A Career Change

By Rachelle Naughty

Published on Nov 1, 2022

Transgender

This is a work of fiction depicting sexual acts between consenting adults, aged eighteen and over. There are no similarities to anyone real or living, other than myself who is the main character, set in deep running fantasy. There are depictions of unprotected sex and smoking. I do not condone either, as each is an individual's choice. Constructive feedback welcome at rachellenaughty@yahoo.com. Also, support Nifty with a donation if you are able.

A Career Change Chapter 6 -Training Starts Now

Carla knocked on the door five minutes early and entered. She has a universal pass key. I was sitting, awaiting her arrival.

"You need your makeup done," she said.

"I took it off before I went to bed as your note said I should, and I have not had time to practice makeup here. I shaved, douched, showered, and worked on walking in the heels for a half hour. I have been up since seven," I replied.

"Very well, we will do your makeup downstairs. You stayed an extra half hour at Happy Hour last night."

"I did. The lights were green."

"Good job and you entertained six members. Did you enjoy it? Do you want to do it again tonight?"

"I guess so," I said. Did I just say that I thought to myself.

She pulled out her phone and sent a text and said, "Happy Hour again tonight with Rachelle is on. You should have some reservations today."

"Your dirty laundry goes in the hamper in the bathroom, everything from yesterday put in there. The clothes will be returned to you clean. Do you have plug in now?" she asked.

I shook my head no.

"You will wear a plug while you are here, at the salon or anywhere in the building, except for when it needs to come out. Understood?"

"Yes," I replied.

"Pick one out and put it in. I will wait here," she said.

I did as she instructed and came back out.

"Let's your training started," she said.

I walked out wearing thong panties, a skimpy, short, pink bath robe, and two-inch heels. What a sight I must be, I thought. In the salon, we went to the end room with the sliding glass door. She turned the lights on. It was a fuck machine with a bench. On the wall was a rack with assorted sizes of dildo attachments.

"Part of your training is for you to take cock and take it well. We need to loosen up that pussy of yours. Refer to it as your pussy from now on so there is no confusion. Let's start here with this one," she said, taking a dildo from the selection, and attaching it to the machine.

"Take your panties off, pull out the plug, and get on the bench."

I did that and climbed on the machine into a doggy style position.

"We will start out small and slow. Here is the stop button if you feel pain or discomfort. Remember we want this to be gradual," she said.

She strapped my legs and wrists in and lined up the machine and placed the dildo at my pussy and started the machine.

"How does that feel?"

"It's ok," I said.

"I will be back in fifteen minutes to get you and then we train you to walk better in heels. I want to see you master a four-inch heel today!"

The machine went slow and fucked me for the entire time she was out of the room. I had not had that sensation of a cock sliding in and out of my ass for a long time I thought as I laid there. The dildo was small, no wider than the plug I had in. I felt so used and exposed at that moment. Out of the corner of my eye I saw Estelle walk by and she glanced in at me, smiled and kept walking. Carla came back as the machine stopped. The dildo pulled out completely and God, how I love that feeling.

She undid the restraints and told me to dress, and put the plug back in. Estelle was going to do my makeup. I did as I was told and went to the makeup room. Estelle was as efficient as she was the day before. She seemed to take a little more time and I found out why when she turned the chair. Looking at myself in the mirror, I felt more feminine than yesterday. She accentuated my cheekbones and eyes that made me look very sexy or at least I thought I did. She came back with a different wig and set it on my head. Wow I thought, what a difference.

Carla left a pair of four-inch heels for me to wear. I wasn't a stranger to these, having purchased a few pairs an exceedingly long time ago. This pair had locks that locked the shoe around the ankle. A fantasy of mine from years ago was to be locked in these for a day while older men had their way with me. I took the other heels off my feet and put the new ones on. They were tight fitting, Damn my big feet. Why couldn't I be a size six? Estelle locked them in place.

Carla came into the room, "Don't you look like a hottie," she said seeing my face with the dark brunette wig. Estelle handed Carla the keys for the heels.

"Let's get you up and walking sexy thing," she said.

I stood up from the chair which wasn't as easy as I thought it would be.

"Now remember, heel over toe, pick a line and walk it. Take short steps. Come out here." she said as I clumsily followed her. "Start here and walk to the end and back. Try not to look down the entire time."

I started to walk. The heel over toe wasn't the problem, but the heels pinched my feet, and my stride was too long. Carla kept saying "shorter steps, shorter steps". I made it to the end and turned around, which wasn't easy. Carla was watching me the entire time, and that made me nervous.

"When you turn, you want to turn one foot in the direction you are turning and then pivot, like this," as she showed me.

I tried turning again and was slightly better at it. This is going to take time to master these heels.

Carla directed me. "Walk back now."

I walked back, with a shorter stride, losing my balance a few times. When I reached the end, Carla said, to keep at it and she would be back in a half hour. I walked back and forth, trying my best. I was trying to arch my back and stick my ass out to find balance. This was difficult. I admire women who can walk in these. My legs were getting tired as Carla came back.

"You need more work in those. Why don't you wear them today and I will unlock them before I leave? Let's get you back on the machine and you can go up a size. You can go a little bigger."

I took my panties off, and I was strapped back onto the machine. The dildo was pressing against my pussy, and I felt a generous amount of lube being applied.

"Estelle will be in to unstrap you in about thirty minutes, and then I want you to walk in those for an hour. Take a few breaks and learn to just stand in them and place your feet so you are comfortable. Don't just stand there like a typical guy, rotate your hips and legs, and position a hand on a hip, look sexy or at least try to. And don't forget to put your plug back in," Carla said.

The machine was working a little faster than before. This dildo was slightly bigger, and it was filling me up more than the last one did. After a few minutes I could sense that my pussy was getting a workout, and it was starting to stretch me open.

I was strapped into the doggy position and I could not move my legs. My hips started to cramp about fifteen minutes later. I hit the stop button.

Estelle came in, "What wrong?" in her broken English accent, which I adored.

"My legs are cramping."

"I get Ms. Carla," and she left.

Carla came back about five minutes later.

"My legs are cramping from being on here and walking in the heels," I said.

"Leg cramps? We need to get you stretched out and I don't mean your pussy. You need to be flexible for this."

She took the dildo out and removed the restraints.

"Let's change positions and see if you can go for another half hour," she said as she folded the bench down and pulled up the stirrups. "On your back and scoot down so you are hanging over."

Another half hour I thought to myself as I stretched and massaged my legs and then got back on the table, this time on my back. She told me to put my legs up in the stirrups. She adjusted the machine again and I could feel the dildo at my pussy. She started the machine and dildo was inside me.

The half hour went fast, and I was glad it was over. "Walk around for a half hour and then get dressed in the changing room and you are free until five," she said.

I felt like I could cry. My hips were in spasms, my feet hurt, and my pussy was sore. I just want to go back to my apartment for the night, but I agreed to do Happy Hour.

"Don't forget your plug," Carla said.

I took it and reached around to insert it, "Oh its loose, I hope it doesn't slip out," I said.

Carla got a much bigger plug than the one I was previously wearing. I was familiar with the one she brought, having owned the same one several years prior. It was a Doc Johnson Red Boy Large. I lubed it up and placed it on the chair. I lowered myself ever so slowly onto it. The first few inches were not bad, but it was very wide at the base. I had to work it in to my sore pussy. I could feel my pussy expanding every millimeter towards the bottom. Oh my God I thought, this is ripping me apart. When it finally slipped in, I let out a moan.

"As of right now you have three reservations starting at five. Get dressed and room service will have your dinner at seven again so don't stay too late at Happy Hour," she said with wink.

I got dressed in the changing area and was about to go to my apartment to wait for Happy Hour to start and Carla said to wait she had something for me.

"Put your wrists out," she said as she sprayed some perfume on them and on my neck

It was feminine, and sexy I thought. I never thought I would be wearing perfume.

"Have fun," she said.

I left the salon, walking very carefully and deliberately in the four-inch heels. It felt like I was walking in slow motion. I was glad that no one saw me or at least I hoped no one saw me. I was wearing the same thing that I wore the day before except the blouse was pink, not white. I needed a cigarette and went to my apartment to smoke. The clock passed by slowly and finally it was four forty-five. Ok let's do this I said, you wanted this for most of your life. It is now or never.

Next: Chapter 7


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