How I Became An Executive Assistant

by Sarah Dechand

  

It had been a while since I had thought of Emily, but there she was, right in front of me, in DuPont Circle, looking almost exactly the same as she had when we went out a decade ago. Well, a little bit of gray in her hair, but her skin was still smooth, and eyes bright. And she seemed happy to see me. So I stopped – and it was one of those awkward moments, where I wasn't sure whether to shake her hand or give her a kiss hello. The chaste handshake won out. It must have been because of the way we ended things – lots of tension.

"David Russel, it's great to see again! What are you doing here?" OK, some warmth here, despite the handshake.

"Well I always walk through DuPont Circle on my way to work. Why haven't I seen you here before?"

"I'm surprised you haven't. My office is just down 18^th Street here," she said.

"I'm over on 23^rd, but I walk to work."

"So that's why you've been able to keep your girlish figure." She laughed.

While I spat out the expected response – "You haven't done so bad yourself!" – which was true, she looked great, my pulse jumped about 50 beats. That had been one of our games when we went out. She'd dressed me in her clothes a few times, and I had to admit, when she did, those were the hottest sexual experiences of my life. And I told her they were hot, and asked for more. The relationship had really made an impression on me, and left me with years of lingering daydreams and fantasies. So I could read a few things into her "compliment." Like – what have you got on under your pants? Wouldn't surprise me if you were wearing panties. Does your girlfriend know? Does anyone else know?

"Not bad considering I live a sedentary suburban life – husband, two great kids, two car garage…"

"You really do look great, Emily. So how's work?"

It turned out that Emily was going through a hard time at work – she'd just lost her 3^rd assistant in as many years, and no replacement was in sight. She complained that it took a great deal of effort to train someone new, and that it was discouraging to begin again. So I suggested that she hire me to be her assistant.

"You're kidding, right?" was her response. But I also saw something unmistakable in her expression. She knew that she'd enjoy having me around to tease, and hold captive, the way she used to.

So I told her about my life, and how lately, I'd been feeling a bit fed up with the hard driving, over the top, one-upsmanship that characterized my line of work. I was looking to slow down, work fewer hours, and enjoy things a bit more.

"So you'd actually work for ME?" She asked, sort of like a kid who knows that the big present under the tree is for her.

I had to admit that I would. Working for Emily would be my biggest challenge in some ways, but at the same time, one of the most idiotic and weirdly indulgent things I could possibly do with my life.

"For you, yes. But not for anybody."

"OK then. Come with me to the office, and we'll see if you still think it's a good idea."

Emily had risen to become the senior vice-president of her company. In fact, she basically ran the place, with the help of the CFO. The President was off on his yacht most of the time, and didn't give a fig about what happened at the business, so long as there was a steady profit. Emily's clients were a mix of architects, interior designers, contractors, and companies relocating or upgrading their offices. There were two parts to the business: sales, and service, and Emily excelled at both. The help she needed was essentially an executive assistant, someone to make sure that she was prepared to face each busy and challenging day.

"I could really help you with that, you know." I said, remembering the delirious pleasure I had taken in submitting to this energetic and powerful woman.

"But do you think you could handle the reality of being my assistant, David? I remember how domineering you could be in the office. Here, you'd have to do it my way, no ifs, ands, or buts."

"That was years ago. I've mellowed out. Besides, I've proven all that anyone needs to prove in my line of work." It was true. I'd closed some of the biggest deals in D.C., and had no real need to show that I could run with the big boys. "I used to like playing that game, but I'm really ready to give it up."

"It's true you'd have a leg up on any of the other applicants. I know that you at least understand the business. That'll be a big help." She said.

"Well, yes. But what I'm interested in now is different. I really just want to be helpful to you."

"You're serious, aren't you?"

"I think that I am. Some guys my age and in my situation go out and buy themselves a Porsche, but I'm looking at something a little less show-off-y." We both laughed at my joke. A good sign.

"Tell you what. I'll give you a couple days to decide. The salary's 45, but we have a little commission structure that we share when we score a big job. You could make maybe 55 or 60 in a good year. You should also know that there's not much of a future in the job, no real chance to advance to an executive position, but I somehow don't think it's going to be a consideration for you."

The offer was made, so I thought about it long and hard over the next couple of days. On the one hand, she'd only hinted about reviving our relationship, but on the other, the hints were strong and sure. The thing was, she had a family, and there was no way that she'd break it up on my account. But on the other hand, it might be possible to keep it simmering under the surface, keep it all in my head. Maybe she thought the same. Two days later, I called her up, and accepted, on the condition that I needed to bring some closure to my business.

So I tied up the loose ends, gave notice to my partners, (which made them sad, since they had to buy me out,) and took my fat check to the bank. A free man, at last.

A month later, I stood at the entrance to Emily's office, my heart in my throat, waiting to begin my new job. I walked in, and told Jennifer, the receptionist that I was here to start working. She called for Emily, who came out escorted me back to her office.

"I'm glad you decided to take this job, David, but I've worried about a few things. So I - "

"Don't worry, Emily, my interest in this job is strictly professional." I interjected.

"Well that's good. But don't ever cut me off in conversation again. We will in fact be keeping things very strictly professional here, and to make sure, I want to ask you to sign this employment agreement. It's basically the same one we use with all of our employees, but I've added a couple of clauses that (ahem) speak to our prior experience working together, and to our dating history. So take a minute and read through. I'm going to take care of a few details, but please feel free to ask any questions."

I studied the agreement, and it seemed OK. There was nothing unreasonable in it. There was the structure of the office, chain of command, and reporting structure, which mostly led back to Emily. There was the section on termination, which included a non-compete clause, basically to make sure that I couldn't leave the company to join a competitor, and take business with me. There were office policies, which seemed perfectly reasonable – office hours, expectations for office attire, attendance at meetings, and required training. But I just couldn't see anything special about the agreement, so I asked her – what were the special clauses.

It turned out that the only "special" clauses were those that clarified the enforcement of office policies. Basically, this contract reinforced that she, Emily, would have the final say regarding office policies, and that failure to comply with the policies, essentially her wishes, was grounds for dismissal. So I signed the contract, much to her satisfaction.

Emily showed me my new desk, right outside her office – so she could keep an eye on me – she joked, and gave me the tour, and introduced me around to the others in the office. The people there seemed like a good crew, and they seemed to like Emily. One guy even commented that it was about time that Emily got some more seasoned help in, considering the bad outcomes of her previous assistants. Even so I began to get a good feeling about the move.

By this time, it was 10 o'clock, and Emily had to see a client, but she promised to be back for lunch. She had blocked out the entire afternoon to get me started with the work. In the mean time, I got busy with setting myself up at my new desk.

Lunchtime arrived quickly, and we went out together to eat. It was dreamy to be in her company once again, and I exercised gentlemanly care with her as we entered the restaurant and sat down to order, which she didn't really seem to appreciate. She seemed more intent on being assertive, and in control.

"So David. Do you remember the part of your contract about expectations for office attire?" Emily was smiling as she said this.

"Yes," I replied, "the requirement is to look professional -"

"In the judgment of the SVP, right?"

"Yes, in your judgment." I said, my expectations suddenly raised.

"Well, I'm going to get right to the point," she said.

I felt literally like holding my breath.

"As you may have suspected," she continued, "there is a little more to this than just me being your boss. We shared something that was extremely rewarding those years ago, even though it didn't work out. But this time, it can. We now have a situation where I can safely and comfortably control you, and you can freely and wholly submit. While I have my family now, and a great husband to go home to, we can keep this completely in the context of the office.

"So I'm going to lay it out for you, plain and simple. What you are wearing is not considered professional."

"It's not?" I was wearing a grey suit, with a blue shirt, and a patterned tie.

"No. It's not. As long as you work for me, you'll follow a more feminine definition of professional."

"You want me to wear a dress to work?"

"Nope. You can wear pants. They just have to be women's pants."

"Are you serious?" I was astonished. On the one hand, this was something I had fantasized about, and my physical reaction was quite impressive. On the other, the prospect of actually dressing like a woman for work was scary.

"You know that's what you want. That's why this whole thing works. I get competent and capable help to ease my life, and you get your weird fantasy. It also doesn't hurt that I like to be in control."

"But how…" I started,

"We're going to do a little shopping this afternoon, and help get you set up. Tomorrow you can begin in the office."

Since we had only a few hours, the shopping was quick and to the point. Emily decided what I should buy, and I bought what she picked out. There were mostly slacks and blouses, but also a couple of skirts, and of course a good supply of underwear, including some all-in-one's, waist cinchers, and other shapewear. Emily said that I'd need it for my "girlish figure." There was a quick stop to pick out a few pairs of "sensible" shoes. The heels weren't high – only a couple of inches. Our last stop was the make-up counter, where Emily made a big show of finding "my colors" for me.

At 5 o'clock, we were finally done. I was loaded down with shopping bags, and Emily hailed a cab for me. After loading up the trunk, Emily handed me a slip of paper as she put me into the back seat. It read: "You have a 6 PM appointment with Lisa at the xxx spa on xx street. Don't be late. She knows what to do. PS, you might want to change out of your suit."

So I showed up at this spa for my appointment with Lisa, a small but curvaceous chipmunk-like woman. She greeted me in a businesslike way - "So, you're Emily's new assistant. She's scheduled you for an all-over waxing, a facial, ear piercing, manicure, and pedicure, as well as a quick cut and style. It's going to take until at least 10 to finish up all of that. Are you sure you want to go through with it?" I said that yes I did want to go through with it, and Lisa led me to the back, told me to take off my clothes, and gave me a bathrobe to wear for the treatment.

3 hours later, I was well-waxed, plucked, and painted, and on my way to have my hair cut. Lisa had been very loquacious the whole time, saying things like "sweetie, this might hurt a bit, but you'll feel much better when it's over," and "hold still cutie, that's it." Now she was going on about the haircut – "You know that Emily's instructed me to give you a very feminine cut. The rest of this stuff you can hide pretty easily, but your hair – that's another story." I told her I'd gone this far, so she might as well complete the job.

As Lisa styled my hair into a neat, short, but feminine wedge cut, I couldn't help but think that I was totally nuts to be doing this. But on the other hand, the lure of it was strong. I was enjoying Lisa's attention, and she was being very polite by "not noticing" my obvious excitement at the treatment. I felt bad – putting her on the spot this way. She was, after all, a beauty professional, not a sex professional. When it came time to settle up, I mentioned it to her, giving her my thanks and a large tip. She seemed to appreciate it, and gave me, complements of the house, a little leather bag, which contained some bath salts and aromatherapy, saying, "You should probably soak in the tub when you get home. You've got a big day ahead of you tomorrow."

Walking across DuPont Circle back to my apartment – just another queenie looking guy in this part of town, I felt remarkably at ease. Tomorrow, I would go to work dressed as a woman, and I would go to work with only Emily and her responsibilities to think about. I returned home, and unpacked the shopping, hanging it up in my closet.

It was then that I noticed some peculiar things about my new wardrobe. First, none of the blouses buttoned in front. Emily had picked soft, silky blouses for me which all buttoned in the back. Second, none of the pants fastened in the front. They all had side or rear zippers. Finally, she had not picked any jackets for me to wear at all. It seemed like Emily definitely had a look in mind for me when she chose my wardrobe. The thought of coming to work, dressed in accordance with Emily's wishes, made my head spin.

After a good soak, during which I delighted in my newly smooth body, I set my alarm for 6, since I didn't want to be late, and I wanted to look my best for Emily. After showering and eating a light breakfast, I began by putting on my underwear – an all-in-one slightly padded bodyshaper and a pair of sheer pantyhose. Then I picked a pair of wide-legged dark lavender slacks, and a pink blouse with small dark dots, which Emily had pointed out would match just about any dark color pants or skirt. I put on some light make-up, just enough to cover my beard, (which fortunately was pretty light), and took some time to try and get my hair to behave, which I did with some success. I left with ample time to make it to the office.

Emily was beaming as I entered in my very strictly professional outfit. "You look just delicious," she said. For my part, I smiled and reminded her to keep it strictly professional. "Oh yes. Very strict." She said. The rest of the day was all business, but we did work side by side, as Emily introduced me to the various tasks I'd have to do. The others in the office, it seems, had been briefed by Emily, and treated me just like a normal human being. Imagine that.

Emily's presence, along with the feeling of the high-waisted pants and the soft turtleneck of the blouse kept me fairly well aroused throughout the day, though you'd never notice under the smooth front of the pants, thanks to the pantyhose and bodyshaper. In fact, that was what Emily seemed to like. She surely knew that the whole experience was driving me completely wild, but there was nothing that I could do. I caught her looking at my perfectly smooth crotch once, but there was nothing I could say.

At the end of the day, she instructed me to wear my houndstooth trousers with an appropriately matching blouse and shoes tomorrow, and I left burning with anticipation.

This continued day after day. For my part, I was overjoyed to have an outlet, though an imperfect one (ideally, we would be sexual partners as well as collaborators in this unusual business relationship.) I worked very hard to give Emily the upper hand in her business dealings. For her part, Emily knew how to push my buttons, and did so frequently, complementing me on my blouses, and dictating my wardrobe.

Occasionally, she would have me wear a skirt or dress to work for a client meetings, but mostly, she kept me in pants and blouse outfits. She claimed it was for my own comfort, but truthfully, the skirts and dresses were more comfortable, and less confining than the pants. During one particularly unforgiving and humid August, when Washington is like a hot bowl of pea soup, Emily made a big show of unbuttoning the top two buttons of her short sleeved blouse in the office, surely delighting in the fact that my full sleeved blouse buttoned in the back, and I would not be able to enjoy the same kind of relief.

So Emily did her part to make me happy, as much as I did for her. I worked with Emily for about 6 years, never got a raise, and never got a promotion, never once wore a jacket to the office, and never once wore anything that fastened in front. My wardrobe has, of course, become more diverse, and my personal life is holding some real promise, now that I've decided to go all the way and become a real woman. I'm thinking of getting back into real estate, but this time in a more personal, residential context, and the future has never looked brighter.

The end.

  

  

  

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