Chapter 2: My First Session With Nathan

A perfect example what I was saying about boys is Nathan, a fourteen year-old boy I tutor in math. His parents are pretty well-off to say the least, as are the parents if most of the kids I tutor. When I first told them my rates I almost wilted, expecting an explosive response as to how outrageous I was being. Well, talk about worrying over nothing; I guess $35 an hour is pocket change for these people.

Overall, Nathan is nothing unusual, just your typical young boy. Although not an athletic star, he enjoys sports, video games, and just about anything NOT connected to school. Not surprisingly, his grades tend to reflect his lack of commitment - which is where I come in.

When I showed up for his first tutoring session I was dressed relatively conservatively - jeans and a loose white blouse. As I wanted to look professional for his parents, I even wore a white bra underneath! I DID draw the line at panties but they wouldn’t have been weren’t visible anyway with the jeans. Knee-high hose and dress heels went on my feet and I had my hair pulled back into a single tight ponytail. Some of my friends who tutored had warned me about some of the pitfalls of showing up looking like a slutty high school girl as apparently it wasn’t the way to impress the parents on your first day. I figured that once I got to know them, then I would adjust my attire if necessary and it proved to be appropriate.

When I rang the doorbell Nathan’s father answered and introduced himself. I tried to keep a straight face as he instinctively did what most guys do when I first meet them - give me the once over. Well, hopefully he was pleased with what he saw. As conservative as I tried to be, it wasn’t like I was dressed like a nun. The jeans were just tight enough to show off my ass without being painted on. My blouse was buttoned appropriately but not to my neck. It was the right size for me (or at least “right” as defined by the store guides), although maybe a little on the small side which helped to show off my boobs just a little bit. My bra felt uncomfortable (God I HATE them) but without it my nipples would’ve been poking through and a much as it would have been fun to see his reaction, I didn’t think it was appropriate on our first time meeting one another.

Nathan’s dad invited me in and as I stepped inside and got a look around, it was all I could do not to stare at the interior furnishings. When I said they were well-off, that was obviously more than a bit of an understatement. The furniture was immaculate and I doubted all paintings on the wall were just reproductions. He led me through the house without saying a word and then up a staircase to a door about midway down a long hallway.

“We set up a study room for you to use when you’re here,” he explained, “Nathan will be in shortly. Make yourself at home.”

I stepped into the room and looked around. I heard him hesitate at the door for a second and then his footsteps disappeared down the hall. No doubt he took a good look at my ass before he left but that was OK with me. Really, what’s the point in dressing to show off your ass if nobody looks at it?

Looking around, I was impressed. The room as set up like a miniature school room. There was a desk for the “student” and a larger one for the “teacher”. An new Apple computer sat on a table to one side and a nearby bookshelf was filled with various books and computer programs. There was a white board, various supplies and even a video camera although I wasn’t sure what I was supposed to do with THAT. I smiled to myself as I thought that maybe daddy had some ideas about making a “naughty schoolgirl” video.

My thoughts may have gone further in the gutter had not the door opened again and in returned the father with young Nathan in tow. Nathan certainly didn’t look too thrilled about the situation but then he saw me and for just an instant, the frown on his face softened but then quickly returned as he continued his protests.

“Come on Dad, I can’t believe you’re making me do this. It’s summer!”

“Dammit, I told you to behave yourself,” his dad hissed at him under his breath as if he was trying to keep me from hearing.

It was clear enough for anyone in the room to hear but I pretended I didn’t hear anything and stood up to greet Nathan. Introductions were made, we shook hands, and then dad made his exit.

During the first tutoring session with a new kid, I try to spend most of the time getting to know the kid rather than trying to get any real instruction accomplished. The whole point of having a tutor is to individualize the instruction and in order to do that, I need to know more about the individual. Soon I learned Nathan was an only child (not a surprise) and both of his parents worked (again, not a surprise). Apparently dad had an office over the garage (it held three cars it’s not like the office was a closet) where he ran some form of accounting business. Mom worked as some kind of manager at an expensive clothing store at the mall and was generally gone most of the day, leaving Nathan on his own most of the time.