Sissy Training Facility - Day 03

I was sleeping like a log when a loud bang woke me up. I opened my eyes slightly and saw Mistress Esther hitting the bars of my cell. When she saw that I woke up, she commanded me to get up.

"What the fuck do you think you're doing?" she asked coldly.

I was still half-asleep, so I just stared at her, confused. "Was I supposed to get up early?" I mumbled.

"Don't fucking play with me, you dumb bitch! Do you think I put chastity on you just for show?"

I jumped up. How did Mistress know about me masturbating? The evidence was on the other side of the mattress I was lying on.

"Oh, you're surprised I know about it?" she took out a smartphone and played a recording of me humping the bed. "I know everything, you brainless whore."

I didn't know I was being recorded, so it took me off my guard. I mumbled, "I'm sorry, Mistress," and kneeled before her.

"Well, an apology's not going to cut it for something like that," she said. "This is a place of learning. You are here to be trained in being a perfect sissy slave slut, whose purpose is only to serve men. That's what you signed up for, didn't you?"

"Yes, Mistress," I nodded.

"Then I need to make sure that you won't do that again. If you break the rules again, it's goodbye for you, understood?"

"Yes, Mistress."

I was scared. Not of the punishment that was surely coming, but the possibility of being thrown out of the facility prematurely. This was a one-of-a-kind chance.

"Okay then. I read in your questionnaire that you want to have sex with women here, right?"

"Yes, Mistress."

"Well, if you break the rules, it's only fair I do the same."

Mistress Esther put her high heel leather boot through the bars. "It's one from the back of my closet. Seems to be pretty dusty. Put your mouth to good use, you dumbshit."

She wasn't kidding. There really was dust on the boots. My instinct was to use my hand to clean most of it before going in with my tongue. Before I could do that, she caught my wrist and said, as if to a child, "Your mouth. I said to use your mouth, not your hands. I want someone smart enough to understand my commands."

I forced myself to touch the boot with my tongue. The taste of dust was unbearable, and I instinctively tried to get away from the boot, but Mistress Esther put her arms through the bars and kept my head in place. "It's getting fucking tiring," she said coldly. "Do your fucking job, and don't even try spitting the dust out."

My tongue licked the boots, and the dust started rolling on it. I fought the gag reflex and the want to spit it out and swallowed it. This was a proper punishment, not something arousing in the least. She even wore the highest boots she could find in the closet, probably.

I think it took me about fifteen minutes to lick every inch of Mistress Esther's boots, including the souls.

"Acceptable," she said and let me out of the cage. "But don't think that's the end of it."

I only noticed Mistress had a different outfit on when she dropped her panties. This was something new, as she previously wore a one-piece latex costume, which would not allow doing something like that. Eating pussy? I wouldn't say I wanted to do that at that moment, but I was experienced with it and, in my opinion, pretty good at it. And she did have a really nice pussy, one of the prettiest I've seen with my own eyes.

"It's probably not what you think," she said, looking at me. "You're not gonna eat my pussy. I'm not into sissies. I prefer real men." She turned around. "But I think my asshole is in some urgent need of cleaning. So get to it."

I moved towards her ass and spread the cheeks, afraid of the worst. I did stress that I didn't want any shit play, but it was real punishment. Thankfully, the asshole was clean. "Are you pondering the meaning of life or something? It's not that hard. Get. To. It."

I've never rimmed anyone, ever, but it was one of many first in the last few days. I slightly touched the rim of Mistress's asshole with my tongue. It didn't taste weird. It was very similar to just skin. I guess it was because she cleaned it really well beforehand, but I found the act mindlessly enjoyable. I just swirled my tongue around the rim and enjoyed myself.

And then she farted in my face. "Enjoying yourself too much?" she asked and forced my face between her cheeks with her hands. It was a pretty foul-smelling fart. Mistress probably ate something special to make it so. I gagged a little but decided to try to breathe with my mouth while also still rimming her. "Good slut," she said, and I could hear she was smiling. And then she farted again while still holding my face glued to her asshole. I continued to lick and suck and gag while she said, "This is how a good sissy behaves. She doesn't need instructions to please someone because it's her instinct. Well done." She stopped holding my head, but I still worked my tongue until she moved away from me.

"Your behavior was really impressive, and I appreciate that, but we still have one more punishment to do, this time connected a little more to our training."

Mistress led me to a device that restrained you in a doggy-style position with cuffs around your neck and waist, and something resembling straightjacket parts that restricted the elbows and knees. When she locked me in, I was totally unable to move. As usual, she replaced my buttplug with a bigger one, this time without any teasing. Mistress walked to the front and showed me a gag with a four-inch dildo. "Now we're getting into the real territory," she said. "Remember to breathe through your nose and relax. Gagging is fine at this point, but we get to the place where your mouth will be a fleshlight." She put the dildo in, and it was still on the edge of coming into my throat, but it was very close to.

I felt a hand slapping my ass. It was a firm slap but not really hard. "This is just a warmup," Mistress said, and the second one was definitely with more power behind it. "Who's going to be a good fucktoy?" I tried to mumble "me," but the gag was really making it problematic. "I asked you something," she said and hit me five more times, each one with more power. I mumbled louder, but it was still indecipherable.

"Good enough," she said. Then I heard a sound of a paddle hitting Mistress's hand. "Let's get more serious," she said. "You'll get paddled one hundred times, but I need you to keep the score." For every hit, I tried mumbling the number. At fifty, she came to the front and took out the gag. I gasped for air and wanted to thank her, but before I could, she put a six-inch dildo gag in my mouth. "I think you can manage that, don't you?"

Before I could even protest, she put it in, and I started gagging. "Breathe through your nose and relax," Mistress said. "We have fifty more to go."

I tried her advice, and it did make me gag less. It still happened from time to time, especially after a harder hit, but I managed.

"Well done," Mistress said, taking the gag off. "You're gonna get a lighter punishment for your performance. She put in a ball gag with holes that gave me the option to breathe with my mouth and blindfolded me. "Well, see you in the evening," Mistress smiled. "If you want to piss, don't hold it in. But for the other one... the buttplug can't touch the floor, okay?" I groaned. "Have a nice day."

I quickly realized how uncomfortable the position was and how much I wanted to pee. The latter was easy to fix, and I even felt a rush of arousal when doing that. The former, however, was not a fun experience. The neck cuff was problematic because putting pressure on it was choking me a little. It took me a while to find a good position, and I think I even managed to get an hour or so of sleep.

But I mostly thought about the punishment I went through that day. I didn't want to be thrown out of the facility or let down Mistress Esther. Also, surprisingly, I didn't want to be punished that way ever again. I came here to be humiliated, yes, but not by rimming a woman or swallowing dust. I came here to learn how to be a fucktoy for men and a great sissy.

When Mistress finally came back and released me, I went straight to bed and didn't even think about masturbating. Fucktoys don't do that.