tagTranssexuals & CrossdressersNew 'Girl' in the Office Ch. 01

New 'Girl' in the Office Ch. 01


I'd been working in an office since I'd finished college until I could get myself a 'real' job. Basically I was a secretary for some of the bigger bosses in the company; nothing exciting but it paid the bills. Although it was what a lot of people saw as 'a girl's job' I really enjoyed it, especially chatting to the other secretaries who were all older women.

I was a 21 year old guy, mostly into girls but I'd never had a serious relationship that lasted more than a few months. I'd also had a couple of drunken one night stands with men that I'd met in chatrooms. Something that I had enjoyed but always felt a bit guilty about. I saw myself a straight although I'd fantasized a lot about sucking guys off, and even about being a 'girl'.

I'd had long hair for quite a few years and I suppose could be described as quite feminine, especially since I had well developed, C cup breasts that I hid away, except from one guy I had a one night stand with.

I'd also experimented with dressing up, although nobody knew my secret. However there were about to be big changes in my life that would see me exploring my feminine side in ways that I never dreamed would happen.

It all began when a new manager started overseeing my office a couple of days a week. He was an older man, in his early fifties but very striking. Around six feet tall with a body that looked trim and powerful under his pinstripe suit, he had dashes of gray in his dark hair and piercing blue eyes. Since I'd started working I'd begun to become more interested in guys and this man captured my attention immediately. At first I only saw him from afar through the glass wall of his office. Occasionally he would smile at me when he caught me looking in the direction of his desk, before I'd quickly turn back to my monitor, blushing.

One day, however, he came to the door of his office and motioned me across. I was surprised at first and mouthed, "Me?", in reply before he said, "Yes Steven, I'd like a quick word with you."

I hurriedly stood up and forced a nervous smile as I walked over and entered his office, closing the door behind me.

"Take a seat Steven," he said, smiling as he straightened his tie and sat down behind the imposing walnut desk. "I'm sorry I didn't introduce myself earlier, I've been up to my ears in work since I started looking into your division's performance. My name is Peter Laveroc, I'm the head of accounting for the company."

I felt a little less apprehensive, since I settled into the comfortable leather chair. And I began to get a sense of exhilaration now that the man I'd been fantasizing about was chatting to me in his office.

"Pleased to meet you, Mr. Laveroc. I'm Steven Smith", I managed to reply.

"Now Steven, I have to tell you that although I like to run an efficient office, I prefer being on first name terms with my colleagues. Please call me Pete."

Slightly embarrassed but with that same thrill in my stomach I apologized and remembered to call my superior Pete.

"I have to say that I've been very impressed your work since I've arrived, and I have a proposal for you."

This almost sent me over the edge with anticipation. Since I'd been working for the company I'd been doing odd bits of administration and dogsbody work for a few of the managers. Mostly I was helping out the personal secretaries when their workload was too much. I knew I was good at my job and had been expecting for a promotion. But, if Mr. Laveroc was going to say what I was hoping he would say, I'd be over the moon.

"Steven, there's a lot of work I need to get done in your division and so far I've always managed without a PA. However I'm going to bite the bullet and get someone to assist me, how would you feel about being promoted to being my personal secretary?".

I had to suppress a yelp of excitement as I replied to his offer. "Yes... ehm, of course Mr. Laveroc... I mean ehm Pete. That would be great."

My new boss stood up, smiling, and outstretched his hand. "Excellent Steven, on Monday your desk will be moved in here and we can get to work," He grasped my hand firmly and looked straight at me for a few seconds that seemed to last for ten minutes and then sat down. "Actually, you seem to have everything up to date with my colleagues' work, why don't you leave a couple of hours early and I'll see you next week."

I tried to keep my composure as I stepped back and went to leave the room, "Thank you, well... I'll see you on Monday morning sir."

I heard him chuckle slightly as I said 'sir' and he replied, "Indeed, Monday morning," as he looked back at his laptop.

The weekend was a blur. I kept thinking about Pete, although I still thought of him as Mr. Laveroc. He had an air of authority that I liked; even though he was always friendly there was a commanding tone in his voice that appealed to my submissive side.

All I seemed to do was masturbate and think about what I would wear on Monday. My preference would have been the black bra, panties and stockings that I would sometimes wear in my room at night. I thought about wearing the panties under my work trousers, but I wasn't sure if I could bring myself to do it. I wasn't 'out' at all and I'd never dressed up in front of anybody before, let alone in public. Eventually I decided that if they were hidden under my clothes anyway I might as well. As intimidating as working with my first real male crush was, it was also incredibly exciting.

On Monday morning I followed my usual routine but slipped on the black silky panties before I pulled my trousers out the dryer, but when I pulled my work clothes on I discovered they had shrunk at least two sizes. Since I was running late as usual, (especially since I'd masturbated in the shower while I lathered up my breasts, my nipples going hard as I came), I had no choice but to put them on and run out the door.

It wasn't until I got to work that I thought about the combination of my panties and the far too tight trousers. I looked round and could see an obvious Visible Panty Line around my ass. I decided there was nothing I could do and walked briskly towards my new office. I opened the door, relieved that I was just on time and found Mr. Laveroc standing behind his desk, shirt wide open and showing his toned chest and torso, as well as the outline of a sizable cock through his unbuttoned fly.

"Oh I'm sorry Steven," he calmly mentioned, "I cycle in to work sometimes and get changed in the office, I should have warned you."

Flustered I replied, "I'm sorry sir, I'll ehm, just step out."

"Nonsense, I'll just be a minute. Nothing you wouldn't see at the gym anyway!".

I forced a polite laugh, "Of course, ehm yes."

I hung my coat up and bent down while I placed my briefcase beside my desk, forgetting about my panties. I heard a cough and then, "I'd guess you work out too then Steven".

Embarrassed but excited I replied, "Well, occasionally...ehm sometimes."

Mr. Laveroc. walked over slowly and said, "Maybe you should come along to my gym sometime Steven, it's a top class place, you'd like it. I'm going to fetch my coffee, there's a report on my desk I want you to proof read, if you want to get going on it."

As he walked out I mumbled a reply, blushing, and tried to compose myself. I went over to the main desk to pick up the report and nudged the mouse, as I lifted it, waking the computer up. As the monitor flicked on it revealed a web browser open at what looked like a porn site. Surely not I was thinking. I noticed my boss chatting to someone across the open plan room and had a quick look.

It was true, Mr. Laveroc's browser was open at the member section of a transvestite and transsexual site. The image enlarged in the middle of the page was of a feminine looking guy sitting on a desk in a white blouse and a short miniskirt which showed off long smooth legs covered in stockings up to his mid thigh, and held up by suspenders.

My thoughts were racing as I quickly put the computer back to sleep and tried not to get an erection. I quickly went to my desk and put the report down in front of me, just as Mr. Laveroc walked back into the office and sat down.

"I just need that proof read Steven, I'd like it done this morning so I can get it sent off today." he said as he returned to his seat.

I could feel my cock getting hard and pressing against the underside of my desk as I told my boss that would be fine.

After a couple of minutes I heard him say, without looking up from his screen, "Actually I'd like to get a few lengths in at the gym at lunchtime. Do you fancy joining me?" He looked up and smiled.

Suddenly panicking inside. I stuttered, "Ehm, well..."

Then my boss interrupted, "Steven, you really should. It's a top class place. Very exclusive, we'll probably have the pool to ourselves. I insist. What do you say?"

I fumbled for words while I thought about the consequences of the offer. "Well, yes, that would be great. Ehm, thank you sir."

Mr. Laveroc smiled saying, "Excellent. It's not far, we can walk round at noon."

Apart from not having a towel, or swimming shorts with me, my big problem was getting topless. Could I get away with people not seeing my breasts, and my panties? Or did I even want to hide them considering who I'd be with, and what I'd just discovered about him.

The next few hours felt very long indeed as a thousand thoughts ran round my head and I tried to keep my cool.

To be continued...

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