
My wild, unexpected vacation started benignly enough. I was contacted by an old, and now fairly distant, family friend who said he had a summer work opportunity for me. It was a little unusual, he cautioned me, but a very rare and valuable opportunity for a college student strapped for cash. It would allow me to travel all over the world – all the while getting paid handsomely. Needless to say, my interest was piqued immediately.
This family acquaintanace, Eric, went on to explain that he had an old friend who loved to travel the world but hated traveling. And by this confusing statement he meant that this friend, Elizabeth, loved to see the world, but hated getting there. She hated airports, she hated hotels (well, she actually liked hotels, but she hated getting to them, checking in, booking reservations, etc), she hated taxis, she hated the whole hassel of having to plan things and then make sure that she got to all the right places at the right times with the right items. Basically, Eric told me, I would be taking care of all the unpleasantness of traveling, and in return she would pay me well and would pay my way as well – because, in order to take care of everything for her, I had to be with her every step of the way.
Your responsibilities, he said, will include just about everything. You will plan her flights, lodging, transportation, entertainment. According to her wishes and directions, of course. She will tell you where she wants to go, when, and what she wants to do when she gets there – in general terms. And you have to make the precise plans. The day of the initial flight you are to inform her when you will pick her up, then drive to her house in your car. You will then drive her to the airport in her car, making arrangements for the person of her choice to pick the car up later in the day.
At the airport, you are to be responsible for her bags – as well as yours – at all times, and you are to conduct her to the check-in counter, through security (make sure she knows what she can and can’t put in her checked luggage), to the gate and onto the plane. She will be flying first class while you will be flying coach – but before you take your seat make sure she is comfortably installed, with her carry-on baggage where she can easily reach it.
Once at your destination, you are to conduct her off the plane, through customs, baggage claim, etc, and make the necessary currency exchange. Then guide her to the hotel shuttle or to a taxi. You will have to give the taxi the necessary directions to the hotel, where you will check in for her. You will have two separate rooms, of course, but yours must be immediately adjacent to hers, so she can call for you at any time (she doesn’t want to have to figure out how to use the hotel phone to call your room). Oh, and keep a spare room key in case she loses hers or leaves it in her room.
Eric went on and on like this for a long time. It took about half an hour for him to fully describe what the job would entail. I was stunned by the end of it. When he asked me if I had any questions for him, I didn’t really know where to begin – though I was brimming with curiosity.
“Is all this really necessary?” I asked.
“Absolutely,” Eric responded. She has a deep passion for seeing the world, but really can’t handle the stress of modern travel. You’re to take care of all that for her, to allow her to do experience what would otherwise be impossible.” I thought about this for a moment. It sounded plausible enough. I mean, I hate the hassel of travel too, and I could imagine there were people for whom it was just too much to handle. An issue that had been brewing in my mind for a while came out next.
“Isn’t it a little weird that she’s a woman and wants a guy for a travelling companion?”
“Good question. I’m glad you asked, as it is bound to come up from time to time. She is a very self-motivated, talented, and successful woman. She’s very prominent and well-known in her field. As such, she has experienced the full range of male chauvinism in society, business, politics, you name it. She knows that men get around the world easier than women. And she knows as well that, due to the nature of the tasks you will be performing for her, she could never get an adult to travel with her. She believes that if she hired a young woman the two of them would be taken advantage of, perhaps dangerously so. She perfers a young man because men are shown more respect – especially in the countries whe wants to visit.”
Again, I thought it over. It sounded quite plausible, as before. “So what’s in it for me, again?”
“You will be paid $500 for each day of the trip. Of course, this will require some up-front planning on your part, but still, that’s a fair amount of money. Over the course of the summer, you will likely make two or three trips, each of ten days or so. All in all, it’s a fair chunk of change. And your way will be paid for and you will get to visit the same places as her. A starving student could hardly ask for a better opportunity. Of course, she expects everything to be taken care of, so you’ll have to plan carefully and be responsible at all times.”
I couldn’t argue with his assessment. I could make as much as $15,000 this summer – and see the world at the same time. But still, something about the offer seemed weird. “Tell me more about this Elizabeth,” I asked.
Eric went on to tell me that she was a businesswoman and had built a small empire in the foods business, starting from nothing at all. She was very wealthy, but also ver eccentric. I found out she was middle-aged (Eric would not divulge her exact age), so she had made her fortune quickly. Eric said she had asked him to find a suitable travel companion/manager/guide, and that he had recommended me.
“After seeing a picture of you, she was sold. She absolutely insisted I be the one.”
This made me a little uneasy. Eric seemed to recognize that he had made a mistake in saying that last bit, and quickly backtracked. “Of course, she thought you looked mature, capable, responsible. You can tell from people’s facebook profiles these days who’s grown up and who isn’t.”
I was a little relieved, but not totally. I told him I’d think about the offer and get back to him. But to be honest, it was too good to be true. I would visit the world, get paid well, and have the chance to network with a very famous, successful businesswoman. As an aspiring businessman myself, it was truly a dream come true. I got in touch with Eric the next day and told him I was on board.
I won’t go through all the details of the trip planning, as that would bore you and has no relevance to the story, after all. Suffice it to say that I made all the necessary arrangements, according to Elizabeth’s requests (I spoke with her by phone several times and exchanged emails), and the first leg of our journey went off without hitch. We landed in Rio De Janeiro and arrived at the hotel (the Hilton) seamlessly.
Elizabeth herself was eccentric, but not as snoody or aristocratic as I had feared. She was actually quite beautiful: slim, in her mid-40s probably, with beautiful, long brown hair. She didn’t seem to fit the stereotype of the masculine self-made business woman, competing in the world of men and having to work twice as hard for the same amount of respect and success as her male peers. I mean, she had long hair, wasn’t overly type-A, and wasn’t paranoid about exuding feminine charm. She could reveal a certain anger and disdain for men, though, especially when she noticed a difference in treatment due to gender, or a gendered social norm. She would become frosty, haughty, and commanding at such moments. But I took them in stride and didn’t complain. She was right, after all, about the way society favors men in many cases.
I have to admit, it was a little humiliating to be her personal servant. Carrying her bags, especially, made me feel submissive and subordinated. But I thought maybe women have been feeling this way for ages. Am I above feeling the same? And I was getting paid well, I told myself. So I endured it.
Except I need mention one thing. Before we left (a week or so before), Eric brought over a package, sealed, with my name on it. He said there was something inside for me from Elizabeth, but that he had no idea what it was. Curious, I opened it (not in his presence, of course), only to find a simple note. A list, really. It said, “Dear Matthew, please find enclosed a few items you will need during our trip. Please bring them with you – Elizabeth.”
I pulled the items out of the package. There were several. They were soft, very colorful, and small. I unfolded the first, which was bright, bright blue, to discover a pair of underwear. I was surprised and somewhat suspicious. They were boxers, though based on the type of material and the size of them in my hands I could tell they probably fit pretty tight. A piece of paper fluttered to the ground as I held the blue boxers up. I picked it up and read the hand-written message scrawled across it: “I love to swim, but I’m especially self-conscious at pools, particularly hotel pools. I never know when they’re open, when they close, who else might be using them, etc. So since we’ll be spending a lot of time at the pool, I thought I’d buy you some swimwear. Of course, they’re usable as ordinary underwear as well.”
Again, the explanation seemed to make sense, but was definitely a little weird and unusual. I looked at the other items in the package. They were either like the blue boxers (red, black, white), or else much skimpier – speedos. The speedos were black, yellow, and red. Curious, I stripped naked and slipped the blue boxers on. They fit perfectly, though I wasn’t really prepared for the way they fit. I mean, to say they weren’t loose-fitting boxers would be a huge understatement. They hugged my hips, butt and junk so snuggly that they felt like a second skin. Looking in the mirror, I realized they really boxers, either. They actually covered less than your average briefs: they barely covered my butt in back. Up front, they had a special pouch for my junk, which highlighted my manhood in a way that made me blush just looking at myself in the mirror. The ‘legs’ were very short and did little more than connect the front pouch to the back.
Like I said, looking at myself in the mirror made me blush. I mean, I felt naked – and perhaps more embarrassed than if I actually were. Stripping off my blue ‘boxers’, I slipped into the yellow speedo. Well, I guess I should add here that it wasn’t really a speedo – it was underwear. A real piece of swimwear, a real speedo (I know, I’ve owned one), feels a little bit thick, rubbery, and water-proof. This felt thin, silky, form-fitting. It felt like underwear. Only it was as skimpy as a speedo. No, it was actually quite a bit skimpier. Or, at least, it felt skimpier when I put it on and looked into the mirror.
Two things stood out. First, it fit quite low across my hips – so low that my pubic hair risked showing – and the material connecting the front pouch to the back was maybe a centimeter high – scarecely more than a strap winding around my waste. Second, the thinness and suppleness of the fabric meant that my junk hung fairly low below the wasteline of the speedo, and the form at least was quite apparent. I could only imagine what it would look like after it got wet.
I honestly couldn’t believe that she meant these for swimwear. Yet that’s what the note said. I read it several times to be sure. After a moment of uncomfortable, embarrassed thought, imagining myself thus clad walking around the pool collecting stares, I decided that, while I appreciated the gifts and the thought that went into them, she must have assumed I was much more comfortable with my body than I really was and vowed to bring my own swim suit.
Then I remembered that she has specifically requested I bring the package’s contents with me. Oh well, I thought. I’ll just bring both and wear my swim suit when we go to the pool. Surely she won’t insist I humiliate myself like that. I couldn’t imagine how that made me seem more competent and capable. She would surely let me wear what I wanted, I told myself. Why wouldn’t she?
Anyway, back to the story. We check in at the Hilton and take the elevator to the very top. I had been looking forward to this since I booked the room: it was a suite with two bedrooms, a kitchen, and living room. The view of the bay and the city was extraordinary. I took Elizabeth’s bags into her room, then dropped mine off in mine. When I came back to the living room, I could tell that something had changed. The air felt different. Elizabeth looked different, only she hadn’t changed clothes or anything. She hadn’t had time to. There was something about her posture, her eyes, that was suddenly not the fatigued, stressed traveller. The room felt frosty.
Elizabeth looked straigth at me and spoke. “I’m going to take a shower, I feel like crap. Here are your instructions – when I come back I expect they will all be complete.” She walked two steps to the coffee table next to the sofas and laid a sheet of paper down. Then she turned, looked at me imperiously, and strode into her room, closing and locking the door behind her.
I was shocked. She had been so quiet, helpless even, the whole trip until now. She had let me lead at every point. Now she had an air of command that was the complete opposite – yet, coming from this new woman who had just emerged, felt completely natural. Nervous, I walked to the coffee table and picked up the sheet of paper, wondering what I would find.
“Matt, here are your first orders. I expect them to be promptly and exactly obeyed. They are to be done in order.
1. Change into one of the swimsuits I gave you and told you to bring – your choice which
2. Turn on all the lights, lamps, etc, and open the the window drapes
3. Make a pot of coffee and have a hot cup waiting for me on the coffee table”
What the hell? I thought. What was going on?!