The Call Girl, The Lawyer, The Wife, & The Voyeur

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Kelly's flash back as she starts over.
5.6k words
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It was roughly a 6hr flight from Boston to San Diego, and I had thought that I would sleep most of the way. At least that had been my plan on the red eye, but as it were my mind wouldn't let me. I was looking for a new start. My mind was always wandering in Boston. I was distracted constantly with the thoughts of her. No sooner had I sat in my first class seat, taking my blanket, and trying to fall asleep the distractions came again.

It had been six months since the last time I had seen her, but my mind didn't take me to that night. It went to our first encounters. The images were so vivid that at first I thought I might have dreamed it, and perhaps I did, however I was conscious through all of my thoughts.

"Hello Madame?" I had said. Madame was my boss, a very good boss.

"Kelly, when will you stop calling me Madame? I have told you just call me Janie! None of your sisters ever used that term!" Janie said with annoyance. She looked at me with those chestnut brown eyes, and her blond hair pulled back in a long braid. I knew it was not a work night for her. She normally went on her "dates" with her hair down and with more make up on, not that she needed more. Tonight she was just running the shop.

"Well it adds a sense of mystery and expectation for me, when I call you Madame." I said back in my most excited little girls voice. I accompanied it with a smile and wink.

"You are so much more cheeky than your sisters. I admire it, as it reminds me of your mom." Janie's eyes had a bit of a wistful look in them, as she spoke the words.

"No dates tonight?" I asked her. She was dressed in pant slacks and a nice gray blouse, and as always her high heels. I never could help but check her out. She was stunning still, at 40. Tall for a woman her age, with long legs. Her chest was perfect still with large full breasts, and her cleavage always accented by her blouses. Usually she wore a string of pearls that would draw your eyes to them, and tonight was no difference. The tops of her honey brown melons looking so enticing.

She shuck her head and answered, "Not tonight, I have other plans for this evening and want all my energy for them."

"Not sue that mom would want to hear that you have to save your energy. She might think that makes you old and since she is older than you it wouldn't go over very well. Besides she would say that she can still love all night and work all day" I jested.

"You devil!" She smiled back at me. "Well I may not have a date, but you do, and if I'm not mistaken you will be quite worn out by the end."

Janie went on to explain, that I was going to be the entertainment for a party. One of her most special clients, a very rich woman named Wendy, was putting on her annual Partner Dinner. Wendy owned a very high end accounting firm, and every year she put on a dinner for her senior partners. These happened to be 5 men, and they were all accountant, very good ones. As Janie put it, "They have not had much experience with women of our level."

Wendy annually brought in a high class call girl for the guys and let them gang bang her. Wendy for her own tastes preferred women as well and normally she would participate in her own time.

"Be honored Kelly as I have given this party to only a few, and those include all of your sisters. In fact I once sent the twins together." Janie was smiling at me now. "Are you nervous?"

"No, while I've not ever done 5 guys at once, I have experienced three." I said a gleam in my eye. "I'm excited. So, what should I wear."

"I doubt that any or all of the guys will be the one to wear you out. I would put my money on Wendy. As for what to wear try something classy as it is a business dinner. Maybe a white cocktail dress to accent your red hear. Short, exotic, and all the other accoutrements: garter, stockings, matching panty and bra." A smile evident in her voice and eyes as I was looking into a mirror imagining the outfit and could only hear her voice.

She walked up behind me and gently put her hands on my upper arms and looked me over in the mirror. Janie is very tall almost 6 feet, and with +3" heel well she towered over me. I'm diminutive to say the least. At 5'1", perhaps a stretch, and 90lbs. The image in the mirror reminded me of a mother looking over a daughter as she prepared for a pageant or first date.

"I'll drive you tonight as I've business in town." She said still looking at me in the mirror. "I'll pick you up at 6:30 in your lobby."

"How will I get home?" I asked.

"I bring you home in the morning. Not too early, as Wendy likes to sleep in after a party like this. It is at her downtown penthouse condo, and she usually likes the girls to stay with her." She add this all with a devilish grin, before kissing me on the top of the head and walking back to her desk.

***

I wore very short white dress that I had just recently bought. It had two spaghetti straps which tied at the back of neck. The top was almost a like a tube top of solid silk, then between the top and the skirt was a shear material. Then a solid white silk skirt at the bottom. The hem fell on my very upper thigh, and if I bent over just a little I knew my buns would show.

I wore white stockings and a white garter with a platform heal that gained me 5 inches. I didn't wear a bra, my small B-cup breasts don't need one, and I could hide one in the dress I was wearing. I did however wear a pair of Victoria Secret white lace-trimmed cheeky panties, which had the bottom half of my well sculpted bottom hanging out. I love to wear them and I work endlessly at the gym and religiously at the table to make sure that they look just right.

I wore a very light shade of green eye shadow, and lots of massacre to highlight my green eyes. My long read hair was in a tussle of curls hanging loose about my shoulder and down to my mid back. To finish it off I added a light pink lipstick. It makes me look younger, not that I wasn't young at the time, just about to turn 19.

I went down promptly at 6:30 to the lobby of my building. Janie is a very prompt person, and she expects her girls to be prompt as well. Janie, I knew, had learned this from my mother. See this was my mother's company. Before she meet daddy, and maybe for a while after she had meet him. Janie had been one of my mom's favorite girls. Now Janie runs the business as a full partner, and after 26 years and 4 daughters my mom is slowing letting Janie buy her out.

The business is very small with only 5-6 girls. Confidentially is the foundation of the business, built by a lawyer, my mom, and a very wealthy one at that. She had captured very high end A-list customers, including my dad, in the Boston and New York. A night with one of us could cost one $10,000. Not that we got that kind of money, but we did get 30%-40%. You see in this business it is always about who you know, and the bigger the wallet the bigger the issue is if something goes wrong, so the more discrete the night must be thus the higher the rate.

The girls were also very special. Recruited from the upper class, educated in the best universities, and all of us picked for our very special talents, shapes, or endowments. Girls typically worked for just a few years before settling down with someone, and on many occasions that someone was a regular. My other three sisters we out of the business at this time. My oldest two, who are twins, happily married to two very wealthy men, and my other sister engaged to a Kennedy.

As the elevator door opened and I came out, I could see Janie's Mercedes pull up just outside the door. I made my way right out to her, and open the door to find her beaming at me. "That outfit is perfect, and you look so young. Well of course you do you are only just 19."

"Not quite Madame." I replied in my most cheesy British accent to make it even more cheeky. This got me a very stern look, then a smile.

The conversation to the Wendy's downtown residence was jovial, and I caught Janie looking at my legs and panties several times as we waited at traffic lights on our journey. There was no hiding my panties as the skirt was too short not to show them when I was sitting the way I was, and I didn't try to pull my skirt down or cross my legs to keep my modesty. To tell the truth this is what I wanted; Janie's attention. I adored her, and her looking at me was more than a turn on.

We arrived at the upscale apartment complex in downtown Boston. These apartments probably all went for more than a $1 million, and Wendy's being the penthouse would have been probably more than ten times that. As we pulled up the doorman came to open my door. I did nothing to hide the view of my panties as I got out the door. He smiled and tried to look me in the eye, but I could still see a little red in his cheeks from the show. Janie called him by name and said that I was going to Wendy's tonight. I thought it odd at first that Janie would know that doorman by name, but then Wendy had been a regular, and perhaps maybe even Janie's regular.

As we rode up the elevator I tried to be very distracted and could see the doorman sneaking glances at me. I could also make out a bulge in the front of his trousers. It turned me on more, and I began to worry that my panties might soak through even before I got to the dinner. I was so turned on. My body feeling tingly, my nipples hard and very sensitive, and my pussy was aching. To be blunt I had always wanted a gangbang. I had only ever managed to get three guys at once, and it was super. But still, it is not the same has having 5.

I had prepared in all the proper ways. Janie expected us to be open to any kind of sex, so I always made sure I was ready. As well I had drank lots of water, learning from experience that nothing was worse than being engaged in long drawn out sex and becoming achy and dehydrated. I also made a note to myself to watch the wine. It was always a better experience for my clients when I had all my faculties. I was not one who needed a bit of alcohol to loosen up; I love sex.

When the doors opened I was in a small hallway with only a set of double doors. The doorman walked me to the doors, and opened them without a knock. As soon as he did he announced me, "Ms Wendy, your guest has arrived!" Then he ushered me in, pinched my ass, and winked before closing the door.

Before I had time to recover from the unexpected fondling, Wendy was calling to me, "You must be Kelly?"

I was not sure what I had expected of Wendy. I guess I was expecting a short haired, dyke, or a frumpy accountant, nerdy type. That was not Wendy. She glided like a ballerina, with long shapely legs that we shown off by a black business suit with a very short hem. She was well built like an athlete or dancer with toned arms and a smaller chest, perhaps a large B-cup or small C. He hair was a very dark brown, and she had electric blue eyes, that twinkled with her energy and intelligence. She also exuded confidence with her walk, her bearing, and her smile.

"Janie has told me so much about you." She said even before I spoke. "You are precious my dear. More petite than your sisters and mother."

I must have had a puzzled look on my face. "I know your mother, and your father." She answered my puzzled looked as she came and gathered my arm in hers and began walking me into the dining area. She was very tall, even taller than Janie, and she didn't have much heel on. Her hands large and not as soft as I would have expected from an executive. I would find out later that she was a college basketball star, and still played regularly.

"You do?"

"Why yes, I take care of the books for both your parents businesses." She said while looking down on me. "I have for a very long time, and of course your mother has spent time with me on a more personal level, but not for many years." This was accompanied by a wistful look, and a wink.

The dining area must have been used for the board meeting as there were still papers on the table. The gentlemen however were not sitting but now standing at a bar. They were starting to open bottles of beer or pour themselves glasses of scotch or whiskey. Wendy offered me some white wine which I accepted and introduced me to all the guys. To tell the truth I don't remember men's names, and this night was no different. They were actually all very similar in size ranging from 5'8" to 5'10. None of them were drop dead gorgeous, they were all clean, well groomed, accountants. There were 5 of them, and two of them wore glasses, and all had dark hair, and most had some amount of gray.

Each of them meet me with a polite handshake and then a kiss on the cheek. They were extremely polite to me, and as we began to mingle the conversations were work related mostly as the meeting had just ended. Some were still trying to get their points of view across, or were feeling out the others on how their ideas were being taken, and the others talked more about the economic environment investments, and such.

This lasted a couple of minutes, and I stood and tried not to look too board. I had thought that I would be the center of attention, and then realized that each of them were taking quick looks at me. They were not ignoring me. They were intimidated by me. I almost laughed out loud that a diminutive girl like me would scare these men.

I then noticed that Wendy had left. She came back and two men trailed her. One was a younger man in a business suit which I quickly realized was Wendy's personal assistant. The second man was in his middle thirties if I were to have guessed, and he was carrying table settings.

"Ms Wendy, the catering service just dropped off the meal. I will set the table and set up the service. You wish it to be buffet style?" He said in an Italian accent.

"Yes Antonio, and once you are done you may leave and go enjoy your family tonight. I will not need anything until tomorrow at noon." Wendy's answer showed her warmth.

"William, please just gather all the papers and put them on my office desk. I will go through them later, and here is something for you and your wife." She said this as she picked up a letter and a package. "When is Elizabeth due?"

"A couple of weeks still. Perhaps a New Year's baby!" He said in a very refined Massachusetts's accent.

Within no time the table was cleared, then set. Wendy announcing to the men to find their spots, and for me to sit to her right. We gathered our dishes and had a wonderful meal. The talk was lively and engaging. No business discussed. Families were asked about, Bruins, Celtics, and Patriots analyzed, and for me, I discussed with those around me my college experience. I had just finished my 3rd semester at Harvard, and was aspiring to be a Lawyer. This seemed to intrigue several of the men. They knew that my father was a big time corporate lawyer owning one of the most prestigious law firms in the country. They wanted to know if I was going to work for daddy or my mom. I said "I'm already working for my mom", and this got plenty of laughs.

I ate a light meal, and Wendy seemed to notice, "You are not watching your figure are you?"

"No Madame."

"Please it is just Wendy." She replied, "I have known your whole family, so no need for formalities."

I explained to her that I was ensuring that I had plenty of room for dessert and after dinner snacks. She smiled and nodded her approval. Then things began to pick up. Wendy calling for the end of dinner, and we moved from the table to the living area. In this room were 3 large couches each surrounding a very large plush ottoman. The opposite side had a Christmas tree standing in front of a very open view of downtown.

Wendy picked up a remote and dimmed the lights but not too low, started some soft jazz, and announced to her senior partner's "We had another wonderful year, and in thanks tonight Kelly will be entertaining us. As such and since it is her first time with us, I will do the honor of getting her started, so please take a seat and enjoy the show."

With that the guys all took seats around the Ottoman, and Wendy directed me to the area just in front of the tree where she joined me. Pulling me into a hug she whispered in my ear. "Are you nervous?"

I replied, "Just excited", and raised up on my tip-toes and kissed her on the neck, then I nibbled her ear. I must of hit it right as she gasped a moan and pulled me in tight to her. One hand caressing my back and the other on my butt kneading my globes.

I almost came from the excitement of the night. The anticipation, the atmosphere, and the smell of Wendy. As I said I love sex, and that means all kinds. From the drive over with Janie staring at me, and then meeting Wendy, I would say that I had been hoping for this female interaction to start things off. And I was reveling in Wendy's attention. My hands for the moment were just softly stroking her back from her firm bottom to her shoulders. I could feel the strength and tone of her body. She was an athlete.

My lips left her ear and moved to her lips. Still on my tip-toes I couldn't quite reach them. I moved my hands into her silky hair and pulled her to mine. Her mouth parting and allowing me to devour her lips, with my tongue racing from her teeth to her tongue and all around. I tried to convey with my excitement and my desire for her in that kiss.

We never broke the kiss, and in moments of its start I felt my dress fall from my body. I hadn't even noticed her untie my straps. Now with my breasts bare, and my nipples swollen and rubbing against her blouse I was taken by a small shudder. A mini orgasm as I call it, and I could feel the flood of my juices past my lips and into my panties. If they were not soaked before they were now.

Wendy then broke our kiss and moved us forward to the ottoman. Before laying me down she turned me for all the men to see. I could see their smiles, and looks. All had their cocks out of their suits and were slowly stroking themselves. I took inventory and saw nothing too large. Just some nice sized men, and all hard.

Then Wendy had me face away from the men and bent me over showing off my ass, and pointing out the wet spot in my panties. Then setting me on the ottoman with my legs spread. She asked two of the guys to come and warm my breasts up while she finished undressing me.

With that the two nearest men came over onto the ottoman, one on each side of me, and began to caress my breasts with their hands and twist my nipples with their fingers. They were gentle, but firm. Each of them pulling and twisting, sending shivers down my spine and into my loins. I've very sensitive nipples and on several occasions I have had women get me to the brink of an orgasm just through playing with them. Tonight was no different, and if Wendy had grazed my clit with a finger or hand while she undressed me I'm certain I would have exploded. Instead she seeming to realize this kept her distance to prolong my delicious agony.

I for my part didn't just lie still, when the men came over to the ottoman I reached for their cocks. I had one in each hand and was gently stroking them. Taking time to reach inside their openings and fondling their balls. My parents had made me learn the piano, which today I love to play still. That time spent on the keyboard gave me lots of finger and hand dexterity, and I was using it to the fullest on these two.

Now with my heels, and stocking off, Wendy told the two to go back and sit, and invited two more to take their places. No doubt that if she hadn't the gentlemen on my right would have lost his load. I could feel the tension in his body and in his cock. The head oozing his precum. I took the moment to lick it from my fingers, which engendered a ooh from all that were watching. I love the taste of men. It is not the flavor that I enjoy as much as the thought and the meaning of it. A man's juice is his essence and that is what thrills me. I want his essence and thus I want to taste him.

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