My Friend the Escort

This story is a work of fiction. Any similarities to any real person or entity are entirely coincidental and unintended.

*****

I had met Shelly while I was in law school and she was working on her MBA at the same university. Shelly was a girl you noticed with her blonde hair and a magnificent smile. Shelly had been a varsity lacrosse player in undergrad and had a firm, athletic body that included rather large but perfectly-shaped tits. She was also very intelligent and, usually, a lot of fun to be around. I say "usually" because Shell was very goal-oriented. Shelly would do what was necessary to get the things she wanted, whatever was necessary.

I'm not entirely sure why I caught Shelly's attention, but I did. While she was not aggressive enough to put off-putting, Shelly apparently decided that she wanted me and she put on a press to get me. Not that I was complaining. She was a beautiful woman, great fun to be with, and an energetic, if intense, lover. There was always a recovery period after sex with Shelly.

I thought that Shelly and I worked pretty well together. We both graduated near the top of our classes. I took a job as an associate with the local office of a huge national law firm. Shelly got an entry level management position with a relatively new, but very hot, tech company. We got married a few months after graduation.

Six years on, I thought that things were going pretty well. We didn't have everything Shelly wanted (a McMansion and a couple of Mercedes to name just two), but I was on track to partnership at the firm. We had bought a nice house, with a huge mortgage, in a safe, leafy, and prestigious neighborhood. And, we had two great cats.

Not long into my sixth year, the firm merged with a law firm in the UK. That move was not done without some internal opposition. Not long after the merger became definite, I was invited to lunch with the two partners with whom I had worked most. Over a rather long lunch, the partners told me that they and three other partners were leaving to start their own firm. They each had a solid book of "portable" business and were confident that they would do well. They asked me to come with them. While I would start out as an associate, they were sure that I'd join them as a partner before long.

The luncheon put me in a difficult spot. There was a lot of risk moving to a start-up firm, no matter how well-established the partners starting it seemed to be. As an employee, I'd be among the first to go if the business did not pan out as they expected and costs had to be cut. On the other hand, the merger of my present firm meant that a lot of new partners who had never even met me would have a huge say on my future there and, with the partners I knew best leaving, the people most likely to go to bat for me would be gone.

I talked the issue over at length with Shelly. She wasn't that helpful.

"You have to do what you think is best," she told me. "You know that we both have things which we want to achieve." By that, she meant that there were things she wanted to acquire. "You need to decide which course is most likely to get us to our goals." I also knew that Shelly was not being promoted at her company as rapidly as she felt that she deserved.

In the end, I decided to go with the new firm. While the move didn't cost me financially, a year on the firm was not in position to give me the automatic annual raise that I had always received at my old firm. Shelly was spending more and more time at work, t the point that we frequently only saw each other late a night when we were both too beat to do much besides sleep. We went on like that for another year. I assumed that the situation was temporary and was just the sacrifice that had to be made to get to where we wanted to be.

I came home early one night because Shelly had called me at the office with the dread message "we need to talk." I had no idea what she wanted to talk about, but knew that it couldn't be good. Still, I could not think of any reason to expect a cataclysm.

Shelly was there when I got home. She was dressed as she always did for her office: professional but a bit sexy. She looked stunning. Of course, she always looked stunning, at least to me.

Shelly handed me a drink as I walked in. That was unusual. Shelly never played "waitress," to use her term. She asked me to sit down in our expensively furnished living room.

Once I was settled and holding my drink very carefully, Shelly got right to the point.

"Harry, I've been having an affair with Egon Barz." Barz was the founder, CEO, and majority owner of the company for which Shelly worked. "It has gone quite well and Egon has asked me to move in with him. He's offered to marry me once our divorce is final."

What do you say when your world has just been blown apart? I guess that my face showed the feelings I had: fear, anger, nausea. Before I could think of anything to say, Shelly spoke again.

"Harry. You know that I have things which I want to achieve. You and I just aren't getting there fast enough. You're a great guy. This isn't personal, it's just business."

That sure made me feel better.

Shelly left the room and came back carrying two large suitcases. She set them down. "I'm moving in with Egon this evening. This will hold me over until I can get movers to get the rest of my stuff."

I sat there dumbfounded and speechless. After a few moments, Shelly picked up her bags. "You could help, you know." I didn't move. Shelly took her bags out to her car.

Shelly came back through the living room without saying anything and I heard her climbing upstairs. When she returned, she was carrying two cat carriers with my buddies inside. As she walked out to the garage, she said, "I've got a litter box and a bag of their food in the kitchen, would you please bring that out?" I still didn't move.

When Shelly came back in and saw me still seated, she muttered "worthless" and went into the kitchen. She came back carrying with the litter box and food. She stopped and stared at me for a few seconds. She said "bye" and went out to the garage. I heard the connecting door close and, a couple of moments later, I heard her car start.

Since our state has no-fault divorce, there were no grounds to contest Shelly's divorce petition. Most of the things we owned had been acquired during our marriage. Some of that got split between us. The more valuable things, like our home, got sold. I guess to her credit, Shelly didn't pursue a claim for alimony. Within a surprisingly short time, I went from having a beautiful wife, two cats, and a nice house in the burbs to living completely alone in a downtown apartment two blocks from my office.

I was basically a wreck. At least it didn't affect my work, or I don't think that it did. My colleagues were supportive. Since I was now "free again," I should start going to the bars where women congregated and should start dating. I couldn't do it and didn't try. Every woman I saw just reminded me of Shelly. My world had reduced itself to the office and my apartment, with infrequent trips to the store.

I had been plodding along this way for about six months after the divorce when Stan, another of the partners, told me that we were having a drink after work. After some chitchat in the bar, Stan got to his point.

"Harry, you're a mess. You need to get laid. Ok, I get it. You don't want to do the pick-up scene. You've been out of that for years and you don't have any confidence in your own judgment after what Shelly did to you. But, buddy, we all have basic needs. Yours aren't being met."

Stan took swallow of his drink. "Harry, I'd really appreciate it if you didn't tell anyone this, but, since Jan left me a couple of years ago, I've been using an escort."

Being slow on the uptake, I asked "A what?"

"A hooker, Harry," Stan replied. "But, Samantha is no ordinary hooker. She's very high class, smart, and good-looking. If you just saw her on the street, you'd never suspect what she does. She only takes 'clients,' as she calls them, on referral from other clients. She's not cheap, but you can afford it. No emotional baggage Harry. Just a really fun business transaction. I talked to Sam about you and she's willing to take you on. Here's her number. Call her. You will not regret it!"

Stan handed me a slip of paper with a telephone number on it. Stan was trying, in his way, to be helpful. But, I couldn't help being offended by his suggestion that I hire a whore. I tried to keep my mouth shut, but Stan could tell that his effort had not engendered a lot of gratitude. We quickly went our separate ways for the weekend.

On Saturday, I started thinking some more about Stan's suggestion. Maybe he was right. Maybe I should look at sex as nothing more than a business transaction. That certainly seemed to be how Shelly saw it. Maybe I could have some fun and the knowledge that I was just renting the girl would keep my emotions out of the equation.

Against my better judgment, I called the number Stan had given me. I got a voicemail message asking me to leave my real name, a telephone number, and the name of the person who had referred me. Not surprisingly, the message had been recorded by a rather low, sexy female voice. I hesitated, but finally left my name and number and Stan's name.

Several hours passed. I realized that there could be any number of reasons why the hooker had not returned my call. Still, it was depressing to think that I couldn't even get a whore to call me back.

When my phone finally did ring, I heard the same voice that had been on the voicemail ask, "Is this Harry Stone?"

"Yes," I replied.

"Hi. I'm Samantha. Stan Jensen told me about you. I'm glad that you called. I'm sorry, but I'm busy this weekend. Are you available next Friday?"

"Uh, yes, I suppose," I said.

"Great! Let's say 8:00 p.m. Room 527 of the Mansion Hotel. Is that ok?"

"Yeah, I guess so."

"Great! My fee is $ 2,500. For obvious reasons, I'd much prefer cash. You'll pay me upfront. There's no set time. We'll just see how it goes. Hey, what do you like to drink?"

"Beer or red wine," I answered.

"Oh, come on. How about something a bit stronger?"

"Ok. Dark rum and tonic," I said hesitantly.

"Great. I'll see you Friday night. I'm looking forward to meeting you.

Twenty-five hundred dollars added greatly to my reluctance to go forward. I'd never been with a hooker and doubted that I'd recognize one if I saw one. Still, there was something about that voice. I kept reminding myself that it wasn't like I was cheating on my wife. Not anymore.

The Mansion Hotel is pretty high-end hotel Downtown. I had gotten the $ 2,500 cash earlier in the day that Friday. I stopped at a bar I hung out in some about an hour before my appointment for some liquid courage. That turned out to be a mistake.

The woman who opened the hotel room door fit no part of my preconceived notion of a hooker. She was almost my height and slender. She wore an elegant black dress with no visible jewelry. Her face, framed by long straight brown hair, was quietly very lovely. It didn't seem to me that she wore any make-up.

The woman extended her hand to shake. "Hi. I'm Samantha. Please come in. You're more attractive than Stan led me to believe." Of course a hooker would say that.

I stepped into a suite. Samantha walked over to a table, picked up a glass, and brought it to me. "Dark rum and tonic as you asked," she said, handing me the glass.

I reached into my sport coat pocket and drew out and envelope which I handed to her. "Your fee, in cash as you asked."

Samantha smiled. Her smile was warm and friendly. "Thank you," she said and seemed genuinely pleased. "Take off your coat. Have a seat. Let's talk and get no know each other a little, then we'll see what I can do for you."

Samantha's dress clung to her body. While Samantha was slender, she had a very nice, proportional shape. Her moves were very graceful. As I sat down, she giggled, "Oh, I guess that I should get rid of this." She reached behind herself and unzipped her dress. She pulled the top forward and away from her shoulders and let the dress fall at her feet. What remained was a very low-cut black bra, dark pantyhose with a pattern in them, and black heels.

After Samantha folded her dress and set it aside, she said, "It looks like you're ready for another drink." She brought me another and sat down on the sofa, leaving a little distance between us. "Now, tell me a little bit about you and what you want from me," she said as though she was genuinely interested.

I vaguely remember that we talked for a while and I drank rum like water. My next clear memory was waking up in bed with sunlight coming in through the suite's bedroom window. Samantha was nowhere to be seen. I called her name. Silence. "Oh shit!" I thought.

Naked, I got out of bed. I noticed that my clothes were neatly folded and sitting on a chair. My shoes were underneath the chair. Clothes were not my immediate concern. I went into the main room and picked up my jacket. My wallet and cell phone were still in it. Pulling out my wallet, I saw all of my credit cards in place along with my cash.

Feeling slightly relieved, I looked around the room. I half expected to see that I had barfed somewhere. Instead, what I saw was the envelope I'd given Samantha lying on a table inside the door. Inside the envelope was $ 2,500 cash. After checking the cash, I noticed writing on the outside of the envelope.

"I am sorry about Shelly," Samantha had written. "I didn't do anything for you, so I didn't take my fee. You do need to check out and pay the room bill. That won't be bad. The hotel gives me a discount. I'd like to see you again. Please call." Below that, she had written "Sam" and a phone number which turned out to be different from the one Stan had given me.

I was a little embarrassed and a lot hung over. I showered, dressed, and steeled myself for further embarrassment checking out. However, the front desk clerk acted completely normally. Sam had been correct: the bill was a lot less than I'd expected.

Although I saved the envelope with Sam's writing on it, I decided to put the experience behind me. It was just the sort of stupid shit that a man does when his wife leaves him. Despite a lingering thought that I should, I did not call Sam.

I was in my office about 11:15 the following Thursday morning when my cell phone went off. I was surprised and annoyed because I got very few calls on it when I was in the office. I went through the machinations to accept the call, and said "hello."

A low female voice responded, "Harry? This is Sam."

"Hi Sam," I said unenthusiastically.

Not deterred, Samantha replied, "Hi Harry. It's great to talk to you again. Hey, I need to do some shopping downtown. I was wondering if you could, maybe, take a slightly long lunch and meet me. You don't need to bring any cash this time."

Again, there was something about that voice. Almost involuntarily, I said. "Sure. What time and where?"

"How about twenty minutes. Meet me in front of Z Rabbit on Seventh."

Z Rabbit was a new and trendy restaurant. Samantha was standing on the sidewalk when I walked up.

"Hi Harry," Samantha smiled. She did have the ability to make you think that she was genuinely glad to see you. Gesturing towards the restaurant door, Sam said, "Don't think that I'm trying to get you to buy me lunch there. This is just a convenient meeting point. I need some clothes for work and I thought that it would be good to get a guy's opinion before I shell out a lot of money."

Sam took me by the arm and we walked a couple of blocks. She led me into a shop with virtually no on street display, just the name "Ruffles and Lace." The store sold men's and women's apparel, what I guess you would call "erotic apparel." Sam obviously knew the woman working in the store. They talked for a longish time while I hung back. Finally, the saleswoman reached into a drawer, pulled something out and handed it to Samantha.

Samantha turned to me, took my hand, and led me deeper into the store. As we reached a curtained door near the back wall, Samantha pointed to a chair and said, "I need to try something on. You sit there." I sat as Samantha went through the curtain.

I was wondering why the hell Samantha had brought me here when she came back out. Samantha was wearing only a dark, very sheer, patterned body stocking. While Samantha was a slender woman, she had a very good body, the front of which I could see clearly through the body stocking.

"What do you think?" Samantha asked me.

I decided to be honest. "You look fantastic in it," I said.

That made Samantha smile. "Wait," she said, "it gets better." Samantha turned her back to me. While the material of the body stocking covered her upper back and her thin, elegant legs; it has been made to leave her buttocks bare. It was small, but Samantha had a great, tight-looking ass.

"What about that?" Samantha asked over her shoulder.

"The contrast between the material and your bare skin is exciting," I said. "It looks great on you, but I'm beginning to think that anything does."

That compliment bought me a kiss on the cheek. Samantha modeled several more items that left her exposed in various ways. It was a pretty exciting experience.

After Samantha had made her purchases, we just had time for a hot dog from a street vendor. I paid. After we finished and dropped the wrappers in a trashcan, Samantha took my hand.

"Harry. I do want to see you again. I know that you've had a rough time. I can empathize. I can also help. Meet me at the same room tomorrow night at 7:00 p.m. Just bring $500."

Against my better judgment again, I said "yes." I suppose that a high-end hooker develops the skill, but there was something about Samantha that made me want to see her again.

When Samantha opened the hotel room door the next night, she was completely nude. She looked very, very good nude. As I walked inside, she said, "I want to try something very different this time. Take your clothes off." I reached into my jacket and pulled out her money. She waved a hand, "We'll deal with that later."

When I had all of my clothes off, Samantha came very close to me. There was a scent to her. I'm terrible at description, so I'll just say that it was subtle but noticeable, and very alluring.

Samantha leaned forward and gave me a quick kiss. Taking a step back, she said, "I really love masturbation. There's something nice to me about pleasing myself, and I know better than anyone else what my body wants at that moment. I thought that we could masturbate together."

Taking my hand, she walked over to a chair in the corner of the room. She sat down facing me and spread her legs. It sounds a bit strange to say that a woman has a beautiful cunt, but Samantha did. She rummaged for a moment in a handbag on the floor before pulling out a rigid clear plastic dildo.

"I have a number of toys, but this is my favorite, "Samantha said as she began rubbing the head of the dildo on her cunt lips. Watching this was, of course, exciting and I got pretty hard. After she had teased herself sufficiently, Samantha looked up at me. "Why don't you jack yourself off while I work this guy in deeper?"

I began stroking myself as Samantha started sliding the dildo insider herself. Samantha was watching me. After a minute or so, she said, "Harry, is that really how you jack off?"

I was thrown by that comment and just said "yeah."

"You are missing some much," Samantha said. She pulled out her dildo and stood up. "Come on," she said. She took my hand and led me into the bedroom.

I sat down on the bed and Samantha sat down next to me, so close that we were touching. She leaned forward, gave me another quick kiss, and took my dick in her hands. "Let me show you a few things," she said.