My Extreme Sissy Training Story

How an unknown online Mistress managed to sissy train me

This sissy is writing this as an assignment for my Owner. To explain it to you my Mistress wants me to always refer to myself in the third person. This sissy found it odd at first but sissy training helped me realize the power of spoken language can have in how one sees one’s identity.

Now it is almost the end of May, this year has been crazy. I could never have believed the transformation. This sissy drools and drips in anticipation to tell you about how it lives life now and how it all happened so subtly. This sissy will try to not get ahead of things and take it from the beginning, not so long ago even though it feels like a different life.

Let us start from the beginning. It all started back in.. let me see, I think it was September last year. True but that was only first contact, it was later that this sissy got, you know… Maybe not so easy to explain how this actually happened without taking it step by step, this sissy is still amazed by the change of life it now has.

How my sissy training started

This sissy was an average Male. This male had an eight to five job at a local university. It was a mix of administration, holding classes in computer programming and mathematics, and sometimes assisting in research projects. He shared his life with a lovely and a bit nerdy girl. Their intimacy was amazing but what was lacking was any actual sex. This male was a little submissive, and really wanted more than the vanilla things but could not dare to bring it up. So most days it was cuddling and not much else. Sometimes his girl (whose name is left out due to privacy) even asked if he was a gay. He thought more of a sissy husband but you get the picture.

Dreams do tend to come back and haunt you as they say. This male had for the first time dared to submit a profile online on a BDSM site. Got a few replies. Most of them where a Master or Mistress saying they wanted a slave to submit to them and be controlled, branded, enslaved and locked up in chastity for life. While that did sounds fun, he did find it a bit to extreme. He wanted a Mistress so bad but did not really want to give up the job or the girlfriend. Perhaps the girlfriend could be replaced… there was just something appealing with living in a cage, or in a farm as a livestock animal.

One week he found an answer to his desperation for submission. A Submissive had posted a story talking about a Mistress that turned him into a sissy. Curiosity got the best of him and the story captivated him. He could only read for a small window of time every day to avoid the girlfriend to learn of it. After a week he finished the story and was dripping hot. The story ended and with it a link to a submission form.

He was puzzled looking at the form. This could not be true, could it? He looked at the first page of questions but he dared not to enter anything and closed it down.

It was several weeks later that they broke up. Tensions had grown and while they both were kind and understanding people, they both had to admit they were not perfect together. Being alone and a bit sad despite the rather decent breakup, he went to sex as comfort.

It was first the usual BDSM porn with a Mistress training a male or female slave. Yet, time and time again thoughts drifted back to that sissy femboy story. He found a few JOI videos and a cum eating instruction video (CEI) popped up in the suggested feed. He found the CEI porn interesting, and again memory brought him back to that super hot sissification story.

Then it was as if a world opened itself up. He searched for crossdressing stories and started reading multiple sissy stories and other forced feminization stories. This was the peak of submission as if it was some ultimate fantasy of how far submission can go.

He went to the sissy femboy story he first read and read it again this time from start to finish in one session while jerking. It was just as hot the second time and he had been touching himself all along and his desire was at a peak making normal rational thoughts near impossible. He clicked the link to the form and read the initial legal warning.

This is how the form warning looked like:

Dear male applicant,

This will make you submit to become trained as a sissy. After submitting the form a worker will look at your answers and if you meet the basic requirements you will get an email with instructions. If you decide to follow those instructions then you might end up in a situation where you cannot stop yourself. This is important to understand since The Sissy Academy Processing and Admission Board takes no responsibility for your choices after that point. Some are more susceptible than others and you should not assume you are among those with strong will since you will not know this until too late. Only proceed if you are 100% that you are ready to explore an alternative life, far from what you have now. We can say that since processing is so strict we are proud to say that all trainees are incredibly happy with their life transitions. This process will take time, it will take work, it will be socially tricky to navigate and for some even socially painful due to discrimination in today’s society. If you are homophobic or too sexually restricted to explore your self then leave now. This is for those who want to explore sissification and see if they can take it to the next level. If you proceed far enough in the sissy training you will be assigned a personal Mistress. Please note that this endeavor is nonfinancial, you pay only with your life. Will you ever choose to serve full time instead of staying enslaved to your current job then all your basic needs will be paid for and you will get free training updates to make sure you keep an excellent sissy quality of service and perfectionism in each of your new skills.

Best regards,

Sissy Administrator Sarina Valentina

After accepting the legal stuff the form went into questions regarding sissification and forced feminization. It was a strange mix of worry, embarrassment and submissive hornyness that the male experienced.

It took a while to consider all answers but then it was sent. No response came and the male realized it was not a serious thing. The male continued to explore sissy stories with forced crossdressing and even found a few sissy training videos.

It was the 1st december that an email arrived with the title “How to enter the Sissy Training Program”. It was the sissification form response. In the email, there is a link to download an audio file and some instructions.

“This file will prepare you for the training program. If you choose to be part of the competition then you need to listen to this file exactly once every day. “

“You must make sure you take one whole hour where you find a place and make sure you have no distractions that might disturb you in any way. Phone in airplane mode, computer off, windows and doors closed, and make sure no other people can enter the space you are in.”

“Lie on your back on a bed where you can stretch out your legs and put your hands by your sides. Get a blanket if you need due to temperature. Plug in your headphones and take off all clothes. Start the audio let the instructions follow you into your mind.”

“After each audio pass, you should go directly to your computer and send an email to this address with the title such as [Sissy Pre-training, Monday 1th december, 19:45] with the current time and date. In the email you will write the exact time you will do the training the next day, such as [will start training tomorrow Tuesday at 20:45.”

“Only if you follow all instructions above will you be able to proceed. Each day that you complete the training a mail will arrive 10 minutes before the audio is about to start.”

“You will have a five-minute window to reply to this email. Reply with the time you commit to the next day, download the new audio file and start listening on the bed at exactly the committed time.”

“During the session, you will be awoken and then you need to go to your computer and send an email with the instructions given to you in the audio. You will have a five-minute window for this as well. After this, your session is done and you should not continue listening to that audio file anymore. Instead, go and take a shower while you are still in the calm relaxed state you woke up in.”

“If you miss just one day then you are out .”

“If you fail you may apply next year.”

-Nina Lawless

Can you guess what happened? The first audio was about water. It was a bit odd but felt very relaxing. It felt good as if a submissive dare to subject your own mind to unknown influences. Personally, this sissy did not believe in hypnosis, and that being said hypnosis cannot make you do anything against your will anyway.

As you already know, this little sweet sissy kept it up for and the 20th December the emails stopped and told me I need to stay in chastity until new year, but jerk for five minutes three times a day, in the morning, around lunch and at the evening, and send a mail with time for each and also a number from 1-10 how the sexual frustration level was.

Had the sissy not set up notifications this might not have worked, but thankfully it did. Before new year the desire to get release was unparalleled. A mail arrived that said, “Release time”. The instructions were to get a shot glass and use only two fingers, in a pinch grip, and with almost no pressure quickly move up and down over the head and cum in the glass. The sissy was supposed to do this while on knees and while staring at a wall. It had to be as quick as possible and when ejaculation comes directly release and let it drip by itself down into the glass, then put the glass in the freezer.

30 min later an email arrived from Nina with the title “Last Task to Get Accepted”. It was a task to put forth the now frozen shot glass with cum, hold it upside down and take a picture at the glass plus a table.

Then I got admitted. Since that day I was asked to install an app on my phone.

The phone asked me for my work times and told me to report in the morning and when I arrived home and when going to bed. I did this for a few days and then a new order came.

“Before you eat anything, you must ask for permission. A permission button has been added to your sissy dashboard.”

At first, this was as simple as a touch on “Ask for permission” and then click on “Food” then the app said I was good to eat. I cannot remember the exact details but the following days the app asked me to take a photo of the food I was going to eat as well, and that I had to first ask for permission to prepare the food and then to eat it after taking a picture. Then it also wanted me to ask for permission before I could leave in the morning for work and go to bed in the night.

At the end of the first week of training, it was a Saturday morning if I remember correctly when I woke up by the sissy morning alarm. I reported that I was awake and out of bed. I felt quite tired and looked at the time. It was 5 in the morning. I directly asked for permission to go to bed. This was the first time the app did not approve my request.

I got a bit unsure if I should just ignore it. I did linger on the idea for a moment since I was so tired. It must have woken me up in the deepest sleep, I could barely think and then the app asked me to listen to an audio file and meditate. I did so and a rush of submissiveness flowed over me and it felt so good to be an obedient femboy slut. I have had a lingering feeling of submissiveness lately and it felt more and more right to let myself to be controlled. A little later the app beeped and gave me a sissy shopping mission.

The shopping mission was from a Mistress, Mia Isabella, supreme forced feminization trainer. I gulped as the app played a streaming video of a Mistress clad in some sort of leather outfit. I realized that this was it, I either end it now or I will never know where this will end.

Mia commanded: “On the floor and on your knees when I talk to you.”. I was so shocked but did as I was told and looked at the screen. I thought she could see me like this, in my underwear, tired and then she said: “We are not using video, so you need to tell me when you follow an order or if something stops you from doing so”. I tried to speak clearly but it came out in quite a stuttering way. My lack of confidence was way more obvious that I felt comfortable with and blushed. Mia replied back “Good. Now we will start slow and see what you can take. No sissy has ever left our program unhappy so you are in safe hands.”. I gulped as I considered if she meant this was for life somehow and if I was even willing to take things so far.

Then she spoke again “Today you will do some shopping for next week. Every weekend you will get a new shopping list, it needs to be fulfilled by the Friday at the very latest. If you buy online place all your orders on Sunday before your bedtime. Will you commit to that sissy?”

I gulped and replied, “I will”. Mia said “You refer to yourself as sissy from now on. And when you speak to me you always end with Madame. Each Mistress has her preferred pronoun, you are expected to learn them the first time you hear them, with no exceptions. Make sure you practice after our call so you can avoid punishments this early in your training. All understood sissy boy?”, I replied “Yes Madame”.

Mia continued “I have added a list of things for you to buy, can you see them on your screen?”. I replied, “I can”. Mia sighed and reminded me “From now on you never use the word I, you are a sissy and you refer to yourself in 3rd person always, when you talk and when you write. An acceptable reply would have been *This sissy can see the list, Madame* is that understood”. I felt a fear through my body as if obedience to Mistress Mia was one of the most important things in my life and I replied: “This sissy understands.”. Mia then replied “Good sissy, you will be a cute femboy soon enough. Is there anything on this list that you cannot acquire to next week?”.

I looked at the list:

1 white thong
1 green bikini bottom
2 pair of pink panties
1 pair of black boy short panties

Beauty Tools:
A feminine pink/purple deluxe razor
Feminine pinkish shaving cream
A body lotion that hydrates and nourishes your skin

I hesitated for a moment before I answered “No Madame”

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