Today, I’m going to tell you how I became the personal assistant to a magnificent woman, the domineering Boss of a medium-sized company.
I didn’t want to pursue higher education after my high school diploma because I was afraid of getting bored. So, I immediately started looking for work. However, since I didn’t find anything particularly interesting, I just took on a series of odd jobs for two years.
At the end of those two years, I finally found something that caught my interest. So, I decided to apply for an assistant position at a company I liked.
My First Job: Assistant to a Stunning Young Executive
I wanted to work at this company, where I thought that even without a college degree, I might still have a chance to grow.
Indeed, if I assisted someone nice who could teach me a few things and help me develop, it seemed possible.
So, shortly after the interview, which had gone quite well, I received a positive response. They offered me a decent contract: 35 hours a week and 2,000 dollars a month. I’d be a basic assistant, organizing and filing documents or something like that. I was thrilled because I thought I’d lucked out for my first real job.
On my first day, I was invited to go to one of the few offices on the floor that wasn’t open-plan, with walls that weren’t made of glass. You couldn’t see inside.
A woman greeted me. She was stunning and impeccably dressed, almost too well, it seemed odd. I assumed she must be an executive at the company. She looked barely 25 or 26.
Becoming the Assistant to a Young CEO
She let me in and told me to sit down. Her office was spacious and well-decorated, and the chairs at her desk were very comfortable.
She invited me to sit and, then she introduced herself:
- “Hello, I’m Miss Elisabeth Reynolds. I’m the head of this company. So, you’re Simon Perkins, my new assistant, correct?”
- “Uh… yes… yes, that’s right, Miss. I’m delighted to meet you and eager to show you my skills…”
I could hardly believe it. I was going to be the personal assistant to the boss herself. I hadn’t expected that. But it made the salary make more sense. Plus, it worked out perfectly. I couldn’t learn from anyone better than the boss herself. Still, I was surprised by her age.
Sure, it wasn’t a massive company, but it was still fairly impressive. I wondered how she’d managed to build all this in such a short time.
- “Very well, let me explain your duties. You’ll organize and sort all the files you see on those shelves. You’ll also read and respond to my emails and letters, and you’ll manage my appointments. Aside from that, I handle confidential files for the company, so nothing leaves this office. That also means I can’t let just anyone come in. So, you’ll clean my office every morning before I arrive. Then, you’ll handle some typical assistant tasks, like getting my coffee and running certain errands and basic things.”
- “Yes, of course, Miss. That all suits me perfectly.”
My First Days Organizing for Miss Reynolds
So, I started my first day by bringing her a coffee. Then I began looking through all the files in her office. I checked each document, then started sorting them and highlighting the important and urgent ones that needed attention.
On my first day, that was all I did. And yet, I hadn’t even gotten through all the files in the office. There were so many. The next day, I kept at it, maintaining my filing system while also handling emails and appointments.
I found it pretty easy, actually. It just required good organization. Since I was the only one handling the cleaning and tidying, I could decide how to optimize the space for everything.
The days went by quickly. Miss Reynolds wasn’t always there, but I managed just fine. She even complimented my work, my organization, and so on.
I should mention that I was lucky enough to have a desk in a corner of the room, positioned in a way that gave me an unobstructed view of Miss Reynolds’ feet.
Serving My Domineering Boss with Pride
I’m not particularly a foot fetishist. But for her age, she exuded such a sense of power and confidence that I felt happy to serve this magnificent, domineering woman.
So, I sometimes caught myself admiring her gorgeous nylon-clad feet in her heels. I’d imagine how much I’d love to become her heels, to serve her even more.
It was a strange feeling, but I simply wanted to make her life as easy as possible. It was as if she deserved to have everything she wanted while I worked for her. Still, I wasn’t quite sure what more I could do. But I was already proud to be her assistant. I’d even gotten into the habit of thanking her every evening for giving me the opportunity to serve her.
The first time, it might’ve been a bit awkward. But I kept doing it, and each evening, it felt more and more normal to thank her, even when she sent me to make photocopies or fetch her coffee.
One morning, she arrived with a suit in a bag. She asked me to drop it off at the dry cleaner during my lunch break. So, I didn’t eat that day. Plus, when I brought back the receipt, she told me she’d deduct it from my salary.
Massaging My Domineering Boss’s Feet
A few days later, one evening, she took off her heels, complaining that her feet hurt. I seized the opportunity and offered her a foot massage.
At first, she was surprised. Then she pointed out that my job didn’t require me to do that.
But I insisted, saying it would make me happy to relieve her pain and that I couldn’t just sit there doing nothing while she was suffering.
She agreed, but said she had to finish her work. So, I’d have to massage her feet under her desk.
Luckily, her desk was large, so I had enough space to kneel and tend to her.
The smell of her nylon-clad feet was really off-putting. But it meant she’d worked hard that day. So, she clearly deserved a foot massage, even if it was a bit unpleasant for me.
That’s how I ended my day. When she finished her work, she looked at me and said it was very pleasant and that she’d like to do it more often.
I was over the moon when I got home. I didn’t know it yet, but my professional life was about to change.
Serving My Domineering Boss Beyond Duty
The following week, I had the chance to massage Miss Reynolds’ feet four times.
The smell was still unbearable, yet I told myself I was lucky to suffer a little for her. I admit I struggled to understand my feelings. In those moments, it was my “lower half” that took over, and I had a hard time thinking straight.
One evening, Miss Reynolds gave me a shopping list. She specified that it wasn’t for the office but for her personally. So, I’d have to do her shopping after work hours and deliver it to her place.
Once again, I was thrilled and excited.
It was the first time I’d serve her outside my job contract, on my own time.
At the end of the day, I rushed to do the shopping. I slipped the receipt into the bag before heading to her place.
When she opened the door, she simply took the bag from my hands. Then she shut the door in my face after saying,
- “See you tomorrow!”
Redeeming Myself for My Domineering Boss
I was so excited and happy. I’d been worried that her request was a one-off and that she’d felt too awkward about asking me.
But now, it didn’t seem that way. She acted like it was perfectly normal. So maybe I’d get the chance to do it again.
The next day, I was at work on time, of course. As soon as I arrived, my Domineering Boss summoned me to her office.
- “Simon, I get the impression you enjoy working for me…”
- “Uh… well… yes, of course, I’m really delighted… I don’t understand…”
- “Yesterday, when you delivered my groceries, you left the receipt in there? What, you’re not paid enough, is that it? Are you trying to tell me every little errand bothers you?”
- “But… uh… no, not at all, Madame. I… I just forgot the receipt, that’s all… I fully intended to pay for your groceries… I didn’t mean to ask for reimbursement.”
- “I see… Still, that was rather rude, don’t you think? But you seem remorseful. So, I’ll tell you how to make it up to me. You do want to make it up to me, don’t you?”
- “Yes… yes, of course, I’d like to know what I can do, please?”
- “Good. During your lunch break, you’ll go buy supplies to clean and polish my boots, understood? Take a good look at them to know what you’ll need.”
- “I see. Thank you so much, Miss, for giving me the chance to redeem myself. I’ll make sure not to offend you again in the future.”
- “Good. Now get to work.”
Polishing Boots for My Domineering Boss
So, I bought supplies to polish her boots.
When I got back to the office, she ordered me to take care of it while she was still wearing them. I would’ve been more comfortable if she’d taken them off.
But she was the domineering Boss, and she decided what was best. So, I went back under the desk—I was used to it by then. I started cleaning her boots as carefully as possible so as not to disturb her.
I spent the rest of the day on it.
When I finally finished, she looked at the result and said it wasn’t bad for a first try. But I’d taken far too long. In the future, I’d need to learn to do it much faster.
Of course, I thanked my domineering Boss before heading home, feeling truly happy…
I got more chances to massage her feet, polish her boots, or run her errands many times over.
I think that ever since I became the assistant to this magnificent dominatrix, I’ve been the luckiest man in the world…
To be continued.
