Lemonade Out of Lemons

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.

We were finally directed to the dinner tables, and as Betty steered us toward a particular table, I managed to get myself a seat next to a male spouse of a coworker, so I wouldn't have to deal with another woman who would somehow ignite something in Betty, who I had pretty much properly assessed as a ball-busting, impersonal tyrant, who people actually enjoyed seeing blow up. We sat down, and dinner went about the same. Even when I talked to this guy on my left (who I thought was kind of interesting) she kept insinuating herself in the conversation, perhaps to impress him. By the time we were being served the entree, I had had it. Betty pointed at the gravy and said,

"Wade. Gravy." As I passed it to her, I noticed the boss' wife giving me a sympathetic look. That was it.

"Please excuse me," I said, rising. Betty was on me like white on rice.

"Where are you going?" she asked. I responded slowly.

"Little boys' room. Excuse me." I rose, pushed in my chair, and walked off. I didn't really need to use the restroom, and instead, I went down the escalator to the first floor and found a payphone. I quickly called my boss at her home office number before I blew a gasket. My boss picked up on the second ring.

"Eleganza Professionals, may I help you?"

"Leesa. Wade."

"Hey, Wade. Are you working?" I smiled slightly, which she couldn't see over the phone.

"Oh, I'm working alright." She got it.

"Shit," she began. "I didn't want to tell you beforehand, but I had a feeling this was going to a tough one." Some might have gotten pissed that Leesa hadn't let on that she thought I was going to be working for a bitch, but she has often been wrong about clients, and unless she is absolutely sure, she doesn't try to bias the escorts' opinions about clients. I explained quickly how the evening had gone so far, to a few "Ums," and "Oh boys," that showed me she was listening and understanding. When I finished, she was clear.

"You don't have to put up with that," she said. "I'm going to put the full charge on her credit card now, and if you want to leave, I'll back you." I sighed.

"That's what I was thinking," I said. "I'll try to make it as smooth as possible, though knowing how this lady operates, I'm sure you'll be hearing from her." Leesa laughed.

"No shit."

I hung up the phone, feeling relieved, and a little tired, from being so nice to this witch all night. I returned to the meeting room, and stood at the door to get Betty's attention. I waved her over, and while obviously annoyed, she excused herself from the table and came over. She was exasperated.

"What is it?" she demanded. I faced her calmly.

"I just wanted you to know that I'm done for the night," I said. "I'm sure you'll do well without me." She pushed hard against my chest.

"The hell you are!" She turned her head toward the dinner tables, then led me into the hallway.

"You're not going anywhere, I paid for you for the whole night." That got me.

"You didn't pay me to be abused by you. Look lady, if you want somebody to follow you around like a puppy, you got the wrong guy. I'm done." I paused, then quickly added,

"We can do this the hard way or the easy way. I can…"

"How dare you!" she snapped. She raised her arm to strike, but I was faster, and put up my hand, waiting to block. She lowered her arm.

"Now," I said, feeling more empowered than I had all night. "I can walk out right now, or we can return to the table, and I can excuse myself for some lame excuse like an exam or something. Your choice." She looked at me, and for the first time, I think I saw fear in them.

"But, but you can't! I need you here!" Seeing her distress, the Social Worker in me kicked in, however reluctantly.

"Betty," I began. "The whole idea of my coming here was for you to have a better shot at the job, but," here I shook my head. "But if you could read the faces and body language of the people in that room, you'd know that you've done nothing to make that possible. In fact, you've treated me so horribly, that it may have hurt you." She stared at me, until I began to see her eyes watering. She blinked quickly and cleared her throat, so I wouldn't see.

"I…" She found it difficult to start. "I thought this was the way…. I guess people aren't my strong suit, but…." She looked up at me. "You've been nice to me; so nice that I guess I forgot that you weren't doing it because I was nice to you, but because you had to be." She took a deep breath in.

"Now," I said. "You need to decide what you want to do. What I won't do is continue to be treated the way I have been." She grabbed this opportunity quickly. She looked up at me, asking, "Do you mean you'll stay?"

"If I stay, we'll have to change and change quickly."

"What do you mean?" I smiled.

"If you want to impress them, we can do it and have fun at the same time." She as intrigued.

"What do we have to do?" I took both her shoulders.

"First of all, let's get them thinking." I looked her squarely in her eyes. "I want you to go to the ladies room, and take off your bra." I left it there.

"What!? You've got to be…"

"Stop it." I talked quickly. "You're still going to be clothed, and most of the people won't even notice the difference, and those who do will just ask themselves what's up. And before you say anything else, we're going to act like a couple who can't keep their hands off of each other, and we're going to be so sweet that butter wouldn't melt in our mouths." While she still seemed to resist, I could see that she was thinking seriously about the conspiracy.

"Believe me," I said. "If they don't think you can relate well to people, we need to show them that you can be very, very friendly." She looked at me for a few seconds, a small smile forming on her face, before turning away toward the ladies room. She returned quickly, her bra folded in her hand, and gave it to me.

"Here. I certainly can't walk back to the table with this in my hand." I placed the bra in an inside pocket, and took her hand. She smiled slightly, as she squeezed my hand.

"You certainly can't," I said. "Let's go." We returned to the table, and I took the lead.

"Sorry for our absence," I said. We sat down, and I placed my hand on her thigh, knowing that at least those sitting near us would notice. Then we returned to the conversation and the meal. We continued to eat, but both of us got involved in a conversation with the man on my left. I had her lean across me to answer a question, and placed my hand on her shoulder, squeezing it slightly. After doing so, I noticed the boss' wife looking at us, with a question on her face. I didn't linger looking at her, but just continued the conversation. When Betty stopped talking to the man on my left, she continued leaning toward me, not too obviously, but enough to show our physical contact. As we turned again towards our plates, she sat back in her chair, and I dropped my arm, though she then placed her hand on my thigh, a bit nearer to my crotch than I thought she needed to be, and as I looked up at her, she smiled, then looked back at her food. Not a problem, I thought. She later returned to conversation with the coworker on her right, and I noticed him looking toward her chest. I followed his gaze, and noticed that her nipples were hard and straining lightly against the fabric. Apparently, she was enjoying this.

When dinner was completed, and we were breaking before dessert, she arose and went with a female coworker to the ladies room. I continued the conversation with people at the table, who, perhaps because Betty had chilled out, weren't nearly as standoffish as I thought they were earlier in the evening. Betty returned shortly afterwards, smiling and laughing with the other woman from the table. When she sat down, she leaned toward me and whispered, "Here, take this" she said, as she slipped something into my jacket pocket. My face clearly asked the question, and before I could speak, she squeezed my thigh and whispered, "My panties -- they were too wet now anyway." My eyes widened, as I suddenly realized things had gone a bit farther than I had expected. I was still a little dazed as we continued the conversation, and I soon excused myself to make another phone call.

"Eleganza Professionals, may I help you?"

"Leesa. Wade."

"Hey, did you just get home?"

"Actually, I haven't left yet."

"Oh," she said. "I figured you got my message on your answering machine. What are you still doing there?"

"Well," I began. "I decided I wanted to make this a win-win, and…." I could almost see her eyes roll.

"Wade, don't tell me you started to counsel her." I told her the entire story quickly, knowing she would burst out laughing. She did.

"What am I going to do with you?" She said. "And, what are you going to do with her!?"

"That's why I called," I said. "I'm really at a loss -- the whole panty thing kinda threw me. I figured it was time to call in the cavalry."

"Wade," she began. "I think this time you're on your own." She paused, before asking, "Did you drive in separate cars?"

"Yes."

"Well then, there you go. As long as you can make a tidy exit into your car as you leave, you should be okay." I had actually forgotten that, and it seemed to be a perfectly natural way for me to escape, so I relaxed and felt my breathing go back to normal.

"You're right," I said. "That should make it easy, since I really don't have to go back to her house when we're through. Thanks, Boss."

"Don't mention it," she said. "Keep yourself safe."

"Thanks. Bye." I hung up, feeling a bit better. I returned to the table, and Betty was still engaged in conversation. I sat back down, only to have her lean against me, and place her hand on my thigh again, very close to my crotch. I was able to avoid getting hard, but it took some effort. We continued in much the same vein for about a half hour or so, when folks began to leave. We soon made our excuses to Betty's boss, and left. Betty and I held hands to the elevator, when I thought she would let go. Instead, she stood even closer to me as we descended into the parking garage. When we finally reached the garage, I turned to her and smiled.

"Well," I began. "I think we pulled that off quite well." She hesitated for a few seconds before responding.

"Oh," she said. "I guess we did." She squeezed my hand, just as I was starting to let go and walk toward my car. She looked me in the eyes.

"Let's go in your car." Now it was my time to hesitate. Just then, another couple from the party came down the other elevator.

"Goodbye, Lance,… Shirley," Betty said, and she started us walking toward my car. "Remember, you're driving," she said.

"Uh,… I uh…." She turned toward me and whispered.

"We have to play this out." I nodded.

"Right." We walked to my car, and I opened the door for her, then went to my door. I looked at the other couple before I put my key in the ignition. Betty touched my arm.

"We have to keep going," she said. Noting my hesitation, she added, "I can pick up my car tomorrow. Let's go." Not knowing what else to do, I turned on the ignition, and started toward her house. As we drove, I noticed that she had turned to watch me. She started making small talk, letting me know some of the reactions of her coworkers, and how different some of them treated her at the party. I only half-listened, because I didn't quite know what to say, or if I should say anything at all. When we finally got to her house, she turned to me and said, "You know, I do expect you to escort me to my door at least." I put on my best "game face."