A lot of my stories are based upon the more formative years of my sexuality. Things are much less complicated these days. There's less sneaking around as I am not quite so in the closet any more, as well as the fact I live alone in my own apartment. I divide my time quite evenly between my identities although work is somewhere I still don't bring my cross dressing.
Sometimes I feel like a super hero, by day I'm a mild mannered office man but away from the work I am "Super Jess"- spreading joy in high heels and tight skirts. I almost always keep my work and private life separate as it's just easier. Some may not like that I have long hair or notice how smooth and soft my skin is but no one knows about my secret life so it never causes many problems.
A couple of years ago, I unfortunately lost my job and I was beginning to worry what I would do when I received a message with an interesting offer. Like most people I'm on a few social networking sites in some way or another. I actually have two profiles on most of them thanks to my dual identities. After 2 months of job searching I had taken to asking around on Facebook if anyone knew of any jobs in my particular area of expertise. It seems in my weariness one day I had accidentally updated from my Jessica profile about my employment problems before I went to bed.
When I woke up I found dozens of comments from people making various subtle, and some not so subtle, lewd suggestions as to jobs they may be able to give me or perhaps provide for them. I guess this is the drawback of accepting all friend requests. There was, however, a private message sent to me from a man who spoke politely, professionally, and respectfully.
He introduced himself as Michael and explained that he was a self employed something or other who operated an office in a shared floor. His job sounded like it was invented by someone to fill a need that no body knew existed simply because it was a need that no body had. He explained that he was looking for someone to be a personal assistant for him and that if I was interested I could get in touch with him.
Normally I would ignore such a message but after 2 months of unemployment the cupboards were beginning to look a little bare and a quick search online found him to be legitimate. I returned his message and inquired further as to the role, expectations, salary and other details. He replied promptly and, once again, I found his manner to be completely professional so I agreed to his invitation to an informal interview.
I had often wondered at the prospect of being Jess full time, of course I had spent extended times without returning to guy mode but I always wondered if dressing up would maintain it's allure if I was dressing for work every day. I often hear female friends complain about the expectations placed upon them to always look good although mostly they complained about shoes or declared their envy at my clothing freedoms. Despite not needing any work clothes over the years I had bought so many different outfits I almost had too much to choose from for my interview.
I opted for a black knee length pencil skirt and a white blouse, the classic office look. I would wear my hair up and made sure my make up carried on the classic theme with dusky eye shadow and bright red lip stick. My heels were black, not too high, and perfectly matched my outfit. Continuing the classic feel I opted for a black lace bra, which was ever so slightly visible through my blouse, matching lace thong and suspender belt. To complete the look I chose a pair of flesh coloured stockings with a black seam leading up to black lace tops. I felt sexy and confident as I dressed and I briefly thought I would relish being able to wear these outfits daily as I donned my jacket and headed out.
I arrived at Michael's office and he met me in reception. He greeted me and led me to the elevator and then through a hive of corridors and nondescript office doors. Eventually I saw a small plaque announcing the name of Michael's company on one of the doors which led to a small outer office which, in turn led to Michael's office. He had told me it was a small operation but I wasn't quite expecting this small. I was invited to sit which I did. This gave me an opportunity to see Michael properly for the first time.
He was in his late forties, a slight belly under his plain white shirt with a once expensive suit beginning to look a touch shapeless. His hair was close cropped, possibly in an attempt to hide his thinning scalp. He was a man who looked like thousands of others in London. We made small talk and discussed the role and various other interview type questions. As we came to finish up he asked the usual finisher.
"Do you have any questions for me?"
"I do actually. Why would you want a girl like me? This job seems pretty standard PA type stuff and there are plenty of people who would be better suited." He seemed somewhat uncomfortable at the question. "From the looks of things I'd say you don't even need an assistant here." He started to blush a little.
"I.... Erm... " he stammered." I need a manager. Someone to... Erm... Be in charge of things. Some to organise me... Someone to... Tell me what to do... " That last part rang a little bell of recognition for me. I'd seen it countless times before. Some people get a little shy when they're asking for what they really want, but if you can read between the lines then you can save a great deal of time. Michael, it seemed, with his well paid job, his luxury car, and his long standing wife, had the need to be submissive. It's a cliché that business men enjoy this but clichés exist for a reason. High stress and pressure can lead to a desire to be utterly helpless.
"Michael, are you asking me to control you or the office?" I feel in these situations it's best to be direct.
"Me." He replied timidly. I have experienced many different situations in my 30 years but never quite this. I'm friends with people from all walks of life and I'm not ashamed to say I have acquaintances who are professional mistresses and I've often been intrigued, and not a little jealous, over their chosen profession. I'm sure I could have a little fun and earn some money at the same time. I reached for my hand bag and from it retrieved a cigarette.
"You can't smoke in here", Michael told me.
"A lighter. And an ashtray. Now." I told him sternly. "What makes you think I would be your boss, Michael? What makes you think a woman like me would want to work with you?" As I spoke he searched around his office and produced a lighter and cup. He presented them to me as I finished my questions. I held my cigarette out to him.
"I don't smoke."
"A lady doesn't light her own cigarette, Michael." He hurriedly took the cigarette from me and inexpertly lit it. He suppressed his coughs as he handed it to me. I took a long draw from it and blew the smoke towards him. "Are you going to answer?"
"I can pay you", he stumbled. He already looked like a child being told off, his hand clasped in front of him in front of his crotch. It's funny how some guys do that, subconsciously protect their balls when they feel threatened. I raised my eyebrows to him.
"Pay me? Am I a whore, Michael?" his face dropped as he realised the implications of his offer.
"No, Jessica, I'm sorry! I meant nothing by it!" I stood up and walked behind his desk before sitting in his chair. Michael, still stammering his excuses as he stood by my now vacant chair, held a look of fear and excitement as I reclined and placed me feet on his desk.
"Shut up, Michael." He fell silent. I pointed to the floor by the corner of his desk and like a well trained dog he quickly stood there. "Drop your trousers and underwear Michael." Without question he unbuckled his trousers and pushed them to the ground along with is boxer shorts. His average looks extended to his average size cock which already stood hard. "You will refer to me at all times as Mistress or Miss Rhodes, is that clear?"
"You're going to masturbate for me while I speak but you are not allowed to cum until I give my permission. Do you understand?"
"Yes, Mistress". With that he gripped his cock in his right hand and began to masturbate. I observed him for a moment as he stood there, focusing on some point in the distance as he attempted to maintain his composure.
"We're going to have a contract, Michael", I enjoyed using his name so frequently, I find it can be strangely belittling. "This contract shall be legally binding. Firstly you will pay me a salary for time spent here in the office. I'm not a greedy person. Thirty thousand pounds a year after tax has been my average salary of late so this is what I expect "
"Yes, Mistress." His response as his hand worked the length of his cock.
With my legs still upon his desk next to him I gently eased my skirt up. His eyes, drawn to my movements turned and followed the hem as it revealed the dark lace of my stocking tops. His eyes grew wide as I toyed with my suspender clasp.
"Due to the unusual nature of my work you will provide me with a credit card. This card will have no limit and you will pay it's balance without question."
"Yes, Mistress. " He watched me as I teased my blouse open to show my modest cleavage inside it's soft lace trappings. I could see he was struggling to maintain his composure.
"This is the most important part, Michael. You will do exactly as I say at all times, without question. If you do not this will be a breach of contract and I will sue you. I'm not sure your wife will be able to understand why you have such a contract. Do I make myself clear?"
"Yes, Mistress." I sat up straight and planted my feet on the floor. Lifting my skirt higher I spread my legs and arched my back, clearly displaying my cock encased in soft black lace.
"You will be my property, Michael. I will own you. You will be my toy." As I spoke I ran my fingers up my stockings. My false nails shining bright red, matching my lipstick.
"You may cum." I told him.
Within moments his body jerked as he shot load after load of cum into a pool on his desk. He stood there stupefied for a moment, a fine string of cum hanging from the tip of his dick.
"Fetch me your wallet, Michael." He bent down to his trouser pockets and handed me his wallet. Inside were several twenty pound notes, possibly three hundred pounds. I took them put and stuffed them into my bra.
"Lick up your cum", I ordered. His face met the desk as he eagerly lapped at his seed. I straightened my skirt as I stood before buttoning my blouse back up and collecting my hand bag. I looked as Michael finished swallowing and stood up straight.
"Did you enjoy that, Michael?"
"Yes, Mistress. Thank you, Mistress"
"That's going to be the last time you're allowed to cum for quite a while", I announced. "I'll see you on Monday, 9am" I informed him, and with that I turned and left.
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<a href="https://www.lushstories.com/stories/crossdressing/the-secretary-part-1.aspx">The Secretary - Part 1</a>