Here is my third story. Another memorable experience from my days as an undergraduate, trying to make a few bucks to pay the bills.
I'm fortunate. I grew up in a middle-class neighborhood in the northeast US. My dad worked and my mom stayed at home. We didn't have anything fancy, and there was nothing we went without. And when it came time for college, I didn't have much to worry about. My parents took care of tuition and room and board and the rest was on me. Many of my classmates had $50k or more in debt after school. Not me, but I still needed some money for going out on dates and to enjoy life beyond my studies.
So throughout college, I had a few part time jobs. I worked fast food a few hours a week. Subway. Wendy's. I met some interesting characters along the way and met some great people and learned a lot about life and leadership in ways that you can't in any college course.
During my junior year, one of my managers invited me to join them and their family at religious services and I did. Something different and a chance to meet some new people. One of them was Kathy.
Kathy was nice and made a great first impression for a variety of reasons. Kathy had a teenage daughter who was struggling with math and she asked if I did any tutoring. I didn't, at least not actively, and I wasn't getting paid for it. But I told Kathy that yes, I did some tutoring and I would be happy to discuss how I might be able to help.
So let me tell you about Kathy and why I was so quick to say yes and agree to a conversation. She was divorced. Extremely attractive. Very tan. Fit. Short. Dark hair. Dark eyes. Very exotic looking. And a set of fake tits to compliment her looks.
Kathy and I exchanged phone numbers. A few days later she called me to talk about challenges with her daughter at school. Math. An area where I could indeed help as I was taking graduate level calculus as an elective towards my engineering degree. We decided that we would have our first meeting at a Starbuck's, all three of us together to talk about specific challenges, come up with a plan and a reasonable hourly rate.
The following week we all met and talked and I gathered enough information to make a plan. Weekly sessions. 90 minutes. $30 cash. Kathy agreed. And it gave me a chance to see Kathy in more casual clothes than what I had observed at religious services the previous week. She was even more attractive than I recalled and wasn't shy about showing off her chest.
And maybe it was me, but it looked like she was trying to make sure I noticed. At one point she caught me staring and when we made eye contact again, she winked at me. I can only imagine how many shades of red I turned. Me, a 20-year-old undergrad. Her, a MILF in her mid 30's who could probably still get most any man she wanted.
What was she thinking? What was I thinking? This was just business. A chance for me to make a few bucks on the side through someone I met at services. Or was there more going on?
The next weekend, I went to their home. Kathy's daughter and I sat at the kitchen table while Kathy did stuff around the house. It was a good session. I think it was helpful and we all agreed to do it again the next weekend. Same time, same place. Kathy asked if I wanted a glass of wine before I left, and I politely declined. I wanted to get home and shower as I had a date that night.
She went to her purse to pay me and realized that she didn't have any cash. She asked if she could pay me next weekend and promised that she would have it. I agreed. I didn't need the money for my date, and in my mind, everyone makes honest mistakes. There is no way she would forget the following weekend. And so off I went to enjoy my evening.
And so the next weekend came, and I went to their house for another session. Her daughter told me about how the work we did the previous weekend helped with her quiz and that she hoped we would do more of the same. It was good to hear that my tutoring was helpful. Some kids are rebellious and some just want some one on one attention. That's all she needed, and I was glad to help and make a few bucks.
After the session, Kathy asked if I could stay and have a glass of wine. I didn't have any plans, so I agreed. As we sat down, her daughter went to a friend's house for dinner and a sleep over. I was now alone with Kathy and a bit curious where this was going.