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This is documentary.
I have been tasked by my dom to wear a chastity cage for 90 days. Each day I send him a photo of me in my cage with a note saying "Thank You Master."
The purpose of this project is to feminize me. To change me. To rewire my psychology. To humble myself.
Here, I will record my thoughts and reflections. Everything will be 100% truthful. Anything omitted will be what's irrelevant.
Here goes.
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Day 61 -- November 5, 2020
Master of Maids, aka Mike, has a priority for me:
He wants me to have a sissygasm.
What is that? It's when a sissy (like myself) cums without any traditional stimulation to her genitals.
In my case, that means I will still be wearing my cage, plus lingerie. And I'll be using my vibrators... both of which I bought for this purpose.
The new one I bought is hot pink. It's cute. Got this little round ball at the end of it that will fit neatly inside my butt. I rode my bike to the post office to pick it up so I can shove it in my ass later tonight.
I wonder what the sweet post office workers think of me? I'm friends with them, all of them. What would they think if they knew that the package I'm picking up is something designed to go deep inside me, to give a thrill to the man to whom I am willingly enslaved?
Who knows? Maybe they do the same when they go home.
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Later that same day. I'm in the hallway of my house. Good light and total privacy. What I'm about to do should be attempted alone, out of sight of peeping neighbors.
I put on some porn, some really horny porn. A boy gets turned into a girl by his girlfriend. Then, for an hour, he gets fucked. He's not even caged, but he never touches his little penis. Sorry. She never touches her clit.
She gets pounded down in every position possible. I dream of being her, of surrendering to a cock in every way imaginable.
Still, I don't cum. I leak--I leak so much I drip. My caged penis gurgles--I can literally hear it flowing from inside me. It feels SO GOOD... But I can't get to an orgasm.
I feel like a disappointment.
But I tried. I tried really hard.
Lessons learned:
-Douche before you assfuck yourself. Even if you don't think you need it. -Keep your dildo chargers handy. -Keep trying. Even if you don't orgasm, at least you've completely humiliated yourself.
My tormentor was happy for me, though a little disappointed himself.
I want so badly to make him happy.
That's all I want.
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Day 62 -- November 6, 2020
Tried to have a sissygasm again today. Rode my dildo hard. Watched amazing porn. Could not get off still. I am trying. I am learning.
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Day 65 -- November 9, 2020
A sign of how suggestible I have become: I bought a service apron to wear for some photos for one Fetlife user. Apronfetish. Yeah.
Got some shots of me in my beloved kitchen bent over the sink, bejeweled butt plug inside of me.
Apronfetish was very happy and therefore so was I.
Side note: I am writing this now from the future--eight months after this happened. Those apron shots are hot--I look femme.
But my body is very much pre-trans.
More on that later.
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Days 66-74 -- November 10-18, 2020
Boring days. Just a lot of shots of me in panties. Nothing special or really noteworthy.
Except for this: On day 66/67, I passed a marker--that is when I would have had my 100th orgasm... if not for chastity. I have given up, because of my commitment to Mike, my pleasure 100 times. Now many more times than that.
That's based on the math of getting off 1.5x per day, which is just about exactly right. I loved getting off. I did it nearly every day, obviously. As I'm writing this, I'm back at the point when I COULD get off... but I honestly don't really like to anymore. It makes me feel sad. And not like myself.
How did that change so quickly? It used to be so natural. Automatic. Joyful, for the most part. Now when I get my load off, well, it's fun in the moment. Then an hour later I wish I never had.
I think the answer is... that I'm changing.
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Day 75 -- November 19, 2020
I think this is the most feminine day of my life so far. And will be until I start taking estradiol--synthetic estrogen.
I dressed up to do a little service for Master of Maids. He asked for it, of course. I was happy to provide... both for him and for me.
He asked me what chores I love to do. I answered laundry. He asked if I would iron. I said I hate ironing... I really do. I offered to steam clothes instead. He was all in.
So I put on some black lingerie and some tall heels. I turned on some music... really girly and faggy stuff that sounded great to me. George Michael, Britney, Erasure, Peaches. Plus some Nine Inch Nails.
I folded clothes. And I danced.
It felt so natural.
I watch the videos that I shot... part of me thinks I should post them because they are really something. Something so specific.
Something so feminine.
I really was a girl. I have a hard time recognizing the old version of myself in them--I really do.
Here's the strangest thing about being feminine--it is a very subtle change from what you are doing now.
It's in your mannerisms. And your hips and posture. In your eyes, too. It's all over the place.
But it's subtle! To do it right, for ME to do it right, it has to be natural. Not flamboyant. Not queen-like. Just... there.
Feminine.
I'm so proud to see myself that way. I wonder if I can go back to that place. I know I can, but when? Soon, I hope. Soon, I'm planning, in fact.
That I had the chance to reach that level of femininity is so awesome to me. I feel SO LUCKY.
Lucky to be a girl.
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That's a report on Days 61-75. I wish it weren't true, but it is. Drop me a line at sexyamie@hotmail.com if you're turned on.