A Sissy Promotion Pt. 01

So, here is my story such as it is.

I never set out to be gay. Hell I never even liked guys at all. Growing up I always fantasized about pussy, pussy and more pussy. So how did I end up being the pussy?

It all started a few weeks after my nineteenth birthday.

I had been working at Miller's Property Management since I was fifteen. I started by sweeping up in the warehouse after schools and weekends and when I graduated highschool last year they put me on permanently.

The company had seen better days. At one time it managed over a hundred properties, mostly janitorial and custodial contracts but now better than half the company vehicles sat unused in the parking lot and fully two thirds of the warehouse was empty. Only the maid service contracts were bringing in any real money.

I expected to get laid off any day now and I couldn't have been happier. Summer was just staring and the prospect of collecting unemployment while hanging at the beach really appealed to me.

"Tony, the old man wants to see you in his office." Lisa, the office receptionist and one of the few office workers still employed said as I punched in for work. It was obvious she had been waiting for me.

Well, here we go. Summer here I come.

I walked over to the offices on the other side of the warehouse wondering how long I would have wait for my first unemployment check and how many weeks I could keep drawing them. I was almost giddy.

I had no idea.

My Miller's office was open so I gently knocked and asked, "You wanted to see me sir?"

"Yes, yes, Come in, come in and have a seat. Lots to talk about." He said and I got the feeling this wasn't about getting laid off at all.

I took a seat and waited for Mr Miller to begin.

"Listen Tony, things are really gonna pick up around here. I just landed a contract for all the janitorial, custodial and land maintenance work at Heath Holdings... Pending a few minor details." he explained.

"So, I'm not getting laid off and spending the summer at the beach?" I said a bit sarcastically though I was bummed out.

"Well that depends. You see there a few things William Heath demanded as part of the contract negotiations and that's where you can help. It would mean a huge pay raise and a promotion, even a company car." he said as he eyed me intently to gauge my reaction.

"More money, hell yeah. Anything, what do you need?" I asked excitedly.

"To explain that I have to tell you a little about Bill Heath. You see his son is one of those you hear about in the news. You know, boys who want to be girls or some such and his daughter is in a wheelchair so Heath wants to make sure any company he does business has disabled and trans people on the payroll and that's how I landed this contract. Following me so far?" He explained.

"Um, not really sir. Are you saying your planning to hire a drag queen or someone in a wheelchair?" I asked a bit confused by the turn in the conversation.

"First, dont call them drag queens. Just think of them as women and second, no, I'm not planning on hiring a trans or disabled person because I told Mr Heath I already had a slightly disabled trans person on the payroll." He explained.

"Wow, I had no idea. Who is it, one of the cleaning ladies?" I asked genuinely wondering who it was. They all seemed so normal.

"To be honest, I was hoping it was you." Mr Miller said as he got up from his desk and walked over to the bar on the other side of his office where he poured a drink.

"Me, I'm not gay or trans or whatever and I'm not disabled in any way. Perfectly healthy here." I said as he put the glass of whiskey on the desk in front of me.

"About that, I lied. I was desperate and needed this contract so I made up a story about a transsexual working in my office. Now I'm stuck for it and need your help. Can you help me? Like I said, it comes with a huge raise and lots of benefits." He said as he motioned for me to drink the whiskey.

I was over eighteen by a year but still two years to young to drink but I had drank whiskey before. What red blooded american kid from Alabama hadn't? so I drank it down. It was cheap and burned as it went down. Not that I ever had expensive before.

"I'm not sure what you want from me sir." I said practically coughing from the whiskey.

"You make $16.85 an hour correct? Dont answer. You still live in your parents house right? Again dont answer. And you take the bus to work. Well if your willing to go along with this little plan of mine, I am willing to pay you $120,000 a year to start, give you a company car and an expense account. Your own office and of coarse all the usual bennies like medical, dental, vacation and 401K. Are you following me now?" he asked.

"You want me to pretend to be a guy who wants his prick cut off? To come to work wearing a dress and pretend I like guys? For real? Really?" I asked astounded.

"Not just a dress but you'd have to wear a diaper too. Thats the disabled part. But essentially yes." he said.

"Look, I can see you're in a bind but I can't do this, I wouldn't even know how. Why not just hire someone? And seriously, a diaper?" I asked.

"I can't just hire someone, I need someone who is already on the payroll because that's what I told Heath. Look, I'll sweeten the deal, You know that show house we use to train the maids? I'll make that company housing and throw it in as part of the deal. Free rent. Plus I give you an executive signing bonus of say... $5,000." He said and it was obvious he was really desperate. The company must have been in worse shape than I had realized.

"It would be just at work right? I wouldn't have to go prancing around town in drag or anything like that?" I asked astounded that I was actually bargaining. What the fuck was I doing?

But the money.

"I could tell Bill Heath that your just learning to be a girl so you only dress up for work but as for the diaper, you can't turn that on and off so it would have to be 24/7 and maybe sometimes at public events where Bill Heath is going to be." He answered and a glint of hope shown in his eyes.

I thought about it and realized that I had him over a barrel. Tyrone and Jacob in the warehouse would never go for this and practically every other guy in the company couldn't possibly wear a dress cause they were too big. As I thought that thought I realized I had been chosen because I was only five foot five and skinny as hell and could probably fit in a dress.

"If I did this, I would want $25,000 and I get to keep the car and house... Permanently." I bargained.

"All right, if you last a full year I'll sign over the house. Its a tax and maintenance shithole anyway, and the car but you have to be here every day in a dress and makeup. The whole nine yards. Plus wet your diaper, you have to pretend you need diapers." He said and just like that we had a deal.

"Go see Lisa, she will get you what you need and be available to help you as needed." He said and with that the meeting was over.

What the hell had I just agreed to?

I walked over to Lisa's desk at reception and asked, "Boss said you'd get me what I needed."

"So you took the deal, I figured as much. Come with me." She said as she grabbed a large bag from under her desk and then got up and led me to the ladies room.

"What do you mean by 'I figured as much'" I asked.

"Never mind. Rule number one. Ladies room from now on. No matter what. Now strip and lay down on your back on the floor." she said a good deal more sternly than I had ever heard her speak before.

As I stripped I looked around and noticed that the ladies room was much cleaner and nicer than the mens room. I also noticed Lisa removing some womens clothes and a huge diaper from the bag she brought in with her.

When I was naked she motioned for me to lay on the floor.

"Sometime next week there will be a changing table in here, probably over there by the tampon and pad dispenser. It will be easier for me to chance you than for you to change yourself till you get used to diapers. This is a chastity cage to keep from getting an erection and spoiling the look of your dress." She said as she put the metal thing on my cock and then diapered me into what had to be the thickest diaper in the world.

"It's awfully thick and makes a lot of crinkling noise when I move. What kind of underwear do I wear over this to make it quieter." I asked as I took a few steps and noted the awful thickness of the diaper and the strange sensation of the chastity cage.

"A diaper is underwear and we need you to be conspicuous so people know your diapered. Your putting on a show remember. Now sit in that chair and I will show you how to roll on a pair of stockings.

Stockings and a waist cincher with garters were first followed by some ladies shoes which fortunately only had a small half inch heel.

"Now, wet your diaper. You need to get used to wetting yourself as you are pretending to need diapers right." she demanded.

"I can't, I just went before I got to work." I said.

"Fine, this is your company credit card. Go to the vending machines in the cafeteria and get some sodas or coffee and drink up. I'll be back in about a half hour as I have other things to do." she said with an evil smile on her face.

"Dressed like this?" I yelled but she ignored me and left,

The cafeteria was right across from the restrooms so I took a cautious peek out the ladies room door and seeing there was no one around, I quickly walked across the hall and to the machines in just a diaper, stockings and garters plus the shoes of coarse.

I bought three cans of soda. I have never used a credit card on a vending machine and I was terrified someone would walk in on me while I tried to figure it out but no one did.

Once back in the ladies room I downed two sodas and just waited. As I did, I took a look in the bag Lisa had left behind.

There was a dress and a full slip which I was meant to wear but also a bra and a couple large fake silicone titties. There was also a small brown leather purse that was full of makeup and hair stuff women always seemed to carry.

After about fifteen minutes I was able to pee and when I did I was surprised at the feeling of wetting a diaper. It sagged slightly but held firm.

When Lisa returned, my diaper was good and wet.

"Ok, let" finish getting you dressed." she said as she pulled the bra and fake tittie out of the bag.

"What about my diaper." I asked hardly able to believe I had actually said the words.

"Those diapers are good for two or three good wettings so you'll be fine. Mr Miller says your moving into the maid training house. Nice neighborhood, I'm actually jealous. I arranged to have your diapers delivered there and changed the address we have for you in our files. Now, arms up young lady." she said almost joyfully.

I endured having fake C cup titties glued on my chest followed by a bra. Then came the slip and finally the dress which to my surprise fit rather well, probably due to the waist cincher which held in my stomach.

The dress was purple and matched my shoes and came to just above my knee. The slip was three inches shorter.

"All right then, I'd say your ready to go. Here is your purse, might as well put your wallet in there and your company credit card. You'll need that for expenses and such. Here is the keys to your car in the lot and the keys to your house." she said handing me everything hardly leaving me time to look at myself in the mirror.

"What kind of expenses?" I asked.

"You can't wear that dress forever now can you. You'll need lots of clothes, shoes, makeup and the like. Also you'll want to make regular trips to the salon. And if you need dinner out just put it on the card as long as it's business related. That's code for anytime your dressed you can eat out for free baby. Go to the movies for free, sure as long as you're wearing a dress." she explained.

"I can do all that on the company dime?" I asked not sure I would want to go out dressed if I didn't have to.

"Sure why not? If you're feeling frisky there is a guy on Palmer street who takes credit cards, he'll give you a nice spanking for a hundred bucks." she said laughing.

"What the fuck?" I asked.

"Just go with it, might as well enjoy the lifestyle. Mr Parker has some papers for you to sign and your bonus. Plus I think he wants to see you all dolled up so run along sweetie." she said now laughing openly.

And so, carrying a purse, wearing a dress, in a wet diaper covering a chastity cage I walked back to Mr Miller's office.

"Lisa did a job on you. Wow. And I can even tell your diapered, are you wet?" he asked.

"Yes, she made me." I answered.

"Thats a good girl. Now here is your bonus and the new employment contracts for you to sign." he said indicating the papers on his desk. I quickly went over them and signed.

"Okay then, its Wednesday so take Thursday and Friday off to do some shopping and I'll see you back here on Monday. By the way, your my new private secretary so your office is right next to mine. And if you need any help, just call Lisa. I've made sure she will be available to help with anything you need." He said ushering me out of his office.

I walked back to reception and asked Lisa, "Mr Miller says I can come to you if I need any help. How about shopping?"

"I'll be at your house tomorrow around 7am for a day of girly fun. Oh by the way, that chastity cage locks and I have the key. Call me when you get home sweetie." She said giggling.