Suddenly His Secretary

I had a secret, well actually, two secrets.

My name is Michael, well it used to be Michael, and I worked in a customer care center for an insurance company. It was loud and frantic. Sometimes I answered the phones, listening to abuse from customers. Mostly though I worked as a team leader dealing with HR issues, mainly persuading others to get through their calls faster.

I answered directly to a vice president called Landon. Once a week I had to go up to the VP suite on a higher floor and be quizzed on facts and figures. How many calls were we getting answered? What could be done to cut costs? Who should be fired?

Landon was the biggest of big swinging dicks. He was tall, handsome, charismatic, confident and sure of himself. He didn't give me any autonomy. He said what he wanted and my job was to say "yes" and make it happen. Occasionally he'd ask me to do minor errands for him, putting me firmly in my place. My first secret was, I enjoyed it.

I was a submissive longing for someone to dominate me. I had entered into a surrogate one-sided domination and submission relationship with Landon. The only thing was, he didn't know anything about it. I just did whatever he asked without question as if it was an order. He didn't know I would never say no to him. I loved it when he would send me to grab him a coffee or something menial. I enjoyed the thrill of humiliation from being visibly beta to his alpha.

My hours of work were about to be cut severely and I was going down to only three days of work a week. I needed an extra job otherwise I'd be in financial trouble. I was browsing through alternative positions at the same company when I came across something that interested me. I'd have to discuss this with my two best friends though.

....

I got a warm inner glow of pleasure from the glances of every passing man. I'd occasionally meet their stares and smile back at them. I was feeling attractive, relaxed and completely at ease. My champagne colored, sequined cocktail dress shimmered under the lights of the bar. I had my legs crossed and the top of one my stockings was just teasingly visible.

My second secret was I loved cross-dressing. Not just that, I considered myself somewhat of an expert. I had years of practice, I had my make-up done perfectly, just subtly hiding my masculine features. What I couldn't cover with make-up was disguised by my blonde wig. I had my waist cinched in, my butt slightly padded and some silicone gel breast inserts giving myself a female figure. I'd been to voice training and could pull-off a passable feminine imitation.

I had met up with my two best friends for drinks. Ellie was a fellow cross-dresser who I'd met at a drag event. She had introduced me to her long time friend Sophia who was a natural born girl. We always went out together as a group girlfriends and I loved it. I don't think I had ever once seen them without being dolled up en femme. When in female mode, I went by the name Michelle.

Sophia was effervescent and endlessly partying, enjoying life to the full. She was always bored and looking for some distraction and something new. She was also from a very rich family. She was generous and would often pick up the bar tab for us poor folks. She took me and Ellie shopping sometimes and bought me this fabulous designer dress, the price tag of which was far out of my league. She even took us on an all expenses paid vacation once. I had the best time of my life.

Sophia was telling us about the first world problems of a one percent princess. Her father was subjecting her to the terrible horror of being 'forced' to finally get a job or he was going to stop her very substantial monthly allowance. Sophia had other ideas though. She was oblivious to the fact that us regular folks faced this same terrible oppression every day. Sophia was allergic to work and would rather be flying on her father's jet to a beach somewhere. But wouldn't we all. I must say, I was insanely jealous of her lifestyle.

Sophia noticed I'd stopped listening to her droning about her non-existent problems and caught me making eye contact with a passing man.

"So, are going to fuck one of these fine specimens or what?" Sophia asked with some exasperation, gesturing around at the wide selection of available gentlemen.

"You know I'm not gay," I replied.

"Because hanging round in bars wearing lipstick and pouting at men is totally not gay. There's nothing that says straight man more than a mini chiffon cocktail dress and heels." She leaned back in her chair and looked at me with a piercing stare. "When you look up 'denial' in the dictionary, there's a picture of you," she playfully accused. "That guy over there," she pointed, "you'd suck him dry in a heartbeat."

"I'm not pouting at them. I just ... enjoy being admired," I correct her.

"Admired? Or are they trying to work out if you have a dick?" piped up Ellie. I shot her a look of daggers. "Joking! You're absolutely gorgeous honey. I wish I looked as good as you."

"Thank you babe. You're beautiful too." Sophia coughed to attract attention to herself, noting her omission. "We're all fucking sexy bitches. Are we all feeling secure now?"

Sophia firmly grabbed the wrist of an unfortunate passing man. "Excuse me, can you help me out?"

"Er ... I guess," the startled man couldn't really avoid her as she was physically restraining him with an iron grip.

"Can you tell me, which of us do you think has a penis?" Ellie and me burst out laughing. My drink nearly came out through my nose.

"What?" He was deeply confused.

She stared at him like a psycho before declaring "It's me!" She released his wrist and he rapidly backed away from the mental patient, looking at her with disgust. He tripped over something while walking backwards and disappeared far away to the other side of the bar.

"I don't know about a cock but you've definitely got balls," I told her.

"That I have, and I've also got the number of Daddy's lawyer," she replied. "So much trouble caused by such a little girl. He's such a sweet and helpful man."

"Talking of trouble, I've got something absolutely crazy to discuss." I piqued their interest.

"I'm thinking of applying for a new job."

"Great. What is it and where?" Sophia asked.

"It's a part-time personal assistant job to a vice president."

"So is that like a secretary?"

"Yeah exactly, a secretary."

"Not your usual thing honey. Are we branching out into pastures new?"

"Yeah in a way. The thing is, I was thinking of kind of maybe going dressed a little differently to normal."

There was silence for a couple of seconds before Ellie and Sophia said in unison: "Oh ... my ... god!"

"You're not thinking of...?" she gestured at my outfit.

I nodded.

"I'm going to apply as a woman." I confirmed their suspicions.

"Why the hell would you do that?"

"I don't know. It's really exciting to me. I just want to see if I can get away with it. I want to know if I can really pass as a girl. I'm not actually going to take the job. I'll just turn it down if they offered it."

There was a short silence.

"I love it!" blurted out Sophia with a wide smile. "Ha ha! Oh I love this so much! So where is is it?"

"The place where I work now."

Ellie nearly choked and spat out her drink. When she recovered she shouted "No!"

"Yes!"

Ellie and Sophia looked at each other with disbelief.

"OK, so here's what's happening now," Sophia declared. "The bar is totally open for whatever drinks you both want. Nothing is off limits and I will pay. But ..." Sophia pointed at me, "I bet you the bar tab for tonight that you won't go through with it."

"Well I'm going to have to put in an application form first, they might not even see me."

"OK, so the rule is, if they agree to see you for interview, you have to go through with it or you cover whatever massive check is coming tonight. And before you agree we are spending an obscene amount of money tonight. Deal?"

I thought about. This would bankrupt me if I chickened out. Maybe it was good to have a strong incentive. "Deal."

Sophia and Ellie squealed with delight and ordered a bottle of expensive champagne to the table. I could see the cost of failure stacking up. I was locked in.

"Wait! Wait!" I suddenly thought of a problem and felt deflated. "No, it's impossible. I can't do it. I'm such a complete dumb-ass."

"Yeah we know!" Ellie joked. I gave her an unimpressed look at her sarcasm.

"How am I even going to get past the front desk? The security guy won't let me into the place without ID. It's not like I can use my building access card with a man's face and name on it."

Sophia turned to me and smiled. She reached into her purse and pulled out a card before sliding it across the table towards me.

"What's this?" I asked, picking it up

"It's your new ID. Will a driver's license be OK?" she leaned back with a smile. "A brunette wig and you're me. I mean how much do people actually look like their license photo anyway? How closely are they going to check it?"

"This sounds like such a bad idea."

...

'Sophia' nervously strode into the lobby, her heels clipping on the marble floor as she walked. I handed over my ID to the bored security guard who gave it a disinterested cursory glance. He checked a list of names and then let me through. I'd filled in the job application form in Sophia's name. Three days later I got a shock as they called me in for interview. The real Sophia had dropped me off, together with her accomplice, just to make sure I actually went inside. A bet is a bet.

I was wearing a professional black pencil skirt, black pantyhose and a fitted jacket with a white top underneath. Sophia had bought me a new high quality wig that was the best match for her hair in the license photo that we could find. I'd applied my make-up to match what she had been wearing as closely as I could. It was far from perfect, but it had smoothly got me past the first fence without a hitch.

The receptionist was the same one I passed every day on my way into the building. She smiled at me with not a glimmer of recognition at all. I gave her Sophia's name and she handed me a temporary ID badge and told me to wait on a sofa. I saw people I knew stride past me. I had thoughts of being outed running through my brain on a loop. I started catastrophizing. I had a horror filled vision that somehow the police would be called and I'd be arrested. In my mind I was in handcuffs in the back of a police car for fraudulent use of an ID.

I could see Ellie and Sophia in the parking lot in the distance looking at me through the window. I waved at them for support. I fished out my phone from my purse and messaged Ellie - "Terrified. I think I'm going to wet myself."

"You can do it," replied Ellie. I couldn't chicken out now, I was nearly there.

A woman came down to collect me, I recognized her as Mia, a secretary I had dealt with many times.

"Is it Sophia?" she asked warmly.

"Yes. I said."

"Great to see you. We're ready for you now. If you'll just come with me."

She took me up in the elevator and made some polite small talk. My heart was racing, I was nervous as hell as she took me to a office with two outer secretarial desks.

"Just through there." Mia pointed me at the inner office door and she took up her position at one of the desks. I took a deep breath and went through.

The office was lavishly decorated. An executive was sat at a large walnut desk and it was exactly who I expected. Landon was on the phone and motioned me to sit down and wait. I'd applied to be one of his personal assistants. Just the idea of being submissive to him every day gave me an incredible rush. I'd not been completely honest with Ellie and Sophia about my intentions. I was looking for a new way to get him to have power over me. I thought an interview would make me feel weak and at his mercy.

I sat with my legs together and my purse resting in my lap as he talked on and on. He made me wait in silence for maybe 15 minutes, making no attempt to finish his call. He had barely noticed or acknowledged me in any way. I was clearly of minimal importance to him, but that's exactly what I was hoping for. I wanted him to have total power of me and make me feel small. I wanted to be weak and subjugated.

When he eventually hung up, he turned and took a real look at me. He paused for a few seconds, seemingly examining me. There was an awkward silence. His expression looked confused more than anything. His brow furrowed and his eyes narrowed a little. He was in thought. Had he seen through me? Had he recognized me? I immediately tensed up and my heart raced. I unconsciously twisted in my seat slightly towards the door, ready to make my escape. I prepared for him to blurt out my male name or start laughing uncontrollably but he didn't.

"Hi, I'm Landon," he said eventually after much too long a silence. I shook his hand. He didn't apologize for making me wait so long. That was not his way.

He made a little small talk and then asked me about my previous personal assistant experience. I told him I'd been working at Sophia's father's company and that was the only place I had ever worked. She'd told me to say that, she thought she could probably figure something out if they ever called to check. I'd researched some general secretarial duties and lied about things I had been doing.

Landon wasn't that interested in hearing about it. Within a few minutes he had turned the conversation around and talked about himself. He got up and walked around me. I loved feeling small in front of him as he towered above me. He sat on the desk and looked down at me, his powerful and confident pose diminishing me to nothing. I felt weak at the knees. I loved it.

I hadn't really said much at all, but eventually he declared he had everything he needed and they'd be in touch.

"Thank you Sir," I said. I'd always wanted to say that to him.

"Oh, we're informal round here," he replied. "Just call me Landon." He extended his hand warmly and I shook it. I had a weak, limp grip and he nearly crushed me with his powerful grasp.

I strolled out of the office, with a smile on my face, pleased with myself for going through with it.

"Oh someone looks happy," said Mia.

"Yeah, I think it went well thanks," I told her.

"Well, best of luck. I hope to see you working with us soon."

"Thanks, fingers crossed."

I raced out of the building and got in the car.

"Well?" shouted Sophia.

"All went well. Got away with it. They never noticed." We all laughed and went out for drinks and I told them all about it.

...

A few days later my phone rang just as I was getting out of work and I answered automatically, "Yeah, Michael here."

"Oh! Hi... I'm sorry, maybe I have the wrong number. I'm looking for Sophia?"

I cursed, I'd answered with a male voice. I shouted Sophia's name and waited a few seconds. "Hi there, this is Sophia," I said in my female tone of voice.

It turned out I'd got the job. I couldn't believe it. Shit. Now what? Time for a conference with the girls.

I got Sophia and Ellie to meet me immediately at a bar. This was an emergency and I didn't have time to change into my more usual attire. Sophia turned up first and walked straight past me.

"Hey!" I shouted at her.

"Sorry honey, I'm looking for someone." She thought I was hitting on her. She'd never seen me as a man before.

"It's Michelle."

"What?"

I looked around and no one was paying attention. I did my feminine voice. "It's me dumbo, I'm not dressed up."

"Oh!" She sat down at the table. "Sorry, I've never seen you before like this. Wow! You're a cutie. If I didn't know you were gay as fuck I would do you."

"Thanks. And I'm not gay."

"You just keep believing that. Now what can I get you?"

We got drinks and Ellie turned up. I told them I got the job. Sophia clasped her hands in delight.

"So mission accomplished," I said.

"Mission just beginning," said Sophia. "So are you taking the job or what?"

"I can't, that would be crazy."

"How the fuck can I do that?"

"Well you call back and say yes,"

"What about social security number? Paperwork? Job stuff?" I challenged.

"I can give you that," smirked Sophia. "Tiresome Daddy keeps trying to force me to get a job like some sort of pauper. It's just not my scene."

"What?" I was confused.

"Here's the deal. You go to work and pretend to be me. I will give you everything you need. You give me some paystubs to prove to Daddy I got a job and I go to relax on a beach in Turks. Everyone wins."

I sat back in my chair and thought about it.

"Or maybe Barbados, I haven't decided."

"Do it!" ordered the mercurial Ellie, sipping at her drink.

...

Sophia's first few weeks at work had been hectic. The assistant job was part time and I still retained my other job as Micheal. I came in three days a week as a man and then switched gender for the other two days. Sophia and Ellie thought I was insane but the money from the two jobs was useful. I had a lot to do learning the ropes, with being the new girl. I shared to the job with Mia but we worked different days. She did the first part of the week and I did the second.

My interest though wasn't in spreadsheets and calendar appointments, my hope was to try and get Landon to dominate me. I'd tried to start up calling him "Sir" again, but he pushed back on that and insisted on first name terms. I had picked up a few of the menial jobs that I liked. I offered to grab him his morning coffee, I got his suits cleaned and paid his bills for him, but I wanted more. I wanted a lot more.

With being his assistant, I'd got to know his personal life quite well. I knew he was getting divorced, now lived in an apartment away from his wife and he was lonely. I wondered if the confidence was just a facade. I felt sorry for him.

I was instantly available to him at any time. I tottered about on my heels and I loved catching him glancing at my ass and checking out my body. He made me feel desirable. The professional barrier between us didn't crack though. I pushed the boundaries of the corporate dress code, but he was perfectly respectful. I was surprised that he was a good boss to work for.

One day, everything changed. It was a day that would stay with me forever. Landon came out from his office and wanted me to look up some HR records for him. I agreed, it was no problem. He wrote down a number and passed it to me. I was typing it into the system, but half way through I completely froze. I suddenly recognized what it was. My face went white with fear. I finished typing in the number and hoped I had mis-remembered. Up on the screen came a photo of me, but also not me. I had just typed in Michael's employee number and the records from my other life were on the monitor.

"Can you print all that out for me please?" asked Landon, smiling at me.

I looked at him for a moment and then back at the monitor. A wave of terror washed over me. "Erm ... yes, sure thing." I had a lump in my throat and my heartbeat was increasing.

I went over the printer. Landon stood closely behind me. I could feel him breathing down my neck. The machine warmed up and then a few sheets of paper appeared. My male face was printed out in full color. I held up the pages for him to take without making eye contact. He snatched them from my grasp.

"Great, thanks. I just need to ask Michael something. I'm sure he won't mind me calling him at home."

I stayed at the printer, staring away from him at the wall. I wanted to run and hide but Landon was close behind me, completely blocking my path. He pulled out his cellphone from his pocket. He read some digits from the page and dialed them into his phone. Suddenly, my purse started ringing. My anxiety went through the roof.

"Oh, you're getting a call I think. That's a coincidence. Do you want to answer that?"