Dress for the Job You Want

Author's note: Although this story is fictional, it is inspired by a series of conversations I had with an old acquaintance of mine, now sadly no longer with us, about his time working for a Financial law firm in London in the 80s.

Archfield & Brewster was one of those companies; impossibly old, monolithic, and so full of esoteric and byzantine quirks, rules and customs that it could qualify as a secret society. It was a giant in the legal sphere, and so rife with nepotism that it was almost a closed shop -- you absolutely had to know someone, or be related to someone in order to be employed there. The silver lining to that was that it was almost impossible to get fired for anything less than straight up criminal activity.

I was eighteen years old and fresh out of education when my father, who had worked there all his life, put me forward for a position in the company. I was sceptical; firstly, I wanted to go to college, and secondly, I didn't think for one moment that I would fit in. I'd been there a few times with my father, and everyone seemed impossibly straight-laced and impeccably turned out, from the senior partners down to the office boys and girls. They looked as if a magic spell had been cast on a 1950s office wear catalogue that had brought all of the models to life. The men all looked tall, lean, and filled with an old-world understated masculinity. The women all looked demure, graceful, and the very picture of subtle and professional beauty. Whereas I was small, slim, and perpetually looked like I was on the verge of terminal existential angst. My hair was shoulder length, my eyes very dark, and my father, when referring to our family as a unit, used the term 'the girls', lumping me in with my two sisters. In later years, looking back, I often wondered if he knew that I liked boys more than I liked girls, or that I sometimes wore my sister's clothes when nobody was about. But if he did, he'd never mentioned it.

When I raised my concerns about starting work at 'The Company', my father brushed them aside lightly. He told me that the company ran a scholarship scheme that allowed junior employees to pursue further education, and that nobody cared about the physical attributes of staff members, as long as they followed the dress code during work hours. He made the slightly intriguing comment that I would barely recognize his colleagues if I saw them on their days off. And he pointed out to me that if I got in through the door, I'd have a job for life if I wanted it. I got the definite impression that my fate was effectively sealed; I would be starting as a junior employee, effectively what used to be called an office boy.

A few days before starting, my father took me to a gentleman's outfitters, and spent what I regarded as a small fortune on clothes for me; two suits, a bunch of shirts, ties, waistcoats, trousers, and two pairs of shoes, all of which were a world away from my usual t-shirts, skinny jeans, boots and trainers. As I put the new clothes in my drawers and wardrobe, they seemed to demand their very own space, separate from everything else. I was also provided with an advance copy of the employee's handbook, a large book with a faux leather cover that put me in mind of the Roleplaying rulebooks that one of my friends collected. I did my best to start reading through it, not wanting to disappoint my father, but found myself listlessly flicking through it after just a few minutes.

I stopped flicking when I reached the dress code section; unlike the rest of the book, which was occupied by walls of text in a small, and almost archaic-looking font that I suspected was a deliberate choice to make the whole thing look like some kind of mystical tome of forbidden lore, the dress code was dominated by two full-colour photographs, depicting a male and female employee. For some reason, I felt strangely drawn to the pictures. They were both in their twenties, but somehow ageless. With their straight faced expressions, subtly casual poses, and immaculate outfits, they looked like they could effortlessly fit into a movie about secret agents, or elite assassins.

There was something about them that, try as I might, kept bringing the word 'sexy' into my mind. I kept going back to those pictures during the week, and found myself fantasizing about erotic encounters with them; in store rooms, luxuriously appointed offices, hotel rooms, or (my favourite), in the back of a limousine with leather upholstery and tinted windows, on the way to some kind of high-powered business meeting. Sometimes, I'd be dressed in a sharp suit, pristine white shirt, silk waistcoat and brightly coloured tie, like the male employee. And sometimes, especially if I was fantasizing about the man, I'd be dressed like the woman, in a figured jacket, satin blouse, pencil skirt, jet black opaque tights, and high heels. And as much as I enjoyed these fantasies, I couldn't understand why I was having them. Was I some kind of latent corporate whore? Or did I just have some weird power dressing fetish for businesswear?

As it turned out, the answer to one of those two questions was definitely yes.

The job, as it turned out, was very simple; I fetched mail, I did filing, I retrieved paperwork, requisitioned stationery, and made tea and coffee in industrial quantities. I learned to use the ancient and unpredictable photocopier, and I handed out a never-ending stream of memoranda from upper management. And as strange as it might sound, I began to enjoy it. The work was easy, and I was never too tired by the end of the day, so it didn't negatively affect my life. And the men and women I worked with were all polite, friendly, easy to get on with... and did absolutely nothing to dispel my erotic work fantasies. And very quickly, to my external embarrassment and secret delight, I became my section's mascot. My personality, which in the outside world got me labelled as antisocial, terminally shy, socially awkward and introverted, earned me a reputation as sweet, cute, and adorable. I have no idea why to this day. And just in case you were wondering, those comments came from both male and female co-workers. And yes, I know that a lot of people would find being talked about that way to be patronizing and condescending, but for some strange reason I revelled in it. I loved being the office pet, so to speak. When my line supervisor, Anisha, a tall and almost effortlessly graceful Indian woman, who could have just stepped from the pages of a Cosmopolitan article on professional women, began to nickname me "kitten", I found myself fighting the urge to blush, instead of taking offence. And that feeling only increased as the nickname began to be used by the rest of my section.

But above all, the person whose attention I treasured was Alexander Wray. He was a junior partner within the company. He was in his thirties, tall, lean, with hair so dark I thought it was out of a bottle, blue-grey eyes, and an almost unnatural air of serene calm in everything he did and said. My interactions with him were few and far between, but whenever they occurred... oh boy. If I'd been the type of person to keep a diary, I'd have written about each and every time he spoke to me, smiled at me, or said my name. Looking back, I can absolutely admit that I was in the throes of a huge crush. And even though I kept telling myself to forget it; that he was definitely straight, that he wouldn't be into someone like me, and that It wouldn't do me any good to keep thinking about him, it didn't change a single thing. I would lay in bed at night, and dream about him seducing me in his office, imagining his touch, his kiss, and of him bending me over his desk and giving me the hottest and most insanely erotic ride of my life. I began to fantasize about being his secretary, and sitting on his lap to take notes. And of course, in these fantasies, I was dressed like a secretary, in a satin blouse, tight skirt, seamed nylons, and high heels.

Naturally, that part could only ever be a fantasy. There was no way a company like Archfield & Brewster would ever tolerate a male employee cross-dressing within office hours -- if nothing else, an outfit like that would almost certainly violate their strict professional dress code. But my devious little mind would not be denied, and I reasoned with myself that the dress code only applied to outer clothing; they said nothing about underwear. And after yet another night of adult-rated dreams about being the office pet, I finally hit on a way to make my work life even more enjoyable.

I was earning my own money, and apart from contributing some money to my parents, a very reasonable amount that my father and I had agreed upon, I had a fair amount of disposable income. So I began to order clothes from online for myself, both for work and for my free time. And in among those purchases, I started to order some clothes that would help me live my little fantasies... and decrease my need to raid my sisters' wardrobes.

So, on a day that would otherwise be completely ordinary, I laid out my work clothes; my black suit, white shirt, dark red braces, black waistcoat, matching dark red tie, and black shoes. And I started to get dressed.

First, my underwear. But today, they would be just a little different. I started with the black suspender belt, part of a matching lingerie set that I had ordered. Black silk, with sheer panels, and a little lace trim. Then the matching high cut panties with sheer side panels. Then the stockings. Admittedly, these were a compromise. They weren't the sheer, back-seamed nylons of my dreams -- that would be too risky. So I had settled for some jet black opaque thigh-highs, with a wonderfully sensual velvety feel. And as I hooked the suspender belt together, as I wiggled my tight little bottom into those deliciously snug panties, and as I drew those velvety stockings up my legs, I felt an almost epic sensation of something naughty, sexy, my erotic little secret. I felt complete.

Finally, I put on the matching strapless bandeau bra top, which sat perfectly against my flat-chested boy's body. I had been tempted to leave it off, because I was worried that it might show through my white shirt, but I had tested it out, and when combined with my waistcoat and tie, it was invisible.

With my little dressing ritual out of the way, I proceeded to put on the rest of my clothes, and slip on my shoes. When I was completely dressed, I studied myself in the mirror on my wardrobe door. Perfect. On the outside, I was the model of a young office worker, albeit a slightly anachronistic one. But under those office clothes, I could feel the soft and sensuous material of my new underwear. My secret persona of the office pet was born.

That day at work passed in a blur. I was on top of the world. It didn't even feel like a job. I even relaxed and opened up a little. When Anisha called me kitten again, I jokingly put a little wiggle in my walk as I walked away, causing her to laugh and wonder aloud what she had created, after a feigned cry of "oh my!" while pretending to fan herself with the documents I had handed her. After that, though, I dialled it down a little. There was cute and adorable, and then there was bratty and obnoxiously overconfident, and I knew the difference. My co-workers liked me, and I wanted to keep it that way. But it also added a new sense of curiosity to my now routine daydreams about the other employees. I had been enamoured by how immaculate, how perfect they all looked. Now, I found myself wondering what lay underneath the smart suits, the pressed shirts, the white blouses and fitted skirts -- was there another man with a secret like me? Was Anisha wearing a suspender belt like mine? Did Alexander (and here I had a little tremor of delight at the very thought) have a taste for silky, sensual underwear? It added another layer to my fantasies; that maybe everybody in the building was secretly, sexily, subverting the austere dress code of the venerable company of Archfield & Brewster...

That night, as I got undressed and ready for bed, I felt an almost childlike sense of pleasure. And I found myself looking forward to another day at work in a way that I had never experienced before. And that night, I repeatedly dreamed about being seduced, fondled, caressed, and then slowly and firmly fucked senseless by an unseen male executive. Unseen, but definitely known, because of course, the dream took place in Alexander Wray's office.

Days and weeks passed with the same routine. I expanded my collection of sexy lingerie. My days at work passed with each new day bringing the same sense of enjoyment, and my nights in a rosy glow of erotic dreams. It wasn't all sunshine and roses though; these things do require some compromise. It meant sacrificing some free time to do my own laundry when nobody else was home. But even this had a silver lining. In return for my volunteering to do some laundry, my contribution to the household's finances was reduced -- a token of my mother's gratitude for lessening her housework. At the same time, my parents began helping me with saving money for the day that I would be looking for my own place. This came about because my father was both impressed and proud at the glowing reports he had received about how well I was doing. We had always got on fairly well, but he actually told me that he had come to respect my dedication to the job. He even hinted that he and my mother had plans of chipping in some money for my first holiday, when I finally got around to taking some annual leave. I had almost dropped my thoughts of going to college, and I finally began to understand why my father had been so content to work for the company for so long.

And then, out of the blue, the bombshell hit. And it took me places that I had never dreamed.

It had started as an ordinary day at work. I was engaged in filing documents in the airy space of the converted attic when I got a call to come down to my section. I headed down there, to be asked to help out with bringing some stationery deliveries to the stores and requisitions office. I had done it before, and knew that it involved lifting and carrying boxes, some of which could be quite heavy, so I took off my jacket and hung it over the back of my chair before going down to reception. There was the usual stack of boxes and packages to be taken upstairs. But today, there was a complication; normally, I would use the lift to take the boxes upstairs. But as chance would have it, I saw that the lift was currently out of order. It was blocked off for its regular maintenance, so I would have to carry the boxes up the stairs. Nothing too strenuous, but it would take a few trips. So I rolled up my shirt sleeves, picked up a couple of boxes, and began carrying them up the stairs.

The first two trips passed without incident, but I was a little puffed up and red in the face by the third trip. And as I was carrying the boxes up to the second floor, I misjudged and clipped the top step with my foot. I stumbled, almost fell, and dropped the boxes with a thud. I cursed breathlessly and started to gather the boxes together again. Suddenly, there was a voice from behind me.

"Mind your step, Riley! The company needs you in one piece!"

I almost froze in place. It was Alexander, coming out of the second floor men's bathroom. His tone was good humoured, almost joking, but it almost melted me inside in an instant.

"Yes, Mr. Wray," I replied. "I'm almost finished. Only one more trip to go..."

He paused as I picked the boxes up once more, nodding approvingly. "Good lad... just make sure you finish them, before they finish you!"

I smiled. Another interaction for my memory bank. I turned to carry the boxes to the S&R office.

"Uh, Riley? I hate to fuss, but your shirt's untucked..."

I blinked. He could have told me before I picked the boxes up... There wasn't much I could do about it right at that moment with my hands full. "Yes, Mr. Wray. I'll deal with it as soon as I get to S&R and drop these off..." I murmured

"Don't worry about that. I'll fix it... You don't want to go running into one of the senior partners, looking like that. They're funny that way."

Before I could even figure out what he meant, he walked up behind me. I got a whiff of his aftershave... And then to my absolute surprise, he reached down, and quickly tucked my shirt into my trousers. And for just a second, but a second that seemed to freeze into an eternity of internalized panicked screaming, his fingers caught on the material of my suspender belt!

I froze in terror. My life was literally flashing before my eyes, which were fighting back tears of sheer panic. This was it. I was done for...

And then, in another second, it passed. He gave me a little pat on the arm.

"There you go, all present and correct! And don't push yourself, Riley. Nobody's world is going to end if they have to wait a few more minutes for a box of staples..."

He walked passed me, and our eyes met. I don't know what I was expecting, but the friendly smile and wink that he gave me wasn't it. And then he was gone, heading up the stairs, leaving nothing but the slight trailing scent of aftershave.

It was another minute or so before my legs felt strong enough to finish taking the boxes to their destination. And as soon as the task was completed, I headed to the bathroom. I needed to wash my face and take a moment to compose myself. I was convinced that I had been a total idiot, that I had jeopardized my job, my future, and all for a silly sexual fantasy. But gradually it sank in to me that nothing had happened, and I was safe. But, as I headed back to my section, I told myself that my lingerie wearing would be strictly limited to out of office hours...

The rest of the day began under a cloud of self-recrimination, and I retreated back into myself. It must have been noticeable, because one or two of my co-workers asked if I was feeling alright. Anisha even asked if I was coming down with something, gently lecturing me that coming into work if I was feeling ill wasn't a good idea, and that they'd rather see me take time off to get well, than see me coming into work feeling sick. I started to pull myself together. Their friendly concern and care for my wellbeing warmed me up, and I began to feel my usual self again. I thanked everyone who asked, passing off my down moment as feeling a little light-headed after my exertions. I even joked that maybe I should start going to a gym if carrying a few boxes upstairs had that kind of effect on me. Gradually, I got back to normal, and by the end of the day, I was feeling at peace with the world again.

And then Alexander walked into the office, heading over to my section. I glanced at the clock on the wall. It was a little before five PM. I felt the colour drain from my face once more. So I wasn't home and free. It had only been a stay of execution. The polite little interview at the end of the day, followed by the recommendation to seek employment elsewhere...

I barely heard anything as Alexander stopped to chat with Anisha in his usual friendly way, as if nothing were amiss. A moment later, after a nod from my supervisor, he walked over to me.

"Riley, can I borrow you for a minute?"

I nodded dumbly, looking up at him. He suddenly seemed to be so much taller.

"Excellent. Follow me."

I got up from my chair, buttoning my jacket, preparing myself for the worst. Once more, I was fighting back tears as I followed in his wake. The lift was operational again, and we rode it up to the fourth floor, where the junior and senior partners had their offices. The lift seemed to take an eternity, and the ride up was spent in awkward, burning silence. For his part, Alexander seemed blithely unaware of everything. The man must be an Oscar-worthy actor, I thought to myself.