Sissy Training Facility - Day 00

I entered the skyscraper excited, but also very scared. It all sounded like a scam but I was so entranced by the idea that I couldn't get it out of my mind.

The building looked pretty legit, it wasn't in some seedy part of Chicago, or something like that. I checked the leaflet to make sure that the floor was really "69", and that's what was written on it. I walked into the elevator and pressed the correct button.

I had found the leaflet lying around a table of a department store I'd visited. The design was very simple, and was on a paper from a home printer. You could say it was designed to be unassuming.

It said, in big letters "Sissy Training Facility" and then in smaller print "Are you a guy? Have you ever fantasized about having your mouth and asshole destroyed by big cock while looking like a gorgeous girl? You're in luck. We will make you a perfect, obedient cumslut ready to pleasure any cock, at any time, while looking like a high-end pornstar/supermodel (whichever you prefer). All of this in six months, just for a downpayment of 5000$."

My dick hardened with every word I read and I hid the leaflet in my pocket without even thinking.

When I came back home, I looked up the address. It seemed like a normal corporate skyscraper in Chicago but there was nothing about any "sissification" on its page and nothing about such an establishment in my city. At least I couldn't find it using my means.

After a few days I had known that I could never find peace if I didn't check it out. I had some savings in cash, I withdrew some more and at about 5 PM, I parked near the skyscraper.

The sound of the elevator stopping woke me up from my thoughts and with a little hesitation I walked out of it to a normal-looking lobby with a smiling receptionist, wearing a pantsuit.

"What can I do for you?" she asked and looked at me with mild interest.

I was to scared to say anything, so I just took out the leaflet and put it on the counter. She looked at it and then at me.

"Don't worry, you're in the right place," she smiled and then pressed a button on her desk. "You're in luck, she's free," she pointed to the door on the left. "Go in there. And don't be so nervous!"

Her encouragement didn't really help and I opened the door visibly shivering.

The office was quite spacious and still normal looking but the woman sitting at the desk was far from it. She was wearing a black leather corset an I could see her thigh-high boots under the table. Her rack was big, probably even more when not restrained by a corset. She had a very strong make-up, and her hair was black and quite long.

"Come in and sit down," she gestured to the chair opposite her. I considered for a second but the curiosity got the better of me.

"Welcome to 'Sissy Training Facility.' My name is Natalie, are you interested in becoming a perfect sissy?" she asked as if it wasn't totally absurd.

"If I wasn't, I wouldn't be here right now," I murmured, embarrassed.

"Fair point," she smiled. "You have to understand that it is neither a joke, nor an understatement. After six months of training with us you will be a perfect sissy cumslut and will experience the pleasure that you could never even begin to imagine right now. Are you really interested?"

I thought for a few seconds. There was no other answer.

"Yes, I would," I said and dick hardened a little.

"Fantastic!" she sighed with relief. "We just have a free spot. But before everything, I need to bore you with some details about how things are done here.

"You are to spend six months in this building. You will not go out, unless it's for something from the advanced sessions, but we'll cross that bridge when we get there. You can keep in contact with people but only through text messages, no talking. Does any of your close family or friends have birthdays in the next six months?"

I shook my head. I didn't really have that many friends or family.

"Good," she said. "You can bring your electronic devices, or any other items. There will be a room devoted to them.

"Now I need to ask you a few questions. What is your sexuality?"

"Bisexual," I said but wasn't really sure.

"You want to be fucked here by mostly men or mostly women?"

"By men," I murmured and blushed.

"Speak up, honey," she said in a commanding voice. "But don't worry, we'll get all of this shame out of you in no time and make you the cumslut you really want to be.

"You are man? You are not a trans woman, that's what I mean."

I was pretty sure that I wasn't but there was a small chance that maybe I was.

"I think so."

"I'm saying that because we will not offer transition here. No hormones, no surgery, so if you want to transition, this is not a place that does that. Of course, you might change your mind and in that case I think some things here would make you better prepared for transition."

"Okay, I understand. I don't want to transition."

"Good, and you even said that in a normal voice. You're already learning.

"To be honest, your face is already a little feminine, the hair should be pretty long after half a year and your build is also appropriate. You have great predispositions."

I didn't know whether to thank her or not, so I just sat silent.

"Now, do you want a Master or a Mistress? That's the person who trains you in here. It doesn't necessarily mean fucking you. You're supposed to serve that person and be their property which they can give out to anyone they want to."

"I want a mistress," I said after a while. "But I don't really want to have sex with her."

"That's fine. Any preferences?"

"Pale skin and a redhead if it's possible."

"Sounds like Mistress Esther. A good choice. Masters are usually worse at feminizing and she is one of the best Mistresses.

"Now I'm gonna give you a very extensive list. Take a look at it and cross out things that you wouldn't want to do. There is nothing illegal here, just so you know. And there is a space at the top. It's for a safe word. You might think it's unnecessary but it really isn't."

I took a look at the list. My dick hardened more and even a little of precum came out. Almost all of them made horny. I only crossed out a few things, including shit play. Never got the appeal. The safe word was a hard one. I finally wrote "Bombadil" who was my favourite "Lord of the Rings" character. Natalie took the list I put on the desk and looked through it.

"Fantastic, that's very good," she grinned. "The less you cross out, the less you pay. And in that case..." she examined the list thoroughly, "...you are elligible for a 100% discount!"

"Excuse me?!" If I had something in my hands, I would have dropped it.

"You see, I am in employ of a extremely kinky and an even richer man. He himself is a sissy in his free time but always wanted something like this. So he gives us a few million a year to train sissies. Five at a time, all year 'round. The money in the leaflet is to make sure you're serious and the method of recruitment is so shady because there are so few spots. This way, men who get here are the most desperate to become sissies."

There was an uncomfortable silence.

"Well, use the money for the rent for the next half a year or something, and we'll see each other tomorrow at 5PM. Don't be late. And don't forget to pack what you need here. But no clothes, please. We'll take care of those."

I thanked her, and went to the door. When my hand was on the handle, she said to me, "One last thing. Very important. Masturbate." I looked at her quizzingly.

"Why?"

"Because it's the last time you will get jerk off like a man in six months," she said with a smile.

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//AUTHOR'S NOTE: It's my first pornfic and English is not my native language (sorry for the typos in advance) but I hope it was an enjoyable read. It was a great experience and I definitely want more of it.

I want this series to have a format of days, where things escalate between every chapter. At first, they will be pretty close to one another but further into the sissification, there will be longer gaps between days. First few chapters will be mostly feminization, toy play and preparations but, in time, it's going to get very filthy and hardcore.