I swear when I started tutoring it wasn't with the intention of hooking up with my students or their family members. I always had the best intentions as I really do enjoy the work. Teaching has always been a passion of mine, whether it be in a larger setting or one on one. But, given a choice I do prefer the one on one, giving individual attention to a struggling student and making a difference in their education and life.
Through the years I have tutored kids as young at 14 and parents as old as 48. I also always try to be very professional and respectful. I have also tried to take extra special care to not put myself into situations that could lead to accusations with female students specifically, especially the underage ones. Inevitably through the years there have been some slip ups of mine. Encounters that have led to experiences that were exciting, erotic and while legal, not something I could ever tell my wife about.
A little about me. Currently I am a 49-year-old engineer, still struggling to make ends meet, partly because both me and my wife have expensive tastes. But knowing this I keep tutoring on the side to help afford these extravagances. I have been tutoring for about 20 years now and have thoroughly enjoyed it mostly. There have been a couple of students I would rather have never met, but I learned from them to set up my expectations early with them. I am also married 22 years now and have 2 kids, the youngest being 14, oldest 20. While we are still in love, there has been a lack of passion in the relationship for a long time. These series of stories will follow my experiences that I could never share with my wife.
Before this first time there were times I was definitely tempted, but I never actually acted upon my temptations with students or parents. The first time will forever stick into my brain though, as they always do. She was 18 years old, in her senior year of high school, desperate to pass her math class that was required for graduation. Her name was Jen, a petite brunette with long hair, tight body with smaller B cup breasts. She was also a hard-working student that just couldn't seem to grasp some of the concepts. As I tell lots of people, my job as a tutor is to translate what their teacher says into language the students can understand, this was no exception. After the first few sessions I could see she was starting to be able to translate some of the instructions herself, starting to be able to grasp the concepts with less and less interaction from me.
Throughout our time tutoring she became more and more relaxed, able to joke around more with me, much more comfortable. Our conversations didn't always revolve around her homework, or the math test we were studying for. She was comfortable now to do the work, while starting to converse on a more personal note. This is the best part about being a tutor, when you get to see this amount of success from a student.
One particular session she started talking about her boyfriend and a recent fight they had. I could tell he was an asshole just from how she described him, and I once again wondered at how a lot of very attractive women dated men that were just complete assholes and never treated them with the respect they deserved. It turns out she had caught him flirting with another girl and rightfully she didn't appreciate this. I made a comment about how disrespectful that was and if I was him, I would never do that to her, and she could do so much better. She stopped what she was doing and looked at me with a quizzical expression, pencil at her lips and said, oh really?
