Sissy Training Facility - Day 01

//AUTHOR'S NOTE: If you're reading this one first, just be aware that there is also chapter called '"Sissy Training Facility"- Day 0' which is basically a setup of the rules of the facility but there's no actual sexual content//

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I was in the lobby of the "Sissy Training Facility" a few minutes before 5PM. I paid rent for my flat, quit my boring corporate job, and told everyone I knew I'm going on a soul searching trip for the next half a year. I also masturbated. A lot. Mostly thinking about this place.

I packed a small suitcase with an eBook reader, a laptop, a few books and other items to keep my entertained. I was surprised by how little I really needed.

"Hello again," said the receptionist. "There's one thing that Natalie forgot to say yesterday. We need a blood test from you to make sure you don't have any STDs. All personnel also has their blood tested every two weeks, just so you know."

She showed the thing that diabetics use to withdraw blood. I gave her my finger and she transferred a blood droplet to a device on her desk. "It's gonna take a few minutes."

I waited, very nervous. I had sex a few times but never with random people, so I doubted I'd have any STDs but it still was a possibility.

"You're clean," the receptionist said, finally, and I breathed the sigh of relief. She showed me the door next to Natalie's office. "Good luck and have a nice time."

I thanked her and went through the door. There was a long hall there, with five doors on each side. In the middle stood a woman. She was a redhead with medium long hair and her skin looked like it hadn't seen the sun in years. She was wearing thigh-high boots and a latex suit without legs, sleeves and cleavage. Her make-up was on point, the lipstick was black which worked perfectly with her paleness.

"Hi. Esther, isn't it?" I asked and extended my hand. "I'm Jake, nice to meet you."

"I don't think so," she said in a matter of fact voice.

"You're not Esther?"

"I am Mistress Esther, not Esther, but that's not what I mean. Jake is a boy's name. Your name is..." she pondered for a minute, "...Jessica, Jess for short. I like it and suits you."

"Yes, Mistress," I mumbled under my breath, embarrassed.

"Louder, bitch."

"Yes, Mistress."

"Better," she smiled and led me to the last room on the left side of the hall. "That's yours."

The door had a whiteboard on it. Things I didn't agree to on the contract were listed there and Mistress Esther wrote my name in huge letters at the top.

"Before we go in: lose the clothes. Throw them on the floor, someone will pick them up."

I reluctantly started undressing. I got an erection which made taking the pants off a little hard. I stood before her completely naked. Mistress examined me for a moment. "I can work with that," she said and opened the door.

The room was quite spacious and full of weird devices, some of them covered and some of them not. There was no window and the walls were black, except for one which was a giant mirror. There were multiple cabinets with glass doors where sex toys were exhibited.

"This is your safe place," she opened a door that led to a small, normal looking room with a couch, a desk and a shelf. "Leave the suitcase here."

I did so and came back to the main room. "And this," she gestured, "is your cell."

Behind the bars was very little space, basically so I could lie there and nothing else. I could see some shackles and a pretty thin mattress inside.

"You'll get there soon, but for now let's start the prep."

She led me to the middle of the room and told me to stand with my legs and arms spread. I complied and she put shackles on my wrists and ankles, and shortened the chain so I could barely move. Mistress Esther then left the room without saying anything.

She came back after what seemed like fifteen minutes, holding a small bag behind her back.

"First of all, a sissy is smooth. There is no place for any hair except on your head." She took out a waxing kit but then looked at my rock hard dick. "Now what to we have here?" Mistress kneeled and opened her mouth. She managed to put half of my cock in her mouth and held it in that position for a few seconds without touching it even a little. Her head backed away and she slapped my dick with her hand. "Were you expecting something else?" she asked. "I hope not. That's not my job and this is definitely not a service you'll get here."

I felt the wax spreading in my nether region. Mistress Esther took a strip and waxed a big area there in one move. It was my first depilation and I winced in pain. My cock shrunk momentarily. "That's more like it," she smiled. It took a few minutes and all of my pubic hair was gone.

When she was done, Mistress took out something but I couldn't see it. It turned out to be a pink cock cage in a very small size which she slipped on me so quickly and so expertly that I barely registered it. Chain with the key disappeared under the latex suit.

"Just so we're clear: you don't have a dick. You have a clit. And your clit is now restrained because no one gives a shit about a sissy's pleasure, including her. Am I understood?"

"Yes, Mistress," my clit tried very hard to escape it's cage.

"Glad we understand each other," she said and continued to wax my whole body, including the face.

"You were pretty brave, you know?" she said after finishing the last strip. "I think you deserve a prize."

The dominatrix took out a black collar with small spikes and two metal rings, one in the front and one in the back. She fastened it from behind and I heard a key turning. "This is your permanent collar. As you can see it has your name tag on it, so everyone knows it without memorizing it." I looked in the mirror and saw a pink heart dog tag with "Jess" on it.

"Now, the last thing. You ever had anal?"

I shook my head.

"That's what I thought," she said and opened the shackles but beforehand put a leash on the ring on the back of my collar. I didn't need to hear any command and dropped on all fours the moment I was free. "Good girl!" she patted me on my head.

In the corner of the room there was a bathtub but it looked different than a normal one. It had restraints in the front and in the back, there was place for feet like it was designed for someone to not touch the bathtub with their back or legs. I also could see that the drain was just a one big hole. The mistress tied me up and even though I didn't have my back against anything it still was pretty comfortable.

"I don't think you need your mouth here," she said while putting in a ball gag and fastening it. "If you need to use a safe word while gagged, do grunt in this way," she presented a very recognizable sound which I mimicked. "Good girl," she patted me on my belly.

"You know what an enema is, right?" Mistress asked while taking a shower head and replacing it with something smaller. I nodded. "Okay, we'll try something more interesting, because so far everything was pretty vanilla, right?"

Mistress lubed me generously and tried to put her finger. It was a very weird sensation but judging by my throbbing clit, a good one. "Looks fine to me, a good virgin pussy," she murmured and lubed a tiny showerhead which she replaced a normal one with. It entered my relaxed asshole and stopped what felt like two inches in. "Now hold it. Hold it hard," she commanded and I obliged.

The water started pouring slowly into me. The feeling was indescribable. The closest comparison I could find was that it kind of felt like weightlessness. My insides were filling with water... Too much water. I thought an enema is like less than a small bottle but it seemed to be few times more than that. I looked in horror at my belly enlarging to the point that I looked a few months pregnant. The spit was leaking out of my gagged mouth like crazy.

"Don't worry," Mistress Esther said. "It's perfectly safe the way I do it. I would never break my toy, especially on the first day."

When I felt stronger pressure inside, she stopped the water leaking into me but left the showerhead inside. After a few minutes of me holding the water inside, Mistress took it out and told me that I have to release all of the water. The uninterrupted stream from my asshole was excruciatingly long and embarrassing. I could barely see the shit that was leaking out of me but the smell made me nauseous.

"Now let's find something to put in your pussy," she said and approached the cabinets. Mistress returned with lube and a glass anal plug, wearing latex gloves. "We're gonna start small, but don't worry, you're gonna take big dicks in your pussy in no time." The plug went into me very easily. "I hope it's already clear to you that you have a clit," she flicked the cage, "which is not to play with, of course. But you also have a pussy," the plug burrowed into me even deeper, "which is to be plugged at all times except for when you're in the toilet. Do you understand?"

I nodded. Mistress took the restraints off and led me to my cell.

"I think that's enough for today," she picked up a bucket lying next to the bars. I think you'll only need to piss, so that'll be enough. But I don't want you to choke on your spit, so I'm taking the gag off."

My owner detached the leash and threw something into the cage. A cupless stretchy bra and crotchless panties, both black. She then took out a measuring tape and did all of my measurements, making diligent notes. "You'll have a whole slut wardrobe custom made for you in a few days, but for now wear those."

I complied and then laid down on the thin mattress.

"See you tomorrow, slave," she smiled.

"Good night, Mistress Esther," I said.

The lights turned off and I was all alone, behind bars, with a caged clit, plugged pussy, wearing sissy lingerie and a collar with my name on it. I never felt better in my whole life. And today was just preparations.