Sissy Training Facility - Day 02

//Author's Note// Hopefully, from this chapter on, there will be much fewer typos and grammar errors. Thanks everyone for reading, rating and commenting on the last two chapters.

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I woke up quite early, or at least I assumed so because there were no clocks or windows in the room to confirm it. The morning wood was pushing the chastity to the extreme it could go. I still couldn't believe my co... my clit could fit in there at all. I had a habit of jerking off the morning wood, but this was not the option now, so I just poked and prodded the cage and slid my fingers on the smooth skin around it.

"What do you think you're doing?" I heard a voice next to me and made me jump. "I hope it's not what I think," Mistress Esther raised an eyebrow.

I quickly composed myself, got up from the mattress, and kneeled obediently.

"That's more like it," she said, nodding. "Ready for more sissy training?"

"Yes, Mistress."

"Great," she smiled while unlocking the cage. "We have more basics to cover, I'm afraid, because you are in no way presentable at this moment." Mistress took my leash, and I followed her on all fours to a dressing table in a corner. "We need to make you look like a proper slut, and every good slut uses makeup as a weapon. Today, I'm gonna do yours, but in a few weeks, I expect you to be a fucking makeup artist. Or the punishment will be severe. Am I understood?"

"Yes, Mistress."

"Let's get to work."

She sat me on the stool and took out many items I could not identify if my life depended on it. I had never been really interested in makeup before, but this was the moment I changed my mind.

First, she washed my face, used a tonic, moisturizer, and lip balm. "You might think this is not important," her hands were rubbing moisturizer into my face, "but skincare is crucial for this. It's like painting with a clear white canvas instead of a dirty and gray one."

Then, she took out a brush and applied a white and pearly substance. "This is a primer. You start with it to prepare the skin for foundation." The brush was tickling me a little, but I tried not to move too much. My face became very shiny and sparkly.

"Now it's time for foundation," Mistress took out a tube and put the content on another brush. "You have to cover your whole face in it, but you have to watch out, so it's not laid on too thick. It makes you look really fake." I saw myself transform before my eyes. Even without the other things on the table, the way I looked changed drastically. "I chose a slightly lighter tone than yours because I felt you like pale skin." She was right.

Mistress picked up something called "concealer." She put it around my eyes, on my eyelids, and in places where I had some blemishes. "I know what it does," I said to her. "Great," she said, "you have some brains. But I don't think you really need them. Just do what I say."

"Yes, Mistress," I said and hung my head.

"This was the easy part, time for things that require more finesse. I think we'll start with the eyes." She took out a palette of a few dozen colorful squares. "These are eyeshadows. In the drawer, there's every color under the sun, so you can experiment all you want. But I think that for the first time, we'll go with gray and silver. Unfortunately, you have something called hooded eyes, which is not ideal. It means some skin above your eyelids is hidden when you open your eyes. The workaround is to apply a lighter tone, in this case, silver, on the eyelid and a darker one, here it's gray, above it. And you really have to blend it in. That's crucial."

"We're going to go for a winged eyeliner," she took out something which looked like a felt-tip pen. "Don't fucking move or blink because this will not end well for you. Understood?"

"Yes, Mistress."

Mistress Esther made perfect four lines, which met in the corners of my eyes to create slim but quite long wings. Then she took out something which looked like a torture device. "You curl your eyelashes with it, don't look so scared," she snorted. The feeling of curled eyelashes was weird. "Now you just need mascara, and we're done." My lashes were covered in black as I looked at my eyes and couldn't believe I could look so hot.

"Lips are easy. It's good to use a lip pencil on the edges and then go in with lipgloss or lipstick. Today I think cherry would be a great look." She was right. I was transformed into a gorgeous sissy.

"We're not done yet," Mistress took out another palette. Here we have a blusher for your cheeks, a highlighter, and a bronzer to shape your face a little." She showed me where to put which to change the shape of some masculine features, including Adam's apple. I thought I looked very feminine without these, but when Mistress Esther was really done, I was dumbstruck. I looked perfect.

"Just one more thing," she said and took out something from a cabinet nearby. After a hairnet, a black curly medium-length wig was put on my head and completed the picture. No one would recognize me on the street like that.

"I hope you were paying attention, but we'll see that later. Now it's time for more... practical training. Are you ready?"

"Yes, Mistress," I couldn't contain my excitement.

After an enema and changing the buttplug for a bigger one, she looked around and picked up a few things from the shelves. Mistress led me on the leash to an empty space on the wall and attached a pretty small-looking dildo to it. "I'm gonna teach you how to suck a cock properly. The men here are experience, and I don't want them to offend them with a teenage virgin first-time level of cocksucking expertise. Are we clear?" she asked, and I nodded, but my disappointment was still visible. "What do you think this fucking is," Mistress raised her voice, "a fucking picnic!? This is a training facility, and you knew it from the moment you read the flier. Now get on your knees in front of the dildo and listen to what I'm fucking saying."

"Yes, Mistress. I'm sorry," I said and complied with her command.

"First thing is getting the dick hard, but we can't really do it with this. Just be creative, lick and suck until it's a rock. Then, you have to spit on the shaft. Lubrication is key." I spat on the dildo. "Good. Now take the head into your mouth." I put it in. "Now that's a quick and obedient slut fit to be here. The frenum, the thing that connects the foreskin to the head, is one of the most sensitive places, so remember about it." I know that, I thought to myself but said nothing.

"You seem to work it just fine. Remember to really suck it. The suction is key to a good bj. Let's go deeper now," Mistress said. "Get in there. You don't have to go for a deepthroat but give it some motion." I started moving my head back and forth and going deeper and deeper. When I felt the gag reflex, I went back to the head and repeated it for about half a minute. "Why did you stop?" she asked. "I'm going to start a timer. You are going to do what you just did for two minutes without stopping. Ready? Go!"

I was surprised by how nice this was. I didn't have any problems with keeping up, and the motion was really calming. "Stop," Misstress said, and I went back to the head and sucked it a little more. "Not bad. I could almost believe that you're a seasoned slut who sucked the whole baseball team."

She picked up one more thing and said. "Let's go for deepthroat. Just swallow the whole dildo and stay that way for half a minute." I spat on the shaft and went all-in in one go. After a few moments, I started gagging, and I held it in for about twenty seconds. "Not perfect, but in a few weeks or even days, you'll be perfect at it." Mistress Esther took out a gag. From one side, it looked like a usual ball gag I'd used before, but on the other it had a two-inch dildo. "That's the smallest one. We'll get to six inches in no time."

"Yes, Mistress." The gag was on my tongue but didn't get into my throat. Still, it made me breathe through my nose and accustomed me to something in my mouth.

"Now it's time to give your pussy some attention," she gestured towards a smooth surface with restraints screwed into it. I laid down on it, and restraints were closed on my waist, neck, and arms. Then, Mistress took my legs and put them in shackles hanging from the ceiling. In this way, my pussy was very accessible.

I felt the buttplug leaving my body. Not quickly and smoothly but slowly and teasingly. Then I heard the sound of lube pouring out the bottle, and something bigger started stretching my asshole. I tried groaning but instead gagged a little. "You like that, slut, don't you?" I groaned happily. "Bad for you that I don't give a shit about that." The dildo went deep into me in one smooth motion. "I have to get some coffee. Don't go anywhere, and if I see that dildo on the floor, you won't be able to sit for a week." I tried to groan "Yes, Misstress."

She closed the door behind her, and I was lying and waiting for her. The dildo was held only by my pussy, and it started slipping a little. I really had to clench because I didn't want to disappoint my Misstress. I didn't know how much I waited, but she finally came back. "It's half out. Not terrible, but we need to train this pussy of yours more." She took a sip of coffee and started to slowly move the dildo in and out. This was a hand of an expert because it was always on the edge of being pleasurable to me. It was a very frustrating experience, and I believed that she only wanted to stretch my pussy, not get me off.

"I think we're done for today," she said and took out the dildo, put a larger buttplug in, and started to release me. "You have the rest of the day off. Do whatever you want but remember to do your exercises focusing on stretching, use makeup remover and do a skincare routine."

"Yes, Mistress," I said when she removed the gag.

I spent the rest of the day in my safe room, surfing the net and training a little more on the dildo she left on the wall. When the night came, I closed myself in my cage and prepared to go to sleep. But I have to say, back then, I masturbated daily and my first day in Sissy Training Facility was without jerking off. I felt compelled to do that, but the chastity cage was so tight it was impossible.

After some trials and errors, I found a way. When I was hard, humping the mattress in a specific way worked amazingly. After a few minutes of doing that while toying with my buttplug, I managed to cum and was surprised how much better this way was. I didn't know what to do with the cum, so I just turned the mattress over and went to sleep happily. There was no way that Misstress Esther would notice something on the other side of my bed. Right?