilty for not keeping up with my blog as well as other expectations I should have been more responsible about. All I can do is try harder to meet my responsibilities and hope that Ms Lee will forgive me.

Back in June Ms Lee also generously told me that I would be allowed to masturbate freely once a month on a day of my choosing. She also has not required me to wear my chastity sleeve on a daily basis. This has really helped to reduce my stress levels but I am well aware that I cannot expect this excessive level of freedom to continue forever.

A couple of weeks ago I decided to take advantage of Ms Lee’s generous offer for the month of July. I had held out as long as I could and I was incredibly horny and frustrated by then. I had begun to frequently find myself thinking about my purple babydoll nightie that I keep in the back of my closet. When I purchased it Ms Lee told me that I should wear it every time I was allowed a release. I told Ms Lee I wanted to wear my babydoll nightie when I released and I also asked her if I could plug myself with my anal plug. I wanted to try to stretch out my enjoyment and try to avoid coming in less than a minutes as I all too frequently do. Ms Lee was generous once again and gave me permission to do so.

Once I was properly plugged and dressed in my babydoll nightie I began stroking my penis. I was rock hard in no time and worried that I might release all too soon as usual. So I slowed down and tried to control myself. Before long I found myself thinking about serving Ms Lee as her formal butler. I long ago ceased having normal male masturbation fantasies. Mine now revolve around my pretty lingerie and serving Ms Lee. For some reason the idea of serving Ms Lee as a formal English butler gives me an incredible submissive rush. I used to fantasize about serving Ms Lee as a sissy french maid but she made it clear that she preferred to be served by an English butler. She does not cater to my pigmale fantasies and I have dedicated myself to learning how to be the best possible English butler so that I can properly please and serve Ms Lee.

But I digress. As I thought about serving as an English Butler I stopped stroking myself and began moving my plug in and out of my greedy rear. I would pull it almost all of the way out and then ram it all the way in. I continued in this fashion until I could no longer keep my hands off Ms Lee’s property. I began stroking myself again but stopped every time I came too close to releasing. I actually managed to stretch out my play time to a full 15 minutes, far longer than I have managed in years. I’m not quite sure what to make of that, but it was quite enjoyable.

I released quite a large load which I then dutifully licked up. I then put everything away, thankful that Ms Lee is so understanding and generous. Sometimes I forget how fortunate I am to be Ms Lee’s property.

 

My role in the pleasure of Ms Lee

April 16, 2016

Since she has taken me as her property I have been faithfully devoted to the pleasure of Ms Lee. I always keep my focus on pleasing her and satisfying her desires in any way I can. However recently I have been adjusting to the reality that Ms Lee has multiple lovers and submissives who pleases her sexually. As a result I have been struggling to understand how best I can please her – what role do I play, how do I best enhance her pleasure and satisfaction?

Ms Lee has made it clear that regardless of her other relationships she intends to keep me as her property and that my primary role will be to serve as her butler. This had also disturbed me as I discussed previously because I have had fantasies of serving as Ms Lee’s sissy maid. But Ms Lee does not pander to my pigmale fantasies and I now understand that dressing and acting as a sissy maid would only distract me from my primary purpose which is to please Ms Lee. I have now embraced the idea of being Ms Lee’s full time, live-in butler which is how I can best achieve my destiny as a service oriented submissive devoted to the pleasure of Ms Lee.

It is apparent that Ms Lee has a voracious appetite for pleasure, more than any one man could possibly satisfy. As a sexually hungry woman she has multiple men in her life. In addition to other lovers and boyfriends she has recently taken on a very talented lover who sexually pleases her perhaps better than any other man before. Naturally there is a role for real men to please her sexually. But it is clear that Ms Lee also has a need to own a male servant in every way – heart, mind and body. My goal and destiny is to be her devoted male servant. My heart is devoted to her pleasure in every way, happily sacrificing my own pleasure in order to enhance hers. My mind is devoted to learning the skills necessary to serve her properly and constantly thinking of ways to please and satisfy her. And my body is devoted to her pleasure also. Every day I wear my tight chastity sleeve which severely restricts any attempts to enjoy an erection. I also wear panties on a daily basis, which torments me with a mix of embarrassment and teasing frustration. And when it suits Ms Lee’s whim I may be required to wear my anal plug or subjected to physical punishment if warranted. I am thankful that she has given me the opportunity to be her male servant, devoted solely to her pleasure and nothing else.

While I am thrilled that Ms Lee is enjoying fantastic sex with her lover I have been wondering what role I might play in sexually pleasing and satisfying her. Of course when it comes to sexually pleasing Ms Lee there has never been any doubt that my own inadequate penis would be incapable of properly pleasing her. That is assuming I was attempting to sexually please her like a real man. Instead perhaps it is more appropriate that my penis pleases her in the only manner it is capable of – by remaining in faithful chastity, frustrated and forbidden to enjoy the sexual pleasure a real man enjoys at will. I am thrilled that in this unique way my penis can contribute to the pleasure of Ms Lee. While she obviously enjoys being pleasured sexually by real men, allowing them and their superior cocks to enjoy sex with her,  it is also clear that she appreciates having a male’s penis under her firm control, denied and frustrated while she freely enjoys all the sexual pleasure she deserves. I understand that it pleases Ms Lee to have my male sex suppressed or perhaps completely eradicated and I embrace this as my destiny since my only desire is to please her.

While my penis will probably play no role in pleasing Ms Lee (other than remaining in faithful chastity) there may be other ways I can sexually please Ms Lee. Perhaps rimming her is a role I could fill, assuming that she is not fully satisfied in that way by her lover or other real men. I would relish being the one who was devoted to pleasing her in that manner. It is also quite possible that occasionally it might please Ms Lee to have me orally please her pussy. I suspect she would enjoy experiencing multiple orgasms while I was firmly chastised, my frustration driving me to pleasure her to the utmost of my ability.

 I would also hope that Ms Lee would allow me to frequently pleasure and worship her lovely feet. Making love to her feet is another appropriate role that I could fulfill. I would hope that after treating Ms Lee to a professional quality foot massage and pedicure that on occasion she might allow me to worship her lovely feet as my reward for excellent service. Of course I am clear that such a privilege would only be an occasional reward granted if it suits her whim, I am certainly not automatically entitled to anything, no matter how hard I toil for her pleasure.

Since Ms Lee’s pleasure is my primary goal and purpose I am appropriately thrilled that she is being sexually pleasured by the real men in her life. Recently she informed me that she spent the day of my birthday being sexually pleasured and f**ked by her skillful lover. I have to admit that hearing that overwhelmed me with waves of submissive feelings – I was happy she was being pleasured and I was frustrated that I remained in faithful chastity while she and her lover were enjoying the sexual pleasure I willingly forego in order to please her. I told her that I sincerely hoped her pleasure was enhanced knowing that while she was being f**ked I was in chastity to suit her whim. I also told her that I hoped her lover’s pleasure was enhanced as he appreciated her new haircut which I had paid for (she looks so beautiful with her new hair style!).  It occurs to me that I should do whatever I can to enhance her lover’s pleasure when he is with her – because that in turn will enhance her pleasure.

I am sure I will continue to struggle as I adapt to the reality that Ms Lee is being well pleasured, both sexually and emotionally, by her lover and other real men. I am grateful that she desires to keep me as her property and I know all will be well as long as I continue to focus on nothing but her pleasure, avoiding the distractions that worrying about myself would cause.

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:
requesting-feedback-regarding-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.