Thursday, November 4, 2021

Assignment From Madam; How I am feeling as the day approaches?

 

My first blog post that will delve into my feelings as Madam Jamie and I are finally nearing the day when my development as her Sissy will actually begin. It’s been over two years since the journey began and I am blessed that Madam Jamie firstly has taken me back but also has had the patience to train me. While we have discussed many things and unfortunately many times my behavior and comments have not been the best,

I am excited by what lies ahead but also there is trepidation.

The trepidation relates to the severe punishment I am going to receive for my disrespectful conduct at our first meeting and then the stupidity of leaving Madam Jamie for another Mistress.

Leaving Madam was one of the most ridiculous things I have ever done.

I realized that I had made a terrible mistake and after a lot of soul searching, I decided to contact Madam Jamie again. I was so relieved when Madam Jamie responded to my messages although the reception was very cold and remained cold for a long time.

Madam’s continuing coldness and overall demeanor still keeps me off balance and I have a hard time dealing with it. I have a hard time being ignored and it makes me feel unwanted.  Every time I want to let Madam know that need her, I get snapped at. I know it’s poor judgement to ask for more attention which only leads to more coldness and a quick written reprimand. Even the written reprimand shocks me a bit which makes me wonder what the verbal one will be like.

Am I afraid? Absolutely, in fact I am terrified. I have been terrified a few times as a submissive but that was at the hands of male dominants. I have this habit of acting up and acting assertive when I am afraid which I keep telling myself not to do especially with Madam because of her no-nonsense character.

I have never shared this before but the other thing that I am so anxious about because it is so embarrassing is that the few times I have been chastised, humiliated to the point of being very afraid or ashamed is that I have actually wet myself like some little boy. If this happened in front of Madam, I would be so mortified.

After a lot of soul searching, I have realized that Madam is what I have been needing my entire life. I have been unreliable, lazy, disrespectful etc. towards women all my life. I have grasped that I need to change, and I am blessed to be taken under Madam’s wing.

All my life I have wanted and needed a strong willed and demanding woman. Someone who will not put up with my lies, games, and disrespect. One thing Sissy’s all have is in their fantasies they have this ideal Madam for most of them it’s more like the dominatrix of their dreams in leather or latex. Not me however I had visions of a business lady who in the real world so her as a successful yet conservative woman. I preferred the idea that my Madam believed in domestic discipline. Someone who would think nothing of slapping my face, washing my mouth out with soap. leading me by the ear, and using whatever was handy to discipline me such as a hairbrush, wooden spoon, her hand etc.

From all indications Madam Jamie is that type of disciplinarian as well as so much more. At the risk of sounding shallow I love that Madam Jamie is full figured and that if she is upset or angry her face shows it. Madam Jamie is a no-nonsense woman who will not put up with any of my attitude. I have needed a woman who could easily overpower me not just physically but also mentally. A woman who just by putting her hands on her hips and staring at me will extract an explanation from me. The fact that Madam does not care if her neighbors hear her smacking my bottom and my cries probably means she would not think of humiliating me in public if the need arose.  Many days I think the humiliation of neighbors or eventually her friends hearing and seeing me being punished would be worse than the physical pain.

Up to this point Madam Jamie has said that she is strict, won’t put up with my habit of talking back or being disrespectful and believes in humiliation and discipline.  I am pretty sure this is the case and she won’t suddenly go soft on me. This would be disappointing because I am going into this wanting to change and be a Sissy, she would be proud of.

I want my Madam to know that in spite of my tears and cries for mercy or compassion I recognize that if you were to give in to my pleading my training would be compromised, and you will not achieve the desired effect.

I love that Madam Jamie has made it very clear that there is no equality in the relationship. I once or twice was upset that she expected me to contact her daily, but she would ignore me for days. When I complained I was put in my place and rightly so.

Every day I think about my first day of training with Madam Jamie. Not knowing what it will be like is so difficult because I do not feel in control. I understand that as Madam’s Sissy I will not have any control and the sooner I resign myself to that the better. This will be a huge hill over me to overcome and a struggle.

I think about arriving and how you act towards me. I doubt it will be in a friendly manner nor should it be. I need to be prepared to confess to you in person about all my prior conduct and lies. It will be very challenging for me to do both emotionally but also the penalties to follow. I will be relieved once it has been dealt with, we will start with a clean slate.

I am very afraid about being humiliated and you making fun of my tiny penis and as silly as it sounds being put into chastity will be horrible. I have never been in chastity before in front of a woman! Madam I have never asked but am I expected to be clean shaven down there too? You have no idea how embarrassing it is going to be to be standing in front of you with my dress pulled up so you can lock me into a chastity cage.

I am grateful that you are open to diapering yet on the other hand I began to realize that it has been at least a decade since I last was diapered by a woman and those times it was with a “mommy” so it was in a nurturing environment. With Madam Jamie diapering can either be as a reward but also as punishment. I expect that because of your demeanor even when done as a reward I will feel humiliated. I can’t even imagine when the day comes that I am diapered, given laxatives and expected to use my diapers. I have only messed once with a mommy, and it was very emotional and draining. To experience it as punishment will definitely have me in tears and I have wondered if the effect will be the same as a severe spanking or worse.

With the help of Maid Jenn, I have been focusing on basics to make a good impression. Simple things like not being late, behaving appropriately and submissively right from the moment that I arrive. I am ashamed to say that I don’t think there ever has been a time where I have not questioned something when the women in my life told me to do something or questioned me about what I have done and why. I know that I really need to learn to remain silent and must never talk back to you.

I am also grateful to Madam Jamie is that for the most part was quite patient when I have one of my online temper tantrums however lately even minor behavioral hiccups upset her and she expresses disappointment and doubt about me. I understand the disappointment as in many ways it’s quite like a mother dealing with an obnoxious child which is another thing I admire about Madam. Decades of not being taken to task will be difficult to undo but Madam will make sure it is undone swiftly and permanently.  I would hope that initially there is some leeway the first time it happens by mistake in person, but I am fearful about how Madam will put an end to any outbursts.

I try to improve because I want Madam to be proud of my accomplishments, I think there are times that she is but when I slip up especially when I ask for attention, she becomes very angry. I hope she realizes that these pleas for attention are because I want to be with her, but she treats them as me being intolerable and a nuisance. I suppose like many things I need to learn I will be taught quickly and definitively by Madam.

While I understand that there is no escaping the punishment, I will receive on my first visit. I know my fate is sealed and no amount of pleading is going to change the outcome. How severe will it be and for how long? I have always hoped that Madam will have a change of heart, but I understand why it must be done. It’s to teach me a lesson but I also think she wants to clearly establish that there will always be consequences to my actions. I still regret my moment of stupidity where I challenged and bet Madam that she could not make me cry in less than 5 minutes. This stupidity sealed my fate and guaranteed my misery.

All my life I have been a pathetic and inadequate lover. Having a ridiculously small cock didn’t help but the real issue my selfishness but also my laziness and lack of desire or caring about pleasing my partner. Chastity will take care of part of the problem and Madam is definitely not going to accept my laziness or lack of effort. My future is now in pleasing Madam not only orally but also with a dildo gag. How fitting that this Sissy will be locked up so that I have no release or even pleasurable sensations in my penis so I will focus my attention on my Madam.  For this reason, I feel that I should remain in chastity until I have mastered the ability to worship Madam’s pussy.

Yes, oral service frightens me for many reasons. One is that I have never enjoyed it, when I did it I did it poorly and without enthusiasm leaving my partner unsatisfied and lastly, I always thought it was demeaning or submissive to have my head between a woman’s legs. How ironic is that because what I truly am is not just a Sissy but also a disrespectful and ungrateful man. Therefore, my place is with my lips and tongue worshiping Madam’s pussy and as Jenn has reminded me, I should always look up at Madam and maintain eye contact so I know my place.

Pussy worship is one of the cornerstones of a Madam/Sissy relationship and it’s non-negotiable. I fear that the first visit I may hesitate or refuse to worship Madam properly out of fear or habit from the past. I know this will be viewed as a sign of disrespect and insubordination and the consequences will be severe either by being forced to worship or punished. Madam, please do what it takes to break me of this disrespectful behavior or phobia.

Once a Sissy told me that he once refused to worship his Madam, so he was punished so severely that after a few minutes he literally fell off his Madam’s lap and immediately crawled up under his Madam’s dress and began worshipping her pussy. It’s safe to say that he learned his lesson.

I know that with training I will be a Sissy who will worship Madam wherever and whenever she desires and make her proud of how she has transformed this high maintenance man into a devoted Sissy

Since I know I am a pathetic and emasculated man my future is having only “sissy sex”, no more penis stimulation and only have my nipples and “sissy pussy” played with like a woman/sissy but also, I will be expected to suck Madam’s dildo. These acts reinforce Madam’s dominance over me as well remind me of my place. I am petrified about sucking Madam’s cock it will be difficult because I am a gagger and there will probably be lots of tears.

Madam’s demeanor and expectations will play the biggest part on my training, but I can’t forget that as her Sissy she owns my pussy too. We have not discussed plugging much or perhaps we have, and I have just forgotten so it’s a bit of an unknown at the moment.  Although Madam may doubt this, I cherish her and am grateful to serve for this reason I think that when she decides to stake her claim on my sissy pussy and enter me with her finger, plug or dildo it will be very significant moment in our relationship.

It probably sounds silly but for me it will be very emotional to have my legs spread like a virgin then lubed up and Madam mounting me missionary style so she can overpower me, see the look in the eyes, kiss me and have me experience what it’s like to be taken.  

All the thoughts I have had so far still leave have not addressed the one issue every Sissy I have corresponded with and learned about their experiences and that is if their Madam will expose them to others. It’s an unknown that will always be at the back of my mind and because it’s unknown it becomes a form of blackmail. As mentioned before even the thought of Madam’s neighbors hearing my punishment and cries is terrifying for me. Since Madam does not care it’s reasonable to assume she would not think twice of embarrassing me or exposing my situation to others in a public setting or even in front of one of her close friends.

I have been blessed to have been selected by Madam Jamie I will never forget how fortunate I am and soon my training will begin.  Thank you, Madam

Respectfully:

Sissy



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