Private Tutor for Trophy Mom and Daughter

Chapter I: Landing the New Job

I graduated from college just as the economy took a sharp downturn and the job market for English majors was considerably bleaker than it normally is. After failing to land a teaching job, I put ads in some upscale publications as a private tutor. Living on Manhattan’s Upper West Side I thought I had a good chance of stringing along enough students to keep my head above the water. It turned out that I would only need a single customer. The call came from the Talbotts of Connecticut, real blue blood DAR Yankees with pedigree and wealth. I corresponded with Mrs. Talbott about tutoring her daughter, Linda, who was having great difficulty graduating high school. She had just turned 18 but was in danger of flunking out. I sent Mrs. Talbott my resume and references. She also asked me to send her a photo of myself and to allow her to check out my Facebook page. Finally, she agreed to send her chauffeur to pick me up and bring me out to their mansion.

Mr. Talbott was not around, which I soon learned was the norm. He is a high powered New York lawyer, the senior partner in his firm, who keeps an apartment in the city–and in several other cities around the world–and rarely comes home. I was meeting the third Mrs. Talbott he had gone through. Mr. Talbott is in his early 70’s and the third Mrs. Talbott is half his age, in her mid-30s, and Linda is a daughter from Mrs. Talbott’s teenage years, about half her age, just turned 18.

I was expecting a matronly society woman, but discovered Mrs. Talbott–Nina–to be what can only be described as a trophy wife. She looked like a beauty queen. Tall, blonde, blue eyes, breasts that I immediately thought were too large to be God-given, not to mention such perfect features that I suspected had cost Mr. Talbott a small fortune in cosmetic surgery and dental bills. She wore a cream colored, translucent button-down blouse that beautifully displayed her cleavage, held in place by a lacy cream-colored bra. She had a perfect tan, golden skin that highlighted not just her face, neck, and chest, but also her long, shapely legs. She was wearing a skirt that was actually a conservative length, but it was the wrap around kind, so when she sat down it parted high on her thigh. She had a habit of jiggling the upper foot over her gorgeously crossed legs, dangling at the end of her toes her spiked high-heeled shoe and with the leg movements making her skirt ride higher and higher up her deliciously long thigh.

For all the wealth of her surroundings and her quite intimidating beauty, Mrs. Talbott was actually quite friendly and down to earth. She immediately asked me to call her Nina. In turn, I invited her to call me by my first name, Joe. She said that she was really impressed by my resume, not only by my academic credentials, but also that I was on the swim team and the tennis team, and played the piano. “When I saw your picture I got really excited at the prospect that you could be our tutor and maybe that you could give swimming, tennis, and piano lessons as well,” she said.

I’ve always been lucky with the ladies. I have what I guess women call the tall, dark, and handsome look. I’m muscular, athletic, and good looking. This was one of those situations where it looked like I was able to take advantage of my looks.

Nina was about 15 years older than me, obviously much wealthier, and soon to be my employer. She told me a bit about the family situation, and about her relationship with Mr. Talbott (she didn’t volunteer his first name and I knew if I were to meet him I would not be first-naming him any time soon). She also filled me in on the dismal academic record and painful social struggles of her daughter, Linda.

Nina confessed that she and Linda came from “the wrong side of the track.” She said that she was essentially raised as “trailer trash” and that she had used her beauty to escape a life of poverty. She landed a job as a stripper in an exclusive Manhatten gentleman’s club which Talbott frequented. He was particularly drawn to her. In part, his attraction seemed to be that he could play the Henry Higgins role in transforming Eliza “Nina” Doolittle by cosmetic surgery while he was still married to the second Mrs. Talbott.

Mr. Talbott actually spent a couple of years preparing her for her role as Mrs. Talbott III, so she would be ready when the time came. She was totally dependent on Talbott but made it clear to me from the start that she not only didn’t love him, but didn’t even like him. She was made in his image, did anything he wanted, was at his service when ever he wanted to be serviced, but for Nina it was all an act, as though she was still working for $20 lap dances, but now with a single customer and no music and partying. She said that she was completely isolated in her mansion, had nothing in common with the other wives in their social circle, and missed her friends from the strip club and from her previous life.

Now, she said, Linda was also lonely, had no friends, and really had no one in her life except her mother, Nina, and her mostly absent and distant, but nevetheless demanding and controlling stepfather. Among his demands was that Linda had to be pretty and smart. Nina smiled and said, “Fortunately, being pretty is no problem for Linda, but she is a terrible student, just like I was.” With that, she called Linda in to meet me, introducing me as “your new tutor, Mr. Joe.”

Linda was indeed a natural beauty, much like I’m sure her mother was before she got all the “work” done on her. Linda was a brunette, which I guessed was also her mother’s natural color, but with the same blue eyes. Unlike Nina with the hourglass figure, Linda was lanky and slim. She was wearing low-riding jeans and a tight knit shirt that left a nice expanse of tanned, sleek waist exposed. She was very shy, clearly not aware of her own beauty, and kept her eyes mostly downcast and her answers to my conversational questions to monosyllables. I asked about school, but this clearly was not a subject that interested her, so I tried to find what things did interest her, and she couldn’t really come up with anything. I could see that tutoring Linda might be difficult. Nina excused her and Linda wandered off.

After Linda left the room, Nina and I were again in a one-on-one conversation. I had to be careful not to allow my eyes to wander down because her cleavage, even if fake, really was magnificent. We talked about Linda’s needs some more, but then Nina said that she was also hoping that while Linda was in school that I could be tutoring her as well. Nina said that she had was really badly educated and always felt inadequate among the high society set, and wanted me to help her to be better educated, as well as to learn to play the piano and to improve her tennis game. Nina said that she was looking for a full-time, live-in tutor to stay at the mansion during the week but to have my weekends free during which I could stay or go as I liked. She informed me that they had a private swimming pool and their own tennis court.

Nina offered me an annual salary that was well beyond what I could have been making through any other combination of jobs available to me, as well as all the benefits of living on the grounds of the mansion. Just to be in the presence of this beautiful woman and her pretty young daughter was enough to convince me that I would accept her offer, but I hesitated a bit, saying I wanted to think about it some more. Nina got a very worried look on her face and said that she knew I would be just perfect and asked what she could do to convince me to take the job, leaning forward as she did so. My eyes were involuntarily drawn to her breasts. I quickly looked up to meet her eyes, but she had caught me.

She gave a smile. “I think you’ll really like it here, Joe. Linda and I are so lonely. We’re both desperate for a young man, I mean a tutor, who will be nice to us and help us to fit in here.” She stood up and put her hand on my shoulder. “Please, Joe,” she looked down at me and her other hand brushed the side of my face. She stepped closer. “Are you hesitating because I told you about my career as a stripper?” Nina then drew her foot to the arm rest of the chair I was sitting on. Her wrap-around skirt parted to reveal a lot of leg. “I miss giving lap dances,” she said as she started unbuttoning her blouse. “Am I convincing you to take the job?” she asked as she finished unbuttoning her blouse, threw it aside and moved so that her breasts, displayed so charmingly in the lace bra were right at the tip of my nose. I inhaled her intoxicating perfume.

“I can see that you could tutor me in a few things yourself,” I joked. I reached up to touch her breast but Nina turned her back to me, untied her skirt and whipped it aside. She was wearing matching cream-colored lace thong panties. With back still to me, she bent at the waist so my face was now staring right at her tight, round, perfect ass. I moved forward to give it a kiss, but she moved away, picked up her blouse and skirt, and said, “We really shouldn’t be mixing pleasure with business.”

I stood up and my pants tented out in front of me. Now it was Nina’s turn to have her eyes wander down. This time I caught her looking, and I smiled. “Okay,” I said, “I think I will like it here. I’ll take the job.” Instead of a handshake, Nina gave me a hug and held it longer than professionally warranted and tightly enough that I could feel her breasts. I’m sure she could feel my hard on. I let my hands wander down the small of her back, and then cupped the perfect handfuls of her ass cheeks.

Nina gave me the address of Mr. Talbott’s law firm, where I found the contract process more extensive and certainly stranger than I had anticipated. I had to get a full medical exam, had to be tested for HIV and all other sexually transmitted diseases, took drug tests and had to agree to weekly STD and random drug testing. I also had to agree to be investigated by Mr. Talbott’s law firm, which did an extensive background check, and finally I had to sign a confidentiality/non disclosure contract that made me swear that I would never tell anyone what went on with my tutoring job and that forbade me even from telling anyone who I worked for. I signed the contract without laying eyes on Mr. Talbott. Later that week the chauffeur came again to pick me up and a few bags of my stuff. I was moving in with Nina and Linda and my new home.

Chapter II My First Day as the Talbott’s Tutor

The Talbott mansion was huge so finding a spare bedroom for me was no problem.