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Living The sissy Chastity Challenge, October Update



Day 129 under Mistress Natasha’s lock and key
 
Dear readers and forum members,
thank you for following my progress into the wonderful, for me still far unknown world to a feminine sissy.
September was not as eventful as the month before, but I still have a lot to report.

The first week I had to pass a punishment by Maitresse Yvette-Louise. The punishment was that I had to wear a bra from morning to night for one week, even while I was working. What had I done? Again and again, I mistakenly wrote Maitresse Yvette-Louise's  name incorrectly. I think Maitresse Yvette-Louise has every right to punish me. I just have to be more careful. Well, my punishment was the good approach that I could gag to wear a bra permanently, which certainly contributes to my feminization.

Then I finally had a vacation that I spent in the mountains. Because I had mastered my first two exams, Mistress Natasha had allowed me to wear no tights during that time. However, Mistress Natasha insisted on meeting my daily corner times. This served to keep Mistress Natasha in my mind and keep me aware of my status as a sissy.
In the middle of my vacation I got a message from Maitresse Yvette-Louise. She explained that I had her settle personal matters in her life and will retire for the time being. She was sorry that it happened because I am in the midst of her challenge. Well of course was and am very sad about it, but have the greatest understanding. Maitresse Yvette-Louise will be watching my progress in the background.

Maitresse Yvette-Louise is a great Superior in every way and deserves all respect. She has fantastic ideas, suggestions and principles and without  Maitresse Yvette-Louise, now represented by Mistress Natasha, I would never have made that challenge. I am so grateful!

Back  from my vacation, relaxed and eager to resume my challenge. Mistress Natasha ordered me to wear double tights until the end of the month and a panty liner in my panties. Mistress Natasha still keeps me chaste in my steel cage. Of course I am very excited and lose "tears of chastity", these are caught by the panty liner.

Then Mistress Natasha decided that my exams should be much more difficult now. My next exam is now in a lingerie store to buy a set consisting of bra, panties, suspenders and stockings. Of course everything has to be matched together. And a matching night dress and a robe I have to buy too.

The fourth exam will be, to make a makeup consultation suitable for my skin type. Well that's the fly in the ointment, so to speak. Unlike in England that costs a lot of money. After consultation with Mistress Natasha, I will now be interested in the Internet for the right makeup.

Last Friday I did my third exam. Mistress Natasha previously demanded that I do my lingerie shopping with shiny painted fingernails. That served as a sissy to my humiliation and to my status. So I painted my fingernails shiny and went to shopping.

I took my courage and entered a lingerie store. At first, I was lookong, how many ladies were in the shop and then asked nicely for the help of a saleswoman. First, she was looking for a female colleague and let me wait two or three minutes, which added to my embarrassment.

Her female colleague was very friendly and asked me first what style and what colour I wanted. She showed me the news and I opted for a very feminine set in apricot. The saleswoman asked me about the size and she chose what I wanted and handed it to me. With all my courage, I asked for a suspender belt. Unfortunately, that did not exist for this set.

Then I wanted to have a matching night dress and a morning robe. Also the friendly service had nothing matching. So I tried to buy a matching nightgown and a robe in another shop. Again I did not find what I liked. Also in a third shop I did not find anything. In every shop I was  politely advised.  In the meantime my shiny fingernails, I had  forgotten total.

I then found someting in the fifth shop. Again a very friendly saleswoman helped me. I then chose a cream-colored cotton blend night dress and a white dressing gown. I had actually imagined something made of satin or jersey, but apparently this is not en vogue.

I will now do my fourth exam on the internet. I'm going to spend a lot of time how to use makeup, which cosmetics are applied where and how, what's over the top and how to wear unremarkable makeup.
 
An exciting time will follow and I cannot wait to see how far I can submit to Mistress Natasha. There is no greater desire than be locked by my Mistress, in my tight inescapable chastity cage and no greater pleasure to submit to her female power and her strictness to turn me into her proper sissy.

Sissy caja
 
For years my wife in a variety of ways has punished and humiliated me in public. I can relate to your lingerie store experience. When we are out and about, she sometime will punish me unexpectedly with what she calls "An Instant Sissy Submission." She will order me to go purchase something feminine. If questioned by a saleswoman, I have to admit that that the purchase is for me because my wife is the boss and wears the pants in our house.

If I am lucky, she just sends me off to make the purchase. More often than not she will further my humiliation by adding one or more of her creative touches that she always has available in her handbag. Like you, I have bought lingerie with painted nails. I also have been sent off with a bow in my hair, wearing lipstick and carrying her purse. Her orders are always obeyed because I know that my disobedience will result is a far more embarrassing punishment for me/
(10-10-2018, 02:19 PM)SheWearsThePants Wrote: [ -> ]For years my wife in a variety of ways has punished and humiliated me in public.  I can relate to your lingerie store experience.  When we are out and about,  she sometime will punish me unexpectedly with what she calls "An Instant Sissy Submission."  She will order me to go purchase something feminine.  If questioned by a saleswoman,  I have to admit that that the purchase is for me because my wife is the boss and wears the pants in our house.  

If I am lucky, she just sends me off to make the purchase.  More often than not she will further my humiliation by adding one or more of her creative touches that she always has available in her handbag.  Like you, I have bought lingerie with painted nails.  I also have been sent off with a bow in my hair, wearing lipstick and carrying her purse.  Her orders are always obeyed because I know that my disobedience will result is a far more embarrassing punishment for me/

Hello SheWearThePants

Thanks for your comments, which are important to me, because it may spring from new ideas and because I feel some response. So I am aware that other forum members are following my progress.

Yes, I would be very happy if in my real life a dominant Mistress would instruct me on embarrassing tasks. The submissive part of being a relationship is wonderful, but it also has a price to amuse the dominant side, feel its dominance whenever it wants to.

I would very much like to live a real life with my online Mistresses, but unfortunately this is not possible, so we live our online relationship as much as possible. I will go through Maitresse Yvette-Louise challenge.

sissy caj