In my late twenties, I used to work part time as both a male stripper and a professional escort. The vast majority of the time, the professional escort duties turned out to be at least interesting, and often fun, because I was spending time with highly accomplished women. On occasion -- perhaps only ten percent of the time -- it might lead to a hot encounter. These are the times I intend to chronicle for Literotica. Another ten percent of the time, the escort duties were a disaster, perhaps because the woman I was escorting was difficult to work with, or the event I was attending with her was boring or somehow offensive. I really earned my fee during these times. This story is about a gig that could have been a disaster but turned out alright in the end.
My boss had only told me that I was escorting an older woman to a company holiday party, which had turned into a retirement party for her boss. The client was angling to be considered for the big job, and wanted an escort so she was seen as more "well-rounded" for the job, whatever that meant. I arrived at "Betty's" house well before the scheduled beginning time, to discuss how she wanted to present us to the group. Unlike most clients, she had already gone to the main office (actually, just a little desk in a business center) had the contract explained to her, and signed it. All we should need to do, in theory, was to agree on how we "met." We usually referred to this as our "cover," though it was not as sneaky or secretive as it probably sounds.
I arrived at about 6:00 pm, and rang the doorbell. The client opened the door after about ten seconds. Of course, at this point, I am always smiles, though the scowl on the woman who opened the door tested my mouth muscles. I widened my smile.
"Good evening," I began. "I'm Wade Hunter from Eleganza,…"
"I know who you are," she snapped. She stepped aside. "Come in."
I entered the front room of a beautiful townhouse, and turned to greet her again. The client was a woman of 45 or so, with very average looks, neither particularly attractive nor unattractive. She was dressed in an elegantly simple iridescent blue dress which accented her figure perfectly. Before I could say or do anything else, she spoke again, and with great authority.
"Look, we should get this straight from the beginning. We will be attending a holiday and retirement party with my coworkers, and I intend for people to see me as capable of taking over our division when the retirement becomes effective. "One of the things I need to show them is my,…" here she paused. "Interpersonal ability." She looked up. "That's where you come in." I decided to wait, rather than respond. Spending your professional life as a social worker, giving people time to collect their thoughts often comes in handy for me. She looked me right in the eyes with a fierceness that gave me chills. "I expect nothing -- nothing -- to prevent me from getting that position. Do I make myself clear?"
I nodded. "You do." Still smiling slightly, I added, "Anything else I need to know before we go?" She stared at me.
"Such as?"
"Oh, people I should make it a point to talk to, folks I should probably avoid, or….
She waved her hand dismissively. "That's not your concern. Just do what I tell you to, and stay close to me." My smile was getting more difficult to maintain. I looked up and fixed her with a polite, but strong stare.
"I'm having difficulty understanding why you even need an escort. If all you want me to do is stay next to you and do very little, you could have saved your money." I could tell she was trying to maintain her cool, but I had obviously hit a button. She stared at me again.
"Look, I want this job, and I deserve it. The problem is…, oh why am I telling you this anyway?" She collected herself, then continued. "The problem is people don't believe I relate well to others. You are supposed to be one of the best escorts from your service. I'm told that you're both charming and intelligent." (Since that wasn't meant as a compliment, I didn't thank her.) "I simply want you there to show that I can relate to people, so that won't be an obstacle to my getting the job."
I nodded my head. "I see." Actually, what I saw was a rather pathetic attempt by someone who didn't know a whole lot about relating to people. It certainly didn't make sense to me, but I'm not the client. I turned toward the door.
"Two cars?"
"Yes," she said. "We'll meet at the Anderson Hotel parking garage." Having been given my orders, I left the house, and went to my car. I knew the hotel well, and got there in about 15 minutes. I stayed in my car until I saw her emerge, then I quickly met up with her at the elevator.
"I almost forgot," I said. "What's our cover -- meaning how did we come to be here this evening?" She scowled.
"Is that important?"
"It is if people ask, which they often do will." I tried to moderate my tone so I didn't sound like a teacher. I smiled. "It's better to be prepared for these things in case they do come up." She hesitated.
"Well…alright. How about a 'friend of a friend?'"
"That generally works well," I said. "Shall we say that your friend went to school with you?"
"Fine," she said, almost angry. We went up to the mezzanine of the hotel to the room that had been reserved for the party. As we entered, I quickly tried to assess our surroundings. I noticed that people looked in our direction, and seemed to watch Betty as she entered. I also noticed that some of the conversation stopped when they saw her. Betty handled several introductions quickly, without taking much time for small talk with any person except for the boss who was retiring. After I was introduced to the boss and his wife, Betty looked at me and said,
"Wade. Scotch and soda." Then, she quickly returned to her conversation. I knew what she meant, but certainly didn't appreciate the tone of her demand. As I smiled and turned to leave, I could see the boss' wife shake her head almost imperceptibly. Obviously, she had noticed Betty's behavior, too, and was probably more accustomed to seeing it. Things did not bode well for Betty and this job, I gathered, if my assessment of her interpersonal skills proved accurate. I returned with her drink, preferring not to get one for myself, and tried to find a way to get into the conversation. It was mostly about business -- finance stuff -- which I have little interest or expertise in. I decided to try to engage the boss' wife.
"Retirement is a big change," I began. "Have you developed any specific plans for it?" As I finished my question, I could see Betty shoot me a glance as if to say, "What are you doing?" I continued to chat with the boss' wife, but when she answered a question with a short answer, I let things go. I was about to pick up the conversation again, when Betty said, "Wade. Come." I had never had a dog, and didn't particularly enjoy being treated like one. Betty led me to another group, some of whom I had been introduced to when we arrived. Betty introduced me to the newcomers, one of whom asked me,
"How do you know Betty?"
"He's a friend of a friend," Betty shot back. The woman continued.
"And what do you do -- I meant, you're not with the company, right?"
"Right." I looked briefly at Betty, knowing she wouldn't have a clue as to what to say to that. Since she didn't stop me, I answered,
"I'm a Social Worker -- and a full time graduate student." I smiled, perhaps a deferential smile, since I could sense that many of these people were very well-heeled, which I was likely never to be. The woman I was speaking to smiled and said,
"It's nice that you two met -- Betty is so involved in work, it'll be good for her to spend time with somebody who focuses so much on people and their problems." At this, Betty bristled, ever so slightly. The conversation left us for a bit, then we walked to a different group. Once again, Betty did her "Wade. Scotch and soda," routine. This was getting on my nerves. With every person we talked to (or I tried to talk to, since she always took over or shortened the conversation) I felt like I was being ordered around in a very embarrassing way. My ego, healthy as it was, was really being tested, and my skin was just thin enough that I was approaching the boiling point. Worse still, I noticed that the woman who had asked me about my job came over two more times before dinner, and tried to engage me in conversation, only to have Betty steer us away. After the second time, it was obvious that the woman was doing this deliberately, because she would return afterwards to her husband, and titter. So now I'm being treated like a kid, and people are actually getting off on it.
