Jenny and I met at a Learning center. I had just moved to Dallas, and was working as a co-op for a big electronics company while finishing up my last few college courses through correspondence. My ex-girlfriend from college had left me in quite a bit of debt, and I wanted to be free from it by the time I graduated. So I looked for, and found, a temporary job tutoring a couple of weeknights, and all day Saturdays.
I was working 6 days a week, and studying Sundays- but that's what I wanted at that time: no women, just focus on graduation, and a permanent position at my firm after that. The temporary job involved a long drive to a suburb, but it gave me time to clear my head, and think. I was able to live anonymously in a new city, and recover from the heartbreak leading up to the breakup with Rachel. I wanted to use this opportunity to concentrate on my future, and start a new life.
Jenny was the director of the center, and reported to the President. She, along with Glenda, the President, interviewed me for the job. She was beautiful, I could see that, but the only thing I cared about was convincing her and Glenda to offer me the job. Rather than paying attention to her looks, I was more impressed with the fact that she was very well spoken, asked me pointed questions about my educational background, and seemed to acknowledge my goals. I was very happy when she called me back in a couple of days to offer me the position, and relieved to find out that I would be able to pay off all my bills according to plan.
The job turned out to be exactly what I had hoped for. I would work all day and run Monday and Wednesday evenings. By the time I got to work Tuesday and Thursday afternoons, I had just enough stamina to focus on the kids and help them with their studies. It was a little better on Saturdays, when I was there from 8 to 5, and I had more energy. I managed to do a pretty good job there, mostly because I enjoyed the tasks, the kids, and the people that I worked with. Within a couple of months, Glenda gave me a raise, and Jenny started to take a liking to me.
We would talk in between attending to different students, and I was drawn to her because she was a terrific boss. She not only rewarded the tutors for a job well done, and also provided feedback and constructive criticism about how to help the students. When I got the first raise, she let me know that she was aware how hard I was working, and that she was very pleased with the job I was doing.
I asked her if there was something I could improve on, and her reply was, "Yes, you could be friendlier."
Still, I did not think much of it at that time. She was around 32, about 10 years older than me, and my boss. Not only that, I wanted to keep my nose as close to the ground as possible. And she was not someone that I would have been really attracted to at first sight. Being a runner, and coming from a tropical background, I always noticed the dark haired, lithe athletic types. Most of my previous dates had looked like skinny cheerleaders. Jenny was different, and more reserved. She did not laugh, she smiled. She had green eyes, curly blond hair up to her shoulders, and was voluptuous. Her 5'6'' frame was always stylishly dressed, and it was easy to notice the gorgeous curves.
It was not too difficult to picture her as the wife of a successful man, with a kid or two at home, and everything in order- except she did not wear a ring. Quite frankly, she made me very self-conscious, and lust was the farthest thing fro my mind when I talked to her.
It was only when we started talking more that I found out that the truth was far from what I had thought. I discovered that she was divorced, and that it had been a long painful process. She did not have any kids, and was also trying to return some sense of normalcy in her life by immersing herself in work.
These facts made me feel me much closer to my boss than before. I realized that we were both living the same life, in different ways. Yes, she was still my boss, but now she was also a friend that I wanted to open up to. As we started going to lunch on Saturdays, I told her about my past, and how I could empathize with her, because I had been burned too. We started forming a bond that grew stronger every week. Pretty soon, my reserved boss would share private jokes by pulling me aside, or confide some work related stuff to me. We also started talking to each other over the phone outside of work, and I could tell she was getting attracted to me. Pretty soon it was a lot more obvious- touching my hair, or commenting on my lean frame, or making fun of my huge pasta meals after running, and offering to cook for me.
It was exciting, but at the same time, a little bit nerve wrecking. After all, I was only 22, with not much experience with older women. The only other time I had been with someone older than me was with Lisa, in Houston, during a summer internship, and even then she was only a couple of years my senior. I also definitely did not want to lose my job, and was worried about what other people at work might start thinking. But I also did not want to give up on Jenny. It was exciting to receive the attention from someone that I respected a lot, and even more exciting because of my self imposed monk hood.
Somehow she started feeling like a forbidden fruit to me. I wanted to hold and comfort her, make her happy, and make love to her. It also did not help that I had not had sex in a long time. I started dreaming about her as I went to bed, and daydreaming about her at my regular job. I would imagine undressing her, and having her naked body next to mine, and then doing to her everything wicked that I could think of.
I would remember how my previous girlfriends had always enjoyed my tongue, and now I wanted to use it on her clit. I would also remember how my ex-girlfriend would marvel at my erection- my normally unassuming penis would become a thick eight-inch monster when it got excited.
Now, I would dream about pounding Jenny with my cock. I wanted to see her face, and the look in her eyes as she came. I had to masturbate every night to relieve my raging hard-on, before I could fall asleep. As my cum shot straight up and fell on my tight stomach, the last thing I could think about before falling asleep was that I wished I came on her soft belly.