A Sissy Promotion Pt. 02

I felt weird as I sat in the new minivan that was to be my company car. For one thing I was wearing a dress but it was the diaper, the wet diaper that made me self conscious. Sitting in it was both humiliating and erotic. But I couldn't get hard.

I drove to the rather nice house the company used to train house maids. I had never been inside before but from the outside it was pretty nice and in a good part of town. And it had a garage so I was able to get inside without being seen which was a relief.

Inside the house was pretty normal although much bigger and nicer than any house I had ever lived it. One weird thing was all the signs. They were everywhere, signs like "Remember to wiggle your ass when you sweep and mop." and "Cleaning while on your knees makes all the difference."

These signs were all over the hose. I guess training the maids was far more in depth than I had imagined. No wonder all the maids were hot.

My cell phone rang, it was Lisa.

"Hello," I answered.

"You were supposed to call when you got home sweetie. I bet your going crazy about that cage on your little dicky huh?" she said sarcastically.

Actually I hadn't really given it a thought but now I was concerned so I said, "Yeah, a little. How do I get it off?"

"It's real simple sweet pea, you need to make a deal with me." she said.

"Okay, what kind of deal? It can't be any weirder than the deal I just made with my boss to pretend to be a diaper wearing trans woman for a promotion." I said knowing I was probably wrong.

"Well here's the thing. I hate you. First, your a guy and guys are all dicks so it's a thrill to see you in a dress and a cute diaper. Second, I'm quite jealous because you got a free house and a company car not to mention an expense account and a raise. Third I have a well, let's call it a fetish for sissies." she began to explain.

"So you want me to fail and get fired?" I asked.

"Not at all, I want you to succeed, emphasis on Suck. I want to make you the sissiest little slut possible. Of course I would have to live in that big house with you and share in that expense account. That is if you want the key to release your rather small dicklet." she finished.

"So, you want to live with me as my girlfriend and help me learn to be girly at work or is this something more?" I asked a bit confused.

"Girlfriend? lets not get ahead of ourselves. Pretend to be your girlfriend just like your pretending to be a girl. My role would be more of a huh... what's the word? Mistress, that's it, I will be your mistress. Or if you prefer, you're babysitter seeing as you will need someone to change your wet diaper." she explained.

"Does Mr Miller know about this? I asked worried but somehow also excited.

"Who do you think put the idea of a trands diaper sissy in his head and then suggested you for the role? I just knew you would agree to his little proposal to help save his company. No real man would have made the deal you made so I am guessing you're actually excited by the idea of becoming my sissy. Tell the truth?" she demanded.

I was actually slightly excited by the dress and the wet diaper and wanted to jack off in the worst way but I had never thought of being a womans sissy. "Some of it is a little exciting, I mean the dress and all but you want me to be your sissy? I dunno." I said knowing it did somehow excite me so I added, "It would only be in private right?"

"Sure, in private. Just until you agree to more. Now, turn around and face the flat screen and turn it on." she instructed.

I turned the T. V. on and saw Lisa sitting at her desk at reception.

"This is a training house," she began, and then continued "and as such has cameras everywhere. Take the dildo out of your purse and put it in your mouth and I will tell you where the key to your chastity cage is." she instructed.

I got my purse and took out the dildo and went back to the flat screen T. V. and somewhat hesitantly put it in my mouth so she could see it.

"Good, now that I have that on video I own you. The key is stuck in the bottom of your purse in the little pocket. Take the key and reach into your diaper and remove the cage but keep the diaper on and the dildo in your mouth little one." she said.

I did exactly as she said. It took a bit of work figuring out how to remove the chastity cage along with cock ring it affixed to without taking my diaper off but once I did my cock sprang to life.

"Good girl, now listen baby. Most women dominate men by keeping them in chastity till they beg for release. My way is different. I actually want you to play with your little boy clit. You can play with yourself anytime your in a dress and the more you do the further down the road to a woman you'll go. Just one teensy little rule, you cannot touch your boi clitty. You can only rub yourself through your diaper. DO IT NOW and hold up you dress so I can see and keep the dildo in your mouth." she said.

I dont know why but I was actually getting into this so I held up my dress skirt so the tiny webcam above the T. V. could clearly see my diaper and with my other hand I started to rub myself through my wet diaper.

The whole experience was truly awesome. The rubber cock in my mouth, holding my dress up for the cam, rubbing the soggy diaper between my legs and into my dick all the while knowing Lisa was watching. It was too much and I quickly shot a load of jizz into my diaper and collapsed onto my back on the floor in the living room.

"Now wasn't that fun little girl?" she asked and then continued, "I'll be home in a few hours to change your diaper. Feel free to play with yourself all you like, just remember the rules." she said and then added, "You should watch the maid tutorial, it's interactive so you'll need to wear the collar I put in your purse so the house computer can track your movements. Have fun princess."

I lay on the floor in the afterglow of an awesome orgasm for a few minutes after Lisa logged off. I knew she was probably still watching but so what. I spit out the dildo as it was hurting my jaw a little and sat up. On the flat screen was the maid tutorial with a start button.

Intrigued and figuring I was already too far down the rabbit hole to back out, I decided to have a little fun. I went back to my purse but there was no collar, just a pearl three band choker. It did have what looked like a computer chip so I put it on.

I then grabbed the remote and pushed the play button on the maid tutorial.

"Welcome to Millers Maids. Today you'll learn the basics of house work and how to earn those extra tips that make all the difference." The program began.

I watched a bit and after a while I was prompted to go into the kitchen and found that the program would not continue till I had done so and when I did the smaller screen in the kitchen turned on automatically. I listened to instruction that was both instructional and a little pornographic as the man described the best way a maid could get the sexual attention of her bosses.

To my dismay, I found I could not watch anything else on the flat screen till the program had finished so I found myself going from room to room to listen to the next set of highly suggestive instructions and it was making me hard again.

It was in the bathroom that I really got intrigued.

"Now girls, cleaning a toilet can get you the biggest tips but only if you do it right." the narrator began as I walked in and the house computer noted my presence. "You may notice that the toilet seat it very thick, so thick that you could easily stick your head through the gap in the open front toilet seat and into the bowl and close the lid. Men love it when you girls do that. Why dont you give it a try but go ahead and put on the toilet scrubber first."

I saw what looked like a small toilet brush with a handle that was only a couple inches long but when I examined it closely I realized it was also a gag. Apparently the maid was supposed to wear the gag and use her head to clean the toilet. Kinky.

And yet, I was curious. I tentatively placed the ball gag part in my mouth and fastened the strap around my head leaving the toilet brush sticking out of my mouth a couple inches. It felt weird but it was also making me hard again.

Oh, what the hell. I had come this far.

I figured this toilet probably had never been used seeing as it was in a training house so I got on my knees, stuck my head between the opening of the toilet seat and into the bowl all while rubbing myself through my diaper. I tried closing the toilet lid just to see if I could and to my horror, I heard a very loud click.

The toilet seat had locked in the down position with my gagged face still in the bowl.

And then the narrator's voice from the training video began.

"Now remember, many of our clients have these locking seats and you'll get much better tips if you squirm and even cry a little." The voice instructed.

I squirmed but it soon became apparent that only someone else could open the toilet seat to let me out.

Fuck, just one day in a dress, less than a day and I had actually gotten my head locked in a toilet. I reached up and inadvertently pulled the handle flushing the toilet getting my face all wet in the process, but the toilet lid unlatched.

Oh what a relief.

Still gagged with the combination ball gag/toilet brush I tested the lid a few times and every time I flushed it released.

And I was still hard as a rock.

Knowing it was safe, I placed my head back in the toilet bowl and closed the lid locking me in again. This time I had a little fun and started squirming and I actually tried to scream though the gag didn't allow for much of that. Then I reached under my skirt and began rubbing the diaper to get myself off.

It took a lot longer as I had jizzed only a little while ago but that made it all the better.

And finally I came. Holy shit what a rush. What have I been missing all my life? I didn't bother releasing the toilet lid till the afterglow wore off. I just stayed on my knees with my face buried in the toilet bowl. After my dick went down, I wet my diaper some more. I thought it might leak but it didn't

As the afterglow subsided, I heard Lisa's voice through the small T. V. screen where the maid training video had played. "See, your a sissy aren't you? If you quit now and walked away you'd go back home to your mom's basement and jack off in a dress, probably a diaper too. Your hooked and there's not a damn thing you can do about it. Thanks for the video by the way."

She was right. A whole new world had opened up before me. A world that paid well.

After I finished, I watched some Television till Lisa got home.