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Living The sissy Chastity Challenge, September Update
#1
Living The sissy Chastity Challenge, September Update


Day 94 in chastity

It's been three months now, since my last orgasm, and around that time I begin to feel the onset of a growing obsession. The obsession is about the basic requirement that you always want what you cannot have. I miss my orgasm so much that it becomes a focal point of my desires. When my obsession gets so strong, it can really hurt to be reminded of what I miss.

I’m definitely would miss, Mistress Natasha's orgasm denial fun so it would be absolutely silly if Mistress Natasha would let me out now. After all, this is why we do what we do: so I can experience these intense feelings and emotions. I can’t help but think that I’m missing out on so much pleasure by not cumming for months on end. I know it ends up worth it once I’m finally allowed to… it’s just hard to be that patiently.

It has happened again this month some things that are new. Mistress Natasha has become even stricter, and I have become even more submissive. I wished but did not believe in how devoted I will be, how much I worship Mistress Natasha and also Maitresse Yvette-Louise. Maitresse Yvette-Louise asks from time to time how the challenge is progressing and how the relationship develops.

My writing assignments takes a long time to complete, my appearance is supervised quite closely by Mistress Natasha. More and more Mistress Natasha demands photo proof that I'm still locked up, or that I wear (DTT) double tights on Tuesdays. This happens through a codeword with which I have to provide the photographic proof. More and more Mistress Natasha demands that I wear double tights on Thursdays too.

My behaviour has also changed to a positive one. August was hot, in every way. Mistress Natasha teased me so much that I almost went insane with lust. Mistress told me so many times what wonderful sex Mistress enjoyed and that she could not understand how to spend so long in chastity. Or how long time has  passed, since I had an orgasm. Mistress knew it very well, but wanted me to say it. Or I have to beg all the time to wear double tights on Tuesdays, Mistress has me ask for it several times and says that I could do it better.

Although this summer produced such warm temperatures, Mistress Natasha wanted to test my obedience. It is generally the case that for everything unpleasant and humiliating I have to plead properly that Mistress Natasha allows me.

Worth mentioning and proud, I would like to announce that I had the honour of choosing the clothing of my Mistresses two more times. On the one hand the clothes for a fetish party, both Maitresse Yvette-Louise and Mistress Natasha were satisfied with my selection. Another time, when I had the honour of choosing Maitresse Yvette-Louise work clothes again, Maitresse Yvette-Louise was not satisfied, I had not done well. But maybe I'll get another chance.

 Then in mid-August came the most drastic measure since at the beginning of the challenge. One morning during one of my corner times, which I have to do twice daily for 15 minutes,  it occurred to me that for every challenge, there would have to be some sort of test to confirm whether the challenge as a whole was passed, or at least every month a test should confirm the progress of my training.

I presented this idea to Mistress Natasha, who initially wanted to coordinate with  Maitresse Yvette-Louise. Now both Mistresses seemed enthusiastic and Maitresse Yvette-Louise, as spiritual owner of the sissy challenge, accepted the idea as an addition to the challenge.

The idea has been modified. There is an exam for each month of challenge now. So 12 exams. The exams for June and July will be caught up with. In December, there is a half-year exam. This is already known and  looks like this.
For the first time in my life I am being sent out in feminine clothing. In order to solve it, I am either late in the evening or very early in the morning, when very few people are on the street, sent to the street or in a park. As a final exam in May, will happen the same, but this time in daylight.

Well, I'm very excited and cannot wait to see what to expect. The first exam is now two weeks back. As Mistress Natasha and Maitresse Yvette-Louise previously assured me, it should be very easy. Nevertheless, I was uncertain, excited and expectant.

The first exam consisted then three parts:

1) I had to paint my toenails in bright pink polish. Mistress Natasha wanted them painted perfectly so I have taken my time in doing them. Photos were required.

2) Also that Friday evening. I had to paint my fingernails in glossy nail varnish, it had to be stay on all weekend. Photos were required.

3) Saturday I had to go shopping and purchase sanitary towels and the following items of makeup. Lipstick, lip gloss, mascara, foundation and blusher.

In a way, I was relieved on one hand, on the other hand, it is a small overcoming with shiny fingernails to buy cosmetic and very specific women typical items. Well, I have to admit, I've made it easy to pay for the items at a self-pay terminal without a cashier.

This weekend is the second exam. I'm writing this from Tuesday evening because it's likely to be harder to write at the weekend. This is related to my second exam. This is described as follows:

From Friday evening to Sunday evening I have to wear long, false fingernails. This will make me realize how easy things get the harder on long fingernails. I have to be careful not to break nails or get punished, not to mention that I will not pass the exam.

I have to buy false nails and glue them on. Well, Mistress would prefer that I do this in a shop, Mistress would allow me to buy online if I so wished, but I would need Mistress's permission to do so. But I can choose the colour.
For a few days I am proud to wear a pendant on my neck, the following is engraved: "My name is sissy caja and I on owned by Mistress Natasha". For me a  sign of my submission, my status and my sincerity and respect for my Mistress Natasha. 

Later in the week, it happened again that I accidentally misspelled Maitresse Yvette-Louise's name in a email to Mistress Natasha. Although I urged Mistress Natasha not to report this to Maitresse Yvette-Louise, because Maitresse Yvette-Louise previously announced that if that happens I will be locked up during the whole year of the challenge.
Well, Maitresse Yvette-Louise offered to choose a suitable punishment for me.

Since Mistress Natasha lets me wear a bra under my work clothes once a month, my suggestion went in that direction. I offered Maitresse Yvette-Louise to wear a bra all day on Thursdays, also to work, and every Thursday evening a spanking with the wooden spoon.

Maitresse Yvette-Louise will like to decide soon and tell me.

Well, Maitresse Yvette-Louise has decided in the meantime. I will wear a bra every day from morning to evening until my vacation on the 9th of September and to my humiliation I will also wear daily panty liners because, the Mistresses mean, I cannot control my lust and stain my panties, and that does not belong to a sissy.

next update at October
 
 
 
sissy caja
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#2
No doubt it's far from easy for you, sissy caja. But then, that's the point, isn't it? You appear to be doing well, all things considered. Hope you can keep up the good work and also let us know how you are progressing.
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#3
Very nice update sissy caja...thank you for sharing it, and as always, thank you Mistress Natasha and Maitresse Yvette-Louise for permitting Your sissy to share her experiences.

Certainly the long-term chastity is difficult and challenging, but sacrificing your own selfish pleasure for the amusement of your Superiors provides greater satisfaction for all concerned than the momentary pleasure of an orgasm...your Superiors have granted you the gift of chastity!

Good luck as you continue in your challenge and training!

sissy jamieanne
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#4
(09-03-2018, 10:04 AM)sissyjamieanne Wrote: Very nice update sissy caja...thank you for sharing it, and as always, thank you Mistress Natasha and Maitresse Yvette-Louise for permitting Your sissy to share her experiences.

Certainly the long-term chastity is difficult and challenging, but sacrificing your own selfish pleasure for the amusement of your Superiors provides greater satisfaction for all concerned than the momentary pleasure of an orgasm...your Superiors have granted you the gift of chastity!

Good luck as you continue in your challenge and training!

sissy jamieanne

Thank you so much for your words.  For sure the pleasure of the Mistresses is always on first place, even if I had to endure long term chastity. It is only the Mistresses to decide if, how and what kind of pleasure I should earn or even not. And 
well, the Mistresses knows how to correct little bitches like me…
sissy caja
sissy caja
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#5
(09-03-2018, 04:35 PM)Yvette-Louise Wrote: Well Miss Natasha is in charge of the training of sissy caja, I am taking a very keen interest in her progress.
I must say that both Natasha and myself are pleased with how the training is going and also how keen caja is to develop as a sissy.
I really do hope with support from Natasha that sissy caja will have the courage to venture outdoors during the challenge. If that does happen then there will be two very proud Mistresses and one very brave sissy.

I thank you so very much, Maitresse Yvette-Louise for you kind words and of course very grateful to Mistress Natasha, both of you teach me respect, obedience, behaviour and submission as a sissy. I am sure I will follow the rules of the challenge and I'll have the guts to go outside as sissy when the time is right and then the Mistresses demand it. I will do anything to make the Mistresses proud of her work.

curtsey sissy caja
sissy caja
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